CINXE.COM

<!DOCTYPE html> <html class="client-nojs vector-feature-language-in-header-enabled vector-feature-language-in-main-page-header-disabled vector-feature-sticky-header-disabled vector-feature-page-tools-pinned-disabled vector-feature-toc-pinned-clientpref-1 vector-feature-main-menu-pinned-disabled vector-feature-limited-width-clientpref-1 vector-feature-limited-width-content-enabled vector-feature-custom-font-size-clientpref-1 vector-feature-appearance-pinned-clientpref-1 vector-feature-night-mode-enabled skin-theme-clientpref-day vector-toc-available" lang="en" dir="ltr"> <head> <meta charset="UTF-8"> <title>Ethinylestradiol - Wikipedia</title> <script>(function(){var className="client-js vector-feature-language-in-header-enabled vector-feature-language-in-main-page-header-disabled vector-feature-sticky-header-disabled vector-feature-page-tools-pinned-disabled vector-feature-toc-pinned-clientpref-1 vector-feature-main-menu-pinned-disabled vector-feature-limited-width-clientpref-1 vector-feature-limited-width-content-enabled vector-feature-custom-font-size-clientpref-1 vector-feature-appearance-pinned-clientpref-1 vector-feature-night-mode-enabled skin-theme-clientpref-day vector-toc-available";var cookie=document.cookie.match(/(?:^|; )enwikimwclientpreferences=([^;]+)/);if(cookie){cookie[1].split('%2C').forEach(function(pref){className=className.replace(new RegExp('(^| )'+pref.replace(/-clientpref-\w+$|[^\w-]+/g,'')+'-clientpref-\\w+( |$)'),'$1'+pref+'$2');});}document.documentElement.className=className;}());RLCONF={"wgBreakFrames":false,"wgSeparatorTransformTable":["",""],"wgDigitTransformTable":["",""],"wgDefaultDateFormat":"dmy", "wgMonthNames":["","January","February","March","April","May","June","July","August","September","October","November","December"],"wgRequestId":"8d9c4395-6e7b-4bce-bcc7-6bcf2e42a654","wgCanonicalNamespace":"","wgCanonicalSpecialPageName":false,"wgNamespaceNumber":0,"wgPageName":"Ethinylestradiol","wgTitle":"Ethinylestradiol","wgCurRevisionId":1257041108,"wgRevisionId":1257041108,"wgArticleId":2421454,"wgIsArticle":true,"wgIsRedirect":false,"wgAction":"view","wgUserName":null,"wgUserGroups":["*"],"wgCategories":["All articles with dead external links","Articles with dead external links from July 2022","CS1: long volume value","CS1 German-language sources (de)","CS1 maint: DOI inactive as of November 2024","CS1 French-language sources (fr)","Articles with short description","Short description is different from Wikidata","Use dmy dates from March 2024","Drugs with non-standard legal status","ECHA InfoCard ID from Wikidata","All articles with unsourced statements", "Articles with unsourced statements from July 2018","CYP1A2 inhibitors","Ethynyl compounds","Antigonadotropins","Estranes","GPER agonists","Hepatotoxins","Hormonal antineoplastic drugs","Hormonal contraception","Human drug metabolites","Prolactin releasers","Hydroxyarenes","Synthetic estrogens"],"wgPageViewLanguage":"en","wgPageContentLanguage":"en","wgPageContentModel":"wikitext","wgRelevantPageName":"Ethinylestradiol","wgRelevantArticleId":2421454,"wgIsProbablyEditable":true,"wgRelevantPageIsProbablyEditable":true,"wgRestrictionEdit":[],"wgRestrictionMove":[],"wgNoticeProject":"wikipedia","wgCiteReferencePreviewsActive":false,"wgFlaggedRevsParams":{"tags":{"status":{"levels":1}}},"wgMediaViewerOnClick":true,"wgMediaViewerEnabledByDefault":true,"wgPopupsFlags":0,"wgVisualEditor":{"pageLanguageCode":"en","pageLanguageDir":"ltr","pageVariantFallbacks":"en"},"wgMFDisplayWikibaseDescriptions":{"search":true,"watchlist":true,"tagline":false,"nearby":true}, "wgWMESchemaEditAttemptStepOversample":false,"wgWMEPageLength":100000,"wgRelatedArticlesCompat":[],"wgCentralAuthMobileDomain":false,"wgEditSubmitButtonLabelPublish":true,"wgULSPosition":"interlanguage","wgULSisCompactLinksEnabled":false,"wgVector2022LanguageInHeader":true,"wgULSisLanguageSelectorEmpty":false,"wgWikibaseItemId":"Q415563","wgCheckUserClientHintsHeadersJsApi":["brands","architecture","bitness","fullVersionList","mobile","model","platform","platformVersion"],"GEHomepageSuggestedEditsEnableTopics":true,"wgGETopicsMatchModeEnabled":false,"wgGEStructuredTaskRejectionReasonTextInputEnabled":false,"wgGELevelingUpEnabledForUser":false};RLSTATE={"ext.globalCssJs.user.styles":"ready","site.styles":"ready","user.styles":"ready","ext.globalCssJs.user":"ready","user":"ready","user.options":"loading","ext.cite.styles":"ready","skins.vector.search.codex.styles":"ready","skins.vector.styles":"ready","skins.vector.icons":"ready","jquery.tablesorter.styles":"ready", "jquery.makeCollapsible.styles":"ready","ext.wikimediamessages.styles":"ready","ext.visualEditor.desktopArticleTarget.noscript":"ready","ext.uls.interlanguage":"ready","wikibase.client.init":"ready","ext.wikimediaBadges":"ready"};RLPAGEMODULES=["ext.cite.ux-enhancements","mediawiki.page.media","site","mediawiki.page.ready","jquery.tablesorter","jquery.makeCollapsible","mediawiki.toc","skins.vector.js","ext.centralNotice.geoIP","ext.centralNotice.startUp","ext.gadget.ReferenceTooltips","ext.gadget.switcher","ext.urlShortener.toolbar","ext.centralauth.centralautologin","mmv.bootstrap","ext.popups","ext.visualEditor.desktopArticleTarget.init","ext.visualEditor.targetLoader","ext.echo.centralauth","ext.eventLogging","ext.wikimediaEvents","ext.navigationTiming","ext.uls.interface","ext.cx.eventlogging.campaigns","ext.cx.uls.quick.actions","wikibase.client.vector-2022","ext.checkUser.clientHints","ext.quicksurveys.init","ext.growthExperiments.SuggestedEditSession","wikibase.sidebar.tracking" ];</script> <script>(RLQ=window.RLQ||[]).push(function(){mw.loader.impl(function(){return["user.options@12s5i",function($,jQuery,require,module){mw.user.tokens.set({"patrolToken":"+\\","watchToken":"+\\","csrfToken":"+\\"}); }];});});</script> <link rel="stylesheet" href="/w/load.php?lang=en&modules=ext.cite.styles%7Cext.uls.interlanguage%7Cext.visualEditor.desktopArticleTarget.noscript%7Cext.wikimediaBadges%7Cext.wikimediamessages.styles%7Cjquery.makeCollapsible.styles%7Cjquery.tablesorter.styles%7Cskins.vector.icons%2Cstyles%7Cskins.vector.search.codex.styles%7Cwikibase.client.init&only=styles&skin=vector-2022"> <script async="" src="/w/load.php?lang=en&modules=startup&only=scripts&raw=1&skin=vector-2022"></script> <meta name="ResourceLoaderDynamicStyles" content=""> <link rel="stylesheet" href="/w/load.php?lang=en&modules=site.styles&only=styles&skin=vector-2022"> <meta name="generator" content="MediaWiki 1.44.0-wmf.4"> <meta name="referrer" content="origin"> <meta name="referrer" content="origin-when-cross-origin"> <meta name="robots" content="max-image-preview:standard"> <meta name="format-detection" content="telephone=no"> <meta property="og:image" content="https://upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Ethinylestradiol.svg/1200px-Ethinylestradiol.svg.png"> <meta property="og:image:width" content="1200"> <meta property="og:image:height" content="827"> <meta property="og:image" content="https://upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Ethinylestradiol.svg/800px-Ethinylestradiol.svg.png"> <meta property="og:image:width" content="800"> <meta property="og:image:height" content="552"> <meta property="og:image" content="https://upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Ethinylestradiol.svg/640px-Ethinylestradiol.svg.png"> <meta property="og:image:width" content="640"> <meta property="og:image:height" content="441"> <meta name="viewport" content="width=1120"> <meta property="og:title" content="Ethinylestradiol - Wikipedia"> <meta property="og:type" content="website"> <link rel="preconnect" href="//upload.wikimedia.org"> <link rel="alternate" media="only screen and (max-width: 640px)" href="//en.m.wikipedia.org/wiki/Ethinylestradiol"> <link rel="alternate" type="application/x-wiki" title="Edit this page" href="/w/index.php?title=Ethinylestradiol&action=edit"> <link rel="apple-touch-icon" href="/static/apple-touch/wikipedia.png"> <link rel="icon" href="/static/favicon/wikipedia.ico"> <link rel="search" type="application/opensearchdescription+xml" href="/w/rest.php/v1/search" title="Wikipedia (en)"> <link rel="EditURI" type="application/rsd+xml" href="//en.wikipedia.org/w/api.php?action=rsd"> <link rel="canonical" href="https://en.wikipedia.org/wiki/Ethinylestradiol"> <link rel="license" href="https://creativecommons.org/licenses/by-sa/4.0/deed.en"> <link rel="alternate" type="application/atom+xml" title="Wikipedia Atom feed" href="/w/index.php?title=Special:RecentChanges&feed=atom"> <link rel="dns-prefetch" href="//meta.wikimedia.org" /> <link rel="dns-prefetch" href="//login.wikimedia.org"> </head> <body class="skin--responsive skin-vector skin-vector-search-vue mediawiki ltr sitedir-ltr mw-hide-empty-elt ns-0 ns-subject mw-editable page-Ethinylestradiol rootpage-Ethinylestradiol skin-vector-2022 action-view"><a class="mw-jump-link" href="#bodyContent">Jump to content</a> <div class="vector-header-container"> <header class="vector-header mw-header"> <div class="vector-header-start"> <nav class="vector-main-menu-landmark" aria-label="Site"> <div id="vector-main-menu-dropdown" class="vector-dropdown vector-main-menu-dropdown vector-button-flush-left vector-button-flush-right" > <input type="checkbox" id="vector-main-menu-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-main-menu-dropdown" class="vector-dropdown-checkbox " aria-label="Main menu" > <label id="vector-main-menu-dropdown-label" for="vector-main-menu-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" > Main menu </label> <div class="vector-dropdown-content"> <div id="vector-main-menu-unpinned-container" class="vector-unpinned-container"> <div id="vector-main-menu" class="vector-main-menu vector-pinnable-element"> <div class="vector-pinnable-header vector-main-menu-pinnable-header vector-pinnable-header-unpinned" data-feature-name="main-menu-pinned" data-pinnable-element-id="vector-main-menu" data-pinned-container-id="vector-main-menu-pinned-container" data-unpinned-container-id="vector-main-menu-unpinned-container" > <div class="vector-pinnable-header-label">Main menu</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-main-menu.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-main-menu.unpin">hide</button> </div> <div id="p-navigation" class="vector-menu mw-portlet mw-portlet-navigation" > <div class="vector-menu-heading"> Navigation </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="n-mainpage-description" class="mw-list-item"><a href="/wiki/Main_Page" title="Visit the main page [z]" accesskey="z">Main page</a></li><li id="n-contents" class="mw-list-item"><a href="/wiki/Wikipedia:Contents" title="Guides to browsing Wikipedia">Contents</a></li><li id="n-currentevents" class="mw-list-item"><a href="/wiki/Portal:Current_events" title="Articles related to current events">Current events</a></li><li id="n-randompage" class="mw-list-item"><a href="/wiki/Special:Random" title="Visit a randomly selected article [x]" accesskey="x">Random article</a></li><li id="n-aboutsite" class="mw-list-item"><a href="/wiki/Wikipedia:About" title="Learn about Wikipedia and how it works">About Wikipedia</a></li><li id="n-contactpage" class="mw-list-item"><a href="//en.wikipedia.org/wiki/Wikipedia:Contact_us" title="How to contact Wikipedia">Contact us</a></li> </ul> </div> </div> <div id="p-interaction" class="vector-menu mw-portlet mw-portlet-interaction" > <div class="vector-menu-heading"> Contribute </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="n-help" class="mw-list-item"><a href="/wiki/Help:Contents" title="Guidance on how to use and edit Wikipedia">Help</a></li><li id="n-introduction" class="mw-list-item"><a href="/wiki/Help:Introduction" title="Learn how to edit Wikipedia">Learn to edit</a></li><li id="n-portal" class="mw-list-item"><a href="/wiki/Wikipedia:Community_portal" title="The hub for editors">Community portal</a></li><li id="n-recentchanges" class="mw-list-item"><a href="/wiki/Special:RecentChanges" title="A list of recent changes to Wikipedia [r]" accesskey="r">Recent changes</a></li><li id="n-upload" class="mw-list-item"><a href="/wiki/Wikipedia:File_upload_wizard" title="Add images or other media for use on Wikipedia">Upload file</a></li> </ul> </div> </div> </div> </div> </div> </div> </nav> <a href="/wiki/Main_Page" class="mw-logo"> <img class="mw-logo-icon" src="/static/images/icons/wikipedia.png" alt="" aria-hidden="true" height="50" width="50"> <img class="mw-logo-wordmark" alt="Wikipedia" src="/static/images/mobile/copyright/wikipedia-wordmark-en.svg" style="width: 7.5em; height: 1.125em;"> <img class="mw-logo-tagline" alt="The Free Encyclopedia" src="/static/images/mobile/copyright/wikipedia-tagline-en.svg" width="117" height="13" style="width: 7.3125em; height: 0.8125em;"> </a> </div> <div class="vector-header-end"> <div id="p-search" role="search" class="vector-search-box-vue vector-search-box-collapses vector-search-box-show-thumbnail vector-search-box-auto-expand-width vector-search-box"> <a href="/wiki/Special:Search" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only search-toggle" title="Search Wikipedia [f]" accesskey="f"> Search </a> <div class="vector-typeahead-search-container"> <div class="cdx-typeahead-search cdx-typeahead-search--show-thumbnail cdx-typeahead-search--auto-expand-width"> <form action="/w/index.php" id="searchform" class="cdx-search-input cdx-search-input--has-end-button"> <div id="simpleSearch" class="cdx-search-input__input-wrapper" data-search-loc="header-moved"> <div class="cdx-text-input cdx-text-input--has-start-icon"> <input class="cdx-text-input__input" type="search" name="search" placeholder="Search Wikipedia" aria-label="Search Wikipedia" autocapitalize="sentences" title="Search Wikipedia [f]" accesskey="f" id="searchInput" > </div> <input type="hidden" name="title" value="Special:Search"> </div> <button class="cdx-button cdx-search-input__end-button">Search</button> </form> </div> </div> </div> <nav class="vector-user-links vector-user-links-wide" aria-label="Personal tools"> <div class="vector-user-links-main"> <div id="p-vector-user-menu-preferences" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <div id="p-vector-user-menu-userpage" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-dropdown" class="vector-dropdown " title="Change the appearance of the page's font size, width, and color" > <input type="checkbox" id="vector-appearance-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-appearance-dropdown" class="vector-dropdown-checkbox " aria-label="Appearance" > <label id="vector-appearance-dropdown-label" for="vector-appearance-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" > Appearance </label> <div class="vector-dropdown-content"> <div id="vector-appearance-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <div id="p-vector-user-menu-notifications" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <div id="p-vector-user-menu-overflow" class="vector-menu mw-portlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-sitesupport-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="https://donate.wikimedia.org/wiki/Special:FundraiserRedirector?utm_source=donate&utm_medium=sidebar&utm_campaign=C13_en.wikipedia.org&uselang=en" class="">Donate</a> </li> <li id="pt-createaccount-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="/w/index.php?title=Special:CreateAccount&returnto=Ethinylestradiol" title="You are encouraged to create an account and log in; however, it is not mandatory" class="">Create account</a> </li> <li id="pt-login-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="/w/index.php?title=Special:UserLogin&returnto=Ethinylestradiol" title="You're encouraged to log in; however, it's not mandatory. [o]" accesskey="o" class="">Log in</a> </li> </ul> </div> </div> </div> <div id="vector-user-links-dropdown" class="vector-dropdown vector-user-menu vector-button-flush-right vector-user-menu-logged-out" title="Log in and more options" > <input type="checkbox" id="vector-user-links-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-user-links-dropdown" class="vector-dropdown-checkbox " aria-label="Personal tools" > <label id="vector-user-links-dropdown-label" for="vector-user-links-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" > Personal tools </label> <div class="vector-dropdown-content"> <div id="p-personal" class="vector-menu mw-portlet mw-portlet-personal user-links-collapsible-item" title="User menu" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-sitesupport" class="user-links-collapsible-item mw-list-item"><a href="https://donate.wikimedia.org/wiki/Special:FundraiserRedirector?utm_source=donate&utm_medium=sidebar&utm_campaign=C13_en.wikipedia.org&uselang=en">Donate</a></li><li id="pt-createaccount" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Special:CreateAccount&returnto=Ethinylestradiol" title="You are encouraged to create an account and log in; however, it is not mandatory"> Create account</a></li><li id="pt-login" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Special:UserLogin&returnto=Ethinylestradiol" title="You're encouraged to log in; however, it's not mandatory. [o]" accesskey="o"> Log in</a></li> </ul> </div> </div> <div id="p-user-menu-anon-editor" class="vector-menu mw-portlet mw-portlet-user-menu-anon-editor" > <div class="vector-menu-heading"> Pages for logged out editors <a href="/wiki/Help:Introduction" aria-label="Learn more about editing">learn more</a> </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-anoncontribs" class="mw-list-item"><a href="/wiki/Special:MyContributions" title="A list of edits made from this IP address [y]" accesskey="y">Contributions</a></li><li id="pt-anontalk" class="mw-list-item"><a href="/wiki/Special:MyTalk" title="Discussion about edits from this IP address [n]" accesskey="n">Talk</a></li> </ul> </div> </div> </div> </div> </nav> </div> </header> </div> <div class="mw-page-container"> <div class="mw-page-container-inner"> <div class="vector-sitenotice-container"> <div id="siteNotice"></div> </div> <div class="vector-column-start"> <div class="vector-main-menu-container"> <div id="mw-navigation"> <nav id="mw-panel" class="vector-main-menu-landmark" aria-label="Site"> <div id="vector-main-menu-pinned-container" class="vector-pinned-container"> </div> </nav> </div> </div> <div class="vector-sticky-pinned-container"> <nav id="mw-panel-toc" aria-label="Contents" data-event-name="ui.sidebar-toc" class="mw-table-of-contents-container vector-toc-landmark"> <div id="vector-toc-pinned-container" class="vector-pinned-container"> <div id="vector-toc" class="vector-toc vector-pinnable-element"> <div class="vector-pinnable-header vector-toc-pinnable-header vector-pinnable-header-pinned" data-feature-name="toc-pinned" data-pinnable-element-id="vector-toc" > <h2 class="vector-pinnable-header-label">Contents</h2> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-toc.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-toc.unpin">hide</button> </div> <ul class="vector-toc-contents" id="mw-panel-toc-list"> <li id="toc-mw-content-text" class="vector-toc-list-item vector-toc-level-1"> <a href="#" class="vector-toc-link"> <div class="vector-toc-text">(Top)</div> </a> </li> <li id="toc-Medical_uses" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Medical_uses"> <div class="vector-toc-text"> 1 Medical uses </div> </a> <button aria-controls="toc-Medical_uses-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Medical uses subsection </button> <ul id="toc-Medical_uses-sublist" class="vector-toc-list"> <li id="toc-Available_forms" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Available_forms"> <div class="vector-toc-text"> 1.1 Available forms </div> </a> <ul id="toc-Available_forms-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Contraindications" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Contraindications"> <div class="vector-toc-text"> 2 Contraindications </div> </a> <ul id="toc-Contraindications-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Side_effects" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Side_effects"> <div class="vector-toc-text"> 3 Side effects </div> </a> <button aria-controls="toc-Side_effects-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Side effects subsection </button> <ul id="toc-Side_effects-sublist" class="vector-toc-list"> <li id="toc-Long-term_effects" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Long-term_effects"> <div class="vector-toc-text"> 3.1 Long-term effects </div> </a> <ul id="toc-Long-term_effects-sublist" class="vector-toc-list"> <li id="toc-Blood_clots" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Blood_clots"> <div class="vector-toc-text"> 3.1.1 Blood clots </div> </a> <ul id="toc-Blood_clots-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cardiovascular_issues" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Cardiovascular_issues"> <div class="vector-toc-text"> 3.1.2 Cardiovascular issues </div> </a> <ul id="toc-Cardiovascular_issues-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Liver_damage" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Liver_damage"> <div class="vector-toc-text"> 3.1.3 Liver damage </div> </a> <ul id="toc-Liver_damage-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Uterine_cancer" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Uterine_cancer"> <div class="vector-toc-text"> 3.1.4 Uterine cancer </div> </a> <ul id="toc-Uterine_cancer-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Ecological_Effects" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Ecological_Effects"> <div class="vector-toc-text"> 3.2 Ecological Effects </div> </a> <ul id="toc-Ecological_Effects-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Overdose" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Overdose"> <div class="vector-toc-text"> 4 Overdose </div> </a> <ul id="toc-Overdose-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Interactions" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Interactions"> <div class="vector-toc-text"> 5 Interactions </div> </a> <ul id="toc-Interactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pharmacology" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Pharmacology"> <div class="vector-toc-text"> 6 Pharmacology </div> </a> <button aria-controls="toc-Pharmacology-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Pharmacology subsection </button> <ul id="toc-Pharmacology-sublist" class="vector-toc-list"> <li id="toc-Pharmacodynamics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmacodynamics"> <div class="vector-toc-text"> 6.1 Pharmacodynamics </div> </a> <ul id="toc-Pharmacodynamics-sublist" class="vector-toc-list"> <li id="toc-Antiandrogenic_and_antigonadotropic_effects" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Antiandrogenic_and_antigonadotropic_effects"> <div class="vector-toc-text"> 6.1.1 Antiandrogenic and antigonadotropic effects </div> </a> <ul id="toc-Antiandrogenic_and_antigonadotropic_effects-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Effects_on_liver_protein_synthesis" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Effects_on_liver_protein_synthesis"> <div class="vector-toc-text"> 6.1.2 Effects on liver protein synthesis </div> </a> <ul id="toc-Effects_on_liver_protein_synthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Differences_from_estradiol" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Differences_from_estradiol"> <div class="vector-toc-text"> 6.1.3 Differences from estradiol </div> </a> <ul id="toc-Differences_from_estradiol-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Pharmacokinetics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmacokinetics"> <div class="vector-toc-text"> 6.2 Pharmacokinetics </div> </a> <ul id="toc-Pharmacokinetics-sublist" class="vector-toc-list"> <li id="toc-Absorption" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Absorption"> <div class="vector-toc-text"> 6.2.1 Absorption </div> </a> <ul id="toc-Absorption-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Distribution" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Distribution"> <div class="vector-toc-text"> 6.2.2 Distribution </div> </a> <ul id="toc-Distribution-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metabolism" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Metabolism"> <div class="vector-toc-text"> 6.2.3 Metabolism </div> </a> <ul id="toc-Metabolism-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Elimination" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Elimination"> <div class="vector-toc-text"> 6.2.4 Elimination </div> </a> <ul id="toc-Elimination-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Chemistry" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Chemistry"> <div class="vector-toc-text"> 7 Chemistry </div> </a> <button aria-controls="toc-Chemistry-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Chemistry subsection </button> <ul id="toc-Chemistry-sublist" class="vector-toc-list"> <li id="toc-Analogues" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Analogues"> <div class="vector-toc-text"> 7.1 Analogues </div> </a> <ul id="toc-Analogues-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> 8 History </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Society_and_culture" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Society_and_culture"> <div class="vector-toc-text"> 9 Society and culture </div> </a> <button aria-controls="toc-Society_and_culture-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Society and culture subsection </button> <ul id="toc-Society_and_culture-sublist" class="vector-toc-list"> <li id="toc-Generic_names" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Generic_names"> <div class="vector-toc-text"> 9.1 Generic names </div> </a> <ul id="toc-Generic_names-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Brand_names" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Brand_names"> <div class="vector-toc-text"> 9.2 Brand names </div> </a> <ul id="toc-Brand_names-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Availability" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Availability"> <div class="vector-toc-text"> 9.3 Availability </div> </a> <ul id="toc-Availability-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> 10 References </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Further_reading" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Further_reading"> <div class="vector-toc-text"> 11 Further reading </div> </a> <ul id="toc-Further_reading-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" > Toggle the table of contents </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading">Ethinylestradiol</h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 30 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-30" aria-hidden="true" > 30 languages </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A5%D9%8A%D8%AB%D9%8A%D9%86%D9%8A%D9%84_%D8%A5%D9%8A%D8%B3%D8%AA%D8%B1%D8%A7%D8%AF%D9%8A%D9%88%D9%84" title="إيثينيل إيستراديول – Arabic" lang="ar" hreflang="ar" data-title="إيثينيل إيستراديول" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target">العربية</a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A7%D8%AA%DB%8C%D9%86%DB%8C%D9%84_%D8%A7%D8%B3%D8%AA%D8%B1%D8%A7%D8%AF%DB%8C%D9%88%D9%84" title="اتینیل استرادیول – South Azerbaijani" lang="azb" hreflang="azb" data-title="اتینیل استرادیول" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target">تۆرکجه</a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Etinilestradiol" title="Etinilestradiol – Bosnian" lang="bs" hreflang="bs" data-title="Etinilestradiol" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target">Bosanski</a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Ethinylestradiol" title="Ethinylestradiol – Welsh" lang="cy" hreflang="cy" data-title="Ethinylestradiol" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target">Cymraeg</a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Ethinyl%C3%B8stradiol" title="Ethinyløstradiol – Danish" lang="da" hreflang="da" data-title="Ethinyløstradiol" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target">Dansk</a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Ethinylestradiol" title="Ethinylestradiol – German" lang="de" hreflang="de" data-title="Ethinylestradiol" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target">Deutsch</a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Et%C3%BCn%C3%BC%C3%BCl%C3%B6stradiool" title="Etünüülöstradiool – Estonian" lang="et" hreflang="et" data-title="Etünüülöstradiool" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target">Eesti</a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Etinilestradiol" title="Etinilestradiol – Spanish" lang="es" hreflang="es" data-title="Etinilestradiol" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target">Español</a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%D8%AA%DB%8C%D9%86%DB%8C%D9%84%E2%80%8C%D8%A7%D8%B3%D8%AA%D8%B1%D8%A7%D8%AF%DB%8C%D9%88%D9%84" title="اتینیل‌استرادیول – Persian" lang="fa" hreflang="fa" data-title="اتینیل‌استرادیول" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target">فارسی</a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/%C3%89thinylestradiol" title="Éthinylestradiol – French" lang="fr" hreflang="fr" data-title="Éthinylestradiol" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target">Français</a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%97%90%ED%8B%B0%EB%8B%90%EC%97%90%EC%8A%A4%ED%8A%B8%EB%9D%BC%EB%8B%A4%EC%9D%B4%EC%98%AC" title="에티닐에스트라다이올 – Korean" lang="ko" hreflang="ko" data-title="에티닐에스트라다이올" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target">한국어</a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Etinilestradiol" title="Etinilestradiol – Indonesian" lang="id" hreflang="id" data-title="Etinilestradiol" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target">Bahasa Indonesia</a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Etinilestradiolo" title="Etinilestradiolo – Italian" lang="it" hreflang="it" data-title="Etinilestradiolo" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target">Italiano</a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Etinil%C3%B6sztradiol" title="Etinilösztradiol – Hungarian" lang="hu" hreflang="hu" data-title="Etinilösztradiol" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target">Magyar</a></li><li class="interlanguage-link interwiki-mad mw-list-item"><a href="https://mad.wikipedia.org/wiki/Etinilestradiol" title="Etinilestradiol – Madurese" lang="mad" hreflang="mad" data-title="Etinilestradiol" data-language-autonym="Madhurâ" data-language-local-name="Madurese" class="interlanguage-link-target">Madhurâ</a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%8E%E0%B4%A4%E0%B4%BF%E0%B4%A8%E0%B5%88%E0%B4%B2%E0%B5%80%E0%B4%B8%E0%B5%8D%E0%B4%B1%E0%B5%8D%E0%B4%B1%E0%B5%8D%E0%B4%B0%E0%B4%BE%E0%B4%A1%E0%B5%88%E0%B4%AF%E0%B5%8B%E0%B5%BE" title="എതിനൈലീസ്റ്റ്രാഡൈയോൾ – Malayalam" lang="ml" hreflang="ml" data-title="എതിനൈലീസ്റ്റ്രാഡൈയോൾ" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target">മലയാളം</a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Etinilestradiol" title="Etinilestradiol – Malay" lang="ms" hreflang="ms" data-title="Etinilestradiol" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target">Bahasa Melayu</a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Ethinylestradiol" title="Ethinylestradiol – Dutch" lang="nl" hreflang="nl" data-title="Ethinylestradiol" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target">Nederlands</a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A8%E3%83%81%E3%83%8B%E3%83%AB%E3%82%A8%E3%82%B9%E3%83%88%E3%83%A9%E3%82%B8%E3%82%AA%E3%83%BC%E3%83%AB" title="エチニルエストラジオール – Japanese" lang="ja" hreflang="ja" data-title="エチニルエストラジオール" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target">日本語</a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Etinyl%C3%B8stradiol" title="Etinyløstradiol – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Etinyløstradiol" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target">Norsk bokmål</a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Etynyloestradiol" title="Etynyloestradiol – Polish" lang="pl" hreflang="pl" data-title="Etynyloestradiol" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target">Polski</a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Etinilestradiol" title="Etinilestradiol – Portuguese" lang="pt" hreflang="pt" data-title="Etinilestradiol" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target">Português</a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%AD%D1%82%D0%B8%D0%BD%D0%B8%D0%BB%D1%8D%D1%81%D1%82%D1%80%D0%B0%D0%B4%D0%B8%D0%BE%D0%BB" title="Этинилэстрадиол – Russian" lang="ru" hreflang="ru" data-title="Этинилэстрадиол" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target">Русский</a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Etinil_estradiol" title="Etinil estradiol – Serbian" lang="sr" hreflang="sr" data-title="Etinil estradiol" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target">Српски / srpski</a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Etinil_estradiol" title="Etinil estradiol – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Etinil estradiol" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target">Srpskohrvatski / српскохрватски</a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Etinyyliestradioli" title="Etinyyliestradioli – Finnish" lang="fi" hreflang="fi" data-title="Etinyyliestradioli" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target">Suomi</a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Etinylestradiol" title="Etinylestradiol – Swedish" lang="sv" hreflang="sv" data-title="Etinylestradiol" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target">Svenska</a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Etinilestradiol" title="Etinilestradiol – Turkish" lang="tr" hreflang="tr" data-title="Etinilestradiol" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target">Türkçe</a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Ethinylestradiol" title="Ethinylestradiol – Vietnamese" lang="vi" hreflang="vi" data-title="Ethinylestradiol" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target">Tiếng Việt</a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E7%82%94%E9%9B%8C%E9%86%87" title="炔雌醇 – Chinese" lang="zh" hreflang="zh" data-title="炔雌醇" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target">中文</a></li> </ul> <div class="after-portlet after-portlet-lang"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q415563#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-nstab-main" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Ethinylestradiol" title="View the content page [c]" accesskey="c">Article</a></li><li id="ca-talk" class="vector-tab-noicon mw-list-item"><a href="/wiki/Talk:Ethinylestradiol" rel="discussion" title="Discuss improvements to the content page [t]" accesskey="t">Talk</a></li> </ul> </div> </div> <div id="vector-variants-dropdown" class="vector-dropdown emptyPortlet" > <input type="checkbox" id="vector-variants-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-variants-dropdown" class="vector-dropdown-checkbox " aria-label="Change language variant" > <label id="vector-variants-dropdown-label" for="vector-variants-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet" aria-hidden="true" >English </label> <div class="vector-dropdown-content"> <div id="p-variants" class="vector-menu mw-portlet mw-portlet-variants emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> </div> </div> </nav> </div> <div id="right-navigation" class="vector-collapsible"> <nav aria-label="Views"> <div id="p-views" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-views" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-view" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Ethinylestradiol">Read</a></li><li id="ca-edit" class="vector-tab-noicon mw-list-item"><a href="/w/index.php?title=Ethinylestradiol&action=edit" title="Edit this page [e]" accesskey="e">Edit</a></li><li id="ca-history" class="vector-tab-noicon mw-list-item"><a href="/w/index.php?title=Ethinylestradiol&action=history" title="Past revisions of this page [h]" accesskey="h">View history</a></li> </ul> </div> </div> </nav> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-dropdown" class="vector-dropdown vector-page-tools-dropdown" > <input type="checkbox" id="vector-page-tools-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-tools-dropdown" class="vector-dropdown-checkbox " aria-label="Tools" > <label id="vector-page-tools-dropdown-label" for="vector-page-tools-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet" aria-hidden="true" >Tools </label> <div class="vector-dropdown-content"> <div id="vector-page-tools-unpinned-container" class="vector-unpinned-container"> <div id="vector-page-tools" class="vector-page-tools vector-pinnable-element"> <div class="vector-pinnable-header vector-page-tools-pinnable-header vector-pinnable-header-unpinned" data-feature-name="page-tools-pinned" data-pinnable-element-id="vector-page-tools" data-pinned-container-id="vector-page-tools-pinned-container" data-unpinned-container-id="vector-page-tools-unpinned-container" > <div class="vector-pinnable-header-label">Tools</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-page-tools.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-page-tools.unpin">hide</button> </div> <div id="p-cactions" class="vector-menu mw-portlet mw-portlet-cactions emptyPortlet vector-has-collapsible-items" title="More options" > <div class="vector-menu-heading"> Actions </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-more-view" class="selected vector-more-collapsible-item mw-list-item"><a href="/wiki/Ethinylestradiol">Read</a></li><li id="ca-more-edit" class="vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Ethinylestradiol&action=edit" title="Edit this page [e]" accesskey="e">Edit</a></li><li id="ca-more-history" class="vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Ethinylestradiol&action=history">View history</a></li> </ul> </div> </div> <div id="p-tb" class="vector-menu mw-portlet mw-portlet-tb" > <div class="vector-menu-heading"> General </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="t-whatlinkshere" class="mw-list-item"><a href="/wiki/Special:WhatLinksHere/Ethinylestradiol" title="List of all English Wikipedia pages containing links to this page [j]" accesskey="j">What links here</a></li><li id="t-recentchangeslinked" class="mw-list-item"><a href="/wiki/Special:RecentChangesLinked/Ethinylestradiol" rel="nofollow" title="Recent changes in pages linked from this page [k]" accesskey="k">Related changes</a></li><li id="t-upload" class="mw-list-item"><a href="/wiki/Wikipedia:File_Upload_Wizard" title="Upload files [u]" accesskey="u">Upload file</a></li><li id="t-specialpages" class="mw-list-item"><a href="/wiki/Special:SpecialPages" title="A list of all special pages [q]" accesskey="q">Special pages</a></li><li id="t-permalink" class="mw-list-item"><a href="/w/index.php?title=Ethinylestradiol&oldid=1257041108" title="Permanent link to this revision of this page">Permanent link</a></li><li id="t-info" class="mw-list-item"><a href="/w/index.php?title=Ethinylestradiol&action=info" title="More information about this page">Page information</a></li><li id="t-cite" class="mw-list-item"><a href="/w/index.php?title=Special:CiteThisPage&page=Ethinylestradiol&id=1257041108&wpFormIdentifier=titleform" title="Information on how to cite this page">Cite this page</a></li><li id="t-urlshortener" class="mw-list-item"><a href="/w/index.php?title=Special:UrlShortener&url=https%3A%2F%2Fen.wikipedia.org%2Fwiki%2FEthinylestradiol">Get shortened URL</a></li><li id="t-urlshortener-qrcode" class="mw-list-item"><a href="/w/index.php?title=Special:QrCode&url=https%3A%2F%2Fen.wikipedia.org%2Fwiki%2FEthinylestradiol">Download QR code</a></li> </ul> </div> </div> <div id="p-coll-print_export" class="vector-menu mw-portlet mw-portlet-coll-print_export" > <div class="vector-menu-heading"> Print/export </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="coll-download-as-rl" class="mw-list-item"><a href="/w/index.php?title=Special:DownloadAsPdf&page=Ethinylestradiol&action=show-download-screen" title="Download this page as a PDF file">Download as PDF</a></li><li id="t-print" class="mw-list-item"><a href="/w/index.php?title=Ethinylestradiol&printable=yes" title="Printable version of this page [p]" accesskey="p">Printable version</a></li> </ul> </div> </div> <div id="p-wikibase-otherprojects" class="vector-menu mw-portlet mw-portlet-wikibase-otherprojects" > <div class="vector-menu-heading"> In other projects </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="wb-otherproject-link wb-otherproject-commons mw-list-item"><a href="https://commons.wikimedia.org/wiki/Category:Ethinylestradiol" hreflang="en">Wikimedia Commons</a></li><li id="t-wikibase" class="wb-otherproject-link wb-otherproject-wikibase-dataitem mw-list-item"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q415563" title="Structured data on this page hosted by Wikidata [g]" accesskey="g">Wikidata item</a></li> </ul> </div> </div> </div> </div> </div> </div> </nav> </div> </div> </div> <div class="vector-column-end"> <div class="vector-sticky-pinned-container"> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Estrogen medication</div> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title">Ethinylestradiol</caption><tbody><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><a href="/wiki/File:Ethinylestradiol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Ethinylestradiol.svg/235px-Ethinylestradiol.svg.png" decoding="async" width="235" height="162" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Ethinylestradiol.svg/353px-Ethinylestradiol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Ethinylestradiol.svg/470px-Ethinylestradiol.svg.png 2x" data-file-width="512" data-file-height="353" /></a></td></tr><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><a href="/wiki/File:Ethinylestradiol_molecule_ball.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fd/Ethinylestradiol_molecule_ball.png/235px-Ethinylestradiol_molecule_ball.png" decoding="async" width="235" height="188" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fd/Ethinylestradiol_molecule_ball.png/353px-Ethinylestradiol_molecule_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fd/Ethinylestradiol_molecule_ball.png/470px-Ethinylestradiol_molecule_ball.png 2x" data-file-width="2560" data-file-height="2049" /></a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Pronunciation</th><td class="infobox-data"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/ˌɛθɪnɪlˌɛstrəˈdaɪ.əl/</a> </td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Many</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">Ethynylestradiol; Ethinyl estradiol; Ethinyl oestradiol; EE; EE2; 17α-Ethynylestradiol; 17α-Ethynylestra-1,3,5(10)-triene-3,17β-diol; NSC-10973<a href="#cite_note-Elks2014-1">[1]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/American_Society_of_Health-System_Pharmacists" title="American Society of Health-System Pharmacists">AHFS</a>/<a href="/wiki/Drugs.com" title="Drugs.com">Drugs.com</a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://www.drugs.com/international/ethinylestradiol.html">International Drug Names</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/MedlinePlus" title="MedlinePlus">MedlinePlus</a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://medlineplus.gov/druginfo/meds/a604032.html">a604032</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of administration</a></th><td class="infobox-data">• <a href="/wiki/Oral_administration" title="Oral administration">By mouth</a>, <a href="/wiki/Transdermal" title="Transdermal">Transdermal</a>, <a href="/wiki/Vaginal_administration" class="mw-redirect" title="Vaginal administration">Vaginal</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_class" title="Drug class">Drug class</a></th><td class="infobox-data"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogen</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><a href="/wiki/ATC_code_G03" title="ATC code G03">G03CA01</a> (<a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=G03CA01">WHO</a>) <a href="/wiki/ATC_code_L02" title="ATC code L02">L02AA03</a> (<a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=L02AA03">WHO</a>)</li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li>In general: ℞ (Prescription only)</li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a></th><td class="infobox-data">38–48%<a href="#cite_note-pmid2256522-2">[2]</a><a href="#cite_note-pmid22468839-3">[3]</a><a href="#cite_note-pmid8842581-4">[4]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">Protein binding</a></th><td class="infobox-data">97–98% (to <a href="/wiki/Human_serum_albumin" title="Human serum albumin">albumin</a>;<a href="#cite_note-(Firm)Inc2005-5">[5]</a> is not bound to <a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin"><abbr title="sex hormone-binding globulin">SHBG</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip sex hormone-binding globulin)<a href="#cite_note-Micromedex2003-6">[6]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_metabolism" title="Drug metabolism">Metabolism</a></th><td class="infobox-data"><a href="/wiki/Liver" title="Liver">Liver</a> (primarily <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a>)<a href="#cite_note-HughesWaters2016-9">[9]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Metabolite" title="Metabolite">Metabolites</a></th><td class="infobox-data">• <a href="/wiki/Ethinylestradiol_sulfate" title="Ethinylestradiol sulfate">Ethinylestradiol sulfate</a><a href="#cite_note-pmid16112947-7">[7]</a><a href="#cite_note-OettelSchillinger2012-8">[8]</a> • Others<a href="#cite_note-pmid16112947-7">[7]</a><a href="#cite_note-OettelSchillinger2012-8">[8]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Biological_half-life" title="Biological half-life">Elimination half-life</a></th><td class="infobox-data">7–36 hours<a href="#cite_note-HughesWaters2016-9">[9]</a><a href="#cite_note-pmid2256522-2">[2]</a><a href="#cite_note-pmid23375353-10">[10]</a><a href="#cite_note-Shellenberger1986-11">[11]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Excretion" title="Excretion">Excretion</a></th><td class="infobox-data"><a href="/wiki/Feces" title="Feces">Feces</a>: 62%<a href="#cite_note-pmid23375353-10">[10]</a> <a href="/wiki/Urine" title="Urine">Urine</a>: 38%<a href="#cite_note-pmid23375353-10">[10]</a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">(8R,9S,13S,14S,17R)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-4,17-diol</div></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=57-63-6">57-63-6</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/5991">5991</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Guide_to_Pharmacology" title="Guide to Pharmacology">IUPHAR/BPS</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=7071">7071</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB00977">DB00977</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.5770.html">5770</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/423D2T571U">423D2T571U</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/KEGG" title="KEGG">KEGG</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D00554">D00554</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4903">CHEBI:4903</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL691">ChEMBL691</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> (<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID5020576">DTXSID5020576</a> <a href="https://www.wikidata.org/wiki/Q415563#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard">ECHA InfoCard</a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.311">100.000.311</a> <a href="https://www.wikidata.org/wiki/Q415563#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data">C20H24O2</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data">296.410 g·mol−1</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=Oc1cc4c%28cc1%29%5BC%40H%5D3CC%5BC%40%5D2%28%5BC%40%40H%5D%28CC%5BC%40%5D2%28C%23C%29O%29%5BC%40%40H%5D3CC4%29C">Interactive image</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Melting_point" title="Melting point">Melting point</a></th><td class="infobox-data">182 to 184 °C (360 to 363 °F)</td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Oc1cc4c(cc1)[C@H]3CC[C@]2([C@@H](CC[C@]2(C#C)O)[C@@H]3CC4)C</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">InChI=1S/C20H24O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,5,7,12,16-18,21-22H,4,6,8-11H2,2H3/t16-,17-,18+,19+,20+/m1/s1 <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</div></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:BFPYWIDHMRZLRN-SLHNCBLASA-N <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-below"><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style>  <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=458286647&page2=Ethinylestradiol">(verify)</a></td></tr></tbody></table> Ethinylestradiol (EE) is an <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogen</a> medication which is used widely in <a href="/wiki/Birth_control_pills" class="mw-redirect" title="Birth control pills">birth control pills</a> in combination with <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestins</a>.<a href="#cite_note-pmid16112947-7">[7]</a><a href="#cite_note-OettelSchillinger2012-8">[8]</a> In the past, EE was widely used for various indications such as the treatment of <a href="/wiki/Menopause" title="Menopause">menopausal</a> <a href="/wiki/Symptom" class="mw-redirect" title="Symptom">symptoms</a>, <a href="/wiki/Gynecological_disorder" class="mw-redirect" title="Gynecological disorder">gynecological disorders</a>, and certain <a href="/wiki/Hormone-sensitive_cancer" title="Hormone-sensitive cancer">hormone-sensitive cancers</a>. It is usually taken <a href="/wiki/Oral_administration" title="Oral administration">by mouth</a> but is also used as a <a href="/wiki/Transdermal_patch" title="Transdermal patch">patch</a> and <a href="/wiki/Vaginal_ring" title="Vaginal ring">vaginal ring</a>.<a href="#cite_note-pmid16112947-7">[7]</a><a href="#cite_note-Drugs@FDA-12">[12]</a> The general <a href="/wiki/Side_effect" title="Side effect">side effects</a> of EE include <a href="/wiki/Breast_tenderness" class="mw-redirect" title="Breast tenderness">breast tenderness</a> and <a href="/wiki/Breast_enlargement" title="Breast enlargement">enlargement</a>, <a href="/wiki/Headache" title="Headache">headache</a>, <a href="/wiki/Water_retention_(medicine)" class="mw-redirect" title="Water retention (medicine)">fluid retention</a>, and <a href="/wiki/Nausea" title="Nausea">nausea</a> among others.<a href="#cite_note-pmid16112947-7">[7]</a> In men, EE can additionally cause <a href="/wiki/Gynecomastia" title="Gynecomastia">breast development</a>, <a href="/wiki/Feminization_(biology)" title="Feminization (biology)">feminization</a> in general, <a href="/wiki/Hypogonadism" title="Hypogonadism">hypogonadism</a>, and <a href="/wiki/Sexual_dysfunction" title="Sexual dysfunction">sexual dysfunction</a>. Rare but serious side effects include <a href="/wiki/Blood_clot" class="mw-redirect" title="Blood clot">blood clots</a>, <a href="/wiki/Liver_damage" class="mw-redirect" title="Liver damage">liver damage</a>, and <a href="/wiki/Endometrial_cancer" title="Endometrial cancer">cancer of the uterus</a>.<a href="#cite_note-pmid16112947-7">[7]</a> EE is an <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogen</a>, or an <a href="/wiki/Agonist" title="Agonist">agonist</a> of the <a href="/wiki/Estrogen_receptor" title="Estrogen receptor">estrogen receptors</a>, the <a href="/wiki/Biological_target" title="Biological target">biological target</a> of estrogens like <a href="/wiki/Estradiol" title="Estradiol">estradiol</a>.<a href="#cite_note-pmid16112947-7">[7]</a> It is a <a href="/wiki/Synthetic_compound" class="mw-redirect" title="Synthetic compound">synthetic</a> <a href="/wiki/Chemical_derivative" class="mw-redirect" title="Chemical derivative">derivative</a> of <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a>, a <a href="/wiki/Natural_product" title="Natural product">natural</a> estrogen, and differs from it in various ways.<a href="#cite_note-pmid16112947-7">[7]</a> Compared to estradiol, EE is more resistant to <a href="/wiki/Metabolism" title="Metabolism">metabolism</a>, has greatly improved <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> when taken by mouth, and shows relatively increased effects in certain parts of the body like the <a href="/wiki/Liver" title="Liver">liver</a> and <a href="/wiki/Uterus" title="Uterus">uterus</a>.<a href="#cite_note-pmid16112947-7">[7]</a> These differences make EE more favorable for use in birth control pills than estradiol, though also result in an increased risk of blood clots and certain other rare adverse effects.<a href="#cite_note-pmid16112947-7">[7]</a> EE was developed in the 1930s and was introduced for medical use in 1943.<a href="#cite_note-Fis2006-13">[13]</a><a href="#cite_note-Estinyl_1943-14">[14]</a> The medication started being used in birth control pills in the 1960s.<a href="#cite_note-GruhnKazer2013-15">[15]</a> Ethinylestradiol is found in almost all <a href="/wiki/Combined_oral_contraceptive_pill" title="Combined oral contraceptive pill">combined</a> forms of birth control pills and is nearly the exclusive estrogen used for this purpose, making it one of the most widely used estrogens.<a href="#cite_note-pmid25841596-16">[16]</a><a href="#cite_note-ShoupeHaseltine2012-17">[17]</a> The combination with <a href="/wiki/Norethisterone" title="Norethisterone">norethisterone</a> was already the 80th most commonly prescribed medication in the United States and the compound appears in many other common mediactions as well.;<a href="#cite_note-Top_300_of_2022-18">[18]</a><a href="#cite_note-E+N-19">[19]</a> <style data-mw-deduplicate="TemplateStyles:r886046785">.mw-parser-output .toclimit-2 .toclevel-1 ul,.mw-parser-output .toclimit-3 .toclevel-2 ul,.mw-parser-output .toclimit-4 .toclevel-3 ul,.mw-parser-output .toclimit-5 .toclevel-4 ul,.mw-parser-output .toclimit-6 .toclevel-5 ul,.mw-parser-output .toclimit-7 .toclevel-6 ul{display:none}</style><div class="toclimit-3"><meta property="mw:PageProp/toc" /></div> <div class="mw-heading mw-heading2"><h2 id="Medical_uses">Medical uses</h2>[<a href="/w/index.php?title=Ethinylestradiol&action=edit&section=1" title="Edit section: Medical uses">edit</a>]</div> There are many uses for EE. It is most commonly used as <a href="/wiki/Contraception" class="mw-redirect" title="Contraception">contraception</a> in <a href="/wiki/Combined_oral_contraceptives" class="mw-redirect" title="Combined oral contraceptives">combined oral contraceptives</a> (COC), also known as <a href="/wiki/Birth_control" title="Birth control">birth control</a>, to prevent pregnancy after sex. EE in its birth control formulation is not only used to prevent pregnancy, but can also be used to treat absence of menstruation, symptoms during menstruation, and <a href="/wiki/Acne" title="Acne">acne</a>. EE is also used as <a href="/wiki/Menopausal_hormone_therapy" class="mw-redirect" title="Menopausal hormone therapy">menopausal hormone therapy</a>.<a href="#cite_note-pmid16860174-20">[20]</a> The main reason for using HRT in menopausal women is to relieve common <a href="/wiki/Vasomotor_symptoms" class="mw-redirect" title="Vasomotor symptoms">vasomotor symptoms</a> such as <a href="/wiki/Hot_flashes" class="mw-redirect" title="Hot flashes">hot flashes</a>, <a href="/wiki/Night_sweats" title="Night sweats">night sweats</a>, and <a href="/wiki/Flushing_(physiology)" title="Flushing (physiology)">flushing</a>. Studies have found that estrogen replacement helps improve these symptoms when compared to a placebo.<a href="#cite_note-21">[21]</a> Other common menopause symptoms, such as vaginal dryness (which can cause pain during sexual intercourse), vaginal itching, and depressed mood, can benefit from HRT. In addition to treatment of menopausal symptoms, EE has been used as a component of <a href="/wiki/Feminizing_hormone_therapy" title="Feminizing hormone therapy">feminizing hormone therapy</a> for <a href="/wiki/Transgender_women" class="mw-redirect" title="Transgender women">transgender women</a>.<a href="#cite_note-pmid28078219-22">[22]</a> However, it is no longer commonly used nor recommended for this purpose, with <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a> having largely superseded it.<a href="#cite_note-pmid28078219-22">[22]</a> EE can also be used to treat <a href="/wiki/Hypogonadism" title="Hypogonadism">hypogonadism</a> in women, prevent osteoporosis in women, and has been used as <a href="/wiki/Palliative_care" title="Palliative care">palliative care</a> for <a href="/wiki/Prostate_cancer" title="Prostate cancer">prostate cancer</a> in men and <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a> in women.<a href="#cite_note-OettelSchillinger2012-8">[8]</a><a href="#cite_note-pmid27889048a-23">[23]</a> It has also been used to reduce <a href="/wiki/Sex_drive" class="mw-redirect" title="Sex drive">sex drive</a> in <a href="/wiki/Sex_offender" title="Sex offender">sex offenders</a>.<a href="#cite_note-pmid20459370-24">[24]</a><a href="#cite_note-pmid4607733-25">[25]</a> EE or any estrogen alone is contraindicated for women who have a uterus due to the increased risk of <a href="/wiki/Endometrial_cancer" title="Endometrial cancer">endometrial cancer</a>; giving a <a href="/wiki/Progestogen_(medication)" title="Progestogen (medication)">progestogen</a> with an estrogen mitigates the risk.<a href="#cite_note-ACS2015-26">[26]</a> <div class="mw-heading mw-heading3"><h3 id="Available_forms">Available forms</h3>[<a href="/w/index.php?title=Ethinylestradiol&action=edit&section=2" title="Edit section: Available forms">edit</a>]</div> EE is available in combination with a progestin in a vast number of COCs.<a href="#cite_note-HumansOrganization2007-27">[27]</a> It is also available in combination with progestins as a <a href="/wiki/Transdermal_administration" class="mw-redirect" title="Transdermal administration">transdermal</a> <a href="/wiki/Contraceptive_patch" title="Contraceptive patch">contraceptive patch</a> and as a <a href="/wiki/Contraceptive_vaginal_ring" title="Contraceptive vaginal ring">contraceptive vaginal ring</a>.<a href="#cite_note-Drugs@FDA-12">[12]</a> In addition, there is a single preparation (brand name FemHRT) containing very low doses of EE (2.5 and 5 μg) plus a progestin in an oral <a href="/wiki/Tablet_(pharmacy)" title="Tablet (pharmacy)">tablet</a> that remains in use for menopausal hormone therapy.<a href="#cite_note-Drugs@FDA-12">[12]</a><a href="#cite_note-pmid16860174-20">[20]</a> EE was previously available by itself under brand names like Estinyl and Lynoral in the form of 0.002, 0.01, 0.02, 0.025, 0.05, 0.1, 0.5, and 1.0 mg (2, 10, 20, 25, 50, 100, 500, and 1000 μg) tablets.<a href="#cite_note-Becker2001-28">[28]</a><a href="#cite_note-DIANE1995-29">[29]</a><a href="#cite_note-U.S._Department_of_Health_and_Human_Services,_Public_Health_Service,_Food_and_Drug_Administration,_Bureau_of_Drugs1980-30">[30]</a><a href="#cite_note-Muller1998-31">[31]</a><a href="#cite_note-MonfardiniBrunnerCrowther2012-32">[32]</a> The amount of EE in COCs has reduced over the years.<a href="#cite_note-OettelSchillinger2012-8">[8]</a> Previously, COCs contained high doses of EE of as much as 100 μg/day.<a href="#cite_note-LipHall2007-33">[33]</a> Doses of more than 50 μg EE are considered high-dose, doses of 30 and 35 μg EE are considered low-dose, and doses of 10 to 25 μg EE are considered very low dose.<a href="#cite_note-AlldredgeCorelli2012-34">[34]</a> Today, COCs generally contain 10 to 50 μg EE.<a href="#cite_note-AlldredgeCorelli2012-34">[34]</a> The higher doses of EE were discontinued due to a high risk of VTE and cardiovascular problems.<a href="#cite_note-LipHall2007-33">[33]</a> <div class="mw-heading mw-heading2"><h2 id="Contraindications">Contraindications</h2>[<a href="/w/index.php?title=Ethinylestradiol&action=edit&section=3" title="Edit section: Contraindications">edit</a>]</div> EE should be avoided in individuals with a history of or known susceptibility to <a href="/wiki/Arterial_thrombosis" class="mw-redirect" title="Arterial thrombosis">arterial</a> or <a href="/wiki/Venous_thrombosis" title="Venous thrombosis">venous thrombosis</a> (<a href="/wiki/Blood_clots" class="mw-redirect" title="Blood clots">blood clots</a>), due to an increased risk of <a href="/wiki/Cardiovascular" class="mw-redirect" title="Cardiovascular">cardiovascular</a> problems such as <a href="/wiki/Venous_thromboembolism" class="mw-redirect" title="Venous thromboembolism">venous thromboembolism</a> (VTE), <a href="/wiki/Myocardial_infarction" title="Myocardial infarction">myocardial infarction</a>, and <a href="/wiki/Ischemic_stroke" class="mw-redirect" title="Ischemic stroke">ischemic stroke</a>.<a href="#cite_note-35">[35]</a> This includes women with: <ul><li>History of <a href="/wiki/Deep_vein_thrombosis" title="Deep vein thrombosis">deep vein thrombosis</a> (DVT) or <a href="/wiki/Pulmonary_embolism" title="Pulmonary embolism">pulmonary embolism</a> (PE) not receiving <a href="/wiki/Anticoagulants" class="mw-redirect" title="Anticoagulants">anticoagulants</a></li> <li>Acute DVT/PE</li> <li>Prolonged immobilization due to major surgery</li> <li>Advanced <a href="/wiki/Diabetes_mellitus" class="mw-redirect" title="Diabetes mellitus">diabetes mellitus</a> with vascular disease</li> <li><a href="/wiki/Migraine_with_aura" class="mw-redirect" title="Migraine with aura">Migraine with aura</a></li> <li><a href="/wiki/Hypertension" title="Hypertension">Hypertension</a> ≥160/100</li> <li><a href="/wiki/Vascular_disease" title="Vascular disease">Vascular disease</a></li> <li>Current and history of <a href="/wiki/Ischemic_heart_disease" class="mw-redirect" title="Ischemic heart disease">ischemic heart disease</a></li> <li>Multiple risk factors for <a href="/wiki/Atherosclerotic_cardiovascular_disease" class="mw-redirect" title="Atherosclerotic cardiovascular disease">atherosclerotic cardiovascular disease</a> (e.g. older age, smoking, diabetes, hypertension, low HDL, high LDL, or high triglyceride levels)</li> <li>Age ≥35 and smoking ≥15 cigarettes/day</li> <li>History of <a href="/wiki/Cerebrovascular_accident" class="mw-redirect" title="Cerebrovascular accident">cerebrovascular accident</a></li> <li>Systemic <a href="/wiki/Lupus_erythematosus" title="Lupus erythematosus">lupus erythematosus</a> with positive (or unknown) antiphospholipid antibodies</li> <li>Complicated <a href="/wiki/Valvular_heart_disease" title="Valvular heart disease">valvular heart disease</a></li></ul> Except when being used to treat it, EE should be avoided in women with current <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a> due to a possible worsening of prognosis.<a href="#cite_note-CDC2016-36">[36]</a> EE should also be avoided in <a href="/wiki/Breastfeeding" title="Breastfeeding">breastfeeding</a> women who are less than 21 days <a href="/wiki/Postpartum" class="mw-redirect" title="Postpartum">postpartum</a> due to an increased risk of VTE.<a href="#cite_note-cdc.gov-37">[37]</a> EE use in breastfeeding women who are at least 21 days postpartum should be discussed with a provider and include information on the advantages, disadvantages, and alternatives for using EE.<a href="#cite_note-cdc.gov-37">[37]</a> Due to risk of <a href="/wiki/Cholestatic_hepatotoxicity" class="mw-redirect" title="Cholestatic hepatotoxicity">cholestatic hepatotoxicity</a>, it is widely considered that COCs containing EE should be avoided in women with a history of <a href="/wiki/Cholestasis_of_pregnancy" class="mw-redirect" title="Cholestasis of pregnancy">cholestasis of pregnancy</a>, <a href="/wiki/Hepatic_tumor" class="mw-redirect" title="Hepatic tumor">hepatic tumors</a>, active <a href="/wiki/Hepatitis" title="Hepatitis">hepatitis</a>, and familial defects in biliary excretion.<a href="#cite_note-Aronson2009-38">[38]</a> <div class="mw-heading mw-heading2"><h2 id="Side_effects">Side effects</h2>[<a href="/w/index.php?title=Ethinylestradiol&action=edit&section=4" title="Edit section: Side effects">edit</a>]</div> <table class="wikitable floatright" style="margin: 1em auto;"> <caption class="nowrap">Dose of ethinylestradiol in <a href="/wiki/Birth_control_pill" class="mw-redirect" title="Birth control pill">birth control pills</a> and risk of <a href="/wiki/Venous_thromboembolism" class="mw-redirect" title="Venous thromboembolism">venous thromboembolism</a> (VTE) </caption> <tbody><tr> <th>Ethinylestradiol dose</th> <th>No. of VTE cases</th> <th>Woman-years</th> <th>VTE rate</th> <th>Adjusted <abbr title="relative risk">RR</abbr>a </th></tr> <tr> <td>Low (<50 μg)</td> <td>53</td> <td>127,000</td> <td>4.2 in 10,000 woman-years</td> <td>1.0 </td></tr> <tr> <td>Intermediate (50 μg)</td> <td>69</td> <td>98,000</td> <td>7.0 in 10,000 woman-years</td> <td>1.5 </td></tr> <tr> <td>High (>50 μg)</td> <td>20</td> <td>20,000</td> <td>10.0 in 10,000 woman-years</td> <td>1.7 </td></tr> <tr> <td>All</td> <td>142</td> <td>245,000</td> <td>5.8 in 10,000 woman-years</td> <td>– </td></tr> <tr class="sortbottom"> <td colspan="5" style="width: 1px; background-color:#eaecf0; text-align: center;">Footnotes: a = Relative to low-dose (not to non-use). Notes: In birth control pills containing a <a href="/wiki/First-generation_progestin" class="mw-redirect" title="First-generation progestin">first-generation progestin</a>, such as <a href="/wiki/Norethisterone" title="Norethisterone">norethisterone</a> or <a href="/wiki/Levonorgestrel" title="Levonorgestrel">levonorgestrel</a>. Sources: Main:<a href="#cite_note-pmid1983896-39">[39]</a><a href="#cite_note-RunnebaumRabe2013-40">[40]</a> Additional:<a href="#cite_note-pmid1983923-41">[41]</a> </td></tr></tbody></table> The severity of side effects can vary based on the dose and administration route of EE.<a href="#cite_note-42">[42]</a> General side effects of EE are the same as for other estrogens and include <a href="/wiki/Breast_tenderness" class="mw-redirect" title="Breast tenderness">breast tenderness</a>, <a href="/wiki/Headache" title="Headache">headache</a>, <a href="/wiki/Water_retention_(medicine)" class="mw-redirect" title="Water retention (medicine)">fluid retention</a> (<a href="/wiki/Bloating" title="Bloating">bloating</a>), <a href="/wiki/Nausea" title="Nausea">nausea</a>, <a href="/wiki/Dizziness" title="Dizziness">dizziness</a>, and <a href="/wiki/Weight_gain" title="Weight gain">weight gain</a>.<a href="#cite_note-pmid23375353-10">[10]</a><a href="#cite_note-Aronson2009-38">[38]</a> The estrogen component of oral contraceptives, which is almost always EE, can cause <a href="/wiki/Breast_tenderness" class="mw-redirect" title="Breast tenderness">breast tenderness</a> and <a href="/wiki/Breast_enlargement" title="Breast enlargement">fullness</a>.<a href="#cite_note-Becker2001-28">[28]</a> In males, EE has additional side effects, including <a href="/wiki/Gynecomastia" title="Gynecomastia">gynecomastia</a> (breast development), <a href="/wiki/Feminization_(biology)" title="Feminization (biology)">feminization</a> in general, <a href="/wiki/Hypogonadism" title="Hypogonadism">hypogonadism</a>, <a href="/wiki/Infertility" title="Infertility">infertility</a>, and <a href="/wiki/Sexual_dysfunction" title="Sexual dysfunction">sexual dysfunction</a> (e.g., reduced <a href="/wiki/Libido" title="Libido">libido</a> and <a href="/wiki/Erectile_dysfunction" title="Erectile dysfunction">erectile dysfunction</a>). In men who received <a href="/wiki/High-dose_estrogen" class="mw-redirect" title="High-dose estrogen">high-dose estrogen</a> therapy with 200 μg/day oral EE for more than three months, gynecomastia occurred in 98% and decreased libido occurred in 42 to 73%.<a href="#cite_note-Pincus2013-43">[43]</a> <div class="mw-heading mw-heading3"><h3 id="Long-term_effects">Long-term effects</h3>[<a href="/w/index.php?title=Ethinylestradiol&action=edit&section=5" title="Edit section: Long-term effects">edit</a>]</div> <table class="wikitable sortable floatright" style="text-align:left; border:none;"> <caption class="nowrap">Beneficial and adverse effects of ethinylestradiol-containing birth control pills </caption> <tbody><tr> <th colspan="2"><a href="/wiki/Therapeutic_effect" title="Therapeutic effect">Beneficial effects</a></th> <th colspan="2"><a href="/wiki/Adverse_effect" title="Adverse effect">Adverse effects</a> </th></tr> <tr> <th><a href="/wiki/Disease" title="Disease">Disease</a></th> <th><a href="/wiki/Relative_risk" title="Relative risk"><abbr title="Relative risk">RR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Relative risk</th> <th><a href="/wiki/Disease" title="Disease">Disease</a></th> <th><a href="/wiki/Relative_risk" title="Relative risk"><abbr title="Relative risk">RR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Relative risk </th></tr> <tr> <td><a href="/wiki/Iron-deficiency_anemia" title="Iron-deficiency anemia">Iron-deficiency anemia</a></td> <td>0.58</td> <td><a href="/wiki/Cardiovascular_disease" title="Cardiovascular disease">Cardiovascular diseases</a> (total)</td> <td>1.5 </td></tr> <tr> <td><a href="/wiki/Menorrhagia" class="mw-redirect" title="Menorrhagia">Menorrhagia</a></td> <td>0.52</td> <td><a href="/wiki/Myocardial_infarction" title="Myocardial infarction">Myocardial infarction</a> (heart attack) (total)</td> <td>3.3 </td></tr> <tr> <td><a href="/wiki/Irregular_menstruation" title="Irregular menstruation">Irregular menstruation</a></td> <td>0.65</td> <td><a href="/wiki/Myocardial_infarction" title="Myocardial infarction">Myocardial infarction</a> (non-<a href="/wiki/Smoking" title="Smoking">smokers</a>)</td> <td>1.0 </td></tr> <tr> <td><a href="/wiki/Breakthrough_bleeding" class="mw-redirect" title="Breakthrough bleeding">Intermenstrual bleeding</a></td> <td>0.72</td> <td><a href="/wiki/Myocardial_infarction" title="Myocardial infarction">Myocardial infarction</a> (light <a href="/wiki/Smoking" title="Smoking">smokers</a>)</td> <td>3.5 </td></tr> <tr> <td><a href="/wiki/Dysmenorrhea" title="Dysmenorrhea">Dysmenorrhea</a></td> <td>0.37</td> <td><a href="/wiki/Myocardial_infarction" title="Myocardial infarction">Myocardial infarction</a> (heavy <a href="/wiki/Smoking" title="Smoking">smokers</a>)</td> <td>20 </td></tr> <tr> <td><a href="/wiki/Pelvic_inflammatory_disease" title="Pelvic inflammatory disease">Pelvic inflammatory disease</a> (incidence)</td> <td>0.50</td> <td><a href="/wiki/Cerebrovascular_disease" title="Cerebrovascular disease">Cerebrovascular diseases</a> (total)</td> <td>1.4 </td></tr> <tr> <td><a href="/wiki/Pelvic_inflammatory_disease" title="Pelvic inflammatory disease">Pelvic inflammatory disease</a> (<a href="/wiki/Hospitalization" class="mw-redirect" title="Hospitalization">hospitalization</a>)</td> <td>0.22</td> <td><a href="/wiki/Cerebral_thrombosis" class="mw-redirect" title="Cerebral thrombosis">Cerebral thromboses</a> (strokes)</td> <td>2.5 </td></tr> <tr> <td><a href="/wiki/Trichomonas_vaginitis" class="mw-redirect" title="Trichomonas vaginitis">Trichomonas vaginitis</a></td> <td>0.56</td> <td><a href="/wiki/Subarachnoidal_bleeding" class="mw-redirect" title="Subarachnoidal bleeding">Subarachnoidal bleeding</a> (heavy <a href="/wiki/Smoking" title="Smoking">smokers</a>)</td> <td>10 </td></tr> <tr> <td><a href="/wiki/Benign_breast_disease" class="mw-redirect" title="Benign breast disease">Benign breast disease</a></td> <td>0.69</td> <td><a href="/wiki/Pulmonary_embolism" title="Pulmonary embolism">Pulmonary embolism</a></td> <td>3.0 </td></tr> <tr> <td><a href="/wiki/Fibrocystic_breast_disease" class="mw-redirect" title="Fibrocystic breast disease">Fibrocystic breast disease</a></td> <td>0.66</td> <td><a href="/wiki/Deep_vein_thrombosis" title="Deep vein thrombosis">Deep vein thromboses</a></td> <td>2.5 </td></tr> <tr> <td><a href="/wiki/Benign_breast_fibroadenomas" class="mw-redirect" title="Benign breast fibroadenomas">Benign breast fibroadenomas</a></td> <td>0.35</td> <td><a href="/wiki/Gall_bladder_disease" class="mw-redirect" title="Gall bladder disease">Gall-bladder diseases</a></td> <td>3.0 </td></tr> <tr> <td><a href="/wiki/Rheumatoid_arthritis" title="Rheumatoid arthritis">Rheumatoid arthritis</a></td> <td>0.49</td> <td><a href="/wiki/Benign_liver_tumor" class="mw-redirect" title="Benign liver tumor">Benign liver tumors</a></td> <td>50 </td></tr> <tr> <td><a href="/wiki/Endometrial_cancer" title="Endometrial cancer">Endometrial cancer</a></td> <td>0.40–0.50</td> <td><a href="/wiki/Hepatocellular_carcinoma" title="Hepatocellular carcinoma">Hepatocellular carcinoma</a></td> <td>3.0 </td></tr> <tr> <td><a href="/wiki/Ovarian_cancer" title="Ovarian cancer">Ovarian cancer</a> (incidence)</td> <td>0.37–0.64</td> <td><a href="/wiki/Erythema_nodosum_et_multiforme" title="Erythema nodosum et multiforme">Erythema nodosum et multiforme</a></td> <td>3.0 </td></tr> <tr> <td><a href="/wiki/Ovarian_cancer" title="Ovarian cancer">Ovarian cancer</a> (death)</td> <td>0.20</td> <td><a href="/wiki/Pruritus" class="mw-redirect" title="Pruritus">Pruritus</a> (itching)</td> <td>2.0 </td></tr> <tr> <td><a href="/wiki/Follicular_cyst_of_ovary" title="Follicular cyst of ovary">Benign follicular cysts</a> (high-dose COCs)</td> <td>0.24</td> <td><a href="/wiki/Photosensitive_eczema" class="mw-redirect" title="Photosensitive eczema">Photosensitive eczema</a></td> <td>4.0 </td></tr> <tr> <td><a href="/wiki/Acne_vulgaris" class="mw-redirect" title="Acne vulgaris">Acne vulgaris</a></td> <td>0.44</td> <td><a href="/wiki/Irritant_agent_eczema" class="mw-redirect" title="Irritant agent eczema">Irritant agent eczema</a></td> <td>2.0 </td></tr> <tr> <td><a href="/wiki/Low_bone_mineral_density" class="mw-redirect" title="Low bone mineral density">Low bone mineral density</a> (later in life)</td> <td>0.35a</td> <td><a href="/wiki/Dermatitis" title="Dermatitis">Dermatitis</a> (eczema)</td> <td>2.0 </td></tr> <tr> <td><a href="/wiki/Ectopic_pregnancy" title="Ectopic pregnancy">Ectopic pregnancy</a></td> <td>0.19</td> <td><a href="/wiki/Chloasma" class="mw-redirect" title="Chloasma">Chloasma</a> (melasma)</td> <td>1.5 </td></tr> <tr> <td></td> <td></td> <td><a href="/wiki/Cervicitis" title="Cervicitis">Cervicitis</a> (6 years of use)</td> <td>3.0 </td></tr> <tr> <td></td> <td></td> <td><a href="/wiki/Chlamydia_infection" class="mw-redirect" title="Chlamydia infection">Chlamydia infections</a></td> <td>2.5 </td></tr> <tr class="sortbottom"> <td colspan="4" style="width: 1px; background-color:#eaecf0; text-align: center;">Footnotes: a = <a href="/wiki/Odds_ratio" title="Odds ratio">Odds ratio</a>. Sources: <a href="#cite_note-OettelSchillinger2012b-44">[44]</a><a href="#cite_note-Becker2001-28">[28]</a> </td></tr></tbody></table> <div class="mw-heading mw-heading4"><h4 id="Blood_clots">Blood clots</h4>[<a href="/w/index.php?title=Ethinylestradiol&action=edit&section=6" title="Edit section: Blood clots">edit</a>]</div> VTE is a <a href="/wiki/Blood_clot" class="mw-redirect" title="Blood clot">blood clot</a> in a <a href="/wiki/Vein" title="Vein">vein</a>, and includes <a href="/wiki/Deep_vein_thrombosis" title="Deep vein thrombosis">deep vein thrombosis</a> (DVT) and <a href="/wiki/Pulmonary_embolism" title="Pulmonary embolism">pulmonary embolism</a> (PE).<a href="#cite_note-pmid16112947-7">[7]</a><a href="#cite_note-Legato2009-45">[45]</a><a href="#cite_note-Stein2016-46">[46]</a> Estrogens are known to increase the risk of VTE due to their effects on <a href="/wiki/Liver_protein_synthesis" class="mw-redirect" title="Liver protein synthesis">liver synthesis</a> of <a href="/wiki/Coagulation_factor" class="mw-redirect" title="Coagulation factor">coagulation factors</a>.<a href="#cite_note-pmid16112947-7">[7]</a><a href="#cite_note-Legato2009-45">[45]</a><a href="#cite_note-Stein2016-46">[46]</a> EE carries a greater risk of blood clot formation and VTE than does natural <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a>, which is thought to be due to <a href="/wiki/Chemical_structure" title="Chemical structure">structural</a> differences between the two compounds and different susceptibilities to <a href="/wiki/Liver" title="Liver">liver</a> <a href="/wiki/Metabolism" title="Metabolism">inactivation</a>.<a href="#cite_note-pmid16112947-7">[7]</a> A 2012 <a href="/wiki/Meta-analysis" title="Meta-analysis">meta-analysis</a> estimated that the <a href="/wiki/Absolute_risk" title="Absolute risk">absolute risk</a> of VTE is 2 per 10,000 women for non-use, 8 per 10,000 women for EE and <a href="/wiki/Levonorgestrel" title="Levonorgestrel">levonorgestrel</a>-containing birth control pills, and 10 to 15 per 10,000 women for birth control pills containing EE and a <a href="/wiki/Third-generation_progestin" class="mw-redirect" title="Third-generation progestin">third-</a> or <a href="/wiki/Fourth-generation_progestin" class="mw-redirect" title="Fourth-generation progestin">fourth-generation progestin</a> such as <a href="/wiki/Desogestrel" title="Desogestrel">desogestrel</a> or <a href="/wiki/Drospirenone" title="Drospirenone">drospirenone</a>.<a href="#cite_note-pmid27793376-47">[47]</a> For comparison, the absolute risk of VTE is generally estimated as 1 to 5 per 10,000 woman–years for non-use, 5 to 20 per 10,000 woman–years for pregnancy, and 40 to 65 per 10,000 woman–years for the <a href="/wiki/Postpartum" class="mw-redirect" title="Postpartum">postpartum</a> period.<a href="#cite_note-pmid27793376-47">[47]</a> Modern COCs are associated with about a 2- to 4-fold higher risk of VTE than non-use.<a href="#cite_note-pmid27793376-47">[47]</a> The <a href="/wiki/Route_of_administration" title="Route of administration">route of administration</a> of EE does not appear to influence VTE risk, as EE/progestin-containing <a href="/wiki/Contraceptive_vaginal_ring" title="Contraceptive vaginal ring">contraceptive vaginal rings</a> and <a href="/wiki/Contraceptive_patch" title="Contraceptive patch">contraceptive patches</a> have the same or even higher risk of VTE than COCs.<a href="#cite_note-pmid27793376-47">[47]</a><a href="#cite_note-pmid23384743-48">[48]</a> Pregnancy is associated with about a 4.3-fold increase in risk of VTE.<a href="#cite_note-pmid27793376-47">[47]</a> It has been estimated that at least 300 to 400 healthy young women die each year in the United States due to VTE caused by EE-containing birth control pills.<a href="#cite_note-KeenanKerr2019-49">[49]</a> Modern COCs contain 10 to 35 μg EE, but typically 20, 30, or 35 μg.<a href="#cite_note-pmid27793376-47">[47]</a><a href="#cite_note-FalconeHurd2007-50">[50]</a> The initial formulations of COCs that were introduced in the 1960s contained 100 to 150 μg EE.<a href="#cite_note-pmid28376481-51">[51]</a><a href="#cite_note-pmid1983923-41">[41]</a><a href="#cite_note-FalconeHurd2007-50">[50]</a> However, it was soon found that EE is associated with increased risk of VTE and that the risk is dose-dependent.<a href="#cite_note-FalconeHurd2007-50">[50]</a> Following these events, the dose of EE was greatly reduced, and is now always less than 50 μg.<a href="#cite_note-Becker2001b-52">[52]</a><a href="#cite_note-BreastCancer1991-53">[53]</a><a href="#cite_note-DIANE-54">[54]</a> These lower doses have a significantly reduced risk of VTE with no loss of contraceptive effectiveness.<a href="#cite_note-FalconeHurd2007-50">[50]</a> Gerstman et al. (1991) found that COCs containing more than 50 μg EE had 1.7-fold and COCs containing 50 μg EE 1.5-fold the risk of VTE of COCs containing less than 50 μg.<a href="#cite_note-pmid1983896-39">[39]</a> A 2014 <a href="/wiki/Cochrane_(organization)" class="mw-redirect" title="Cochrane (organization)">Cochrane</a> review found that COCs containing 50 μg EE with levonorgestrel had 2.1- to 2.3-fold the risk of COCs containing 30 μg or 20 μg EE with levonorgestrel, respectively.<a href="#cite_note-pmid27793376-47">[47]</a> COCs containing 20 μg EE are likewise associated with a significantly lower risk of cardiovascular events than COCs containing 30 or 40 μg EE.<a href="#cite_note-pmid27678035-55">[55]</a> However, discontinuation of COCs is more common with doses of EE from 10 to 20 μg due to problematic changes in bleeding patterns.<a href="#cite_note-pmid23904209-56">[56]</a> Women with <a href="/wiki/Thrombophilia" title="Thrombophilia">thrombophilia</a> have a dramatically higher risk of VTE with EE-containing contraception than women without thrombophilia.<a href="#cite_note-pmid27793376-47">[47]</a><a href="#cite_note-pmid23384743-48">[48]</a> Depending on the condition, risk of VTE can be increased 5- to 50-fold relative to non-use in such women.<a href="#cite_note-pmid27793376-47">[47]</a><a href="#cite_note-pmid23384743-48">[48]</a> <a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin">Sex hormone-binding globulin</a> (SHBG) levels indicate hepatic estrogenic exposure and may be a <a href="/wiki/Surrogate_marker" class="mw-redirect" title="Surrogate marker">surrogate marker</a> for <a href="/wiki/Coagulation" title="Coagulation">coagulation</a> and VTE risk with estrogen therapy, although this topic has been debated.<a href="#cite_note-pmid12047300-57">[57]</a><a href="#cite_note-pmid22469296-58">[58]</a><a href="#cite_note-pmid18692609-59">[59]</a> SHBG levels with birth control pills containing different progestins are increased by 1.5 to 2-fold with <a href="/wiki/Levonorgestrel" title="Levonorgestrel">levonorgestrel</a>, 2.5- to 4-fold with <a href="/wiki/Desogestrel" title="Desogestrel">desogestrel</a> and <a href="/wiki/Gestodene" title="Gestodene">gestodene</a>, 3.5- to 4-fold with <a href="/wiki/Drospirenone" title="Drospirenone">drospirenone</a> and <a href="/wiki/Dienogest" title="Dienogest">dienogest</a>, and 4- to 5-fold with <a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">cyproterone acetate</a>.<a href="#cite_note-pmid12047300-57">[57]</a> <a href="/wiki/Contraceptive_vaginal_ring" title="Contraceptive vaginal ring">Contraceptive vaginal rings</a> and <a href="/wiki/Contraceptive_patch" title="Contraceptive patch">contraceptive patches</a> likewise have been found to increase SHBG levels by 2.5-fold and 3.5-fold, respectively.<a href="#cite_note-pmid12047300-57">[57]</a> Birth control pills containing high doses of ethinylestradiol (>50 μg) can increase SHBG levels by 5- to 10-fold, which is similar to the increase that occurs during pregnancy.<a href="#cite_note-WintersHuhtaniemi2017-60">[60]</a> Conversely, increases in SHBG levels are much lower with <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a>, especially when used parenterally.<a href="#cite_note-pmid16915215-61">[61]</a><a href="#cite_note-pmid22011208-62">[62]</a><a href="#cite_note-pmid3242384-63">[63]</a><a href="#cite_note-pmid2664738-64">[64]</a><a href="#cite_note-pmid3817605-65">[65]</a> High-dose parenteral <a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">polyestradiol phosphate</a> therapy has been found to increase SHBG levels by about 1.5-fold.<a href="#cite_note-pmid2664738-64">[64]</a> <table class="wikitable sortable mw-collapsible mw-collapsed" style="margin: 1em auto;"> <caption class="nowrap"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul ul{display:inline}.mw-parser-output .hlist .mw-empty-li{display:none}.mw-parser-output .hlist dt::after{content:": "}.mw-parser-output .hlist dd::after,.mw-parser-output .hlist li::after{content:" · ";font-weight:bold}.mw-parser-output .hlist dd:last-child::after,.mw-parser-output .hlist dt:last-child::after,.mw-parser-output .hlist li:last-child::after{content:none}.mw-parser-output .hlist dd dd:first-child::before,.mw-parser-output .hlist dd dt:first-child::before,.mw-parser-output .hlist dd li:first-child::before,.mw-parser-output .hlist dt dd:first-child::before,.mw-parser-output .hlist dt dt:first-child::before,.mw-parser-output .hlist dt li:first-child::before,.mw-parser-output .hlist li dd:first-child::before,.mw-parser-output .hlist li dt:first-child::before,.mw-parser-output .hlist li li:first-child::before{content:" (";font-weight:normal}.mw-parser-output .hlist dd dd:last-child::after,.mw-parser-output .hlist dd dt:last-child::after,.mw-parser-output .hlist dd li:last-child::after,.mw-parser-output .hlist dt dd:last-child::after,.mw-parser-output .hlist dt dt:last-child::after,.mw-parser-output .hlist dt li:last-child::after,.mw-parser-output .hlist li dd:last-child::after,.mw-parser-output .hlist li dt:last-child::after,.mw-parser-output .hlist li li:last-child::after{content:")";font-weight:normal}.mw-parser-output .hlist ol{counter-reset:listitem}.mw-parser-output .hlist ol>li{counter-increment:listitem}.mw-parser-output .hlist ol>li::before{content:" "counter(listitem)"\a0 "}.mw-parser-output .hlist dd ol>li:first-child::before,.mw-parser-output .hlist dt ol>li:first-child::before,.mw-parser-output .hlist li ol>li:first-child::before{content:" ("counter(listitem)"\a0 "}</style><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Risk_of_venous_thromboembolism_with_hormone_therapy_and_birth_control_pills_(QResearch/CPRD)" title="Template:Risk of venous thromboembolism with hormone therapy and birth control pills (QResearch/CPRD)"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Risk_of_venous_thromboembolism_with_hormone_therapy_and_birth_control_pills_(QResearch/CPRD)" title="Template talk:Risk of venous thromboembolism with hormone therapy and birth control pills (QResearch/CPRD)"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Risk_of_venous_thromboembolism_with_hormone_therapy_and_birth_control_pills_(QResearch/CPRD)" title="Special:EditPage/Template:Risk of venous thromboembolism with hormone therapy and birth control pills (QResearch/CPRD)"><abbr title="Edit this template">e</abbr></a></li></ul></div> Risk of venous thromboembolism (VTE) with hormone therapy and birth control (QResearch/CPRD) </caption> <tbody><tr> <th class="unsortable">Type</th> <th class="unsortable">Route</th> <th class="unsortable">Medications</th> <th><a href="/wiki/Odds_ratio" title="Odds ratio">Odds ratio</a> (95% <a href="/wiki/Confidence_interval" title="Confidence interval"><abbr title="confidence interval">CI</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip confidence interval) </th></tr> <tr> <td rowspan="14"><a href="/wiki/Menopausal_hormone_therapy" class="mw-redirect" title="Menopausal hormone therapy">Menopausal hormone therapy</a></td> <td rowspan="10"><a href="/wiki/Oral_administration" title="Oral administration">Oral</a></td> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a> alone     ≤1 mg/day     >1 mg/day</td> <td>1.27 (1.16–1.39)* 1.22 (1.09–1.37)* 1.35 (1.18–1.55)* </td></tr> <tr> <td><a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a> alone     ≤0.625 mg/day     >0.625 mg/day</td> <td>1.49 (1.39–1.60)* 1.40 (1.28–1.53)* 1.71 (1.51–1.93)* </td></tr> <tr> <td><a href="/wiki/Estradiol/medroxyprogesterone_acetate" title="Estradiol/medroxyprogesterone acetate">Estradiol/medroxyprogesterone acetate</a></td> <td>1.44 (1.09–1.89)* </td></tr> <tr> <td><a href="/wiki/Estradiol/dydrogesterone" title="Estradiol/dydrogesterone">Estradiol/dydrogesterone</a>     ≤1 mg/day <abbr title="estradiol">E2</abbr>     >1 mg/day <abbr title="estradiol">E2</abbr></td> <td>1.18 (0.98–1.42) 1.12 (0.90–1.40) 1.34 (0.94–1.90) </td></tr> <tr> <td><a href="/wiki/Estradiol/norethisterone" title="Estradiol/norethisterone">Estradiol/norethisterone</a>     ≤1 mg/day <abbr title="estradiol">E2</abbr>     >1 mg/day <abbr title="estradiol">E2</abbr></td> <td>1.68 (1.57–1.80)* 1.38 (1.23–1.56)* 1.84 (1.69–2.00)* </td></tr> <tr> <td><a href="/wiki/Estradiol/norgestrel" class="mw-redirect" title="Estradiol/norgestrel">Estradiol/norgestrel</a> or <a href="/wiki/Estradiol/drospirenone" title="Estradiol/drospirenone">estradiol/drospirenone</a></td> <td>1.42 (1.00–2.03) </td></tr> <tr> <td><a href="/wiki/Conjugated_estrogens/medroxyprogesterone_acetate" title="Conjugated estrogens/medroxyprogesterone acetate">Conjugated estrogens/medroxyprogesterone acetate</a></td> <td>2.10 (1.92–2.31)* </td></tr> <tr> <td><a href="/wiki/Conjugated_estrogens/norgestrel" title="Conjugated estrogens/norgestrel">Conjugated estrogens/norgestrel</a>     ≤0.625 mg/day <abbr title="conjugated estrogens">CEEs</abbr>     >0.625 mg/day <abbr title="conjugated estrogens">CEEs</abbr></td> <td>1.73 (1.57–1.91)* 1.53 (1.36–1.72)* 2.38 (1.99–2.85)* </td></tr> <tr> <td><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a> alone</td> <td>1.02 (0.90–1.15) </td></tr> <tr> <td><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a> alone</td> <td>1.49 (1.24–1.79)* </td></tr> <tr> <td rowspan="2"><a href="/wiki/Transdermal_administration" class="mw-redirect" title="Transdermal administration">Transdermal</a></td> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a> alone    ≤50 μg/day    >50 μg/day</td> <td>0.96 (0.88–1.04) 0.94 (0.85–1.03) 1.05 (0.88–1.24) </td></tr> <tr> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a>/<a href="/wiki/Progestogen_(medication)" title="Progestogen (medication)">progestogen</a></td> <td>0.88 (0.73–1.01) </td></tr> <tr> <td rowspan="2"><a href="/wiki/Vaginal_administration" class="mw-redirect" title="Vaginal administration">Vaginal</a></td> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a> alone</td> <td>0.84 (0.73–0.97) </td></tr> <tr> <td><a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a> alone</td> <td>1.04 (0.76–1.43) </td></tr> <tr> <td rowspan="7"><a href="/wiki/Combined_birth_control" class="mw-redirect" title="Combined birth control">Combined birth control</a></td> <td rowspan="7"><a href="/wiki/Oral_administration" title="Oral administration">Oral</a></td> <td><a href="/wiki/Ethinylestradiol/norethisterone" title="Ethinylestradiol/norethisterone">Ethinylestradiol/norethisterone</a></td> <td>2.56 (2.15–3.06)* </td></tr> <tr> <td><a href="/wiki/Ethinylestradiol/levonorgestrel" title="Ethinylestradiol/levonorgestrel">Ethinylestradiol/levonorgestrel</a></td> <td>2.38 (2.18–2.59)* </td></tr> <tr> <td><a href="/wiki/Ethinylestradiol/norgestimate" class="mw-redirect" title="Ethinylestradiol/norgestimate">Ethinylestradiol/norgestimate</a></td> <td>2.53 (2.17–2.96)* </td></tr> <tr> <td><a href="/wiki/Ethinylestradiol/desogestrel" title="Ethinylestradiol/desogestrel">Ethinylestradiol/desogestrel</a></td> <td>4.28 (3.66–5.01)* </td></tr> <tr> <td><a href="/wiki/Ethinylestradiol/gestodene" title="Ethinylestradiol/gestodene">Ethinylestradiol/gestodene</a></td> <td>3.64 (3.00–4.43)* </td></tr> <tr> <td><a href="/wiki/Ethinylestradiol/drospirenone" title="Ethinylestradiol/drospirenone">Ethinylestradiol/drospirenone</a></td> <td>4.12 (3.43–4.96)* </td></tr> <tr> <td><a href="/wiki/Ethinylestradiol/cyproterone_acetate" title="Ethinylestradiol/cyproterone acetate">Ethinylestradiol/cyproterone acetate</a></td> <td>4.27 (3.57–5.11)* </td></tr> <tr class="sortbottom"> <td colspan="4" style="width: 1px; background-color:#eaecf0; text-align: center;">Notes: (1) <a href="/wiki/Nested_case%E2%80%93control_study" title="Nested case–control study">Nested case–control studies</a> (2015, 2019) based on data from the <a href="/wiki/QResearch" title="QResearch">QResearch</a> and <a href="/wiki/Clinical_Practice_Research_Datalink" title="Clinical Practice Research Datalink">Clinical Practice Research Datalink</a> (CPRD) databases. (2) <a href="/wiki/Bioidentical_hormone_therapy" class="mw-redirect" title="Bioidentical hormone therapy">Bioidentical</a> <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a> was not included, but is known to be associated with no additional risk relative to estrogen alone. Footnotes: * = <a href="/wiki/Statistical_significance" title="Statistical significance">Statistically significant</a> (p < 0.01). Sources: See template. </td></tr></tbody></table> <div class="mw-heading mw-heading4"><h4 id="Cardiovascular_issues">Cardiovascular issues</h4>[<a href="/w/index.php?title=Ethinylestradiol&action=edit&section=7" title="Edit section: Cardiovascular issues">edit</a>]</div> When used orally at high dosages, for instance as a form of high-dose estrogen therapy in men with prostate cancer and in women with breast cancer, <a href="/wiki/Synthetic_compound" class="mw-redirect" title="Synthetic compound">synthetic</a> and non-<a href="/wiki/Bioidentical" class="mw-redirect" title="Bioidentical">bioidentical</a> estrogens like EE and <a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">diethylstilbestrol</a> are associated with fairly high rates of severe <a href="/wiki/Cardiovascular" class="mw-redirect" title="Cardiovascular">cardiovascular</a> complications such as VTE, <a href="/wiki/Myocardial_infarction" title="Myocardial infarction">myocardial infarction</a>, and <a href="/wiki/Stroke" title="Stroke">stroke</a>.<a href="#cite_note-pmid27889048a-23">[23]</a><a href="#cite_note-pmid24256023-66">[66]</a><a href="#cite_note-pmid24932461-67">[67]</a> Diethylstilbestrol has been associated with an up to 35% risk of cardiovascular toxicity and death and a 15% incidence of VTE in men treated with it for prostate cancer.<a href="#cite_note-pmid24256023-66">[66]</a><a href="#cite_note-pmid24932461-67">[67]</a> EE has a to some degree lower risk of <a href="/wiki/Cardiovascular" class="mw-redirect" title="Cardiovascular">cardiovascular</a> complications than does diethylstilbestrol when used in the treatment of prostate cancer in men.<a href="#cite_note-OettelSchillinger2012-8">[8]</a> However, both EE and diethylstilbestrol nonetheless have highly disproportionate effects on <a href="/wiki/Liver_protein_synthesis" class="mw-redirect" title="Liver protein synthesis">liver protein synthesis</a>, which is thought to be responsible for their cardiovascular toxicity.<a href="#cite_note-pmid16112947-7">[7]</a><a href="#cite_note-pmid24932461-67">[67]</a> In contrast to oral synthetic estrogens like EE and diethylstilbestrol, high-dosage <a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">polyestradiol phosphate</a> and <a href="/wiki/Transdermal_administration" class="mw-redirect" title="Transdermal administration">transdermal</a> estradiol have not been found to increase the risk of cardiovascular <a href="/wiki/Mortality_rate" title="Mortality rate">mortality</a> or <a href="/wiki/Thromboembolism" title="Thromboembolism">thromboembolism</a> in men with prostate cancer.<a href="#cite_note-pmid24932461-67">[67]</a><a href="#cite_note-HongHolland2010-68">[68]</a><a href="#cite_note-pmid28667081-69">[69]</a> However, significantly increased cardiovascular <a href="/wiki/Morbidity" class="mw-redirect" title="Morbidity">morbidity</a> has been observed with high-dosage polyestradiol phosphate.<a href="#cite_note-pmid24932461-67">[67]</a><a href="#cite_note-HongHolland2010-68">[68]</a><a href="#cite_note-pmid28667081-69">[69]</a> In any case, these estrogens are considered to be much safer than oral synthetic estrogens like EE and diethylstilbestrol.<a href="#cite_note-pmid24932461-67">[67]</a><a href="#cite_note-HongHolland2010-68">[68]</a><a href="#cite_note-pmid28667081-69">[69]</a> In addition, <a href="/wiki/Ethinylestradiol_sulfonate" title="Ethinylestradiol sulfonate">ethinylestradiol sulfonate</a> (EES), an oral but <a href="/wiki/Parenteral" class="mw-redirect" title="Parenteral">parenteral</a>-like long-lasting prodrug of EE, is used in the treatment of prostate cancer, and is said to have a considerably better profile of cardiovascular safety than EE.<a href="#cite_note-OettelSchillinger2012-8">[8]</a> Because of its disproportionate effects on liver protein synthesis and associated cardiovascular risks, synthetic estrogens like EE and diethylstilbestrol are no longer used in menopausal hormone therapy.<a href="#cite_note-OettelSchillinger2012-8">[8]</a> They are also being replaced by parenteral forms of estradiol like polyestradiol phosphate and transdermal estradiol in the treatment of prostate cancer.<a href="#cite_note-pmid24932461-67">[67]</a> <div class="mw-heading mw-heading4"><h4 id="Liver_damage">Liver damage</h4>[<a href="/w/index.php?title=Ethinylestradiol&action=edit&section=8" title="Edit section: Liver damage">edit</a>]</div> At the lower dosages that are now used in birth control pills, EE has been associated rarely with <a href="/wiki/Cholestasis" title="Cholestasis">cholestatic</a> <a href="/wiki/Hepatotoxicity" title="Hepatotoxicity">hepatotoxicity</a> similarly to <a href="/wiki/17%CE%B1-alkylated_anabolic_steroid" class="mw-redirect" title="17α-alkylated anabolic steroid">17α-alkylated</a> <a href="/wiki/Androgen" title="Androgen">androgens</a>/<a href="/wiki/Anabolic_steroid" title="Anabolic steroid">anabolic steroids</a> and 17α-ethynylated <a href="/wiki/19-nortestosterone" class="mw-redirect" title="19-nortestosterone">19-nortestosterone</a> progestins.<a href="#cite_note-TraunerJansen2004-70">[70]</a><a href="#cite_note-ClavienBaillie2008-71">[71]</a> Cholestasis can manifest as <a href="/wiki/Pruritus" class="mw-redirect" title="Pruritus">pruritus</a> and <a href="/wiki/Jaundice" title="Jaundice">jaundice</a>.<a href="#cite_note-Kuhl1999-72">[72]</a> <a href="/wiki/Glucuronide" title="Glucuronide">Glucuronide</a> <a href="/wiki/Metabolite" title="Metabolite">metabolites</a> of EE, via effects on the <a href="/wiki/ABCB11" title="ABCB11">ABCB11 (BSEP)</a> and <a href="/wiki/Multidrug_resistance-associated_protein_2" title="Multidrug resistance-associated protein 2">MRP2 (ABCC2)</a> <a href="/wiki/Protein" title="Protein">proteins</a> and consequent changes in <a href="/wiki/Bile" title="Bile">bile</a> flow and <a href="/wiki/Bile_salt" class="mw-redirect" title="Bile salt">bile salt</a> <a href="/wiki/Excretion" title="Excretion">excretion</a>, appear to be responsible for the cholestasis.<a href="#cite_note-O'BrienBruce2010-73">[73]</a> Very high concentrations of estradiol, via its metabolite <a href="/wiki/Estradiol_glucuronide" title="Estradiol glucuronide">estradiol glucuronide</a>, are also implicated in cholestasis, for instance in <a href="/wiki/Cholestasis_of_pregnancy" class="mw-redirect" title="Cholestasis of pregnancy">cholestasis of pregnancy</a>.<a href="#cite_note-ClavienBaillie2008-71">[71]</a> However, the incidence and severity of cholestatic hepatotoxicity appear to be much greater with EE than with estradiol, which is thought to be due to the reactive C17α ethynyl substitution in EE as well as its greatly reduced susceptibility to hepatic metabolism.<a href="#cite_note-Aronson2009-38">[38]</a><a href="#cite_note-pmid2086334-74">[74]</a> Whereas abnormal <a href="/wiki/Liver_function_test" class="mw-redirect" title="Liver function test">liver function tests</a> (LFTs) are normally found in about 1% of women not on birth control pills or taking lower-dose EE-containing birth control pills, this increases to more than 10% of women taking birth control pills containing 50 μg/day EE or more.<a href="#cite_note-pmid2086334-74">[74]</a><a href="#cite_note-Kuhl1999-72">[72]</a> With birth control pills containing 50 μg/day EE, <a href="/wiki/Alanine_aminotransferase" class="mw-redirect" title="Alanine aminotransferase">alanine aminotransferase</a> (ALT) levels increase by 50%, <a href="/wiki/Hematocrit" title="Hematocrit">hematocrit</a> by 19%, and <a href="/wiki/Leukocytes" class="mw-redirect" title="Leukocytes">leukocytes</a> by 50%, while <a href="/wiki/Gamma-glutamyltransferase" title="Gamma-glutamyltransferase">gamma-glutamyltransferase</a> (GGT) decreases by 30%.<a href="#cite_note-pmid2086334-74">[74]</a> However, the values usually remain in the normal range.<a href="#cite_note-pmid2086334-74">[74]</a> In addition to abnormal LFTs, pathological changes in partial liver functions and liver <a href="/wiki/Morphology_(biology)" title="Morphology (biology)">morphology</a> can be observed in half of women on birth control pills with 50 μg/day EE.<a href="#cite_note-pmid2086334-74">[74]</a> EE-containing birth control pills have also been associated with a 25- to 50-fold increase in the risk of rare <a href="/wiki/Benign_liver_tumor" class="mw-redirect" title="Benign liver tumor">benign liver tumors</a> and a 3- to 6-fold increase in the risk of <a href="/wiki/Hepatocellular_carcinoma" title="Hepatocellular carcinoma">hepatocellular carcinoma</a>,<a href="#cite_note-Kuhl1999-72">[72]</a><a href="#cite_note-pmid30020636-75">[75]</a><a href="#cite_note-pmid17261770-76">[76]</a> as well as greater risk of other liver complications.<a href="#cite_note-pmid31009688-77">[77]</a><a href="#cite_note-pmid18814084-78">[78]</a> At one time, EE-containing birth control pills were estimated to be responsible for 84% of all drug-related and histologically verified liver damage.<a href="#cite_note-pmid2086334-74">[74]</a> However, these risks now are reduced with modern lower-dose EE-containing birth control pills, with contain 35 μg/day EE or less.<a href="#cite_note-Kuhl1999-72">[72]</a><a href="#cite_note-pmid17261770-76">[76]</a> <div class="mw-heading mw-heading4"><h4 id="Uterine_cancer">Uterine cancer</h4>[<a href="/w/index.php?title=Ethinylestradiol&action=edit&section=9" title="Edit section: Uterine cancer">edit</a>]</div> The high doses of EE that were used in early COCs were associated with a significantly increased risk of <a href="/wiki/Endometrial_cancer" title="Endometrial cancer">endometrial cancer</a> in certain preparations, for instance those containing the progestogen <a href="/wiki/Dimethisterone" title="Dimethisterone">dimethisterone</a>.<a href="#cite_note-Blaustein2013-79">[79]</a> Unopposed estrogens like EE have carcinogenic effects in the endometrium and progestogens protect against these effects, but dimethisterone is a relatively weak progestogen and was unable to adequately antagonize the endometrial carcinogenic effects of EE, in turn resulting in the increased risk of endometrial cancer.<a href="#cite_note-Blaustein2013-79">[79]</a> COCs containing dimethisterone have since been discontinued (with more potent progestogens used instead) and doses of EE in COCs in general have been dramatically reduced, abrogating the risk.<a href="#cite_note-Blaustein2013-79">[79]</a> In turn, most studies of modern COCs have found a decreased risk of endometrial cancer.<a href="#cite_note-SurwitAlberts2012-80">[80]</a> <div class="mw-heading mw-heading3"><h3 id="Ecological_Effects">Ecological Effects</h3>[<a href="/w/index.php?title=Ethinylestradiol&action=edit&section=10" title="Edit section: Ecological Effects">edit</a>]</div> <a href="/wiki/Wastewater" title="Wastewater">Wastewater</a> contains various estrogens, including EE, that are not completely broken down by <a href="/wiki/Wastewater_treatment" title="Wastewater treatment">wastewater treatment procedures</a>.<a href="#cite_note-:0-81">[81]</a> The input of artificial estrogens into <a href="/wiki/Fresh_water" title="Fresh water">freshwater</a> ecosystems affects <a href="/wiki/Fish" title="Fish">fish</a> and <a href="/wiki/Amphibian" title="Amphibian">amphibian</a> populations. Chronic exposure to low levels of EE over seven years led to the collapse of <a href="/wiki/Fathead_minnow" title="Fathead minnow">fathead minnow</a> populations in an <a href="/wiki/Experimental_Lakes_Area" title="Experimental Lakes Area">experimental lake</a> in <a href="/wiki/Ontario" title="Ontario">Ontario, Canada</a>.<a href="#cite_note-:0-81">[81]</a> EE changed <a href="/wiki/Oogenesis" title="Oogenesis">oogenesis</a> in female fish and feminized male fish such that they produced a protein associated with egg maturation, <a href="/wiki/Vitellogenin" title="Vitellogenin">vitellogenin</a>, as well as early-stage eggs.<a href="#cite_note-:0-81">[81]</a> In amphibians, exposure to EE can reduce hatching success and alter <a href="/wiki/Development_of_the_gonads" title="Development of the gonads">gonadal development</a>.<a href="#cite_note-:1-82">[82]</a> Exposure to hormones can change frogs' gonadal development even though it is <a href="/wiki/Sex_chromosome" title="Sex chromosome">encoded</a> in their <a href="/wiki/Gene" title="Gene">genes</a>.<a href="#cite_note-:1-82">[82]</a> A study of <a href="/wiki/Mink_frog" title="Mink frog">mink frogs</a> found more <a href="/wiki/Intersex" title="Intersex">intersex</a> <a href="/wiki/Tadpole" title="Tadpole">tadpoles</a> in those experimentally exposed to EE than those not exposed to EE, and <a href="/wiki/Lithobates_clamitans" title="Lithobates clamitans">green frogs</a> showed much lower rates of hatching success.<a href="#cite_note-:1-82">[82]</a> <div class="mw-heading mw-heading2"><h2 id="Overdose">Overdose</h2>[<a href="/w/index.php?title=Ethinylestradiol&action=edit&section=11" title="Edit section: Overdose">edit</a>]</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Estrogen_(medication)#Overdose" title="Estrogen (medication)">Estrogen (medication) § Overdose</a></div> Estrogens like EE are relatively safe in acute <a href="/wiki/Overdose" class="mw-redirect" title="Overdose">overdose</a>.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] <div class="mw-heading mw-heading2"><h2 id="Interactions">Interactions</h2>[<a href="/w/index.php?title=Ethinylestradiol&action=edit&section=12" title="Edit section: Interactions">edit</a>]</div> EE is metabolized by certain <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> isoforms, including <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a> and <a href="/wiki/CYP2C9" title="CYP2C9">CYP2C9</a>.<a href="#cite_note-83">[83]</a> Thus, <a href="/wiki/Enzyme_inducer" title="Enzyme inducer">inducers</a> of enzymes such as CYP3A4 can decrease circulating concentrations of EE.<a href="#cite_note-Aronson2009-38">[38]</a> Examples of inducers include <a href="/wiki/Anticonvulsant" title="Anticonvulsant">anticonvulsants</a> like <a href="/wiki/Phenytoin" title="Phenytoin">phenytoin</a>, <a href="/wiki/Primidone" title="Primidone">primidone</a>, <a href="/wiki/Ethosuximide" title="Ethosuximide">ethosuximide</a>, <a href="/wiki/Phenobarbital" title="Phenobarbital">phenobarbital</a>, and <a href="/wiki/Carbamazepine" title="Carbamazepine">carbamazepine</a>; <a href="/wiki/Azole" title="Azole">azole</a> <a href="/wiki/Antifungal" title="Antifungal">antifungals</a> like <a href="/wiki/Fluconazole" title="Fluconazole">fluconazole</a>; and <a href="/wiki/Rifamycin" title="Rifamycin">rifamycin</a> <a href="/wiki/Antibiotic" title="Antibiotic">antibiotics</a> like <a href="/wiki/Rifampin" class="mw-redirect" title="Rifampin">rifampin</a> (<a href="/wiki/Rifampicin" title="Rifampicin">rifampicin</a>).<a href="#cite_note-Aronson2009-38">[38]</a> Conversely, inhibitors of CYP3A4 and other cytochrome P450 enzymes may increase circulating levels of EE.<a href="#cite_note-Aronson2009-38">[38]</a> An example is <a href="/wiki/Troleandomycin" title="Troleandomycin">troleandomycin</a>, which is a potent and highly selective inhibitor of CYP3A4.<a href="#cite_note-Aronson2009-38">[38]</a> <a href="/wiki/Paracetamol" title="Paracetamol">Paracetamol</a> (acetaminophen) has been found to <a href="/wiki/Competitive_inhibition" title="Competitive inhibition">competitively inhibit</a> the sulfation of EE, with pretreatment of 1,000 mg of paracetamol significantly increasing the <a href="/wiki/Area-under-curve_(pharmacokinetics)" class="mw-redirect" title="Area-under-curve (pharmacokinetics)">AUC</a> levels of EE (by 22%) and decreasing the AUC levels of <a href="/wiki/Ethinylestradiol_sulfate" title="Ethinylestradiol sulfate">ethinylestradiol sulfate</a> (EE sulfate) in women.<a href="#cite_note-Aronson2009-38">[38]</a> The same has been found for <a href="/wiki/Ascorbic_acid" class="mw-redirect" title="Ascorbic acid">ascorbic acid</a> (vitamin C) and EE, although the significance of the interaction has been regarded as dubious.<a href="#cite_note-Aronson2009-38">[38]</a> In contrast to estradiol, it is unlikely that there is a pharmacokinetic interaction between <a href="/wiki/Smoking" title="Smoking">smoking</a> (which potently induces certain <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> <a href="/wiki/Enzyme" title="Enzyme">enzymes</a> and markedly increases the 2-hydroxylation of estradiol) and EE.<a href="#cite_note-Aronson2009-38">[38]</a> This suggests that estradiol and EE are metabolized by different cytochrome P450 enzymes.<a href="#cite_note-Aronson2009-38">[38]</a> There is, however, an increased risk of cardiovascular complications with smoking and EE, similarly to the case of smoking and other estrogens.<a href="#cite_note-Aronson2009-38">[38]</a> EE is known to <a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibit</a> several <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> enzymes, including <a href="/wiki/CYP1A2" title="CYP1A2">CYP1A2</a>, <a href="/wiki/CYP2B6" title="CYP2B6">CYP2B6</a>, <a href="/wiki/CYP2C9" title="CYP2C9">CYP2C9</a>, <a href="/wiki/CYP2C19" title="CYP2C19">CYP2C19</a>, and <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a>, and is possibly an <a href="/wiki/Enzyme_inducer" title="Enzyme inducer">inducer</a> of <a href="/wiki/CYP2A6" title="CYP2A6">CYP2A6</a>.<a href="#cite_note-pmid17253885-84">[84]</a> As a result, it can affect the metabolism and concentrations of many other drugs.<a href="#cite_note-pmid17253885-84">[84]</a> Examples of known interactions include <a href="/wiki/Bupropion" title="Bupropion">bupropion</a>, <a href="/wiki/Caffeine" title="Caffeine">caffeine</a>, <a href="/wiki/Mephenytoin" title="Mephenytoin">mephenytoin</a>, <a href="/wiki/Midazolam" title="Midazolam">midazolam</a>, <a href="/wiki/Nicotine" title="Nicotine">nicotine</a>, <a href="/wiki/Nifedipine" title="Nifedipine">nifedipine</a>, <a href="/wiki/Omeprazole" title="Omeprazole">omeprazole</a>, <a href="/wiki/Propranolol" title="Propranolol">propranolol</a>, <a href="/wiki/Proguanil" title="Proguanil">proguanil</a>, <a href="/wiki/Selegiline" title="Selegiline">selegiline</a>, <a href="/wiki/Theophylline" title="Theophylline">theophylline</a>, and <a href="/wiki/Tizanidine" title="Tizanidine">tizanidine</a>.<a href="#cite_note-pmid17253885-84">[84]</a><a href="#cite_note-Aronson2009-38">[38]</a> One of the most notable interactions is that EE strongly increases levels of <a href="/wiki/Selegiline" title="Selegiline">selegiline</a>, a substrate of CYP2B6 and CYP2C19.<a href="#cite_note-pmid17253885-84">[84]</a> EE may also induce <a href="/wiki/Glucuronidation" title="Glucuronidation">glucuronidation</a> and possibly alter <a href="/wiki/Sulfation" title="Sulfation">sulfation</a>.<a href="#cite_note-pmid17253885-84">[84]</a> It has been found to increase the clearance of and reduce the concentrations of a variety of drugs known to be glucuronidated.<a href="#cite_note-pmid17253885-84">[84]</a> Examples include <a href="/wiki/Clofibrate" title="Clofibrate">clofibrate</a>, <a href="/wiki/Lamotrigine" title="Lamotrigine">lamotrigine</a>, <a href="/wiki/Lorazepam" title="Lorazepam">lorazepam</a>, <a href="/wiki/Oxazepam" title="Oxazepam">oxazepam</a>, and <a href="/wiki/Propranolol" title="Propranolol">propranolol</a>.<a href="#cite_note-pmid17253885-84">[84]</a> Progestins, which are often used in combination with EE, are also known to inhibit cytochrome P450 enzymes, and this may contribute to drug interactions with EE-containing contraceptives as well.<a href="#cite_note-pmid17253885-84">[84]</a> Examples include <a href="/wiki/Gestodene" title="Gestodene">gestodene</a>, <a href="/wiki/Desogestrel" title="Desogestrel">desogestrel</a>, and <a href="/wiki/Etonogestrel" title="Etonogestrel">etonogestrel</a>, which are CYP3A4 and CYP2C19 inhibitors.<a href="#cite_note-pmid17253885-84">[84]</a> In addition, these progestins are known to progressively inhibit the metabolism of and increase concentrations of EE itself.<a href="#cite_note-Aronson2009-38">[38]</a> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2>[<a href="/w/index.php?title=Ethinylestradiol&action=edit&section=13" title="Edit section: Pharmacology">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Pharmacodynamics">Pharmacodynamics</h3>[<a href="/w/index.php?title=Ethinylestradiol&action=edit&section=14" title="Edit section: Pharmacodynamics">edit</a>]</div> EE is an <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogen</a> similarly to natural estrogens like estradiol and <a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">conjugated estrogens</a> (Premarin) and synthetic estrogens like <a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">diethylstilbestrol</a>. It binds to and activates both <a href="/wiki/Isoform" class="mw-redirect" title="Isoform">isoforms</a> of the <a href="/wiki/Estrogen_receptor" title="Estrogen receptor">estrogen receptor</a>, <a href="/wiki/Estrogen_receptor_alpha" title="Estrogen receptor alpha">ERα</a> and <a href="/wiki/Estrogen_receptor_beta" title="Estrogen receptor beta">ERβ</a>.<a href="#cite_note-OettelSchillinger2012-8">[8]</a> In one study, EE was found to have 233% and 38% of the <a href="/wiki/Affinity_(pharmacology)" class="mw-redirect" title="Affinity (pharmacology)">affinity</a> of <a href="/wiki/Estradiol" title="Estradiol">estradiol</a> for the ERα and ERβ, respectively.<a href="#cite_note-pmid16554039-85">[85]</a> In another study, it was found to possess 194% and 151% of the affinity of estradiol for the ERα and ERβ, respectively.<a href="#cite_note-pmid21321128-86">[86]</a> EE also appears to act as a <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potent</a> agonist of the <a href="/wiki/G_protein-coupled_estrogen_receptor" class="mw-redirect" title="G protein-coupled estrogen receptor">G protein-coupled estrogen receptor</a> (GPER) (affinity unknown), a <a href="/wiki/Membrane_estrogen_receptor" title="Membrane estrogen receptor">membrane estrogen receptor</a>, similarly to estradiol.<a href="#cite_note-pmid26023144-87">[87]</a><a href="#cite_note-pmid20403194-88">[88]</a><a href="#cite_note-pmid21844907-89">[89]</a><a href="#cite_note-pmid24530924-90">[90]</a> Estrogens have <a href="/wiki/Antigonadotropic" class="mw-redirect" title="Antigonadotropic">antigonadotropic</a> effects through activation of the ERα.<a href="#cite_note-QuaynorStradtman2013-91">[91]</a> As a contraceptive, EE acts in concert with a progestin to inhibit the mid-cycle surge in <a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone">luteinizing hormone</a> (LH) and <a href="/wiki/Follicle-stimulating_hormone" title="Follicle-stimulating hormone">follicle-stimulating hormone</a> (FSH) via its antigonadotropic effects, thereby inhibiting <a href="/wiki/Folliculogenesis" title="Folliculogenesis">folliculogenesis</a> and preventing <a href="/wiki/Ovulation" title="Ovulation">ovulation</a> and hence the possibility of <a href="/wiki/Pregnancy" title="Pregnancy">pregnancy</a>.<a href="#cite_note-CraigStitzel2004-92">[92]</a><a href="#cite_note-AllahbadiaAgrawal2007-93">[93]</a> EE is a long-acting estrogen, with a nuclear retention of about 24 hours.<a href="#cite_note-RunnebaumRabe2013-40">[40]</a> Orally, EE is on the order of 100 times as potent by weight as natural estrogens like <a href="/wiki/Micronized_estradiol" class="mw-redirect" title="Micronized estradiol">micronized estradiol</a> and conjugated estrogens, which is largely due to substantially greater resistance to <a href="/wiki/First-pass_metabolism" class="mw-redirect" title="First-pass metabolism">first-pass metabolism</a>.<a href="#cite_note-GomelMunro1990-94">[94]</a><a href="#cite_note-Shoupe2007-95">[95]</a><a href="#cite_note-McConaghy2013-96">[96]</a> It is specifically in the range of 80 to 200 times as potent as <a href="/wiki/Estropipate" title="Estropipate">estropipate</a> (piperazine estrone sulfate), which has similar potency to micronized estradiol, in terms of systemic estrogenic potency.<a href="#cite_note-ChabnerLongo1996-97">[97]</a><a href="#cite_note-pmid6291391-98">[98]</a> In contrast, the potencies of EE and natural estrogens are similar when they are administered <a href="/wiki/Intravenous_injection" class="mw-redirect" title="Intravenous injection">intravenously</a>, due to the bypassing of first-pass metabolism.<a href="#cite_note-FalconeHurd2007-50">[50]</a> Relative to its <a href="/wiki/Prodrug" title="Prodrug">prodrug</a> <a href="/wiki/Mestranol" title="Mestranol">mestranol</a>, EE is about 1.7 times as potent by weight orally.<a href="#cite_note-Shoupe2007-95">[95]</a> <table class="wikitable sortable mw-collapsible mw-collapsed" style="font-size: small; text-align:left; margin-left:auto; margin-right:auto; border:none;"> <caption class="nowrap"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Affinities_of_estrogen_receptor_ligands_for_the_ER%CE%B1_and_ER%CE%B2" title="Template:Affinities of estrogen receptor ligands for the ERα and ERβ"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Affinities_of_estrogen_receptor_ligands_for_the_ER%CE%B1_and_ER%CE%B2" title="Template talk:Affinities of estrogen receptor ligands for the ERα and ERβ"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Affinities_of_estrogen_receptor_ligands_for_the_ER%CE%B1_and_ER%CE%B2" title="Special:EditPage/Template:Affinities of estrogen receptor ligands for the ERα and ERβ"><abbr title="Edit this template">e</abbr></a></li></ul></div> Affinities of estrogen receptor ligands for the ERα and ERβ </caption> <tbody><tr> <th rowspan="2"><a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">Ligand</a></th> <th rowspan="2" class="unsortable">Other names</th> <th colspan="2"><a href="/wiki/Relative_binding_affinity" class="mw-redirect" title="Relative binding affinity">Relative binding affinities</a> (RBA, %)a</th> <th colspan="2"><a href="/wiki/Absolute_binding_affinity" class="mw-redirect" title="Absolute binding affinity">Absolute binding affinities</a> (Ki, nM)a</th> <th rowspan="2">Action </th></tr> <tr> <th><a href="/wiki/ER%CE%B1" class="mw-redirect" title="ERα">ERα</a></th> <th><a href="/wiki/ER%CE%B2" class="mw-redirect" title="ERβ">ERβ</a></th> <th><a href="/wiki/ER%CE%B1" class="mw-redirect" title="ERα">ERα</a></th> <th><a href="/wiki/ER%CE%B2" class="mw-redirect" title="ERβ">ERβ</a> </th></tr> <tr> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a></td> <td>E2; 17β-Estradiol</td> <td>100</td> <td>100</td> <td>0.115 (0.04–0.24)</td> <td>0.15 (0.10–2.08)</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Estrone_(medication)" title="Estrone (medication)">Estrone</a></td> <td>E1; 17-Ketoestradiol</td> <td>16.39 (0.7–60)</td> <td>6.5 (1.36–52)</td> <td>0.445 (0.3–1.01)</td> <td>1.75 (0.35–9.24)</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Estriol_(medication)" title="Estriol (medication)">Estriol</a></td> <td>E3; 16α-OH-17β-E2</td> <td>12.65 (4.03–56)</td> <td>26 (14.0–44.6)</td> <td>0.45 (0.35–1.4)</td> <td>0.7 (0.63–0.7)</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Estetrol_(medication)" title="Estetrol (medication)">Estetrol</a></td> <td>E4; 15α,16α-Di-OH-17β-E2</td> <td>4.0</td> <td>3.0</td> <td>4.9</td> <td>19</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Alfatradiol" title="Alfatradiol">Alfatradiol</a></td> <td>17α-Estradiol</td> <td>20.5 (7–80.1)</td> <td>8.195 (2–42)</td> <td>0.2–0.52</td> <td>0.43–1.2</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/16-Epiestriol" class="mw-redirect" title="16-Epiestriol">16-Epiestriol</a></td> <td>16β-Hydroxy-17β-estradiol</td> <td>7.795 (4.94–63)</td> <td>50</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/17-Epiestriol" class="mw-redirect" title="17-Epiestriol">17-Epiestriol</a></td> <td>16α-Hydroxy-17α-estradiol</td> <td>55.45 (29–103)</td> <td>79–80</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/16,17-Epiestriol" class="mw-redirect" title="16,17-Epiestriol">16,17-Epiestriol</a></td> <td>16β-Hydroxy-17α-estradiol</td> <td>1.0</td> <td>13</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/2-Hydroxyestradiol" title="2-Hydroxyestradiol">2-Hydroxyestradiol</a></td> <td>2-OH-E2</td> <td>22 (7–81)</td> <td>11–35</td> <td>2.5</td> <td>1.3</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/2-Methoxyestradiol" title="2-Methoxyestradiol">2-Methoxyestradiol</a></td> <td>2-MeO-E2</td> <td>0.0027–2.0</td> <td>1.0</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/4-Hydroxyestradiol" title="4-Hydroxyestradiol">4-Hydroxyestradiol</a></td> <td>4-OH-E2</td> <td>13 (8–70)</td> <td>7–56</td> <td>1.0</td> <td>1.9</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/4-Methoxyestradiol" title="4-Methoxyestradiol">4-Methoxyestradiol</a></td> <td>4-MeO-E2</td> <td>2.0</td> <td>1.0</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/2-Hydroxyestrone" title="2-Hydroxyestrone">2-Hydroxyestrone</a></td> <td>2-OH-E1</td> <td>2.0–4.0</td> <td>0.2–0.4</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/2-Methoxyestrone" title="2-Methoxyestrone">2-Methoxyestrone</a></td> <td>2-MeO-E1</td> <td><0.001–<1</td> <td><1</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/4-Hydroxyestrone" title="4-Hydroxyestrone">4-Hydroxyestrone</a></td> <td>4-OH-E1</td> <td>1.0–2.0</td> <td>1.0</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/4-Methoxyestrone" title="4-Methoxyestrone">4-Methoxyestrone</a></td> <td>4-MeO-E1</td> <td><1</td> <td><1</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/16%CE%B1-Hydroxyestrone" title="16α-Hydroxyestrone">16α-Hydroxyestrone</a></td> <td>16α-OH-E1; 17-Ketoestriol</td> <td>2.0–6.5</td> <td>35</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/2-Hydroxyestriol" title="2-Hydroxyestriol">2-Hydroxyestriol</a></td> <td>2-OH-E3</td> <td>2.0</td> <td>1.0</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/4-Methoxyestriol" title="4-Methoxyestriol">4-Methoxyestriol</a></td> <td>4-MeO-E3</td> <td>1.0</td> <td>1.0</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/Estradiol_sulfate" title="Estradiol sulfate">Estradiol sulfate</a></td> <td>E2S; Estradiol 3-sulfate</td> <td><1</td> <td><1</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/Estradiol_disulfate" title="Estradiol disulfate">Estradiol disulfate</a></td> <td>Estradiol 3,17β-disulfate</td> <td>0.0004</td> <td>?</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/Estradiol_3-glucuronide" title="Estradiol 3-glucuronide">Estradiol 3-glucuronide</a></td> <td>E2-3G</td> <td>0.0079</td> <td>?</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/Estradiol_17%CE%B2-glucuronide" class="mw-redirect" title="Estradiol 17β-glucuronide">Estradiol 17β-glucuronide</a></td> <td>E2-17G</td> <td>0.0015</td> <td>?</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/Estradiol_3-glucuronide_17%CE%B2-sulfate" title="Estradiol 3-glucuronide 17β-sulfate">Estradiol 3-gluc. 17β-sulfate</a></td> <td>E2-3G-17S</td> <td>0.0001</td> <td>?</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/Estrone_sulfate_(medication)" title="Estrone sulfate (medication)">Estrone sulfate</a></td> <td>E1S; Estrone 3-sulfate</td> <td><1</td> <td><1</td> <td>>10</td> <td>>10</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">Estradiol benzoate</a></td> <td>EB; Estradiol 3-benzoate</td> <td>10</td> <td>?</td> <td>?</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Estradiol_17%CE%B2-benzoate" title="Estradiol 17β-benzoate">Estradiol 17β-benzoate</a></td> <td>E2-17B</td> <td>11.3</td> <td>32.6</td> <td>?</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Estrone_methyl_ether" title="Estrone methyl ether">Estrone methyl ether</a></td> <td>Estrone 3-methyl ether</td> <td>0.145</td> <td>?</td> <td>?</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Ent-Estradiol" title="Ent-Estradiol">ent-Estradiol</a></td> <td>1-Estradiol</td> <td>1.31–12.34</td> <td>9.44–80.07</td> <td>?</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Equilin" title="Equilin">Equilin</a></td> <td>7-Dehydroestrone</td> <td>13 (4.0–28.9)</td> <td>13.0–49</td> <td>0.79</td> <td>0.36</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Equilenin" title="Equilenin">Equilenin</a></td> <td>6,8-Didehydroestrone</td> <td>2.0–15</td> <td>7.0–20</td> <td>0.64</td> <td>0.62</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/17%CE%B2-Dihydroequilin" title="17β-Dihydroequilin">17β-Dihydroequilin</a></td> <td>7-Dehydro-17β-estradiol</td> <td>7.9–113</td> <td>7.9–108</td> <td>0.09</td> <td>0.17</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/17%CE%B1-Dihydroequilin" title="17α-Dihydroequilin">17α-Dihydroequilin</a></td> <td>7-Dehydro-17α-estradiol</td> <td>18.6 (18–41)</td> <td>14–32</td> <td>0.24</td> <td>0.57</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/17%CE%B2-Dihydroequilenin" title="17β-Dihydroequilenin">17β-Dihydroequilenin</a></td> <td>6,8-Didehydro-17β-estradiol</td> <td>35–68</td> <td>90–100</td> <td>0.15</td> <td>0.20</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/17%CE%B1-Dihydroequilenin" title="17α-Dihydroequilenin">17α-Dihydroequilenin</a></td> <td>6,8-Didehydro-17α-estradiol</td> <td>20</td> <td>49</td> <td>0.50</td> <td>0.37</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/8,9-Dehydroestradiol" title="8,9-Dehydroestradiol">Δ8-Estradiol</a></td> <td>8,9-Dehydro-17β-estradiol</td> <td>68</td> <td>72</td> <td>0.15</td> <td>0.25</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/8,9-Dehydroestrone" title="8,9-Dehydroestrone">Δ8-Estrone</a></td> <td>8,9-Dehydroestrone</td> <td>19</td> <td>32</td> <td>0.52</td> <td>0.57</td> <td>Estrogen </td></tr> <tr> <td>Ethinylestradiol</td> <td>EE; 17α-Ethynyl-17β-E2</td> <td>120.9 (68.8–480)</td> <td>44.4 (2.0–144)</td> <td>0.02–0.05</td> <td>0.29–0.81</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Mestranol" title="Mestranol">Mestranol</a></td> <td>EE 3-methyl ether</td> <td>?</td> <td>2.5</td> <td>?</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Moxestrol" title="Moxestrol">Moxestrol</a></td> <td>RU-2858; 11β-Methoxy-EE</td> <td>35–43</td> <td>5–20</td> <td>0.5</td> <td>2.6</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Methylestradiol" title="Methylestradiol">Methylestradiol</a></td> <td>17α-Methyl-17β-estradiol</td> <td>70</td> <td>44</td> <td>?</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a></td> <td>DES; Stilbestrol</td> <td>129.5 (89.1–468)</td> <td>219.63 (61.2–295)</td> <td>0.04</td> <td>0.05</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Hexestrol" title="Hexestrol">Hexestrol</a></td> <td>Dihydrodiethylstilbestrol</td> <td>153.6 (31–302)</td> <td>60–234</td> <td>0.06</td> <td>0.06</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Dienestrol" title="Dienestrol">Dienestrol</a></td> <td>Dehydrostilbestrol</td> <td>37 (20.4–223)</td> <td>56–404</td> <td>0.05</td> <td>0.03</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Benzestrol" title="Benzestrol">Benzestrol (B2)</a></td> <td>–</td> <td>114</td> <td>?</td> <td>?</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Chlorotrianisene" title="Chlorotrianisene">Chlorotrianisene</a></td> <td>TACE</td> <td>1.74</td> <td>?</td> <td>15.30</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Triphenylethylene" title="Triphenylethylene">Triphenylethylene</a></td> <td>TPE</td> <td>0.074</td> <td>?</td> <td>?</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Triphenylbromoethylene" title="Triphenylbromoethylene">Triphenylbromoethylene</a></td> <td>TPBE</td> <td>2.69</td> <td>?</td> <td>?</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a></td> <td>ICI-46,474</td> <td>3 (0.1–47)</td> <td>3.33 (0.28–6)</td> <td>3.4–9.69</td> <td>2.5</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Afimoxifene" title="Afimoxifene">Afimoxifene</a></td> <td>4-Hydroxytamoxifen; 4-OHT</td> <td>100.1 (1.7–257)</td> <td>10 (0.98–339)</td> <td>2.3 (0.1–3.61)</td> <td>0.04–4.8</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Toremifene" title="Toremifene">Toremifene</a></td> <td>4-Chlorotamoxifen; 4-CT</td> <td>?</td> <td>?</td> <td>7.14–20.3</td> <td>15.4</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Clomifene" title="Clomifene">Clomifene</a></td> <td>MRL-41</td> <td>25 (19.2–37.2)</td> <td>12</td> <td>0.9</td> <td>1.2</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Cyclofenil" title="Cyclofenil">Cyclofenil</a></td> <td>F-6066; Sexovid</td> <td>151–152</td> <td>243</td> <td>?</td> <td>?</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Nafoxidine" title="Nafoxidine">Nafoxidine</a></td> <td>U-11,000A</td> <td>30.9–44</td> <td>16</td> <td>0.3</td> <td>0.8</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></td> <td>–</td> <td>41.2 (7.8–69)</td> <td>5.34 (0.54–16)</td> <td>0.188–0.52</td> <td>20.2</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Arzoxifene" title="Arzoxifene">Arzoxifene</a></td> <td>LY-353,381</td> <td>?</td> <td>?</td> <td>0.179</td> <td>?</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Lasofoxifene" title="Lasofoxifene">Lasofoxifene</a></td> <td>CP-336,156</td> <td>10.2–166</td> <td>19.0</td> <td>0.229</td> <td>?</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Ormeloxifene" title="Ormeloxifene">Ormeloxifene</a></td> <td>Centchroman</td> <td>?</td> <td>?</td> <td>0.313</td> <td>?</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Levormeloxifene" title="Levormeloxifene">Levormeloxifene</a></td> <td>6720-CDRI; NNC-460,020</td> <td>1.55</td> <td>1.88</td> <td>?</td> <td>?</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Ospemifene" title="Ospemifene">Ospemifene</a></td> <td>Deaminohydroxytoremifene</td> <td>0.82–2.63</td> <td>0.59–1.22</td> <td>?</td> <td>?</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Bazedoxifene" title="Bazedoxifene">Bazedoxifene</a></td> <td>–</td> <td>?</td> <td>?</td> <td>0.053</td> <td>?</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Etacstil" title="Etacstil">Etacstil</a></td> <td>GW-5638</td> <td>4.30</td> <td>11.5</td> <td>?</td> <td>?</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/ICI-164,384" class="mw-redirect" title="ICI-164,384">ICI-164,384</a></td> <td>–</td> <td>63.5 (3.70–97.7)</td> <td>166</td> <td>0.2</td> <td>0.08</td> <td>Antiestrogen </td></tr> <tr> <td><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant</a></td> <td>ICI-182,780</td> <td>43.5 (9.4–325)</td> <td>21.65 (2.05–40.5)</td> <td>0.42</td> <td>1.3</td> <td>Antiestrogen </td></tr> <tr> <td><a href="/wiki/Propylpyrazoletriol" title="Propylpyrazoletriol">Propylpyrazoletriol</a></td> <td>PPT</td> <td>49 (10.0–89.1)</td> <td>0.12</td> <td>0.40</td> <td>92.8</td> <td>ERα agonist </td></tr> <tr> <td><a href="/wiki/16%CE%B1-LE2" title="16α-LE2">16α-LE2</a></td> <td>16α-Lactone-17β-estradiol</td> <td>14.6–57</td> <td>0.089</td> <td>0.27</td> <td>131</td> <td>ERα agonist </td></tr> <tr> <td><a href="/wiki/16%CE%B1-Iodo-E2" title="16α-Iodo-E2">16α-Iodo-E2</a></td> <td>16α-Iodo-17β-estradiol</td> <td>30.2</td> <td>2.30</td> <td>?</td> <td>?</td> <td>ERα agonist </td></tr> <tr> <td><a href="/wiki/Methylpiperidinopyrazole" title="Methylpiperidinopyrazole">Methylpiperidinopyrazole</a></td> <td>MPP</td> <td>11</td> <td>0.05</td> <td>?</td> <td>?</td> <td>ERα antagonist </td></tr> <tr> <td><a href="/wiki/Diarylpropionitrile" title="Diarylpropionitrile">Diarylpropionitrile</a></td> <td>DPN</td> <td>0.12–0.25</td> <td>6.6–18</td> <td>32.4</td> <td>1.7</td> <td>ERβ agonist </td></tr> <tr> <td><a href="/wiki/8%CE%B2-VE2" title="8β-VE2">8β-VE2</a></td> <td>8β-Vinyl-17β-estradiol</td> <td>0.35</td> <td>22.0–83</td> <td>12.9</td> <td>0.50</td> <td>ERβ agonist </td></tr> <tr> <td><a href="/wiki/Prinaberel" title="Prinaberel">Prinaberel</a></td> <td>ERB-041; WAY-202,041</td> <td>0.27</td> <td>67–72</td> <td>?</td> <td>?</td> <td>ERβ agonist </td></tr> <tr> <td><a href="/wiki/ERB-196" title="ERB-196">ERB-196</a></td> <td>WAY-202,196</td> <td>?</td> <td>180</td> <td>?</td> <td>?</td> <td>ERβ agonist </td></tr> <tr> <td><a href="/wiki/Erteberel" title="Erteberel">Erteberel</a></td> <td>SERBA-1; LY-500,307</td> <td>?</td> <td>?</td> <td>2.68</td> <td>0.19</td> <td>ERβ agonist </td></tr> <tr> <td><a href="/wiki/SERBA-2" title="SERBA-2">SERBA-2</a></td> <td>–</td> <td>?</td> <td>?</td> <td>14.5</td> <td>1.54</td> <td>ERβ agonist </td></tr> <tr> <td><a href="/wiki/Coumestrol" title="Coumestrol">Coumestrol</a></td> <td>–</td> <td>9.225 (0.0117–94)</td> <td>64.125 (0.41–185)</td> <td>0.14–80.0</td> <td>0.07–27.0</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Genistein" title="Genistein">Genistein</a></td> <td>–</td> <td>0.445 (0.0012–16)</td> <td>33.42 (0.86–87)</td> <td>2.6–126</td> <td>0.3–12.8</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Equol" title="Equol">Equol</a></td> <td>–</td> <td>0.2–0.287</td> <td>0.85 (0.10–2.85)</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Daidzein" title="Daidzein">Daidzein</a></td> <td>–</td> <td>0.07 (0.0018–9.3)</td> <td>0.7865 (0.04–17.1)</td> <td>2.0</td> <td>85.3</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Biochanin_A" title="Biochanin A">Biochanin A</a></td> <td>–</td> <td>0.04 (0.022–0.15)</td> <td>0.6225 (0.010–1.2)</td> <td>174</td> <td>8.9</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Kaempferol" title="Kaempferol">Kaempferol</a></td> <td>–</td> <td>0.07 (0.029–0.10)</td> <td>2.2 (0.002–3.00)</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Naringenin" title="Naringenin">Naringenin</a></td> <td>–</td> <td>0.0054 (<0.001–0.01)</td> <td>0.15 (0.11–0.33)</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/8-Prenylnaringenin" title="8-Prenylnaringenin">8-Prenylnaringenin</a></td> <td>8-PN</td> <td>4.4</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Quercetin" title="Quercetin">Quercetin</a></td> <td>–</td> <td><0.001–0.01</td> <td>0.002–0.040</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Ipriflavone" title="Ipriflavone">Ipriflavone</a></td> <td>–</td> <td><0.01</td> <td><0.01</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Miroestrol" title="Miroestrol">Miroestrol</a></td> <td>–</td> <td>0.39</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Deoxymiroestrol" class="mw-redirect" title="Deoxymiroestrol">Deoxymiroestrol</a></td> <td>–</td> <td>2.0</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/%CE%92-Sitosterol" title="Β-Sitosterol">β-Sitosterol</a></td> <td>–</td> <td><0.001–0.0875</td> <td><0.001–0.016</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Resveratrol" title="Resveratrol">Resveratrol</a></td> <td>–</td> <td><0.001–0.0032</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/%CE%91-Zearalenol" title="Α-Zearalenol">α-Zearalenol</a></td> <td>–</td> <td>48 (13–52.5)</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/%CE%92-Zearalenol" title="Β-Zearalenol">β-Zearalenol</a></td> <td>–</td> <td>0.6 (0.032–13)</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Zeranol" title="Zeranol">Zeranol</a></td> <td>α-Zearalanol</td> <td>48–111</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Taleranol" title="Taleranol">Taleranol</a></td> <td>β-Zearalanol</td> <td>16 (13–17.8)</td> <td>14</td> <td>0.8</td> <td>0.9</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Zearalenone" title="Zearalenone">Zearalenone</a></td> <td>ZEN</td> <td>7.68 (2.04–28)</td> <td>9.45 (2.43–31.5)</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Zearalanone" title="Zearalanone">Zearalanone</a></td> <td>ZAN</td> <td>0.51</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Bisphenol_A" title="Bisphenol A">Bisphenol A</a></td> <td>BPA</td> <td>0.0315 (0.008–1.0)</td> <td>0.135 (0.002–4.23)</td> <td>195</td> <td>35</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Endosulfan" title="Endosulfan">Endosulfan</a></td> <td>EDS</td> <td><0.001–<0.01</td> <td><0.01</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Kepone" class="mw-redirect" title="Kepone">Kepone</a></td> <td>Chlordecone</td> <td>0.0069–0.2</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/O,p%27-DDT" class="mw-redirect" title="O,p'-DDT">o,p'-DDT</a></td> <td>–</td> <td>0.0073–0.4</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/P,p%27-DDT" class="mw-redirect" title="P,p'-DDT">p,p'-DDT</a></td> <td>–</td> <td>0.03</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Methoxychlor" title="Methoxychlor">Methoxychlor</a></td> <td>p,p'-Dimethoxy-DDT</td> <td>0.01 (<0.001–0.02)</td> <td>0.01–0.13</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/HPTE" title="HPTE">HPTE</a></td> <td>Hydroxychlor; p,p'-OH-DDT</td> <td>1.2–1.7</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">Testosterone</a></td> <td>T; 4-Androstenolone</td> <td><0.0001–<0.01</td> <td><0.002–0.040</td> <td>>5000</td> <td>>5000</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/Androstanolone" title="Androstanolone">Dihydrotestosterone</a></td> <td>DHT; 5α-Androstanolone</td> <td>0.01 (<0.001–0.05)</td> <td>0.0059–0.17</td> <td>221–>5000</td> <td>73–1688</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/Nandrolone" title="Nandrolone">Nandrolone</a></td> <td>19-Nortestosterone; 19-NT</td> <td>0.01</td> <td>0.23</td> <td>765</td> <td>53</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/Prasterone" title="Prasterone">Dehydroepiandrosterone</a></td> <td>DHEA; Prasterone</td> <td>0.038 (<0.001–0.04)</td> <td>0.019–0.07</td> <td>245–1053</td> <td>163–515</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/5-Androstenediol" class="mw-redirect" title="5-Androstenediol">5-Androstenediol</a></td> <td>A5; Androstenediol</td> <td>6</td> <td>17</td> <td>3.6</td> <td>0.9</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/4-Androstenediol" title="4-Androstenediol">4-Androstenediol</a></td> <td>–</td> <td>0.5</td> <td>0.6</td> <td>23</td> <td>19</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/4-Androstenedione" class="mw-redirect" title="4-Androstenedione">4-Androstenedione</a></td> <td>A4; Androstenedione</td> <td><0.01</td> <td><0.01</td> <td>>10000</td> <td>>10000</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></td> <td>3α-Adiol</td> <td>0.07</td> <td>0.3</td> <td>260</td> <td>48</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/3%CE%B2-Androstanediol" title="3β-Androstanediol">3β-Androstanediol</a></td> <td>3β-Adiol</td> <td>3</td> <td>7</td> <td>6</td> <td>2</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/Androstanedione" title="Androstanedione">Androstanedione</a></td> <td>5α-Androstanedione</td> <td><0.01</td> <td><0.01</td> <td>>10000</td> <td>>10000</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/Etiocholanedione" title="Etiocholanedione">Etiocholanedione</a></td> <td>5β-Androstanedione</td> <td><0.01</td> <td><0.01</td> <td>>10000</td> <td>>10000</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/Methyltestosterone" title="Methyltestosterone">Methyltestosterone</a></td> <td>17α-Methyltestosterone</td> <td><0.0001</td> <td>?</td> <td>?</td> <td>?</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/Ethinyl-3%CE%B1-androstanediol" class="mw-redirect" title="Ethinyl-3α-androstanediol">Ethinyl-3α-androstanediol</a></td> <td>17α-Ethynyl-3α-adiol</td> <td>4.0</td> <td><0.07</td> <td>?</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Ethinyl-3%CE%B2-androstanediol" class="mw-redirect" title="Ethinyl-3β-androstanediol">Ethinyl-3β-androstanediol</a></td> <td>17α-Ethynyl-3β-adiol</td> <td>50</td> <td>5.6</td> <td>?</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">Progesterone</a></td> <td>P4; 4-Pregnenedione</td> <td><0.001–0.6</td> <td><0.001–0.010</td> <td>?</td> <td>?</td> <td>Progestogen </td></tr> <tr> <td><a href="/wiki/Norethisterone" title="Norethisterone">Norethisterone</a></td> <td>NET; 17α-Ethynyl-19-NT</td> <td>0.085 (0.0015–<0.1)</td> <td>0.1 (0.01–0.3)</td> <td>152</td> <td>1084</td> <td>Progestogen </td></tr> <tr> <td><a href="/wiki/Norethynodrel" class="mw-redirect" title="Norethynodrel">Norethynodrel</a></td> <td>5(10)-Norethisterone</td> <td>0.5 (0.3–0.7)</td> <td><0.1–0.22</td> <td>14</td> <td>53</td> <td>Progestogen </td></tr> <tr> <td><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></td> <td>7α-Methylnorethynodrel</td> <td>0.5 (0.45–2.0)</td> <td>0.2–0.076</td> <td>?</td> <td>?</td> <td>Progestogen </td></tr> <tr> <td><a href="/wiki/%CE%944-Tibolone" title="Δ4-Tibolone">Δ4-Tibolone</a></td> <td>7α-Methylnorethisterone</td> <td>0.069–<0.1</td> <td>0.027–<0.1</td> <td>?</td> <td>?</td> <td>Progestogen </td></tr> <tr> <td><a href="/wiki/3%CE%B1-Hydroxytibolone" title="3α-Hydroxytibolone">3α-Hydroxytibolone</a></td> <td>–</td> <td>2.5 (1.06–5.0)</td> <td>0.6–0.8</td> <td>?</td> <td>?</td> <td>Progestogen </td></tr> <tr> <td><a href="/wiki/3%CE%B2-Hydroxytibolone" title="3β-Hydroxytibolone">3β-Hydroxytibolone</a></td> <td>–</td> <td>1.6 (0.75–1.9)</td> <td>0.070–0.1</td> <td>?</td> <td>?</td> <td>Progestogen </td></tr> <tr class="sortbottom"> <td colspan="7" style="width: 1px; background-color:#eaecf0; text-align: center;">Footnotes: a = (1) <a href="/wiki/Binding_affinity" class="mw-redirect" title="Binding affinity">Binding affinity</a> values are of the format "median (range)" (# (#–#)), "range" (#–#), or "value" (#) depending on the values available. The full sets of values within the ranges can be found in the Wiki code. (2) Binding affinities were determined via displacement studies in a variety of <a href="/wiki/In-vitro" class="mw-redirect" title="In-vitro">in-vitro</a> systems with <a href="/wiki/Radiolabel" class="mw-redirect" title="Radiolabel">labeled</a> estradiol and human <a href="/wiki/ER%CE%B1" class="mw-redirect" title="ERα">ERα</a> and <a href="/wiki/ER%CE%B2" class="mw-redirect" title="ERβ">ERβ</a> proteins (except the ERβ values from Kuiper et al. (1997), which are rat ERβ). Sources: See template page. </td></tr></tbody></table> <table class="wikitable sortable mw-collapsible mw-collapsed" style="text-align:left; margin-left:auto; margin-right:auto; border:none;"> <caption class="nowrap"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Relative_affinities_of_estrogens_for_steroid_hormone_receptors_and_blood_proteins" title="Template:Relative affinities of estrogens for steroid hormone receptors and blood proteins"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Relative_affinities_of_estrogens_for_steroid_hormone_receptors_and_blood_proteins" title="Template talk:Relative affinities of estrogens for steroid hormone receptors and blood proteins"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Relative_affinities_of_estrogens_for_steroid_hormone_receptors_and_blood_proteins" title="Special:EditPage/Template:Relative affinities of estrogens for steroid hormone receptors and blood proteins"><abbr title="Edit this template">e</abbr></a></li></ul></div> Relative affinities of estrogens for steroid hormone receptors and blood proteins </caption> <tbody><tr> <th rowspan="2"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogen</a></th> <th colspan="7"><a href="/wiki/Relative_binding_affinity" class="mw-redirect" title="Relative binding affinity">Relative binding affinities</a> (%) </th></tr> <tr> <th><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor</th> <th><a href="/wiki/Androgen_receptor" title="Androgen receptor"><abbr title="Androgen receptor">AR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Androgen receptor</th> <th><a href="/wiki/Progesterone_receptor" title="Progesterone receptor"><abbr title="Progesterone receptor">PR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Progesterone receptor</th> <th><a href="/wiki/Glucocorticoid_receptor" title="Glucocorticoid receptor"><abbr title="Glucocorticoid receptor">GR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Glucocorticoid receptor</th> <th><a href="/wiki/Mineralocorticoid_receptor" title="Mineralocorticoid receptor"><abbr title="Mineralocorticoid receptor">MR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Mineralocorticoid receptor</th> <th><a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin"><abbr title="Sex hormone-binding globulin">SHBG</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Sex hormone-binding globulin</th> <th><a href="/wiki/Corticosteroid_binding_globulin" class="mw-redirect" title="Corticosteroid binding globulin"><abbr title="Corticosteroid binding globulin">CBG</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Corticosteroid binding globulin </th></tr> <tr> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a></td> <td>100</td> <td>7.9</td> <td>2.6</td> <td>0.6</td> <td>0.13</td> <td>8.7–12</td> <td><0.1 </td></tr> <tr> <td><a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">Estradiol benzoate</a></td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td><0.1–0.16</td> <td><0.1 </td></tr> <tr> <td><a href="/wiki/Estradiol_valerate" title="Estradiol valerate">Estradiol valerate</a></td> <td>2</td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>? </td></tr> <tr> <td><a href="/wiki/Estrone_(medication)" title="Estrone (medication)">Estrone</a></td> <td>11–35</td> <td><1</td> <td><1</td> <td><1</td> <td><1</td> <td>2.7</td> <td><0.1 </td></tr> <tr> <td><a href="/wiki/Estrone_sulfate_(medication)" title="Estrone sulfate (medication)">Estrone sulfate</a></td> <td>2</td> <td>2</td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>? </td></tr> <tr> <td><a href="/wiki/Estriol_(medication)" title="Estriol (medication)">Estriol</a></td> <td>10–15</td> <td><1</td> <td><1</td> <td><1</td> <td><1</td> <td><0.1</td> <td><0.1 </td></tr> <tr> <td><a href="/wiki/Equilin" title="Equilin">Equilin</a></td> <td>40</td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>0 </td></tr> <tr> <td><a href="/wiki/Alfatradiol" title="Alfatradiol">Alfatradiol</a></td> <td>15</td> <td><1</td> <td><1</td> <td><1</td> <td><1</td> <td>?</td> <td>? </td></tr> <tr> <td><a href="/wiki/Epiestriol" title="Epiestriol">Epiestriol</a></td> <td>20</td> <td><1</td> <td><1</td> <td><1</td> <td><1</td> <td>?</td> <td>? </td></tr> <tr> <td>Ethinylestradiol</td> <td>100–112</td> <td>1–3</td> <td>15–25</td> <td>1–3</td> <td><1</td> <td>0.18</td> <td><0.1 </td></tr> <tr> <td><a href="/wiki/Mestranol" title="Mestranol">Mestranol</a></td> <td>1</td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td><0.1</td> <td><0.1 </td></tr> <tr> <td><a href="/wiki/Methylestradiol" title="Methylestradiol">Methylestradiol</a></td> <td>67</td> <td>1–3</td> <td>3–25</td> <td>1–3</td> <td><1</td> <td>?</td> <td>? </td></tr> <tr> <td><a href="/wiki/Moxestrol" title="Moxestrol">Moxestrol</a></td> <td>12</td> <td><0.1</td> <td>0.8</td> <td>3.2</td> <td><0.1</td> <td><0.2</td> <td><0.1 </td></tr> <tr> <td><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a></td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td><0.1</td> <td><0.1 </td></tr> <tr class="sortbottom"> <td colspan="8" style="width: 1px; background-color:#eaecf0; text-align: center;">Notes: Reference <a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">ligands</a> (100%) were <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a> for the <a href="/wiki/Progesterone_receptor" title="Progesterone receptor"><abbr title="progesterone receptor">PR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip progesterone receptor, <a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">testosterone</a> for the <a href="/wiki/Androgen_receptor" title="Androgen receptor"><abbr title="androgen receptor">AR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip androgen receptor, <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a> for the <a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip estrogen receptor, <a href="/wiki/Dexamethasone" title="Dexamethasone">dexamethasone</a> for the <a href="/wiki/Glucocorticoid_receptor" title="Glucocorticoid receptor"><abbr title="glucocorticoid receptor">GR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip glucocorticoid receptor, <a href="/wiki/Aldosterone" title="Aldosterone">aldosterone</a> for the <a href="/wiki/Mineralocorticoid_receptor" title="Mineralocorticoid receptor"><abbr title="mineralocorticoid receptor">MR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip mineralocorticoid receptor, <a href="/wiki/Androstanolone" title="Androstanolone">dihydrotestosterone</a> for <a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin"><abbr title="sex hormone-binding globulin">SHBG</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip sex hormone-binding globulin, and <a href="/wiki/Hydrocortisone" title="Hydrocortisone">cortisol</a> for <a href="/wiki/Corticosteroid-binding_globulin" class="mw-redirect" title="Corticosteroid-binding globulin"><abbr title="Corticosteroid-binding globulin">CBG</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Corticosteroid-binding globulin. Sources: See template. </td></tr></tbody></table> <table style="font-size: small; margin-left: auto; margin-right: auto; border: none;" class="wikitable sortable mw-collapsible mw-collapsed"> <caption class="nowrap" style="font-size: 105%;"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Relative_oral_potencies_of_estrogens" title="Template:Relative oral potencies of estrogens"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Relative_oral_potencies_of_estrogens" title="Template talk:Relative oral potencies of estrogens"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Relative_oral_potencies_of_estrogens" title="Special:EditPage/Template:Relative oral potencies of estrogens"><abbr title="Edit this template">e</abbr></a></li></ul></div> Relative oral potencies of estrogens </caption> <tbody><tr> <th>Estrogen</th> <th data-sort-type="number"><a href="/wiki/Hot_flashes" class="mw-redirect" title="Hot flashes"><abbr title="Hot flashes">HF</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Hot flashes</th> <th data-sort-type="number"><a href="/wiki/Vaginal_epithelium" title="Vaginal epithelium"><abbr title="Vaginal epithelium">VE</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Vaginal epithelium</th> <th data-sort-type="number"><a href="/wiki/Urinary_calcium" title="Urinary calcium"><abbr title="Urinary calcium">UCa</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Urinary calcium</th> <th data-sort-type="number"><a href="/wiki/Follicle-stimulating_hormone" title="Follicle-stimulating hormone"><abbr title="Follicle-stimulating hormone">FSH</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Follicle-stimulating hormone</th> <th data-sort-type="number"><a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone"><abbr title="Luteinizing hormone">LH</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Luteinizing hormone</th> <th data-sort-type="number"><a href="/wiki/High-density_lipoprotein" title="High-density lipoprotein"><abbr title="High-density lipoprotein">HDL</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip High-density lipoprotein-<a href="/wiki/Cholesterol" title="Cholesterol"><abbr title="Cholesterol">C</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Cholesterol</th> <th data-sort-type="number"><a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin"><abbr title="Sex hormone-binding globulin">SHBG</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Sex hormone-binding globulin</th> <th data-sort-type="number"><a href="/wiki/Corticosteroid-binding_globulin" class="mw-redirect" title="Corticosteroid-binding globulin"><abbr title="Corticosteroid-binding globulin">CBG</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Corticosteroid-binding globulin</th> <th data-sort-type="number"><a href="/wiki/Angiotensinogen" class="mw-redirect" title="Angiotensinogen"><abbr title="Angiotensinogen">AGT</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Angiotensinogen</th> <th data-sort-type="number"><abbr title="Ratio of liver estrogenic effects to general/systemic estrogenic effects)">Liver</abbr> </th></tr> <tr> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a></td> <td>1.0</td> <td>1.0</td> <td>1.0</td> <td>1.0</td> <td>1.0</td> <td>1.0</td> <td>1.0</td> <td>1.0</td> <td>1.0</td> <td>1.0 </td></tr> <tr> <td><a href="/wiki/Estrone_(medication)" title="Estrone (medication)">Estrone</a></td> <td>?</td> <td>?</td> <td>?</td> <td>0.3</td> <td>0.3</td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>? </td></tr> <tr> <td><a href="/wiki/Estriol_(medication)" title="Estriol (medication)">Estriol</a></td> <td>0.3</td> <td>0.3</td> <td>0.1</td> <td>0.3</td> <td>0.3</td> <td>0.2</td> <td>?</td> <td>?</td> <td>?</td> <td>0.67 </td></tr> <tr> <td><a href="/wiki/Estrone_sulfate_(medication)" title="Estrone sulfate (medication)">Estrone sulfate</a></td> <td>?</td> <td>0.9</td> <td>0.9</td> <td>0.8–0.9</td> <td>0.9</td> <td>0.5</td> <td>0.9</td> <td>0.5–0.7</td> <td>1.4–1.5</td> <td>0.56–1.7 </td></tr> <tr> <td><a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a></td> <td>1.2</td> <td>1.5</td> <td>2.0</td> <td>1.1–1.3</td> <td>1.0</td> <td>1.5</td> <td>3.0–3.2</td> <td>1.3–1.5</td> <td>5.0</td> <td>1.3–4.5 </td></tr> <tr> <td><a href="/wiki/Equilin_sulfate" class="mw-redirect" title="Equilin sulfate">Equilin sulfate</a></td> <td>?</td> <td>?</td> <td>1.0</td> <td>?</td> <td>?</td> <td>6.0</td> <td>7.5</td> <td>6.0</td> <td>7.5</td> <td>? </td></tr> <tr> <td>Ethinylestradiol</td> <td>120</td> <td>150</td> <td>400</td> <td>60–150</td> <td>100</td> <td>400</td> <td>500–600</td> <td>500–600</td> <td>350</td> <td>2.9–5.0 </td></tr> <tr> <td><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a></td> <td>?</td> <td>?</td> <td>?</td> <td>2.9–3.4</td> <td>?</td> <td>?</td> <td>26–28</td> <td>25–37</td> <td>20</td> <td>5.7–7.5 </td></tr> <tr class="sortbottom"> <td colspan="11" style="width: 1px; background-color:#eaecf0; text-align: center;"><style data-mw-deduplicate="TemplateStyles:r1214851843">.mw-parser-output .hidden-begin{box-sizing:border-box;width:100%;padding:5px;border:none;font-size:95%}.mw-parser-output .hidden-title{font-weight:bold;line-height:1.6;text-align:left}.mw-parser-output .hidden-content{text-align:left}@media all and (max-width:500px){.mw-parser-output .hidden-begin{width:auto!important;clear:none!important;float:none!important}}</style><div class="hidden-begin mw-collapsible mw-collapsed" style=""><div class="hidden-title skin-nightmode-reset-color" style="text-align:center;">Sources and footnotes</div><div class="hidden-content mw-collapsible-content" style=""> Notes: Values are ratios, with estradiol as standard (i.e., 1.0). Abbreviations: <abbr title="Hot flashes">HF</abbr> = Clinical relief of <a href="/wiki/Hot_flash" title="Hot flash">hot flashes</a>. <abbr title="Vaginal epithelium">VE</abbr> = Increased <a href="/wiki/Cell_proliferation" title="Cell proliferation">proliferation</a> of <a href="/wiki/Vaginal_epithelium" title="Vaginal epithelium">vaginal epithelium</a>. <abbr title="Urinary calcium">UCa</abbr> = Decrease in <a href="/wiki/Urinary_calcium" title="Urinary calcium"><abbr title="urinary calcium">UCa</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip urinary calcium. <abbr title="follicle-stimulating hormone">FSH</abbr> = Suppression of <a href="/wiki/Follicle-stimulating_hormone" title="Follicle-stimulating hormone"><abbr title="follicle-stimulating hormone">FSH</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip follicle-stimulating hormone levels. <abbr title="luteinizing hormone">LH</abbr> = Suppression of <a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone"><abbr title="luteinizing hormone">LH</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip luteinizing hormone levels. <abbr title="high-density lipoprotein">HDL</abbr>-<abbr title="cholesterol">C</abbr>, <abbr title="sex hormone-binding globulin">SHBG</abbr>, <abbr title="corticosteroid-binding globulin">CBG</abbr>, and <abbr title="angiotensinogen">AGT</abbr> = Increase in the serum levels of these <a href="/wiki/Liver_protein" class="mw-redirect" title="Liver protein">liver proteins</a>. Liver = Ratio of liver estrogenic effects to general/systemic estrogenic effects (hot flashes/<a href="/wiki/Gonadotropin" title="Gonadotropin">gonadotropins</a>). Sources: See template.</div></div> </td></tr></tbody></table> <table class="wikitable plainrowheaders floatright" style="font-size: small; margin: 1em auto;"> <caption class="nowrap" style="font-size: 105%"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Oral_potencies_of_estrogens" title="Template:Oral potencies of estrogens"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Oral_potencies_of_estrogens" title="Template talk:Oral potencies of estrogens"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Oral_potencies_of_estrogens" title="Special:EditPage/Template:Oral potencies of estrogens"><abbr title="Edit this template">e</abbr></a></li></ul></div> Potencies of oral estrogens<a href="#cite_note-118">[data sources 1]</a> </caption> <tbody><tr> <th scope="col" style="width=100px;" rowspan="2">Compound </th> <th scope="col" colspan="6">Dosage for specific uses (mg usually)<a href="#cite_note-119">[a]</a> </th></tr> <tr> <th scope="col" style="width=100px;"><abbr title="Endometrial threshold dose">ETD</abbr><a href="#cite_note-2-3-120">[b]</a> </th> <th scope="col" style="width=100px;"><abbr title="Endometrial proliferation dose">EPD</abbr><a href="#cite_note-2-3-120">[b]</a> </th> <th scope="col" style="width=100px;"><abbr title="Menopausal substitution dose">MSD</abbr><a href="#cite_note-2-3-120">[b]</a> </th> <th scope="col" style="width=100px;"><abbr title="Menopausal substitution dose">MSD</abbr><a href="#cite_note-daily-121">[c]</a> </th> <th scope="col" style="width=100px;"><abbr title="Ovulation-inhibiting dose">OID</abbr><a href="#cite_note-daily-121">[c]</a> </th> <th scope="col" style="width=100px;"><abbr title="Testosterone suppression dose">TSD</abbr><a href="#cite_note-daily-121">[c]</a> </th></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol (non-micronized)</a> </th> <td>30</td> <td>≥120–300</td> <td>120</td> <td>6</td> <td>-</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol (micronized)</a> </th> <td>6–12</td> <td>60–80</td> <td>14–42</td> <td>1–2</td> <td>>5</td> <td>>8 </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Estradiol_valerate" title="Estradiol valerate">Estradiol valerate</a> </th> <td>6–12</td> <td>60–80</td> <td>14–42</td> <td>1–2</td> <td>-</td> <td>>8 </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">Estradiol benzoate</a> </th> <td>-</td> <td>60–140</td> <td>-</td> <td>-</td> <td>-</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Estriol_(medication)" title="Estriol (medication)">Estriol</a> </th> <td>≥20</td> <td>120–150<a href="#cite_note-div-122">[d]</a></td> <td>28–126</td> <td>1–6</td> <td>>5</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Estriol_succinate" title="Estriol succinate">Estriol succinate</a> </th> <td>-</td> <td>140–150<a href="#cite_note-div-122">[d]</a></td> <td>28–126</td> <td>2–6</td> <td>-</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Estrone_sulfate_(medication)" title="Estrone sulfate (medication)">Estrone sulfate</a> </th> <td>12</td> <td>60</td> <td>42</td> <td>2</td> <td>-</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a> </th> <td>5–12</td> <td>60–80</td> <td>8.4–25</td> <td>0.625–1.25</td> <td>>3.75</td> <td>7.5 </td></tr> <tr> <th scope="row" style="background: #f8f9fa;">Ethinylestradiol </th> <td>200 μg</td> <td>1–2</td> <td>280 μg</td> <td>20–40 μg</td> <td>100 μg</td> <td>100 μg </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Mestranol" title="Mestranol">Mestranol</a> </th> <td>300 μg</td> <td>1.5–3.0</td> <td>300–600 μg</td> <td>25–30 μg</td> <td>>80 μg</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Quinestrol" title="Quinestrol">Quinestrol</a> </th> <td>300 μg</td> <td>2–4</td> <td>500 μg</td> <td>25–50 μg</td> <td>-</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Methylestradiol" title="Methylestradiol">Methylestradiol</a> </th> <td>-</td> <td>2</td> <td>-</td> <td>-</td> <td>-</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a> </th> <td>2.5</td> <td>20–30</td> <td>11</td> <td>0.5–2.0</td> <td>>5</td> <td>3 </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Diethylstilbestrol_dipropionate" title="Diethylstilbestrol dipropionate">DES dipropionate</a> </th> <td>-</td> <td>15–30</td> <td>-</td> <td>-</td> <td>-</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Dienestrol" title="Dienestrol">Dienestrol</a> </th> <td>5</td> <td>30–40</td> <td>42</td> <td>0.5–4.0</td> <td>-</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Dienestrol_diacetate" title="Dienestrol diacetate">Dienestrol diacetate</a> </th> <td>3–5</td> <td>30–60</td> <td>-</td> <td>-</td> <td>-</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Hexestrol" title="Hexestrol">Hexestrol</a> </th> <td>-</td> <td>70–110</td> <td>-</td> <td>-</td> <td>-</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Chlorotrianisene" title="Chlorotrianisene">Chlorotrianisene</a> </th> <td>-</td> <td>>100</td> <td>-</td> <td>-</td> <td>>48</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Methallenestril" title="Methallenestril">Methallenestril</a> </th> <td>-</td> <td>400</td> <td>-</td> <td>-</td> <td>-</td> <td>- </td></tr> <tr class="sortbottom"> <td colspan="8" style="width: 1px; background-color:#eaecf0; text-align: center;"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1214851843"><div class="hidden-begin mw-collapsible mw-collapsed" style=""><div class="hidden-title skin-nightmode-reset-color" style="text-align:center;">Sources and footnotes:</div><div class="hidden-content mw-collapsible-content" style=""> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-118"><a href="#cite_ref-118">^</a> <a href="#cite_note-pmid2215269-99">[99]</a><a href="#cite_note-pmid559617-100">[100]</a><a href="#cite_note-WolfSchneider2013-101">[101]</a><a href="#cite_note-GöretzlehnerLauritzen2012-102">[102]</a><a href="#cite_note-KnörrBeller2013-103">[103]</a><a href="#cite_note-HorskyPresl1981-104">[104]</a> <a href="#cite_note-Pschyrembel1968-105">[105]</a><a href="#cite_note-pmid779393-106">[106]</a><a href="#cite_note-Lauritzen1975-107">[107]</a><a href="#cite_note-Kopera1991-108">[108]</a> <a href="#cite_note-pmid29603164-109">[109]</a><a href="#cite_note-pmid29756046-110">[110]</a><a href="#cite_note-Rydén1950-111">[111]</a><a href="#cite_note-pmid14902290-112">[112]</a><a href="#cite_note-Kottmeier1947-113">[113]</a><a href="#cite_note-RietbrockStaib2013-114">[114]</a><a href="#cite_note-Greenblatt1966-115">[115]</a><a href="#cite_note-HerrRevesz1970-116">[116]</a><a href="#cite_note-pmid13370006-117">[117]</a> </li> </ol></div></div><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626"><div class="reflist reflist-lower-alpha"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-119"><a href="#cite_ref-119">^</a> Dosages are given in milligrams unless otherwise noted. </li> <li id="cite_note-2-3-120">^ <a href="#cite_ref-2-3_120-0">a</a> <a href="#cite_ref-2-3_120-1">b</a> <a href="#cite_ref-2-3_120-2">c</a> Dosed every 2 to 3 weeks </li> <li id="cite_note-daily-121">^ <a href="#cite_ref-daily_121-0">a</a> <a href="#cite_ref-daily_121-1">b</a> <a href="#cite_ref-daily_121-2">c</a> Dosed daily </li> <li id="cite_note-div-122">^ <a href="#cite_ref-div_122-0">a</a> <a href="#cite_ref-div_122-1">b</a> In divided doses, 3x/day; irregular and atypical proliferation. </li> </ol></div></div></div></div> </td></tr></tbody></table> <div class="mw-heading mw-heading4"><h4 id="Antiandrogenic_and_antigonadotropic_effects">Antiandrogenic and antigonadotropic effects</h4>[<a href="/w/index.php?title=Ethinylestradiol&action=edit&section=15" title="Edit section: Antiandrogenic and antigonadotropic effects">edit</a>]</div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Testosterone_levels_with_different_estrogen_therapies_in_men_with_prostate_cancer.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f6/Testosterone_levels_with_different_estrogen_therapies_in_men_with_prostate_cancer.png/300px-Testosterone_levels_with_different_estrogen_therapies_in_men_with_prostate_cancer.png" decoding="async" width="300" height="198" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f6/Testosterone_levels_with_different_estrogen_therapies_in_men_with_prostate_cancer.png/450px-Testosterone_levels_with_different_estrogen_therapies_in_men_with_prostate_cancer.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f6/Testosterone_levels_with_different_estrogen_therapies_in_men_with_prostate_cancer.png/600px-Testosterone_levels_with_different_estrogen_therapies_in_men_with_prostate_cancer.png 2x" data-file-width="2046" data-file-height="1348" /></a><figcaption>Testosterone levels with no treatment and with various estrogens in men with prostate cancer.<a href="#cite_note-pmid4359746-123">[118]</a> Determinations were made with an early <a href="/wiki/Radioimmunoassay" title="Radioimmunoassay">radioimmunoassay</a> (RIA).<a href="#cite_note-pmid4359746-123">[118]</a> Source was Shearer et al. (1973).<a href="#cite_note-pmid4359746-123">[118]</a></figcaption></figure> EE is a potent functional <a href="/wiki/Antiandrogen" title="Antiandrogen">antiandrogen</a> in both women and men.<a href="#cite_note-Ekback2017-124">[119]</a> It mediates its antiandrogenic effects by 1) stimulating the <a href="/wiki/Biosynthesis" title="Biosynthesis">production</a> of <a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin">sex hormone-binding globulin</a> (SHBG) in the <a href="/wiki/Liver" title="Liver">liver</a>, which decreases free and thus bioactive concentrations of testosterone in the blood; and by 2) suppressing <a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone">luteinizing hormone</a> (LH) <a href="/wiki/Secretion" title="Secretion">secretion</a> from the <a href="/wiki/Pituitary_gland" title="Pituitary gland">pituitary gland</a>, which decreases production of testosterone by the <a href="/wiki/Gonad" title="Gonad">gonads</a>.<a href="#cite_note-Ekback2017-124">[119]</a><a href="#cite_note-NieschlagBehre2012-125">[120]</a><a href="#cite_note-HumansOrganization2007-27">[27]</a><a href="#cite_note-pmid22294742-126">[121]</a> Birth control pills that contain EE are useful in the treatment of <a href="/wiki/Androgen-dependent_condition" title="Androgen-dependent condition">androgen-dependent conditions</a> like <a href="/wiki/Acne" title="Acne">acne</a> and <a href="/wiki/Hirsutism" title="Hirsutism">hirsutism</a> by virtue of their antiandrogenic effects.<a href="#cite_note-Ekback2017-124">[119]</a><a href="#cite_note-pmid18338653-127">[122]</a> Birth control pills containing EE have been found in women to reduce total testosterone levels by 30% on average, to increase circulating SHBG levels by about 3-fold on average (but variable depending on progestin, range 1.5- to 5-fold increase), and to reduce free testosterone concentrations by 60% on average (range 40 to 80%).<a href="#cite_note-pmid24082040-128">[123]</a><a href="#cite_note-pmid12047300-57">[57]</a><a href="#cite_note-pmid37419659-129">[124]</a><a href="#cite_note-HumansOrganization2007-27">[27]</a> Birth control pills containing high doses of EE can increase SHBG levels in women by as much as 5- to 10-fold.<a href="#cite_note-WintersHuhtaniemi2017-60">[60]</a> This is similar to the 5- to 10-fold increase in SHBG levels that occurs during <a href="/wiki/Pregnancy" title="Pregnancy">pregnancy</a>.<a href="#cite_note-WintersHuhtaniemi2017-60">[60]</a> Due to the marked increase in SHBG levels, free testosterone levels become very low during treatment with EE-containing birth control pills.<a href="#cite_note-pmid23375353-10">[10]</a> In men, a study found that treatment with a relatively low dosage of 20 μg/day EE for five weeks increased circulating SHBG levels by 150% and, due to the accompanying decrease in free testosterone levels, increased total circulating levels of testosterone by 50% (via upregulation of gonadal testosterone production due to reduced <a href="/wiki/Negative_feedback" title="Negative feedback">negative feedback</a> by androgens on the <a href="/wiki/Hypothalamic%E2%80%93pituitary%E2%80%93gonadal_axis" title="Hypothalamic–pituitary–gonadal axis">hypothalamic–pituitary–gonadal axis</a>).<a href="#cite_note-NieschlagBehre2012-125">[120]</a> The stimulation of hepatic SHBG production by EE is far stronger than with other estrogens like estradiol, owing to the high resistance of EE to inactivation in the liver and hence its disproportionate effects in this part of the body.<a href="#cite_note-pmid16112947-7">[7]</a><a href="#cite_note-pmid23375353-10">[10]</a><a href="#cite_note-pmid22950535-130">[125]</a> Estrogens are <a href="/wiki/Antigonadotropin" title="Antigonadotropin">antigonadotropins</a> and are able to suppress the secretion of LH and FSH from the pituitary gland and by extension gonadal testosterone production.<a href="#cite_note-pmid7000222-131">[126]</a><a href="#cite_note-pmid3217277-132">[127]</a> <a href="/wiki/High-dose_estrogen" class="mw-redirect" title="High-dose estrogen">High-dose estrogen</a> therapy, including with EE, is able to suppress testosterone levels in men by around 95%, or into the castrate/female range.<a href="#cite_note-pmid2630306-133">[128]</a><a href="#cite_note-pmid7000222-131">[126]</a><a href="#cite_note-pmid3217277-132">[127]</a> The dosage of EE required for use as a component of <a href="/wiki/Transgender_hormone_therapy_(male-to-female)" class="mw-redirect" title="Transgender hormone therapy (male-to-female)">hormone therapy</a> for preoperative <a href="/wiki/Transgender_women" class="mw-redirect" title="Transgender women">transgender women</a> is 50 to 100 μg/day.<a href="#cite_note-JamesonGroot2010-134">[129]</a> This high dosage is associated with a high incidence of VTE, particularly in those over the age of 40 years, and it has been said that it should not be used.<a href="#cite_note-JamesonGroot2010-134">[129]</a> The dosage of EE used in the treatment of prostate cancer in men is 150 to 1,000 μg/day (0.15–1.0 mg/day).<a href="#cite_note-OettelSchillinger2012-8">[8]</a><a href="#cite_note-DenisGriffiths1999-135">[130]</a> A dosage of EE of 50 μg twice daily (100 μg/day total) has been found to suppress testosterone levels in men to an equivalent extent as 3 mg/day oral <a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">diethylstilbestrol</a>, which is the minimum dosage of diethylstilbestrol required to consistently suppress testosterone levels into the castrate range.<a href="#cite_note-pmid29603164b-136">[131]</a> The ovulation-inhibiting dose of EE by itself and not in combination with a progestin in women is 100 μg/day.<a href="#cite_note-pmid4568621-137">[132]</a><a href="#cite_note-RietbrockStaib2013b-138">[133]</a> However, it has been found to be about 75 to 90% effective at inhibiting ovulation at a dosage of 20 μg/day and about 97 or 98% effective at a dosage of 50 μg/day.<a href="#cite_note-Elger1972-139">[134]</a><a href="#cite_note-BastianelliFarris2018-140">[135]</a><a href="#cite_note-Greenblatt1966b-141">[136]</a><a href="#cite_note-HerrRevesz1970k-142">[137]</a> In another study, ovulation occurred in 25.2% with an EE dose of 50 μg/day.<a href="#cite_note-pmid1146927-143">[138]</a> Lower dosages of EE also have significant antigonadotropic effects.<a href="#cite_note-JamesonGroot2010-134">[129]</a> A "very low" dosage of 15 μg/day EE has been described as the "borderline" amount required for suppression of LH and testosterone levels in men, and a study found that LH and testosterone levels were "reliably" suppressed in men by a dosage of 30 μg/day EE.<a href="#cite_note-OettelSchillinger2012-8">[8]</a> However, other clinical studies have found that 20 μg/day EE increased testosterone levels by 50% in men (as described above)<a href="#cite_note-NieschlagBehre2012-125">[120]</a> and that dosages of 32 μg/day and 42 μg/day EE suppressed FSH levels in men but did not significantly affect LH levels.<a href="#cite_note-OettelSchillinger2012-8">[8]</a> A stronger suppression of testosterone levels was observed in men following daily treatment with a combined oral contraceptive containing 50 μg ethinylestradiol and 0.5 mg <a href="/wiki/Norgestrel" title="Norgestrel">norgestrel</a> for 9 days.<a href="#cite_note-OettelSchillinger2012-8">[8]</a> However, investigation revealed that the progestin was the more important component responsible for the suppression in testosterone levels.<a href="#cite_note-OettelSchillinger2012-8">[8]</a> In accordance, the progestin component of COCs is primarily responsible for inhibition of <a href="/wiki/Ovulation" title="Ovulation">ovulation</a> in women.<a href="#cite_note-OettelSchillinger2012-8">[8]</a> A combination of 20 μg/day EE and 10 mg/day <a href="/wiki/Methyltestosterone" title="Methyltestosterone">methyltestosterone</a> was found to suppress FSH secretion in men to an extent sufficient to stop <a href="/wiki/Spermatogenesis" title="Spermatogenesis">spermatogenesis</a>.<a href="#cite_note-OettelSchillinger2012-8">[8]</a> Studies in women have found that 50 μg/day EE suppresses LH and FSH levels both by about 70% in postmenopausal women.<a href="#cite_note-pmid6291391-98">[98]</a> In addition to its antigonadotropic effects, EE can significantly suppress androgen production by the <a href="/wiki/Adrenal_gland" title="Adrenal gland">adrenal glands</a> at high concentrations.<a href="#cite_note-OettelSchillinger2012-8">[8]</a><a href="#cite_note-MargiorisChrousos2001-144">[139]</a><a href="#cite_note-pmid7586614-145">[140]</a> One study found that treatment with a high dosage of 100 μg/day EE suppressed circulating <a href="/wiki/Adrenal_androgen" class="mw-redirect" title="Adrenal androgen">adrenal androgen</a> levels by 27 to 48% in transgender women.<a href="#cite_note-OettelSchillinger2012-8">[8]</a><a href="#cite_note-MargiorisChrousos2001-144">[139]</a><a href="#cite_note-pmid7586614-145">[140]</a> This may additionally contribute to suppression of androgen levels by estrogens.<a href="#cite_note-OettelSchillinger2012-8">[8]</a><a href="#cite_note-MargiorisChrousos2001-144">[139]</a><a href="#cite_note-pmid7586614-145">[140]</a> <div class="mw-heading mw-heading4"><h4 id="Effects_on_liver_protein_synthesis">Effects on liver protein synthesis</h4>[<a href="/w/index.php?title=Ethinylestradiol&action=edit&section=16" title="Edit section: Effects on liver protein synthesis">edit</a>]</div> EE has marked effects on <a href="/wiki/Liver_protein_synthesis" class="mw-redirect" title="Liver protein synthesis">liver protein synthesis</a>, even at low dosages and regardless of <a href="/wiki/Route_of_administration" title="Route of administration">route of administration</a>.<a href="#cite_note-OettelSchillinger2012-8">[8]</a><a href="#cite_note-pmid16112947-7">[7]</a> These effects are mediated by its estrogenic activity.<a href="#cite_note-OettelSchillinger2012-8">[8]</a><a href="#cite_note-pmid16112947-7">[7]</a> The medication dose-dependently increases circulating levels of SHBG, <a href="/wiki/Corticosteroid-binding_globulin" class="mw-redirect" title="Corticosteroid-binding globulin">corticosteroid-binding globulin</a> (CBG), and <a href="/wiki/Thyroxine-binding_globulin" title="Thyroxine-binding globulin">thyroxine-binding globulin</a> (TBG), and also affects a broad range of other liver proteins.<a href="#cite_note-OettelSchillinger2012-8">[8]</a><a href="#cite_note-pmid16112947-7">[7]</a> EE affects <a href="/wiki/Triglyceride" title="Triglyceride">triglyceride</a> levels at a dose as low as 1 μg/day and <a href="/wiki/LDL_cholesterol" class="mw-redirect" title="LDL cholesterol">LDL</a> and <a href="/wiki/HDL_cholesterol" class="mw-redirect" title="HDL cholesterol">HDL cholesterol</a> levels at a dose as low as 2.5 μg/day.<a href="#cite_note-pmid22244780-146">[141]</a> EE affects several hepatic proteins at a dosage as low as 5 μg/day.<a href="#cite_note-OettelSchillinger2012-8">[8]</a> At doses above 20 μg/day, the incremental effects of EE on liver protein synthesis become continuously smaller.<a href="#cite_note-OettelSchillinger2012-8">[8]</a> EE at 5 μg/day has been found to increase SHBG levels by 100% in postmenopausal women, while a dosage of 20 μg/day EE increased them by 200%.<a href="#cite_note-OettelSchillinger2012-8">[8]</a> Androgens decrease hepatic SHBG production, and have been found to oppose the effects of EE on SHBG levels.<a href="#cite_note-OettelSchillinger2012-8">[8]</a> This is of particular relevance when it is considered that many progestins used in COCs have varying degrees of weak androgenic activity.<a href="#cite_note-OettelSchillinger2012-8">[8]</a> A combination of 20 μg/day EE and 0.25 mg/day <a href="/wiki/Levonorgestrel" title="Levonorgestrel">levonorgestrel</a>, a progestin with relatively high androgenicity, decreases SHBG levels by 50%; 30 μg/day EE and 0.25 mg/day levonorgestrel has no effect on SHBG levels; 30 μg/day EE and 0.15 mg/day levonorgestrel increases SHBG levels by 30%; and <a href="/wiki/Triphasic" class="mw-redirect" title="Triphasic">triphasic</a> COCs containing EE and levonorgestrel increase SHBG levels by 100 to 150%.<a href="#cite_note-OettelSchillinger2012-8">[8]</a> The combination of 30 μg/day EE and 150 μg/day <a href="/wiki/Desogestrel" title="Desogestrel">desogestrel</a>, a progestin with relatively weak androgenicity than levonorgestrel, increases SHBG levels by 200%, while the combination of 35 μg/day EE and 2 mg/day <a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">cyproterone acetate</a>, a progestin with potent <a href="/wiki/Antiandrogen" title="Antiandrogen">antiandrogenic</a> activity, increases SHBG levels by 400%.<a href="#cite_note-OettelSchillinger2012-8">[8]</a> As such, the type and dosage of progestin contained in COCs potently moderates the effects of EE on SHBG levels.<a href="#cite_note-OettelSchillinger2012-8">[8]</a> A dosage of 10 μg/day EE has been found to increase CBG levels by 50%, while a dosage of 20 μg/day EE increased them by 100%.<a href="#cite_note-OettelSchillinger2012-8">[8]</a> Progestins that are progesterone derivatives have no effect on CBG levels, while androgenic progestins like the <a href="/wiki/19-nortestosterone" class="mw-redirect" title="19-nortestosterone">19-nortestosterone</a> derivatives have only a weak effect on CBG levels.<a href="#cite_note-OettelSchillinger2012-8">[8]</a> COCs may increase CBG levels by 100 to 150%.<a href="#cite_note-OettelSchillinger2012-8">[8]</a> A dosage of 5 μg/day EE has been found to increase TBG levels by 40%, while a dosage of 20 μg/day EE increased them by 60%.<a href="#cite_note-OettelSchillinger2012-8">[8]</a> Progestins that are progesterone derivatives do not affect TBG levels, while progestins with androgenic activity may decrease TBG levels.<a href="#cite_note-OettelSchillinger2012-8">[8]</a> A combination of 30 μg/day EE and 1 mg/day <a href="/wiki/Norethisterone" title="Norethisterone">norethisterone</a>, a moderately androgenic progestin, have been found to increase TBG levels by 50 to 70%, while the combination of 30 μg/day EE and 150 μg/day desogestrel increased them by 100%.<a href="#cite_note-OettelSchillinger2012-8">[8]</a> <div class="mw-heading mw-heading4"><h4 id="Differences_from_estradiol">Differences from estradiol</h4>[<a href="/w/index.php?title=Ethinylestradiol&action=edit&section=17" title="Edit section: Differences from estradiol">edit</a>]</div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Levels_of_estrogen-sensitive_proteins_with_oral_estradiol_valerate_and_ethinylestradiol_in_postmenopausal_women.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/13/Levels_of_estrogen-sensitive_proteins_with_oral_estradiol_valerate_and_ethinylestradiol_in_postmenopausal_women.png/375px-Levels_of_estrogen-sensitive_proteins_with_oral_estradiol_valerate_and_ethinylestradiol_in_postmenopausal_women.png" decoding="async" width="375" height="342" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/13/Levels_of_estrogen-sensitive_proteins_with_oral_estradiol_valerate_and_ethinylestradiol_in_postmenopausal_women.png/563px-Levels_of_estrogen-sensitive_proteins_with_oral_estradiol_valerate_and_ethinylestradiol_in_postmenopausal_women.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/13/Levels_of_estrogen-sensitive_proteins_with_oral_estradiol_valerate_and_ethinylestradiol_in_postmenopausal_women.png/750px-Levels_of_estrogen-sensitive_proteins_with_oral_estradiol_valerate_and_ethinylestradiol_in_postmenopausal_women.png 2x" data-file-width="1231" data-file-height="1124" /></a><figcaption>Changes in levels of estrogen-sensitive proteins after treatment with oral estradiol or oral ethinylestradiol in postmenopausal women.<a href="#cite_note-pmid2664738-64">[64]</a><a href="#cite_note-pmid3817605-65">[65]</a> FSH is a pituitary protein and represents general/systemic estrogenic effect, while SHBG and <a href="/wiki/Pregnancy_zone_protein" title="Pregnancy zone protein"><abbr title="pregnancy zone protein">PZP</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip pregnancy zone protein are hepatic proteins and represent liver estrogenic effect.<a href="#cite_note-pmid2664738-64">[64]</a><a href="#cite_note-pmid3817605-65">[65]</a></figcaption></figure> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:SHBG_levels_with_polyestradiol_phosphate,_ethinylestradiol,_and_orchiectomy.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/db/SHBG_levels_with_polyestradiol_phosphate%2C_ethinylestradiol%2C_and_orchiectomy.png/400px-SHBG_levels_with_polyestradiol_phosphate%2C_ethinylestradiol%2C_and_orchiectomy.png" decoding="async" width="400" height="271" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/db/SHBG_levels_with_polyestradiol_phosphate%2C_ethinylestradiol%2C_and_orchiectomy.png/600px-SHBG_levels_with_polyestradiol_phosphate%2C_ethinylestradiol%2C_and_orchiectomy.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/db/SHBG_levels_with_polyestradiol_phosphate%2C_ethinylestradiol%2C_and_orchiectomy.png/800px-SHBG_levels_with_polyestradiol_phosphate%2C_ethinylestradiol%2C_and_orchiectomy.png 2x" data-file-width="1653" data-file-height="1119" /></a><figcaption>SHBG levels in men with 1) intramuscular injection of 320 mg <a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">polyestradiol phosphate</a> once every 4 weeks alone; 2) the combination of intramuscular injection of 80 mg polyestradiol phosphate once every 4 weeks plus 150 μg/day oral ethinylestradiol; 3) orchiectomy only.<a href="#cite_note-pmid3242384-63">[63]</a></figcaption></figure> EE shows strong and disproportionate effects on <a href="/wiki/Liver_protein_synthesis" class="mw-redirect" title="Liver protein synthesis">liver protein synthesis</a> relative to estradiol.<a href="#cite_note-pmid16112947-7">[7]</a> The <a href="/wiki/Liver" title="Liver">liver</a> as well as the <a href="/wiki/Uterus" title="Uterus">uterus</a> express <a href="/wiki/17%CE%B2-hydroxysteroid_dehydrogenase" class="mw-redirect" title="17β-hydroxysteroid dehydrogenase">17β-hydroxysteroid dehydrogenase</a> (17β-HSD), and this <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> serves to inactivate estradiol and effectively suppress its potency in these tissues by reversibly converting it into the far less potent estrogen <a href="/wiki/Estrone_(medication)" title="Estrone (medication)">estrone</a> (which has approximately 4% of the estrogenic activity of estradiol).<a href="#cite_note-pmid16112947-7">[7]</a> In contrast to estradiol, the 17α-ethynyl group of EE prevents <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidation</a> of the C17β position of EE by 17β-HSD, and for this reason, EE is not inactivated in these tissues and has much stronger relative estrogenic activity in them.<a href="#cite_note-pmid16112947-7">[7]</a><a href="#cite_note-Lobo2007-147">[142]</a><a href="#cite_note-Shellenberger1986-11">[11]</a> This is the mechanism of the disproportionately strong effects of EE on hepatic protein production,<a href="#cite_note-pmid16112947-7">[7]</a><a href="#cite_note-Lobo2007-147">[142]</a> which results in a greatly increased magnitude of effect on VTE and cardiovascular risks relative to estradiol.<a href="#cite_note-Shoupe2011-148">[143]</a> On the other hand, due to the loss of inactivation of EE by 17β-HSD in the <a href="/wiki/Endometrium" title="Endometrium">endometrium</a> (uterus), EE is relatively more active than estradiol in the endometrium and, for this reason, is associated with a significantly lower incidence of <a href="/wiki/Vaginal_bleeding" title="Vaginal bleeding">vaginal bleeding and spotting</a> in comparison.<a href="#cite_note-pmid16112947-7">[7]</a> This is particularly so in the case of combined estrogen and progestogen therapy (as in COCs or menopausal HRT), as progestogens induce the expression of 17β-HSD in the endometrium.<a href="#cite_note-pmid16112947-7">[7]</a> The reduced vaginal bleeding and spotting with EE is one of the main reasons that it is used in COCs instead of estradiol,<a href="#cite_note-pmid22468839-3">[3]</a> in spite of its potentially inferior safety profile (related to its adverse effects on hepatic protein synthesis and VTE incidence).<a href="#cite_note-pmid21538049-149">[144]</a> EE has been found to have disproportionate effects on liver protein synthesis and VTE risk regardless of whether the <a href="/wiki/Route_of_administration" title="Route of administration">route of administration</a> is oral, transdermal, or vaginal, indicating that the use of <a href="/wiki/Parenteral" class="mw-redirect" title="Parenteral">parenteral</a> routes over the oral route does not result in EE having proportional hepatic actions relative to non-hepatic actions.<a href="#cite_note-Lobo2007-147">[142]</a><a href="#cite_note-OettelSchillinger2012-8">[8]</a> However, the potency of EE on liver protein synthesis is in any case reduced with parenteral administration.<a href="#cite_note-OettelSchillinger2012-8">[8]</a> A dosage of 10 μg/day vaginal EE has been found to be equivalent to 50 μg oral EE in terms of effects on liver protein synthesis, such as stimulation of hepatic SHBG production.<a href="#cite_note-OettelSchillinger2012-8">[8]</a> As such, parenteral EE, which bypasses the first pass through the liver that occurs with oral EE, has been found to have a 5-fold lower impact on liver protein synthesis by weight than oral EE.<a href="#cite_note-OettelSchillinger2012-8">[8]</a> In contrast to EE as well as to oral estradiol, transdermal estradiol shows few or no effects on liver protein synthesis at typical menopausal dosages.<a href="#cite_note-pmid16112947-7">[7]</a> <table class="wikitable"> <caption>Comparison of estradiol and ethinylestradiol </caption> <tbody><tr> <th>Parameters</th> <th><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a></th> <th>Ethinylestradiol </th></tr> <tr> <td><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor <a href="/wiki/Affinity_(pharmacology)" class="mw-redirect" title="Affinity (pharmacology)">affinity</a></td> <td>1 × 1010 M-1</td> <td>2–5 × 1011 M-1 </td></tr> <tr> <td>Nuclear retention</td> <td>6–8 hours</td> <td>24 hours </td></tr> <tr> <td><a href="/wiki/Elimination_half-life" class="mw-redirect" title="Elimination half-life">Elimination half-life</a></td> <td>90 minutes</td> <td>7 hours </td></tr> <tr> <td><a href="/wiki/Substrate_(biochemistry)" class="mw-redirect" title="Substrate (biochemistry)">Substrate</a> for <a href="/wiki/17%CE%B2-hydroxysteroid_dehydrogenase" class="mw-redirect" title="17β-hydroxysteroid dehydrogenase"><abbr title="17β-hydroxysteroid dehydrogenase">17β-HSD</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip 17β-hydroxysteroid dehydrogenase?</td> <td>Yes</td> <td>No </td></tr> <tr> <td><a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">Bound</a> to <a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin"><abbr title="Sex hormone-binding globulin">SHBG</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Sex hormone-binding globulin?</td> <td>Yes</td> <td>No </td></tr> <tr> <td>Relative <a href="/wiki/Oral_administration" title="Oral administration">oral</a> <a href="/wiki/Liver" title="Liver">liver</a> <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potency</a></td> <td>1</td> <td>~500–1,500 </td></tr> <tr> <td>Relative <a href="/wiki/Oral_administration" title="Oral administration">oral</a> <a href="/wiki/Pituitary_gland" title="Pituitary gland">pituitary</a> potency</td> <td>1</td> <td>200 </td></tr> <tr class="sortbottom"> <td colspan="3" style="width: 1px; background-color:#eaecf0; text-align: center;">Sources:<a href="#cite_note-pmid2664738-64">[64]</a> </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Pharmacokinetics">Pharmacokinetics</h3>[<a href="/w/index.php?title=Ethinylestradiol&action=edit&section=18" title="Edit section: Pharmacokinetics">edit</a>]</div> <div class="mw-heading mw-heading4"><h4 id="Absorption">Absorption</h4>[<a href="/w/index.php?title=Ethinylestradiol&action=edit&section=19" title="Edit section: Absorption">edit</a>]</div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Ethinylestradiol_levels_following_a_single_20_%C2%B5g_oral_dose_of_ethinylestradiol_in_women.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/Ethinylestradiol_levels_following_a_single_20_%C2%B5g_oral_dose_of_ethinylestradiol_in_women.png/350px-Ethinylestradiol_levels_following_a_single_20_%C2%B5g_oral_dose_of_ethinylestradiol_in_women.png" decoding="async" width="350" height="318" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/Ethinylestradiol_levels_following_a_single_20_%C2%B5g_oral_dose_of_ethinylestradiol_in_women.png/525px-Ethinylestradiol_levels_following_a_single_20_%C2%B5g_oral_dose_of_ethinylestradiol_in_women.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/Ethinylestradiol_levels_following_a_single_20_%C2%B5g_oral_dose_of_ethinylestradiol_in_women.png/700px-Ethinylestradiol_levels_following_a_single_20_%C2%B5g_oral_dose_of_ethinylestradiol_in_women.png 2x" data-file-width="1252" data-file-height="1136" /></a><figcaption>EE levels while <a href="/wiki/Fasting" title="Fasting">fasting</a> or with a high-<a href="/wiki/Fat" title="Fat">fat</a> meal following ingestion of <a href="/wiki/Tablet_(pharmacy)" title="Tablet (pharmacy)">tablets</a> containing a single oral dose of 20 μg EE and 2 mg <a href="/wiki/Norethisterone_acetate" title="Norethisterone acetate">norethisterone acetate</a> in women.<a href="#cite_note-pmid12520628-150">[145]</a><a href="#cite_note-pmid16112947-7">[7]</a></figcaption></figure> The <a href="/wiki/Oral_administration" title="Oral administration">oral</a> <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> of EE is 45% on average, with a wide range of 20% to 74% (though most commonly between 38 and 48%) that is due to high <a href="/wiki/Interindividual_variability" class="mw-redirect" title="Interindividual variability">interindividual variability</a>.<a href="#cite_note-pmid23375353-10">[10]</a><a href="#cite_note-pmid8842581-4">[4]</a> Although relatively low, the oral bioavailability of EE is considerably higher than that of micronized estradiol (5%).<a href="#cite_note-pmid2256522-2">[2]</a><a href="#cite_note-pmid23375353-10">[10]</a> Following a single 20 μg dose of EE in combination with 2 mg <a href="/wiki/Norethisterone_acetate" title="Norethisterone acetate">norethisterone acetate</a> in postmenopausal women, EE concentrations have been found to reach a maximum of 50 pg/mL within an average of 1.5 hours.<a href="#cite_note-pmid16112947-7">[7]</a> Following the first dose, mean levels of EE in general further increase by about 50% until <a href="/wiki/Steady-state_concentration" class="mw-redirect" title="Steady-state concentration">steady-state concentrations</a> are reached;<a href="#cite_note-pmid16112947-7">[7]</a><a href="#cite_note-pmid12520628-150">[145]</a> steady-state is reached after one week of daily administration.<a href="#cite_note-OettelSchillinger2012-8">[8]</a> For comparison, the mean peak levels of estradiol achieved with 2 mg micronized estradiol or <a href="/wiki/Estradiol_valerate" title="Estradiol valerate">estradiol valerate</a> are 40 pg/mL following the first dose and 80 pg/mL after three weeks of administration.<a href="#cite_note-pmid16112947-7">[7]</a> These maximal concentrations of estradiol are in the same range as the concentrations of EE that are produced by an oral dose of EE that is 100 times lower by weight, which is in accordance with the approximately 100-fold increased oral potency of EE relative to estradiol.<a href="#cite_note-GomelMunro1990-94">[94]</a><a href="#cite_note-pmid16112947-7">[7]</a> In accordance with the high interindividual variability in the oral bioavailability of EE, there is a large degree of interindividual variation in EE levels.<a href="#cite_note-pmid16112947-7">[7]</a><a href="#cite_note-DodickSilberstein2016-151">[146]</a> A dosage of EE of 50 μg/day has been found to achieve a wide range of circulating EE levels of about 100 to 2,000 pg/mL.<a href="#cite_note-pmid6342899-152">[147]</a><a href="#cite_note-DodickSilberstein2016-151">[146]</a> Taking EE in combination with a high-<a href="/wiki/Fat" title="Fat">fat</a> meal has been found to significantly decrease its peak concentrations.<a href="#cite_note-pmid12520628-150">[145]</a><a href="#cite_note-pmid16112947-7">[7]</a> EE levels after a single 50 μg dose by intravenous injection are several times higher than levels of EE after a single 50 mg dose given orally.<a href="#cite_note-pmid6342899-152">[147]</a> Besides the difference in levels, the course of elimination is similar for the two routes.<a href="#cite_note-pmid6342899-152">[147]</a> There may be gender-specific differences in the <a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">pharmacokinetics</a> of EE, such that EE may have greater oral potency in women than in men.<a href="#cite_note-OettelSchillinger2012-8">[8]</a> A study found that a combination of 60 μg/day EE and 0.25 mg/day <a href="/wiki/Levonorgestrel" title="Levonorgestrel">levonorgestrel</a> in women and men resulted in peak levels of EE of 495 pg/mL and 251 pg/mL, <a href="/wiki/Area-under-the-curve_level" class="mw-redirect" title="Area-under-the-curve level">area-under-the-curve levels</a> of EE of 6.216 pg/mL/hour and 2.850 pg/mL/hour, and <a href="/wiki/Elimination_half-lives" class="mw-redirect" title="Elimination half-lives">elimination half-lives</a> of 16.5 hours and 10.2 hours, respectively.<a href="#cite_note-OettelSchillinger2012-8">[8]</a> It has been suggested that this phenomenon could represent a "protection mechanism" of males against <a href="/wiki/Xenoestrogen" title="Xenoestrogen">environmental estrogen</a> exposure.<a href="#cite_note-OettelSchillinger2012-8">[8]</a> <div class="mw-heading mw-heading4"><h4 id="Distribution">Distribution</h4>[<a href="/w/index.php?title=Ethinylestradiol&action=edit&section=20" title="Edit section: Distribution">edit</a>]</div> The <a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">plasma protein binding</a> of EE is 97 to 98%, and it is bound almost exclusively to <a href="/wiki/Human_serum_albumin" title="Human serum albumin">albumin</a>.<a href="#cite_note-(Firm)Inc2005-5">[5]</a><a href="#cite_note-pmid16112947-7">[7]</a><a href="#cite_note-pmid23375353-10">[10]</a><a href="#cite_note-NotelovitzKeep2012-153">[148]</a> Unlike estradiol, which binds with high affinity to SHBG, EE has very low affinity for this protein, about 2% of that of estradiol, and hence does not bind to it importantly.<a href="#cite_note-pmid7195405-154">[149]</a> <div class="mw-heading mw-heading4"><h4 id="Metabolism">Metabolism</h4>[<a href="/w/index.php?title=Ethinylestradiol&action=edit&section=21" title="Edit section: Metabolism">edit</a>]</div> Due to high first-pass metabolism in the <a href="/wiki/Intestine" class="mw-redirect" title="Intestine">intestines</a> and <a href="/wiki/Liver" title="Liver">liver</a>, only 1% of an oral dose of an EE appears in the circulation as EE itself.<a href="#cite_note-pmid16112947-7">[7]</a> During first-pass metabolism, EE is extensively <a href="/wiki/Conjugation_(pharmacokinetics)" class="mw-redirect" title="Conjugation (pharmacokinetics)">conjugated</a> via <a href="/wiki/Glucuronidation" title="Glucuronidation">glucuronidation</a> and <a href="/wiki/Sulfation" title="Sulfation">sulfation</a> into the hormonally inert ethinylestradiol <a href="/wiki/Glucuronide" title="Glucuronide">glucuronides</a> and <a href="/wiki/Ethinylestradiol_sulfate" title="Ethinylestradiol sulfate">ethinylestradiol sulfate</a> (EE sulfate), and levels of EE sulfate in circulation are between 6- and 22-fold higher than those of EE.<a href="#cite_note-pmid16112947-7">[7]</a><a href="#cite_note-pmid8842581-4">[4]</a> For comparison, with oral administration of 2 mg micronized estradiol, levels of <a href="/wiki/Estrone_(medication)" title="Estrone (medication)">estrone</a> and <a href="/wiki/Estrone_sulfate_(medication)" title="Estrone sulfate (medication)">estrone sulfate</a> are 4- to 6-fold and 200-fold higher than those of estradiol, respectively.<a href="#cite_note-pmid16112947-7">[7]</a> In contrast to estradiol, EE, due to <a href="/wiki/Steric_hindrance" class="mw-redirect" title="Steric hindrance">steric hindrance</a> by its C17α ethynyl group, is not metabolized or inactivated by 17β-HSD,<a href="#cite_note-Shellenberger1986-11">[11]</a> and this is the primary factor responsible for the dramatically increased potency of oral EE relative to oral estradiol.<a href="#cite_note-pmid16112947-7">[7]</a> EE is also not metabolized into estradiol.<a href="#cite_note-pmid30809949-155">[150]</a> Aside from sulfate conjugation, EE is mainly <a href="/wiki/Metabolism" title="Metabolism">metabolized</a> by <a href="/wiki/Hydroxylation" title="Hydroxylation">hydroxylation</a> into <a href="/wiki/Catechol_estrogen" title="Catechol estrogen">catechol estrogens</a>.<a href="#cite_note-pmid16112947-7">[7]</a> This is mainly by 2-hydroxylation into 2-hydroxy-EE, which is catalyzed primarily by <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a>.<a href="#cite_note-pmid23375353-10">[10]</a> Hydroxylation of EE at the C4, C6α, and C16β positions into 4-, 6α-, and 16β-hydroxy-EE has also been reported, but appears to contribute to its metabolism to only a small extent.<a href="#cite_note-pmid23375353-10">[10]</a> 2- and 4-methoxy-EE are also formed via transformation by <a href="/wiki/Catechol_O-methyltransferase" class="mw-redirect" title="Catechol O-methyltransferase">catechol O-methyltransferase</a> of 2- and 4-hydroxy-EE.<a href="#cite_note-pmid16112947-7">[7]</a> Unlike the case of estradiol, 16α-hydroxylation does not occur with EE, owing to <a href="/wiki/Steric_hindrance" class="mw-redirect" title="Steric hindrance">steric hindrance</a> by its ethynyl group at C17α.<a href="#cite_note-pmid23375353-10">[10]</a><a href="#cite_note-pmid16112947-7">[7]</a> The ethynylation of EE is largely irreversible, and so EE is not metabolized into estradiol, unlike <a href="/wiki/Estradiol_ester" class="mw-redirect" title="Estradiol ester">estradiol esters</a>.<a href="#cite_note-pmid16112947-7">[7]</a> A review found that the range of the reported <a href="/wiki/Elimination_half-life" class="mw-redirect" title="Elimination half-life">elimination half-life</a> of EE in the literature was 13.1 to 27.0 hours.<a href="#cite_note-pmid2256522-2">[2]</a> Another review reported an elimination half-life of EE of 10 to 20 hours.<a href="#cite_note-pmid23375353-10">[10]</a> However, the elimination half-life of EE has also been reported by other sources to be as short as 7 hours<a href="#cite_note-Shellenberger1986-11">[11]</a> and as long as 36 hours.<a href="#cite_note-HughesWaters2016-9">[9]</a> Unlike the case of estradiol, in which there is a rapid rise in its levels and which remain elevated in a plateau-like curve for many hours, levels of EE fall rapidly after peaking.<a href="#cite_note-pmid16112947-7">[7]</a> This is thought to be because estrone and estrone sulfate can be reversibly converted back into estradiol and serve as a hormonally inert reservoir for estradiol, whereas the EE sulfate reservoir for EE is much smaller in comparison.<a href="#cite_note-pmid16112947-7">[7]</a><a href="#cite_note-pmid8842581-4">[4]</a> In any case, due to the formation of EE sulfate, <a href="/wiki/Enterohepatic_recirculation" class="mw-redirect" title="Enterohepatic recirculation">enterohepatic recirculation</a> is involved in the <a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">pharmacokinetics</a> of EE similarly to estradiol, although to a lesser extent.<a href="#cite_note-pmid16112947-7">[7]</a><a href="#cite_note-pmid25099693-156">[151]</a> The contribution of enterohepatic recirculation to total circulating EE levels appears to be 12 to 20% or less, and is not observed consistently.<a href="#cite_note-OettelSchillinger2012-8">[8]</a><a href="#cite_note-pmid25099693-156">[151]</a> A secondary peak in EE levels 10 to 14 hours after administration can often be observed with oral EE.<a href="#cite_note-pmid25099693-156">[151]</a> EE, following <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidative</a> formation of a very reactive <a href="/wiki/Metabolite" title="Metabolite">metabolite</a>, <a href="/wiki/Irreversible_inhibition" class="mw-redirect" title="Irreversible inhibition">irreversibly inhibits</a> <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> <a href="/wiki/Enzyme" title="Enzyme">enzymes</a> involved in its metabolism, and this may also play a role in the increased potency of EE relative to estradiol.<a href="#cite_note-pmid16112947-7">[7]</a> Indeed, EE is said to have a marked effect on hepatic metabolism, and this is one of the reasons, among others, that natural estrogens like estradiol may be preferable.<a href="#cite_note-NotelovitzKeep2012-153">[148]</a> A 2-fold accumulation in EE levels with an EE-containing COC has been observed following 1 year of therapy.<a href="#cite_note-pmid25099693-156">[151]</a> <div class="mw-heading mw-heading4"><h4 id="Elimination">Elimination</h4>[<a href="/w/index.php?title=Ethinylestradiol&action=edit&section=22" title="Edit section: Elimination">edit</a>]</div> EE is <a href="/wiki/Elimination_(pharmacokinetics)" class="mw-redirect" title="Elimination (pharmacokinetics)">eliminated</a> 62% in the <a href="/wiki/Feces" title="Feces">feces</a> and 38% in the <a href="/wiki/Urine" title="Urine">urine</a>.<a href="#cite_note-pmid23375353-10">[10]</a> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2>[<a href="/w/index.php?title=Ethinylestradiol&action=edit&section=23" title="Edit section: Chemistry">edit</a>]</div> EE, also known as 17α-ethynylestradiol or as 17α-ethynylestra-1,3,5(10)-triene-3,17β-diol, is a <a href="/wiki/Synthetic_compound" class="mw-redirect" title="Synthetic compound">synthetic</a> <a href="/wiki/Estrane" title="Estrane">estrane</a> <a href="/wiki/Steroid" title="Steroid">steroid</a> and a <a href="/wiki/Chemical_derivative" class="mw-redirect" title="Chemical derivative">derivative</a> of <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a> with an <a href="/wiki/Ethynyl_group" title="Ethynyl group">ethynyl substitution</a> at the C17α position.<a href="#cite_note-Elks2014-1">[1]</a><a href="#cite_note-IndexNominum2000-157">[152]</a> The 17α-ethynylation of estradiol to create EE is analogous to the 17α-substitution of <a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">testosterone</a> to make testosterone derivatives such as 17α-ethynylated progestins like <a href="/wiki/Ethisterone" title="Ethisterone">ethisterone</a> (17α-ethynyltestosterone) and <a href="/wiki/Norethisterone" title="Norethisterone">norethisterone</a> (17α-ethynyl-19-nortestosterone) as well as <a href="/wiki/17%CE%B1-alkylated_anabolic_steroid" class="mw-redirect" title="17α-alkylated anabolic steroid">17α-alkylated</a> <a href="/wiki/Androgen" title="Androgen">androgens</a>/<a href="/wiki/Anabolic_steroid" title="Anabolic steroid">anabolic steroids</a> like <a href="/wiki/Methyltestosterone" title="Methyltestosterone">methyltestosterone</a> (17α-methyltestosterone). <div class="mw-heading mw-heading3"><h3 id="Analogues">Analogues</h3>[<a href="/w/index.php?title=Ethinylestradiol&action=edit&section=24" title="Edit section: Analogues">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/List_of_estrogens#17α-Substituted_estradiol_derivatives" title="List of estrogens">List of estrogens § 17α-Substituted estradiol derivatives</a></div> A number of <a href="/wiki/Chemical_derivative" class="mw-redirect" title="Chemical derivative">derivatives</a> of EE exist.<a href="#cite_note-Elks2014-1">[1]</a><a href="#cite_note-IndexNominum2000-157">[152]</a> These include <a href="/wiki/Mestranol" title="Mestranol">mestranol</a> (EE 3-methyl ether), <a href="/wiki/Quinestrol" title="Quinestrol">quinestrol</a> (EE 3-cyclopentyl ether), <a href="/wiki/Ethinylestradiol_sulfonate" title="Ethinylestradiol sulfonate">ethinylestradiol sulfonate</a> (EE 3-isopropylsulfonate), and <a href="/wiki/Moxestrol" title="Moxestrol">moxestrol</a> (11β-methoxy-EE).<a href="#cite_note-Elks2014-1">[1]</a><a href="#cite_note-IndexNominum2000-157">[152]</a><a href="#cite_note-OettelSchillinger2012-8">[8]</a> The former three are <a href="/wiki/Prodrug" title="Prodrug">prodrugs</a> of EE, while the latter one is not.<a href="#cite_note-OettelSchillinger2012-8">[8]</a> A few <a href="/wiki/Structural_analog" title="Structural analog">analogues</a> of EE with other <a href="/wiki/Substituent" title="Substituent">substitutions</a> at the C17α position exist.<a href="#cite_note-Elks2014-1">[1]</a><a href="#cite_note-IndexNominum2000-157">[152]</a> Examples include the estradiol derivatives <a href="/wiki/Methylestradiol" title="Methylestradiol">methylestradiol</a> (17α-methylestradiol) and <a href="/wiki/Ethylestradiol" title="Ethylestradiol">ethylestradiol</a> (17α-ethylestradiol), and the <a href="/wiki/Estriol_(medication)" title="Estriol (medication)">estriol</a> derivatives <a href="/wiki/Ethinylestriol" title="Ethinylestriol">ethinylestriol</a> (17α-ethynylestriol) and <a href="/wiki/Nilestriol" title="Nilestriol">nilestriol</a> (17α-ethynylestriol 3-cyclopentyl ether).<a href="#cite_note-Elks2014-1">[1]</a><a href="#cite_note-IndexNominum2000-157">[152]</a> <a href="/wiki/Androstane" title="Androstane">Androstane</a> analogues of EE with significant although weak estrogenic activity include <a href="/wiki/Ethinylandrostenediol" title="Ethinylandrostenediol">ethinylandrostenediol</a> (17α-ethynyl-5-androstenediol), <a href="/wiki/17%CE%B1-ethynyl-3%CE%B2-androstanediol" class="mw-redirect" title="17α-ethynyl-3β-androstanediol">17α-ethynyl-3β-androstanediol</a>, <a href="/wiki/17%CE%B1-ethynyl-3%CE%B1-androstanediol" class="mw-redirect" title="17α-ethynyl-3α-androstanediol">17α-ethynyl-3α-androstanediol</a>, and <a href="/wiki/Methandriol" title="Methandriol">methandriol</a> (17α-methyl-5-androstenediol). <div class="mw-heading mw-heading2"><h2 id="History">History</h2>[<a href="/w/index.php?title=Ethinylestradiol&action=edit&section=25" title="Edit section: History">edit</a>]</div> EE was the first orally active synthetic estrogen and was described in 1938 by Hans Herloff Inhoffen and Walter Hohlweg of <a href="/wiki/Schering_AG" title="Schering AG">Schering AG</a> in <a href="/wiki/Berlin" title="Berlin">Berlin</a>.<a href="#cite_note-Inhoffen_1938-158">[153]</a><a href="#cite_note-Maisel_1965-159">[154]</a><a href="#cite_note-Petrow_1970-160">[155]</a><a href="#cite_note-Sneader_2005-161">[156]</a><a href="#cite_note-Djerassi_2006-162">[157]</a> It was approved by the US <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> (FDA) in June 1943, and marketed by <a href="/wiki/Schering-Plough" title="Schering-Plough">Schering</a> under the brand name Estinyl.<a href="#cite_note-Estinyl_1943-14">[14]</a> The FDA withdrew approval of Estinyl effective 4 June 2004 at the request of <a href="/wiki/Schering_AG" title="Schering AG">Schering</a>, which had discontinued marketing it.<a href="#cite_note-Estinyl_2004-163">[158]</a> EE was never introduced for use by <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">intramuscular injection</a>.<a href="#cite_note-pmid13359169-164">[159]</a> EE was first used in COCs, as an alternative to <a href="/wiki/Mestranol" title="Mestranol">mestranol</a>, in 1964, and shortly thereafter superseded mestranol in COCs.<a href="#cite_note-GruhnKazer2013-15">[15]</a> Early COCs contained 40 to 100 μg/day EE and 50 to 150 μg/day mestranol.<a href="#cite_note-BellerKnörr1974-165">[160]</a><a href="#cite_note-Haller1968-166">[161]</a> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2>[<a href="/w/index.php?title=Ethinylestradiol&action=edit&section=26" title="Edit section: Society and culture">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Generic_names">Generic names</h3>[<a href="/w/index.php?title=Ethinylestradiol&action=edit&section=27" title="Edit section: Generic names">edit</a>]</div> Ethinylestradiol is the <a href="/wiki/English_language" title="English language">English</a> <a href="/wiki/Generic_drug" title="Generic drug">generic name</a> of the drug and its <a href="/wiki/International_Nonproprietary_Name" class="mw-redirect" title="International Nonproprietary Name"><abbr title="International Nonproprietary Name">INN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip International Nonproprietary Name, <a href="/wiki/United_States_Adopted_Name" title="United States Adopted Name"><abbr title="United States Adopted Name">USAN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip United States Adopted Name, <a href="/wiki/British_Approved_Name" title="British Approved Name"><abbr title="British Approved Name">BAN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip British Approved Name, and <a href="/wiki/Japanese_Accepted_Name" title="Japanese Accepted Name"><abbr title="Japanese Accepted Name">JAN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Japanese Accepted Name.<a href="#cite_note-Drugs.com-167">[162]</a><a href="#cite_note-Elks2014-1">[1]</a><a href="#cite_note-MortonHall2012-168">[163]</a><a href="#cite_note-IndexNominum2000-157">[152]</a> It has also been spelled as ethynylestradiol, ethynyloestradiol, and ethinyloestradiol (all having the same pronunciation), and the latter was formerly its <a href="/wiki/British_Approved_Name" title="British Approved Name"><abbr title="British Approved Name">BAN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip British Approved Name but was eventually changed.<a href="#cite_note-Drugs.com-167">[162]</a><a href="#cite_note-Elks2014-1">[1]</a><a href="#cite_note-IndexNominum2000-157">[152]</a> In addition, a space is often included in the name of EE such that it is written as ethinyl estradiol (as well as variations thereof), and this is its <a href="/wiki/United_States_Pharmacopeia" title="United States Pharmacopeia"><abbr title="United States Pharmacopeia">USP</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip United States Pharmacopeia name.<a href="#cite_note-Drugs.com-167">[162]</a><a href="#cite_note-IndexNominum2000-157">[152]</a> The generic name of EE in <a href="/wiki/French_language" title="French language">French</a> and its <a href="/wiki/D%C3%A9nomination_Commune_Fran%C3%A7aise" title="Dénomination Commune Française"><abbr title="Dénomination Commune Française">DCF</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Dénomination Commune Française are éthinylestradiol, in <a href="/wiki/Spanish_language" title="Spanish language">Spanish</a> is etinilestradiol, in <a href="/wiki/Italian_language" title="Italian language">Italian</a> and its <a href="/wiki/Denominazione_Comune_Italiana" title="Denominazione Comune Italiana"><abbr title="Denominazione Comune Italiana">DCIT</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Denominazione Comune Italiana are etinilestradiolo, and in <a href="/wiki/Latin_language" class="mw-redirect" title="Latin language">Latin</a> is ethinylestradiolum.<a href="#cite_note-Drugs.com-167">[162]</a><a href="#cite_note-IndexNominum2000-157">[152]</a> The name of the drug is often abbreviated as EE or as EE2 in the <a href="/wiki/Medical_literature" title="Medical literature">medical literature</a>. <div class="mw-heading mw-heading3"><h3 id="Brand_names">Brand names</h3>[<a href="/w/index.php?title=Ethinylestradiol&action=edit&section=28" title="Edit section: Brand names">edit</a>]</div> EE has been marketed as a standalone oral drug under the brand names Esteed, Estinyl, Feminone, Lynoral, Menolyn, Novestrol, Palonyl, Spanestrin, and Ylestrol among others, although most or all of these formulations are now discontinued.<a href="#cite_note-AMA1977-169">[164]</a><a href="#cite_note-Pharmaceuticals1983-170">[165]</a><a href="#cite_note-IndexNominum2000-157">[152]</a> It is marketed under a very large number of brand names throughout the world in combination with progestins for use as an oral contraceptive.<a href="#cite_note-Drugs.com-167">[162]</a> In addition, EE is marketed in the <abbr title="United States">U.S.</abbr> in combination with <a href="/wiki/Norelgestromin" title="Norelgestromin">norelgestromin</a> under the brand names <a href="/wiki/Ortho_Evra" class="mw-redirect" title="Ortho Evra">Ortho Evra</a> and <a href="/wiki/Xulane" class="mw-redirect" title="Xulane">Xulane</a> as a <a href="/wiki/Contraceptive_patch" title="Contraceptive patch">contraceptive patch</a>, in combination with <a href="/wiki/Etonogestrel" title="Etonogestrel">etonogestrel</a> under the brand name <a href="/wiki/NuvaRing" class="mw-redirect" title="NuvaRing">NuvaRing</a> as a <a href="/wiki/Contraceptive_vaginal_ring" title="Contraceptive vaginal ring">contraceptive vaginal ring</a>, and in combination with <a href="/wiki/Norethisterone_acetate" title="Norethisterone acetate">norethisterone acetate</a> under the brand name <a href="/wiki/FemHRT" class="mw-redirect" title="FemHRT">FemHRT</a> in oral hormone replacement therapy for the treatment of menopausal symptoms.<a href="#cite_note-Drugs@FDA-12">[12]</a> <div class="mw-heading mw-heading3"><h3 id="Availability">Availability</h3>[<a href="/w/index.php?title=Ethinylestradiol&action=edit&section=29" title="Edit section: Availability">edit</a>]</div> Ethinylestradiol is marketed throughout the world.<a href="#cite_note-Drugs.com-167">[162]</a><a href="#cite_note-IndexNominum2000-157">[152]</a> It is marketed exclusively or almost exclusively in combination with progestins.<a href="#cite_note-Drugs.com-167">[162]</a> Combination medications with additional hormones are common medications in the US.<a href="#cite_note-Top_300_of_2022-18">[18]</a> <table class="wikitable"> <caption>Combination medications including ethinylestradiol in 2022<a href="#cite_note-Top_300_of_2022-18">[18]</a> </caption> <tbody><tr> <th>Other components</th> <th>Rank</th> <th>Total prescriptions</th> <th>Additional sources </th></tr> <tr> <td><a href="/wiki/Norethisterone" title="Norethisterone">Norethisterone</a> or <a href="/wiki/Norethisterone_acetate" title="Norethisterone acetate">norethisterone acetate</a></td> <td>80</td> <td>8 million</td> <td><a href="#cite_note-E+N-19">[19]</a> </td></tr> <tr> <td><a href="/wiki/Norgestimate" title="Norgestimate">Norgestimate</a></td> <td>99</td> <td>6 million</td> <td><a href="#cite_note-171">[166]</a> </td></tr> <tr> <td><a href="/wiki/Levonorgestrel" title="Levonorgestrel">Levonorgestrel</a></td> <td>128</td> <td>4 million</td> <td><a href="#cite_note-172">[167]</a> </td></tr> <tr> <td><a href="/wiki/Drospirenone" title="Drospirenone">Drospirenone</a></td> <td>142</td> <td>4 million</td> <td><a href="#cite_note-173">[168]</a> </td></tr> <tr> <td><a href="/wiki/Desogestrel" title="Desogestrel">Desogestrel</a></td> <td>161</td> <td>3 million</td> <td><a href="#cite_note-174">[169]</a> </td></tr> <tr> <td><a href="/wiki/Etonogestrel" title="Etonogestrel">Etonogestrel</a></td> <td>194</td> <td>2 million</td> <td><a href="#cite_note-175">[170]</a> </td></tr> <tr> <td><a href="/wiki/Norgestrel" title="Norgestrel">Norgestrel</a></td> <td>264</td> <td>1 million</td> <td><a href="#cite_note-176">[171]</a> </td></tr> <tr> <td><a href="/wiki/Drospirenone" title="Drospirenone">Drospirenone</a> and <a href="/wiki/Levomefolic_acid" title="Levomefolic acid">levomefolic acid</a></td> <td>285</td> <td>500,000</td> <td><a href="#cite_note-177">[172]</a> </td></tr> <tr> <td><a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">Etynodiol</a></td> <td>294</td> <td>400,000</td> <td><a href="#cite_note-178">[173]</a> </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="References">References</h2>[<a href="/w/index.php?title=Ethinylestradiol&action=edit&section=30" title="Edit section: References">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626"><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-Elks2014-1">^ <a href="#cite_ref-Elks2014_1-0">a</a> <a href="#cite_ref-Elks2014_1-1">b</a> <a href="#cite_ref-Elks2014_1-2">c</a> <a href="#cite_ref-Elks2014_1-3">d</a> <a href="#cite_ref-Elks2014_1-4">e</a> <a href="#cite_ref-Elks2014_1-5">f</a> <a href="#cite_ref-Elks2014_1-6">g</a> <a href="#cite_ref-Elks2014_1-7">h</a> <style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFElks2014" class="citation book cs1">Elks J (14 November 2014). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA522">The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies</a>. Springer. pp. 522–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4757-2085-3" title="Special:BookSources/978-1-4757-2085-3"><bdi>978-1-4757-2085-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Dictionary+of+Drugs%3A+Chemical+Data%3A+Chemical+Data%2C+Structures+and+Bibliographies&rft.pages=522-&rft.pub=Springer&rft.date=2014-11-14&rft.isbn=978-1-4757-2085-3&rft.aulast=Elks&rft.aufirst=J&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D0vXTBwAAQBAJ%26pg%3DPA522&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid2256522-2">^ <a href="#cite_ref-pmid2256522_2-0">a</a> <a href="#cite_ref-pmid2256522_2-1">b</a> <a href="#cite_ref-pmid2256522_2-2">c</a> <a href="#cite_ref-pmid2256522_2-3">d</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGoldzieherBrody1990" class="citation journal cs1">Goldzieher JW, Brody SA (December 1990). "Pharmacokinetics of ethinyl estradiol and mestranol". American Journal of Obstetrics and Gynecology. 163 (6 Pt 2): 2114–2119. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0002-9378%2890%2990550-Q">10.1016/0002-9378(90)90550-Q</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/2256522">2256522</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=American+Journal+of+Obstetrics+and+Gynecology&rft.atitle=Pharmacokinetics+of+ethinyl+estradiol+and+mestranol&rft.volume=163&rft.issue=6+Pt+2&rft.pages=2114-2119&rft.date=1990-12&rft_id=info%3Adoi%2F10.1016%2F0002-9378%2890%2990550-Q&rft_id=info%3Apmid%2F2256522&rft.aulast=Goldzieher&rft.aufirst=JW&rft.au=Brody%2C+SA&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid22468839-3">^ <a href="#cite_ref-pmid22468839_3-0">a</a> <a href="#cite_ref-pmid22468839_3-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFruzzettiTrémollieresBitzer2012" class="citation journal cs1">Fruzzetti F, Trémollieres F, Bitzer J (May 2012). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3399636">"An overview of the development of combined oral contraceptives containing estradiol: focus on estradiol valerate/dienogest"</a>. Gynecological Endocrinology. 28 (5): 400–408. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3109%2F09513590.2012.662547">10.3109/09513590.2012.662547</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3399636">3399636</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/22468839">22468839</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Gynecological+Endocrinology&rft.atitle=An+overview+of+the+development+of+combined+oral+contraceptives+containing+estradiol%3A+focus+on+estradiol+valerate%2Fdienogest&rft.volume=28&rft.issue=5&rft.pages=400-408&rft.date=2012-05&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3399636%23id-name%3DPMC&rft_id=info%3Apmid%2F22468839&rft_id=info%3Adoi%2F10.3109%2F09513590.2012.662547&rft.aulast=Fruzzetti&rft.aufirst=F&rft.au=Tr%C3%A9mollieres%2C+F&rft.au=Bitzer%2C+J&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3399636&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid8842581-4">^ <a href="#cite_ref-pmid8842581_4-0">a</a> <a href="#cite_ref-pmid8842581_4-1">b</a> <a href="#cite_ref-pmid8842581_4-2">c</a> <a href="#cite_ref-pmid8842581_4-3">d</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFotherby1996" class="citation journal cs1">Fotherby K (August 1996). "Bioavailability of orally administered sex steroids used in oral contraception and hormone replacement therapy". Contraception. 54 (2): 59–69. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0010-7824%2896%2900136-9">10.1016/0010-7824(96)00136-9</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/8842581">8842581</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Contraception&rft.atitle=Bioavailability+of+orally+administered+sex+steroids+used+in+oral+contraception+and+hormone+replacement+therapy&rft.volume=54&rft.issue=2&rft.pages=59-69&rft.date=1996-08&rft_id=info%3Adoi%2F10.1016%2F0010-7824%2896%2900136-9&rft_id=info%3Apmid%2F8842581&rft.aulast=Fotherby&rft.aufirst=K&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-(Firm)Inc2005-5">^ <a href="#cite_ref-(Firm)Inc2005_5-0">a</a> <a href="#cite_ref-(Firm)Inc2005_5-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFacts_and_Comparisons_(Firm)Ovid_Technologies,_Inc2005" class="citation book cs1">Facts and Comparisons (Firm), Ovid Technologies, Inc (2005). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=zumzLgzj1CsC&q=ethinyl+estradiol+albumin">Drug Facts and Comparisons 2005: Pocket Version</a>. Facts and Comparisons. p. 121. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-57439-179-4" title="Special:BookSources/978-1-57439-179-4"><bdi>978-1-57439-179-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Drug+Facts+and+Comparisons+2005%3A+Pocket+Version&rft.pages=121&rft.pub=Facts+and+Comparisons&rft.date=2005&rft.isbn=978-1-57439-179-4&rft.au=Facts+and+Comparisons+%28Firm%29&rft.au=Ovid+Technologies%2C+Inc&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DzumzLgzj1CsC%26q%3Dethinyl%2Bestradiol%2Balbumin&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Micromedex2003-6"><a href="#cite_ref-Micromedex2003_6-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMicromedex2003" class="citation book cs1">Micromedex (1 January 2003). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=zEzWtsVl-KgC">USP DI 2003: Drug Information for Healthcare Professionals</a>. Thomson Micromedex. pp. 1253, 1258, 1266. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-56363-429-1" title="Special:BookSources/978-1-56363-429-1"><bdi>978-1-56363-429-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=USP+DI+2003%3A+Drug+Information+for+Healthcare+Professionals&rft.pages=1253%2C+1258%2C+1266&rft.pub=Thomson+Micromedex&rft.date=2003-01-01&rft.isbn=978-1-56363-429-1&rft.au=Micromedex&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DzEzWtsVl-KgC&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid16112947-7">^ <a href="#cite_ref-pmid16112947_7-0">a</a> <a href="#cite_ref-pmid16112947_7-1">b</a> <a href="#cite_ref-pmid16112947_7-2">c</a> <a href="#cite_ref-pmid16112947_7-3">d</a> <a href="#cite_ref-pmid16112947_7-4">e</a> <a href="#cite_ref-pmid16112947_7-5">f</a> <a href="#cite_ref-pmid16112947_7-6">g</a> <a href="#cite_ref-pmid16112947_7-7">h</a> <a href="#cite_ref-pmid16112947_7-8">i</a> <a href="#cite_ref-pmid16112947_7-9">j</a> <a href="#cite_ref-pmid16112947_7-10">k</a> <a href="#cite_ref-pmid16112947_7-11">l</a> <a href="#cite_ref-pmid16112947_7-12">m</a> <a href="#cite_ref-pmid16112947_7-13">n</a> <a href="#cite_ref-pmid16112947_7-14">o</a> <a href="#cite_ref-pmid16112947_7-15">p</a> <a href="#cite_ref-pmid16112947_7-16">q</a> <a href="#cite_ref-pmid16112947_7-17">r</a> <a href="#cite_ref-pmid16112947_7-18">s</a> <a href="#cite_ref-pmid16112947_7-19">t</a> <a href="#cite_ref-pmid16112947_7-20">u</a> <a href="#cite_ref-pmid16112947_7-21">v</a> <a href="#cite_ref-pmid16112947_7-22">w</a> <a href="#cite_ref-pmid16112947_7-23">x</a> <a href="#cite_ref-pmid16112947_7-24">y</a> <a href="#cite_ref-pmid16112947_7-25">z</a> <a href="#cite_ref-pmid16112947_7-26">aa</a> <a href="#cite_ref-pmid16112947_7-27">ab</a> <a href="#cite_ref-pmid16112947_7-28">ac</a> <a href="#cite_ref-pmid16112947_7-29">ad</a> <a href="#cite_ref-pmid16112947_7-30">ae</a> <a href="#cite_ref-pmid16112947_7-31">af</a> <a href="#cite_ref-pmid16112947_7-32">ag</a> <a href="#cite_ref-pmid16112947_7-33">ah</a> <a href="#cite_ref-pmid16112947_7-34">ai</a> <a href="#cite_ref-pmid16112947_7-35">aj</a> <a href="#cite_ref-pmid16112947_7-36">ak</a> <a href="#cite_ref-pmid16112947_7-37">al</a> <a href="#cite_ref-pmid16112947_7-38">am</a> <a href="#cite_ref-pmid16112947_7-39">an</a> <a href="#cite_ref-pmid16112947_7-40">ao</a> <a href="#cite_ref-pmid16112947_7-41">ap</a> <a href="#cite_ref-pmid16112947_7-42">aq</a> <a href="#cite_ref-pmid16112947_7-43">ar</a> <a href="#cite_ref-pmid16112947_7-44">as</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKuhl2005" class="citation journal cs1">Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric. 8 (Suppl 1): 3–63. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F13697130500148875">10.1080/13697130500148875</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16112947">16112947</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:24616324">24616324</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Climacteric&rft.atitle=Pharmacology+of+estrogens+and+progestogens%3A+influence+of+different+routes+of+administration&rft.volume=8&rft.issue=Suppl+1&rft.pages=3-63&rft.date=2005-08&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A24616324%23id-name%3DS2CID&rft_id=info%3Apmid%2F16112947&rft_id=info%3Adoi%2F10.1080%2F13697130500148875&rft.aulast=Kuhl&rft.aufirst=H&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-OettelSchillinger2012-8">^ <a href="#cite_ref-OettelSchillinger2012_8-0">a</a> <a href="#cite_ref-OettelSchillinger2012_8-1">b</a> <a href="#cite_ref-OettelSchillinger2012_8-2">c</a> <a href="#cite_ref-OettelSchillinger2012_8-3">d</a> <a href="#cite_ref-OettelSchillinger2012_8-4">e</a> <a href="#cite_ref-OettelSchillinger2012_8-5">f</a> <a href="#cite_ref-OettelSchillinger2012_8-6">g</a> <a href="#cite_ref-OettelSchillinger2012_8-7">h</a> <a href="#cite_ref-OettelSchillinger2012_8-8">i</a> <a href="#cite_ref-OettelSchillinger2012_8-9">j</a> <a href="#cite_ref-OettelSchillinger2012_8-10">k</a> <a href="#cite_ref-OettelSchillinger2012_8-11">l</a> <a href="#cite_ref-OettelSchillinger2012_8-12">m</a> <a href="#cite_ref-OettelSchillinger2012_8-13">n</a> <a href="#cite_ref-OettelSchillinger2012_8-14">o</a> <a href="#cite_ref-OettelSchillinger2012_8-15">p</a> <a href="#cite_ref-OettelSchillinger2012_8-16">q</a> <a href="#cite_ref-OettelSchillinger2012_8-17">r</a> <a href="#cite_ref-OettelSchillinger2012_8-18">s</a> <a href="#cite_ref-OettelSchillinger2012_8-19">t</a> <a href="#cite_ref-OettelSchillinger2012_8-20">u</a> <a href="#cite_ref-OettelSchillinger2012_8-21">v</a> <a href="#cite_ref-OettelSchillinger2012_8-22">w</a> <a href="#cite_ref-OettelSchillinger2012_8-23">x</a> <a href="#cite_ref-OettelSchillinger2012_8-24">y</a> <a href="#cite_ref-OettelSchillinger2012_8-25">z</a> <a href="#cite_ref-OettelSchillinger2012_8-26">aa</a> <a href="#cite_ref-OettelSchillinger2012_8-27">ab</a> <a href="#cite_ref-OettelSchillinger2012_8-28">ac</a> <a href="#cite_ref-OettelSchillinger2012_8-29">ad</a> <a href="#cite_ref-OettelSchillinger2012_8-30">ae</a> <a href="#cite_ref-OettelSchillinger2012_8-31">af</a> <a href="#cite_ref-OettelSchillinger2012_8-32">ag</a> <a href="#cite_ref-OettelSchillinger2012_8-33">ah</a> <a href="#cite_ref-OettelSchillinger2012_8-34">ai</a> <a href="#cite_ref-OettelSchillinger2012_8-35">aj</a> <a href="#cite_ref-OettelSchillinger2012_8-36">ak</a> <a href="#cite_ref-OettelSchillinger2012_8-37">al</a> <a href="#cite_ref-OettelSchillinger2012_8-38">am</a> <a href="#cite_ref-OettelSchillinger2012_8-39">an</a> <a href="#cite_ref-OettelSchillinger2012_8-40">ao</a> <a href="#cite_ref-OettelSchillinger2012_8-41">ap</a> <a href="#cite_ref-OettelSchillinger2012_8-42">aq</a> <a href="#cite_ref-OettelSchillinger2012_8-43">ar</a> <a href="#cite_ref-OettelSchillinger2012_8-44">as</a> <a href="#cite_ref-OettelSchillinger2012_8-45">at</a> <a href="#cite_ref-OettelSchillinger2012_8-46">au</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFOettelSchillinger2012" class="citation book cs1">Oettel M, Schillinger E (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=wBvyCAAAQBAJ&pg=PA369">Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen</a>. Springer Science & Business Media. pp. 4, 10, 15, 165, 247–248, 276–291, 363–408, 424, 514, 540, 543, 581. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-60107-1" title="Special:BookSources/978-3-642-60107-1"><bdi>978-3-642-60107-1</bdi></a>. <q>The binding affinity of EE2 for the estrogen receptor is similar to that of estradiol. [...] During daily intake, the EE2 levels increase up to a steady state which is reached after about 1 week.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Estrogens+and+Antiestrogens+II%3A+Pharmacology+and+Clinical+Application+of+Estrogens+and+Antiestrogen&rft.pages=4%2C+10%2C+15%2C+165%2C+247-248%2C+276-291%2C+363-408%2C+424%2C+514%2C+540%2C+543%2C+581&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-3-642-60107-1&rft.aulast=Oettel&rft.aufirst=M&rft.au=Schillinger%2C+E&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DwBvyCAAAQBAJ%26pg%3DPA369&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-HughesWaters2016-9">^ <a href="#cite_ref-HughesWaters2016_9-0">a</a> <a href="#cite_ref-HughesWaters2016_9-1">b</a> <a href="#cite_ref-HughesWaters2016_9-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHughesWaters2016" class="citation book cs1">Hughes CL, Waters MD (23 March 2016). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=5qPWCwAAQBAJ&pg=PA73">Translational Toxicology: Defining a New Therapeutic Discipline</a>. Humana Press. pp. 73–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-319-27449-2" title="Special:BookSources/978-3-319-27449-2"><bdi>978-3-319-27449-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Translational+Toxicology%3A+Defining+a+New+Therapeutic+Discipline&rft.pages=73-&rft.pub=Humana+Press&rft.date=2016-03-23&rft.isbn=978-3-319-27449-2&rft.aulast=Hughes&rft.aufirst=CL&rft.au=Waters%2C+MD&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D5qPWCwAAQBAJ%26pg%3DPA73&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid23375353-10">^ <a href="#cite_ref-pmid23375353_10-0">a</a> <a href="#cite_ref-pmid23375353_10-1">b</a> <a href="#cite_ref-pmid23375353_10-2">c</a> <a href="#cite_ref-pmid23375353_10-3">d</a> <a href="#cite_ref-pmid23375353_10-4">e</a> <a href="#cite_ref-pmid23375353_10-5">f</a> <a href="#cite_ref-pmid23375353_10-6">g</a> <a href="#cite_ref-pmid23375353_10-7">h</a> <a href="#cite_ref-pmid23375353_10-8">i</a> <a href="#cite_ref-pmid23375353_10-9">j</a> <a href="#cite_ref-pmid23375353_10-10">k</a> <a href="#cite_ref-pmid23375353_10-11">l</a> <a href="#cite_ref-pmid23375353_10-12">m</a> <a href="#cite_ref-pmid23375353_10-13">n</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFStanczykArcherBhavnani2013" class="citation journal cs1">Stanczyk FZ, Archer DF, Bhavnani BR (June 2013). "Ethinyl estradiol and 17β-estradiol in combined oral contraceptives: pharmacokinetics, pharmacodynamics and risk assessment". Contraception. 87 (6): 706–727. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.contraception.2012.12.011">10.1016/j.contraception.2012.12.011</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/23375353">23375353</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Contraception&rft.atitle=Ethinyl+estradiol+and+17%CE%B2-estradiol+in+combined+oral+contraceptives%3A+pharmacokinetics%2C+pharmacodynamics+and+risk+assessment&rft.volume=87&rft.issue=6&rft.pages=706-727&rft.date=2013-06&rft_id=info%3Adoi%2F10.1016%2Fj.contraception.2012.12.011&rft_id=info%3Apmid%2F23375353&rft.aulast=Stanczyk&rft.aufirst=FZ&rft.au=Archer%2C+DF&rft.au=Bhavnani%2C+BR&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Shellenberger1986-11">^ <a href="#cite_ref-Shellenberger1986_11-0">a</a> <a href="#cite_ref-Shellenberger1986_11-1">b</a> <a href="#cite_ref-Shellenberger1986_11-2">c</a> <a href="#cite_ref-Shellenberger1986_11-3">d</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFShellenberger1986" class="citation book cs1">Shellenberger TE (1986). "Pharmacology of estrogens". The Climacteric in Perspective. pp. 393–410. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-94-009-4145-8_36">10.1007/978-94-009-4145-8_36</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-94-010-8339-3" title="Special:BookSources/978-94-010-8339-3"><bdi>978-94-010-8339-3</bdi></a>. <q>Ethinyl estradiol is a synthetic and comparatively potent estrogen. As a result of the alkylation in 17-C position it is not a substrate for 17β dehydrogenase, an enzyme which transforms natural estradiol-17β to the less potent estrone in target organs.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Pharmacology+of+estrogens&rft.btitle=The+Climacteric+in+Perspective&rft.pages=393-410&rft.date=1986&rft_id=info%3Adoi%2F10.1007%2F978-94-009-4145-8_36&rft.isbn=978-94-010-8339-3&rft.aulast=Shellenberger&rft.aufirst=TE&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Drugs@FDA-12">^ <a href="#cite_ref-Drugs@FDA_12-0">a</a> <a href="#cite_ref-Drugs@FDA_12-1">b</a> <a href="#cite_ref-Drugs@FDA_12-2">c</a> <a href="#cite_ref-Drugs@FDA_12-3">d</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.accessdata.fda.gov/scripts/cder/daf/">"Drugs@FDA: FDA Approved Drug Products"</a>. U.S. <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> (FDA). Retrieved 22 December 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Drugs%40FDA%3A+FDA+Approved+Drug+Products&rft.pub=U.S.+Food+and+Drug+Administration+%28FDA%29&rft_id=http%3A%2F%2Fwww.accessdata.fda.gov%2Fscripts%2Fcder%2Fdaf%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Fis2006-13"><a href="#cite_ref-Fis2006_13-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFischerGanellin2006" class="citation book cs1">Fischer J, Ganellin CR (2006). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA482">Analogue-based Drug Discovery</a>. John Wiley & Sons. p. 482. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-527-60749-5" title="Special:BookSources/978-3-527-60749-5"><bdi>978-3-527-60749-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Analogue-based+Drug+Discovery&rft.pages=482&rft.pub=John+Wiley+%26+Sons&rft.date=2006&rft.isbn=978-3-527-60749-5&rft.aulast=Fischer&rft.aufirst=J&rft.au=Ganellin%2C+CR&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DFjKfqkaKkAAC%26pg%3DPA482&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Estinyl_1943-14">^ <a href="#cite_ref-Estinyl_1943_14-0">a</a> <a href="#cite_ref-Estinyl_1943_14-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFU.S._Food_and_Drug_Administration_(FDA)2007" class="citation web cs1">U.S. <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> (FDA) (2007). <a rel="nofollow" class="external text" href="http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.Set_Current_Drug&ApplNo=005292&DrugName=ESTINYL&ActiveIngred=ETHINYL%20ESTRADIOL&SponsorApplicant=SCHERING&ProductMktStatus=3&goto=Search.Label_ApprovalHistory">"Approval history: Estinyl (ethinyl estradiol) NDA 005292"</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Approval+history%3A+Estinyl+%28ethinyl+estradiol%29+NDA+005292&rft.date=2007&rft.au=U.S.+Food+and+Drug+Administration+%28FDA%29&rft_id=http%3A%2F%2Fwww.accessdata.fda.gov%2Fscripts%2Fcder%2Fdrugsatfda%2Findex.cfm%3Ffuseaction%3DSearch.Set_Current_Drug%26ApplNo%3D005292%26DrugName%3DESTINYL%26ActiveIngred%3DETHINYL%2520ESTRADIOL%26SponsorApplicant%3DSCHERING%26ProductMktStatus%3D3%26goto%3DSearch.Label_ApprovalHistory&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> search: Estinyl </li> <li id="cite_note-GruhnKazer2013-15">^ <a href="#cite_ref-GruhnKazer2013_15-0">a</a> <a href="#cite_ref-GruhnKazer2013_15-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGruhnKazer2013" class="citation book cs1">Gruhn JG, Kazer RR (11 November 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=lFn0BwAAQBAJ&pg=PA185">Hormonal Regulation of the Menstrual Cycle: The Evolution of Concepts</a>. Springer Science & Business Media. pp. 185–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4899-3496-3" title="Special:BookSources/978-1-4899-3496-3"><bdi>978-1-4899-3496-3</bdi></a>. <q>In 1964, ethinyl estradiol was introduced as an alternative to mestranol as the estrogenic component, [...]</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Hormonal+Regulation+of+the+Menstrual+Cycle%3A+The+Evolution+of+Concepts&rft.pages=185-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2013-11-11&rft.isbn=978-1-4899-3496-3&rft.aulast=Gruhn&rft.aufirst=JG&rft.au=Kazer%2C+RR&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DlFn0BwAAQBAJ%26pg%3DPA185&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid25841596-16"><a href="#cite_ref-pmid25841596_16-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFEvansSutton2015" class="citation journal cs1">Evans G, Sutton EL (May 2015). "Oral contraception". The Medical Clinics of North America. 99 (3): 479–503. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.mcna.2015.01.004">10.1016/j.mcna.2015.01.004</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/25841596">25841596</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Medical+Clinics+of+North+America&rft.atitle=Oral+contraception&rft.volume=99&rft.issue=3&rft.pages=479-503&rft.date=2015-05&rft_id=info%3Adoi%2F10.1016%2Fj.mcna.2015.01.004&rft_id=info%3Apmid%2F25841596&rft.aulast=Evans&rft.aufirst=G&rft.au=Sutton%2C+EL&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-ShoupeHaseltine2012-17"><a href="#cite_ref-ShoupeHaseltine2012_17-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFShoupeHaseltine2012" class="citation book cs1">Shoupe D, Haseltine FP (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=cpDhBwAAQBAJ&pg=PA112">Contraception</a>. Springer Science & Business Media. pp. 112–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4612-2730-4" title="Special:BookSources/978-1-4612-2730-4"><bdi>978-1-4612-2730-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Contraception&rft.pages=112-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-1-4612-2730-4&rft.aulast=Shoupe&rft.aufirst=D&rft.au=Haseltine%2C+FP&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DcpDhBwAAQBAJ%26pg%3DPA112&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Top_300_of_2022-18">^ <a href="#cite_ref-Top_300_of_2022_18-0">a</a> <a href="#cite_ref-Top_300_of_2022_18-1">b</a> <a href="#cite_ref-Top_300_of_2022_18-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://clincalc.com/DrugStats/Top300Drugs.aspx">"The Top 300 of 2022"</a>. ClinCalc. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20240830202410/https://clincalc.com/DrugStats/Top300Drugs.aspx">Archived</a> from the original on 30 August 2024. Retrieved 30 August 2024.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=ClinCalc&rft.atitle=The+Top+300+of+2022&rft_id=https%3A%2F%2Fclincalc.com%2FDrugStats%2FTop300Drugs.aspx&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-E+N-19">^ <a href="#cite_ref-E+N_19-0">a</a> <a href="#cite_ref-E+N_19-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://clincalc.com/DrugStats/Drugs/EthinylEstradiolNorethindrone">"Ethinyl Estradiol; Norethindrone Drug Usage Statistics, United States, 2013 - 2022"</a>. ClinCalc. Retrieved 30 August 2024.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=ClinCalc&rft.atitle=Ethinyl+Estradiol%3B+Norethindrone+Drug+Usage+Statistics%2C+United+States%2C+2013+-+2022&rft_id=https%3A%2F%2Fclincalc.com%2FDrugStats%2FDrugs%2FEthinylEstradiolNorethindrone&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid16860174-20">^ <a href="#cite_ref-pmid16860174_20-0">a</a> <a href="#cite_ref-pmid16860174_20-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRowanSimonSperoffEllman2006" class="citation journal cs1">Rowan JP, Simon JA, Speroff L, Ellman H (June 2006). "Effects of low-dose norethindrone acetate plus ethinyl estradiol (0.5 mg/2.5 microg) in women with postmenopausal symptoms: updated analysis of three randomized, controlled trials". Clinical Therapeutics. 28 (6): 921–932. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.clinthera.2006.06.013">10.1016/j.clinthera.2006.06.013</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16860174">16860174</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Clinical+Therapeutics&rft.atitle=Effects+of+low-dose+norethindrone+acetate+plus+ethinyl+estradiol+%280.5+mg%2F2.5+microg%29+in+women+with+postmenopausal+symptoms%3A+updated+analysis+of+three+randomized%2C+controlled+trials&rft.volume=28&rft.issue=6&rft.pages=921-932&rft.date=2006-06&rft_id=info%3Adoi%2F10.1016%2Fj.clinthera.2006.06.013&rft_id=info%3Apmid%2F16860174&rft.aulast=Rowan&rft.aufirst=JP&rft.au=Simon%2C+JA&rft.au=Speroff%2C+L&rft.au=Ellman%2C+H&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-21"><a href="#cite_ref-21">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHamodaPanayAryaSavvas2016" class="citation journal cs1">Hamoda H, Panay N, Arya R, Savvas M (December 2016). <a rel="nofollow" class="external text" href="https://doi.org/10.1177%2F2053369116680501">"The British Menopause Society & Women's Health Concern 2016 recommendations on hormone replacement therapy in menopausal women"</a>. Post Reproductive Health. 22 (4): 165–183. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1177%2F2053369116680501">10.1177/2053369116680501</a>. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<a rel="nofollow" class="external text" href="https://hdl.handle.net/1983%2Fd96e4479-2ccc-44c3-963c-d3918b1e325b">1983/d96e4479-2ccc-44c3-963c-d3918b1e325b</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Post+Reproductive+Health&rft.atitle=The+British+Menopause+Society+%26+Women%27s+Health+Concern+2016+recommendations+on+hormone+replacement+therapy+in+menopausal+women&rft.volume=22&rft.issue=4&rft.pages=165-183&rft.date=2016-12&rft_id=info%3Ahdl%2F1983%2Fd96e4479-2ccc-44c3-963c-d3918b1e325b&rft_id=info%3Adoi%2F10.1177%2F2053369116680501&rft.aulast=Hamoda&rft.aufirst=H&rft.au=Panay%2C+N&rft.au=Arya%2C+R&rft.au=Savvas%2C+M&rft_id=https%3A%2F%2Fdoi.org%2F10.1177%252F2053369116680501&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid28078219-22">^ <a href="#cite_ref-pmid28078219_22-0">a</a> <a href="#cite_ref-pmid28078219_22-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFUnger2016" class="citation journal cs1">Unger CA (December 2016). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5182227">"Hormone therapy for transgender patients"</a>. Translational Andrology and Urology. 5 (6): 877–884. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.21037%2Ftau.2016.09.04">10.21037/tau.2016.09.04</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5182227">5182227</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/28078219">28078219</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Translational+Andrology+and+Urology&rft.atitle=Hormone+therapy+for+transgender+patients&rft.volume=5&rft.issue=6&rft.pages=877-884&rft.date=2016-12&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5182227%23id-name%3DPMC&rft_id=info%3Apmid%2F28078219&rft_id=info%3Adoi%2F10.21037%2Ftau.2016.09.04&rft.aulast=Unger&rft.aufirst=CA&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5182227&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid27889048a-23">^ <a href="#cite_ref-pmid27889048a_23-0">a</a> <a href="#cite_ref-pmid27889048a_23-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCoelingh_BenninkVerhoevenDutmanThijssen2017" class="citation journal cs1">Coelingh Bennink HJ, Verhoeven C, Dutman AE, Thijssen J (January 2017). <a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.maturitas.2016.10.010">"The use of high-dose estrogens for the treatment of breast cancer"</a>. Maturitas. 95: 11–23. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.maturitas.2016.10.010">10.1016/j.maturitas.2016.10.010</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/27889048">27889048</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Maturitas&rft.atitle=The+use+of+high-dose+estrogens+for+the+treatment+of+breast+cancer&rft.volume=95&rft.pages=11-23&rft.date=2017-01&rft_id=info%3Adoi%2F10.1016%2Fj.maturitas.2016.10.010&rft_id=info%3Apmid%2F27889048&rft.aulast=Coelingh+Bennink&rft.aufirst=HJ&rft.au=Verhoeven%2C+C&rft.au=Dutman%2C+AE&rft.au=Thijssen%2C+J&rft_id=https%3A%2F%2Fdoi.org%2F10.1016%252Fj.maturitas.2016.10.010&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid20459370-24"><a href="#cite_ref-pmid20459370_24-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFThibautDe_La_BarraGordonCosyns2010" class="citation journal cs1">Thibaut F, De La Barra F, Gordon H, Cosyns P, Bradford JM (June 2010). "The World Federation of Societies of Biological Psychiatry (WFSBP) guidelines for the biological treatment of paraphilias". The World Journal of Biological Psychiatry. 11 (4): 604–655. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3109%2F15622971003671628">10.3109/15622971003671628</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/20459370">20459370</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:14949511">14949511</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+World+Journal+of+Biological+Psychiatry&rft.atitle=The+World+Federation+of+Societies+of+Biological+Psychiatry+%28WFSBP%29+guidelines+for+the+biological+treatment+of+paraphilias&rft.volume=11&rft.issue=4&rft.pages=604-655&rft.date=2010-06&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A14949511%23id-name%3DS2CID&rft_id=info%3Apmid%2F20459370&rft_id=info%3Adoi%2F10.3109%2F15622971003671628&rft.aulast=Thibaut&rft.aufirst=F&rft.au=De+La+Barra%2C+F&rft.au=Gordon%2C+H&rft.au=Cosyns%2C+P&rft.au=Bradford%2C+JM&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid4607733-25"><a href="#cite_ref-pmid4607733_25-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBancroftTennentLoucasCass1974" class="citation journal cs1">Bancroft J, Tennent G, Loucas K, Cass J (September 1974). "The control of deviant sexual behaviour by drugs. I. Behavioural changes following oestrogens and anti-androgens". The British Journal of Psychiatry. 125 (586): 310–315. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1192%2Fbjp.125.3.310">10.1192/bjp.125.3.310</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/4607733">4607733</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:10971754">10971754</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+British+Journal+of+Psychiatry&rft.atitle=The+control+of+deviant+sexual+behaviour+by+drugs.+I.+Behavioural+changes+following+oestrogens+and+anti-androgens&rft.volume=125&rft.issue=586&rft.pages=310-315&rft.date=1974-09&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A10971754%23id-name%3DS2CID&rft_id=info%3Apmid%2F4607733&rft_id=info%3Adoi%2F10.1192%2Fbjp.125.3.310&rft.aulast=Bancroft&rft.aufirst=J&rft.au=Tennent%2C+G&rft.au=Loucas%2C+K&rft.au=Cass%2C+J&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-ACS2015-26"><a href="#cite_ref-ACS2015_26-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.cancer.org/cancer/cancer-causes/medical-treatments/menopausal-hormone-replacement-therapy-and-cancer-risk.html">"Menopausal Hormone Therapy and Cancer Risk"</a>. American Cancer Society. 13 February 2015.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Menopausal+Hormone+Therapy+and+Cancer+Risk&rft.pub=American+Cancer+Society&rft.date=2015-02-13&rft_id=https%3A%2F%2Fwww.cancer.org%2Fcancer%2Fcancer-causes%2Fmedical-treatments%2Fmenopausal-hormone-replacement-therapy-and-cancer-risk.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-HumansOrganization2007-27">^ <a href="#cite_ref-HumansOrganization2007_27-0">a</a> <a href="#cite_ref-HumansOrganization2007_27-1">b</a> <a href="#cite_ref-HumansOrganization2007_27-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFIARC_Working_Group_on_the_Evaluation_of_Carcinogenic_Risks_to_HumansWorld_Health_OrganizationInternational_Agency_for_Research_on_Cancer2007" class="citation book cs1">IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, World Health Organization, International Agency for Research on Cancer (2007). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=aGDU5xibtNgC&pg=PA433">Combined Estrogen-progestogen Contraceptives and Combined Estrogen-progestogen Menopausal Therapy</a>. World Health Organization. pp. 157, 433–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-92-832-1291-1" title="Special:BookSources/978-92-832-1291-1"><bdi>978-92-832-1291-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Combined+Estrogen-progestogen+Contraceptives+and+Combined+Estrogen-progestogen+Menopausal+Therapy&rft.pages=157%2C+433-&rft.pub=World+Health+Organization&rft.date=2007&rft.isbn=978-92-832-1291-1&rft.au=IARC+Working+Group+on+the+Evaluation+of+Carcinogenic+Risks+to+Humans&rft.au=World+Health+Organization&rft.au=International+Agency+for+Research+on+Cancer&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DaGDU5xibtNgC%26pg%3DPA433&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Becker2001-28">^ <a href="#cite_ref-Becker2001_28-0">a</a> <a href="#cite_ref-Becker2001_28-1">b</a> <a href="#cite_ref-Becker2001_28-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBecker2001" class="citation book cs1">Becker KL (2001). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=FVfzRvaucq8C&pg=PA1027">Principles and Practice of Endocrinology and Metabolism</a>. Lippincott Williams & Wilkins. p. 1027. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7817-1750-2" title="Special:BookSources/978-0-7817-1750-2"><bdi>978-0-7817-1750-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Principles+and+Practice+of+Endocrinology+and+Metabolism&rft.pages=1027&rft.pub=Lippincott+Williams+%26+Wilkins&rft.date=2001&rft.isbn=978-0-7817-1750-2&rft.aulast=Becker&rft.aufirst=KL&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DFVfzRvaucq8C%26pg%3DPA1027&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-DIANE1995-29"><a href="#cite_ref-DIANE1995_29-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDIANE_Publishing_Company1995" class="citation book cs1">DIANE Publishing Company (1995). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=uo0QFvym_90C&pg=RA4-PA4">Approved Drug Products with Therapeutic Evaluations</a>. DIANE Publishing. p. 3-122. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7881-0405-3" title="Special:BookSources/978-0-7881-0405-3"><bdi>978-0-7881-0405-3</bdi></a>. <q>ETHINYL ESTRADIOL: TABLET; ORAL: ESTINYL: SCHERING: 0.02MG; 0.05MG; 0.5MG</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Approved+Drug+Products+with+Therapeutic+Evaluations&rft.pages=3-122&rft.pub=DIANE+Publishing&rft.date=1995&rft.isbn=978-0-7881-0405-3&rft.au=DIANE+Publishing+Company&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Duo0QFvym_90C%26pg%3DRA4-PA4&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-U.S._Department_of_Health_and_Human_Services,_Public_Health_Service,_Food_and_Drug_Administration,_Bureau_of_Drugs1980-30"><a href="#cite_ref-U.S._Department_of_Health_and_Human_Services,_Public_Health_Service,_Food_and_Drug_Administration,_Bureau_of_Drugs1980_30-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1"><a rel="nofollow" class="external text" href="https://books.google.com/books?id=XOP58uLdW_MC">Approved Prescription Drug Products with Therapeutic Equivalence Evaluations</a>. U.S. Department of Health and Human Services, Public Health Service, Food and Drug Administration, Bureau of Drugs. 1980. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/7074861">7074861</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Approved+Prescription+Drug+Products+with+Therapeutic+Equivalence+Evaluations&rft.pub=U.S.+Department+of+Health+and+Human+Services%2C+Public+Health+Service%2C+Food+and+Drug+Administration%2C+Bureau+of+Drugs&rft.date=1980&rft_id=info%3Aoclcnum%2F7074861&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DXOP58uLdW_MC&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Muller1998-31"><a href="#cite_ref-Muller1998_31-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMuller1998" class="citation book cs1">Muller (19 June 1998). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=2HBPHmclMWIC&pg=PA457">European Drug Index: European Drug Registrations, Fourth Edition</a> (4 ed.). CRC Press. pp. 457–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-7692-2114-5" title="Special:BookSources/978-3-7692-2114-5"><bdi>978-3-7692-2114-5</bdi></a>. <q>Ethinyl oestradiol 0,05mg cpr 0,05 mg ethinylestradiol (G03CA01) (FR) Ethinylestradiol tablets 50 mcg Ethinylestradiol (G03CA01) (RUS) Ethinylestradiol 25μg (Jenapharm) Dragees: Ethinylestradiol 25μg (G03CA01) (DE) Ethinylestradiol pch 0,002mg cpr 0,002 mg ethinylestradiol (FR) Ethinylestradiolum tablet 0,05mg ethinylestradiol 0,05 mg (G03CA01) (NL) [...] Etifollin tab 0,5mg (Nycomed pharma a/s) ethinylestradiol (L02AA03) (NO) Etifollin tab 50mcg (Nycomed pharma a/s) ethinylestradiol (G03CA01) (NO)</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=European+Drug+Index%3A+European+Drug+Registrations%2C+Fourth+Edition&rft.pages=457-&rft.edition=4&rft.pub=CRC+Press&rft.date=1998-06-19&rft.isbn=978-3-7692-2114-5&rft.au=Muller&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D2HBPHmclMWIC%26pg%3DPA457&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-MonfardiniBrunnerCrowther2012-32"><a href="#cite_ref-MonfardiniBrunnerCrowther2012_32-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFS._MonfardiniK._BrunnerD._CrowtherS._Eckhardt2012" class="citation book cs1">S. Monfardini, K. Brunner, D. Crowther, S. Eckhardt, D. Olive, S. Tanneberger, A. Veronesi, J.M.A. Whitehouse, R. Wittes, eds. (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=CeXnCAAAQBAJ&pg=PA78">Manual of Adult and Paediatric Medical Oncology</a>. Springer Science & Business Media. pp. 78–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-82489-0" title="Special:BookSources/978-3-642-82489-0"><bdi>978-3-642-82489-0</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/1058058829">1058058829</a>. <q>Ethinyloestradiol (Lynoral, 0.05-mg, 0.1-mg, 1-mg tablets)</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Manual+of+Adult+and+Paediatric+Medical+Oncology&rft.pages=78-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft_id=info%3Aoclcnum%2F1058058829&rft.isbn=978-3-642-82489-0&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DCeXnCAAAQBAJ%26pg%3DPA78&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-LipHall2007-33">^ <a href="#cite_ref-LipHall2007_33-0">a</a> <a href="#cite_ref-LipHall2007_33-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLipHall2007" class="citation book cs1">Lip GY, Hall JE (28 June 2007). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=XQajBQAAQBAJ&pg=PA865">Comprehensive Hypertension E-Book</a>. Elsevier Health Sciences. pp. 865–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-323-07067-6" title="Special:BookSources/978-0-323-07067-6"><bdi>978-0-323-07067-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Comprehensive+Hypertension+E-Book&rft.pages=865-&rft.pub=Elsevier+Health+Sciences&rft.date=2007-06-28&rft.isbn=978-0-323-07067-6&rft.aulast=Lip&rft.aufirst=GY&rft.au=Hall%2C+JE&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DXQajBQAAQBAJ%26pg%3DPA865&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-AlldredgeCorelli2012-34">^ <a href="#cite_ref-AlldredgeCorelli2012_34-0">a</a> <a href="#cite_ref-AlldredgeCorelli2012_34-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAlldredgeCorelliErnst2012" class="citation book cs1">Alldredge BK, Corelli RL, Ernst ME (1 February 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=qcVpuHngXK0C&pg=PA1072">Koda-Kimble and Young's Applied Therapeutics: The Clinical Use of Drugs</a>. Lippincott Williams & Wilkins. pp. 1072–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-60913-713-7" title="Special:BookSources/978-1-60913-713-7"><bdi>978-1-60913-713-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Koda-Kimble+and+Young%27s+Applied+Therapeutics%3A+The+Clinical+Use+of+Drugs&rft.pages=1072-&rft.pub=Lippincott+Williams+%26+Wilkins&rft.date=2012-02-01&rft.isbn=978-1-60913-713-7&rft.aulast=Alldredge&rft.aufirst=BK&rft.au=Corelli%2C+RL&rft.au=Ernst%2C+ME&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DqcVpuHngXK0C%26pg%3DPA1072&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-35"><a href="#cite_ref-35">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation magazine cs1"><a rel="nofollow" class="external text" href="https://www.cdc.gov/mmwr/volumes/65/rr/pdfs/rr6504.pdf">"U.S. Selected Practice Recommendations for Contraceptive Use, 2016"</a> (PDF). Recommendations and Reports. Vol. 65, no. 4. Centers for Disease Control and Prevention. 29 July 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Recommendations+and+Reports&rft.atitle=U.S.+Selected+Practice+Recommendations+for+Contraceptive+Use%2C+2016&rft.volume=65&rft.issue=4&rft.date=2016-07-29&rft_id=https%3A%2F%2Fwww.cdc.gov%2Fmmwr%2Fvolumes%2F65%2Frr%2Fpdfs%2Frr6504.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-CDC2016-36"><a href="#cite_ref-CDC2016_36-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation magazine cs1"><a rel="nofollow" class="external text" href="https://www.cdc.gov/mmwr/volumes/65/rr/pdfs/rr6504.pdf">"U.S. Selected Practice Recommendations for Contraceptive Use, 2016"</a> (PDF). Recommendations and Reports. Vol. 65, no. 4. Centers for Disease Control and Prevention. 29 July 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Recommendations+and+Reports&rft.atitle=U.S.+Selected+Practice+Recommendations+for+Contraceptive+Use%2C+2016&rft.volume=65&rft.issue=4&rft.date=2016-07-29&rft_id=https%3A%2F%2Fwww.cdc.gov%2Fmmwr%2Fvolumes%2F65%2Frr%2Fpdfs%2Frr6504.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-cdc.gov-37">^ <a href="#cite_ref-cdc.gov_37-0">a</a> <a href="#cite_ref-cdc.gov_37-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation magazine cs1"><a rel="nofollow" class="external text" href="https://www.cdc.gov/mmwr/volumes/65/rr/pdfs/rr6503.pdf">"U.S. Medical Eligibility Criteria for Contraceptive Use, 2016"</a> (PDF). Recommendations and Reports. Vol. 65, no. 3. Centers for Disease Control and Prevention. 29 July 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Recommendations+and+Reports&rft.atitle=U.S.+Medical+Eligibility+Criteria+for+Contraceptive+Use%2C+2016&rft.volume=65&rft.issue=3&rft.date=2016-07-29&rft_id=https%3A%2F%2Fwww.cdc.gov%2Fmmwr%2Fvolumes%2F65%2Frr%2Fpdfs%2Frr6503.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Aronson2009-38">^ <a href="#cite_ref-Aronson2009_38-0">a</a> <a href="#cite_ref-Aronson2009_38-1">b</a> <a href="#cite_ref-Aronson2009_38-2">c</a> <a href="#cite_ref-Aronson2009_38-3">d</a> <a href="#cite_ref-Aronson2009_38-4">e</a> <a href="#cite_ref-Aronson2009_38-5">f</a> <a href="#cite_ref-Aronson2009_38-6">g</a> <a href="#cite_ref-Aronson2009_38-7">h</a> <a href="#cite_ref-Aronson2009_38-8">i</a> <a href="#cite_ref-Aronson2009_38-9">j</a> <a href="#cite_ref-Aronson2009_38-10">k</a> <a href="#cite_ref-Aronson2009_38-11">l</a> <a href="#cite_ref-Aronson2009_38-12">m</a> <a href="#cite_ref-Aronson2009_38-13">n</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAronson2009" class="citation book cs1">Aronson JK (21 February 2009). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=BWMeSwVwfTkC&pg=PA177">Meyler's Side Effects of Endocrine and Metabolic Drugs</a>. Elsevier. pp. 177, 219, 223, 224, 230, 232, 239, 242. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-08-093292-7" title="Special:BookSources/978-0-08-093292-7"><bdi>978-0-08-093292-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Meyler%27s+Side+Effects+of+Endocrine+and+Metabolic+Drugs&rft.pages=177%2C+219%2C+223%2C+224%2C+230%2C+232%2C+239%2C+242&rft.pub=Elsevier&rft.date=2009-02-21&rft.isbn=978-0-08-093292-7&rft.aulast=Aronson&rft.aufirst=JK&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DBWMeSwVwfTkC%26pg%3DPA177&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid1983896-39">^ <a href="#cite_ref-pmid1983896_39-0">a</a> <a href="#cite_ref-pmid1983896_39-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGerstmanPiperTomitaFerguson1991" class="citation journal cs1">Gerstman BB, Piper JM, Tomita DK, Ferguson WJ, Stadel BV, Lundin FE (January 1991). "Oral contraceptive estrogen dose and the risk of deep venous thromboembolic disease". American Journal of Epidemiology. 133 (1): 32–37. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Foxfordjournals.aje.a115799">10.1093/oxfordjournals.aje.a115799</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/1983896">1983896</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=American+Journal+of+Epidemiology&rft.atitle=Oral+contraceptive+estrogen+dose+and+the+risk+of+deep+venous+thromboembolic+disease&rft.volume=133&rft.issue=1&rft.pages=32-37&rft.date=1991-01&rft_id=info%3Adoi%2F10.1093%2Foxfordjournals.aje.a115799&rft_id=info%3Apmid%2F1983896&rft.aulast=Gerstman&rft.aufirst=BB&rft.au=Piper%2C+JM&rft.au=Tomita%2C+DK&rft.au=Ferguson%2C+WJ&rft.au=Stadel%2C+BV&rft.au=Lundin%2C+FE&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-RunnebaumRabe2013-40">^ <a href="#cite_ref-RunnebaumRabe2013_40-0">a</a> <a href="#cite_ref-RunnebaumRabe2013_40-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRunnebaumRabe2013" class="citation book cs1">Runnebaum B, Rabe T, eds. (17 April 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=mBF9BwAAQBAJ&pg=PA411">"Kontrazeption"</a>. Gynäkologische Endokrinologie und Fortpflanzungsmedizin: Band 1: Gynäkologische Endokrinologie. Springer-Verlag. pp. 411–512. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-662-07635-4" title="Special:BookSources/978-3-662-07635-4"><bdi>978-3-662-07635-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Kontrazeption&rft.btitle=Gyn%C3%A4kologische+Endokrinologie+und+Fortpflanzungsmedizin%3A+Band+1%3A+Gyn%C3%A4kologische+Endokrinologie&rft.pages=411-512&rft.pub=Springer-Verlag&rft.date=2013-04-17&rft.isbn=978-3-662-07635-4&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DmBF9BwAAQBAJ%26pg%3DPA411&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid1983923-41">^ <a href="#cite_ref-pmid1983923_41-0">a</a> <a href="#cite_ref-pmid1983923_41-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGerstmanGrossKennedyBennett1991" class="citation journal cs1">Gerstman BB, Gross TP, Kennedy DL, Bennett RC, Tomita DK, Stadel BV (January 1991). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1404924">"Trends in the content and use of oral contraceptives in the United States, 1964-88"</a>. American Journal of Public Health. 81 (1): 90–96. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.2105%2Fajph.81.1.90">10.2105/ajph.81.1.90</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1404924">1404924</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/1983923">1983923</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=American+Journal+of+Public+Health&rft.atitle=Trends+in+the+content+and+use+of+oral+contraceptives+in+the+United+States%2C+1964-88&rft.volume=81&rft.issue=1&rft.pages=90-96&rft.date=1991-01&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1404924%23id-name%3DPMC&rft_id=info%3Apmid%2F1983923&rft_id=info%3Adoi%2F10.2105%2Fajph.81.1.90&rft.aulast=Gerstman&rft.aufirst=BB&rft.au=Gross%2C+TP&rft.au=Kennedy%2C+DL&rft.au=Bennett%2C+RC&rft.au=Tomita%2C+DK&rft.au=Stadel%2C+BV&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1404924&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-42"><a href="#cite_ref-42">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGalloNandaGrimesLopez2013" class="citation journal cs1">Gallo MF, Nanda K, Grimes DA, Lopez LM, Schulz KF (August 2013). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7173696">"20 μg versus >20 μg estrogen combined oral contraceptives for contraception"</a>. The Cochrane Database of Systematic Reviews. 2013 (8): CD003989. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14651858.CD003989.pub5">10.1002/14651858.CD003989.pub5</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7173696">7173696</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/23904209">23904209</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Cochrane+Database+of+Systematic+Reviews&rft.atitle=20+%CE%BCg+versus+%3E20+%CE%BCg+estrogen+combined+oral+contraceptives+for+contraception&rft.volume=2013&rft.issue=8&rft.pages=CD003989&rft.date=2013-08&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7173696%23id-name%3DPMC&rft_id=info%3Apmid%2F23904209&rft_id=info%3Adoi%2F10.1002%2F14651858.CD003989.pub5&rft.aulast=Gallo&rft.aufirst=MF&rft.au=Nanda%2C+K&rft.au=Grimes%2C+DA&rft.au=Lopez%2C+LM&rft.au=Schulz%2C+KF&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7173696&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Pincus2013-43"><a href="#cite_ref-Pincus2013_43-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPincus2013" class="citation book cs1">Pincus G (22 October 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=NiXgBAAAQBAJ&pg=PA411">Hormones and Atherosclerosis: Proceedings of the Conference Held in Brighton, Utah, March 11-14, 1958</a>. Elsevier Science. pp. 411–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4832-7064-7" title="Special:BookSources/978-1-4832-7064-7"><bdi>978-1-4832-7064-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Hormones+and+Atherosclerosis%3A+Proceedings+of+the+Conference+Held+in+Brighton%2C+Utah%2C+March+11-14%2C+1958&rft.pages=411-&rft.pub=Elsevier+Science&rft.date=2013-10-22&rft.isbn=978-1-4832-7064-7&rft.aulast=Pincus&rft.aufirst=G&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DNiXgBAAAQBAJ%26pg%3DPA411&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-OettelSchillinger2012b-44"><a href="#cite_ref-OettelSchillinger2012b_44-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFOettelSchillinger2012" class="citation book cs1">Oettel M, Schillinger E (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=wBvyCAAAQBAJ&pg=PA390">Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen</a>. Springer Science & Business Media. p. 390. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-60107-1" title="Special:BookSources/978-3-642-60107-1"><bdi>978-3-642-60107-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Estrogens+and+Antiestrogens+II%3A+Pharmacology+and+Clinical+Application+of+Estrogens+and+Antiestrogen&rft.pages=390&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-3-642-60107-1&rft.aulast=Oettel&rft.aufirst=M&rft.au=Schillinger%2C+E&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DwBvyCAAAQBAJ%26pg%3DPA390&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Legato2009-45">^ <a href="#cite_ref-Legato2009_45-0">a</a> <a href="#cite_ref-Legato2009_45-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLegato2009" class="citation book cs1">Legato MJ (29 October 2009). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=whb9hsUgZtwC&pg=PA225">Principles of Gender-Specific Medicine</a>. Academic Press. pp. 225–234. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-08-092150-1" title="Special:BookSources/978-0-08-092150-1"><bdi>978-0-08-092150-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Principles+of+Gender-Specific+Medicine&rft.pages=225-234&rft.pub=Academic+Press&rft.date=2009-10-29&rft.isbn=978-0-08-092150-1&rft.aulast=Legato&rft.aufirst=MJ&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dwhb9hsUgZtwC%26pg%3DPA225&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Stein2016-46">^ <a href="#cite_ref-Stein2016_46-0">a</a> <a href="#cite_ref-Stein2016_46-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFStein2016" class="citation book cs1">Stein PD (5 April 2016). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=V2zkCwAAQBAJ&pg=PA187">Pulmonary Embolism</a>. Wiley. pp. 187–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-119-03909-9" title="Special:BookSources/978-1-119-03909-9"><bdi>978-1-119-03909-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Pulmonary+Embolism&rft.pages=187-&rft.pub=Wiley&rft.date=2016-04-05&rft.isbn=978-1-119-03909-9&rft.aulast=Stein&rft.aufirst=PD&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DV2zkCwAAQBAJ%26pg%3DPA187&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid27793376-47">^ <a href="#cite_ref-pmid27793376_47-0">a</a> <a href="#cite_ref-pmid27793376_47-1">b</a> <a href="#cite_ref-pmid27793376_47-2">c</a> <a href="#cite_ref-pmid27793376_47-3">d</a> <a href="#cite_ref-pmid27793376_47-4">e</a> <a href="#cite_ref-pmid27793376_47-5">f</a> <a href="#cite_ref-pmid27793376_47-6">g</a> <a href="#cite_ref-pmid27793376_47-7">h</a> <a href="#cite_ref-pmid27793376_47-8">i</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPfeiferButtsDumesicFossum2017" class="citation journal cs1">Pfeifer S, Butts S, Dumesic D, Fossum G, Gracia C, La Barbera A, et al. (Practice Committee of the American Society for Reproductive Medicine) (January 2017). <a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.fertnstert.2016.09.027">"Combined hormonal contraception and the risk of venous thromboembolism: a guideline"</a>. Fertility and Sterility. 107 (1): 43–51. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.fertnstert.2016.09.027">10.1016/j.fertnstert.2016.09.027</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/27793376">27793376</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Fertility+and+Sterility&rft.atitle=Combined+hormonal+contraception+and+the+risk+of+venous+thromboembolism%3A+a+guideline&rft.volume=107&rft.issue=1&rft.pages=43-51&rft.date=2017-01&rft_id=info%3Adoi%2F10.1016%2Fj.fertnstert.2016.09.027&rft_id=info%3Apmid%2F27793376&rft.aulast=Pfeifer&rft.aufirst=S&rft.au=Butts%2C+S&rft.au=Dumesic%2C+D&rft.au=Fossum%2C+G&rft.au=Gracia%2C+C&rft.au=La+Barbera%2C+A&rft.au=Mersereau%2C+J&rft.au=Odem%2C+R&rft.au=Penzias%2C+A&rft.au=Pisarska%2C+M&rft.au=Rebar%2C+R&rft.au=Reindollar%2C+R&rft.au=Rosen%2C+M&rft.au=Sandlow%2C+J&rft.au=Sokol%2C+R&rft.au=Vernon%2C+M&rft.au=Widra%2C+E&rft_id=https%3A%2F%2Fdoi.org%2F10.1016%252Fj.fertnstert.2016.09.027&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid23384743-48">^ <a href="#cite_ref-pmid23384743_48-0">a</a> <a href="#cite_ref-pmid23384743_48-1">b</a> <a href="#cite_ref-pmid23384743_48-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPlu-BureauMaitrot-ManteletHugon-RodinCanonico2013" class="citation journal cs1">Plu-Bureau G, Maitrot-Mantelet L, Hugon-Rodin J, Canonico M (February 2013). "Hormonal contraceptives and venous thromboembolism: an epidemiological update". Best Practice & Research. Clinical Endocrinology & Metabolism. 27 (1): 25–34. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.beem.2012.11.002">10.1016/j.beem.2012.11.002</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/23384743">23384743</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Best+Practice+%26+Research.+Clinical+Endocrinology+%26+Metabolism&rft.atitle=Hormonal+contraceptives+and+venous+thromboembolism%3A+an+epidemiological+update&rft.volume=27&rft.issue=1&rft.pages=25-34&rft.date=2013-02&rft_id=info%3Adoi%2F10.1016%2Fj.beem.2012.11.002&rft_id=info%3Apmid%2F23384743&rft.aulast=Plu-Bureau&rft.aufirst=G&rft.au=Maitrot-Mantelet%2C+L&rft.au=Hugon-Rodin%2C+J&rft.au=Canonico%2C+M&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-KeenanKerr2019-49"><a href="#cite_ref-KeenanKerr2019_49-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKeenanKerrDuaneVan_Gundy2018" class="citation journal cs1">Keenan L, Kerr T, Duane M, Van Gundy K (November 2018). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6322116">"Systematic Review of Hormonal Contraception and Risk of Venous Thrombosis"</a>. The Linacre Quarterly. 85 (4): 470–477. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1177%2F0024363918816683">10.1177/0024363918816683</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6322116">6322116</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/32431379">32431379</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Linacre+Quarterly&rft.atitle=Systematic+Review+of+Hormonal+Contraception+and+Risk+of+Venous+Thrombosis&rft.volume=85&rft.issue=4&rft.pages=470-477&rft.date=2018-11&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6322116%23id-name%3DPMC&rft_id=info%3Apmid%2F32431379&rft_id=info%3Adoi%2F10.1177%2F0024363918816683&rft.aulast=Keenan&rft.aufirst=L&rft.au=Kerr%2C+T&rft.au=Duane%2C+M&rft.au=Van+Gundy%2C+K&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6322116&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-FalconeHurd2007-50">^ <a href="#cite_ref-FalconeHurd2007_50-0">a</a> <a href="#cite_ref-FalconeHurd2007_50-1">b</a> <a href="#cite_ref-FalconeHurd2007_50-2">c</a> <a href="#cite_ref-FalconeHurd2007_50-3">d</a> <a href="#cite_ref-FalconeHurd2007_50-4">e</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFalconeHurd2007" class="citation book cs1">Falcone T, Hurd WW (2007). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=fOPtaEIKvcIC&pg=PA388">Clinical Reproductive Medicine and Surgery</a>. Elsevier Health Sciences. pp. 388–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-323-03309-1" title="Special:BookSources/978-0-323-03309-1"><bdi>978-0-323-03309-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Clinical+Reproductive+Medicine+and+Surgery&rft.pages=388-&rft.pub=Elsevier+Health+Sciences&rft.date=2007&rft.isbn=978-0-323-03309-1&rft.aulast=Falcone&rft.aufirst=T&rft.au=Hurd%2C+WW&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DfOPtaEIKvcIC%26pg%3DPA388&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid28376481-51"><a href="#cite_ref-pmid28376481_51-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChristin-Maitre2017" class="citation journal cs1">Christin-Maitre S (2017). <a rel="nofollow" class="external text" href="https://doi.org/10.1159%2F000457125">"Use of Hormone Replacement in Females with Endocrine Disorders"</a>. Hormone Research in Paediatrics. 87 (4): 215–223. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1159%2F000457125">10.1159/000457125</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/28376481">28376481</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Hormone+Research+in+Paediatrics&rft.atitle=Use+of+Hormone+Replacement+in+Females+with+Endocrine+Disorders&rft.volume=87&rft.issue=4&rft.pages=215-223&rft.date=2017&rft_id=info%3Adoi%2F10.1159%2F000457125&rft_id=info%3Apmid%2F28376481&rft.aulast=Christin-Maitre&rft.aufirst=S&rft_id=https%3A%2F%2Fdoi.org%2F10.1159%252F000457125&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Becker2001b-52"><a href="#cite_ref-Becker2001b_52-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBecker2001" class="citation book cs1">Becker KL (2001). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=FVfzRvaucq8C&pg=PA1024">Principles and Practice of Endocrinology and Metabolism</a>. Lippincott Williams & Wilkins. pp. 1024, 1027, 1035, 2153. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7817-1750-2" title="Special:BookSources/978-0-7817-1750-2"><bdi>978-0-7817-1750-2</bdi></a>. <q>Low-dose COCs contain <50 μg of estrogen and are the primary choice for oral contraception. COCs containing ≥50 μg of estrogen should no longer be routinely used for contraception. [...] The estrogen component of COCs can cause breast fullness and tenderness.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Principles+and+Practice+of+Endocrinology+and+Metabolism&rft.pages=1024%2C+1027%2C+1035%2C+2153&rft.pub=Lippincott+Williams+%26+Wilkins&rft.date=2001&rft.isbn=978-0-7817-1750-2&rft.aulast=Becker&rft.aufirst=KL&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DFVfzRvaucq8C%26pg%3DPA1024&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-BreastCancer1991-53"><a href="#cite_ref-BreastCancer1991_53-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCommittee_on_the_Relationship_Between_Oral_Contraceptives_and_BreastCancer1991" class="citation book cs1">Committee on the Relationship Between Oral Contraceptives and BreastCancer (1 January 1991). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=upYrAAAAYAAJ&pg=PA143">Oral Contraceptives and Breast Cancer</a>. National Academies. pp. 143–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-309-04493-6" title="Special:BookSources/978-0-309-04493-6"><bdi>978-0-309-04493-6</bdi></a>. NAP:13774. <q>Following a recommendation by its Fertility and Maternal Health Drugs Advisory Committee, the Food and Drug Administration (FDA) recently ordered the removal from the market of all oral contraceptives with [ethinylestradiol] contents greater than 50 μg.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Oral+Contraceptives+and+Breast+Cancer&rft.pages=143-&rft.pub=National+Academies&rft.date=1991-01-01&rft.isbn=978-0-309-04493-6&rft.au=Committee+on+the+Relationship+Between+Oral+Contraceptives+and+BreastCancer&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DupYrAAAAYAAJ%26pg%3DPA143&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-DIANE-54"><a href="#cite_ref-DIANE_54-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1"><a rel="nofollow" class="external text" href="https://books.google.com/books?id=wAnRHsPQcBQC&pg=PA27">Multigenerational Reproductive Toxicology Study of Ethinyl Estradiol (CAS No. 57636) in SpragueDawley Rats (Feed Studies)</a>. DIANE Publishing. pp. 27–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4379-4231-6" title="Special:BookSources/978-1-4379-4231-6"><bdi>978-1-4379-4231-6</bdi></a>. <q>Oral contraceptive formulations containing greater than 50 ug ethinyl estradiol were removed from the United States market in 1989, and currently marketed formulations generally contain between 20 and 35 μg ethinyl estradiol.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Multigenerational+Reproductive+Toxicology+Study+of+Ethinyl+Estradiol+%28CAS+No.+57636%29+in+SpragueDawley+Rats+%28Feed+Studies%29&rft.pages=27-&rft.pub=DIANE+Publishing&rft.isbn=978-1-4379-4231-6&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DwAnRHsPQcBQC%26pg%3DPA27&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid27678035-55"><a href="#cite_ref-pmid27678035_55-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSitruk-Ware2016" class="citation journal cs1">Sitruk-Ware R (November 2016). <a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.fertnstert.2016.08.039">"Hormonal contraception and thrombosis"</a>. Fertility and Sterility. 106 (6): 1289–1294. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.fertnstert.2016.08.039">10.1016/j.fertnstert.2016.08.039</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/27678035">27678035</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Fertility+and+Sterility&rft.atitle=Hormonal+contraception+and+thrombosis&rft.volume=106&rft.issue=6&rft.pages=1289-1294&rft.date=2016-11&rft_id=info%3Adoi%2F10.1016%2Fj.fertnstert.2016.08.039&rft_id=info%3Apmid%2F27678035&rft.aulast=Sitruk-Ware&rft.aufirst=R&rft_id=https%3A%2F%2Fdoi.org%2F10.1016%252Fj.fertnstert.2016.08.039&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid23904209-56"><a href="#cite_ref-pmid23904209_56-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGalloNandaGrimesLopez2013" class="citation journal cs1">Gallo MF, Nanda K, Grimes DA, Lopez LM, Schulz KF (August 2013). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7173696">"20 μg versus >20 μg estrogen combined oral contraceptives for contraception"</a>. The Cochrane Database of Systematic Reviews. 2013 (8): CD003989. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14651858.CD003989.pub5">10.1002/14651858.CD003989.pub5</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7173696">7173696</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/23904209">23904209</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Cochrane+Database+of+Systematic+Reviews&rft.atitle=20+%CE%BCg+versus+%3E20+%CE%BCg+estrogen+combined+oral+contraceptives+for+contraception&rft.volume=2013&rft.issue=8&rft.pages=CD003989&rft.date=2013-08&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7173696%23id-name%3DPMC&rft_id=info%3Apmid%2F23904209&rft_id=info%3Adoi%2F10.1002%2F14651858.CD003989.pub5&rft.aulast=Gallo&rft.aufirst=MF&rft.au=Nanda%2C+K&rft.au=Grimes%2C+DA&rft.au=Lopez%2C+LM&rft.au=Schulz%2C+KF&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7173696&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid12047300-57">^ <a href="#cite_ref-pmid12047300_57-0">a</a> <a href="#cite_ref-pmid12047300_57-1">b</a> <a href="#cite_ref-pmid12047300_57-2">c</a> <a href="#cite_ref-pmid12047300_57-3">d</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFOdlindMilsomPerssonVictor2002" class="citation journal cs1">Odlind V, Milsom I, Persson I, Victor A (June 2002). "Can changes in sex hormone binding globulin predict the risk of venous thromboembolism with combined oral contraceptive pills?". Acta Obstetricia et Gynecologica Scandinavica. 81 (6): 482–490. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/12047300">12047300</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Obstetricia+et+Gynecologica+Scandinavica&rft.atitle=Can+changes+in+sex+hormone+binding+globulin+predict+the+risk+of+venous+thromboembolism+with+combined+oral+contraceptive+pills%3F&rft.volume=81&rft.issue=6&rft.pages=482-490&rft.date=2002-06&rft_id=info%3Apmid%2F12047300&rft.aulast=Odlind&rft.aufirst=V&rft.au=Milsom%2C+I&rft.au=Persson%2C+I&rft.au=Victor%2C+A&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid22469296-58"><a href="#cite_ref-pmid22469296_58-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRapsHelmerhorstFleischerThomassen2012" class="citation journal cs1">Raps M, Helmerhorst F, Fleischer K, Thomassen S, Rosendaal F, Rosing J, et al. (June 2012). <a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1538-7836.2012.04720.x">"Sex hormone-binding globulin as a marker for the thrombotic risk of hormonal contraceptives"</a>. Journal of Thrombosis and Haemostasis. 10 (6): 992–997. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1538-7836.2012.04720.x">10.1111/j.1538-7836.2012.04720.x</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/22469296">22469296</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:20803995">20803995</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Thrombosis+and+Haemostasis&rft.atitle=Sex+hormone-binding+globulin+as+a+marker+for+the+thrombotic+risk+of+hormonal+contraceptives&rft.volume=10&rft.issue=6&rft.pages=992-997&rft.date=2012-06&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A20803995%23id-name%3DS2CID&rft_id=info%3Apmid%2F22469296&rft_id=info%3Adoi%2F10.1111%2Fj.1538-7836.2012.04720.x&rft.aulast=Raps&rft.aufirst=M&rft.au=Helmerhorst%2C+F&rft.au=Fleischer%2C+K&rft.au=Thomassen%2C+S&rft.au=Rosendaal%2C+F&rft.au=Rosing%2C+J&rft.au=Ballieux%2C+B&rft.au=VAN+Vliet%2C+H&rft_id=https%3A%2F%2Fdoi.org%2F10.1111%252Fj.1538-7836.2012.04720.x&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid18692609-59"><a href="#cite_ref-pmid18692609_59-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFStanczykGrimes2008" class="citation journal cs1">Stanczyk FZ, Grimes DA (September 2008). "Sex hormone-binding globulin: not a surrogate marker for venous thromboembolism in women using oral contraceptives". Contraception. 78 (3): 201–203. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.contraception.2008.04.004">10.1016/j.contraception.2008.04.004</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/18692609">18692609</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Contraception&rft.atitle=Sex+hormone-binding+globulin%3A+not+a+surrogate+marker+for+venous+thromboembolism+in+women+using+oral+contraceptives&rft.volume=78&rft.issue=3&rft.pages=201-203&rft.date=2008-09&rft_id=info%3Adoi%2F10.1016%2Fj.contraception.2008.04.004&rft_id=info%3Apmid%2F18692609&rft.aulast=Stanczyk&rft.aufirst=FZ&rft.au=Grimes%2C+DA&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-WintersHuhtaniemi2017-60">^ <a href="#cite_ref-WintersHuhtaniemi2017_60-0">a</a> <a href="#cite_ref-WintersHuhtaniemi2017_60-1">b</a> <a href="#cite_ref-WintersHuhtaniemi2017_60-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWintersHuhtaniemi2017" class="citation book cs1">Winters SJ, Huhtaniemi IT (25 April 2017). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=UFi-DgAAQBAJ&pg=PA307">Male Hypogonadism: Basic, Clinical and Therapeutic Principles</a>. Humana Press. pp. 307–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-319-53298-1" title="Special:BookSources/978-3-319-53298-1"><bdi>978-3-319-53298-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Male+Hypogonadism%3A+Basic%2C+Clinical+and+Therapeutic+Principles&rft.pages=307-&rft.pub=Humana+Press&rft.date=2017-04-25&rft.isbn=978-3-319-53298-1&rft.aulast=Winters&rft.aufirst=SJ&rft.au=Huhtaniemi%2C+IT&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DUFi-DgAAQBAJ%26pg%3DPA307&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid16915215-61"><a href="#cite_ref-pmid16915215_61-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNotelovitz2006" class="citation journal cs1">Notelovitz M (March 2006). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1682006">"Clinical opinion: the biologic and pharmacologic principles of estrogen therapy for symptomatic menopause"</a>. MedGenMed. 8 (1): 85. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1682006">1682006</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16915215">16915215</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=MedGenMed&rft.atitle=Clinical+opinion%3A+the+biologic+and+pharmacologic+principles+of+estrogen+therapy+for+symptomatic+menopause&rft.volume=8&rft.issue=1&rft.pages=85&rft.date=2006-03&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1682006%23id-name%3DPMC&rft_id=info%3Apmid%2F16915215&rft.aulast=Notelovitz&rft.aufirst=M&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1682006&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid22011208-62"><a href="#cite_ref-pmid22011208_62-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGoodman2012" class="citation journal cs1">Goodman MP (February 2012). "Are all estrogens created equal? A review of oral vs. transdermal therapy". Journal of Women's Health. 21 (2): 161–169. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1089%2Fjwh.2011.2839">10.1089/jwh.2011.2839</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/22011208">22011208</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Women%27s+Health&rft.atitle=Are+all+estrogens+created+equal%3F+A+review+of+oral+vs.+transdermal+therapy&rft.volume=21&rft.issue=2&rft.pages=161-169&rft.date=2012-02&rft_id=info%3Adoi%2F10.1089%2Fjwh.2011.2839&rft_id=info%3Apmid%2F22011208&rft.aulast=Goodman&rft.aufirst=MP&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid3242384-63">^ <a href="#cite_ref-pmid3242384_63-0">a</a> <a href="#cite_ref-pmid3242384_63-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFStegeCarlströmCollsteEriksson1988" class="citation journal cs1">Stege R, Carlström K, Collste L, Eriksson A, Henriksson P, Pousette A (1988). "Single drug polyestradiol phosphate therapy in prostatic cancer". American Journal of Clinical Oncology. 11 (Suppl 2): S101–S103. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1097%2F00000421-198801102-00024">10.1097/00000421-198801102-00024</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/3242384">3242384</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:32650111">32650111</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=American+Journal+of+Clinical+Oncology&rft.atitle=Single+drug+polyestradiol+phosphate+therapy+in+prostatic+cancer&rft.volume=11&rft.issue=Suppl+2&rft.pages=S101-S103&rft.date=1988&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A32650111%23id-name%3DS2CID&rft_id=info%3Apmid%2F3242384&rft_id=info%3Adoi%2F10.1097%2F00000421-198801102-00024&rft.aulast=Stege&rft.aufirst=R&rft.au=Carlstr%C3%B6m%2C+K&rft.au=Collste%2C+L&rft.au=Eriksson%2C+A&rft.au=Henriksson%2C+P&rft.au=Pousette%2C+A&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid2664738-64">^ <a href="#cite_ref-pmid2664738_64-0">a</a> <a href="#cite_ref-pmid2664738_64-1">b</a> <a href="#cite_ref-pmid2664738_64-2">c</a> <a href="#cite_ref-pmid2664738_64-3">d</a> <a href="#cite_ref-pmid2664738_64-4">e</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFvon_SchoultzCarlströmCollsteEriksson1989" class="citation journal cs1">von Schoultz B, Carlström K, Collste L, Eriksson A, Henriksson P, Pousette A, et al. (1989). "Estrogen therapy and liver function--metabolic effects of oral and parenteral administration". The Prostate. 14 (4): 389–395. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fpros.2990140410">10.1002/pros.2990140410</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/2664738">2664738</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:21510744">21510744</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Prostate&rft.atitle=Estrogen+therapy+and+liver+function--metabolic+effects+of+oral+and+parenteral+administration&rft.volume=14&rft.issue=4&rft.pages=389-395&rft.date=1989&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A21510744%23id-name%3DS2CID&rft_id=info%3Apmid%2F2664738&rft_id=info%3Adoi%2F10.1002%2Fpros.2990140410&rft.aulast=von+Schoultz&rft.aufirst=B&rft.au=Carlstr%C3%B6m%2C+K&rft.au=Collste%2C+L&rft.au=Eriksson%2C+A&rft.au=Henriksson%2C+P&rft.au=Pousette%2C+A&rft.au=Stege%2C+R&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid3817605-65">^ <a href="#cite_ref-pmid3817605_65-0">a</a> <a href="#cite_ref-pmid3817605_65-1">b</a> <a href="#cite_ref-pmid3817605_65-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFOttossonCarlströmJohanssonvon_Schoultz1986" class="citation journal cs1">Ottosson UB, Carlström K, Johansson BG, von Schoultz B (1986). "Estrogen induction of liver proteins and high-density lipoprotein cholesterol: comparison between estradiol valerate and ethinyl estradiol". Gynecologic and Obstetric Investigation. 22 (4): 198–205. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1159%2F000298914">10.1159/000298914</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/3817605">3817605</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Gynecologic+and+Obstetric+Investigation&rft.atitle=Estrogen+induction+of+liver+proteins+and+high-density+lipoprotein+cholesterol%3A+comparison+between+estradiol+valerate+and+ethinyl+estradiol&rft.volume=22&rft.issue=4&rft.pages=198-205&rft.date=1986&rft_id=info%3Adoi%2F10.1159%2F000298914&rft_id=info%3Apmid%2F3817605&rft.aulast=Ottosson&rft.aufirst=UB&rft.au=Carlstr%C3%B6m%2C+K&rft.au=Johansson%2C+BG&rft.au=von+Schoultz%2C+B&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid24256023-66">^ <a href="#cite_ref-pmid24256023_66-0">a</a> <a href="#cite_ref-pmid24256023_66-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTuroSmolskiEslerKujawa2014" class="citation journal cs1">Turo R, Smolski M, Esler R, Kujawa ML, Bromage SJ, Oakley N, et al. (February 2014). "Diethylstilboestrol for the treatment of prostate cancer: past, present and future". Scandinavian Journal of Urology. 48 (1): 4–14. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3109%2F21681805.2013.861508">10.3109/21681805.2013.861508</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/24256023">24256023</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:34563641">34563641</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Scandinavian+Journal+of+Urology&rft.atitle=Diethylstilboestrol+for+the+treatment+of+prostate+cancer%3A+past%2C+present+and+future&rft.volume=48&rft.issue=1&rft.pages=4-14&rft.date=2014-02&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A34563641%23id-name%3DS2CID&rft_id=info%3Apmid%2F24256023&rft_id=info%3Adoi%2F10.3109%2F21681805.2013.861508&rft.aulast=Turo&rft.aufirst=R&rft.au=Smolski%2C+M&rft.au=Esler%2C+R&rft.au=Kujawa%2C+ML&rft.au=Bromage%2C+SJ&rft.au=Oakley%2C+N&rft.au=Adeyoju%2C+A&rft.au=Brown%2C+SC&rft.au=Brough%2C+R&rft.au=Sinclair%2C+A&rft.au=Collins%2C+GN&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988">[<a href="/wiki/Wikipedia:Link_rot" title="Wikipedia:Link rot">dead link</a>‍] </li> <li id="cite_note-pmid24932461-67">^ <a href="#cite_ref-pmid24932461_67-0">a</a> <a href="#cite_ref-pmid24932461_67-1">b</a> <a href="#cite_ref-pmid24932461_67-2">c</a> <a href="#cite_ref-pmid24932461_67-3">d</a> <a href="#cite_ref-pmid24932461_67-4">e</a> <a href="#cite_ref-pmid24932461_67-5">f</a> <a href="#cite_ref-pmid24932461_67-6">g</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPhillipsShahDuongAbel2014" class="citation journal cs1">Phillips I, Shah SI, Duong T, Abel P, Langley RE (2014). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4052190">"Androgen Deprivation Therapy and the Re-emergence of Parenteral Estrogen in Prostate Cancer"</a>. Oncology & Hematology Review. 10 (1): 42–47. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.17925%2Fohr.2014.10.1.42">10.17925/ohr.2014.10.1.42</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4052190">4052190</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/24932461">24932461</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Oncology+%26+Hematology+Review&rft.atitle=Androgen+Deprivation+Therapy+and+the+Re-emergence+of+Parenteral+Estrogen+in+Prostate+Cancer&rft.volume=10&rft.issue=1&rft.pages=42-47&rft.date=2014&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4052190%23id-name%3DPMC&rft_id=info%3Apmid%2F24932461&rft_id=info%3Adoi%2F10.17925%2Fohr.2014.10.1.42&rft.aulast=Phillips&rft.aufirst=I&rft.au=Shah%2C+SI&rft.au=Duong%2C+T&rft.au=Abel%2C+P&rft.au=Langley%2C+RE&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4052190&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-HongHolland2010-68">^ <a href="#cite_ref-HongHolland2010_68-0">a</a> <a href="#cite_ref-HongHolland2010_68-1">b</a> <a href="#cite_ref-HongHolland2010_68-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHongHolland2010" class="citation book cs1">Hong WK, Holland JK (2010). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=R0FbhLsWHBEC&pg=PA753">Holland-Frei Cancer Medicine 8</a>. PMPH-USA. pp. 753–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-60795-014-1" title="Special:BookSources/978-1-60795-014-1"><bdi>978-1-60795-014-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Holland-Frei+Cancer+Medicine+8&rft.pages=753-&rft.pub=PMPH-USA&rft.date=2010&rft.isbn=978-1-60795-014-1&rft.aulast=Hong&rft.aufirst=WK&rft.au=Holland%2C+JK&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DR0FbhLsWHBEC%26pg%3DPA753&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid28667081-69">^ <a href="#cite_ref-pmid28667081_69-0">a</a> <a href="#cite_ref-pmid28667081_69-1">b</a> <a href="#cite_ref-pmid28667081_69-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRussellCheungGrossmann2017" class="citation journal cs1">Russell N, Cheung A, Grossmann M (August 2017). <a rel="nofollow" class="external text" href="https://doi.org/10.1530%2FERC-17-0153">"Estradiol for the mitigation of adverse effects of androgen deprivation therapy"</a>. Endocrine-Related Cancer. 24 (8): R297–R313. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1530%2FERC-17-0153">10.1530/ERC-17-0153</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/28667081">28667081</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Endocrine-Related+Cancer&rft.atitle=Estradiol+for+the+mitigation+of+adverse+effects+of+androgen+deprivation+therapy&rft.volume=24&rft.issue=8&rft.pages=R297-R313&rft.date=2017-08&rft_id=info%3Adoi%2F10.1530%2FERC-17-0153&rft_id=info%3Apmid%2F28667081&rft.aulast=Russell&rft.aufirst=N&rft.au=Cheung%2C+A&rft.au=Grossmann%2C+M&rft_id=https%3A%2F%2Fdoi.org%2F10.1530%252FERC-17-0153&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-TraunerJansen2004-70"><a href="#cite_ref-TraunerJansen2004_70-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTraunerJansen2004" class="citation book cs1">Trauner M, Jansen PJ (2004). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=ley1iZ-OongC&pg=PA260">Molecular Pathogenesis of Cholestasis</a>. Springer Science & Business Media. pp. 260–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-306-48240-3" title="Special:BookSources/978-0-306-48240-3"><bdi>978-0-306-48240-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Molecular+Pathogenesis+of+Cholestasis&rft.pages=260-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2004&rft.isbn=978-0-306-48240-3&rft.aulast=Trauner&rft.aufirst=M&rft.au=Jansen%2C+PJ&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dley1iZ-OongC%26pg%3DPA260&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-ClavienBaillie2008-71">^ <a href="#cite_ref-ClavienBaillie2008_71-0">a</a> <a href="#cite_ref-ClavienBaillie2008_71-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFClavienBaillie2008" class="citation book cs1">Clavien PA, Baillie J (15 April 2008). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=zF3iRcsxc3YC&pg=PA363">Diseases of the Gallbladder and Bile Ducts: Diagnosis and Treatment</a>. John Wiley & Sons. pp. 363–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-470-98697-4" title="Special:BookSources/978-0-470-98697-4"><bdi>978-0-470-98697-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Diseases+of+the+Gallbladder+and+Bile+Ducts%3A+Diagnosis+and+Treatment&rft.pages=363-&rft.pub=John+Wiley+%26+Sons&rft.date=2008-04-15&rft.isbn=978-0-470-98697-4&rft.aulast=Clavien&rft.aufirst=PA&rft.au=Baillie%2C+J&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DzF3iRcsxc3YC%26pg%3DPA363&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Kuhl1999-72">^ <a href="#cite_ref-Kuhl1999_72-0">a</a> <a href="#cite_ref-Kuhl1999_72-1">b</a> <a href="#cite_ref-Kuhl1999_72-2">c</a> <a href="#cite_ref-Kuhl1999_72-3">d</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKuhl1999" class="citation book cs1 cs1-prop-long-vol">Kuhl H (1999). "Hormonal Contraception". Estrogens and Antiestrogens II. Handbook of Experimental Pharmacology. Vol. 135 / 2. Springer Berlin Heidelberg. pp. 363–407. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-3-642-60107-1_18">10.1007/978-3-642-60107-1_18</a>. <a href="/wiki/EISSN_(identifier)" class="mw-redirect" title="EISSN (identifier)">eISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1865-0325">1865-0325</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-64261-6" title="Special:BookSources/978-3-642-64261-6"><bdi>978-3-642-64261-6</bdi></a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0171-2004">0171-2004</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Hormonal+Contraception&rft.btitle=Estrogens+and+Antiestrogens+II&rft.series=Handbook+of+Experimental+Pharmacology&rft.pages=363-407&rft.pub=Springer+Berlin+Heidelberg&rft.date=1999&rft_id=info%3Adoi%2F10.1007%2F978-3-642-60107-1_18&rft.issn=0171-2004&rft.eissn=1865-0325&rft.isbn=978-3-642-64261-6&rft.aulast=Kuhl&rft.aufirst=H&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-O'BrienBruce2010-73"><a href="#cite_ref-O'BrienBruce2010_73-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFO'BrienBruce2010" class="citation book cs1">O'Brien PJ, Bruce WR (2010). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=UaLR0RSuXvsC&pg=PA302">Endogenous Toxins: Diet, Genetics, Disease and Treatment</a>. John Wiley & Sons. pp. 302–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-527-32363-0" title="Special:BookSources/978-3-527-32363-0"><bdi>978-3-527-32363-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Endogenous+Toxins%3A+Diet%2C+Genetics%2C+Disease+and+Treatment&rft.pages=302-&rft.pub=John+Wiley+%26+Sons&rft.date=2010&rft.isbn=978-3-527-32363-0&rft.aulast=O%27Brien&rft.aufirst=PJ&rft.au=Bruce%2C+WR&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DUaLR0RSuXvsC%26pg%3DPA302&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid2086334-74">^ <a href="#cite_ref-pmid2086334_74-0">a</a> <a href="#cite_ref-pmid2086334_74-1">b</a> <a href="#cite_ref-pmid2086334_74-2">c</a> <a href="#cite_ref-pmid2086334_74-3">d</a> <a href="#cite_ref-pmid2086334_74-4">e</a> <a href="#cite_ref-pmid2086334_74-5">f</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKuhl1990" class="citation journal cs1 cs1-prop-foreign-lang-source">Kuhl H (December 1990). "[Ovulation inhibitors: the significance of estrogen dose]" [Ovulation inhibitors: the significance of estrogen dose]. Geburtshilfe und Frauenheilkunde (in German). 50 (12): 910–922. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1055%2Fs-2008-1026392">10.1055/s-2008-1026392</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/2086334">2086334</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:73398961">73398961</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Geburtshilfe+und+Frauenheilkunde&rft.atitle=%5BOvulation+inhibitors%3A+the+significance+of+estrogen+dose%5D&rft.volume=50&rft.issue=12&rft.pages=910-922&rft.date=1990-12&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A73398961%23id-name%3DS2CID&rft_id=info%3Apmid%2F2086334&rft_id=info%3Adoi%2F10.1055%2Fs-2008-1026392&rft.aulast=Kuhl&rft.aufirst=H&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid30020636-75"><a href="#cite_ref-pmid30020636_75-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFShreenathKahloon2022" class="citation book cs1">Shreenath AP, Kahloon A (January 2022). "Hepatocellular Adenoma". <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/books/NBK513264/">Hepatic Adenoma</a>. StatPearls. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/30020636">30020636</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Hepatocellular+Adenoma&rft.btitle=Hepatic+Adenoma&rft.pub=StatPearls&rft.date=2022-01&rft_id=info%3Apmid%2F30020636&rft.aulast=Shreenath&rft.aufirst=AP&rft.au=Kahloon%2C+A&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fbooks%2FNBK513264%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid17261770-76">^ <a href="#cite_ref-pmid17261770_76-0">a</a> <a href="#cite_ref-pmid17261770_76-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGiannitrapaniSoresiLa_SpadaCervello2006" class="citation journal cs1">Giannitrapani L, Soresi M, La Spada E, Cervello M, D'Alessandro N, Montalto G (November 2006). "Sex hormones and risk of liver tumor". Annals of the New York Academy of Sciences. 1089 (1): 228–236. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2006NYASA1089..228G">2006NYASA1089..228G</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1196%2Fannals.1386.044">10.1196/annals.1386.044</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/17261770">17261770</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:7932937">7932937</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annals+of+the+New+York+Academy+of+Sciences&rft.atitle=Sex+hormones+and+risk+of+liver+tumor&rft.volume=1089&rft.issue=1&rft.pages=228-236&rft.date=2006-11&rft_id=info%3Adoi%2F10.1196%2Fannals.1386.044&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A7932937%23id-name%3DS2CID&rft_id=info%3Apmid%2F17261770&rft_id=info%3Abibcode%2F2006NYASA1089..228G&rft.aulast=Giannitrapani&rft.aufirst=L&rft.au=Soresi%2C+M&rft.au=La+Spada%2C+E&rft.au=Cervello%2C+M&rft.au=D%27Alessandro%2C+N&rft.au=Montalto%2C+G&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid31009688-77"><a href="#cite_ref-pmid31009688_77-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPonnatapuraKielarBurkeLockhart2019" class="citation journal cs1">Ponnatapura J, Kielar A, Burke LM, Lockhart ME, Abualruz AR, Tappouni R, et al. (July 2019). "Hepatic complications of oral contraceptive pills and estrogen on MRI: Controversies and update - Adenoma and beyond". Magnetic Resonance Imaging. 60: 110–121. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.mri.2019.04.010">10.1016/j.mri.2019.04.010</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/31009688">31009688</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:128359413">128359413</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Magnetic+Resonance+Imaging&rft.atitle=Hepatic+complications+of+oral+contraceptive+pills+and+estrogen+on+MRI%3A+Controversies+and+update+-+Adenoma+and+beyond&rft.volume=60&rft.pages=110-121&rft.date=2019-07&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A128359413%23id-name%3DS2CID&rft_id=info%3Apmid%2F31009688&rft_id=info%3Adoi%2F10.1016%2Fj.mri.2019.04.010&rft.aulast=Ponnatapura&rft.aufirst=J&rft.au=Kielar%2C+A&rft.au=Burke%2C+LM&rft.au=Lockhart%2C+ME&rft.au=Abualruz%2C+AR&rft.au=Tappouni%2C+R&rft.au=Lalwani%2C+N&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid18814084-78"><a href="#cite_ref-pmid18814084_78-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPerarnauBacq2008" class="citation journal cs1">Perarnau JM, Bacq Y (August 2008). "Hepatic vascular involvement related to pregnancy, oral contraceptives, and estrogen replacement therapy". Seminars in Liver Disease. 28 (3): 315–327. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1055%2Fs-0028-1085099">10.1055/s-0028-1085099</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/18814084">18814084</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:260318275">260318275</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Seminars+in+Liver+Disease&rft.atitle=Hepatic+vascular+involvement+related+to+pregnancy%2C+oral+contraceptives%2C+and+estrogen+replacement+therapy&rft.volume=28&rft.issue=3&rft.pages=315-327&rft.date=2008-08&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A260318275%23id-name%3DS2CID&rft_id=info%3Apmid%2F18814084&rft_id=info%3Adoi%2F10.1055%2Fs-0028-1085099&rft.aulast=Perarnau&rft.aufirst=JM&rft.au=Bacq%2C+Y&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Blaustein2013-79">^ <a href="#cite_ref-Blaustein2013_79-0">a</a> <a href="#cite_ref-Blaustein2013_79-1">b</a> <a href="#cite_ref-Blaustein2013_79-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBlaustein2013" class="citation book cs1">Blaustein A (11 November 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=4MXSBwAAQBAJ&pg=PA291">Pathology of the Female Genital Tract</a>. Springer Science & Business Media. pp. 291–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4757-1767-9" title="Special:BookSources/978-1-4757-1767-9"><bdi>978-1-4757-1767-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Pathology+of+the+Female+Genital+Tract&rft.pages=291-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2013-11-11&rft.isbn=978-1-4757-1767-9&rft.aulast=Blaustein&rft.aufirst=A&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D4MXSBwAAQBAJ%26pg%3DPA291&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-SurwitAlberts2012-80"><a href="#cite_ref-SurwitAlberts2012_80-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSurwitAlberts2012" class="citation book cs1">Surwit EA, Alberts D (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=jbshBQAAQBAJ&pg=PA11">Endometrial Cancer</a>. Springer Science & Business Media. pp. 11–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4613-0867-6" title="Special:BookSources/978-1-4613-0867-6"><bdi>978-1-4613-0867-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Endometrial+Cancer&rft.pages=11-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-1-4613-0867-6&rft.aulast=Surwit&rft.aufirst=EA&rft.au=Alberts%2C+D&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DjbshBQAAQBAJ%26pg%3DPA11&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-:0-81">^ <a href="#cite_ref-:0_81-0">a</a> <a href="#cite_ref-:0_81-1">b</a> <a href="#cite_ref-:0_81-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKiddBlanchfieldMillsPalace2007" class="citation journal cs1">Kidd KA, Blanchfield PJ, Mills KH, Palace VP, Evans RE, Lazorchak JM, et al. (May 2007). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1874224">"Collapse of a fish population after exposure to a synthetic estrogen"</a>. Proceedings of the National Academy of Sciences of the United States of America. 104 (21): 8897–8901. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2007PNAS..104.8897K">2007PNAS..104.8897K</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1073%2Fpnas.0609568104">10.1073/pnas.0609568104</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1874224">1874224</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/17517636">17517636</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Proceedings+of+the+National+Academy+of+Sciences+of+the+United+States+of+America&rft.atitle=Collapse+of+a+fish+population+after+exposure+to+a+synthetic+estrogen&rft.volume=104&rft.issue=21&rft.pages=8897-8901&rft.date=2007-05&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1874224%23id-name%3DPMC&rft_id=info%3Apmid%2F17517636&rft_id=info%3Adoi%2F10.1073%2Fpnas.0609568104&rft_id=info%3Abibcode%2F2007PNAS..104.8897K&rft.aulast=Kidd&rft.aufirst=KA&rft.au=Blanchfield%2C+PJ&rft.au=Mills%2C+KH&rft.au=Palace%2C+VP&rft.au=Evans%2C+RE&rft.au=Lazorchak%2C+JM&rft.au=Flick%2C+RW&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1874224&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-:1-82">^ <a href="#cite_ref-:1_82-0">a</a> <a href="#cite_ref-:1_82-1">b</a> <a href="#cite_ref-:1_82-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFParkKidd2005" class="citation journal cs1">Park BJ, Kidd K (August 2005). "Effects of the synthetic estrogen ethinylestradiol on early life stages of mink frogs and green frogs in the wild and in situ". Environmental Toxicology and Chemistry. 24 (8): 2027–2036. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2005EnvTC..24.2027P">2005EnvTC..24.2027P</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1897%2F04-227R.1">10.1897/04-227R.1</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16152976">16152976</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:32669410">32669410</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Environmental+Toxicology+and+Chemistry&rft.atitle=Effects+of+the+synthetic+estrogen+ethinylestradiol+on+early+life+stages+of+mink+frogs+and+green+frogs+in+the+wild+and+in+situ&rft.volume=24&rft.issue=8&rft.pages=2027-2036&rft.date=2005-08&rft_id=info%3Adoi%2F10.1897%2F04-227R.1&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A32669410%23id-name%3DS2CID&rft_id=info%3Apmid%2F16152976&rft_id=info%3Abibcode%2F2005EnvTC..24.2027P&rft.aulast=Park&rft.aufirst=BJ&rft.au=Kidd%2C+K&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-83"><a href="#cite_ref-83">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWangSanchezFranklinEvans2004" class="citation journal cs1">Wang B, Sanchez RI, Franklin RB, Evans DC, Huskey SE (November 2004). "The involvement of CYP3A4 and CYP2C9 in the metabolism of 17 alpha-ethinylestradiol". Drug Metabolism and Disposition. 32 (11): 1209–1212. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1124%2Fdmd.104.000182">10.1124/dmd.104.000182</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/15304426">15304426</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:86245855">86245855</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Drug+Metabolism+and+Disposition&rft.atitle=The+involvement+of+CYP3A4+and+CYP2C9+in+the+metabolism+of+17+alpha-ethinylestradiol&rft.volume=32&rft.issue=11&rft.pages=1209-1212&rft.date=2004-11&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A86245855%23id-name%3DS2CID&rft_id=info%3Apmid%2F15304426&rft_id=info%3Adoi%2F10.1124%2Fdmd.104.000182&rft.aulast=Wang&rft.aufirst=B&rft.au=Sanchez%2C+RI&rft.au=Franklin%2C+RB&rft.au=Evans%2C+DC&rft.au=Huskey%2C+SE&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid17253885-84">^ <a href="#cite_ref-pmid17253885_84-0">a</a> <a href="#cite_ref-pmid17253885_84-1">b</a> <a href="#cite_ref-pmid17253885_84-2">c</a> <a href="#cite_ref-pmid17253885_84-3">d</a> <a href="#cite_ref-pmid17253885_84-4">e</a> <a href="#cite_ref-pmid17253885_84-5">f</a> <a href="#cite_ref-pmid17253885_84-6">g</a> <a href="#cite_ref-pmid17253885_84-7">h</a> <a href="#cite_ref-pmid17253885_84-8">i</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFZhangCuiWangHan2007" class="citation journal cs1">Zhang H, Cui D, Wang B, Han YH, Balimane P, Yang Z, et al. (2007). "Pharmacokinetic drug interactions involving 17alpha-ethinylestradiol: a new look at an old drug". Clinical Pharmacokinetics. 46 (2): 133–157. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.2165%2F00003088-200746020-00003">10.2165/00003088-200746020-00003</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/17253885">17253885</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:71784426">71784426</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Clinical+Pharmacokinetics&rft.atitle=Pharmacokinetic+drug+interactions+involving+17alpha-ethinylestradiol%3A+a+new+look+at+an+old+drug&rft.volume=46&rft.issue=2&rft.pages=133-157&rft.date=2007&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A71784426%23id-name%3DS2CID&rft_id=info%3Apmid%2F17253885&rft_id=info%3Adoi%2F10.2165%2F00003088-200746020-00003&rft.aulast=Zhang&rft.aufirst=H&rft.au=Cui%2C+D&rft.au=Wang%2C+B&rft.au=Han%2C+YH&rft.au=Balimane%2C+P&rft.au=Yang%2C+Z&rft.au=Sinz%2C+M&rft.au=Rodrigues%2C+AD&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid16554039-85"><a href="#cite_ref-pmid16554039_85-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFEscandePillonServantCravedi2006" class="citation journal cs1">Escande A, Pillon A, Servant N, Cravedi JP, Larrea F, Muhn P, et al. (May 2006). "Evaluation of ligand selectivity using reporter cell lines stably expressing estrogen receptor alpha or beta". Biochemical Pharmacology. 71 (10): 1459–1469. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.bcp.2006.02.002">10.1016/j.bcp.2006.02.002</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16554039">16554039</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Biochemical+Pharmacology&rft.atitle=Evaluation+of+ligand+selectivity+using+reporter+cell+lines+stably+expressing+estrogen+receptor+alpha+or+beta&rft.volume=71&rft.issue=10&rft.pages=1459-1469&rft.date=2006-05&rft_id=info%3Adoi%2F10.1016%2Fj.bcp.2006.02.002&rft_id=info%3Apmid%2F16554039&rft.aulast=Escande&rft.aufirst=A&rft.au=Pillon%2C+A&rft.au=Servant%2C+N&rft.au=Cravedi%2C+JP&rft.au=Larrea%2C+F&rft.au=Muhn%2C+P&rft.au=Nicolas%2C+JC&rft.au=Cavaill%C3%A8s%2C+V&rft.au=Balaguer%2C+P&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid21321128-86"><a href="#cite_ref-pmid21321128_86-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJeyakumarCarlsonGuntherKatzenellenbogen2011" class="citation journal cs1">Jeyakumar M, Carlson KE, Gunther JR, Katzenellenbogen JA (April 2011). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3075970">"Exploration of dimensions of estrogen potency: parsing ligand binding and coactivator binding affinities"</a>. The Journal of Biological Chemistry. 286 (15): 12971–12982. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1074%2Fjbc.M110.205112">10.1074/jbc.M110.205112</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3075970">3075970</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/21321128">21321128</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Biological+Chemistry&rft.atitle=Exploration+of+dimensions+of+estrogen+potency%3A+parsing+ligand+binding+and+coactivator+binding+affinities&rft.volume=286&rft.issue=15&rft.pages=12971-12982&rft.date=2011-04&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3075970%23id-name%3DPMC&rft_id=info%3Apmid%2F21321128&rft_id=info%3Adoi%2F10.1074%2Fjbc.M110.205112&rft.aulast=Jeyakumar&rft.aufirst=M&rft.au=Carlson%2C+KE&rft.au=Gunther%2C+JR&rft.au=Katzenellenbogen%2C+JA&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3075970&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid26023144-87"><a href="#cite_ref-pmid26023144_87-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFProssnitzArterburn2015" class="citation journal cs1">Prossnitz ER, Arterburn JB (July 2015). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4485017">"International Union of Basic and Clinical Pharmacology. XCVII. G Protein-Coupled Estrogen Receptor and Its Pharmacologic Modulators"</a>. Pharmacological Reviews. 67 (3): 505–540. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1124%2Fpr.114.009712">10.1124/pr.114.009712</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4485017">4485017</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/26023144">26023144</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pharmacological+Reviews&rft.atitle=International+Union+of+Basic+and+Clinical+Pharmacology.+XCVII.+G+Protein-Coupled+Estrogen+Receptor+and+Its+Pharmacologic+Modulators&rft.volume=67&rft.issue=3&rft.pages=505-540&rft.date=2015-07&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4485017%23id-name%3DPMC&rft_id=info%3Apmid%2F26023144&rft_id=info%3Adoi%2F10.1124%2Fpr.114.009712&rft.aulast=Prossnitz&rft.aufirst=ER&rft.au=Arterburn%2C+JB&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4485017&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid20403194-88"><a href="#cite_ref-pmid20403194_88-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFYatesLiChlebeckOffner2010" class="citation journal cs1">Yates MA, Li Y, Chlebeck PJ, Offner H (April 2010). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2864220">"GPR30, but not estrogen receptor-alpha, is crucial in the treatment of experimental autoimmune encephalomyelitis by oral ethinyl estradiol"</a>. BMC Immunology. 11: 20. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1186%2F1471-2172-11-20">10.1186/1471-2172-11-20</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2864220">2864220</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/20403194">20403194</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=BMC+Immunology&rft.atitle=GPR30%2C+but+not+estrogen+receptor-alpha%2C+is+crucial+in+the+treatment+of+experimental+autoimmune+encephalomyelitis+by+oral+ethinyl+estradiol&rft.volume=11&rft.pages=20&rft.date=2010-04&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2864220%23id-name%3DPMC&rft_id=info%3Apmid%2F20403194&rft_id=info%3Adoi%2F10.1186%2F1471-2172-11-20&rft.aulast=Yates&rft.aufirst=MA&rft.au=Li%2C+Y&rft.au=Chlebeck%2C+PJ&rft.au=Offner%2C+H&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2864220&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid21844907-89"><a href="#cite_ref-pmid21844907_89-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFProssnitzBarton2011" class="citation journal cs1">Prossnitz ER, Barton M (August 2011). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3474542">"The G-protein-coupled estrogen receptor GPER in health and disease"</a>. Nature Reviews. Endocrinology. 7 (12): 715–726. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fnrendo.2011.122">10.1038/nrendo.2011.122</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3474542">3474542</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/21844907">21844907</a>. <q>Further research showed that the therapeutic effect of ethynylestradiol in established EAE was mediated via GPER, but not via ERα, and possibly involved production of the anti-inflammatory cytokine Il‑10.115</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nature+Reviews.+Endocrinology&rft.atitle=The+G-protein-coupled+estrogen+receptor+GPER+in+health+and+disease&rft.volume=7&rft.issue=12&rft.pages=715-726&rft.date=2011-08&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3474542%23id-name%3DPMC&rft_id=info%3Apmid%2F21844907&rft_id=info%3Adoi%2F10.1038%2Fnrendo.2011.122&rft.aulast=Prossnitz&rft.aufirst=ER&rft.au=Barton%2C+M&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3474542&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid24530924-90"><a href="#cite_ref-pmid24530924_90-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFProssnitzBarton2014" class="citation journal cs1">Prossnitz ER, Barton M (May 2014). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4040308">"Estrogen biology: new insights into GPER function and clinical opportunities"</a>. Molecular and Cellular Endocrinology. 389 (1–2): 71–83. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.mce.2014.02.002">10.1016/j.mce.2014.02.002</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4040308">4040308</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/24530924">24530924</a>. <q>In addition, the therapeutic effect of ethinyl estradiol in established disease was demonstrated to require expression of GPER but not ERα, and was associated with the production of the anti-inflammatory cytokine IL-10 (Yates et al., 2010).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Molecular+and+Cellular+Endocrinology&rft.atitle=Estrogen+biology%3A+new+insights+into+GPER+function+and+clinical+opportunities&rft.volume=389&rft.issue=1%E2%80%932&rft.pages=71-83&rft.date=2014-05&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4040308%23id-name%3DPMC&rft_id=info%3Apmid%2F24530924&rft_id=info%3Adoi%2F10.1016%2Fj.mce.2014.02.002&rft.aulast=Prossnitz&rft.aufirst=ER&rft.au=Barton%2C+M&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4040308&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-QuaynorStradtman2013-91"><a href="#cite_ref-QuaynorStradtman2013_91-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFQuaynorStradtmanKimShen2013" class="citation journal cs1">Quaynor SD, Stradtman EW, Kim HG, Shen Y, Chorich LP, Schreihofer DA, et al. (July 2013). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3823379">"Delayed puberty and estrogen resistance in a woman with estrogen receptor α variant"</a>. The New England Journal of Medicine. 369 (2): 164–171. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1056%2FNEJMoa1303611">10.1056/NEJMoa1303611</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3823379">3823379</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/23841731">23841731</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+New+England+Journal+of+Medicine&rft.atitle=Delayed+puberty+and+estrogen+resistance+in+a+woman+with+estrogen+receptor+%CE%B1+variant&rft.volume=369&rft.issue=2&rft.pages=164-171&rft.date=2013-07&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3823379%23id-name%3DPMC&rft_id=info%3Apmid%2F23841731&rft_id=info%3Adoi%2F10.1056%2FNEJMoa1303611&rft.aulast=Quaynor&rft.aufirst=SD&rft.au=Stradtman%2C+EW&rft.au=Kim%2C+HG&rft.au=Shen%2C+Y&rft.au=Chorich%2C+LP&rft.au=Schreihofer%2C+DA&rft.au=Layman%2C+LC&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3823379&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-CraigStitzel2004-92"><a href="#cite_ref-CraigStitzel2004_92-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCraigStitzel2004" class="citation book cs1">Craig CR, Stitzel RE (2004). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=KqA29hQ-m3AC&pg=PA708">Modern Pharmacology with Clinical Applications</a>. Lippincott Williams & Wilkins. pp. 708–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7817-3762-3" title="Special:BookSources/978-0-7817-3762-3"><bdi>978-0-7817-3762-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Modern+Pharmacology+with+Clinical+Applications&rft.pages=708-&rft.pub=Lippincott+Williams+%26+Wilkins&rft.date=2004&rft.isbn=978-0-7817-3762-3&rft.aulast=Craig&rft.aufirst=CR&rft.au=Stitzel%2C+RE&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DKqA29hQ-m3AC%26pg%3DPA708&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-AllahbadiaAgrawal2007-93"><a href="#cite_ref-AllahbadiaAgrawal2007_93-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAllahbadiaAgrawal2007" class="citation book cs1">Allahbadia G, Agrawal R (2007). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=HX0JxcrWJvAC&pg=PA257">Polycystic Ovary Syndrome</a>. Anshan. pp. 257–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-904798-74-3" title="Special:BookSources/978-1-904798-74-3"><bdi>978-1-904798-74-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Polycystic+Ovary+Syndrome&rft.pages=257-&rft.pub=Anshan&rft.date=2007&rft.isbn=978-1-904798-74-3&rft.aulast=Allahbadia&rft.aufirst=G&rft.au=Agrawal%2C+R&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DHX0JxcrWJvAC%26pg%3DPA257&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-GomelMunro1990-94">^ <a href="#cite_ref-GomelMunro1990_94-0">a</a> <a href="#cite_ref-GomelMunro1990_94-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGomelMunroRowe1990" class="citation book cs1">Gomel V, Munro MG, Rowe TC (1990). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=8-JsAAAAMAAJ">Gynecology: a practical approach</a>. Williams & Wilkins. p. 132,134. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-683-03631-2" title="Special:BookSources/978-0-683-03631-2"><bdi>978-0-683-03631-2</bdi></a>. <q>The synthetic estrogen, ethinyl estradiol, more commonly used in oral contraceptives, has a biological activity 100 times that of the native and conjugated substances.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Gynecology%3A+a+practical+approach&rft.pages=132%2C134&rft.pub=Williams+%26+Wilkins&rft.date=1990&rft.isbn=978-0-683-03631-2&rft.aulast=Gomel&rft.aufirst=V&rft.au=Munro%2C+MG&rft.au=Rowe%2C+TC&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D8-JsAAAAMAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Shoupe2007-95">^ <a href="#cite_ref-Shoupe2007_95-0">a</a> <a href="#cite_ref-Shoupe2007_95-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFShoupe2007" class="citation book cs1">Shoupe D (7 November 2007). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=sczb0Tk_2IwC&pg=PA23">The Handbook of Contraception: A Guide for Practical Management</a>. Springer Science & Business Media. pp. 23–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-59745-150-5" title="Special:BookSources/978-1-59745-150-5"><bdi>978-1-59745-150-5</bdi></a>. <q>EE2 has about 100 times the potency of an equivalent weight of conjugated equine estrogen or estrone sulfate for stimulating synthesis of hepatic proteins. [...] EE2 is about 1.7 times as potent as the same weight of mestranol.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Handbook+of+Contraception%3A+A+Guide+for+Practical+Management&rft.pages=23-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2007-11-07&rft.isbn=978-1-59745-150-5&rft.aulast=Shoupe&rft.aufirst=D&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dsczb0Tk_2IwC%26pg%3DPA23&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-McConaghy2013-96"><a href="#cite_ref-McConaghy2013_96-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMcConaghy2013" class="citation book cs1">McConaghy N (21 November 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=eVD0BwAAQBAJ&pg=PA177">Sexual Behavior: Problems and Management</a>. Springer Science & Business Media. pp. 177–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4899-1133-9" title="Special:BookSources/978-1-4899-1133-9"><bdi>978-1-4899-1133-9</bdi></a>. <q>Meyer et al. found that ethinyl estradiol was 75 to 100 times more potent than conjugated estrogen on the basis of the doses required to lower testosterone to the adult female range, 0.1 mg of the former and 7.5 to 10 mg of the latter being necessary.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Sexual+Behavior%3A+Problems+and+Management&rft.pages=177-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2013-11-21&rft.isbn=978-1-4899-1133-9&rft.aulast=McConaghy&rft.aufirst=N&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DeVD0BwAAQBAJ%26pg%3DPA177&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-ChabnerLongo1996-97"><a href="#cite_ref-ChabnerLongo1996_97-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChabnerLongo1996" class="citation book cs1">Chabner B, Longo DL (1996). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=TZNrAAAAMAAJ">Cancer Chemotherapy and Biotherapy: Principles and Practice</a>. Lippincott-Raven Publishers. p. 186. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-397-51418-2" title="Special:BookSources/978-0-397-51418-2"><bdi>978-0-397-51418-2</bdi></a>. <q>The relative potency of several estrogens has been assayed by determination of effects on plasma FSH, a measure of the systemic effect, and by increases in SHBG, CBG, and angiotensinogen, all of which indicate the hepatic effect. Piperazine estrone sulfate and micronized estradiol were equipotent with respect to increases in SHBG, whereas conjugated estrogens were 3.2-fold more potent, DES was 28.4-fold more potent, and ethinyl estradiol was 600-fold more potent. With respect to decreased FSH, conjugated estrogens were 1.4-fold, DES was 3.8-fold, and ethinyl estradiol was 80 to 200-fold more potent than was piperazine estrone sulfate.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Cancer+Chemotherapy+and+Biotherapy%3A+Principles+and+Practice&rft.pages=186&rft.pub=Lippincott-Raven+Publishers&rft.date=1996&rft.isbn=978-0-397-51418-2&rft.aulast=Chabner&rft.aufirst=B&rft.au=Longo%2C+DL&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DTZNrAAAAMAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid6291391-98">^ <a href="#cite_ref-pmid6291391_98-0">a</a> <a href="#cite_ref-pmid6291391_98-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMashchakLoboDozono-TakanoEggena1982" class="citation journal cs1">Mashchak CA, Lobo RA, Dozono-Takano R, Eggena P, Nakamura RM, Brenner PF, et al. (November 1982). "Comparison of pharmacodynamic properties of various estrogen formulations". American Journal of Obstetrics and Gynecology. 144 (5): 511–518. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0002-9378%2882%2990218-6">10.1016/0002-9378(82)90218-6</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/6291391">6291391</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=American+Journal+of+Obstetrics+and+Gynecology&rft.atitle=Comparison+of+pharmacodynamic+properties+of+various+estrogen+formulations&rft.volume=144&rft.issue=5&rft.pages=511-518&rft.date=1982-11&rft_id=info%3Adoi%2F10.1016%2F0002-9378%2882%2990218-6&rft_id=info%3Apmid%2F6291391&rft.aulast=Mashchak&rft.aufirst=CA&rft.au=Lobo%2C+RA&rft.au=Dozono-Takano%2C+R&rft.au=Eggena%2C+P&rft.au=Nakamura%2C+RM&rft.au=Brenner%2C+PF&rft.au=Mishell%2C+DR&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid2215269-99"><a href="#cite_ref-pmid2215269_99-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLauritzen1990" class="citation journal cs1">Lauritzen C (September 1990). "Clinical use of oestrogens and progestogens". Maturitas. 12 (3): 199–214. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0378-5122%2890%2990004-P">10.1016/0378-5122(90)90004-P</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/2215269">2215269</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Maturitas&rft.atitle=Clinical+use+of+oestrogens+and+progestogens&rft.volume=12&rft.issue=3&rft.pages=199-214&rft.date=1990-09&rft_id=info%3Adoi%2F10.1016%2F0378-5122%2890%2990004-P&rft_id=info%3Apmid%2F2215269&rft.aulast=Lauritzen&rft.aufirst=C&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid559617-100"><a href="#cite_ref-pmid559617_100-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLauritzen1977" class="citation journal cs1 cs1-prop-foreign-lang-source">Lauritzen C (June 1977). "[Estrogen thearpy in practice. 3. Estrogen preparations and combination preparations]" [Estrogen therapy in practice. 3. Estrogen preparations and combination preparations]. Fortschritte Der Medizin (in German). 95 (21): 1388–92. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/559617">559617</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Fortschritte+Der+Medizin&rft.atitle=%5BEstrogen+thearpy+in+practice.+3.+Estrogen+preparations+and+combination+preparations%5D&rft.volume=95&rft.issue=21&rft.pages=1388-92&rft.date=1977-06&rft_id=info%3Apmid%2F559617&rft.aulast=Lauritzen&rft.aufirst=C&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-WolfSchneider2013-101"><a href="#cite_ref-WolfSchneider2013_101-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWolfSchneider2013" class="citation book cs1">Wolf AS, Schneider HP (12 March 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books-id=IArLBgAAQBAJ&pg=PA78">Östrogene in Diagnostik und Therapie</a>. Springer-Verlag. pp. 78–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-75101-1" title="Special:BookSources/978-3-642-75101-1"><bdi>978-3-642-75101-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=%C3%96strogene+in+Diagnostik+und+Therapie&rft.pages=78-&rft.pub=Springer-Verlag&rft.date=2013-03-12&rft.isbn=978-3-642-75101-1&rft.aulast=Wolf&rft.aufirst=AS&rft.au=Schneider%2C+HP&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks-id%3DIArLBgAAQBAJ%26pg%3DPA78&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-GöretzlehnerLauritzen2012-102"><a href="#cite_ref-GöretzlehnerLauritzen2012_102-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGöretzlehnerLauritzenRömerRossmanith2012" class="citation book cs1">Göretzlehner G, Lauritzen C, Römer T, Rossmanith W (1 January 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books-id=TIs2WhfYzZ4C&pg=PA44">Praktische Hormontherapie in der Gynäkologie</a>. Walter de Gruyter. pp. 44–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-11-024568-4" title="Special:BookSources/978-3-11-024568-4"><bdi>978-3-11-024568-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Praktische+Hormontherapie+in+der+Gyn%C3%A4kologie&rft.pages=44-&rft.pub=Walter+de+Gruyter&rft.date=2012-01-01&rft.isbn=978-3-11-024568-4&rft.aulast=G%C3%B6retzlehner&rft.aufirst=G&rft.au=Lauritzen%2C+C&rft.au=R%C3%B6mer%2C+T&rft.au=Rossmanith%2C+W&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks-id%3DTIs2WhfYzZ4C%26pg%3DPA44&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-KnörrBeller2013-103"><a href="#cite_ref-KnörrBeller2013_103-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKnörrBellerLauritzen2013" class="citation book cs1">Knörr K, Beller FK, Lauritzen C (17 April 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books-id=ACybBwAAQBAJ&pg=PA212">Lehrbuch der Gynäkologie</a>. Springer-Verlag. pp. 212–213. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-662-00942-0" title="Special:BookSources/978-3-662-00942-0"><bdi>978-3-662-00942-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Lehrbuch+der+Gyn%C3%A4kologie&rft.pages=212-213&rft.pub=Springer-Verlag&rft.date=2013-04-17&rft.isbn=978-3-662-00942-0&rft.aulast=Kn%C3%B6rr&rft.aufirst=K&rft.au=Beller%2C+FK&rft.au=Lauritzen%2C+C&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks-id%3DACybBwAAQBAJ%26pg%3DPA212&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-HorskyPresl1981-104"><a href="#cite_ref-HorskyPresl1981_104-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHorskýPresl1981" class="citation book cs1">Horský J, Presl J (1981). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=7IrpCAAAQBAJ&pg=PA310">"Hormonal Treatment of Disorders of the Menstrual Cycle"</a>. In Horsky J, Presl J (eds.). Ovarian Function and its Disorders: Diagnosis and Therapy. Springer Science & Business Media. pp. 309–332. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-94-009-8195-9_11">10.1007/978-94-009-8195-9_11</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-94-009-8195-9" title="Special:BookSources/978-94-009-8195-9"><bdi>978-94-009-8195-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Hormonal+Treatment+of+Disorders+of+the+Menstrual+Cycle&rft.btitle=Ovarian+Function+and+its+Disorders%3A+Diagnosis+and+Therapy&rft.pages=309-332&rft.pub=Springer+Science+%26+Business+Media&rft.date=1981&rft_id=info%3Adoi%2F10.1007%2F978-94-009-8195-9_11&rft.isbn=978-94-009-8195-9&rft.aulast=Horsk%C3%BD&rft.aufirst=J&rft.au=Presl%2C+J&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D7IrpCAAAQBAJ%26pg%3DPA310&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Pschyrembel1968-105"><a href="#cite_ref-Pschyrembel1968_105-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPschyrembel1968" class="citation book cs1">Pschyrembel W (1968). <a rel="nofollow" class="external text" href="https://books.google.com/books-id=vVaTnHDFzZ0C&pg=PA598">Praktische Gynäkologie: für Studierende und Ärzte</a>. Walter de Gruyter. pp. 598–599. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-11-150424-7" title="Special:BookSources/978-3-11-150424-7"><bdi>978-3-11-150424-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Praktische+Gyn%C3%A4kologie%3A+f%C3%BCr+Studierende+und+%C3%84rzte&rft.pages=598-599&rft.pub=Walter+de+Gruyter&rft.date=1968&rft.isbn=978-3-11-150424-7&rft.aulast=Pschyrembel&rft.aufirst=W&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks-id%3DvVaTnHDFzZ0C%26pg%3DPA598&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid779393-106"><a href="#cite_ref-pmid779393_106-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLauritzen1976" class="citation journal cs1">Lauritzen CH (January 1976). "The female climacteric syndrome: significance, problems, treatment". Acta Obstetricia Et Gynecologica Scandinavica. Supplement. 51: 47–61. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3109%2F00016347509156433">10.3109/00016347509156433</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/779393">779393</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Obstetricia+Et+Gynecologica+Scandinavica.+Supplement&rft.atitle=The+female+climacteric+syndrome%3A+significance%2C+problems%2C+treatment&rft.volume=51&rft.pages=47-61&rft.date=1976-01&rft_id=info%3Adoi%2F10.3109%2F00016347509156433&rft_id=info%3Apmid%2F779393&rft.aulast=Lauritzen&rft.aufirst=CH&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Lauritzen1975-107"><a href="#cite_ref-Lauritzen1975_107-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLauritzen1975" class="citation journal cs1">Lauritzen C (1975). "The Female Climacteric Syndrome: Significance, Problems, Treatment". Acta Obstetricia et Gynecologica Scandinavica. 54 (s51): 48–61. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3109%2F00016347509156433">10.3109/00016347509156433</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0001-6349">0001-6349</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Obstetricia+et+Gynecologica+Scandinavica&rft.atitle=The+Female+Climacteric+Syndrome%3A+Significance%2C+Problems%2C+Treatment&rft.volume=54&rft.issue=s51&rft.pages=48-61&rft.date=1975&rft_id=info%3Adoi%2F10.3109%2F00016347509156433&rft.issn=0001-6349&rft.aulast=Lauritzen&rft.aufirst=C&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Kopera1991-108"><a href="#cite_ref-Kopera1991_108-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKopera1991" class="citation book cs1">Kopera H (1991). "Hormone der Gonaden". Hormonelle Therapie für die Frau. Kliniktaschenbücher. pp. 59–124. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-3-642-95670-6_6">10.1007/978-3-642-95670-6_6</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-540-54554-5" title="Special:BookSources/978-3-540-54554-5"><bdi>978-3-540-54554-5</bdi></a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0172-777X">0172-777X</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Hormone+der+Gonaden&rft.btitle=Hormonelle+Therapie+f%C3%BCr+die+Frau&rft.series=Kliniktaschenb%C3%BCcher&rft.pages=59-124&rft.date=1991&rft.issn=0172-777X&rft_id=info%3Adoi%2F10.1007%2F978-3-642-95670-6_6&rft.isbn=978-3-540-54554-5&rft.aulast=Kopera&rft.aufirst=H&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid29603164-109"><a href="#cite_ref-pmid29603164_109-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFScottMenonWalsh1980" class="citation journal cs1">Scott WW, Menon M, Walsh PC (April 1980). "Hormonal Therapy of Prostatic Cancer". Cancer. 45 (Suppl 7): 1929–1936. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fcncr.1980.45.s7.1929">10.1002/cncr.1980.45.s7.1929</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/29603164">29603164</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Cancer&rft.atitle=Hormonal+Therapy+of+Prostatic+Cancer&rft.volume=45&rft.issue=Suppl+7&rft.pages=1929-1936&rft.date=1980-04&rft_id=info%3Adoi%2F10.1002%2Fcncr.1980.45.s7.1929&rft_id=info%3Apmid%2F29603164&rft.aulast=Scott&rft.aufirst=WW&rft.au=Menon%2C+M&rft.au=Walsh%2C+PC&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid29756046-110"><a href="#cite_ref-pmid29756046_110-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLeinungFeustelJoseph2018" class="citation journal cs1">Leinung MC, Feustel PJ, Joseph J (2018). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5944393">"Hormonal Treatment of Transgender Women with Oral Estradiol"</a>. Transgender Health. 3 (1): 74–81. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1089%2Ftrgh.2017.0035">10.1089/trgh.2017.0035</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5944393">5944393</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/29756046">29756046</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Transgender+Health&rft.atitle=Hormonal+Treatment+of+Transgender+Women+with+Oral+Estradiol&rft.volume=3&rft.issue=1&rft.pages=74-81&rft.date=2018&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5944393%23id-name%3DPMC&rft_id=info%3Apmid%2F29756046&rft_id=info%3Adoi%2F10.1089%2Ftrgh.2017.0035&rft.aulast=Leinung&rft.aufirst=MC&rft.au=Feustel%2C+PJ&rft.au=Joseph%2C+J&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5944393&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Rydén1950-111"><a href="#cite_ref-Rydén1950_111-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRyden1950" class="citation journal cs1">Ryden AB (1950). "Natural and synthetic oestrogenic substances; their relative effectiveness when administered orally". Acta Endocrinologica. 4 (2): 121–39. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1530%2Facta.0.0040121">10.1530/acta.0.0040121</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/15432047">15432047</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Endocrinologica&rft.atitle=Natural+and+synthetic+oestrogenic+substances%3B+their+relative+effectiveness+when+administered+orally&rft.volume=4&rft.issue=2&rft.pages=121-39&rft.date=1950&rft_id=info%3Adoi%2F10.1530%2Facta.0.0040121&rft_id=info%3Apmid%2F15432047&rft.aulast=Ryden&rft.aufirst=AB&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid14902290-112"><a href="#cite_ref-pmid14902290_112-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRyden1951" class="citation journal cs1">Ryden AB (1951). "The effectiveness of natural and synthetic oestrogenic substances in women". Acta Endocrinologica. 8 (2): 175–91. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1530%2Facta.0.0080175">10.1530/acta.0.0080175</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/14902290">14902290</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Endocrinologica&rft.atitle=The+effectiveness+of+natural+and+synthetic+oestrogenic+substances+in+women&rft.volume=8&rft.issue=2&rft.pages=175-91&rft.date=1951&rft_id=info%3Adoi%2F10.1530%2Facta.0.0080175&rft_id=info%3Apmid%2F14902290&rft.aulast=Ryden&rft.aufirst=AB&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Kottmeier1947-113"><a href="#cite_ref-Kottmeier1947_113-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKottmeier1947" class="citation journal cs1">Kottmeier HL (1947). "Ueber blutungen in der menopause: Speziell der klinischen bedeutung eines endometriums mit zeichen hormonaler beeinflussung: Part I". Acta Obstetricia et Gynecologica Scandinavica. 27 (s6): 1–121. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3109%2F00016344709154486">10.3109/00016344709154486</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0001-6349">0001-6349</a>. <q>There is no doubt that the conversion of the endometrium with injections of both synthetic and native estrogenic hormone preparations succeeds, but the opinion whether native, orally administered preparations can produce a proliferation mucosa changes with different authors. PEDERSEN-BJERGAARD (1939) was able to show that 90% of the folliculin taken up in the blood of the vena portae is inactivated in the liver. Neither KAUFMANN (1933, 1935), RAUSCHER (1939, 1942) nor HERRNBERGER (1941) succeeded in bringing a castration endometrium into proliferation using large doses of orally administered preparations of estrone or estradiol. Other results are reported by NEUSTAEDTER (1939), LAUTERWEIN (1940) and FERIN (1941); they succeeded in converting an atrophic castration endometrium into an unambiguous proliferation mucosa with 120–300 oestradiol or with 380 oestrone.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Obstetricia+et+Gynecologica+Scandinavica&rft.atitle=Ueber+blutungen+in+der+menopause%3A+Speziell+der+klinischen+bedeutung+eines+endometriums+mit+zeichen+hormonaler+beeinflussung%3A+Part+I&rft.volume=27&rft.issue=s6&rft.pages=1-121&rft.date=1947&rft_id=info%3Adoi%2F10.3109%2F00016344709154486&rft.issn=0001-6349&rft.aulast=Kottmeier&rft.aufirst=HL&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-RietbrockStaib2013-114"><a href="#cite_ref-RietbrockStaib2013_114-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRietbrockStaibLoew2013" class="citation book cs1">Rietbrock N, Staib AH, Loew D (11 March 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books-id=FkwEBgAAQBAJ&pg=PA426">Klinische Pharmakologie: Arzneitherapie</a>. Springer-Verlag. pp. 426–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-57636-2" title="Special:BookSources/978-3-642-57636-2"><bdi>978-3-642-57636-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Klinische+Pharmakologie%3A+Arzneitherapie&rft.pages=426-&rft.pub=Springer-Verlag&rft.date=2013-03-11&rft.isbn=978-3-642-57636-2&rft.aulast=Rietbrock&rft.aufirst=N&rft.au=Staib%2C+AH&rft.au=Loew%2C+D&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks-id%3DFkwEBgAAQBAJ%26pg%3DPA426&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Greenblatt1966-115"><a href="#cite_ref-Greenblatt1966_115-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMartinez-ManautouRudel1966" class="citation book cs1">Martinez-Manautou J, Rudel HW (1966). "Antiovulatory Activity of Several Synthetic and Natural Estrogens". In Robert Benjamin Greenblatt (ed.). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=le1qAAAAMAAJ">Ovulation: Stimulation, Suppression, and Detection</a>. Lippincott. pp. 243–253.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Antiovulatory+Activity+of+Several+Synthetic+and+Natural+Estrogens&rft.btitle=Ovulation%3A+Stimulation%2C+Suppression%2C+and+Detection&rft.pages=243-253&rft.pub=Lippincott&rft.date=1966&rft.aulast=Martinez-Manautou&rft.aufirst=J&rft.au=Rudel%2C+HW&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dle1qAAAAMAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-HerrRevesz1970-116"><a href="#cite_ref-HerrRevesz1970_116-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHerrReveszMansonJewell1970" class="citation book cs1">Herr F, Revesz C, Manson AJ, Jewell JB (1970). "Biological Properties of Estrogen Sulfates". Chemical and Biological Aspects of Steroid Conjugation. pp. 368–408. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-3-642-49793-3_8">10.1007/978-3-642-49793-3_8</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-49506-9" title="Special:BookSources/978-3-642-49506-9"><bdi>978-3-642-49506-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Biological+Properties+of+Estrogen+Sulfates&rft.btitle=Chemical+and+Biological+Aspects+of+Steroid+Conjugation&rft.pages=368-408&rft.date=1970&rft_id=info%3Adoi%2F10.1007%2F978-3-642-49793-3_8&rft.isbn=978-3-642-49506-9&rft.aulast=Herr&rft.aufirst=F&rft.au=Revesz%2C+C&rft.au=Manson%2C+AJ&rft.au=Jewell%2C+JB&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid13370006-117"><a href="#cite_ref-pmid13370006_117-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDuncanKistnerMansell1956" class="citation journal cs1">Duncan CJ, Kistner RW, Mansell H (October 1956). <a rel="nofollow" class="external text" href="https://journals.lww.com/greenjournal/citation/1956/10000/suppression_of_ovulation_by_tri_p_anisyl.4.aspx">"Suppression of ovulation by trip-anisyl chloroethylene (TACE)"</a>. Obstetrics and Gynecology. 8 (4): 399–407. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/13370006">13370006</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Obstetrics+and+Gynecology&rft.atitle=Suppression+of+ovulation+by+trip-anisyl+chloroethylene+%28TACE%29&rft.volume=8&rft.issue=4&rft.pages=399-407&rft.date=1956-10&rft_id=info%3Apmid%2F13370006&rft.aulast=Duncan&rft.aufirst=CJ&rft.au=Kistner%2C+RW&rft.au=Mansell%2C+H&rft_id=https%3A%2F%2Fjournals.lww.com%2Fgreenjournal%2Fcitation%2F1956%2F10000%2Fsuppression_of_ovulation_by_tri_p_anisyl.4.aspx&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid4359746-123">^ <a href="#cite_ref-pmid4359746_123-0">a</a> <a href="#cite_ref-pmid4359746_123-1">b</a> <a href="#cite_ref-pmid4359746_123-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFShearerHendrySommervilleFergusson1973" class="citation journal cs1">Shearer RJ, Hendry WF, Sommerville IF, Fergusson JD (December 1973). "Plasma testosterone: an accurate monitor of hormone treatment in prostatic cancer". British Journal of Urology. 45 (6): 668–677. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1464-410x.1973.tb12238.x">10.1111/j.1464-410x.1973.tb12238.x</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/4359746">4359746</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=British+Journal+of+Urology&rft.atitle=Plasma+testosterone%3A+an+accurate+monitor+of+hormone+treatment+in+prostatic+cancer&rft.volume=45&rft.issue=6&rft.pages=668-677&rft.date=1973-12&rft_id=info%3Adoi%2F10.1111%2Fj.1464-410x.1973.tb12238.x&rft_id=info%3Apmid%2F4359746&rft.aulast=Shearer&rft.aufirst=RJ&rft.au=Hendry%2C+WF&rft.au=Sommerville%2C+IF&rft.au=Fergusson%2C+JD&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Ekback2017-124">^ <a href="#cite_ref-Ekback2017_124-0">a</a> <a href="#cite_ref-Ekback2017_124-1">b</a> <a href="#cite_ref-Ekback2017_124-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFEkback2017" class="citation journal cs1">Ekback MP (2017). <a rel="nofollow" class="external text" href="https://www.researchgate.net/publication/321245014">"Hirsutism, What to do?"</a> (PDF). International Journal of Endocrinology and Metabolic Disorders. 3 (3). <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.16966%2F2380-548X.140">10.16966/2380-548X.140</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/2380-548X">2380-548X</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=International+Journal+of+Endocrinology+and+Metabolic+Disorders&rft.atitle=Hirsutism%2C+What+to+do%3F&rft.volume=3&rft.issue=3&rft.date=2017&rft_id=info%3Adoi%2F10.16966%2F2380-548X.140&rft.issn=2380-548X&rft.aulast=Ekback&rft.aufirst=MP&rft_id=https%3A%2F%2Fwww.researchgate.net%2Fpublication%2F321245014&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-NieschlagBehre2012-125">^ <a href="#cite_ref-NieschlagBehre2012_125-0">a</a> <a href="#cite_ref-NieschlagBehre2012_125-1">b</a> <a href="#cite_ref-NieschlagBehre2012_125-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNieschlagBehreNieschlag2012" class="citation book cs1">Nieschlag E, Behre HM, Nieschlag S (26 July 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=MkrAPaQ4wJkC&pg=PA62">Testosterone: Action, Deficiency, Substitution</a>. Cambridge University Press. pp. 62–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-107-01290-5" title="Special:BookSources/978-1-107-01290-5"><bdi>978-1-107-01290-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Testosterone%3A+Action%2C+Deficiency%2C+Substitution&rft.pages=62-&rft.pub=Cambridge+University+Press&rft.date=2012-07-26&rft.isbn=978-1-107-01290-5&rft.aulast=Nieschlag&rft.aufirst=E&rft.au=Behre%2C+HM&rft.au=Nieschlag%2C+S&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DMkrAPaQ4wJkC%26pg%3DPA62&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid22294742-126"><a href="#cite_ref-pmid22294742_126-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCossJonesParkeNarayanan2012" class="citation journal cs1">Coss CC, Jones A, Parke DN, Narayanan R, Barrett CM, Kearbey JD, et al. (March 2012). <a rel="nofollow" class="external text" href="https://doi.org/10.1210%2Fen.2011-1608">"Preclinical characterization of a novel diphenyl benzamide selective ERα agonist for hormone therapy in prostate cancer"</a>. Endocrinology. 153 (3): 1070–1081. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1210%2Fen.2011-1608">10.1210/en.2011-1608</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/22294742">22294742</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Endocrinology&rft.atitle=Preclinical+characterization+of+a+novel+diphenyl+benzamide+selective+ER%CE%B1+agonist+for+hormone+therapy+in+prostate+cancer&rft.volume=153&rft.issue=3&rft.pages=1070-1081&rft.date=2012-03&rft_id=info%3Adoi%2F10.1210%2Fen.2011-1608&rft_id=info%3Apmid%2F22294742&rft.aulast=Coss&rft.aufirst=CC&rft.au=Jones%2C+A&rft.au=Parke%2C+DN&rft.au=Narayanan%2C+R&rft.au=Barrett%2C+CM&rft.au=Kearbey%2C+JD&rft.au=Veverka%2C+KA&rft.au=Miller%2C+DD&rft.au=Morton%2C+RA&rft.au=Steiner%2C+MS&rft.au=Dalton%2C+JT&rft_id=https%3A%2F%2Fdoi.org%2F10.1210%252Fen.2011-1608&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid18338653-127"><a href="#cite_ref-pmid18338653_127-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRich2008" class="citation journal cs1">Rich P (January 2008). "Hormonal contraceptives for acne management". Cutis. 81 (1 Suppl): 13–18. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/18338653">18338653</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Cutis&rft.atitle=Hormonal+contraceptives+for+acne+management&rft.volume=81&rft.issue=1+Suppl&rft.pages=13-18&rft.date=2008-01&rft_id=info%3Apmid%2F18338653&rft.aulast=Rich&rft.aufirst=P&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid24082040-128"><a href="#cite_ref-pmid24082040_128-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFZimmermanEijkemansCoelingh_BenninkBlankenstein2014" class="citation journal cs1">Zimmerman Y, Eijkemans MJ, Coelingh Bennink HJ, Blankenstein MA, Fauser BC (2014). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3845679">"The effect of combined oral contraception on testosterone levels in healthy women: a systematic review and meta-analysis"</a>. Hum Reprod Update. 20 (1): 76–105. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fhumupd%2Fdmt038">10.1093/humupd/dmt038</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3845679">3845679</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/24082040">24082040</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Hum+Reprod+Update&rft.atitle=The+effect+of+combined+oral+contraception+on+testosterone+levels+in+healthy+women%3A+a+systematic+review+and+meta-analysis&rft.volume=20&rft.issue=1&rft.pages=76-105&rft.date=2014&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3845679%23id-name%3DPMC&rft_id=info%3Apmid%2F24082040&rft_id=info%3Adoi%2F10.1093%2Fhumupd%2Fdmt038&rft.aulast=Zimmerman&rft.aufirst=Y&rft.au=Eijkemans%2C+MJ&rft.au=Coelingh+Bennink%2C+HJ&rft.au=Blankenstein%2C+MA&rft.au=Fauser%2C+BC&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3845679&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid37419659-129"><a href="#cite_ref-pmid37419659_129-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFÖzcanden_ElzenHillebrandden_Heijer2024" class="citation journal cs1">Özcan Ö, den Elzen WP, Hillebrand JJ, den Heijer M, van Loendersloot LL, Fischer J, et al. (January 2024). <a rel="nofollow" class="external text" href="https://doi.org/10.1515%2Fcclm-2023-0384">"The effect of hormonal contraceptive therapy on clinical laboratory parameters: a literature review"</a>. Clin Chem Lab Med. 62 (1): 18–40. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1515%2Fcclm-2023-0384">10.1515/cclm-2023-0384</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/37419659">37419659</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:259361637">259361637</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Clin+Chem+Lab+Med&rft.atitle=The+effect+of+hormonal+contraceptive+therapy+on+clinical+laboratory+parameters%3A+a+literature+review&rft.volume=62&rft.issue=1&rft.pages=18-40&rft.date=2024-01&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A259361637%23id-name%3DS2CID&rft_id=info%3Apmid%2F37419659&rft_id=info%3Adoi%2F10.1515%2Fcclm-2023-0384&rft.aulast=%C3%96zcan&rft.aufirst=%C3%96&rft.au=den+Elzen%2C+WP&rft.au=Hillebrand%2C+JJ&rft.au=den+Heijer%2C+M&rft.au=van+Loendersloot%2C+LL&rft.au=Fischer%2C+J&rft.au=Hamer%2C+H&rft.au=de+Jonge%2C+R&rft.au=Heijboer%2C+AC&rft_id=https%3A%2F%2Fdoi.org%2F10.1515%252Fcclm-2023-0384&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid22950535-130"><a href="#cite_ref-pmid22950535_130-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFYangPlosker2012" class="citation journal cs1">Yang LP, Plosker GL (October 2012). "Nomegestrol acetate/estradiol: in oral contraception". Drugs. 72 (14): 1917–1928. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.2165%2F11208180-000000000-00000">10.2165/11208180-000000000-00000</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/22950535">22950535</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:44335732">44335732</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Drugs&rft.atitle=Nomegestrol+acetate%2Festradiol%3A+in+oral+contraception&rft.volume=72&rft.issue=14&rft.pages=1917-1928&rft.date=2012-10&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A44335732%23id-name%3DS2CID&rft_id=info%3Apmid%2F22950535&rft_id=info%3Adoi%2F10.2165%2F11208180-000000000-00000&rft.aulast=Yang&rft.aufirst=LP&rft.au=Plosker%2C+GL&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid7000222-131">^ <a href="#cite_ref-pmid7000222_131-0">a</a> <a href="#cite_ref-pmid7000222_131-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJacobiAltweinKurthBasting1980" class="citation journal cs1">Jacobi GH, Altwein JE, Kurth KH, Basting R, Hohenfellner R (June 1980). "Treatment of advanced prostatic cancer with parenteral cyproterone acetate: a phase III randomised trial". British Journal of Urology. 52 (3): 208–215. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1464-410x.1980.tb02961.x">10.1111/j.1464-410x.1980.tb02961.x</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/7000222">7000222</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=British+Journal+of+Urology&rft.atitle=Treatment+of+advanced+prostatic+cancer+with+parenteral+cyproterone+acetate%3A+a+phase+III+randomised+trial&rft.volume=52&rft.issue=3&rft.pages=208-215&rft.date=1980-06&rft_id=info%3Adoi%2F10.1111%2Fj.1464-410x.1980.tb02961.x&rft_id=info%3Apmid%2F7000222&rft.aulast=Jacobi&rft.aufirst=GH&rft.au=Altwein%2C+JE&rft.au=Kurth%2C+KH&rft.au=Basting%2C+R&rft.au=Hohenfellner%2C+R&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid3217277-132">^ <a href="#cite_ref-pmid3217277_132-0">a</a> <a href="#cite_ref-pmid3217277_132-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGunnarssonNorlén1988" class="citation journal cs1">Gunnarsson PO, Norlén BJ (1988). "Clinical pharmacology of polyestradiol phosphate". The Prostate. 13 (4): 299–304. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fpros.2990130405">10.1002/pros.2990130405</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/3217277">3217277</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:33063805">33063805</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Prostate&rft.atitle=Clinical+pharmacology+of+polyestradiol+phosphate&rft.volume=13&rft.issue=4&rft.pages=299-304&rft.date=1988&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A33063805%23id-name%3DS2CID&rft_id=info%3Apmid%2F3217277&rft_id=info%3Adoi%2F10.1002%2Fpros.2990130405&rft.aulast=Gunnarsson&rft.aufirst=PO&rft.au=Norl%C3%A9n%2C+BJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid2630306-133"><a href="#cite_ref-pmid2630306_133-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFStahlSchnorrBärFröhlich1989" class="citation journal cs1">Stahl F, Schnorr D, Bär CM, Fröhlich G, Dörner G (1989). "Suppression of plasma androgen levels with a combination therapy of depot-estrogen (Turisteron) and Dexamethasone in patients with prostatic cancer". Experimental and Clinical Endocrinology. 94 (3): 239–243. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1055%2Fs-0029-1210905">10.1055/s-0029-1210905</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/2630306">2630306</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:40497389">40497389</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Experimental+and+Clinical+Endocrinology&rft.atitle=Suppression+of+plasma+androgen+levels+with+a+combination+therapy+of+depot-estrogen+%28Turisteron%29+and+Dexamethasone+in+patients+with+prostatic+cancer&rft.volume=94&rft.issue=3&rft.pages=239-243&rft.date=1989&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A40497389%23id-name%3DS2CID&rft_id=info%3Apmid%2F2630306&rft_id=info%3Adoi%2F10.1055%2Fs-0029-1210905&rft.aulast=Stahl&rft.aufirst=F&rft.au=Schnorr%2C+D&rft.au=B%C3%A4r%2C+CM&rft.au=Fr%C3%B6hlich%2C+G&rft.au=D%C3%B6rner%2C+G&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-JamesonGroot2010-134">^ <a href="#cite_ref-JamesonGroot2010_134-0">a</a> <a href="#cite_ref-JamesonGroot2010_134-1">b</a> <a href="#cite_ref-JamesonGroot2010_134-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJamesonDe_Groot2010" class="citation book cs1">Jameson JL, De Groot LJ (18 May 2010). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=W4dZ-URK8ZoC&pg=PA2282">Endocrinology - E-Book: Adult and Pediatric</a>. Elsevier Health Sciences. pp. 2282–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4557-1126-0" title="Special:BookSources/978-1-4557-1126-0"><bdi>978-1-4557-1126-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Endocrinology+-+E-Book%3A+Adult+and+Pediatric&rft.pages=2282-&rft.pub=Elsevier+Health+Sciences&rft.date=2010-05-18&rft.isbn=978-1-4557-1126-0&rft.aulast=Jameson&rft.aufirst=JL&rft.au=De+Groot%2C+LJ&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DW4dZ-URK8ZoC%26pg%3DPA2282&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-DenisGriffiths1999-135"><a href="#cite_ref-DenisGriffiths1999_135-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDenisGriffithsKaisaryMurphy1999" class="citation book cs1">Denis LJ, Griffiths K, Kaisary AV, Murphy GP (1 March 1999). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=GreZlojD-tYC&pg=PA297">Textbook of Prostate Cancer: Pathology, Diagnosis and Treatment: Pathology, Diagnosis and Treatment</a>. CRC Press. pp. 297–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-85317-422-3" title="Special:BookSources/978-1-85317-422-3"><bdi>978-1-85317-422-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Textbook+of+Prostate+Cancer%3A+Pathology%2C+Diagnosis+and+Treatment%3A+Pathology%2C+Diagnosis+and+Treatment&rft.pages=297-&rft.pub=CRC+Press&rft.date=1999-03-01&rft.isbn=978-1-85317-422-3&rft.aulast=Denis&rft.aufirst=LJ&rft.au=Griffiths%2C+K&rft.au=Kaisary%2C+AV&rft.au=Murphy%2C+GP&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DGreZlojD-tYC%26pg%3DPA297&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid29603164b-136"><a href="#cite_ref-pmid29603164b_136-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFScottMenonWalsh1980" class="citation journal cs1">Scott WW, Menon M, Walsh PC (April 1980). <a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fcncr.1980.45.s7.1929">"Hormonal Therapy of Prostatic Cancer"</a>. Cancer. 45 (Suppl 7): 1929–1936. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fcncr.1980.45.s7.1929">10.1002/cncr.1980.45.s7.1929</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/29603164">29603164</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:4492779">4492779</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Cancer&rft.atitle=Hormonal+Therapy+of+Prostatic+Cancer&rft.volume=45&rft.issue=Suppl+7&rft.pages=1929-1936&rft.date=1980-04&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A4492779%23id-name%3DS2CID&rft_id=info%3Apmid%2F29603164&rft_id=info%3Adoi%2F10.1002%2Fcncr.1980.45.s7.1929&rft.aulast=Scott&rft.aufirst=WW&rft.au=Menon%2C+M&rft.au=Walsh%2C+PC&rft_id=https%3A%2F%2Fdoi.org%2F10.1002%252Fcncr.1980.45.s7.1929&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid4568621-137"><a href="#cite_ref-pmid4568621_137-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBingelBenoit1973" class="citation journal cs1">Bingel AS, Benoit PS (February 1973). "Oral contraceptives: therapeutics versus adverse reactions, with an outlook for the future I". Journal of Pharmaceutical Sciences. 62 (2): 179–200. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fjps.2600620202">10.1002/jps.2600620202</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/4568621">4568621</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Pharmaceutical+Sciences&rft.atitle=Oral+contraceptives%3A+therapeutics+versus+adverse+reactions%2C+with+an+outlook+for+the+future+I&rft.volume=62&rft.issue=2&rft.pages=179-200&rft.date=1973-02&rft_id=info%3Adoi%2F10.1002%2Fjps.2600620202&rft_id=info%3Apmid%2F4568621&rft.aulast=Bingel&rft.aufirst=AS&rft.au=Benoit%2C+PS&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-RietbrockStaib2013b-138"><a href="#cite_ref-RietbrockStaib2013b_138-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRietbrockStaibLoew2013" class="citation book cs1">Rietbrock N, Staib AH, Loew D (11 March 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=FkwEBgAAQBAJ&pg=PA426">Klinische Pharmakologie: Arzneitherapie</a>. Springer-Verlag. pp. 426–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-57636-2" title="Special:BookSources/978-3-642-57636-2"><bdi>978-3-642-57636-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Klinische+Pharmakologie%3A+Arzneitherapie&rft.pages=426-&rft.pub=Springer-Verlag&rft.date=2013-03-11&rft.isbn=978-3-642-57636-2&rft.aulast=Rietbrock&rft.aufirst=N&rft.au=Staib%2C+AH&rft.au=Loew%2C+D&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DFkwEBgAAQBAJ%26pg%3DPA426&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Elger1972-139"><a href="#cite_ref-Elger1972_139-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFElger1972" class="citation book cs1">Elger W (1972). "Physiology and pharmacology of female reproduction under the aspect of fertility control". Reviews of Physiology Biochemistry and Experimental Pharmacology, Volume 67. Ergebnisse der Physiologie Reviews of Physiology. Vol. 67. pp. 69–168. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2FBFb0036328">10.1007/BFb0036328</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/3-540-05959-8" title="Special:BookSources/3-540-05959-8"><bdi>3-540-05959-8</bdi></a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/4574573">4574573</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Physiology+and+pharmacology+of+female+reproduction+under+the+aspect+of+fertility+control&rft.btitle=Reviews+of+Physiology+Biochemistry+and+Experimental+Pharmacology%2C+Volume+67&rft.series=Ergebnisse+der+Physiologie+Reviews+of+Physiology&rft.pages=69-168&rft.date=1972&rft_id=info%3Apmid%2F4574573&rft_id=info%3Adoi%2F10.1007%2FBFb0036328&rft.isbn=3-540-05959-8&rft.aulast=Elger&rft.aufirst=W&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-BastianelliFarris2018-140"><a href="#cite_ref-BastianelliFarris2018_140-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBastianelliFarrisRosatoBrosens2018" class="citation journal cs1">Bastianelli C, Farris M, Rosato E, Brosens I, Benagiano G (November 2018). "Pharmacodynamics of combined estrogen-progestin oral contraceptives 3. Inhibition of ovulation". Expert Review of Clinical Pharmacology. 11 (11): 1085–1098. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F17512433.2018.1536544">10.1080/17512433.2018.1536544</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/30325245">30325245</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:53246678">53246678</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Expert+Review+of+Clinical+Pharmacology&rft.atitle=Pharmacodynamics+of+combined+estrogen-progestin+oral+contraceptives+3.+Inhibition+of+ovulation&rft.volume=11&rft.issue=11&rft.pages=1085-1098&rft.date=2018-11&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A53246678%23id-name%3DS2CID&rft_id=info%3Apmid%2F30325245&rft_id=info%3Adoi%2F10.1080%2F17512433.2018.1536544&rft.aulast=Bastianelli&rft.aufirst=C&rft.au=Farris%2C+M&rft.au=Rosato%2C+E&rft.au=Brosens%2C+I&rft.au=Benagiano%2C+G&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Greenblatt1966b-141"><a href="#cite_ref-Greenblatt1966b_141-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMartinez-ManautouRudel1966" class="citation book cs1">Martinez-Manautou J, Rudel HW (1966). "Antiovulatory Activity of Several Synthetic and Natural Estrogens". In Greenblatt RB (ed.). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=le1qAAAAMAAJ">Ovulation: Stimulation, Suppression, and Detection</a>. Lippincott. pp. 243–253. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-397-59010-0" title="Special:BookSources/978-0-397-59010-0"><bdi>978-0-397-59010-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Antiovulatory+Activity+of+Several+Synthetic+and+Natural+Estrogens&rft.btitle=Ovulation%3A+Stimulation%2C+Suppression%2C+and+Detection&rft.pages=243-253&rft.pub=Lippincott&rft.date=1966&rft.isbn=978-0-397-59010-0&rft.aulast=Martinez-Manautou&rft.aufirst=J&rft.au=Rudel%2C+HW&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dle1qAAAAMAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-HerrRevesz1970k-142"><a href="#cite_ref-HerrRevesz1970k_142-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHerrReveszMansonJewell1970" class="citation book cs1">Herr F, Revesz C, Manson AJ, Jewell JB (1970). "Biological Properties of Estrogen Sulfates". Chemical and Biological Aspects of Steroid Conjugation. pp. 368–408. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-3-642-49793-3_8">10.1007/978-3-642-49793-3_8</a> (inactive 1 November 2024). <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-49506-9" title="Special:BookSources/978-3-642-49506-9"><bdi>978-3-642-49506-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Biological+Properties+of+Estrogen+Sulfates&rft.btitle=Chemical+and+Biological+Aspects+of+Steroid+Conjugation&rft.pages=368-408&rft.date=1970&rft_id=info%3Adoi%2F10.1007%2F978-3-642-49793-3_8&rft.isbn=978-3-642-49506-9&rft.aulast=Herr&rft.aufirst=F&rft.au=Revesz%2C+C&rft.au=Manson%2C+AJ&rft.au=Jewell%2C+JB&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"><code class="cs1-code">{{<a href="/wiki/Template:Cite_book" title="Template:Cite book">cite book</a>}}</code>: CS1 maint: DOI inactive as of November 2024 (<a href="/wiki/Category:CS1_maint:_DOI_inactive_as_of_November_2024" title="Category:CS1 maint: DOI inactive as of November 2024">link</a>) </li> <li id="cite_note-pmid1146927-143"><a href="#cite_ref-pmid1146927_143-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGoldzieherPenaChenaultWoutersz1975" class="citation journal cs1">Goldzieher JW, Pena A, Chenault CB, Woutersz TB (July 1975). "Comparative studies of the ethynyl estrogens used in oral contraceptives. II. Antiovulatory potency". American Journal of Obstetrics and Gynecology. 122 (5): 619–624. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0002-9378%2875%2990061-7">10.1016/0002-9378(75)90061-7</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/1146927">1146927</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=American+Journal+of+Obstetrics+and+Gynecology&rft.atitle=Comparative+studies+of+the+ethynyl+estrogens+used+in+oral+contraceptives.+II.+Antiovulatory+potency&rft.volume=122&rft.issue=5&rft.pages=619-624&rft.date=1975-07&rft_id=info%3Adoi%2F10.1016%2F0002-9378%2875%2990061-7&rft_id=info%3Apmid%2F1146927&rft.aulast=Goldzieher&rft.aufirst=JW&rft.au=Pena%2C+A&rft.au=Chenault%2C+CB&rft.au=Woutersz%2C+TB&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-MargiorisChrousos2001-144">^ <a href="#cite_ref-MargiorisChrousos2001_144-0">a</a> <a href="#cite_ref-MargiorisChrousos2001_144-1">b</a> <a href="#cite_ref-MargiorisChrousos2001_144-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMargiorisChrousos2001" class="citation book cs1">Margioris AN, Chrousos GP (20 April 2001). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=XB73BwAAQBAJ&pg=PA84">Adrenal Disorders</a>. Springer Science & Business Media. pp. 84–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-59259-101-5" title="Special:BookSources/978-1-59259-101-5"><bdi>978-1-59259-101-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Adrenal+Disorders&rft.pages=84-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2001-04-20&rft.isbn=978-1-59259-101-5&rft.aulast=Margioris&rft.aufirst=AN&rft.au=Chrousos%2C+GP&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DXB73BwAAQBAJ%26pg%3DPA84&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid7586614-145">^ <a href="#cite_ref-pmid7586614_145-0">a</a> <a href="#cite_ref-pmid7586614_145-1">b</a> <a href="#cite_ref-pmid7586614_145-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPoldermanGoorenvan_der_Veen1995" class="citation journal cs1">Polderman KH, Gooren LJ, van der Veen EA (October 1995). "Effects of gonadal androgens and oestrogens on adrenal androgen levels". Clinical Endocrinology. 43 (4): 415–421. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1365-2265.1995.tb02611.x">10.1111/j.1365-2265.1995.tb02611.x</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/7586614">7586614</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:6815423">6815423</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Clinical+Endocrinology&rft.atitle=Effects+of+gonadal+androgens+and+oestrogens+on+adrenal+androgen+levels&rft.volume=43&rft.issue=4&rft.pages=415-421&rft.date=1995-10&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A6815423%23id-name%3DS2CID&rft_id=info%3Apmid%2F7586614&rft_id=info%3Adoi%2F10.1111%2Fj.1365-2265.1995.tb02611.x&rft.aulast=Polderman&rft.aufirst=KH&rft.au=Gooren%2C+LJ&rft.au=van+der+Veen%2C+EA&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid22244780-146"><a href="#cite_ref-pmid22244780_146-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTrémollieres2012" class="citation journal cs1 cs1-prop-foreign-lang-source">Trémollieres F (February 2012). "[Oral combined contraception: is there any difference between ethinyl-estradiol and estradiol?]" [Oral combined contraception: is there any difference between ethinyl-estradiol and estradiol?]. Gynécologie, Obstétrique & Fertilité (in French). 40 (2): 109–115. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.gyobfe.2011.10.009">10.1016/j.gyobfe.2011.10.009</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/22244780">22244780</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Gyn%C3%A9cologie%2C+Obst%C3%A9trique+%26+Fertilit%C3%A9&rft.atitle=%5BOral+combined+contraception%3A+is+there+any+difference+between+ethinyl-estradiol+and+estradiol%3F%5D&rft.volume=40&rft.issue=2&rft.pages=109-115&rft.date=2012-02&rft_id=info%3Adoi%2F10.1016%2Fj.gyobfe.2011.10.009&rft_id=info%3Apmid%2F22244780&rft.aulast=Tr%C3%A9mollieres&rft.aufirst=F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Lobo2007-147">^ <a href="#cite_ref-Lobo2007_147-0">a</a> <a href="#cite_ref-Lobo2007_147-1">b</a> <a href="#cite_ref-Lobo2007_147-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLobo2007" class="citation book cs1">Lobo RA (5 June 2007). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=gywV9hkcyOMC&pg=PA770">Treatment of the Postmenopausal Woman: Basic and Clinical Aspects</a>. Academic Press. pp. 177, 770–771. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-08-055309-2" title="Special:BookSources/978-0-08-055309-2"><bdi>978-0-08-055309-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Treatment+of+the+Postmenopausal+Woman%3A+Basic+and+Clinical+Aspects&rft.pages=177%2C+770-771&rft.pub=Academic+Press&rft.date=2007-06-05&rft.isbn=978-0-08-055309-2&rft.aulast=Lobo&rft.aufirst=RA&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DgywV9hkcyOMC%26pg%3DPA770&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Shoupe2011-148"><a href="#cite_ref-Shoupe2011_148-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFShoupe2011" class="citation book cs1">Shoupe D (10 February 2011). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=ksjJcx1CeKcC&pg=PA79">Contraception</a>. John Wiley & Sons. pp. 79–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4443-4263-5" title="Special:BookSources/978-1-4443-4263-5"><bdi>978-1-4443-4263-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Contraception&rft.pages=79-&rft.pub=John+Wiley+%26+Sons&rft.date=2011-02-10&rft.isbn=978-1-4443-4263-5&rft.aulast=Shoupe&rft.aufirst=D&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DksjJcx1CeKcC%26pg%3DPA79&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid21538049-149"><a href="#cite_ref-pmid21538049_149-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSitruk-WareNath2011" class="citation journal cs1">Sitruk-Ware R, Nath A (June 2011). "Metabolic effects of contraceptive steroids". Reviews in Endocrine & Metabolic Disorders. 12 (2): 63–75. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs11154-011-9182-4">10.1007/s11154-011-9182-4</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/21538049">21538049</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:23760705">23760705</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Reviews+in+Endocrine+%26+Metabolic+Disorders&rft.atitle=Metabolic+effects+of+contraceptive+steroids&rft.volume=12&rft.issue=2&rft.pages=63-75&rft.date=2011-06&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A23760705%23id-name%3DS2CID&rft_id=info%3Apmid%2F21538049&rft_id=info%3Adoi%2F10.1007%2Fs11154-011-9182-4&rft.aulast=Sitruk-Ware&rft.aufirst=R&rft.au=Nath%2C+A&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid12520628-150">^ <a href="#cite_ref-pmid12520628_150-0">a</a> <a href="#cite_ref-pmid12520628_150-1">b</a> <a href="#cite_ref-pmid12520628_150-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBoydZegaracEldon2003" class="citation journal cs1">Boyd RA, Zegarac EA, Eldon MA (January 2003). "The effect of food on the bioavailability of norethindrone and ethinyl estradiol from norethindrone acetate/ethinyl estradiol tablets intended for continuous hormone replacement therapy". Journal of Clinical Pharmacology. 43 (1): 52–58. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1177%2F0091270002239706">10.1177/0091270002239706</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/12520628">12520628</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:27729272">27729272</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Clinical+Pharmacology&rft.atitle=The+effect+of+food+on+the+bioavailability+of+norethindrone+and+ethinyl+estradiol+from+norethindrone+acetate%2Fethinyl+estradiol+tablets+intended+for+continuous+hormone+replacement+therapy&rft.volume=43&rft.issue=1&rft.pages=52-58&rft.date=2003-01&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A27729272%23id-name%3DS2CID&rft_id=info%3Apmid%2F12520628&rft_id=info%3Adoi%2F10.1177%2F0091270002239706&rft.aulast=Boyd&rft.aufirst=RA&rft.au=Zegarac%2C+EA&rft.au=Eldon%2C+MA&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-DodickSilberstein2016-151">^ <a href="#cite_ref-DodickSilberstein2016_151-0">a</a> <a href="#cite_ref-DodickSilberstein2016_151-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDodickSilberstein2016" class="citation book cs1">Dodick D, Silberstein SD (2016). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=Y-wmDAAAQBAJ&pg=PA272">Migraine</a>. Oxford University Press. pp. 272–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-19-979361-7" title="Special:BookSources/978-0-19-979361-7"><bdi>978-0-19-979361-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Migraine&rft.pages=272-&rft.pub=Oxford+University+Press&rft.date=2016&rft.isbn=978-0-19-979361-7&rft.aulast=Dodick&rft.aufirst=D&rft.au=Silberstein%2C+SD&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DY-wmDAAAQBAJ%26pg%3DPA272&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid6342899-152">^ <a href="#cite_ref-pmid6342899_152-0">a</a> <a href="#cite_ref-pmid6342899_152-1">b</a> <a href="#cite_ref-pmid6342899_152-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFOrmeBackBreckenridge1983" class="citation journal cs1">Orme ML, Back DJ, Breckenridge AM (1983). "Clinical pharmacokinetics of oral contraceptive steroids". Clinical Pharmacokinetics. 8 (2): 95–136. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.2165%2F00003088-198308020-00001">10.2165/00003088-198308020-00001</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/6342899">6342899</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:43298472">43298472</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Clinical+Pharmacokinetics&rft.atitle=Clinical+pharmacokinetics+of+oral+contraceptive+steroids&rft.volume=8&rft.issue=2&rft.pages=95-136&rft.date=1983&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A43298472%23id-name%3DS2CID&rft_id=info%3Apmid%2F6342899&rft_id=info%3Adoi%2F10.2165%2F00003088-198308020-00001&rft.aulast=Orme&rft.aufirst=ML&rft.au=Back%2C+DJ&rft.au=Breckenridge%2C+AM&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-NotelovitzKeep2012-153">^ <a href="#cite_ref-NotelovitzKeep2012_153-0">a</a> <a href="#cite_ref-NotelovitzKeep2012_153-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNotelovitzvan_Keep2012" class="citation book cs1">Notelovitz M, van Keep PA (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=VM0hBQAAQBAJ&pg=PA395">The Climacteric in Perspective: Proceedings of the Fourth International Congress on the Menopause, held at Lake Buena Vista, Florida, October 28–November 2, 1984</a>. Springer Science & Business Media. pp. 395–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-94-009-4145-8" title="Special:BookSources/978-94-009-4145-8"><bdi>978-94-009-4145-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Climacteric+in+Perspective%3A+Proceedings+of+the+Fourth+International+Congress+on+the+Menopause%2C+held+at+Lake+Buena+Vista%2C+Florida%2C+October+28%E2%80%93November+2%2C+1984&rft.pages=395-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-94-009-4145-8&rft.aulast=Notelovitz&rft.aufirst=M&rft.au=van+Keep%2C+PA&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DVM0hBQAAQBAJ%26pg%3DPA395&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid7195405-154"><a href="#cite_ref-pmid7195405_154-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPugeatDunnNisula1981" class="citation journal cs1">Pugeat MM, Dunn JF, Nisula BC (July 1981). "Transport of steroid hormones: interaction of 70 drugs with testosterone-binding globulin and corticosteroid-binding globulin in human plasma". The Journal of Clinical Endocrinology and Metabolism. 53 (1): 69–75. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1210%2Fjcem-53-1-69">10.1210/jcem-53-1-69</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/7195405">7195405</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Clinical+Endocrinology+and+Metabolism&rft.atitle=Transport+of+steroid+hormones%3A+interaction+of+70+drugs+with+testosterone-binding+globulin+and+corticosteroid-binding+globulin+in+human+plasma&rft.volume=53&rft.issue=1&rft.pages=69-75&rft.date=1981-07&rft_id=info%3Adoi%2F10.1210%2Fjcem-53-1-69&rft_id=info%3Apmid%2F7195405&rft.aulast=Pugeat&rft.aufirst=MM&rft.au=Dunn%2C+JF&rft.au=Nisula%2C+BC&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid30809949-155"><a href="#cite_ref-pmid30809949_155-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBackeljauwKlein2019" class="citation journal cs1">Backeljauw P, Klein K (March 2019). "Sex hormone replacement therapy for individuals with Turner syndrome". American Journal of Medical Genetics. Part C, Seminars in Medical Genetics. 181 (1): 13–17. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fajmg.c.31685">10.1002/ajmg.c.31685</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/30809949">30809949</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:73487051">73487051</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=American+Journal+of+Medical+Genetics.+Part+C%2C+Seminars+in+Medical+Genetics&rft.atitle=Sex+hormone+replacement+therapy+for+individuals+with+Turner+syndrome&rft.volume=181&rft.issue=1&rft.pages=13-17&rft.date=2019-03&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A73487051%23id-name%3DS2CID&rft_id=info%3Apmid%2F30809949&rft_id=info%3Adoi%2F10.1002%2Fajmg.c.31685&rft.aulast=Backeljauw&rft.aufirst=P&rft.au=Klein%2C+K&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid25099693-156">^ <a href="#cite_ref-pmid25099693_156-0">a</a> <a href="#cite_ref-pmid25099693_156-1">b</a> <a href="#cite_ref-pmid25099693_156-2">c</a> <a href="#cite_ref-pmid25099693_156-3">d</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMattisonKaryakinaGoodmanLaKind2014" class="citation journal cs1">Mattison DR, Karyakina N, Goodman M, LaKind JS (September 2014). "Pharmaco- and toxicokinetics of selected exogenous and endogenous estrogens: a review of the data and identification of knowledge gaps". Critical Reviews in Toxicology. 44 (8): 696–724. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3109%2F10408444.2014.930813">10.3109/10408444.2014.930813</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/25099693">25099693</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:11212469">11212469</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Critical+Reviews+in+Toxicology&rft.atitle=Pharmaco-+and+toxicokinetics+of+selected+exogenous+and+endogenous+estrogens%3A+a+review+of+the+data+and+identification+of+knowledge+gaps&rft.volume=44&rft.issue=8&rft.pages=696-724&rft.date=2014-09&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A11212469%23id-name%3DS2CID&rft_id=info%3Apmid%2F25099693&rft_id=info%3Adoi%2F10.3109%2F10408444.2014.930813&rft.aulast=Mattison&rft.aufirst=DR&rft.au=Karyakina%2C+N&rft.au=Goodman%2C+M&rft.au=LaKind%2C+JS&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-IndexNominum2000-157">^ <a href="#cite_ref-IndexNominum2000_157-0">a</a> <a href="#cite_ref-IndexNominum2000_157-1">b</a> <a href="#cite_ref-IndexNominum2000_157-2">c</a> <a href="#cite_ref-IndexNominum2000_157-3">d</a> <a href="#cite_ref-IndexNominum2000_157-4">e</a> <a href="#cite_ref-IndexNominum2000_157-5">f</a> <a href="#cite_ref-IndexNominum2000_157-6">g</a> <a href="#cite_ref-IndexNominum2000_157-7">h</a> <a href="#cite_ref-IndexNominum2000_157-8">i</a> <a href="#cite_ref-IndexNominum2000_157-9">j</a> <a href="#cite_ref-IndexNominum2000_157-10">k</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1"><a rel="nofollow" class="external text" href="https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA1321">Index Nominum 2000: International Drug Directory</a>. Taylor & Francis. January 2000. p. 412. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-88763-075-1" title="Special:BookSources/978-3-88763-075-1"><bdi>978-3-88763-075-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Index+Nominum+2000%3A+International+Drug+Directory&rft.pages=412&rft.pub=Taylor+%26+Francis&rft.date=2000-01&rft.isbn=978-3-88763-075-1&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D5GpcTQD_L2oC%26pg%3DPA1321&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Inhoffen_1938-158"><a href="#cite_ref-Inhoffen_1938_158-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFInhoffenHohlweg1938" class="citation journal cs1">Inhoffen HH, Hohlweg W (1938). "Neue per os-wirksame weibliche Keimdrüsenhormon-Derivate: 17-Aethinyl-oestradiol und Pregnen-in-on-3-ol-17 (New female glandular derivatives active per os: 17α-ethynyl-estradiol and pregnen-in-on-3-ol-17)". <a href="/wiki/Die_Naturwissenschaften" class="mw-redirect" title="Die Naturwissenschaften">Naturwissenschaften</a>. 26 (6): 96. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1938NW.....26...96I">1938NW.....26...96I</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2FBF01681040">10.1007/BF01681040</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:46648877">46648877</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Naturwissenschaften&rft.atitle=Neue+per+os-wirksame+weibliche+Keimdr%C3%BCsenhormon-Derivate%3A+17-Aethinyl-oestradiol+und+Pregnen-in-on-3-ol-17+%28New+female+glandular+derivatives+active+per+os%3A+17%CE%B1-ethynyl-estradiol+and+pregnen-in-on-3-ol-17%29&rft.volume=26&rft.issue=6&rft.pages=96&rft.date=1938&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A46648877%23id-name%3DS2CID&rft_id=info%3Adoi%2F10.1007%2FBF01681040&rft_id=info%3Abibcode%2F1938NW.....26...96I&rft.aulast=Inhoffen&rft.aufirst=HH&rft.au=Hohlweg%2C+W&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Maisel_1965-159"><a href="#cite_ref-Maisel_1965_159-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMaisel1965" class="citation book cs1">Maisel AQ (1965). The Hormone Quest. New York: Random House. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/543168">543168</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Hormone+Quest&rft.place=New+York&rft.pub=Random+House&rft.date=1965&rft_id=info%3Aoclcnum%2F543168&rft.aulast=Maisel&rft.aufirst=AQ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Petrow_1970-160"><a href="#cite_ref-Petrow_1970_160-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPetrow1970" class="citation journal cs1">Petrow V (December 1970). "The contraceptive progestagens". Chemical Reviews. 70 (6): 713–726. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fcr60268a004">10.1021/cr60268a004</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/4098492">4098492</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+Reviews&rft.atitle=The+contraceptive+progestagens&rft.volume=70&rft.issue=6&rft.pages=713-726&rft.date=1970-12&rft_id=info%3Adoi%2F10.1021%2Fcr60268a004&rft_id=info%3Apmid%2F4098492&rft.aulast=Petrow&rft.aufirst=V&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Sneader_2005-161"><a href="#cite_ref-Sneader_2005_161-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSneader2005" class="citation book cs1">Sneader W (2005). "Hormone analogues". <a rel="nofollow" class="external text" href="https://archive.org/details/drugdiscoveryhis00snea">Drug discovery: a history</a>. Hoboken, NJ: John Wiley & Sons. pp. <a rel="nofollow" class="external text" href="https://archive.org/details/drugdiscoveryhis00snea/page/n201">188</a>–225. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-89980-8" title="Special:BookSources/978-0-471-89980-8"><bdi>978-0-471-89980-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Hormone+analogues&rft.btitle=Drug+discovery%3A+a+history&rft.place=Hoboken%2C+NJ&rft.pages=188-225&rft.pub=John+Wiley+%26+Sons&rft.date=2005&rft.isbn=978-0-471-89980-8&rft.aulast=Sneader&rft.aufirst=W&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fdrugdiscoveryhis00snea&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Djerassi_2006-162"><a href="#cite_ref-Djerassi_2006_162-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDjerassi2006" class="citation journal cs1">Djerassi C (January 2006). "Chemical birth of the pill. 1992". American Journal of Obstetrics and Gynecology. 194 (1): 290–298. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.ajog.2005.06.010">10.1016/j.ajog.2005.06.010</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16389046">16389046</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=American+Journal+of+Obstetrics+and+Gynecology&rft.atitle=Chemical+birth+of+the+pill.+1992&rft.volume=194&rft.issue=1&rft.pages=290-298&rft.date=2006-01&rft_id=info%3Adoi%2F10.1016%2Fj.ajog.2005.06.010&rft_id=info%3Apmid%2F16389046&rft.aulast=Djerassi&rft.aufirst=C&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Estinyl_2004-163"><a href="#cite_ref-Estinyl_2004_163-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFU.S._Food_and_Drug_Administration_(FDA)2004" class="citation journal cs1">U.S. <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> (FDA) (5 May 2004). <a rel="nofollow" class="external text" href="http://edocket.access.gpo.gov/2004/pdf/04-10194.pdf">"Schering Corp. et al.; Withdrawal of Approval of 92 New Drug Applications and 49 Abbreviated New Drug Applications. Notice"</a> (PDF). <a href="/wiki/Federal_Register" title="Federal Register">Federal Register</a>. 69 (87): 25124–30.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Federal+Register&rft.atitle=Schering+Corp.+et+al.%3B+Withdrawal+of+Approval+of+92+New+Drug+Applications+and+49+Abbreviated+New+Drug+Applications.+Notice&rft.volume=69&rft.issue=87&rft.pages=25124-30&rft.date=2004-05-05&rft.au=U.S.+Food+and+Drug+Administration+%28FDA%29&rft_id=http%3A%2F%2Fedocket.access.gpo.gov%2F2004%2Fpdf%2F04-10194.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-pmid13359169-164"><a href="#cite_ref-pmid13359169_164-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCantor1956" class="citation journal cs1">Cantor EB (September 1956). "A survey of estrogens". Postgraduate Medicine. 20 (3): 224–231. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F00325481.1956.11691266">10.1080/00325481.1956.11691266</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/13359169">13359169</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Postgraduate+Medicine&rft.atitle=A+survey+of+estrogens&rft.volume=20&rft.issue=3&rft.pages=224-231&rft.date=1956-09&rft_id=info%3Adoi%2F10.1080%2F00325481.1956.11691266&rft_id=info%3Apmid%2F13359169&rft.aulast=Cantor&rft.aufirst=EB&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-BellerKnörr1974-165"><a href="#cite_ref-BellerKnörr1974_165-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBellerKnörrLauritzenWynn1974" class="citation book cs1">Beller FK, Knörr K, Lauritzen C, Wynn RM (1974). "Family Planning". Gynecology. pp. 189–213. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-1-4615-7128-5_17">10.1007/978-1-4615-7128-5_17</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-387-90087-2" title="Special:BookSources/978-0-387-90087-2"><bdi>978-0-387-90087-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Family+Planning&rft.btitle=Gynecology&rft.pages=189-213&rft.date=1974&rft_id=info%3Adoi%2F10.1007%2F978-1-4615-7128-5_17&rft.isbn=978-0-387-90087-2&rft.aulast=Beller&rft.aufirst=FK&rft.au=Kn%C3%B6rr%2C+K&rft.au=Lauritzen%2C+C&rft.au=Wynn%2C+RM&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Haller1968-166"><a href="#cite_ref-Haller1968_166-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHaller1968" class="citation book cs1">Haller J (1968). "Die antikonzeptionelle Therapie". Die Gestagene. pp. 1125–1178. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-3-642-99941-3_8">10.1007/978-3-642-99941-3_8</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-99942-0" title="Special:BookSources/978-3-642-99942-0"><bdi>978-3-642-99942-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Die+antikonzeptionelle+Therapie&rft.btitle=Die+Gestagene&rft.pages=1125-1178&rft.date=1968&rft_id=info%3Adoi%2F10.1007%2F978-3-642-99941-3_8&rft.isbn=978-3-642-99942-0&rft.aulast=Haller&rft.aufirst=J&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Drugs.com-167">^ <a href="#cite_ref-Drugs.com_167-0">a</a> <a href="#cite_ref-Drugs.com_167-1">b</a> <a href="#cite_ref-Drugs.com_167-2">c</a> <a href="#cite_ref-Drugs.com_167-3">d</a> <a href="#cite_ref-Drugs.com_167-4">e</a> <a href="#cite_ref-Drugs.com_167-5">f</a> <a href="#cite_ref-Drugs.com_167-6">g</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.drugs.com/international/ethinylestradiol.html">"Ethinylestradiol - Drugs.com"</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Ethinylestradiol+-+Drugs.com&rft_id=https%3A%2F%2Fwww.drugs.com%2Finternational%2Fethinylestradiol.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-MortonHall2012-168"><a href="#cite_ref-MortonHall2012_168-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMortonHall2012" class="citation book cs1">Morton IK, Hall JM (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA115">Concise Dictionary of Pharmacological Agents: Properties and Synonyms</a>. Springer Science & Business Media. pp. 115–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-94-011-4439-1" title="Special:BookSources/978-94-011-4439-1"><bdi>978-94-011-4439-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Concise+Dictionary+of+Pharmacological+Agents%3A+Properties+and+Synonyms&rft.pages=115-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-94-011-4439-1&rft.aulast=Morton&rft.aufirst=IK&rft.au=Hall%2C+JM&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DtsjrCAAAQBAJ%26pg%3DPA115&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-AMA1977-169"><a href="#cite_ref-AMA1977_169-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAmerican_Medical_Association._Dept._of_DrugsCouncil_on_Drugs_(American_Medical_Association)American_Society_for_Clinical_Pharmacology_and_Therapeutics1977" class="citation book cs1">American Medical Association. Dept. of Drugs, Council on Drugs (American Medical Association), American Society for Clinical Pharmacology and Therapeutics (1 February 1977). "Estrogens, Progestagens, Oral Contraceptives, and Ovulatory Agents". <a rel="nofollow" class="external text" href="https://books.google.com/books?id=0h7s_rfEZgkC">AMA drug evaluations</a>. Publishing Sciences Group. pp. 540–572. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-88416-175-2" title="Special:BookSources/978-0-88416-175-2"><bdi>978-0-88416-175-2</bdi></a>. <q>Ethinyl Estradiol [Estinyl, Feminone, Lynoral, Novestrol, Palonyl]</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Estrogens%2C+Progestagens%2C+Oral+Contraceptives%2C+and+Ovulatory+Agents&rft.btitle=AMA+drug+evaluations&rft.pages=540-572&rft.pub=Publishing+Sciences+Group&rft.date=1977-02-01&rft.isbn=978-0-88416-175-2&rft.au=American+Medical+Association.+Dept.+of+Drugs&rft.au=Council+on+Drugs+%28American+Medical+Association%29&rft.au=American+Society+for+Clinical+Pharmacology+and+Therapeutics&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D0h7s_rfEZgkC&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-Pharmaceuticals1983-170"><a href="#cite_ref-Pharmaceuticals1983_170-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAmerican_Society_of_Hospital_Pharmacists._Committee_on_Pharmacy_and_Pharmaceuticals1983" class="citation book cs1">American Society of Hospital Pharmacists. Committee on Pharmacy and Pharmaceuticals (1983). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=bO0jAQAAMAAJ">American Hospital Formulary Service: A Two-volume Collection of Drug Monographs and Other Information</a>. American Society of Hospital Pharmacists. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-930530-02-0" title="Special:BookSources/978-0-930530-02-0"><bdi>978-0-930530-02-0</bdi></a>. <q>ETHINYL ESTRADIOL U.S.P. (Esteed®, Estinyl®, Lynoral®, Menolyn®, Novestrol®, Palonyl®, Spanestrin®, Ylestrol®)</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=American+Hospital+Formulary+Service%3A+A+Two-volume+Collection+of+Drug+Monographs+and+Other+Information&rft.pub=American+Society+of+Hospital+Pharmacists&rft.date=1983&rft.isbn=978-0-930530-02-0&rft.au=American+Society+of+Hospital+Pharmacists.+Committee+on+Pharmacy+and+Pharmaceuticals&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DbO0jAQAAMAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-171"><a href="#cite_ref-171">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://clincalc.com/DrugStats/Drugs/EthinylEstradiolNorgestimate">"Ethinyl Estradiol; Norgestimate Drug Usage Statistics, United States, 2013 - 2022"</a>. ClinCalc. Retrieved 30 August 2024.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=ClinCalc&rft.atitle=Ethinyl+Estradiol%3B+Norgestimate+Drug+Usage+Statistics%2C+United+States%2C+2013+-+2022&rft_id=https%3A%2F%2Fclincalc.com%2FDrugStats%2FDrugs%2FEthinylEstradiolNorgestimate&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-172"><a href="#cite_ref-172">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://clincalc.com/DrugStats/Drugs/EthinylEstradiolLevonorgestrel">"Ethinyl Estradiol; Levonorgestrel Drug Usage Statistics, United States, 2013 - 2022"</a>. ClinCalc. Retrieved 30 August 2024.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=ClinCalc&rft.atitle=Ethinyl+Estradiol%3B+Levonorgestrel+Drug+Usage+Statistics%2C+United+States%2C+2013+-+2022&rft_id=https%3A%2F%2Fclincalc.com%2FDrugStats%2FDrugs%2FEthinylEstradiolLevonorgestrel&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-173"><a href="#cite_ref-173">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://clincalc.com/DrugStats/Drugs/DrospirenoneEthinylEstradiol">"Drospirenone; Ethinyl Estradiol Drug Usage Statistics, United States, 2013 - 2022"</a>. ClinCalc. Retrieved 30 August 2024.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=ClinCalc&rft.atitle=Drospirenone%3B+Ethinyl+Estradiol+Drug+Usage+Statistics%2C+United+States%2C+2013+-+2022&rft_id=https%3A%2F%2Fclincalc.com%2FDrugStats%2FDrugs%2FDrospirenoneEthinylEstradiol&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-174"><a href="#cite_ref-174">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://clincalc.com/DrugStats/Drugs/DesogestrelEthinylEstradiol">"Desogestrel; Ethinyl Estradiol Drug Usage Statistics, United States, 2013 - 2022"</a>. ClinCalc. Retrieved 30 August 2024.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=ClinCalc&rft.atitle=Desogestrel%3B+Ethinyl+Estradiol+Drug+Usage+Statistics%2C+United+States%2C+2013+-+2022&rft_id=https%3A%2F%2Fclincalc.com%2FDrugStats%2FDrugs%2FDesogestrelEthinylEstradiol&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-175"><a href="#cite_ref-175">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://clincalc.com/DrugStats/Drugs/EthinylEstradiolEtonogestrel">"Ethinyl Estradiol ; Etonogestrel Drug Usage Statistics, United States, 2013 - 2022"</a>. ClinCalc. Retrieved 30 August 2024.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=ClinCalc&rft.atitle=Ethinyl+Estradiol+%3B+Etonogestrel+Drug+Usage+Statistics%2C+United+States%2C+2013+-+2022&rft_id=https%3A%2F%2Fclincalc.com%2FDrugStats%2FDrugs%2FEthinylEstradiolEtonogestrel&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-176"><a href="#cite_ref-176">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://clincalc.com/DrugStats/Drugs/EthinylEstradiolNorgestrel">"Ethinyl Estradiol ; Norgestrel Drug Usage Statistics, United States, 2013 - 2022"</a>. ClinCalc. Retrieved 30 August 2024.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=ClinCalc&rft.atitle=Ethinyl+Estradiol+%3B+Norgestrel+Drug+Usage+Statistics%2C+United+States%2C+2013+-+2022&rft_id=https%3A%2F%2Fclincalc.com%2FDrugStats%2FDrugs%2FEthinylEstradiolNorgestrel&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-177"><a href="#cite_ref-177">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://clincalc.com/DrugStats/Drugs/DrospirenoneEthinylEstradiolLevomefolate">"Drospirenone; Ethinyl Estradiol; Levomefolate Drug Usage Statistics, United States, 2013 - 2022"</a>. ClinCalc. Retrieved 30 August 2024.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=ClinCalc&rft.atitle=Drospirenone%3B+Ethinyl+Estradiol%3B+Levomefolate+Drug+Usage+Statistics%2C+United+States%2C+2013+-+2022&rft_id=https%3A%2F%2Fclincalc.com%2FDrugStats%2FDrugs%2FDrospirenoneEthinylEstradiolLevomefolate&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> <li id="cite_note-178"><a href="#cite_ref-178">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://clincalc.com/DrugStats/Drugs/EthinylEstradiolEthynodiol">"Ethinyl Estradiol; Ethynodiol Drug Usage Statistics, United States, 2013 - 2022"</a>. ClinCalc. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20240118044937/https://clincalc.com/DrugStats/Drugs/EthinylEstradiolEthynodiol">Archived</a> from the original on 18 January 2024. Retrieved 30 August 2024.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=ClinCalc&rft.atitle=Ethinyl+Estradiol%3B+Ethynodiol+Drug+Usage+Statistics%2C+United+States%2C+2013+-+2022&rft_id=https%3A%2F%2Fclincalc.com%2FDrugStats%2FDrugs%2FEthinylEstradiolEthynodiol&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2>[<a href="/w/index.php?title=Ethinylestradiol&action=edit&section=31" title="Edit section: Further reading">edit</a>]</div> <style data-mw-deduplicate="TemplateStyles:r1239549316">.mw-parser-output .refbegin{margin-bottom:0.5em}.mw-parser-output .refbegin-hanging-indents>ul{margin-left:0}.mw-parser-output .refbegin-hanging-indents>ul>li{margin-left:0;padding-left:3.2em;text-indent:-3.2em}.mw-parser-output .refbegin-hanging-indents ul,.mw-parser-output .refbegin-hanging-indents ul li{list-style:none}@media(max-width:720px){.mw-parser-output .refbegin-hanging-indents>ul>li{padding-left:1.6em;text-indent:-1.6em}}.mw-parser-output .refbegin-columns{margin-top:0.3em}.mw-parser-output .refbegin-columns ul{margin-top:0}.mw-parser-output .refbegin-columns li{page-break-inside:avoid;break-inside:avoid-column}@media screen{.mw-parser-output .refbegin{font-size:90%}}</style><div class="refbegin" style=""> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFOettelSchillinger2012" class="citation book cs1">Oettel M, Schillinger E (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=wBvyCAAAQBAJ">Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen</a>. Springer Science & Business Media. pp. 4, 10, 15, 165, 247–248, 276–291, 363–408, 424, 514, 540, 543, 581. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-60107-1" title="Special:BookSources/978-3-642-60107-1"><bdi>978-3-642-60107-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Estrogens+and+Antiestrogens+II%3A+Pharmacology+and+Clinical+Application+of+Estrogens+and+Antiestrogen&rft.pages=4%2C+10%2C+15%2C+165%2C+247-248%2C+276-291%2C+363-408%2C+424%2C+514%2C+540%2C+543%2C+581&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-3-642-60107-1&rft.aulast=Oettel&rft.aufirst=M&rft.au=Schillinger%2C+E&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DwBvyCAAAQBAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKuhl2005" class="citation journal cs1">Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric. 8 (Suppl 1): 3–63. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F13697130500148875">10.1080/13697130500148875</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16112947">16112947</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:24616324">24616324</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Climacteric&rft.atitle=Pharmacology+of+estrogens+and+progestogens%3A+influence+of+different+routes+of+administration&rft.volume=8&rft.issue=Suppl+1&rft.pages=3-63&rft.date=2005-08&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A24616324%23id-name%3DS2CID&rft_id=info%3Apmid%2F16112947&rft_id=info%3Adoi%2F10.1080%2F13697130500148875&rft.aulast=Kuhl&rft.aufirst=H&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFStanczykArcherBhavnani2013" class="citation journal cs1">Stanczyk FZ, Archer DF, Bhavnani BR (June 2013). "Ethinyl estradiol and 17β-estradiol in combined oral contraceptives: pharmacokinetics, pharmacodynamics and risk assessment". Contraception. 87 (6): 706–727. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.contraception.2012.12.011">10.1016/j.contraception.2012.12.011</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/23375353">23375353</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Contraception&rft.atitle=Ethinyl+estradiol+and+17%CE%B2-estradiol+in+combined+oral+contraceptives%3A+pharmacokinetics%2C+pharmacodynamics+and+risk+assessment&rft.volume=87&rft.issue=6&rft.pages=706-727&rft.date=2013-06&rft_id=info%3Adoi%2F10.1016%2Fj.contraception.2012.12.011&rft_id=info%3Apmid%2F23375353&rft.aulast=Stanczyk&rft.aufirst=FZ&rft.au=Archer%2C+DF&rft.au=Bhavnani%2C+BR&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMattisonKaryakinaGoodmanLaKind2014" class="citation journal cs1">Mattison DR, Karyakina N, Goodman M, LaKind JS (September 2014). "Pharmaco- and toxicokinetics of selected exogenous and endogenous estrogens: a review of the data and identification of knowledge gaps". Critical Reviews in Toxicology. 44 (8): 696–724. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3109%2F10408444.2014.930813">10.3109/10408444.2014.930813</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/25099693">25099693</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:11212469">11212469</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Critical+Reviews+in+Toxicology&rft.atitle=Pharmaco-+and+toxicokinetics+of+selected+exogenous+and+endogenous+estrogens%3A+a+review+of+the+data+and+identification+of+knowledge+gaps&rft.volume=44&rft.issue=8&rft.pages=696-724&rft.date=2014-09&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A11212469%23id-name%3DS2CID&rft_id=info%3Apmid%2F25099693&rft_id=info%3Adoi%2F10.3109%2F10408444.2014.930813&rft.aulast=Mattison&rft.aufirst=DR&rft.au=Karyakina%2C+N&rft.au=Goodman%2C+M&rft.au=LaKind%2C+JS&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthinylestradiol" class="Z3988"></li></ul> </div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1236075235">.mw-parser-output .navbox{box-sizing:border-box;border:1px solid #a2a9b1;width:100%;clear:both;font-size:88%;text-align:center;padding:1px;margin:1em auto 0}.mw-parser-output .navbox .navbox{margin-top:0}.mw-parser-output .navbox+.navbox,.mw-parser-output .navbox+.navbox-styles+.navbox{margin-top:-1px}.mw-parser-output .navbox-inner,.mw-parser-output .navbox-subgroup{width:100%}.mw-parser-output .navbox-group,.mw-parser-output .navbox-title,.mw-parser-output .navbox-abovebelow{padding:0.25em 1em;line-height:1.5em;text-align:center}.mw-parser-output .navbox-group{white-space:nowrap;text-align:right}.mw-parser-output .navbox,.mw-parser-output .navbox-subgroup{background-color:#fdfdfd}.mw-parser-output .navbox-list{line-height:1.5em;border-color:#fdfdfd}.mw-parser-output .navbox-list-with-group{text-align:left;border-left-width:2px;border-left-style:solid}.mw-parser-output tr+tr>.navbox-abovebelow,.mw-parser-output tr+tr>.navbox-group,.mw-parser-output tr+tr>.navbox-image,.mw-parser-output tr+tr>.navbox-list{border-top:2px solid #fdfdfd}.mw-parser-output .navbox-title{background-color:#ccf}.mw-parser-output .navbox-abovebelow,.mw-parser-output .navbox-group,.mw-parser-output .navbox-subgroup .navbox-title{background-color:#ddf}.mw-parser-output .navbox-subgroup .navbox-group,.mw-parser-output .navbox-subgroup .navbox-abovebelow{background-color:#e6e6ff}.mw-parser-output .navbox-even{background-color:#f7f7f7}.mw-parser-output .navbox-odd{background-color:transparent}.mw-parser-output .navbox .hlist td dl,.mw-parser-output .navbox .hlist td ol,.mw-parser-output .navbox .hlist td ul,.mw-parser-output .navbox td.hlist dl,.mw-parser-output .navbox td.hlist ol,.mw-parser-output .navbox td.hlist ul{padding:0.125em 0}.mw-parser-output .navbox .navbar{display:block;font-size:100%}.mw-parser-output .navbox-title .navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Estrogens_and_antiestrogens" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Estrogens_and_antiestrogens" title="Template:Estrogens and antiestrogens"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Estrogens_and_antiestrogens" title="Template talk:Estrogens and antiestrogens"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Estrogens_and_antiestrogens" title="Special:EditPage/Template:Estrogens and antiestrogens"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Estrogens_and_antiestrogens" style="font-size:114%;margin:0 4em"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogens</a> and <a href="/wiki/Antiestrogen" title="Antiestrogen">antiestrogens</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogens</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0;background:#DDDDFF;"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Steroidal: <a href="/wiki/Alfatradiol" title="Alfatradiol">Alfatradiol</a></li> <li>Certain <a href="/wiki/Androgen" title="Androgen">androgens</a>/<a href="/wiki/Anabolic_steroid" title="Anabolic steroid">anabolic steroids</a> (e.g., <a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">testosterone</a>, <a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">testosterone esters</a>, <a href="/wiki/Methyltestosterone" title="Methyltestosterone">methyltestosterone</a>, <a href="/wiki/Metandienone" title="Metandienone">metandienone</a>, <a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">nandrolone esters</a>) (via estrogenic metabolites)</li> <li>Certain <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestins</a> (e.g., <a href="/wiki/Norethisterone" title="Norethisterone">norethisterone</a>, <a href="/wiki/Noretynodrel" title="Noretynodrel">noretynodrel</a>, <a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">etynodiol diacetate</a>, <a href="/wiki/Tibolone" title="Tibolone">tibolone</a>)</li> <li><a href="/wiki/Clomestrone" title="Clomestrone">Clomestrone</a></li> <li><a href="/wiki/Cloxestradiol_acetate" title="Cloxestradiol acetate">Cloxestradiol acetate</a></li> <li><a href="/wiki/Conjugated_estriol" title="Conjugated estriol">Conjugated estriol</a></li> <li><a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a></li> <li><a href="/wiki/Epiestriol" title="Epiestriol">Epiestriol</a></li> <li><a href="/wiki/Epimestrol" title="Epimestrol">Epimestrol</a></li> <li><a href="/wiki/Esterified_estrogens" title="Esterified estrogens">Esterified estrogens</a></li> <li><a href="/wiki/Estetrol_(medication)" title="Estetrol (medication)">Estetrol</a>†</li> <li><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a></li> <li><a href="/wiki/List_of_estrogen_esters#Estradiol_esters" title="List of estrogen esters">Estradiol esters</a> (e.g., <a href="/wiki/Estradiol_acetate" title="Estradiol acetate">estradiol acetate</a>, <a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">estradiol benzoate</a>, <a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">estradiol cypionate</a>, <a href="/wiki/Estradiol_enanthate" class="mw-redirect" title="Estradiol enanthate">estradiol enanthate</a>, <a href="/wiki/Estradiol_undecylate" title="Estradiol undecylate">estradiol undecylate</a>, <a href="/wiki/Estradiol_valerate" title="Estradiol valerate">estradiol valerate</a>, <a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">polyestradiol phosphate</a>, <a href="/wiki/Estradiol_ester_mixture" class="mw-redirect" title="Estradiol ester mixture">estradiol ester mixtures</a> (<a href="/wiki/Climacteron" class="mw-redirect" title="Climacteron">Climacteron</a>))</li> <li><a href="/wiki/Estramustine_phosphate" title="Estramustine phosphate">Estramustine phosphate</a></li> <li><a href="/wiki/Estriol_(medication)" title="Estriol (medication)">Estriol</a></li> <li><a href="/wiki/List_of_estrogen_esters#Estriol_esters" title="List of estrogen esters">Estriol esters</a> (e.g., <a href="/wiki/Estriol_succinate" title="Estriol succinate">estriol succinate</a>, <a href="/wiki/Polyestriol_phosphate" title="Polyestriol phosphate">polyestriol phosphate</a>)</li> <li><a href="/wiki/Estrogenic_substances" title="Estrogenic substances">Estrogenic substances</a></li> <li><a href="/wiki/Estrone_(medication)" title="Estrone (medication)">Estrone</a></li> <li><a href="/wiki/List_of_estrogen_esters#Estrone_esters" title="List of estrogen esters">Estrone esters</a> <ul><li><a href="/wiki/Estrone_sulfate_(medication)" title="Estrone sulfate (medication)">Estrone sulfate</a></li> <li><a href="/wiki/Estropipate" title="Estropipate">Estropipate (piperazine estrone sulfate)</a></li></ul></li> <li><a class="mw-selflink selflink">Ethinylestradiol</a># <ul><li><a href="/wiki/Ethinylestradiol_sulfonate" title="Ethinylestradiol sulfonate">Ethinylestradiol sulfonate</a></li></ul></li> <li><a href="/wiki/Hydroxyestrone_diacetate" title="Hydroxyestrone diacetate">Hydroxyestrone diacetate</a></li> <li><a href="/wiki/Mestranol" title="Mestranol">Mestranol</a></li> <li><a href="/wiki/Methylestradiol" title="Methylestradiol">Methylestradiol</a></li> <li><a href="/wiki/Moxestrol" title="Moxestrol">Moxestrol</a></li> <li><a href="/wiki/Nilestriol" title="Nilestriol">Nilestriol</a></li> <li><a href="/wiki/Prasterone" title="Prasterone">Prasterone (dehydroepiandrosterone; DHEA)</a> <ul><li><a href="/wiki/Prasterone_enanthate" title="Prasterone enanthate">Prasterone enanthate</a></li> <li><a href="/wiki/Prasterone_sulfate" title="Prasterone sulfate">Prasterone sulfate</a></li></ul></li> <li><a href="/wiki/Promestriene" title="Promestriene">Promestriene</a></li> <li><a href="/wiki/Quinestradol" title="Quinestradol">Quinestradol</a></li> <li><a href="/wiki/Quinestrol" title="Quinestrol">Quinestrol</a></li></ul> <ul><li>Nonsteroidal: <a href="/wiki/Benzestrol" title="Benzestrol">Benzestrol</a></li> <li><a href="/wiki/Bifluranol" title="Bifluranol">Bifluranol</a></li> <li><a href="/wiki/Chlorotrianisene" title="Chlorotrianisene">Chlorotrianisene</a></li> <li><a href="/wiki/Dienestrol" title="Dienestrol">Dienestrol</a> <ul><li><a href="/wiki/Dienestrol_diacetate" title="Dienestrol diacetate">Dienestrol diacetate</a></li></ul></li> <li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol (stilbestrol)</a></li> <li><a href="/wiki/List_of_estrogen_esters#Diethylstilbestrol_esters" title="List of estrogen esters">Diethylstilbestrol esters/ethers</a> <ul><li><a href="/wiki/Dimestrol" title="Dimestrol">Dimestrol (diethylstilbestrol dimethyl ether)</a></li> <li><a href="/wiki/Fosfestrol" title="Fosfestrol">Fosfestrol (diethylstilbestrol diphosphate)</a></li> <li><a href="/wiki/Mestilbol" title="Mestilbol">Mestilbol (diethylstilbestrol monomethyl ether)</a></li></ul></li> <li><a href="/wiki/Doisynoestrol" title="Doisynoestrol">Doisynoestrol (fenocycline)</a></li> <li><a href="/wiki/Hexestrol" title="Hexestrol">Hexestrol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Hexestrol_esters" title="List of estrogen esters">Hexestrol esters</a></li></ul></li> <li><a href="/wiki/Methallenestril" title="Methallenestril">Methallenestril</a></li> <li><a href="/wiki/Methestrol" title="Methestrol">Methestrol (promethestrol)</a> <ul><li><a href="/wiki/Methestrol_dipropionate" title="Methestrol dipropionate">Methestrol dipropionate (promethestrol dipropionate)</a></li></ul></li> <li><a href="/wiki/Paroxypropione" title="Paroxypropione">Paroxypropione</a></li> <li><a href="/wiki/Quadrosilan" title="Quadrosilan">Quadrosilan</a></li> <li><a href="/wiki/Triphenylbromoethylene" title="Triphenylbromoethylene">Triphenylbromoethylene</a></li> <li><a href="/wiki/Triphenylchloroethylene" title="Triphenylchloroethylene">Triphenylchloroethylene</a></li> <li><a href="/wiki/Zeranol" title="Zeranol">Zeranol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Progonadotropin" title="Progonadotropin">Progonadotropins</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Antiandrogen" title="Antiandrogen">Antiandrogens</a> (e.g., <a href="/wiki/Bicalutamide" title="Bicalutamide">bicalutamide</a>)</li> <li><a href="/wiki/GnRH_agonist" class="mw-redirect" title="GnRH agonist"><abbr title="gonadotropin-releasing hormone">GnRH</abbr> agonists</a> (e.g., <a href="/wiki/Gonadotropin-releasing_hormone" title="Gonadotropin-releasing hormone"><abbr title="gonadotropin-releasing hormone">GnRH</abbr> (gonadorelin)</a>, <a href="/wiki/Leuprorelin" title="Leuprorelin">leuprorelin</a>)</li> <li><a href="/wiki/Gonadotropin" title="Gonadotropin">Gonadotropins</a> (e.g., <a href="/wiki/Follicle-stimulating_hormone" title="Follicle-stimulating hormone"><abbr title="follicle-stimulating hormone">FSH</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip follicle-stimulating hormone, <a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone"><abbr title="luteinizing hormone">LH</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip luteinizing hormone)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Antiestrogen" title="Antiestrogen">Antiestrogens</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0;background:#DDDDFF;"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor antagonists (incl. <a href="/wiki/Selective_estrogen_receptor_modulators" class="mw-redirect" title="Selective estrogen receptor modulators"><abbr title="selective estrogen receptor modulators">SERMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip selective estrogen receptor modulators/<a href="/wiki/Selective_estrogen_receptor_downregulators" class="mw-redirect" title="Selective estrogen receptor downregulators"><abbr title="selective estrogen receptor downregulators">SERDs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip selective estrogen receptor downregulators)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acolbifene" title="Acolbifene">Acolbifene</a>†</li> <li><a href="/wiki/Anordrin" title="Anordrin">Anordrin</a></li> <li><a href="/wiki/Bazedoxifene" title="Bazedoxifene">Bazedoxifene</a></li> <li><a href="/wiki/Broparestrol" title="Broparestrol">Broparestrol</a></li> <li><a href="/wiki/Clomifene" title="Clomifene">Clomifene</a>#</li> <li><a href="/wiki/Cyclofenil" title="Cyclofenil">Cyclofenil</a></li> <li><a href="/wiki/Enclomifene" title="Enclomifene">Enclomifene</a>†</li> <li><a href="/wiki/Epitiostanol" title="Epitiostanol">Epitiostanol</a></li> <li><a href="/wiki/Lasofoxifene" title="Lasofoxifene">Lasofoxifene</a></li> <li><a href="/wiki/Mepitiostane" title="Mepitiostane">Mepitiostane</a></li> <li><a href="/wiki/Ormeloxifene" title="Ormeloxifene">Ormeloxifene</a></li> <li><a href="/wiki/Ospemifene" title="Ospemifene">Ospemifene</a></li> <li><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a>#</li> <li><a href="/wiki/Toremifene" title="Toremifene">Toremifene</a></li></ul> <ul><li>Exclusively antagonistic: <a href="/wiki/Elacestrant" title="Elacestrant">Elacestrant</a></li> <li><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant</a></li></ul> <ul><li>Noncompetitive inhibitors: <a href="/wiki/Trilostane" title="Trilostane">Trilostane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Aromatase_inhibitor" title="Aromatase inhibitor">Aromatase inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li>First-generation: <a href="/wiki/Aminoglutethimide" title="Aminoglutethimide">Aminoglutethimide</a></li> <li><a href="/wiki/Testolactone" title="Testolactone">Testolactone</a></li></ul> <ul><li>Second-generation: <a href="/wiki/Fadrozole" title="Fadrozole">Fadrozole</a></li> <li><a href="/wiki/Formestane" title="Formestane">Formestane</a></li></ul> <ul><li>Third-generation: <a href="/wiki/Anastrozole" title="Anastrozole">Anastrozole</a></li> <li><a href="/wiki/Exemestane" title="Exemestane">Exemestane</a></li> <li><a href="/wiki/Letrozole" title="Letrozole">Letrozole</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Antigonadotropin" title="Antigonadotropin">Antigonadotropins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Androgen" title="Androgen">Androgens</a>/<a href="/wiki/Anabolic_steroid" title="Anabolic steroid">anabolic steroids</a> (e.g., <a href="/wiki/Testosterone" title="Testosterone">testosterone</a>, <a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">testosterone esters</a>, <a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">nandrolone esters</a>, <a href="/wiki/Oxandrolone" title="Oxandrolone">oxandrolone</a>, <a href="/wiki/Fluoxymesterone" title="Fluoxymesterone">fluoxymesterone</a>)</li> <li><a href="/wiki/D2_receptor" class="mw-redirect" title="D2 receptor">D2 receptor</a> <a href="/wiki/Dopamine_antagonist" title="Dopamine antagonist">antagonists</a> (<a href="/wiki/Prolactin" title="Prolactin">prolactin</a> releasers) (e.g., <a href="/wiki/Domperidone" title="Domperidone">domperidone</a>, <a href="/wiki/Metoclopramide" title="Metoclopramide">metoclopramide</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>, <a href="/wiki/Haloperidol" title="Haloperidol">haloperidol</a>, <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>, <a href="/wiki/Sulpiride" title="Sulpiride">sulpiride</a>)</li> <li><a href="/wiki/GnRH_agonist" class="mw-redirect" title="GnRH agonist"><abbr title="gonadotropin-releasing hormone">GnRH</abbr> agonists</a> (e.g., <a href="/wiki/Leuprorelin" title="Leuprorelin">leuprorelin</a>, <a href="/wiki/Goserelin" title="Goserelin">goserelin</a>)</li> <li><a href="/wiki/GnRH_antagonist" class="mw-redirect" title="GnRH antagonist"><abbr title="gonadotropin-releasing hormone">GnRH</abbr> antagonists</a> (e.g., <a href="/wiki/Cetrorelix" title="Cetrorelix">cetrorelix</a>, <a href="/wiki/Elagolix" title="Elagolix">elagolix</a>)</li> <li><a href="/wiki/Progestogen" title="Progestogen">Progestogens</a> (e.g., <a href="/wiki/Chlormadinone_acetate" title="Chlormadinone acetate">chlormadinone acetate</a>, <a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">cyproterone acetate</a>, <a href="/wiki/Gestonorone_caproate" title="Gestonorone caproate">gestonorone caproate</a>, <a href="/wiki/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">hydroxyprogesterone caproate</a>, <a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">medroxyprogesterone acetate</a>, <a href="/wiki/Megestrol_acetate" title="Megestrol acetate">megestrol acetate</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Mixed mechanism of action: <a href="/wiki/Danazol" title="Danazol">Danazol</a></li> <li><a href="/wiki/Gestrinone" title="Gestrinone">Gestrinone</a></li></ul> <ul><li>Androstenedione immunogens: <a href="/wiki/Androvax" title="Androvax">Androvax (androstenedione albumin)</a></li> <li><a href="/wiki/Ovandrotone_albumin" title="Ovandrotone albumin">Ovandrotone albumin (Fecundin)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0;background:#DDDDFF;"><div style="padding:0 0.25em"><div class="hlist"> <ul><li>#<a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li>‡<a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li>†<a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li>§Never to phase III</li></ul></li></ul> </div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators">Estrogen receptor modulators</a></dd> <dd><a href="/wiki/Template:Androgens_and_antiandrogens" title="Template:Androgens and antiandrogens">Androgens and antiandrogens</a></dd> <dd><a href="/wiki/Template:Progestogens_and_antiprogestogens" title="Template:Progestogens and antiprogestogens">Progestogens and antiprogestogens</a></dd> <dd><a href="/wiki/List_of_steroidal_estrogens" class="mw-redirect" title="List of steroidal estrogens">List of estrogens</a></dd></dl></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Estrogen_receptor_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Estrogen_receptor_modulators" title="Template talk:Estrogen receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Estrogen_receptor_modulators" title="Special:EditPage/Template:Estrogen receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Estrogen_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor">Estrogen receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Steroidal: <a href="/wiki/2-Hydroxyestradiol" title="2-Hydroxyestradiol">2-Hydroxyestradiol</a></li> <li><a href="/wiki/2-Hydroxyestrone" title="2-Hydroxyestrone">2-Hydroxyestrone</a></li> <li><a href="/wiki/3-Methyl-19-methyleneandrosta-3,5-dien-17%CE%B2-ol" title="3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol">3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol</a></li> <li><a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/w/index.php?title=3%CE%B1,5%CE%B1-Dihydrolevonorgestrel&action=edit&redlink=1" class="new" title="3α,5α-Dihydrolevonorgestrel (page does not exist)">3α,5α-Dihydrolevonorgestrel</a></li> <li><a href="/w/index.php?title=3%CE%B2,5%CE%B1-Dihydrolevonorgestrel&action=edit&redlink=1" class="new" title="3β,5α-Dihydrolevonorgestrel (page does not exist)">3β,5α-Dihydrolevonorgestrel</a></li> <li><a href="/wiki/3%CE%B1-Hydroxytibolone" title="3α-Hydroxytibolone">3α-Hydroxytibolone</a></li> <li><a href="/wiki/3%CE%B2-Hydroxytibolone" title="3β-Hydroxytibolone">3β-Hydroxytibolone</a></li> <li><a href="/wiki/3%CE%B2-Androstanediol" title="3β-Androstanediol">3β-Androstanediol</a></li> <li><a href="/wiki/4-Androstenediol" title="4-Androstenediol">4-Androstenediol</a></li> <li><a href="/wiki/4-Androstenedione" class="mw-redirect" title="4-Androstenedione">4-Androstenedione</a></li> <li><a href="/wiki/4-Fluoroestradiol" title="4-Fluoroestradiol">4-Fluoroestradiol</a></li> <li><a href="/wiki/4-Hydroxyestradiol" title="4-Hydroxyestradiol">4-Hydroxyestradiol</a></li> <li><a href="/wiki/4-Hydroxyestrone" title="4-Hydroxyestrone">4-Hydroxyestrone</a></li> <li><a href="/wiki/4-Methoxyestradiol" title="4-Methoxyestradiol">4-Methoxyestradiol</a></li> <li><a href="/wiki/4-Methoxyestrone" title="4-Methoxyestrone">4-Methoxyestrone</a></li> <li><a href="/wiki/5-Androstenediol" class="mw-redirect" title="5-Androstenediol">5-Androstenediol</a></li> <li><a href="/wiki/7-Keto-DHEA" title="7-Keto-DHEA">7-Oxo-DHEA</a></li> <li><a href="/wiki/7%CE%B1-Hydroxy-DHEA" title="7α-Hydroxy-DHEA">7α-Hydroxy-DHEA</a></li> <li><a href="/wiki/7%CE%B1-Methylestradiol" title="7α-Methylestradiol">7α-Methylestradiol</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/8,9-Dehydroestradiol" title="8,9-Dehydroestradiol">8,9-Dehydroestradiol</a></li> <li><a href="/wiki/8,9-Dehydroestrone" title="8,9-Dehydroestrone">8,9-Dehydroestrone</a></li> <li><a href="/wiki/8%CE%B2-VE2" title="8β-VE2">8β-VE2</a></li> <li><a href="/wiki/10%CE%B2,17%CE%B2-Dihydroxyestra-1,4-dien-3-one" title="10β,17β-Dihydroxyestra-1,4-dien-3-one">10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)</a></li> <li><a href="/wiki/11%CE%B2-Chloromethylestradiol" title="11β-Chloromethylestradiol">11β-Chloromethylestradiol</a></li> <li><a href="/wiki/11%CE%B2-Methoxyestradiol" title="11β-Methoxyestradiol">11β-Methoxyestradiol</a></li> <li><a href="/wiki/15%CE%B1-Hydroxyestradiol" title="15α-Hydroxyestradiol">15α-Hydroxyestradiol</a></li> <li><a href="/wiki/16-Ketoestradiol" title="16-Ketoestradiol">16-Ketoestradiol</a></li> <li><a href="/wiki/16-Ketoestrone" title="16-Ketoestrone">16-Ketoestrone</a></li> <li><a href="/wiki/16%CE%B1-Fluoroestradiol" class="mw-redirect" title="16α-Fluoroestradiol">16α-Fluoroestradiol</a></li> <li><a href="/wiki/16%CE%B1-Hydroxy-DHEA" title="16α-Hydroxy-DHEA">16α-Hydroxy-DHEA</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyestrone" title="16α-Hydroxyestrone">16α-Hydroxyestrone</a></li> <li><a href="/wiki/16%CE%B1-Iodoestradiol" class="mw-redirect" title="16α-Iodoestradiol">16α-Iodoestradiol</a></li> <li><a href="/wiki/16%CE%B1-LE2" title="16α-LE2">16α-LE2</a></li> <li><a href="/wiki/16%CE%B2-Hydroxyestrone" title="16β-Hydroxyestrone">16β-Hydroxyestrone</a></li> <li><a href="/wiki/16%CE%B2,17%CE%B1-Epiestriol" title="16β,17α-Epiestriol">16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)</a></li> <li><a href="/wiki/17%CE%B1-Estradiol" title="17α-Estradiol">17α-Estradiol</a> (<a href="/wiki/Alfatradiol" title="Alfatradiol">alfatradiol</a>)</li> <li><a href="/wiki/17%CE%B1-Dihydroequilenin" title="17α-Dihydroequilenin">17α-Dihydroequilenin</a></li> <li><a href="/wiki/17%CE%B1-Dihydroequilin" title="17α-Dihydroequilin">17α-Dihydroequilin</a></li> <li><a href="/wiki/17%CE%B1-Epiestriol" title="17α-Epiestriol">17α-Epiestriol (16α-hydroxy-17α-estradiol)</a></li> <li><a href="/wiki/17%CE%B1-Ethynyl-3%CE%B1-androstanediol" title="17α-Ethynyl-3α-androstanediol">17α-Ethynyl-3α-androstanediol</a></li> <li><a href="/wiki/17%CE%B1-Ethynyl-3%CE%B2-androstanediol" title="17α-Ethynyl-3β-androstanediol">17α-Ethynyl-3β-androstanediol</a></li> <li><a href="/wiki/17%CE%B2-Dihydroequilenin" title="17β-Dihydroequilenin">17β-Dihydroequilenin</a></li> <li><a href="/wiki/17%CE%B2-Dihydroequilin" title="17β-Dihydroequilin">17β-Dihydroequilin</a></li> <li><a href="/wiki/17%CE%B2-Methyl-17%CE%B1-dihydroequilenin" title="17β-Methyl-17α-dihydroequilenin">17β-Methyl-17α-dihydroequilenin</a></li> <li><a href="/wiki/Abiraterone" class="mw-redirect" title="Abiraterone">Abiraterone</a></li> <li><a href="/wiki/Abiraterone_acetate" title="Abiraterone acetate">Abiraterone acetate</a></li> <li><a href="/wiki/Alestramustine" title="Alestramustine">Alestramustine</a></li> <li><a href="/wiki/Almestrone" title="Almestrone">Almestrone</a></li> <li><a href="/wiki/Anabolic_steroid" title="Anabolic steroid">Anabolic steroids</a> (e.g., <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> and <a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">esters</a>, <a href="/wiki/Methyltestosterone" title="Methyltestosterone">methyltestosterone</a>, <a href="/wiki/Metandienone" title="Metandienone">metandienone (methandrostenolone)</a>, <a href="/wiki/Nandrolone" title="Nandrolone">nandrolone</a> and <a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">esters</a>, many others; via estrogenic metabolites)</li> <li><a href="/wiki/Atrimustine" title="Atrimustine">Atrimustine</a></li> <li><a href="/wiki/Bolandiol" title="Bolandiol">Bolandiol</a></li> <li><a href="/wiki/Bolandiol_dipropionate" title="Bolandiol dipropionate">Bolandiol dipropionate</a></li> <li><a href="/wiki/Butolame" title="Butolame">Butolame</a></li> <li><a href="/wiki/Clomestrone" title="Clomestrone">Clomestrone</a></li> <li><a href="/wiki/Cloxestradiol" title="Cloxestradiol">Cloxestradiol</a> <ul><li><a href="/wiki/Cloxestradiol_acetate" title="Cloxestradiol acetate">Cloxestradiol acetate</a></li></ul></li> <li><a href="/wiki/Conjugated_estriol" title="Conjugated estriol">Conjugated estriol</a></li> <li><a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a></li> <li><a href="/wiki/Cyclodiol" title="Cyclodiol">Cyclodiol</a></li> <li><a href="/wiki/Cyclotriol" title="Cyclotriol">Cyclotriol</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA-S</a></li> <li><a href="/wiki/Ent-Estradiol" title="Ent-Estradiol">ent-Estradiol</a></li> <li><a href="/wiki/Epiestriol" title="Epiestriol">Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)</a></li> <li><a href="/wiki/Epimestrol" title="Epimestrol">Epimestrol</a></li> <li><a href="/wiki/Equilenin" title="Equilenin">Equilenin</a></li> <li><a href="/wiki/Equilin" title="Equilin">Equilin</a></li> <li><a href="/wiki/ERA-63" title="ERA-63">ERA-63 (ORG-37663)</a></li> <li><a href="/wiki/Esterified_estrogens" title="Esterified estrogens">Esterified estrogens</a></li> <li><a href="/wiki/Estetrol" title="Estetrol">Estetrol</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estradiol_esters" title="List of estrogen esters">Estradiol esters</a></li> <li><a href="/wiki/Lipoidal_estradiol" title="Lipoidal estradiol">Lipoidal estradiol</a></li> <li><a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">Polyestradiol phosphate</a></li></ul></li> <li><a href="/wiki/Estramustine" title="Estramustine">Estramustine</a></li> <li><a href="/wiki/Estramustine_phosphate" title="Estramustine phosphate">Estramustine phosphate</a></li> <li><a href="/wiki/Estrapronicate" title="Estrapronicate">Estrapronicate</a></li> <li><a href="/wiki/Estrazinol" title="Estrazinol">Estrazinol</a></li> <li><a href="/wiki/Estriol" title="Estriol">Estriol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estriol_esters" title="List of estrogen esters">Estriol esters</a></li> <li><a href="/wiki/Polyestriol_phosphate" title="Polyestriol phosphate">Polyestriol phosphate</a></li></ul></li> <li><a href="/wiki/Estrofurate" title="Estrofurate">Estrofurate</a></li> <li><a href="/wiki/Estrogenic_substances" title="Estrogenic substances">Estrogenic substances</a></li> <li><a href="/wiki/Estromustine" title="Estromustine">Estromustine</a></li> <li><a href="/wiki/Estrone" title="Estrone">Estrone</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estrone_esters" title="List of estrogen esters">Estrone esters</a></li> <li><a href="/wiki/Estrone_methyl_ether" title="Estrone methyl ether">Estrone methyl ether</a></li> <li><a href="/wiki/Estropipate" title="Estropipate">Estropipate</a></li></ul></li> <li><a href="/wiki/Etamestrol" title="Etamestrol">Etamestrol (eptamestrol)</a></li> <li><a href="/wiki/Ethinylandrostenediol" title="Ethinylandrostenediol">Ethinylandrostenediol</a> <ul><li><a href="/wiki/Ethandrostate" title="Ethandrostate">Ethandrostate</a></li></ul></li> <li><a class="mw-selflink selflink">Ethinylestradiol</a> <ul><li><a href="/wiki/Ethinylestradiol_3-benzoate" class="mw-redirect" title="Ethinylestradiol 3-benzoate">Ethinylestradiol 3-benzoate</a></li> <li><a href="/wiki/Ethinylestradiol_sulfonate" title="Ethinylestradiol sulfonate">Ethinylestradiol sulfonate</a></li></ul></li> <li><a href="/wiki/Ethinylestriol" title="Ethinylestriol">Ethinylestriol</a></li> <li><a href="/wiki/Ethylestradiol" title="Ethylestradiol">Ethylestradiol</a></li> <li><a href="/wiki/Etynodiol" title="Etynodiol">Etynodiol</a></li> <li><a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">Etynodiol diacetate</a></li> <li><a href="/wiki/Hexolame" title="Hexolame">Hexolame</a></li> <li><a href="/wiki/Hippulin" title="Hippulin">Hippulin</a></li> <li><a href="/wiki/Hydroxyestrone_diacetate" title="Hydroxyestrone diacetate">Hydroxyestrone diacetate</a></li> <li><a href="/wiki/Lynestrenol" title="Lynestrenol">Lynestrenol</a></li> <li><a href="/wiki/Lynestrenol_phenylpropionate" title="Lynestrenol phenylpropionate">Lynestrenol phenylpropionate</a></li> <li><a href="/wiki/Mestranol" title="Mestranol">Mestranol</a></li> <li><a href="/wiki/Methylestradiol" title="Methylestradiol">Methylestradiol</a></li> <li><a href="/wiki/Moxestrol" title="Moxestrol">Moxestrol</a></li> <li><a href="/wiki/Mytatrienediol" title="Mytatrienediol">Mytatrienediol</a></li> <li><a href="/wiki/Nilestriol" title="Nilestriol">Nilestriol</a></li> <li><a href="/wiki/Norethisterone" title="Norethisterone">Norethisterone</a></li> <li><a href="/wiki/Noretynodrel" title="Noretynodrel">Noretynodrel</a></li> <li><a href="/wiki/Orestrate" title="Orestrate">Orestrate</a></li> <li><a href="/wiki/Pentolame" title="Pentolame">Pentolame</a></li> <li><a href="/wiki/Prodiame" title="Prodiame">Prodiame</a></li> <li><a href="/wiki/Prolame" title="Prolame">Prolame</a></li> <li><a href="/wiki/Promestriene" title="Promestriene">Promestriene</a></li> <li><a href="/wiki/RU-16117" title="RU-16117">RU-16117</a></li> <li><a href="/wiki/Quinestradol" title="Quinestradol">Quinestradol</a></li> <li><a href="/wiki/Quinestrol" title="Quinestrol">Quinestrol</a></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li></ul> <ul><li>Nonsteroidal: <a href="/wiki/(R,R)-Tetrahydrochrysene" title="(R,R)-Tetrahydrochrysene">(R,R)-THC</a></li> <li><a href="/wiki/(S,S)-Tetrahydrochrysene" title="(S,S)-Tetrahydrochrysene">(S,S)-THC</a></li> <li><a href="/wiki/2,8-Dihydroxyhexahydrochrysene" title="2,8-Dihydroxyhexahydrochrysene">2,8-DHHHC</a></li> <li><a href="/w/index.php?title=%CE%92-LGND1&action=edit&redlink=1" class="new" title="Β-LGND1 (page does not exist)">β-LGND1</a></li> <li><a href="/wiki/%CE%92-LGND2" title="Β-LGND2">β-LGND2 (GTx-878)</a></li> <li><a href="/w/index.php?title=AC-186&action=edit&redlink=1" class="new" title="AC-186 (page does not exist)">AC-186</a></li> <li><a href="/wiki/Allenestrol" title="Allenestrol">Allenestrol</a></li> <li><a href="/wiki/Allenolic_acid" title="Allenolic acid">Allenolic acid</a></li> <li><a href="/wiki/Benzestrol" title="Benzestrol">Benzestrol</a></li> <li><a href="/wiki/Bifluranol" title="Bifluranol">Bifluranol</a></li> <li><a href="/wiki/Bisdehydrodoisynolic_acid" title="Bisdehydrodoisynolic acid">Bisdehydrodoisynolic acid</a></li> <li><a href="/wiki/Butestrol" title="Butestrol">Butestrol</a></li> <li><a href="/wiki/Carbestrol" title="Carbestrol">Carbestrol</a></li> <li><a href="/wiki/D-15414" title="D-15414">D-15414</a></li> <li><a href="/wiki/DCW234" title="DCW234">DCW234</a></li> <li><a href="/wiki/Diarylpropionitrile" title="Diarylpropionitrile">Diarylpropionitrile</a></li> <li><a href="/wiki/Dienestrol" title="Dienestrol">Dienestrol</a> <ul><li><a href="/wiki/Dienestrol_diacetate" title="Dienestrol diacetate">Dienestrol diacetate</a></li></ul></li> <li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Diethylstilbestrol_esters" title="List of estrogen esters">Diethylstilbestrol esters</a></li></ul></li> <li><a href="/wiki/Dimestrol" title="Dimestrol">Dimestrol (dianisylhexene)</a></li> <li><a href="/wiki/Dimethylstilbestrol" title="Dimethylstilbestrol">Dimethylstilbestrol</a></li> <li><a href="/wiki/Doisynoestrol" title="Doisynoestrol">Doisynoestrol (fenocycline)</a></li> <li><a href="/wiki/Doisynolic_acid" title="Doisynolic acid">Doisynolic acid</a></li> <li><a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Elacestrant" title="Elacestrant">Elacestrant</a></li> <li><a href="/wiki/ERB-196" title="ERB-196">ERB-196 (WAY-202196)</a></li> <li><a href="/wiki/Erteberel" title="Erteberel">Erteberel (SERBA-1, LY-500307)</a></li> <li><a href="/wiki/Estrobin" title="Estrobin">Estrobin (DBE)</a></li> <li><a href="/wiki/Fenestrel" title="Fenestrel">Fenestrel</a></li> <li><a href="/wiki/FERb_033" title="FERb 033">FERb 033</a></li> <li><a href="/wiki/Fosfestrol" title="Fosfestrol">Fosfestrol (diethylstilbestrol diphosphate)</a></li> <li><a href="/wiki/Furostilbestrol" title="Furostilbestrol">Furostilbestrol (diethylstilbestrol difuroate)</a></li> <li><a href="/wiki/GTx-758" title="GTx-758">GTx-758</a></li> <li><a href="/wiki/Hexestrol" title="Hexestrol">Hexestrol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Hexestrol_esters" title="List of estrogen esters">Hexestrol esters</a></li></ul></li> <li><a href="/wiki/ICI-85966" title="ICI-85966">ICI-85966 (Stilbostat)</a></li> <li><a href="/wiki/M2613" title="M2613">M2613</a></li> <li><a href="/wiki/Meso-Butestrol" title="Meso-Butestrol">meso-Butestrol</a></li> <li><a href="/wiki/Meso-Hexestrol" class="mw-redirect" title="Meso-Hexestrol">meso-Hexestrol</a></li> <li><a href="/wiki/Mestilbol" title="Mestilbol">Mestilbol</a></li> <li><a href="/wiki/Methallenestril" title="Methallenestril">Methallenestril</a></li> <li><a href="/wiki/Methestrol" title="Methestrol">Methestrol</a></li> <li><a href="/wiki/Methestrol_dipropionate" title="Methestrol dipropionate">Methestrol dipropionate</a></li> <li><a href="/wiki/Paroxypropione" title="Paroxypropione">Paroxypropione</a></li> <li><a href="/wiki/Pentafluranol" title="Pentafluranol">Pentafluranol</a></li> <li><a href="/wiki/Phenestrol" title="Phenestrol">Phenestrol</a></li> <li><a href="/wiki/Prinaberel" title="Prinaberel">Prinaberel (ERB-041, WAY-202041)</a></li> <li><a href="/wiki/Propylpyrazoletriol" title="Propylpyrazoletriol">Propylpyrazoletriol</a></li> <li><a href="/wiki/Quadrosilan" title="Quadrosilan">Quadrosilan</a></li> <li><a href="/w/index.php?title=SC-3296&action=edit&redlink=1" class="new" title="SC-3296 (page does not exist)">SC-3296</a></li> <li><a href="/wiki/SC-4289" title="SC-4289">SC-4289</a></li> <li><a href="/wiki/SERBA-2" title="SERBA-2">SERBA-2</a></li> <li><a href="/wiki/SKF-82,958" title="SKF-82,958">SKF-82,958</a></li> <li><a href="/wiki/Terfluranol" title="Terfluranol">Terfluranol</a></li> <li><a href="/wiki/Triphenylbromoethylene" title="Triphenylbromoethylene">Triphenylbromoethylene</a></li> <li><a href="/wiki/Triphenylchloroethylene" title="Triphenylchloroethylene">Triphenylchloroethylene</a></li> <li><a href="/wiki/Triphenyliodoethylene" title="Triphenyliodoethylene">Triphenyliodoethylene</a></li> <li><a href="/wiki/Triphenylmethylethylene" title="Triphenylmethylethylene">Triphenylmethylethylene (triphenylpropene)</a></li> <li><a href="/wiki/WAY-166818" title="WAY-166818">WAY-166818</a></li> <li><a href="/w/index.php?title=WAY-169916&action=edit&redlink=1" class="new" title="WAY-169916 (page does not exist)">WAY-169916</a></li> <li><a href="/wiki/WAY-200070" title="WAY-200070">WAY-200070</a></li> <li><a href="/wiki/WAY-204688" title="WAY-204688">WAY-204688 (SIM-688)</a></li> <li><a href="/wiki/WAY-214156" title="WAY-214156">WAY-214156</a></li></ul> <ul><li>Unknown/unsorted: <a href="/wiki/ERB-26" title="ERB-26">ERB-26</a></li> <li><a href="/wiki/ERA-45" title="ERA-45">ERA-45</a></li> <li><a href="/wiki/ERB-79" title="ERB-79">ERB-79</a></li> <li><a href="/wiki/ZK-283197" title="ZK-283197">ZK-283197</a></li></ul> <ul><li>Xenoestrogens: <a href="/wiki/Anise" title="Anise">Anise</a>-related (e.g., <a href="/wiki/Anethole" title="Anethole">anethole</a>, <a href="/wiki/Anol" title="Anol">anol</a>, <a href="/wiki/Dianethole" title="Dianethole">dianethole</a>, <a href="/wiki/Dianol" title="Dianol">dianol</a>, <a href="/wiki/Photoanethole" title="Photoanethole">photoanethole</a>)</li> <li><a href="/wiki/Chalconoid" title="Chalconoid">Chalconoids</a> (e.g., <a href="/wiki/Isoliquiritigenin" title="Isoliquiritigenin">isoliquiritigenin</a>, <a href="/wiki/Phloretin" title="Phloretin">phloretin</a>, <a href="/wiki/Phlorizin" title="Phlorizin">phlorizin (phloridzin)</a>, <a href="/wiki/Wedelolactone" title="Wedelolactone">wedelolactone</a>)</li> <li><a href="/wiki/Coumestan" title="Coumestan">Coumestans</a> (e.g., <a href="/wiki/Coumestrol" title="Coumestrol">coumestrol</a>, <a href="/wiki/Psoralidin" title="Psoralidin">psoralidin</a>)</li> <li><a href="/wiki/Flavonoid" title="Flavonoid">Flavonoids</a> (incl. <a href="/wiki/7,8-Dihydroxyflavone" class="mw-redirect" title="7,8-Dihydroxyflavone">7,8-DHF</a>, <a href="/wiki/8-Prenylnaringenin" title="8-Prenylnaringenin">8-prenylnaringenin</a>, <a href="/wiki/Apigenin" title="Apigenin">apigenin</a>, <a href="/wiki/Baicalein" title="Baicalein">baicalein</a>, <a href="/wiki/Baicalin" title="Baicalin">baicalin</a>, <a href="/wiki/Biochanin_A" title="Biochanin A">biochanin A</a>, <a href="/wiki/Calycosin" title="Calycosin">calycosin</a>, <a href="/wiki/Catechin" title="Catechin">catechin</a>, <a href="/wiki/Daidzein" title="Daidzein">daidzein</a>, <a href="/wiki/Daidzin" title="Daidzin">daidzin</a>, <a href="/wiki/Epicatechin_gallate" title="Epicatechin gallate">ECG</a>, <a href="/wiki/Epigallocatechin_gallate" title="Epigallocatechin gallate">EGCG</a>, <a href="/wiki/Epicatechin" class="mw-redirect" title="Epicatechin">epicatechin</a>, <a href="/wiki/Equol" title="Equol">equol</a>, <a href="/wiki/Formononetin" title="Formononetin">formononetin</a>, <a href="/wiki/Glabrene" title="Glabrene">glabrene</a>, <a href="/wiki/Glabridin" title="Glabridin">glabridin</a>, <a href="/wiki/Genistein" title="Genistein">genistein</a>, <a href="/wiki/Genistin" title="Genistin">genistin</a>, <a href="/wiki/Glycitein" title="Glycitein">glycitein</a>, <a href="/wiki/Kaempferol" title="Kaempferol">kaempferol</a>, <a href="/wiki/Liquiritigenin" title="Liquiritigenin">liquiritigenin</a>, <a href="/wiki/Mirificin" title="Mirificin">mirificin</a>, <a href="/wiki/Myricetin" title="Myricetin">myricetin</a>, <a href="/wiki/Naringenin" title="Naringenin">naringenin</a>, <a href="/w/index.php?title=Penduletin&action=edit&redlink=1" class="new" title="Penduletin (page does not exist)">penduletin</a>, <a href="/wiki/Pinocembrin" title="Pinocembrin">pinocembrin</a>, <a href="/wiki/Prunetin" title="Prunetin">prunetin</a>, <a href="/wiki/Puerarin" title="Puerarin">puerarin</a>, <a href="/wiki/Quercetin" title="Quercetin">quercetin</a>, <a href="/wiki/Tectoridin" title="Tectoridin">tectoridin</a>, <a href="/wiki/Tectorigenin" title="Tectorigenin">tectorigenin</a>)</li> <li><a href="/wiki/Lavender_oil" title="Lavender oil">Lavender oil</a></li> <li><a href="/wiki/Lignan" title="Lignan">Lignans</a> (e.g., <a href="/wiki/Enterodiol" title="Enterodiol">enterodiol</a>, <a href="/wiki/Enterolactone" title="Enterolactone">enterolactone</a>, <a href="/wiki/Nyasol" title="Nyasol">nyasol (cis-hinokiresinol)</a>)</li> <li><a href="/wiki/Metalloestrogen" title="Metalloestrogen">Metalloestrogens</a> (e.g., <a href="/wiki/Cadmium" title="Cadmium">cadmium</a>)</li> <li><a href="/wiki/Pesticide" title="Pesticide">Pesticides</a> (e.g., <a href="/wiki/Alternariol" title="Alternariol">alternariol</a>, <a href="/wiki/Dieldrin" title="Dieldrin">dieldrin</a>, <a href="/wiki/Endosulfan" title="Endosulfan">endosulfan</a>, <a href="/wiki/Fenarimol" title="Fenarimol">fenarimol</a>, <a href="/wiki/HPTE" title="HPTE">HPTE</a>, <a href="/wiki/Methiocarb" title="Methiocarb">methiocarb</a>, <a href="/wiki/Methoxychlor" title="Methoxychlor">methoxychlor</a>, <a href="/wiki/Triclocarban" title="Triclocarban">triclocarban</a>, <a href="/wiki/Triclosan" title="Triclosan">triclosan</a>)</li> <li><a href="/wiki/Phytosteroid" title="Phytosteroid">Phytosteroids</a> (e.g., <a href="/wiki/Digitoxin" title="Digitoxin">digitoxin</a> (<a href="/wiki/Digitalis" title="Digitalis">digitalis</a>), <a href="/wiki/Diosgenin" title="Diosgenin">diosgenin</a>, <a href="/wiki/Guggulsterone" title="Guggulsterone">guggulsterone</a>)</li> <li><a href="/wiki/Phytosterol" title="Phytosterol">Phytosterols</a> (e.g., <a href="/wiki/%CE%92-sitosterol" class="mw-redirect" title="Β-sitosterol">β-sitosterol</a>, <a href="/wiki/Campesterol" title="Campesterol">campesterol</a>, <a href="/wiki/Stigmasterol" title="Stigmasterol">stigmasterol</a>)</li> <li><a href="/wiki/Resorcylic_acid_lactone" title="Resorcylic acid lactone">Resorcylic acid lactones</a> (e.g., <a href="/wiki/Zearalanone" title="Zearalanone">zearalanone</a>, <a href="/wiki/%CE%91-zearalenol" class="mw-redirect" title="Α-zearalenol">α-zearalenol</a>, <a href="/wiki/%CE%92-zearalenol" class="mw-redirect" title="Β-zearalenol">β-zearalenol</a>, <a href="/wiki/Zearalenone" title="Zearalenone">zearalenone</a>, <a href="/wiki/Zeranol" title="Zeranol">zeranol (α-zearalanol)</a>, <a href="/wiki/Taleranol" title="Taleranol">taleranol (teranol, β-zearalanol)</a>)</li> <li><a href="/wiki/Steroid" title="Steroid">Steroid</a>-like (e.g., <a href="/wiki/Deoxymiroestrol" class="mw-redirect" title="Deoxymiroestrol">deoxymiroestrol</a>, <a href="/wiki/Miroestrol" title="Miroestrol">miroestrol</a>)</li> <li><a href="/wiki/Stilbenoid" title="Stilbenoid">Stilbenoids</a> (e.g., <a href="/wiki/Resveratrol" title="Resveratrol">resveratrol</a>, <a href="/wiki/Rhaponticin" title="Rhaponticin">rhaponticin</a>)</li> <li><a href="/wiki/Synthetic_xenoestrogen" class="mw-redirect" title="Synthetic xenoestrogen">Synthetic xenoestrogens</a> (e.g., <a href="/wiki/Alkylphenol" title="Alkylphenol">alkylphenols</a>, <a href="/wiki/Bisphenol" title="Bisphenol">bisphenols</a> (e.g., <a href="/wiki/Bisphenol_A" title="Bisphenol A">BPA</a>, <a href="/wiki/Bisphenol_F" title="Bisphenol F">BPF</a>, <a href="/wiki/Bisphenol_S" title="Bisphenol S">BPS</a>), <a href="/wiki/Dichlorodiphenyltrichloroethane" class="mw-redirect" title="Dichlorodiphenyltrichloroethane">DDT</a>, <a href="/wiki/Paraben" title="Paraben">parabens</a>, <a href="/wiki/Polybrominated_biphenyl" title="Polybrominated biphenyl">PBBs</a>, <a href="/wiki/4-hydroxybenzoic_acid" class="mw-redirect" title="4-hydroxybenzoic acid">PHBA</a>, <a href="/wiki/Phthalate" class="mw-redirect" title="Phthalate">phthalates</a>, <a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">PCBs</a>)</li> <li>Others (e.g., <a href="/wiki/Agnuside" title="Agnuside">agnuside</a>, <a href="/w/index.php?title=Rotundifuran&action=edit&redlink=1" class="new" title="Rotundifuran (page does not exist)">rotundifuran</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Mixed (<a href="/wiki/Selective_estrogen_receptor_modulators" class="mw-redirect" title="Selective estrogen receptor modulators"><abbr title="Selective estrogen receptor modulators">SERMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Selective estrogen receptor modulators)</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Phenylbenzofuran" title="2-Phenylbenzofuran">2-Phenylbenzofuran</a></li> <li><a href="/w/index.php?title=2-Phenylbenzothiophene&action=edit&redlink=1" class="new" title="2-Phenylbenzothiophene (page does not exist)">2-Phenylbenzothiophene</a></li> <li><a href="/wiki/4%27-Hydroxynorendoxifen" title="4'-Hydroxynorendoxifen">4'-Hydroxynorendoxifen</a></li> <li><a href="/wiki/27-Hydroxycholesterol" title="27-Hydroxycholesterol">27-Hydroxycholesterol</a></li> <li><a href="/wiki/Acefluranol" title="Acefluranol">Acefluranol</a></li> <li><a href="/wiki/Acolbifene" title="Acolbifene">Acolbifene</a></li> <li><a href="/wiki/Afimoxifene" title="Afimoxifene">Afimoxifene</a></li> <li><a href="/wiki/Anordiol" title="Anordiol">Anordiol</a></li> <li><a href="/wiki/Anordrin" title="Anordrin">Anordrin</a></li> <li><a href="/wiki/Arzoxifene" title="Arzoxifene">Arzoxifene</a></li> <li><a href="/wiki/Bazedoxifene" title="Bazedoxifene">Bazedoxifene</a></li> <li><a href="/wiki/Brilanestrant" title="Brilanestrant">Brilanestrant</a></li> <li><a href="/wiki/Broparestrol" title="Broparestrol">Broparestrol</a></li> <li><a href="/wiki/Camizestrant" title="Camizestrant">Camizestrant</a></li> <li><a href="/wiki/Chlorotrianisene" title="Chlorotrianisene">Chlorotrianisene</a></li> <li><a href="/wiki/Clomifene" title="Clomifene">Clomifene</a></li> <li><a href="/wiki/Clomifenoxide" title="Clomifenoxide">Clomifenoxide</a></li> <li><a href="/w/index.php?title=CN-55945-27&action=edit&redlink=1" class="new" title="CN-55945-27 (page does not exist)">CN-55945-27</a></li> <li><a href="/wiki/Cyclofenil" title="Cyclofenil">Cyclofenil</a></li> <li><a href="/w/index.php?title=D-15413&action=edit&redlink=1" class="new" title="D-15413 (page does not exist)">D-15413</a></li> <li><a href="/wiki/Desmethylchlorotrianisene" title="Desmethylchlorotrianisene">Desmethylchlorotrianisene</a></li> <li><a href="/wiki/Droloxifene" title="Droloxifene">Droloxifene</a></li> <li><a href="/wiki/Enclomifene" title="Enclomifene">Enclomifene</a></li> <li><a href="/wiki/Endoxifen" title="Endoxifen">Endoxifen</a></li> <li><a href="/wiki/Etacstil" title="Etacstil">Etacstil (GW-5638, DPC-974)</a></li> <li><a href="/wiki/Ethamoxytriphetol" title="Ethamoxytriphetol">Ethamoxytriphetol (MER-25)</a></li> <li><a href="/wiki/Femarelle" title="Femarelle">Femarelle</a></li> <li><a href="/wiki/Fispemifene" title="Fispemifene">Fispemifene</a></li> <li><a href="/w/index.php?title=GW-7604&action=edit&redlink=1" class="new" title="GW-7604 (page does not exist)">GW-7604</a></li> <li><a href="/wiki/ICI-55548" class="mw-redirect" title="ICI-55548">ICI-55548</a></li> <li><a href="/wiki/Idoxifene" title="Idoxifene">Idoxifene</a></li> <li><a href="/wiki/Lasofoxifene" title="Lasofoxifene">Lasofoxifene</a></li> <li><a href="/wiki/Levormeloxifene" title="Levormeloxifene">Levormeloxifene</a></li> <li><a href="/wiki/LN-1643" class="mw-redirect" title="LN-1643">LN-1643</a></li> <li><a href="/wiki/LN-2299" class="mw-redirect" title="LN-2299">LN-2299</a></li> <li><a href="/w/index.php?title=LY-117018&action=edit&redlink=1" class="new" title="LY-117018 (page does not exist)">LY-117018</a></li> <li><a href="/wiki/Menerba" title="Menerba">Menerba</a></li> <li><a href="/wiki/Miproxifene" title="Miproxifene">Miproxifene</a></li> <li><a href="/wiki/Miproxifene_phosphate" title="Miproxifene phosphate">Miproxifene phosphate</a></li> <li><a href="/w/index.php?title=MRL-37&action=edit&redlink=1" class="new" title="MRL-37 (page does not exist)">MRL-37</a></li> <li><a href="/wiki/Nafoxidine" title="Nafoxidine">Nafoxidine</a></li> <li><a href="/wiki/Nitromifene" title="Nitromifene">Nitromifene</a></li> <li><a href="/wiki/NNC_45-0095" title="NNC 45-0095">NNC 45-0095</a></li> <li><a href="/w/index.php?title=NNC_45-0320&action=edit&redlink=1" class="new" title="NNC 45-0320 (page does not exist)">NNC 45-0320</a></li> <li><a href="/w/index.php?title=NNC_45-0781&action=edit&redlink=1" class="new" title="NNC 45-0781 (page does not exist)">NNC 45-0781</a></li> <li><a href="/w/index.php?title=NNC_45-1506&action=edit&redlink=1" class="new" title="NNC 45-1506 (page does not exist)">NNC 45-1506</a></li> <li><a href="/wiki/Ormeloxifene" title="Ormeloxifene">Ormeloxifene</a></li> <li><a href="/wiki/Ospemifene" title="Ospemifene">Ospemifene</a></li> <li><a href="/wiki/Panomifene" title="Panomifene">Panomifene</a></li> <li><a href="/wiki/Pipendoxifene" title="Pipendoxifene">Pipendoxifene</a></li> <li><a href="/w/index.php?title=Promensil&action=edit&redlink=1" class="new" title="Promensil (page does not exist)">Promensil</a></li> <li><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></li> <li><a href="/wiki/Rimostil" title="Rimostil">Rimostil (P-081)</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/w/index.php?title=SS1010&action=edit&redlink=1" class="new" title="SS1010 (page does not exist)">SS1010</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a></li> <li><a href="/wiki/TAS-108" title="TAS-108">TAS-108 (SR-16234)</a></li> <li><a href="/wiki/Toremifene" title="Toremifene">Toremifene</a></li> <li><a href="/wiki/Trioxifene" title="Trioxifene">Trioxifene</a></li> <li><a href="/w/index.php?title=TZE-5323&action=edit&redlink=1" class="new" title="TZE-5323 (page does not exist)">TZE-5323</a></li> <li><a href="/w/index.php?title=U-11555A&action=edit&redlink=1" class="new" title="U-11555A (page does not exist)">U-11555A</a></li> <li><a href="/w/index.php?title=U-11634&action=edit&redlink=1" class="new" title="U-11634 (page does not exist)">U-11634</a></li> <li><a href="/w/index.php?title=Y-134&action=edit&redlink=1" class="new" title="Y-134 (page does not exist)">Y-134</a></li> <li><a href="/wiki/Zindoxifene" title="Zindoxifene">Zindoxifene</a></li> <li><a href="/wiki/Zuclomifene" title="Zuclomifene">Zuclomifene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/(R,R)-Tetrahydrochrysene" title="(R,R)-Tetrahydrochrysene">(R,R)-THC</a></li> <li><a href="/wiki/7%CE%B2-Hydroxy-DHEA" title="7β-Hydroxy-DHEA">7β-Hydroxy-DHEA</a></li> <li><a href="/w/index.php?title=Chloroindazole&action=edit&redlink=1" class="new" title="Chloroindazole (page does not exist)">Chloroindazole</a></li> <li><a href="/wiki/Cytestrol_acetate" title="Cytestrol acetate">Cytestrol acetate</a></li> <li><a href="/w/index.php?title=EM-800&action=edit&redlink=1" class="new" title="EM-800 (page does not exist)">EM-800 (SCH-57050)</a></li> <li><a href="/wiki/Epitiostanol" title="Epitiostanol">Epitiostanol</a></li> <li><a href="/w/index.php?title=ERA-90&action=edit&redlink=1" class="new" title="ERA-90 (page does not exist)">ERA-90</a></li> <li><a href="/w/index.php?title=ERB-88&action=edit&redlink=1" class="new" title="ERB-88 (page does not exist)">ERB-88</a></li> <li><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant (ICI-182780)</a></li> <li><a href="/wiki/Glyceollin" title="Glyceollin">Glyceollins</a> (<a href="/wiki/Glyceollin_I" title="Glyceollin I">I</a>, <a href="/w/index.php?title=Glyceollin_II&action=edit&redlink=1" class="new" title="Glyceollin II (page does not exist)">II</a>, <a href="/wiki/Glyceollin_III" title="Glyceollin III">III</a>, <a href="/w/index.php?title=Glyceollin_IV&action=edit&redlink=1" class="new" title="Glyceollin IV (page does not exist)">IV</a>)</li> <li><a href="/wiki/ICI-164384" title="ICI-164384">ICI-164384</a></li> <li><a href="/w/index.php?title=MDL-101906&action=edit&redlink=1" class="new" title="MDL-101906 (page does not exist)">MDL-101906</a></li> <li><a href="/wiki/Mepitiostane" title="Mepitiostane">Mepitiostane</a></li> <li><a href="/wiki/Methylepitiostanol" title="Methylepitiostanol">Methylepitiostanol</a></li> <li><a href="/wiki/Methylpiperidinopyrazole" title="Methylpiperidinopyrazole">Methylpiperidinopyrazole</a></li> <li><a href="/wiki/MIBE" title="MIBE">MIBE</a></li> <li><a href="/w/index.php?title=Oxabicycloheptene_sulfonate&action=edit&redlink=1" class="new" title="Oxabicycloheptene sulfonate (page does not exist)">Oxabicycloheptene sulfonate</a></li> <li><a href="/wiki/Phenytoin" title="Phenytoin">Phenytoin</a></li> <li><a href="/wiki/PHTPP" title="PHTPP">PHTPP</a></li> <li><a href="/wiki/Prochloraz" title="Prochloraz">Prochloraz</a></li> <li><a href="/w/index.php?title=RU-39411&action=edit&redlink=1" class="new" title="RU-39411 (page does not exist)">RU-39411</a></li> <li><a href="/w/index.php?title=RU-58668&action=edit&redlink=1" class="new" title="RU-58668 (page does not exist)">RU-58668</a></li> <li><a href="/w/index.php?title=SS1020&action=edit&redlink=1" class="new" title="SS1020 (page does not exist)">SS1020</a></li> <li><a href="/wiki/TAS-108" title="TAS-108">TAS-108 (SR-16234)</a></li> <li><a href="/wiki/ZB716" title="ZB716">ZB716</a></li> <li><a href="/w/index.php?title=ZK-164015&action=edit&redlink=1" class="new" title="ZK-164015 (page does not exist)">ZK-164015</a></li> <li><a href="/w/index.php?title=ZK-191703&action=edit&redlink=1" class="new" title="ZK-191703 (page does not exist)">ZK-191703</a></li></ul> <ul><li>Coregulator-binding modulators: <a href="/wiki/ERX-11" title="ERX-11">ERX-11</a></li></ul> <ul><li>Noncompetitive inhibitors: <a href="/wiki/Trilostane" title="Trilostane">Trilostane</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/G_protein-coupled_estrogen_receptor" class="mw-redirect" title="G protein-coupled estrogen receptor"><abbr title="G protein-coupled estrogen receptor">GPER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip G protein-coupled estrogen receptor</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Methoxyestradiol" title="2-Methoxyestradiol">2-Methoxyestradiol</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/Afimoxifene" title="Afimoxifene">Afimoxifene (4-hydroxytamoxifen)</a></li> <li><a href="/wiki/Aldosterone" title="Aldosterone">Aldosterone</a></li> <li><a href="/wiki/Atrazine" title="Atrazine">Atrazine</a></li> <li><a href="/wiki/Bisphenol_A" title="Bisphenol A">Bisphenol A</a></li> <li><a href="/wiki/Daidzein" title="Daidzein">Daidzein</a></li> <li><a href="/wiki/DDT" title="DDT">DDT</a> (<a href="/wiki/P,p%27-DDT" class="mw-redirect" title="P,p'-DDT">p,p'-DDT</a>, <a href="/w/index.php?title=O%27,p%27-DDE&action=edit&redlink=1" class="new" title="O',p'-DDE (page does not exist)">o',p'-DDE</a>)</li> <li><a href="/wiki/Diarylpropionitrile" title="Diarylpropionitrile">Diarylpropionitrile</a></li> <li><a href="/wiki/Equol" title="Equol">Equol</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a class="mw-selflink selflink">Ethinylestradiol</a></li> <li><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant (ICI-182780)</a></li> <li><a href="/w/index.php?title=G-1_(drug)&action=edit&redlink=1" class="new" title="G-1 (drug) (page does not exist)">G-1</a></li> <li><a href="/wiki/Genistein" title="Genistein">Genistein</a></li> <li><a href="/w/index.php?title=GPER-L1&action=edit&redlink=1" class="new" title="GPER-L1 (page does not exist)">GPER-L1</a></li> <li><a href="/w/index.php?title=GPER-L2&action=edit&redlink=1" class="new" title="GPER-L2 (page does not exist)">GPER-L2</a></li> <li><a href="/wiki/Hydroxytyrosol" title="Hydroxytyrosol">Hydroxytyrosol</a></li> <li><a href="/wiki/Kepone" class="mw-redirect" title="Kepone">Kepone</a></li> <li><a href="/wiki/Niacin" title="Niacin">Niacin</a></li> <li><a href="/wiki/Niacinamide" class="mw-redirect" title="Niacinamide">Niacinamide</a></li> <li><a href="/wiki/Nonylphenol" title="Nonylphenol">Nonylphenol</a></li> <li><a href="/wiki/Oleuropein" title="Oleuropein">Oleuropein</a></li> <li><a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">PCBs</a> (<a href="/w/index.php?title=2,2%27,5%27-PCB-4-OH&action=edit&redlink=1" class="new" title="2,2',5'-PCB-4-OH (page does not exist)">2,2',5'-PCB-4-OH</a>)</li> <li><a href="/wiki/Propylpyrazoletriol" title="Propylpyrazoletriol">Propylpyrazoletriol</a></li> <li><a href="/wiki/Quercetin" title="Quercetin">Quercetin</a></li> <li><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></li> <li><a href="/wiki/Resveratrol" title="Resveratrol">Resveratrol</a></li> <li><a href="/w/index.php?title=STX_(drug)&action=edit&redlink=1" class="new" title="STX (drug) (page does not exist)">STX</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a></li> <li><a href="/wiki/Tectoridin" title="Tectoridin">Tectoridin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/CCL18" title="CCL18">CCL18</a></li> <li><a href="/wiki/Estriol" title="Estriol">Estriol</a></li> <li><a href="/w/index.php?title=G-15_(drug)&action=edit&redlink=1" class="new" title="G-15 (drug) (page does not exist)">G-15</a></li> <li><a href="/w/index.php?title=G-36_(drug)&action=edit&redlink=1" class="new" title="G-36 (drug) (page does not exist)">G-36</a></li> <li><a href="/wiki/MIBE" title="MIBE">MIBE</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Unknown</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a></li> <li><a href="/wiki/Zearalenone" title="Zearalenone">Zearalenone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Estrogens_and_antiestrogens" title="Template:Estrogens and antiestrogens">Estrogens and antiestrogens</a></dd> <dd><a href="/wiki/Template:Androgen_receptor_modulators" title="Template:Androgen receptor modulators">Androgen receptor modulators</a></dd> <dd><a href="/wiki/Template:Progesterone_receptor_modulators" title="Template:Progesterone receptor modulators">Progesterone receptor modulators</a></dd> <dd><a href="/wiki/List_of_steroidal_estrogens" class="mw-redirect" title="List of steroidal estrogens">List of estrogens</a></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Xenobiotic-sensing_receptor_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Xenobiotic-sensing_receptor_modulators" title="Template:Xenobiotic-sensing receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Xenobiotic-sensing_receptor_modulators" title="Template talk:Xenobiotic-sensing receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Xenobiotic-sensing_receptor_modulators" title="Special:EditPage/Template:Xenobiotic-sensing receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Xenobiotic-sensing_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Xenobiotic-sensing_receptor" title="Xenobiotic-sensing receptor">Xenobiotic-sensing receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Constitutive_androstane_receptor" title="Constitutive androstane receptor"><abbr title="Constitutive androstane receptor">CAR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Constitutive androstane receptor</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/w/index.php?title=6,7-Dimethylesculetin&action=edit&redlink=1" class="new" title="6,7-Dimethylesculetin (page does not exist)">6,7-Dimethylesculetin</a></li> <li><a href="/wiki/Amiodarone" title="Amiodarone">Amiodarone</a></li> <li><a href="/wiki/Artemisinin" title="Artemisinin">Artemisinin</a></li> <li><a href="/w/index.php?title=Benfuracarb&action=edit&redlink=1" class="new" title="Benfuracarb (page does not exist)">Benfuracarb</a></li> <li><a href="/wiki/Carbamazepine" title="Carbamazepine">Carbamazepine</a></li> <li><a href="/wiki/Carvedilol" title="Carvedilol">Carvedilol</a></li> <li><a href="/wiki/Chlorpromazine" title="Chlorpromazine">Chlorpromazine</a></li> <li><a href="/wiki/Chrysin" title="Chrysin">Chrysin</a></li> <li><a href="/w/index.php?title=CITCO_(drug)&action=edit&redlink=1" class="new" title="CITCO (drug) (page does not exist)">CITCO</a></li> <li><a href="/wiki/Clotrimazole" title="Clotrimazole">Clotrimazole</a></li> <li><a href="/wiki/Cyclophosphamide" title="Cyclophosphamide">Cyclophosphamide</a></li> <li><a href="/wiki/Cypermethrin" title="Cypermethrin">Cypermethrin</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a> (<a href="/wiki/Prasterone" title="Prasterone">prasterone</a>)</li> <li><a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Ellagic_acid" title="Ellagic acid">Ellagic acid</a></li> <li><a href="/wiki/Griseofulvin" title="Griseofulvin">Griseofulvin</a></li> <li><a href="/wiki/Methoxychlor" title="Methoxychlor">Methoxychlor</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li> <li><a href="/wiki/Nefazodone" title="Nefazodone">Nefazodone</a></li> <li><a href="/wiki/Nevirapine" title="Nevirapine">Nevirapine</a></li> <li><a href="/wiki/Nicardipine" title="Nicardipine">Nicardipine</a></li> <li><a href="/w/index.php?title=Octicizer&action=edit&redlink=1" class="new" title="Octicizer (page does not exist)">Octicizer</a></li> <li><a href="/wiki/Permethrin" title="Permethrin">Permethrin</a></li> <li><a href="/wiki/Phenobarbital" title="Phenobarbital">Phenobarbital</a></li> <li><a href="/wiki/Phenytoin" title="Phenytoin">Phenytoin</a></li> <li><a href="/wiki/5%CE%B2-Dihydroprogesterone" title="5β-Dihydroprogesterone">Pregnanedione (5β-dihydroprogesterone)</a></li> <li><a href="/wiki/Reserpine" title="Reserpine">Reserpine</a></li> <li><a href="/w/index.php?title=TCPOBOP&action=edit&redlink=1" class="new" title="TCPOBOP (page does not exist)">TCPOBOP</a></li> <li><a href="/wiki/Telmisartan" title="Telmisartan">Telmisartan</a></li> <li><a href="/wiki/Tolnaftate" title="Tolnaftate">Tolnaftate</a></li> <li><a href="/wiki/Troglitazone" title="Troglitazone">Troglitazone</a></li> <li><a href="/wiki/Valproic_acid" class="mw-redirect" title="Valproic acid">Valproic acid</a></li></ul> <ul><li>Antagonists: <a href="/w/index.php?title=3,17%CE%B2-Estradiol&action=edit&redlink=1" class="new" title="3,17β-Estradiol (page does not exist)">3,17β-Estradiol</a></li> <li><a href="/w/index.php?title=5%CE%B1-Androstan-3%CE%B1-ol&action=edit&redlink=1" class="new" title="5α-Androstan-3α-ol (page does not exist)">3α-Androstanol</a></li> <li><a href="/wiki/5%CE%B1-Androst-16-en-3%CE%B1-ol" class="mw-redirect" title="5α-Androst-16-en-3α-ol">3α-Androstenol</a></li> <li><a href="/w/index.php?title=5%CE%B1-Androstan-3%CE%B2-ol&action=edit&redlink=1" class="new" title="5α-Androstan-3β-ol (page does not exist)">3β-Androstanol</a></li> <li><a href="/w/index.php?title=5%CE%B1-Androstan-17-ol&action=edit&redlink=1" class="new" title="5α-Androstan-17-ol (page does not exist)">17-Androstanol</a></li> <li><a href="/wiki/Allyl_isothiocyanate" title="Allyl isothiocyanate">AITC</a></li> <li><a class="mw-selflink selflink">Ethinylestradiol</a></li> <li><a href="/wiki/Meclizine" title="Meclizine">Meclizine</a></li> <li><a href="/w/index.php?title=Nigramide_J&action=edit&redlink=1" class="new" title="Nigramide J (page does not exist)">Nigramide J</a></li> <li><a href="/wiki/Okadaic_acid" title="Okadaic acid">Okadaic acid</a></li> <li><a href="/wiki/PK-11195" class="mw-redirect" title="PK-11195">PK-11195</a></li> <li><a href="/w/index.php?title=S-07662&action=edit&redlink=1" class="new" title="S-07662 (page does not exist)">S-07662</a></li> <li><a href="/w/index.php?title=T-0901317&action=edit&redlink=1" class="new" title="T-0901317 (page does not exist)">T-0901317</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Pregnane_X_receptor" title="Pregnane X receptor"><abbr title="Pregnane X receptor">PXR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Pregnane X receptor</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/17%CE%B1-Hydroxypregnenolone" title="17α-Hydroxypregnenolone">17α-Hydroxypregnenolone</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone</a></li> <li><a href="/wiki/%CE%944-Androstenedione" class="mw-redirect" title="Δ4-Androstenedione">Δ4-Androstenedione</a></li> <li><a href="/wiki/%CE%945-Androstenediol" class="mw-redirect" title="Δ5-Androstenediol">Δ5-Androstenediol</a></li> <li><a href="/wiki/%CE%945-Androstenedione" class="mw-redirect" title="Δ5-Androstenedione">Δ5-Androstenedione</a></li> <li><a href="/w/index.php?title=AA-861&action=edit&redlink=1" class="new" title="AA-861 (page does not exist)">AA-861</a></li> <li><a href="/wiki/Allopregnanediol" title="Allopregnanediol">Allopregnanediol</a></li> <li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">Allopregnanedione (5α-dihydroprogesterone)</a></li> <li><a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone (brexanolone)</a></li> <li><a href="/wiki/Alpha-Lipoic_acid" class="mw-redirect" title="Alpha-Lipoic acid">Alpha-Lipoic acid</a></li> <li><a href="/wiki/Ambrisentan" title="Ambrisentan">Ambrisentan</a></li> <li><a href="/wiki/AMI-193" class="mw-redirect" title="AMI-193">AMI-193</a></li> <li><a href="/wiki/Amlodipine_besylate" class="mw-redirect" title="Amlodipine besylate">Amlodipine besylate</a></li> <li><a href="/wiki/Antimycotic" class="mw-redirect" title="Antimycotic">Antimycotics</a></li> <li><a href="/wiki/Artemisinin" title="Artemisinin">Artemisinin</a></li> <li><a href="/wiki/Aurothioglucose" title="Aurothioglucose">Aurothioglucose</a></li> <li><a href="/wiki/Bile_acid" title="Bile acid">Bile acids</a></li> <li><a href="/wiki/Bithionol" title="Bithionol">Bithionol</a></li> <li><a href="/wiki/Bosentan" title="Bosentan">Bosentan</a></li> <li><a href="/w/index.php?title=Bumecaine&action=edit&redlink=1" class="new" title="Bumecaine (page does not exist)">Bumecaine</a></li> <li><a href="/wiki/Cafestol" title="Cafestol">Cafestol</a></li> <li><a href="/wiki/Cephaloridine" title="Cephaloridine">Cephaloridine</a></li> <li><a href="/wiki/Cephradine" class="mw-redirect" title="Cephradine">Cephradine</a></li> <li><a href="/wiki/Chlorpromazine" title="Chlorpromazine">Chlorpromazine</a></li> <li><a href="/wiki/Ciglitazone" title="Ciglitazone">Ciglitazone</a></li> <li><a href="/wiki/Clindamycin" title="Clindamycin">Clindamycin</a></li> <li><a href="/wiki/Clofenvinfos" class="mw-redirect" title="Clofenvinfos">Clofenvinfos</a></li> <li><a href="/wiki/Chloroxine" title="Chloroxine">Chloroxine</a></li> <li><a href="/wiki/Clotrimazole" title="Clotrimazole">Clotrimazole</a></li> <li><a href="/wiki/Colforsin" class="mw-redirect" title="Colforsin">Colforsin</a></li> <li><a href="/wiki/Corticosterone" title="Corticosterone">Corticosterone</a></li> <li><a href="/wiki/Cyclophosphamide" title="Cyclophosphamide">Cyclophosphamide</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Demecolcine" title="Demecolcine">Demecolcine</a></li> <li><a href="/wiki/Dexamethasone" title="Dexamethasone">Dexamethasone</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a> (<a href="/wiki/Prasterone" title="Prasterone">prasterone</a>)</li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA-S</a> (<a href="/wiki/Prasterone_sulfate" title="Prasterone sulfate">prasterone sulfate</a>)</li> <li><a href="/wiki/Dibunate_sodium" class="mw-redirect" title="Dibunate sodium">Dibunate sodium</a></li> <li><a href="/wiki/Diclazuril" title="Diclazuril">Diclazuril</a></li> <li><a href="/wiki/Dicloxacillin" title="Dicloxacillin">Dicloxacillin</a></li> <li><a href="/wiki/Dimercaprol" title="Dimercaprol">Dimercaprol</a></li> <li><a href="/w/index.php?title=Dinaline&action=edit&redlink=1" class="new" title="Dinaline (page does not exist)">Dinaline</a></li> <li><a href="/wiki/Docetaxel" title="Docetaxel">Docetaxel</a></li> <li><a href="/wiki/Docusate_calcium" class="mw-redirect" title="Docusate calcium">Docusate calcium</a></li> <li><a href="/wiki/Dodecylbenzenesulfonic_acid" class="mw-redirect" title="Dodecylbenzenesulfonic acid">Dodecylbenzenesulfonic acid</a></li> <li><a href="/wiki/Dronabinol" title="Dronabinol">Dronabinol</a></li> <li><a href="/wiki/Droxidopa" title="Droxidopa">Droxidopa</a></li> <li><a href="/wiki/Eburnamonine" class="mw-redirect" title="Eburnamonine">Eburnamonine</a></li> <li><a href="/wiki/Ecopipam" title="Ecopipam">Ecopipam</a></li> <li><a href="/wiki/Enzacamene" title="Enzacamene">Enzacamene</a></li> <li><a href="/wiki/Epothilone_B" class="mw-redirect" title="Epothilone B">Epothilone B</a></li> <li><a href="/wiki/Erythromycin" title="Erythromycin">Erythromycin</a></li> <li><a href="/wiki/Famprofazone" title="Famprofazone">Famprofazone</a></li> <li><a href="/w/index.php?title=Febantel&action=edit&redlink=1" class="new" title="Febantel (page does not exist)">Febantel</a></li> <li><a href="/wiki/Felodipine" title="Felodipine">Felodipine</a></li> <li><a href="/wiki/Fenbendazole" title="Fenbendazole">Fenbendazole</a></li> <li><a href="/wiki/Fentanyl" title="Fentanyl">Fentanyl</a></li> <li><a href="/wiki/Flucloxacillin" title="Flucloxacillin">Flucloxacillin</a></li> <li><a href="/wiki/Fluorometholone" title="Fluorometholone">Fluorometholone</a></li> <li><a href="/wiki/Griseofulvin" title="Griseofulvin">Griseofulvin</a></li> <li><a href="/wiki/Guggulsterone" title="Guggulsterone">Guggulsterone</a></li> <li><a href="/wiki/Haloprogin" title="Haloprogin">Haloprogin</a></li> <li><a href="/wiki/Hetacillin_potassium" class="mw-redirect" title="Hetacillin potassium">Hetacillin potassium</a></li> <li><a href="/wiki/Hyperforin" title="Hyperforin">Hyperforin</a></li> <li><a href="/wiki/Hypericum_perforatum" title="Hypericum perforatum">Hypericum perforatum (St John's wort)</a></li> <li><a href="/wiki/Indinavir_sulfate" class="mw-redirect" title="Indinavir sulfate">Indinavir sulfate</a></li> <li><a href="/wiki/Lasalocid_sodium" class="mw-redirect" title="Lasalocid sodium">Lasalocid sodium</a></li> <li><a href="/wiki/Levothyroxine" title="Levothyroxine">Levothyroxine</a></li> <li>Linolenic acid: <a href="/wiki/%CE%91-Linolenic_acid" title="Α-Linolenic acid">α-Linolenic acid</a> and <a href="/wiki/Gamma-Linolenic_acid" class="mw-redirect" title="Gamma-Linolenic acid">γ-linolenic acid</a></li> <li><a href="/w/index.php?title=LOE-908&action=edit&redlink=1" class="new" title="LOE-908 (page does not exist)">LOE-908</a></li> <li><a href="/wiki/Loratadine" title="Loratadine">Loratadine</a></li> <li><a href="/wiki/Lovastatin" title="Lovastatin">Lovastatin</a></li> <li><a href="/wiki/Meclizine" title="Meclizine">Meclizine</a></li> <li><a href="/wiki/Metacycline" title="Metacycline">Metacycline</a></li> <li><a href="/wiki/Methylprednisolone" title="Methylprednisolone">Methylprednisolone</a></li> <li><a href="/wiki/Metyrapone" title="Metyrapone">Metyrapone</a></li> <li><a href="/wiki/Mevastatin" title="Mevastatin">Mevastatin</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li> <li><a href="/wiki/Nafcillin" title="Nafcillin">Nafcillin</a></li> <li><a href="/wiki/Nicardipine" title="Nicardipine">Nicardipine</a></li> <li><a href="/wiki/Nicotine" title="Nicotine">Nicotine</a></li> <li><a href="/wiki/Nifedipine" title="Nifedipine">Nifedipine</a></li> <li><a href="/wiki/Nilvadipine" title="Nilvadipine">Nilvadipine</a></li> <li><a href="/wiki/Nisoldipine" title="Nisoldipine">Nisoldipine</a></li> <li><a href="/wiki/Norelgestromin" title="Norelgestromin">Norelgestromin</a></li> <li><a href="/wiki/Omeprazole" title="Omeprazole">Omeprazole</a></li> <li><a href="/wiki/Orlistat" title="Orlistat">Orlistat</a></li> <li><a href="/wiki/Oxatomide" title="Oxatomide">Oxatomide</a></li> <li><a href="/wiki/Paclitaxel" title="Paclitaxel">Paclitaxel</a></li> <li><a href="/wiki/Phenobarbital" title="Phenobarbital">Phenobarbital</a></li> <li><a href="/wiki/Piperine" title="Piperine">Piperine</a></li> <li><a href="/wiki/Plicamycin" title="Plicamycin">Plicamycin</a></li> <li><a href="/wiki/Prednisolone" title="Prednisolone">Prednisolone</a></li> <li><a href="/wiki/Pregnanediol" title="Pregnanediol">Pregnanediol</a></li> <li><a href="/wiki/5%CE%B2-Dihydroprogesterone" title="5β-Dihydroprogesterone">Pregnanedione (5β-dihydroprogesterone)</a></li> <li><a href="/wiki/Pregnanolone" title="Pregnanolone">Pregnanolone</a></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a></li> <li><a href="/wiki/Pregnenolone_16%CE%B1-carbonitrile" title="Pregnenolone 16α-carbonitrile">Pregnenolone 16α-carbonitrile</a></li> <li><a href="/wiki/Proadifen" title="Proadifen">Proadifen</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Quingestrone" title="Quingestrone">Quingestrone</a></li> <li><a href="/wiki/Reserpine" title="Reserpine">Reserpine</a></li> <li><a href="/wiki/Reverse_triiodothyronine" title="Reverse triiodothyronine">Reverse triiodothyronine</a></li> <li><a href="/wiki/Rifampicin" title="Rifampicin">Rifampicin</a></li> <li><a href="/wiki/Rifaximin" title="Rifaximin">Rifaximin</a></li> <li><a href="/wiki/Rimexolone" title="Rimexolone">Rimexolone</a></li> <li><a href="/wiki/Riodipine" title="Riodipine">Riodipine</a></li> <li><a href="/wiki/Ritonavir" title="Ritonavir">Ritonavir</a></li> <li><a href="/wiki/Simvastatin" title="Simvastatin">Simvastatin</a></li> <li><a href="/wiki/Sirolimus" title="Sirolimus">Sirolimus</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/wiki/Spiroxatrine" title="Spiroxatrine">Spiroxatrine</a></li> <li><a href="/w/index.php?title=SR-12813&action=edit&redlink=1" class="new" title="SR-12813 (page does not exist)">SR-12813</a></li> <li><a href="/w/index.php?title=Suberoylanilide&action=edit&redlink=1" class="new" title="Suberoylanilide (page does not exist)">Suberoylanilide</a></li> <li><a href="/wiki/Sulfisoxazole" class="mw-redirect" title="Sulfisoxazole">Sulfisoxazole</a></li> <li><a href="/wiki/Suramin" title="Suramin">Suramin</a></li> <li><a href="/wiki/Tacrolimus" title="Tacrolimus">Tacrolimus</a></li> <li><a href="/w/index.php?title=Tenylidone&action=edit&redlink=1" class="new" title="Tenylidone (page does not exist)">Tenylidone</a></li> <li><a href="/wiki/Terconazole" title="Terconazole">Terconazole</a></li> <li><a href="/wiki/Testosterone_isocaproate" title="Testosterone isocaproate">Testosterone isocaproate</a></li> <li><a href="/wiki/Tetracycline" title="Tetracycline">Tetracycline</a></li> <li><a href="/wiki/Thiamylal_sodium" class="mw-redirect" title="Thiamylal sodium">Thiamylal sodium</a></li> <li><a href="/wiki/Thiothixene" class="mw-redirect" title="Thiothixene">Thiothixene</a></li> <li><a href="/wiki/Thonzonium_bromide" title="Thonzonium bromide">Thonzonium bromide</a></li> <li><a href="/wiki/Tianeptine" title="Tianeptine">Tianeptine</a></li> <li><a href="/wiki/Troglitazone" title="Troglitazone">Troglitazone</a></li> <li><a href="/wiki/Troleandomycin" title="Troleandomycin">Troleandomycin</a></li> <li><a href="/w/index.php?title=Tropanyl_3,5-dimethulbenzoate&action=edit&redlink=1" class="new" title="Tropanyl 3,5-dimethulbenzoate (page does not exist)">Tropanyl 3,5-dimethulbenzoate</a></li> <li><a href="/wiki/Zafirlukast" title="Zafirlukast">Zafirlukast</a></li> <li><a href="/wiki/Zeranol" title="Zeranol">Zeranol</a></li></ul> <ul><li>Antagonists: <a href="/wiki/Ketoconazole" title="Ketoconazole">Ketoconazole</a></li> <li><a href="/wiki/Sesamin" title="Sesamin">Sesamin</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd></dl> </div></td></tr></tbody></table></div> <style data-mw-deduplicate="TemplateStyles:r1130092004">.mw-parser-output .portal-bar{font-size:88%;font-weight:bold;display:flex;justify-content:center;align-items:baseline}.mw-parser-output .portal-bar-bordered{padding:0 2em;background-color:#fdfdfd;border:1px solid #a2a9b1;clear:both;margin:1em auto 0}.mw-parser-output .portal-bar-related{font-size:100%;justify-content:flex-start}.mw-parser-output .portal-bar-unbordered{padding:0 1.7em;margin-left:0}.mw-parser-output .portal-bar-header{margin:0 1em 0 0.5em;flex:0 0 auto;min-height:24px}.mw-parser-output .portal-bar-content{display:flex;flex-flow:row wrap;flex:0 1 auto;padding:0.15em 0;column-gap:1em;align-items:baseline;margin:0;list-style:none}.mw-parser-output .portal-bar-content-related{margin:0;list-style:none}.mw-parser-output .portal-bar-item{display:inline-block;margin:0.15em 0.2em;min-height:24px;line-height:24px}@media screen and (max-width:768px){.mw-parser-output .portal-bar{font-size:88%;font-weight:bold;display:flex;flex-flow:column wrap;align-items:baseline}.mw-parser-output .portal-bar-header{text-align:center;flex:0;padding-left:0.5em;margin:0 auto}.mw-parser-output .portal-bar-related{font-size:100%;align-items:flex-start}.mw-parser-output .portal-bar-content{display:flex;flex-flow:row wrap;align-items:center;flex:0;column-gap:1em;border-top:1px solid #a2a9b1;margin:0 auto;list-style:none}.mw-parser-output .portal-bar-content-related{border-top:none;margin:0;list-style:none}}.mw-parser-output .navbox+link+.portal-bar,.mw-parser-output .navbox+style+.portal-bar,.mw-parser-output .navbox+link+.portal-bar-bordered,.mw-parser-output .navbox+style+.portal-bar-bordered,.mw-parser-output .sister-bar+link+.portal-bar,.mw-parser-output .sister-bar+style+.portal-bar,.mw-parser-output .portal-bar+.navbox-styles+.navbox,.mw-parser-output .portal-bar+.navbox-styles+.sister-bar{margin-top:-1px}</style><div class="portal-bar noprint metadata noviewer portal-bar-bordered" role="navigation" aria-label="Portals"><a href="/wiki/Wikipedia:Contents/Portals" title="Wikipedia:Contents/Portals">Portal</a>:<ul class="portal-bar-content"><li class="portal-bar-item"><img alt="icon" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/WHO_Rod.svg/8px-WHO_Rod.svg.png" decoding="async" width="8" height="19" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/WHO_Rod.svg/12px-WHO_Rod.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d6/WHO_Rod.svg/16px-WHO_Rod.svg.png 2x" data-file-width="107" data-file-height="250" /> <a href="/wiki/Portal:Medicine" title="Portal:Medicine">Medicine</a></li></ul></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style></div><div role="navigation" class="navbox authority-control" aria-label="Navbox" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Help:Authority_control" title="Help:Authority control">Authority control databases</a>: National <a href="https://www.wikidata.org/wiki/Q415563#identifiers" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"><ul><li><a rel="nofollow" class="external text" href="https://aleph.nkp.cz/F/?func=find-c&local_base=aut&ccl_term=ica=ph376371&CON_LNG=ENG">Czech Republic</a></li></ul></div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Ethinylestradiol&oldid=1257041108">https://en.wikipedia.org/w/index.php?title=Ethinylestradiol&oldid=1257041108</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:CYP1A2_inhibitors" title="Category:CYP1A2 inhibitors">CYP1A2 inhibitors</a></li><li><a href="/wiki/Category:Ethynyl_compounds" title="Category:Ethynyl compounds">Ethynyl compounds</a></li><li><a href="/wiki/Category:Antigonadotropins" title="Category:Antigonadotropins">Antigonadotropins</a></li><li><a href="/wiki/Category:Estranes" title="Category:Estranes">Estranes</a></li><li><a href="/wiki/Category:GPER_agonists" title="Category:GPER agonists">GPER agonists</a></li><li><a href="/wiki/Category:Hepatotoxins" title="Category:Hepatotoxins">Hepatotoxins</a></li><li><a href="/wiki/Category:Hormonal_antineoplastic_drugs" title="Category:Hormonal antineoplastic drugs">Hormonal antineoplastic drugs</a></li><li><a href="/wiki/Category:Hormonal_contraception" title="Category:Hormonal contraception">Hormonal contraception</a></li><li><a href="/wiki/Category:Human_drug_metabolites" title="Category:Human drug metabolites">Human drug metabolites</a></li><li><a href="/wiki/Category:Prolactin_releasers" title="Category:Prolactin releasers">Prolactin releasers</a></li><li><a href="/wiki/Category:Hydroxyarenes" title="Category:Hydroxyarenes">Hydroxyarenes</a></li><li><a href="/wiki/Category:Synthetic_estrogens" title="Category:Synthetic estrogens">Synthetic estrogens</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Hidden categories: <ul><li><a href="/wiki/Category:All_articles_with_dead_external_links" title="Category:All articles with dead external links">All articles with dead external links</a></li><li><a href="/wiki/Category:Articles_with_dead_external_links_from_July_2022" title="Category:Articles with dead external links from July 2022">Articles with dead external links from July 2022</a></li><li><a href="/wiki/Category:CS1:_long_volume_value" title="Category:CS1: long volume value">CS1: long volume value</a></li><li><a href="/wiki/Category:CS1_German-language_sources_(de)" title="Category:CS1 German-language sources (de)">CS1 German-language sources (de)</a></li><li><a href="/wiki/Category:CS1_maint:_DOI_inactive_as_of_November_2024" title="Category:CS1 maint: DOI inactive as of November 2024">CS1 maint: DOI inactive as of November 2024</a></li><li><a href="/wiki/Category:CS1_French-language_sources_(fr)" title="Category:CS1 French-language sources (fr)">CS1 French-language sources (fr)</a></li><li><a href="/wiki/Category:Articles_with_short_description" title="Category:Articles with short description">Articles with short description</a></li><li><a href="/wiki/Category:Short_description_is_different_from_Wikidata" title="Category:Short description is different from Wikidata">Short description is different from Wikidata</a></li><li><a href="/wiki/Category:Use_dmy_dates_from_March_2024" title="Category:Use dmy dates from March 2024">Use dmy dates from March 2024</a></li><li><a href="/wiki/Category:Drugs_with_non-standard_legal_status" title="Category:Drugs with non-standard legal status">Drugs with non-standard legal status</a></li><li><a href="/wiki/Category:ECHA_InfoCard_ID_from_Wikidata" title="Category:ECHA InfoCard ID from Wikidata">ECHA InfoCard ID from Wikidata</a></li><li><a href="/wiki/Category:All_articles_with_unsourced_statements" title="Category:All articles with unsourced statements">All articles with unsourced statements</a></li><li><a href="/wiki/Category:Articles_with_unsourced_statements_from_July_2018" title="Category:Articles with unsourced statements from July 2018">Articles with unsourced statements from July 2018</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 12 November 2024, at 22:44 (UTC).</li> <li id="footer-info-copyright">Text is available under the <a href="/wiki/Wikipedia:Text_of_the_Creative_Commons_Attribution-ShareAlike_4.0_International_License" title="Wikipedia:Text of the Creative Commons Attribution-ShareAlike 4.0 International License">Creative Commons Attribution-ShareAlike 4.0 License</a>; additional terms may apply. By using this site, you agree to the <a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Terms_of_Use" class="extiw" title="foundation:Special:MyLanguage/Policy:Terms of Use">Terms of Use</a> and <a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Privacy_policy" class="extiw" title="foundation:Special:MyLanguage/Policy:Privacy policy">Privacy Policy</a>. Wikipedia® is a registered trademark of the <a rel="nofollow" class="external text" href="https://wikimediafoundation.org/">Wikimedia Foundation, Inc.</a>, a non-profit organization.</li> </ul> <ul id="footer-places"> <li id="footer-places-privacy"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Privacy_policy">Privacy policy</a></li> <li id="footer-places-about"><a href="/wiki/Wikipedia:About">About Wikipedia</a></li> <li id="footer-places-disclaimers"><a href="/wiki/Wikipedia:General_disclaimer">Disclaimers</a></li> <li id="footer-places-contact"><a href="//en.wikipedia.org/wiki/Wikipedia:Contact_us">Contact Wikipedia</a></li> <li id="footer-places-wm-codeofconduct"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Universal_Code_of_Conduct">Code of Conduct</a></li> <li id="footer-places-developers"><a href="https://developer.wikimedia.org">Developers</a></li> <li id="footer-places-statslink"><a href="https://stats.wikimedia.org/#/en.wikipedia.org">Statistics</a></li> <li id="footer-places-cookiestatement"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Cookie_statement">Cookie statement</a></li> <li id="footer-places-mobileview"><a href="//en.m.wikipedia.org/w/index.php?title=Ethinylestradiol&mobileaction=toggle_view_mobile" class="noprint stopMobileRedirectToggle">Mobile view</a></li> </ul> <ul id="footer-icons" class="noprint"> <li id="footer-copyrightico"><a href="https://wikimediafoundation.org/" class="cdx-button cdx-button--fake-button cdx-button--size-large cdx-button--fake-button--enabled"><img src="/static/images/footer/wikimedia-button.svg" width="84" height="29" alt="Wikimedia Foundation" loading="lazy"></a></li> <li id="footer-poweredbyico"><a href="https://www.mediawiki.org/" class="cdx-button cdx-button--fake-button cdx-button--size-large cdx-button--fake-button--enabled"><img src="/w/resources/assets/poweredby_mediawiki.svg" alt="Powered by MediaWiki" width="88" height="31" loading="lazy"></a></li> </ul> </footer> </div> </div> </div> <div class="vector-settings" id="p-dock-bottom"> <ul></ul> </div><script>(RLQ=window.RLQ||[]).push(function(){mw.config.set({"wgHostname":"mw-web.codfw.main-6df7948d6c-vbrch","wgBackendResponseTime":203,"wgPageParseReport":{"limitreport":{"cputime":"2.628","walltime":"3.132","ppvisitednodes":{"value":23307,"limit":1000000},"postexpandincludesize":{"value":719766,"limit":2097152},"templateargumentsize":{"value":29859,"limit":2097152},"expansiondepth":{"value":19,"limit":100},"expensivefunctioncount":{"value":8,"limit":500},"unstrip-depth":{"value":1,"limit":20},"unstrip-size":{"value":803918,"limit":5000000},"entityaccesscount":{"value":1,"limit":400},"timingprofile":["100.00% 2568.304 1 -total"," 34.56% 887.656 3 Template:Reflist"," 26.11% 670.494 201 Template:No_selflink"," 22.02% 565.482 1 Template:Affinities_of_estrogen_receptor_ligands_for_the_ERα_and_ERβ"," 13.96% 358.433 88 Template:Cite_journal"," 13.49% 346.471 72 Template:Cite_book"," 12.20% 313.378 1 Template:Drugbox"," 10.00% 256.957 1 Template:Infobox"," 5.78% 148.500 1 Template:Risk_of_venous_thromboembolism_with_hormone_therapy_and_birth_control_pills_(QResearch/CPRD)"," 3.06% 78.544 1 Template:Relative_affinities_of_estrogens_for_steroid_hormone_receptors_and_blood_proteins"]},"scribunto":{"limitreport-timeusage":{"value":"1.375","limit":"10.000"},"limitreport-memusage":{"value":10506540,"limit":52428800},"limitreport-profile":[["MediaWiki\\Extension\\Scribunto\\Engines\\LuaSandbox\\LuaSandboxCallback::redirectTarget","220","15.5"],["?","180","12.7"],["MediaWiki\\Extension\\Scribunto\\Engines\\LuaSandbox\\LuaSandboxCallback::callParserFunction","180","12.7"],["recursiveClone \u003CmwInit.lua:45\u003E","100","7.0"],["MediaWiki\\Extension\\Scribunto\\Engines\\LuaSandbox\\LuaSandboxCallback::find","100","7.0"],["MediaWiki\\Extension\\Scribunto\\Engines\\LuaSandbox\\LuaSandboxCallback::getExpandedArgument","80","5.6"],["date","60","4.2"],["dataWrapper \u003Cmw.lua:672\u003E","60","4.2"],["MediaWiki\\Extension\\Scribunto\\Engines\\LuaSandbox\\LuaSandboxCallback::gsub","40","2.8"],["MediaWiki\\Extension\\Scribunto\\Engines\\LuaSandbox\\LuaSandboxCallback::preprocess","40","2.8"],["[others]","360","25.4"]]},"cachereport":{"origin":"mw-web.codfw.main-5cd4cd96d5-98kkn","timestamp":"20241127080418","ttl":2592000,"transientcontent":false}}});});</script> <script type="application/ld+json">{"@context":"https:\/\/schema.org","@type":"Article","name":"Ethinylestradiol","url":"https:\/\/en.wikipedia.org\/wiki\/Ethinylestradiol","sameAs":"http:\/\/www.wikidata.org\/entity\/Q415563","mainEntity":"http:\/\/www.wikidata.org\/entity\/Q415563","author":{"@type":"Organization","name":"Contributors to Wikimedia projects"},"publisher":{"@type":"Organization","name":"Wikimedia Foundation, Inc.","logo":{"@type":"ImageObject","url":"https:\/\/www.wikimedia.org\/static\/images\/wmf-hor-googpub.png"}},"datePublished":"2005-08-10T14:53:05Z","dateModified":"2024-11-12T22:44:42Z","image":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/6\/6d\/Ethinylestradiol.svg","headline":"estrogen medication used widely in birth control pills in combination with progestins"}</script> </body> </html>