CINXE.COM

<!DOCTYPE html> <html class="client-nojs vector-feature-language-in-header-enabled vector-feature-language-in-main-page-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-sticky-header-enabled vector-toc-available" lang="en" dir="ltr"> <head> <meta charset="UTF-8"> <title>Estriol - Wikipedia</title> <script>(function(){var className="client-js vector-feature-language-in-header-enabled vector-feature-language-in-main-page-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-sticky-header-enabled 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":"ca1019c3-ae65-4b0c-bd44-d476f9d80908","wgCanonicalNamespace":"","wgCanonicalSpecialPageName":false,"wgNamespaceNumber":0,"wgPageName":"Estriol","wgTitle":"Estriol","wgCurRevisionId":1267297848,"wgRevisionId":1267297848,"wgArticleId":647360,"wgIsArticle":true,"wgIsRedirect":false,"wgAction":"view","wgUserName":null,"wgUserGroups":["*"],"wgCategories":["All articles with dead external links","Articles with dead external links from March 2024","Articles with permanently dead external links","ECHA InfoCard ID from Wikidata","Articles containing unverified chemical infoboxes","Chembox image size set","Articles with short description","Short description matches Wikidata","All articles with unsourced statements","Articles with unsourced statements from October 2016","Estranes","Estrogens","GPER antagonists","Hormones of the hypothalamus-pituitary-gonad axis","Hormones of the pregnant female","Hydroxyarenes","Sex hormones","Triols"],"wgPageViewLanguage":"en","wgPageContentLanguage":"en","wgPageContentModel":"wikitext","wgRelevantPageName":"Estriol","wgRelevantArticleId":647360,"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":20000,"wgEditSubmitButtonLabelPublish":true,"wgULSPosition":"interlanguage","wgULSisCompactLinksEnabled":false,"wgVector2022LanguageInHeader":true,"wgULSisLanguageSelectorEmpty":false,"wgWikibaseItemId":"Q409721","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"};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.growthExperiments.SuggestedEditSession"];</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.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.20"> <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/8/82/Estriol.svg/1200px-Estriol.svg.png"> <meta property="og:image:width" content="1200"> <meta property="og:image:height" content="654"> <meta property="og:image" content="https://upload.wikimedia.org/wikipedia/commons/thumb/8/82/Estriol.svg/800px-Estriol.svg.png"> <meta property="og:image:width" content="800"> <meta property="og:image:height" content="436"> <meta property="og:image" content="https://upload.wikimedia.org/wikipedia/commons/thumb/8/82/Estriol.svg/640px-Estriol.svg.png"> <meta property="og:image:width" content="640"> <meta property="og:image:height" content="349"> <meta name="viewport" content="width=1120"> <meta property="og:title" content="Estriol - 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/Estriol"> <link rel="alternate" type="application/x-wiki" title="Edit this page" href="/w/index.php?title=Estriol&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/Estriol"> <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-Estriol rootpage-Estriol 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" title="Main menu" > <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" ><span class="vector-icon mw-ui-icon-menu mw-ui-icon-wikimedia-menu"></span> <span class="vector-dropdown-label-text">Main menu</span> </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"><span>Main page</span></a></li><li id="n-contents" class="mw-list-item"><a href="/wiki/Wikipedia:Contents" title="Guides to browsing Wikipedia"><span>Contents</span></a></li><li id="n-currentevents" class="mw-list-item"><a href="/wiki/Portal:Current_events" title="Articles related to current events"><span>Current events</span></a></li><li id="n-randompage" class="mw-list-item"><a href="/wiki/Special:Random" title="Visit a randomly selected article [x]" accesskey="x"><span>Random article</span></a></li><li id="n-aboutsite" class="mw-list-item"><a href="/wiki/Wikipedia:About" title="Learn about Wikipedia and how it works"><span>About Wikipedia</span></a></li><li id="n-contactpage" class="mw-list-item"><a href="//en.wikipedia.org/wiki/Wikipedia:Contact_us" title="How to contact Wikipedia"><span>Contact us</span></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"><span>Help</span></a></li><li id="n-introduction" class="mw-list-item"><a href="/wiki/Help:Introduction" title="Learn how to edit Wikipedia"><span>Learn to edit</span></a></li><li id="n-portal" class="mw-list-item"><a href="/wiki/Wikipedia:Community_portal" title="The hub for editors"><span>Community portal</span></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"><span>Recent changes</span></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"><span>Upload file</span></a></li><li id="n-specialpages" class="mw-list-item"><a href="/wiki/Special:SpecialPages"><span>Special pages</span></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"> <span class="mw-logo-container skin-invert"> <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;"> </span> </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"><span class="vector-icon mw-ui-icon-search mw-ui-icon-wikimedia-search"></span> <span>Search</span> </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" > <span class="cdx-text-input__icon cdx-text-input__start-icon"></span> </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" ><span class="vector-icon mw-ui-icon-appearance mw-ui-icon-wikimedia-appearance"></span> <span class="vector-dropdown-label-text">Appearance</span> </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/?wmf_source=donate&wmf_medium=sidebar&wmf_campaign=en.wikipedia.org&uselang=en" class=""><span>Donate</span></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=Estriol" title="You are encouraged to create an account and log in; however, it is not mandatory" class=""><span>Create account</span></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=Estriol" title="You're encouraged to log in; however, it's not mandatory. [o]" accesskey="o" class=""><span>Log in</span></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" ><span class="vector-icon mw-ui-icon-ellipsis mw-ui-icon-wikimedia-ellipsis"></span> <span class="vector-dropdown-label-text">Personal tools</span> </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/?wmf_source=donate&wmf_medium=sidebar&wmf_campaign=en.wikipedia.org&uselang=en"><span>Donate</span></a></li><li id="pt-createaccount" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Special:CreateAccount&returnto=Estriol" title="You are encouraged to create an account and log in; however, it is not mandatory"><span class="vector-icon mw-ui-icon-userAdd mw-ui-icon-wikimedia-userAdd"></span> <span>Create account</span></a></li><li id="pt-login" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Special:UserLogin&returnto=Estriol" title="You're encouraged to log in; however, it's not mandatory. [o]" accesskey="o"><span class="vector-icon mw-ui-icon-logIn mw-ui-icon-wikimedia-logIn"></span> <span>Log in</span></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"><span>learn more</span></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"><span>Contributions</span></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"><span>Talk</span></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-Biological_activity" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Biological_activity"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>Biological activity</span> </div> </a> <ul id="toc-Biological_activity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biochemistry" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Biochemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Biochemistry</span> </div> </a> <button aria-controls="toc-Biochemistry-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Biochemistry subsection</span> </button> <ul id="toc-Biochemistry-sublist" class="vector-toc-list"> <li id="toc-Biosynthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Biosynthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Biosynthesis</span> </div> </a> <ul id="toc-Biosynthesis-sublist" class="vector-toc-list"> <li id="toc-In_non-pregnant_women" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#In_non-pregnant_women"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1.1</span> <span>In non-pregnant women</span> </div> </a> <ul id="toc-In_non-pregnant_women-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-In_pregnant_women" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#In_pregnant_women"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1.2</span> <span>In pregnant women</span> </div> </a> <ul id="toc-In_pregnant_women-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Distribution" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Distribution"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>Distribution</span> </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-2"> <a class="vector-toc-link" href="#Metabolism"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Metabolism</span> </div> </a> <ul id="toc-Metabolism-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Excretion" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Excretion"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.4</span> <span>Excretion</span> </div> </a> <ul id="toc-Excretion-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Medical_use" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Medical_use"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Medical use</span> </div> </a> <ul id="toc-Medical_use-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Chemistry" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Chemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Chemistry</span> </div> </a> <ul id="toc-Chemistry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>History</span> </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Use_in_screening" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Use_in_screening"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Use in screening</span> </div> </a> <ul id="toc-Use_in_screening-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>References</span> </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 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Further_reading"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Further reading</span> </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" title="Table of Contents" > <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" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </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"><span class="mw-page-title-main">Estriol</span></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 26 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-26" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">26 languages</span> </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%D8%B3%D8%AA%D8%B1%D9%8A%D9%88%D9%84" title="إستريول – Arabic" lang="ar" hreflang="ar" data-title="إستريول" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A7%D8%B3%D8%AA%D8%B1%DB%8C%D9%88%D9%84" title="استریول – South Azerbaijani" lang="azb" hreflang="azb" data-title="استریول" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Estriol" title="Estriol – Bosnian" lang="bs" hreflang="bs" data-title="Estriol" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Estriol" title="Estriol – Catalan" lang="ca" hreflang="ca" data-title="Estriol" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Estriol" title="Estriol – Czech" lang="cs" hreflang="cs" data-title="Estriol" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Estriol" title="Estriol – German" lang="de" hreflang="de" data-title="Estriol" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Estriol" title="Estriol – Spanish" lang="es" hreflang="es" data-title="Estriol" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Estriol" title="Estriol – Basque" lang="eu" hreflang="eu" data-title="Estriol" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%D8%B3%D8%AA%D8%B1%DB%8C%D9%88%D9%84" title="استریول – Persian" lang="fa" hreflang="fa" data-title="استریول" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Estriol" title="Estriol – French" lang="fr" hreflang="fr" data-title="Estriol" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Estriol" title="Estriol – Galician" lang="gl" hreflang="gl" data-title="Estriol" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Estriolo" title="Estriolo – Italian" lang="it" hreflang="it" data-title="Estriolo" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%90%D7%A1%D7%98%D7%A8%D7%99%D7%95%D7%9C" title="אסטריול – Hebrew" lang="he" hreflang="he" data-title="אסטריול" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/%C3%96sztriol" title="Ösztriol – Hungarian" lang="hu" hreflang="hu" data-title="Ösztriol" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Oestriol" title="Oestriol – Dutch" lang="nl" hreflang="nl" data-title="Oestriol" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A8%E3%82%B9%E3%83%88%E3%83%AA%E3%82%AA%E3%83%BC%E3%83%AB" title="エストリオール – Japanese" lang="ja" hreflang="ja" data-title="エストリオール" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Estriol" title="Estriol – Polish" lang="pl" hreflang="pl" data-title="Estriol" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Estriol" title="Estriol – Portuguese" lang="pt" hreflang="pt" data-title="Estriol" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%AD%D1%81%D1%82%D1%80%D0%B8%D0%BE%D0%BB" title="Эстриол – Russian" lang="ru" hreflang="ru" data-title="Эстриол" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Estriol" title="Estriol – Slovak" lang="sk" hreflang="sk" data-title="Estriol" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Estriol" title="Estriol – Serbian" lang="sr" hreflang="sr" data-title="Estriol" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Estriol" title="Estriol – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Estriol" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Estrioli" title="Estrioli – Finnish" lang="fi" hreflang="fi" data-title="Estrioli" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/%C3%96striol" title="Östriol – Swedish" lang="sv" hreflang="sv" data-title="Östriol" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/%C3%96striol" title="Östriol – Turkish" lang="tr" hreflang="tr" data-title="Östriol" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E9%9B%8C%E4%B8%89%E9%86%87" title="雌三醇 – Chinese" lang="zh" hreflang="zh" data-title="雌三醇" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q409721#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></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/Estriol" title="View the content page [c]" accesskey="c"><span>Article</span></a></li><li id="ca-talk" class="vector-tab-noicon mw-list-item"><a href="/wiki/Talk:Estriol" rel="discussion" title="Discuss improvements to the content page [t]" accesskey="t"><span>Talk</span></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" ><span class="vector-dropdown-label-text">English</span> </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/Estriol"><span>Read</span></a></li><li id="ca-edit" class="vector-tab-noicon mw-list-item"><a href="/w/index.php?title=Estriol&action=edit" title="Edit this page [e]" accesskey="e"><span>Edit</span></a></li><li id="ca-history" class="vector-tab-noicon mw-list-item"><a href="/w/index.php?title=Estriol&action=history" title="Past revisions of this page [h]" accesskey="h"><span>View history</span></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" ><span class="vector-dropdown-label-text">Tools</span> </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/Estriol"><span>Read</span></a></li><li id="ca-more-edit" class="vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Estriol&action=edit" title="Edit this page [e]" accesskey="e"><span>Edit</span></a></li><li id="ca-more-history" class="vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Estriol&action=history"><span>View history</span></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/Estriol" title="List of all English Wikipedia pages containing links to this page [j]" accesskey="j"><span>What links here</span></a></li><li id="t-recentchangeslinked" class="mw-list-item"><a href="/wiki/Special:RecentChangesLinked/Estriol" rel="nofollow" title="Recent changes in pages linked from this page [k]" accesskey="k"><span>Related changes</span></a></li><li id="t-upload" class="mw-list-item"><a href="//en.wikipedia.org/wiki/Wikipedia:File_Upload_Wizard" title="Upload files [u]" accesskey="u"><span>Upload file</span></a></li><li id="t-permalink" class="mw-list-item"><a href="/w/index.php?title=Estriol&oldid=1267297848" title="Permanent link to this revision of this page"><span>Permanent link</span></a></li><li id="t-info" class="mw-list-item"><a href="/w/index.php?title=Estriol&action=info" title="More information about this page"><span>Page information</span></a></li><li id="t-cite" class="mw-list-item"><a href="/w/index.php?title=Special:CiteThisPage&page=Estriol&id=1267297848&wpFormIdentifier=titleform" title="Information on how to cite this page"><span>Cite this page</span></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%2FEstriol"><span>Get shortened URL</span></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%2FEstriol"><span>Download QR code</span></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=Estriol&action=show-download-screen" title="Download this page as a PDF file"><span>Download as PDF</span></a></li><li id="t-print" class="mw-list-item"><a href="/w/index.php?title=Estriol&printable=yes" title="Printable version of this page [p]" accesskey="p"><span>Printable version</span></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:Estriol" hreflang="en"><span>Wikimedia Commons</span></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/Q409721" title="Structured data on this page hosted by Wikidata [g]" accesskey="g"><span>Wikidata item</span></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"><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">This article is about estriol as a hormone. For its use as a medication, see <a href="/wiki/Estriol_(medication)" title="Estriol (medication)">Estriol (medication)</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1268415487">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> <table class="infobox ib-chembox"> <caption>Estriol </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center skin-invert" typeof="mw:File"><a href="/wiki/File:Estriol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/82/Estriol.svg/250px-Estriol.svg.png" decoding="async" width="250" height="136" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/82/Estriol.svg/500px-Estriol.svg.png 1.5x" data-file-width="512" data-file-height="279" /></a><figcaption></figcaption></figure> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Estriol_molecule_ball.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/43/Estriol_molecule_ball.png/235px-Estriol_molecule_ball.png" decoding="async" width="235" height="151" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/43/Estriol_molecule_ball.png/353px-Estriol_molecule_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/43/Estriol_molecule_ball.png/470px-Estriol_molecule_ball.png 2x" data-file-width="2560" data-file-height="1646" /></a><figcaption></figcaption></figure> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Estra-1,3,5(10)-triene-3,16α,17β-triol</div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">(1<i>R</i>,2<i>R</i>,3a<i>S</i>,3b<i>R</i>,9b<i>S</i>,11a<i>S</i>)-11a-Methyl-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1<i>H</i>-cyclopenta[<i>a</i>]phenanthrene-1,2,7-triol</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Oestriol; E3; Estratriol; Theelol; Trihydroxyestrin; Trihydroxyoestrin; 16α-Hydroxyestradiol</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><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><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=50-27-1">50-27-1</a></span></li><li>1306-04-3</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=C%5BC%40%5D12CC%5BC%40H%5D3%5BC%40H%5D%28%5BC%40%40H%5D1C%5BC%40H%5D%28%5BC%40%40H%5D2O%29O%29CCC4%3DC3C%3DCC%28%3DC4%29O">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=27974">CHEBI:27974</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL193482">ChEMBL193482</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.5553.html">5553</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.021">100.000.021</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q409721#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></span> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C05141">C05141</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/5756">5756</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/FB33469R8E">FB33469R8E</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID9022366">DTXSID9022366</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q409721#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></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><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="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,17+,18+/m1/s1</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: PROQIPRRNZUXQM-ZXXIGWHRSA-N</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><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="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H]([C@@H]2O)O)CCC4=C3C=CC(=C4)O</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>18</sub><span title="Hydrogen">H</span><sub>24</sub><span title="Oxygen">O</span><sub>3</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>288.387 g/mol    </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Estriol</b> (<b>E3</b>), also spelled <b>oestriol</b>, is a <a href="/wiki/Steroid" title="Steroid">steroid</a>, a weak <a href="/wiki/Estrogen" title="Estrogen">estrogen</a>, and a minor female <a href="/wiki/Sex_hormone" title="Sex hormone">sex hormone</a>.<sup id="cite_ref-pmid16112947_1-0" class="reference"><a href="#cite_note-pmid16112947-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Puri2005_2-0" class="reference"><a href="#cite_note-Puri2005-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> It is one of three major <a href="/wiki/Endogenous" class="mw-redirect" title="Endogenous">endogenous</a> estrogens, the others being <a href="/wiki/Estradiol" title="Estradiol">estradiol</a> and <a href="/wiki/Estrone" title="Estrone">estrone</a>.<sup id="cite_ref-pmid16112947_1-1" class="reference"><a href="#cite_note-pmid16112947-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Levels of estriol in women who are not <a href="/wiki/Pregnancy" title="Pregnancy">pregnant</a> are almost undetectable.<sup id="cite_ref-IIIBarbieri2013_3-0" class="reference"><a href="#cite_note-IIIBarbieri2013-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> However, during pregnancy, estriol is synthesized in very high quantities by the <a href="/wiki/Placenta" title="Placenta">placenta</a> and is the most produced estrogen in the body by far,<sup id="cite_ref-IIIBarbieri2013_3-1" class="reference"><a href="#cite_note-IIIBarbieri2013-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Goodman2003_4-0" class="reference"><a href="#cite_note-Goodman2003-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> although circulating levels of estriol are similar to those of other estrogens due to a relatively high rate of <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> and <a href="/wiki/Excretion" title="Excretion">excretion</a>.<sup id="cite_ref-Goodman2003_4-1" class="reference"><a href="#cite_note-Goodman2003-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-(Prof.)2001_5-0" class="reference"><a href="#cite_note-(Prof.)2001-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Relative to estradiol, both estriol and estrone have far weaker activity as estrogens.<sup id="cite_ref-pmid16112947_1-2" class="reference"><a href="#cite_note-pmid16112947-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p>In addition to its role as a natural hormone, estriol is used as a <a href="/wiki/Medication" title="Medication">medication</a>, for instance in <a href="/wiki/Menopausal_hormone_therapy" class="mw-redirect" title="Menopausal hormone therapy">menopausal hormone therapy</a>; for information on estriol as a medication, see the <a href="/wiki/Estriol_(medication)" title="Estriol (medication)">estriol (medication)</a> article. </p> <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="Biological_activity">Biological activity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estriol&action=edit&section=1" title="Edit section: Biological activity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Estriol is an estrogen, specifically an <a href="/wiki/Agonist" title="Agonist">agonist</a> of the <a href="/wiki/Estrogen_receptor" title="Estrogen receptor">estrogen receptors</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>.<sup id="cite_ref-pmid16112947_1-3" class="reference"><a href="#cite_note-pmid16112947-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-JaouenSalmain2015_6-0" class="reference"><a href="#cite_note-JaouenSalmain2015-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid16554039_7-0" class="reference"><a href="#cite_note-pmid16554039-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> It is a far less <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potent</a> estrogen than is estradiol, and as such is a relatively weak estrogen.<sup id="cite_ref-pmid16112947_1-4" class="reference"><a href="#cite_note-pmid16112947-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid16554039_7-1" class="reference"><a href="#cite_note-pmid16554039-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-LappanoRosano2010_8-0" class="reference"><a href="#cite_note-LappanoRosano2010-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Becker2001_9-0" class="reference"><a href="#cite_note-Becker2001-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> According to one <i><a href="/wiki/In_vitro" title="In vitro">in vitro</a></i> study, the <a href="/wiki/Relative_binding_affinity" class="mw-redirect" title="Relative binding affinity">relative binding affinity</a> (RBA) of estriol for the human ERα and ERβ was 11.3% and 17.6% of that estradiol, respectively, and the <a href="/wiki/Relative_transactivational_capacity" class="mw-redirect" title="Relative transactivational capacity">relative transactivational capacity</a> of estriol at the ERα and ERβ was 10.6% and 16.6% of that of estradiol, respectively.<sup id="cite_ref-pmid16554039_7-2" class="reference"><a href="#cite_note-pmid16554039-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> According to another <i>in vitro</i> study however, the RBA of estriol for the ERα and ERβ were 14% and 21% of those of estradiol, respectively,<sup id="cite_ref-RubanyiKauffman2003_10-0" class="reference"><a href="#cite_note-RubanyiKauffman2003-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> suggesting that unlike estradiol and estrone, estriol may have preferential <a href="/wiki/Affinity_(pharmacology)" class="mw-redirect" title="Affinity (pharmacology)">affinity</a> for ERβ.<sup id="cite_ref-JaouenSalmain2015_6-1" class="reference"><a href="#cite_note-JaouenSalmain2015-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Although estriol is an <a href="/wiki/Efficacy" title="Efficacy">efficacious</a> agonist of the ERs, it is reported to have mixed <a href="/wiki/Agonist%E2%80%93antagonist" class="mw-redirect" title="Agonist–antagonist">agonist–antagonist</a> (<a href="/wiki/Partial_agonist" title="Partial agonist">partial agonist</a>) activity at the ER; on its own, it is weakly estrogenic, but in the presence of estradiol, it is <a href="/wiki/Antiestrogen" title="Antiestrogen">antiestrogenic</a>.<sup id="cite_ref-LappanoRosano2010_8-1" class="reference"><a href="#cite_note-LappanoRosano2010-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Becker2001_9-1" class="reference"><a href="#cite_note-Becker2001-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Given by <a href="/wiki/Subcutaneous_injection" class="mw-redirect" title="Subcutaneous injection">subcutaneous injection</a> in mice, estradiol is about 10-fold more potent than estrone and about 100-fold more potent than estriol.<sup id="cite_ref-Labhart2012_11-0" class="reference"><a href="#cite_note-Labhart2012-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Blackburn2014_12-0" class="reference"><a href="#cite_note-Blackburn2014-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> It is notable that unlike estriol, estrone can be <a href="/wiki/Metabolism" title="Metabolism">metabolized</a> into estradiol, and most of its potency <i><a href="/wiki/In_vivo" title="In vivo">in vivo</a></i> is in fact actually due to conversion into estradiol.<sup id="cite_ref-pmid16112947_1-5" class="reference"><a href="#cite_note-pmid16112947-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p>In addition to acting as an agonist of the <a href="/wiki/Nuclear_receptor" title="Nuclear receptor">nuclear</a> ERs, estriol at high concentrations (~1,000–10,000 nM) also acts as an <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonist</a> of the <a href="/wiki/GPER" title="GPER">GPER</a>, a <a href="/wiki/Membrane_estrogen_receptor" title="Membrane estrogen receptor">membrane estrogen receptor</a> where, conversely, estradiol acts as an agonist.<sup id="cite_ref-pmid26023144_13-0" class="reference"><a href="#cite_note-pmid26023144-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-LappanoRosano2010_8-2" class="reference"><a href="#cite_note-LappanoRosano2010-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-JaouenSalmain2015_6-2" class="reference"><a href="#cite_note-JaouenSalmain2015-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-GirgertEmons2014_14-0" class="reference"><a href="#cite_note-GirgertEmons2014-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Estradiol increases <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a> cell growth via activation of the GPER (in addition to the ER), and estriol has been found to inhibit estradiol-induced proliferation of <a href="/wiki/Triple-negative_breast_cancer" title="Triple-negative breast cancer">triple-negative breast cancer</a> cells through blockade of the GPER.<sup id="cite_ref-GirgertEmons2014_14-1" class="reference"><a href="#cite_note-GirgertEmons2014-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable sortable mw-collapsible" style="text-align:left; margin-left:auto; margin-right:auto; border:none;"> <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:Selected_biological_properties_of_endogenous_estrogens_in_rats" title="Template:Selected biological properties of endogenous estrogens in rats"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Selected_biological_properties_of_endogenous_estrogens_in_rats" title="Template talk:Selected biological properties of endogenous estrogens in rats"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Selected_biological_properties_of_endogenous_estrogens_in_rats" title="Special:EditPage/Template:Selected biological properties of endogenous estrogens in rats"><abbr title="Edit this template">e</abbr></a></li></ul></div> Selected biological properties of endogenous estrogens in rats </caption> <tbody><tr> <th><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogen</a></th> <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</span> <a href="/wiki/Relative_binding_affinity" class="mw-redirect" title="Relative binding affinity"><abbr title="relative binding affinity">RBA</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 binding affinity</span> (%)</th> <th><a href="/wiki/Uterus" title="Uterus">Uterine weight</a> (%)</th> <th><a href="/wiki/Uterotrophy" class="mw-redirect" title="Uterotrophy">Uterotrophy</a></th> <th><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</span> levels (%)</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</span> <a href="/wiki/Relative_binding_affinity" class="mw-redirect" title="Relative binding affinity"><abbr title="relative binding affinity">RBA</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 binding affinity</span> (%) </th></tr> <tr> <td>Control</td> <td>–</td> <td>100</td> <td>–</td> <td>100</td> <td>– </td></tr> <tr> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol (E2)</a></td> <td>100</td> <td>506 ± 20</td> <td>+++</td> <td>12–19</td> <td>100 </td></tr> <tr> <td><a href="/wiki/Estrone_(medication)" title="Estrone (medication)">Estrone (E1)</a></td> <td>11 ± 8</td> <td>490 ± 22</td> <td>+++</td> <td>?</td> <td>20 </td></tr> <tr> <td><a href="/wiki/Estriol_(medication)" title="Estriol (medication)">Estriol (E3)</a></td> <td>10 ± 4</td> <td>468 ± 30</td> <td>+++</td> <td>8–18</td> <td>3 </td></tr> <tr> <td><a href="/wiki/Estetrol_(medication)" title="Estetrol (medication)">Estetrol (E4)</a></td> <td>0.5 ± 0.2</td> <td>?</td> <td>Inactive</td> <td>?</td> <td>1 </td></tr> <tr> <td><a href="/wiki/Alfatradiol" title="Alfatradiol">17α-Estradiol</a></td> <td>4.2 ± 0.8</td> <td>?</td> <td>?</td> <td>?</td> <td>? </td></tr> <tr> <td><a href="/wiki/2-Hydroxyestradiol" title="2-Hydroxyestradiol">2-Hydroxyestradiol</a></td> <td>24 ± 7</td> <td>285 ± 8</td> <td>+<sup>b</sup></td> <td>31–61</td> <td>28 </td></tr> <tr> <td><a href="/wiki/2-Methoxyestradiol" title="2-Methoxyestradiol">2-Methoxyestradiol</a></td> <td>0.05 ± 0.04</td> <td>101</td> <td>Inactive</td> <td>?</td> <td>130 </td></tr> <tr> <td><a href="/wiki/4-Hydroxyestradiol" title="4-Hydroxyestradiol">4-Hydroxyestradiol</a></td> <td>45 ± 12</td> <td>?</td> <td>?</td> <td>?</td> <td>? </td></tr> <tr> <td><a href="/wiki/4-Methoxyestradiol" title="4-Methoxyestradiol">4-Methoxyestradiol</a></td> <td>1.3 ± 0.2</td> <td>260</td> <td>++</td> <td>?</td> <td>9 </td></tr> <tr> <td><a href="/wiki/4-Fluoroestradiol" title="4-Fluoroestradiol">4-Fluoroestradiol</a><sup>a</sup></td> <td>180 ± 43</td> <td>?</td> <td>+++</td> <td>?</td> <td>? </td></tr> <tr> <td><a href="/wiki/2-Hydroxyestrone" title="2-Hydroxyestrone">2-Hydroxyestrone</a></td> <td>1.9 ± 0.8</td> <td>130 ± 9</td> <td>Inactive</td> <td>110–142</td> <td>8 </td></tr> <tr> <td><a href="/wiki/2-Methoxyestrone" title="2-Methoxyestrone">2-Methoxyestrone</a></td> <td>0.01 ± 0.00</td> <td>103 ± 7</td> <td>Inactive</td> <td>95–100</td> <td>120 </td></tr> <tr> <td><a href="/wiki/4-Hydroxyestrone" title="4-Hydroxyestrone">4-Hydroxyestrone</a></td> <td>11 ± 4</td> <td>351</td> <td>++</td> <td>21–50</td> <td>35 </td></tr> <tr> <td><a href="/wiki/4-Methoxyestrone" title="4-Methoxyestrone">4-Methoxyestrone</a></td> <td>0.13 ± 0.04</td> <td>338</td> <td>++</td> <td>65–92</td> <td>12 </td></tr> <tr> <td><a href="/wiki/16%CE%B1-Hydroxyestrone" title="16α-Hydroxyestrone">16α-Hydroxyestrone</a></td> <td>2.8 ± 1.0</td> <td>552 ± 42</td> <td>+++</td> <td>7–24</td> <td><0.5 </td></tr> <tr> <td><a href="/wiki/2-Hydroxyestriol" title="2-Hydroxyestriol">2-Hydroxyestriol</a></td> <td>0.9 ± 0.3</td> <td>302</td> <td>+<sup>b</sup></td> <td>?</td> <td>? </td></tr> <tr> <td><a href="/wiki/2-Methoxyestriol" title="2-Methoxyestriol">2-Methoxyestriol</a></td> <td>0.01 ± 0.00</td> <td>?</td> <td>Inactive</td> <td>?</td> <td>4 </td></tr> <tr class="sortbottom"> <td colspan="6" style="width: 1px; background-color:#eaecf0; text-align: center;"><b>Notes:</b> Values are mean ± SD or range. <abbr title="estrogen receptor">ER</abbr> <abbr title="Relative binding affinity">RBA</abbr> = <a href="/wiki/Relative_binding_affinity" class="mw-redirect" title="Relative binding affinity">Relative binding affinity</a> to <a href="/wiki/Estrogen_receptor" title="Estrogen receptor">estrogen receptors</a> of rat <a href="/wiki/Uterus" title="Uterus">uterine</a> <a href="/wiki/Cytosol" title="Cytosol">cytosol</a>. Uterine weight = Percentage change in uterine wet weight of <a href="/wiki/Ovariectomy" class="mw-redirect" title="Ovariectomy">ovariectomized</a> rats after 72 hours with continuous administration of 1 μg/hour via <a href="/wiki/Subcutaneous_implant" title="Subcutaneous implant">subcutaneously implanted</a> <a href="/wiki/Osmotic_pump" class="mw-redirect" title="Osmotic pump">osmotic pumps</a>. <abbr title="Luteinizing hormone">LH</abbr> levels = <a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone">Luteinizing hormone</a> levels relative to baseline of ovariectomized rats after 24 to 72 hours of continuous administration via subcutaneous implant. <b>Footnotes:</b> <sup>a</sup> = <a href="/wiki/Synthetic_compound" class="mw-redirect" title="Synthetic compound">Synthetic</a> (i.e., not <a href="/wiki/Endogenous" class="mw-redirect" title="Endogenous">endogenous</a>). <sup>b</sup> = Atypical uterotrophic effect which plateaus within 48 hours (estradiol's uterotrophy continues linearly up to 72 hours). <b>Sources:</b> See template. </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Biochemistry">Biochemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estriol&action=edit&section=2" title="Edit section: Biochemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Steroidogenesis.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/13/Steroidogenesis.svg/450px-Steroidogenesis.svg.png" decoding="async" width="450" height="399" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/13/Steroidogenesis.svg/675px-Steroidogenesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/13/Steroidogenesis.svg/900px-Steroidogenesis.svg.png 2x" data-file-width="1245" data-file-height="1105" /></a><figcaption>Human <a href="/wiki/Steroidogenesis" class="mw-redirect" title="Steroidogenesis">steroidogenesis</a>, showing estriol at bottom right.<sup id="cite_ref-HäggströmRichfield2014_15-0" class="reference"><a href="#cite_note-HäggströmRichfield2014-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> In essence, it follows the pathway from dehydroepiandrosterone or DHEA (at left), but with a modified DHEA with an additional OH-group.</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Biosynthesis">Biosynthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estriol&action=edit&section=3" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="In_non-pregnant_women">In non-pregnant women</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estriol&action=edit&section=4" title="Edit section: In non-pregnant women"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In women who are not pregnant estriol is produced in only very small quantities, and circulating levels are barely detectable.<sup id="cite_ref-IIIBarbieri2013_3-2" class="reference"><a href="#cite_note-IIIBarbieri2013-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Unlike estradiol and estrone, estriol is not synthesized in or secreted from the ovaries,<sup id="cite_ref-JaypeeBrothers2006_16-0" class="reference"><a href="#cite_note-JaypeeBrothers2006-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> and is instead derived mainly if not exclusively from 16α-<a href="/wiki/Hydroxylation" title="Hydroxylation">hydroxylation</a> of estradiol and estrone by <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> <a href="/wiki/Enzyme" title="Enzyme">enzymes</a> (e.g., <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a>) mainly in the <a href="/wiki/Liver" title="Liver">liver</a>.<sup id="cite_ref-HendersonPonder2003_17-0" class="reference"><a href="#cite_note-HendersonPonder2003-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Assali2013_18-0" class="reference"><a href="#cite_note-Assali2013-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Estriol is cleared from the <a href="/wiki/Circulatory_system" title="Circulatory system">circulation</a> rapidly in non-pregnant women, and so circulating levels are very low, but concentrations of estriol in the <a href="/wiki/Urine" title="Urine">urine</a> are relatively high.<sup id="cite_ref-HendersonPonder2003_17-1" class="reference"><a href="#cite_note-HendersonPonder2003-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p>Although circulating levels of estriol are very low outside of pregnancy, <a href="/wiki/Gravidity_and_parity" title="Gravidity and parity">parous</a> women have been found to have levels of estriol that are to some degree higher than those of <a href="/wiki/Nulliparity" class="mw-redirect" title="Nulliparity">nulliparous</a> women.<sup id="cite_ref-LappanoRosano2010_8-3" class="reference"><a href="#cite_note-LappanoRosano2010-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="In_pregnant_women">In pregnant women</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estriol&action=edit&section=5" title="Edit section: In pregnant women"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Estriol is produced in quantities that are notable only during <a href="/wiki/Pregnancy" title="Pregnancy">pregnancy</a>.<sup id="cite_ref-IIIBarbieri2013_3-3" class="reference"><a href="#cite_note-IIIBarbieri2013-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Levels of estriol increase 1,000-fold during pregnancy,<sup id="cite_ref-LappanoRosano2010_8-4" class="reference"><a href="#cite_note-LappanoRosano2010-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> whereas levels of estradiol and estrone increase 100-fold,<sup id="cite_ref-Blackburn2014_12-1" class="reference"><a href="#cite_note-Blackburn2014-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> and estriol accounts for 90% of the estrogens in the urine of pregnant women.<sup id="cite_ref-(Prof.)2001_5-1" class="reference"><a href="#cite_note-(Prof.)2001-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> At term, the daily production of estriol by the placenta is 35 to 45 mg,<sup id="cite_ref-Blackburn2014_12-2" class="reference"><a href="#cite_note-Blackburn2014-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> and levels in the maternal circulation are 8 to 13 ng/dL.<sup id="cite_ref-IIIBarbieri2013_3-4" class="reference"><a href="#cite_note-IIIBarbieri2013-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>The <a href="/wiki/Placenta" title="Placenta">placenta</a> produces <a href="/wiki/Pregnenolone" title="Pregnenolone">pregnenolone</a> and <a href="/wiki/Progesterone" title="Progesterone">progesterone</a> from circulating <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a>.<sup id="cite_ref-Goodman2003_4-2" class="reference"><a href="#cite_note-Goodman2003-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Pregnenolone is taken up by the fetal <a href="/wiki/Adrenal_gland" title="Adrenal gland">adrenal glands</a> and converted into <a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">dehydroepiandrosterone</a> (DHEA), which is then <a href="/wiki/Sulfation" title="Sulfation">sulfated</a> by <a href="/wiki/Steroid_sulfotransferase" title="Steroid sulfotransferase">steroid sulfotransferase</a> into <a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">dehydroepiandrosterone sulfate</a> (DHEA-S).<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (October 2016)">citation needed</span></a></i>]</sup> DHEA-S is <a href="/wiki/Hydroxylation" title="Hydroxylation">hydroxylated</a> by high <a href="/wiki/CYP3A7" title="CYP3A7">CYP3A7</a> expression and activity into <a href="/wiki/16%CE%B1-hydroxy-DHEA-S" class="mw-redirect" title="16α-hydroxy-DHEA-S">16α-hydroxy-DHEA-S</a> (16α-OH-DHEA-S) in the fetal <a href="/wiki/Liver" title="Liver">liver</a> and to a limited extent in the fetal adrenal glands.<sup id="cite_ref-IIIBarbieri2013_3-5" class="reference"><a href="#cite_note-IIIBarbieri2013-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Yamazaki2014_19-0" class="reference"><a href="#cite_note-Yamazaki2014-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> 16α-OH-DHEA-S is then taken up by the placenta.<sup id="cite_ref-IIIBarbieri2013_3-6" class="reference"><a href="#cite_note-IIIBarbieri2013-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Due to high expression of <a href="/wiki/Steroid_sulfatase" title="Steroid sulfatase">steroid sulfatase</a> in the placenta, 16α-OH-DHEA-S is rapidly cleaved into <a href="/wiki/16%CE%B1-OH-DHEA" class="mw-redirect" title="16α-OH-DHEA">16α-OH-DHEA</a>.<sup id="cite_ref-IIIBarbieri2013_3-7" class="reference"><a href="#cite_note-IIIBarbieri2013-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Then, 16α-OH-DHEA is converted by <a href="/wiki/3%CE%B2-hydroxysteroid_dehydrogenase" class="mw-redirect" title="3β-hydroxysteroid dehydrogenase">3β-hydroxysteroid dehydrogenase</a> <a href="/wiki/HSD3B1" title="HSD3B1">type I</a> (3β-HSD1) into <a href="/wiki/16%CE%B1-hydroxyandrostenedione" class="mw-redirect" title="16α-hydroxyandrostenedione">16α-hydroxyandrostenedione</a> (16α-OH-A4) and 16α-OH-A4 is converted by <a href="/wiki/Aromatase" title="Aromatase">aromatase</a> into <a href="/wiki/16%CE%B1-hydroxyestrone" class="mw-redirect" title="16α-hydroxyestrone">16α-hydroxyestrone</a> (16α-OH-E1),<sup id="cite_ref-AcademicPress2005_20-0" class="reference"><a href="#cite_note-AcademicPress2005-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> which is subsequently converted into estriol by <a href="/wiki/17%CE%B2-hydroxysteroid_dehydrogenase" class="mw-redirect" title="17β-hydroxysteroid dehydrogenase">17β-hydroxysteroid dehydrogenase</a> and then secreted predominantly into the maternal circulation.<sup id="cite_ref-IIIBarbieri2013_3-8" class="reference"><a href="#cite_note-IIIBarbieri2013-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HendersonPonder2003_17-2" class="reference"><a href="#cite_note-HendersonPonder2003-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> Approximately 90% of precursors in estriol formation originate from the fetus.<sup id="cite_ref-HendersonPonder2003_17-3" class="reference"><a href="#cite_note-HendersonPonder2003-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p>During pregnancy, 90 to 95% of estriol in the maternal circulation is <a href="/wiki/Conjugation_(biochemistry)" class="mw-redirect" title="Conjugation (biochemistry)">conjugated</a> in the form of <a href="/wiki/Estriol_glucuronide" title="Estriol glucuronide">estriol glucuronide</a> and <a href="/wiki/Estriol_sulfate" title="Estriol sulfate">estriol sulfate</a>, and levels of unconjugated estriol are slightly less than those of unconjugated estradiol and similar to those of unconjugated estrone.<sup id="cite_ref-(Prof.)2001_5-2" class="reference"><a href="#cite_note-(Prof.)2001-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> As such, target tissues are likely to be exposed to similar amounts of free estriol, estradiol, and estrone during pregnancy.<sup id="cite_ref-(Prof.)2001_5-3" class="reference"><a href="#cite_note-(Prof.)2001-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Estrone" title="Estrone">Estrone</a> and <a href="/wiki/Estradiol" title="Estradiol">estradiol</a> are also produced in the placenta during pregnancy.<sup id="cite_ref-IIIBarbieri2013_3-9" class="reference"><a href="#cite_note-IIIBarbieri2013-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> However, in the case of estrone and estradiol, DHEA-S is taken up by the placenta and cleaved by steroid sulfatase into <a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">dehydroepiandrosterone</a> (DHEA), DHEA is converted by <a href="/wiki/3%CE%B2-hydroxysteroid_dehydrogenase" class="mw-redirect" title="3β-hydroxysteroid dehydrogenase">3β-hydroxysteroid dehydrogenase</a> <a href="/wiki/HSD3B1" title="HSD3B1">type I</a> into <a href="/wiki/Androstenedione" title="Androstenedione">androstenedione</a>, and androstenedione is aromatized into estrone.<sup id="cite_ref-IIIBarbieri2013_3-10" class="reference"><a href="#cite_note-IIIBarbieri2013-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Then, placental <a href="/wiki/17%CE%B2-hydroxysteroid_dehydrogenase" class="mw-redirect" title="17β-hydroxysteroid dehydrogenase">17β-hydroxysteroid dehydrogenase</a> interconverts estrone and estradiol and the two hormones are secreted into the maternal circulation.<sup id="cite_ref-IIIBarbieri2013_3-11" class="reference"><a href="#cite_note-IIIBarbieri2013-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> DHEA-S that is taken up by the placenta is mainly produced by the fetal adrenal glands.<sup id="cite_ref-IIIBarbieri2013_3-12" class="reference"><a href="#cite_note-IIIBarbieri2013-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Distribution">Distribution</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estriol&action=edit&section=6" title="Edit section: Distribution"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Estriol is poorly bound to <a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin">sex hormone-binding globulin</a> (SHBG),<sup id="cite_ref-Buchsbaum2012_21-0" class="reference"><a href="#cite_note-Buchsbaum2012-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> with much lower <a href="/wiki/Binding_affinity" class="mw-redirect" title="Binding affinity">binding affinity</a> for this protein, relative to estradiol, and hence a greater fraction available for <a href="/wiki/Biological_activity" title="Biological activity">biological activity</a>.<sup id="cite_ref-LorenzoHorowitz2015_22-0" class="reference"><a href="#cite_note-LorenzoHorowitz2015-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Metabolism">Metabolism</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estriol&action=edit&section=7" title="Edit section: Metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Estriol is <a href="/wiki/Metabolism" title="Metabolism">metabolized</a> via <a href="/wiki/Glucuronidation" title="Glucuronidation">glucuronidation</a> and <a href="/wiki/Sulfation" title="Sulfation">sulfation</a>.<sup id="cite_ref-OettelSchillinger2012_23-0" class="reference"><a href="#cite_note-OettelSchillinger2012-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MuseyKirdani1973_24-0" class="reference"><a href="#cite_note-MuseyKirdani1973-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Excretion">Excretion</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estriol&action=edit&section=8" title="Edit section: Excretion"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The main <a href="/wiki/Urine" title="Urine">urinary</a> <a href="/wiki/Metabolite" title="Metabolite">metabolites</a> of <a href="/wiki/Exogenous" class="mw-redirect" title="Exogenous">exogenous</a> estriol administered via <a href="/wiki/Intravenous_injection" class="mw-redirect" title="Intravenous injection">intravenous injection</a> in <a href="/wiki/Baboon" title="Baboon">baboons</a> have been found to be <a href="/wiki/Estriol_16%CE%B1-glucuronide" class="mw-redirect" title="Estriol 16α-glucuronide">estriol 16α-glucuronide</a> (65.8%), <a href="/wiki/Estriol_3-glucuronide" title="Estriol 3-glucuronide">estriol 3-glucuronide</a> (14.2%), <a href="/wiki/Estriol_3-sulfate" class="mw-redirect" title="Estriol 3-sulfate">estriol 3-sulfate</a> (13.4%), and <a href="/wiki/Estriol_3-sulfate_16%CE%B1-glucuronide" class="mw-redirect" title="Estriol 3-sulfate 16α-glucuronide">estriol 3-sulfate 16α-glucuronide</a> (5.1%).<sup id="cite_ref-OettelSchillinger2012_23-1" class="reference"><a href="#cite_note-OettelSchillinger2012-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MuseyKirdani1973_24-1" class="reference"><a href="#cite_note-MuseyKirdani1973-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> and <a href="/wiki/Excretion" title="Excretion">excretion</a> of estriol in these animals closely resembled that which has been observed in humans.<sup id="cite_ref-MuseyKirdani1973_24-2" class="reference"><a href="#cite_note-MuseyKirdani1973-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> In non-pregnant women, estriol urinary excretion ranges between 0.02–0.1 mg every 24 hours. In comparison, in near-term pregnant women, estriol urinary excretion ranges from 50–150 mg every 24 hours.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Medical_use">Medical use</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estriol&action=edit&section=9" title="Edit section: Medical use"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Estriol_(medication)" title="Estriol (medication)">Estriol (medication)</a></div> <p>Estriol is used as a <a href="/wiki/Medication" title="Medication">medication</a>, primarily in <a href="/wiki/Hormone_replacement_therapy" title="Hormone replacement therapy">hormone therapy</a> for <a href="/wiki/Menopause" title="Menopause">menopausal</a> <a href="/wiki/Symptom" class="mw-redirect" title="Symptom">symptoms</a>.<sup id="cite_ref-pmid16112947_1-6" class="reference"><a href="#cite_note-pmid16112947-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estriol&action=edit&section=10" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></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" title="List of estrogens">List of estrogens</a></div> <table role="presentation" cellpadding="0" style="border-spacing:0; clear:right; float:right;"> <tbody><tr> <td><div class="thumb tright"> <div class="thumbinner" style="width:396px;"> <div style="clear: both; font-weight: bold; font-size: 106.4%; text-align: center; background-color: light-dark(aliceblue,var(--background-color-neutral)); color:var(--color-base,light-dark(#202122,#eaecf0)); margin-bottom:3px;"><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:Chemical_structures_of_major_endogenous_estrogens" title="Template:Chemical structures of major endogenous estrogens"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Chemical_structures_of_major_endogenous_estrogens" title="Template talk:Chemical structures of major endogenous estrogens"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Chemical_structures_of_major_endogenous_estrogens" title="Special:EditPage/Template:Chemical structures of major endogenous estrogens"><abbr title="Edit this template">e</abbr></a></li></ul></div> Structures of major endogenous estrogens</div> <div class="skin-invert" style="position:relative; width:394px; height:260px; overflow:hidden; border:solid #ccc 1px; background-color:white;"> <div style="left:0px; top:0px; width:394px; position:absolute"> <span typeof="mw:File"><span><img alt="Chemical structures of major endogenous estrogens" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6e/Chemical_structures_of_major_endogenous_estrogens_no_labels.png/394px-Chemical_structures_of_major_endogenous_estrogens_no_labels.png" decoding="async" width="394" height="262" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6e/Chemical_structures_of_major_endogenous_estrogens_no_labels.png/591px-Chemical_structures_of_major_endogenous_estrogens_no_labels.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6e/Chemical_structures_of_major_endogenous_estrogens_no_labels.png/788px-Chemical_structures_of_major_endogenous_estrogens_no_labels.png 2x" data-file-width="2560" data-file-height="1700" /></span></span> </div> <div style="text-align:center; font-size:14px; line-height:110%"> <div style="background-color:transparent; color:black"><div id="annotation_53x107" style="position:absolute; left:53px; top:107px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Estrone" title="Estrone">Estrone</a> (E1)</span></div> <div id="annotation_251x107" style="position:absolute; left:251px; top:107px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a> (E2)</span></div> <div id="annotation_55x235" style="position:absolute; left:55px; top:235px; line-height:110%;"><span style="background-color:transparent; color:inherit;">Estriol (E3)</span></div> <div id="annotation_253x235" style="position:absolute; left:253px; top:235px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Estetrol" title="Estetrol">Estetrol</a> (E4)</span></div></div> </div> </div> <div class="thumbcaption" style="clear:left"><div style="float:left;margin-right:0.5em"><span typeof="mw:File"><span title="The image above contains clickable links"><img alt="The image above contains clickable links" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/20px-Interactive_icon.svg.png" decoding="async" width="18" height="27" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/40px-Interactive_icon.svg.png 1.5x" data-file-width="133" data-file-height="200" /></span></span></div>Note the <a href="/wiki/Hydroxyl_group" class="mw-redirect" title="Hydroxyl group">hydroxyl</a> (–OH) <a href="/wiki/Functional_group" title="Functional group">groups</a>: estrone (E1) has one, estradiol (E2) has two, estriol (E3) has three, and estetrol (E4) has four.</div> </div> </div> </td></tr></tbody></table> <p><br /> Estriol, also known as 16α-hydroxyestradiol or as estra-1,3,5(10)-triene-3,16α,17β-triol, is a <a href="/wiki/Natural_compound" class="mw-redirect" title="Natural compound">naturally occurring</a> <a href="/wiki/Estrane" title="Estrane">estrane</a> <a href="/wiki/Steroid" title="Steroid">steroid</a> with <a href="/wiki/Double_bond" title="Double bond">double bonds</a> between the C1 and C2, C3 and C4, and C5 and C10 positions and <a href="/wiki/Hydroxyl_group" class="mw-redirect" title="Hydroxyl group">hydroxyl groups</a> at the C3, C16α, and C17β positions.<sup id="cite_ref-Elks2014_26-0" class="reference"><a href="#cite_note-Elks2014-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-IndexNominum2000_27-0" class="reference"><a href="#cite_note-IndexNominum2000-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> The name <i>estriol</i> and the abbreviation <i>E3</i> were derived from the chemical terms <i><a href="/wiki/Estrin_(compound)" class="mw-redirect" title="Estrin (compound)"><b>estr</b>in</a></i> (estra-1,3,5(10)-triene) and <i><b><a href="/wiki/Triol" title="Triol">triol</a></b></i> (three hydroxyl groups). </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estriol&action=edit&section=11" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Estriol was discovered in 1930.<sup id="cite_ref-Josimovich2013_28-0" class="reference"><a href="#cite_note-Josimovich2013-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SartorelliJohns2013_29-0" class="reference"><a href="#cite_note-SartorelliJohns2013-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> It was isolated and purified from the <a href="/wiki/Urine" title="Urine">urine</a> of pregnant women by Marrian and colleagues.<sup id="cite_ref-Josimovich2013_28-1" class="reference"><a href="#cite_note-Josimovich2013-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SartorelliJohns2013_29-1" class="reference"><a href="#cite_note-SartorelliJohns2013-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Use_in_screening">Use in screening</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estriol&action=edit&section=12" title="Edit section: Use in screening"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Estriol can be measured in maternal blood or urine and can be used as a marker of fetal health and well-being. If levels of unconjugated estriol (uE3 or free estriol) are abnormally low in a pregnant woman, this may indicate chromosomal or congenital anomalies like <a href="/wiki/Down_syndrome" title="Down syndrome">Down syndrome</a> or <a href="/wiki/Edward%27s_syndrome" class="mw-redirect" title="Edward's syndrome">Edward's syndrome</a>. It is included as part of the <a href="/wiki/Triple_test" title="Triple test">triple test</a> and <a href="/wiki/Quadruple_test" class="mw-redirect" title="Quadruple test">quadruple test</a><sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> for antenatal screening for fetal anomalies. </p><p>Because many pathological conditions in a pregnant woman can cause deviations in estriol levels, these screenings are often seen as less definitive of fetal-placental health than a <a href="/wiki/Nonstress_test" title="Nonstress test">nonstress test</a>. Conditions which can create <a href="/wiki/False_positives" class="mw-redirect" title="False positives">false positives</a> and <a href="/wiki/False_negatives" class="mw-redirect" title="False negatives">false negatives</a> in estriol testing for fetal distress include <a href="/wiki/Preeclampsia" class="mw-redirect" title="Preeclampsia">preeclampsia</a>, <a href="/wiki/Anemia" title="Anemia">anemia</a>, and impaired <a href="/wiki/Kidney_function" class="mw-redirect" title="Kidney function">kidney function</a>.<sup id="cite_ref-isbn0-323-05747-0_31-0" class="reference"><a href="#cite_note-isbn0-323-05747-0-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estriol&action=edit&section=13" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <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 mw-references-columns"><ol class="references"> <li id="cite_note-pmid16112947-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid16112947_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid16112947_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-pmid16112947_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-pmid16112947_1-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-pmid16112947_1-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-pmid16112947_1-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-pmid16112947_1-6"><sup><i><b>g</b></i></sup></a></span> <span class="reference-text"><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="CITEREFKuhl2005" class="citation journal cs1">Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". <i>Climacteric</i>. <b>8</b> (Suppl 1): <span class="nowrap">3–</span>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=%3Cspan+class%3D%22nowrap%22%3E3-%3C%2Fspan%3E63&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%3AEstriol" class="Z3988"></span></span> </li> <li id="cite_note-Puri2005-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-Puri2005_2-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPuri2005" class="citation book cs1">Puri (1 January 2005). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=XnPOEEeXXnYC&pg=PA793"><i>Textbook Of Biochemistry</i></a>. Elsevier India. pp. 793–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-81-8147-844-3" title="Special:BookSources/978-81-8147-844-3"><bdi>978-81-8147-844-3</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+Biochemistry&rft.pages=793-&rft.pub=Elsevier+India&rft.date=2005-01-01&rft.isbn=978-81-8147-844-3&rft.au=Puri&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DXnPOEEeXXnYC%26pg%3DPA793&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstriol" class="Z3988"></span></span> </li> <li id="cite_note-IIIBarbieri2013-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-IIIBarbieri2013_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-IIIBarbieri2013_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-IIIBarbieri2013_3-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-IIIBarbieri2013_3-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-IIIBarbieri2013_3-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-IIIBarbieri2013_3-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-IIIBarbieri2013_3-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-IIIBarbieri2013_3-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-IIIBarbieri2013_3-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-IIIBarbieri2013_3-9"><sup><i><b>j</b></i></sup></a> <a href="#cite_ref-IIIBarbieri2013_3-10"><sup><i><b>k</b></i></sup></a> <a href="#cite_ref-IIIBarbieri2013_3-11"><sup><i><b>l</b></i></sup></a> <a href="#cite_ref-IIIBarbieri2013_3-12"><sup><i><b>m</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFStraussBarbieri2013" class="citation book cs1">Strauss JF, Barbieri RL (13 September 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=KZ95AAAAQBAJ&pg=PA256"><i>Yen and Jaffe's Reproductive Endocrinology</i></a>. Elsevier Health Sciences. pp. 256–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4557-2758-2" title="Special:BookSources/978-1-4557-2758-2"><bdi>978-1-4557-2758-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Yen+and+Jaffe%27s+Reproductive+Endocrinology&rft.pages=256-&rft.pub=Elsevier+Health+Sciences&rft.date=2013-09-13&rft.isbn=978-1-4557-2758-2&rft.aulast=Strauss&rft.aufirst=Jerome+F.&rft.au=Barbieri%2C+Robert+L.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DKZ95AAAAQBAJ%26pg%3DPA256&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstriol" class="Z3988"></span></span> </li> <li id="cite_note-Goodman2003-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-Goodman2003_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Goodman2003_4-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Goodman2003_4-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFH._Maurice_Goodman2003" class="citation book cs1">H. Maurice Goodman (14 March 2003). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=ica8EeRFeawC&pg=PA436"><i>Basic Medical Endocrinology</i></a>. Academic Press. pp. 436–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-08-048836-3" title="Special:BookSources/978-0-08-048836-3"><bdi>978-0-08-048836-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Basic+Medical+Endocrinology&rft.pages=436-&rft.pub=Academic+Press&rft.date=2003-03-14&rft.isbn=978-0-08-048836-3&rft.au=H.+Maurice+Goodman&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dica8EeRFeawC%26pg%3DPA436&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstriol" class="Z3988"></span></span> </li> <li id="cite_note-(Prof.)2001-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-(Prof.)2001_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-(Prof.)2001_5-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-(Prof.)2001_5-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-(Prof.)2001_5-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRoger_Smith_(Prof.)2001" class="citation book cs1">Roger Smith (Prof.) (1 January 2001). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=0N6Ua0O8gWwC&pg=PA89"><i>The Endocrinology of Parturition: Basic Science and Clinical Application</i></a>. Karger Medical and Scientific Publishers. pp. 89–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-8055-7195-1" title="Special:BookSources/978-3-8055-7195-1"><bdi>978-3-8055-7195-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Endocrinology+of+Parturition%3A+Basic+Science+and+Clinical+Application&rft.pages=89-&rft.pub=Karger+Medical+and+Scientific+Publishers&rft.date=2001-01-01&rft.isbn=978-3-8055-7195-1&rft.au=Roger+Smith+%28Prof.%29&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D0N6Ua0O8gWwC%26pg%3DPA89&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstriol" class="Z3988"></span></span> </li> <li id="cite_note-JaouenSalmain2015-6"><span class="mw-cite-backlink">^ <a href="#cite_ref-JaouenSalmain2015_6-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-JaouenSalmain2015_6-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-JaouenSalmain2015_6-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFJaouenSalmain2015" class="citation book cs1">Jaouen G, Salmain M (20 April 2015). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=n7ynBQAAQBAJ&pg=PA45"><i>Bioorganometallic Chemistry: Applications in Drug Discovery, Biocatalysis, and Imaging</i></a>. John Wiley & Sons. pp. 45–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-527-33527-5" title="Special:BookSources/978-3-527-33527-5"><bdi>978-3-527-33527-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Bioorganometallic+Chemistry%3A+Applications+in+Drug+Discovery%2C+Biocatalysis%2C+and+Imaging&rft.pages=45-&rft.pub=John+Wiley+%26+Sons&rft.date=2015-04-20&rft.isbn=978-3-527-33527-5&rft.aulast=Jaouen&rft.aufirst=G%C3%A9rard&rft.au=Salmain%2C+Michle&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dn7ynBQAAQBAJ%26pg%3DPA45&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstriol" class="Z3988"></span></span> </li> <li id="cite_note-pmid16554039-7"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid16554039_7-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid16554039_7-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-pmid16554039_7-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><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, Nicolas JC, Cavaillès V, Balaguer P (May 2006). "Evaluation of ligand selectivity using reporter cell lines stably expressing estrogen receptor alpha or beta". <i>Biochemical Pharmacology</i>. <b>71</b> (10): <span class="nowrap">1459–</span>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%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=%3Cspan+class%3D%22nowrap%22%3E1459-%3C%2Fspan%3E69&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%3AEstriol" class="Z3988"></span></span> </li> <li id="cite_note-LappanoRosano2010-8"><span class="mw-cite-backlink">^ <a href="#cite_ref-LappanoRosano2010_8-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-LappanoRosano2010_8-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-LappanoRosano2010_8-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-LappanoRosano2010_8-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-LappanoRosano2010_8-4"><sup><i><b>e</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLappanoRosanoDe_MarcoDe_Francesco2010" class="citation journal cs1">Lappano R, Rosano C, De Marco P, De Francesco EM, Pezzi V, Maggiolini M (May 2010). "Estriol acts as a GPR30 antagonist in estrogen receptor-negative breast cancer cells". <i>Molecular and Cellular Endocrinology</i>. <b>320</b> (<span class="nowrap">1–</span>2): <span class="nowrap">162–</span>70. <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.2010.02.006">10.1016/j.mce.2010.02.006</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/20138962">20138962</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:24525995">24525995</a>.</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=Estriol+acts+as+a+GPR30+antagonist+in+estrogen+receptor-negative+breast+cancer+cells&rft.volume=320&rft.issue=%3Cspan+class%3D%22nowrap%22%3E1%E2%80%93%3C%2Fspan%3E2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E162-%3C%2Fspan%3E70&rft.date=2010-05&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A24525995%23id-name%3DS2CID&rft_id=info%3Apmid%2F20138962&rft_id=info%3Adoi%2F10.1016%2Fj.mce.2010.02.006&rft.aulast=Lappano&rft.aufirst=R&rft.au=Rosano%2C+C&rft.au=De+Marco%2C+P&rft.au=De+Francesco%2C+EM&rft.au=Pezzi%2C+V&rft.au=Maggiolini%2C+M&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstriol" class="Z3988"></span></span> </li> <li id="cite_note-Becker2001-9"><span class="mw-cite-backlink">^ <a href="#cite_ref-Becker2001_9-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Becker2001_9-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKenneth_L._Becker2001" class="citation book cs1">Kenneth L. Becker (2001). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=FVfzRvaucq8C&pg=PA1061"><i>Principles and Practice of Endocrinology and Metabolism</i></a>. Lippincott Williams & Wilkins. pp. 932, 1061. <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=932%2C+1061&rft.pub=Lippincott+Williams+%26+Wilkins&rft.date=2001&rft.isbn=978-0-7817-1750-2&rft.au=Kenneth+L.+Becker&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DFVfzRvaucq8C%26pg%3DPA1061&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstriol" class="Z3988"></span></span> </li> <li id="cite_note-RubanyiKauffman2003-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-RubanyiKauffman2003_10-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRubanyiKauffman2003" class="citation book cs1">Rubanyi GM, Kauffman R (2 September 2003). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=U6WU25VeOBsC&pg=PA8"><i>Estrogen and the Vessel Wall</i></a>. CRC Press. pp. 8–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-203-30393-1" title="Special:BookSources/978-0-203-30393-1"><bdi>978-0-203-30393-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Estrogen+and+the+Vessel+Wall&rft.pages=8-&rft.pub=CRC+Press&rft.date=2003-09-02&rft.isbn=978-0-203-30393-1&rft.aulast=Rubanyi&rft.aufirst=Gabor+M.&rft.au=Kauffman%2C+R&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DU6WU25VeOBsC%26pg%3DPA8&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstriol" class="Z3988"></span></span> </li> <li id="cite_note-Labhart2012-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-Labhart2012_11-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFA._Labhart2012" class="citation book cs1">A. Labhart (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=DAgJCAAAQBAJ&pg=PA548"><i>Clinical Endocrinology: Theory and Practice</i></a>. Springer Science & Business Media. pp. 548–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-96158-8" title="Special:BookSources/978-3-642-96158-8"><bdi>978-3-642-96158-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Clinical+Endocrinology%3A+Theory+and+Practice&rft.pages=548-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-3-642-96158-8&rft.au=A.+Labhart&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DDAgJCAAAQBAJ%26pg%3DPA548&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstriol" class="Z3988"></span></span> </li> <li id="cite_note-Blackburn2014-12"><span class="mw-cite-backlink">^ <a href="#cite_ref-Blackburn2014_12-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Blackburn2014_12-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Blackburn2014_12-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSusan_Blackburn2014" class="citation book cs1">Susan Blackburn (14 April 2014). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=RNLsAwAAQBAJ&pg=PA93"><i>Maternal, Fetal, & Neonatal Physiology</i></a>. Elsevier Health Sciences. pp. 39, 93. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-323-29296-2" title="Special:BookSources/978-0-323-29296-2"><bdi>978-0-323-29296-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Maternal%2C+Fetal%2C+%26+Neonatal+Physiology&rft.pages=39%2C+93&rft.pub=Elsevier+Health+Sciences&rft.date=2014-04-14&rft.isbn=978-0-323-29296-2&rft.au=Susan+Blackburn&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DRNLsAwAAQBAJ%26pg%3DPA93&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstriol" class="Z3988"></span></span> </li> <li id="cite_note-pmid26023144-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid26023144_13-0">^</a></b></span> <span class="reference-text"><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>. <i>Pharmacol. Rev</i>. <b>67</b> (3): <span class="nowrap">505–</span>40. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1124%2Fpr.114.009712">10.1124/pr.114.009712</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4485017">4485017</a></span>. <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=Pharmacol.+Rev.&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=%3Cspan+class%3D%22nowrap%22%3E505-%3C%2Fspan%3E40&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%3AEstriol" class="Z3988"></span></span> </li> <li id="cite_note-GirgertEmons2014-14"><span class="mw-cite-backlink">^ <a href="#cite_ref-GirgertEmons2014_14-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-GirgertEmons2014_14-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFGirgertEmonsGründker2014" class="citation journal cs1">Girgert R, Emons G, Gründker C (December 2014). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4364648">"Inhibition of GPR30 by estriol prevents growth stimulation of triple-negative breast cancer cells by 17β-estradiol"</a>. <i>BMC Cancer</i>. <b>14</b> (1): 935. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1186%2F1471-2407-14-935">10.1186/1471-2407-14-935</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4364648">4364648</a></span>. <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/25496649">25496649</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=BMC+Cancer&rft.atitle=Inhibition+of+GPR30+by+estriol+prevents+growth+stimulation+of+triple-negative+breast+cancer+cells+by+17%CE%B2-estradiol&rft.volume=14&rft.issue=1&rft.pages=935&rft.date=2014-12&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4364648%23id-name%3DPMC&rft_id=info%3Apmid%2F25496649&rft_id=info%3Adoi%2F10.1186%2F1471-2407-14-935&rft.aulast=Girgert&rft.aufirst=R&rft.au=Emons%2C+G&rft.au=Gr%C3%BCndker%2C+C&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4364648&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstriol" class="Z3988"></span></span> </li> <li id="cite_note-HäggströmRichfield2014-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-HäggströmRichfield2014_15-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHäggströmRichfield2014" class="citation cs2">Häggström M, Richfield D (2014), "Diagram of the pathways of human steroidogenesis", <i>WikiJournal of Medicine</i>, <b>1</b> (1), <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.15347%2Fwjm%2F2014.005">10.15347/wjm/2014.005</a></span>, <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/2002-4436">2002-4436</a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=WikiJournal+of+Medicine&rft.atitle=Diagram+of+the+pathways+of+human+steroidogenesis&rft.volume=1&rft.issue=1&rft.date=2014&rft_id=info%3Adoi%2F10.15347%2Fwjm%2F2014.005&rft.issn=2002-4436&rft.aulast=H%C3%A4ggstr%C3%B6m&rft.aufirst=Mikaeljournal&rft.au=Richfield%2C+David&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstriol" class="Z3988"></span></span> </li> <li id="cite_note-JaypeeBrothers2006-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-JaypeeBrothers2006_16-0">^</a></b></span> <span class="reference-text"><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=s3j3mp09CAkC&pg=PA4"><i>Medical Disorders in Pregnancy – An Update</i></a>. Jaypee Brothers Publishers. 2006. pp. 4–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-81-8061-711-9" title="Special:BookSources/978-81-8061-711-9"><bdi>978-81-8061-711-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Medical+Disorders+in+Pregnancy+%E2%80%93+An+Update&rft.pages=4-&rft.pub=Jaypee+Brothers+Publishers&rft.date=2006&rft.isbn=978-81-8061-711-9&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Ds3j3mp09CAkC%26pg%3DPA4&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstriol" class="Z3988"></span><sup class="noprint Inline-Template"><span style="white-space: nowrap;">[<i><a href="/wiki/Wikipedia:Link_rot" title="Wikipedia:Link rot"><span title=" Dead link tagged March 2024">permanent dead link</span></a></i><span style="visibility:hidden; color:transparent; padding-left:2px">‍</span>]</span></sup></span> </li> <li id="cite_note-HendersonPonder2003-17"><span class="mw-cite-backlink">^ <a href="#cite_ref-HendersonPonder2003_17-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-HendersonPonder2003_17-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-HendersonPonder2003_17-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-HendersonPonder2003_17-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHendersonPonderRoss2003" class="citation book cs1">Henderson BE, Ponder B, Ross RK (13 March 2003). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=VzIWd4faVVQC&pg=PA25"><i>Hormones, Genes, and Cancer</i></a>. Oxford University Press. pp. 25–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-19-977158-5" title="Special:BookSources/978-0-19-977158-5"><bdi>978-0-19-977158-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Hormones%2C+Genes%2C+and+Cancer&rft.pages=25-&rft.pub=Oxford+University+Press&rft.date=2003-03-13&rft.isbn=978-0-19-977158-5&rft.aulast=Henderson&rft.aufirst=Brian+E.&rft.au=Ponder%2C+Bruce&rft.au=Ross%2C+Ronald+K.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DVzIWd4faVVQC%26pg%3DPA25&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstriol" class="Z3988"></span></span> </li> <li id="cite_note-Assali2013-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-Assali2013_18-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFN._S._Assali2013" class="citation book cs1">N. S. Assali (3 September 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=mSzLBAAAQBAJ&pg=PA341"><i>The Maternal Organism</i></a>. Elsevier. pp. 341–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4832-6380-9" title="Special:BookSources/978-1-4832-6380-9"><bdi>978-1-4832-6380-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Maternal+Organism&rft.pages=341-&rft.pub=Elsevier&rft.date=2013-09-03&rft.isbn=978-1-4832-6380-9&rft.au=N.+S.+Assali&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DmSzLBAAAQBAJ%26pg%3DPA341&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstriol" class="Z3988"></span></span> </li> <li id="cite_note-Yamazaki2014-19"><span class="mw-cite-backlink"><b><a href="#cite_ref-Yamazaki2014_19-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHiroshi_Yamazaki2014" class="citation book cs1">Hiroshi Yamazaki (23 June 2014). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=9mslBAAAQBAJ&pg=PA385"><i>Fifty Years of Cytochrome P450 Research</i></a>. Springer. pp. 385–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-4-431-54992-5" title="Special:BookSources/978-4-431-54992-5"><bdi>978-4-431-54992-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Fifty+Years+of+Cytochrome+P450+Research&rft.pages=385-&rft.pub=Springer&rft.date=2014-06-23&rft.isbn=978-4-431-54992-5&rft.au=Hiroshi+Yamazaki&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D9mslBAAAQBAJ%26pg%3DPA385&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstriol" class="Z3988"></span></span> </li> <li id="cite_note-AcademicPress2005-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-AcademicPress2005_20-0">^</a></b></span> <span class="reference-text"><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=DUst5mwBfN0C&pg=PA282"><i>Vitamins and Hormones</i></a>. Academic Press. 7 September 2005. pp. 282–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-08-045978-3" title="Special:BookSources/978-0-08-045978-3"><bdi>978-0-08-045978-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Vitamins+and+Hormones&rft.pages=282-&rft.pub=Academic+Press&rft.date=2005-09-07&rft.isbn=978-0-08-045978-3&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DDUst5mwBfN0C%26pg%3DPA282&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstriol" class="Z3988"></span></span> </li> <li id="cite_note-Buchsbaum2012-21"><span class="mw-cite-backlink"><b><a href="#cite_ref-Buchsbaum2012_21-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFH.J._Buchsbaum2012" class="citation book cs1">H.J. Buchsbaum (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=z0LuBwAAQBAJ&pg=PA62"><i>The Menopause</i></a>. Springer Science & Business Media. pp. 62–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4612-5525-3" title="Special:BookSources/978-1-4612-5525-3"><bdi>978-1-4612-5525-3</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+Menopause&rft.pages=62-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-1-4612-5525-3&rft.au=H.J.+Buchsbaum&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dz0LuBwAAQBAJ%26pg%3DPA62&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstriol" class="Z3988"></span></span> </li> <li id="cite_note-LorenzoHorowitz2015-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-LorenzoHorowitz2015_22-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLorenzoHorowitzChoiTakayanagi2015" class="citation book cs1">Lorenzo J, Horowitz M, Choi Y, Takayanagi H, Schett G (23 September 2015). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=eOGcBAAAQBAJ&pg=PA216"><i>Osteoimmunology: Interactions of the Immune and Skeletal Systems</i></a>. Elsevier Science. pp. 216–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-12-800627-6" title="Special:BookSources/978-0-12-800627-6"><bdi>978-0-12-800627-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Osteoimmunology%3A+Interactions+of+the+Immune+and+Skeletal+Systems&rft.pages=216-&rft.pub=Elsevier+Science&rft.date=2015-09-23&rft.isbn=978-0-12-800627-6&rft.aulast=Lorenzo&rft.aufirst=Joseph&rft.au=Horowitz%2C+Mark&rft.au=Choi%2C+Yongwon&rft.au=Takayanagi%2C+Hiroshi&rft.au=Schett%2C+Georg&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DeOGcBAAAQBAJ%26pg%3DPA216&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstriol" class="Z3988"></span></span> </li> <li id="cite_note-OettelSchillinger2012-23"><span class="mw-cite-backlink">^ <a href="#cite_ref-OettelSchillinger2012_23-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-OettelSchillinger2012_23-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><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=PA265"><i>Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen</i></a>. Springer Science & Business Media. pp. 265–. <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=265-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-3-642-60107-1&rft.aulast=Oettel&rft.aufirst=Michael&rft.au=Schillinger%2C+Ekkehard&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DwBvyCAAAQBAJ%26pg%3DPA265&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstriol" class="Z3988"></span></span> </li> <li id="cite_note-MuseyKirdani1973-24"><span class="mw-cite-backlink">^ <a href="#cite_ref-MuseyKirdani1973_24-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-MuseyKirdani1973_24-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-MuseyKirdani1973_24-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMuseyKirdaniBhanalaphSandberg1973" class="citation journal cs1">Musey PI, Kirdani RY, Bhanalaph T, Sandberg AA (December 1973). "Estriol metabolism in the baboon: analysis of urinary and biliary metabolites". <i>Steroids</i>. <b>22</b> (6): <span class="nowrap">795–</span>817. <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%2F0039-128X%2873%2990054-8">10.1016/0039-128X(73)90054-8</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/4203562">4203562</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Steroids&rft.atitle=Estriol+metabolism+in+the+baboon%3A+analysis+of+urinary+and+biliary+metabolites&rft.volume=22&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E795-%3C%2Fspan%3E817&rft.date=1973-12&rft_id=info%3Adoi%2F10.1016%2F0039-128X%2873%2990054-8&rft_id=info%3Apmid%2F4203562&rft.aulast=Musey&rft.aufirst=PI&rft.au=Kirdani%2C+RY&rft.au=Bhanalaph%2C+T&rft.au=Sandberg%2C+AA&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstriol" class="Z3988"></span></span> </li> <li id="cite_note-25"><span class="mw-cite-backlink"><b><a href="#cite_ref-25">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://fertilitypedia.org/edu/biological-control/estriol">"Estriol"</a>. <i>Fertilitypedia</i><span class="reference-accessdate">. Retrieved <span class="nowrap">1 February</span> 2023</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Fertilitypedia&rft.atitle=Estriol&rft_id=https%3A%2F%2Ffertilitypedia.org%2Fedu%2Fbiological-control%2Festriol&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstriol" class="Z3988"></span></span> </li> <li id="cite_note-Elks2014-26"><span class="mw-cite-backlink"><b><a href="#cite_ref-Elks2014_26-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFJ._Elks2014" class="citation book cs1">J. Elks (14 November 2014). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA899"><i>The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies</i></a>. Springer. pp. 899–. <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=899-&rft.pub=Springer&rft.date=2014-11-14&rft.isbn=978-1-4757-2085-3&rft.au=J.+Elks&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D0vXTBwAAQBAJ%26pg%3DPA899&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstriol" class="Z3988"></span></span> </li> <li id="cite_note-IndexNominum2000-27"><span class="mw-cite-backlink"><b><a href="#cite_ref-IndexNominum2000_27-0">^</a></b></span> <span class="reference-text"><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=PA407"><i>Index Nominum 2000: International Drug Directory</i></a>. Taylor & Francis. January 2000. pp. 407–. <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=407-&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%3DPA407&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstriol" class="Z3988"></span></span> </li> <li id="cite_note-Josimovich2013-28"><span class="mw-cite-backlink">^ <a href="#cite_ref-Josimovich2013_28-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Josimovich2013_28-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFJ.B._Josimovich2013" class="citation book cs1">J.B. Josimovich (11 November 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=9vv2BwAAQBAJ&pg=PA31"><i>Gynecologic Endocrinology</i></a>. Springer Science & Business Media. pp. 31–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4613-2157-6" title="Special:BookSources/978-1-4613-2157-6"><bdi>978-1-4613-2157-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Gynecologic+Endocrinology&rft.pages=31-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2013-11-11&rft.isbn=978-1-4613-2157-6&rft.au=J.B.+Josimovich&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D9vv2BwAAQBAJ%26pg%3DPA31&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstriol" class="Z3988"></span></span> </li> <li id="cite_note-SartorelliJohns2013-29"><span class="mw-cite-backlink">^ <a href="#cite_ref-SartorelliJohns2013_29-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-SartorelliJohns2013_29-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSartorelliJohns2013" class="citation book cs1">Sartorelli AC, Johns DG (27 November 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=aU_oCAAAQBAJ&pg=PA104"><i>Antineoplastic and Immunosuppressive Agents</i></a>. Springer Science & Business Media. pp. 104–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-65806-8" title="Special:BookSources/978-3-642-65806-8"><bdi>978-3-642-65806-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Antineoplastic+and+Immunosuppressive+Agents&rft.pages=104-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2013-11-27&rft.isbn=978-3-642-65806-8&rft.aulast=Sartorelli&rft.aufirst=Alan+C.&rft.au=Johns%2C+David+G.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DaU_oCAAAQBAJ%26pg%3DPA104&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstriol" class="Z3988"></span></span> </li> <li id="cite_note-30"><span class="mw-cite-backlink"><b><a href="#cite_ref-30">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://medlineplus.gov/ency/article/007311.htm">"Quadruple screen test: MedlinePlus Medical Encyclopedia"</a>. <i>medlineplus.gov</i><span class="reference-accessdate">. Retrieved <span class="nowrap">2018-11-07</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=medlineplus.gov&rft.atitle=Quadruple+screen+test%3A+MedlinePlus+Medical+Encyclopedia&rft_id=https%3A%2F%2Fmedlineplus.gov%2Fency%2Farticle%2F007311.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstriol" class="Z3988"></span></span> </li> <li id="cite_note-isbn0-323-05747-0-31"><span class="mw-cite-backlink"><b><a href="#cite_ref-isbn0-323-05747-0_31-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPaganaPagana2009" class="citation book cs1">Pagana TJ, Pagana KD (2009). <span class="id-lock-registration" title="Free registration required"><a rel="nofollow" class="external text" href="https://archive.org/details/isbn_9780323057479/page/240"><i>Mosby's Manual of Diagnostic and Laboratory Tests</i></a></span>. St. Louis: Mosby. pp. <a rel="nofollow" class="external text" href="https://archive.org/details/isbn_9780323057479/page/240">240</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-323-05747-9" title="Special:BookSources/978-0-323-05747-9"><bdi>978-0-323-05747-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Mosby%27s+Manual+of+Diagnostic+and+Laboratory+Tests&rft.place=St.+Louis&rft.pages=240&rft.pub=Mosby&rft.date=2009&rft.isbn=978-0-323-05747-9&rft.aulast=Pagana&rft.aufirst=TJ&rft.au=Pagana%2C+KD&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fisbn_9780323057479%2Fpage%2F240&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstriol" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estriol&action=edit&section=14" title="Edit section: Further reading"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMerrill1958" class="citation journal cs1">Merrill RC (July 1958). "Estriol: a review". <i>Physiological Reviews</i>. <b>38</b> (3): <span class="nowrap">463–</span>80. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1152%2Fphysrev.1958.38.3.463">10.1152/physrev.1958.38.3.463</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/13567043">13567043</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Physiological+Reviews&rft.atitle=Estriol%3A+a+review&rft.volume=38&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E463-%3C%2Fspan%3E80&rft.date=1958-07&rft_id=info%3Adoi%2F10.1152%2Fphysrev.1958.38.3.463&rft_id=info%3Apmid%2F13567043&rft.aulast=Merrill&rft.aufirst=RC&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstriol" class="Z3988"></span></li></ul> <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></div><div role="navigation" class="navbox" aria-labelledby="Endogenous_steroids141" 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:Steroid_hormones" title="Template:Steroid hormones"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Steroid_hormones" title="Template talk:Steroid hormones"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Steroid_hormones" title="Special:EditPage/Template:Steroid hormones"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Endogenous_steroids141" style="font-size:114%;margin:0 4em"><a href="/wiki/Endogenous" class="mw-redirect" title="Endogenous">Endogenous</a> <a href="/wiki/Steroid" title="Steroid">steroids</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">Precursors</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></li> <li><a href="/wiki/22R-Hydroxycholesterol" title="22R-Hydroxycholesterol">22<i>R</i>-Hydroxycholesterol</a></li> <li><a href="/wiki/20%CE%B1,22R-Dihydroxycholesterol" title="20α,22R-Dihydroxycholesterol">20α,22<i>R</i>-Dihydroxycholesterol</a></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a></li> <li><a href="/w/index.php?title=11%CE%B2-Hydroxypregnenolone&action=edit&redlink=1" class="new" title="11β-Hydroxypregnenolone (page does not exist)">11β-Hydroxypregnenolone</a></li> <li><a href="/wiki/17%CE%B1-Hydroxypregnenolone" title="17α-Hydroxypregnenolone">17α-Hydroxypregnenolone</a></li> <li><a href="/wiki/21-Hydroxypregnenolone" title="21-Hydroxypregnenolone">21-Hydroxypregnenolone</a></li> <li><a href="/w/index.php?title=17%CE%B1,21-Dihydroxypregnenolone&action=edit&redlink=1" class="new" title="17α,21-Dihydroxypregnenolone (page does not exist)">17α,21-Dihydroxypregnenolone</a></li> <li><a href="/w/index.php?title=11%CE%B2,17%CE%B1,21-Trihydroxypregnenolone&action=edit&redlink=1" class="new" title="11β,17α,21-Trihydroxypregnenolone (page does not exist)">11β,17α,21-Trihydroxypregnenolone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Corticosteroid" title="Corticosteroid">Corticosteroids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" 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:1%"><a href="/wiki/Glucocorticoid" title="Glucocorticoid">Glucocorticoids</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Tetrahydrocorticosterone" title="Tetrahydrocorticosterone">3α,5α-Tetrahydrocorticosterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydrocorticosterone" title="5α-Dihydrocorticosterone">5α-Dihydrocorticosterone</a></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone</a></li> <li><a href="/wiki/11-Deoxycortisol" title="11-Deoxycortisol">11-Deoxycortisol</a></li> <li><a href="/wiki/11-Ketoprogesterone" title="11-Ketoprogesterone">11-Ketoprogesterone</a></li> <li><a href="/wiki/21-Deoxycortisol" title="21-Deoxycortisol">21-Deoxycortisol</a></li> <li><a href="/wiki/21-Deoxycortisone" title="21-Deoxycortisone">21-Deoxycortisone</a></li> <li><a href="/wiki/Corticosterone" title="Corticosterone">Corticosterone</a></li> <li><a href="/wiki/Cortisol" title="Cortisol">Cortisol</a></li> <li><a href="/wiki/Cortisone" title="Cortisone">Cortisone</a></li> <li><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/Pregnenolone" title="Pregnenolone">Pregnenolone</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li></ul> <ul><li><i>Metabolites:</i> <a href="/wiki/5%CE%B1-Dihydrocortisol" title="5α-Dihydrocortisol">5α-Dihydrocortisol</a></li> <li><a href="/w/index.php?title=3%CE%B1,5%CE%B1-Tetrahydrocortisol&action=edit&redlink=1" class="new" title="3α,5α-Tetrahydrocortisol (page does not exist)">3α,5α-Tetrahydrocortisol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Mineralocorticoid" title="Mineralocorticoid">Mineralocorticoids</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 href="/wiki/5%CE%B1-Dihydroaldosterone" title="5α-Dihydroaldosterone">5α-Dihydroaldosterone</a></li> <li><a href="/wiki/11-Dehydrocorticosterone" title="11-Dehydrocorticosterone">11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone)</a></li> <li><a href="/wiki/11-Deoxycortisol" title="11-Deoxycortisol">11-Deoxycortisol</a></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone</a></li> <li><a href="/wiki/11%CE%B2-Hydroxyprogesterone" title="11β-Hydroxyprogesterone">11β-Hydroxyprogesterone (21-deoxycorticosterone)</a></li> <li><a href="/wiki/18-Hydroxy-11-deoxycorticosterone" title="18-Hydroxy-11-deoxycorticosterone">18-Hydroxy-11-deoxycorticosterone</a></li> <li><a href="/wiki/18-Hydroxycorticosterone" title="18-Hydroxycorticosterone">18-Hydroxycorticosterone</a></li> <li><a href="/w/index.php?title=18-Hydroxyprogesterone&action=edit&redlink=1" class="new" title="18-Hydroxyprogesterone (page does not exist)">18-Hydroxyprogesterone</a></li> <li><a href="/wiki/Aldosterone" title="Aldosterone">Aldosterone</a></li> <li><a href="/wiki/Corticosterone" title="Corticosterone">Corticosterone</a></li> <li><a href="/wiki/Cortisol" title="Cortisol">Cortisol</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sex_steroid" class="mw-redirect" title="Sex steroid">Sex steroids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" 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:1%"><a href="/wiki/Androgen" title="Androgen">Androgens</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/11-Ketodihydrotestosterone" title="11-Ketodihydrotestosterone">11-Ketodihydrotestosterone</a></li> <li><a href="/wiki/11-Ketotestosterone" title="11-Ketotestosterone">11-Ketotestosterone</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/11%CE%B2-Hydroxyandrostenedione" title="11β-Hydroxyandrostenedione">11β-Hydroxyandrostenedione</a></li> <li><a href="/wiki/Adrenosterone" title="Adrenosterone">Adrenosterone (11-ketoandrostenedione)</a></li> <li><a href="/wiki/Androstenediol" title="Androstenediol">Androstenediol</a></li> <li><a href="/wiki/Androstenedione" title="Androstenedione">Androstenedione</a></li> <li><a href="/wiki/Androsterone" title="Androsterone">Androsterone</a></li> <li><a href="/wiki/Dehydroandrosterone" title="Dehydroandrosterone">Dehydroandrosterone</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA sulfate</a></li> <li><a href="/wiki/Dihydrotestosterone" title="Dihydrotestosterone">Dihydrotestosterone</a></li> <li><a href="/wiki/Epiandrosterone" title="Epiandrosterone">Epiandrosterone</a></li> <li><a href="/wiki/Epitestosterone" title="Epitestosterone">Epitestosterone</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyandrostenedione" title="16α-Hydroxyandrostenedione">16α-Hydroxyandrostenedione</a></li> <li><a href="/wiki/16-Hydroxydehydroepiandrosterone" class="mw-redirect" title="16-Hydroxydehydroepiandrosterone">16α-Hydroxy-DHEA</a></li> <li><a href="/wiki/16-Hydroxydehydroepiandrosterone_sulfate" class="mw-redirect" title="16-Hydroxydehydroepiandrosterone sulfate">16α-Hydroxy-DHEA sulfate</a></li> <li><a href="/wiki/Testosterone" title="Testosterone">Testosterone</a></li></ul> <ul><li><i>Metabolites:</i> <a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/wiki/3%CE%B1-Androstanediol_glucuronide" class="mw-redirect" title="3α-Androstanediol glucuronide">3α-Androstanediol glucuronide</a></li> <li><a href="/wiki/3%CE%B2-Androstanediol" title="3β-Androstanediol">3β-Androstanediol</a></li> <li><a href="/wiki/5%CE%B2-Dihydrotestosterone" title="5β-Dihydrotestosterone">5β-Dihydrotestosterone</a></li> <li><a href="/wiki/3%CE%B1-Etiocholanediol" title="3α-Etiocholanediol">3α-Etiocholanediol</a></li> <li><a href="/wiki/3%CE%B2-Etiocholanediol" title="3β-Etiocholanediol">3β-Etiocholanediol</a></li> <li><a href="/w/index.php?title=Androstanetriol&action=edit&redlink=1" class="new" title="Androstanetriol (page does not exist)">Androstanetriols</a></li> <li><a href="/wiki/Androstenediol_sulfate" title="Androstenediol sulfate">Androstenediol sulfate</a></li> <li><a href="/wiki/Androstenetriol" title="Androstenetriol">Androstenetriol</a></li> <li><a href="/wiki/Androsterone_glucuronide" title="Androsterone glucuronide">Androsterone glucuronide</a></li> <li><a href="/wiki/Androsterone_sulfate" title="Androsterone sulfate">Androsterone sulfate</a></li> <li><a href="/w/index.php?title=Dihydrotestosterone_glucuronide&action=edit&redlink=1" class="new" title="Dihydrotestosterone glucuronide (page does not exist)">Dihydrotestosterone glucuronide</a></li> <li><a href="/w/index.php?title=Dihydrotestosterone_sulfate&action=edit&redlink=1" class="new" title="Dihydrotestosterone sulfate (page does not exist)">Dihydrotestosterone sulfate</a></li> <li><a href="/wiki/Etiocholanedione" title="Etiocholanedione">Etiocholanedione</a></li> <li><a href="/wiki/Etiocholanolone" title="Etiocholanolone">Etiocholanolone</a></li> <li><a href="/wiki/Etiocholanolone_glucuronide" title="Etiocholanolone glucuronide">Etiocholanolone glucuronide</a></li> <li><a href="/wiki/Epietiocholanolone" title="Epietiocholanolone">Epietiocholanolone</a></li> <li><a href="/wiki/Testosterone_glucuronide" title="Testosterone glucuronide">Testosterone glucuronide</a></li> <li><a href="/wiki/Testosterone_sulfate" title="Testosterone sulfate">Testosterone sulfate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Estrogen" title="Estrogen">Estrogens</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><i>Estranes:</i> <a href="/wiki/Estetrol" title="Estetrol">Estetrol</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/wiki/Estrone" title="Estrone">Estrone</a></li> <li><a class="mw-selflink selflink">Estriol</a></li> <li><a href="/wiki/17%CE%B1-Estradiol" title="17α-Estradiol">17α-Estradiol</a></li> <li><a href="/wiki/Epiestriol" title="Epiestriol">16β-Epiestriol (16β-hydroxyestradiol)</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/16%CE%B2,17%CE%B1-Epiestriol" title="16β,17α-Epiestriol">16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)</a></li> <li><a href="/wiki/2-Hydroxyestradiol" title="2-Hydroxyestradiol">2-Hydroxyestradiol</a></li> <li><a href="/wiki/2-Hydroxyestriol" title="2-Hydroxyestriol">2-Hydroxyestriol</a></li> <li><a href="/wiki/2-Hydroxyestrone" title="2-Hydroxyestrone">2-Hydroxyestrone</a></li> <li><a href="/wiki/4-Hydroxyestradiol" title="4-Hydroxyestradiol">4-Hydroxyestradiol</a></li> <li><a href="/wiki/4-Hydroxyestriol" title="4-Hydroxyestriol">4-Hydroxyestriol</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/16%CE%B1-Hydroxyestrone" title="16α-Hydroxyestrone">16α-Hydroxyestrone</a></li> <li><a href="/wiki/16%CE%B2-Hydroxyestrone" title="16β-Hydroxyestrone">16β-Hydroxyestrone</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></ul> <ul><li><i>Others:</i> <a href="/wiki/27-Hydroxycholesterol" title="27-Hydroxycholesterol">27-Hydroxycholesterol</a></li> <li><a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/wiki/3%CE%B2-Androstanediol" title="3β-Androstanediol">3β-Androstanediol</a></li> <li><a href="/wiki/4-Androstenedione" class="mw-redirect" title="4-Androstenedione">4-Androstenedione</a></li> <li><a href="/wiki/5-Androstenediol" class="mw-redirect" title="5-Androstenediol">5-Androstenediol</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA sulfate</a></li> <li><a href="/wiki/7-Keto-DHEA" title="7-Keto-DHEA">7-Keto-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/16-Hydroxydehydroepiandrosterone" class="mw-redirect" title="16-Hydroxydehydroepiandrosterone">16α-Hydroxy-DHEA</a></li></ul> <ul><li><i>Metabolites:</i> <a href="/wiki/2-Methoxyestradiol" title="2-Methoxyestradiol">2-Methoxyestradiol</a></li> <li><a href="/wiki/2-Methoxyestrone" title="2-Methoxyestrone">2-Methoxyestrone</a></li> <li><a href="/wiki/2-Methoxyestriol" title="2-Methoxyestriol">2-Methoxyestriol</a></li> <li><a href="/wiki/4-Methoxyestriol" title="4-Methoxyestriol">4-Methoxyestriol</a></li> <li><a href="/wiki/Estradiol_disulfate" title="Estradiol disulfate">Estradiol disulfate</a></li> <li><a href="/wiki/Estradiol_glucuronide" title="Estradiol glucuronide">Estradiol glucuronide</a></li> <li><a href="/wiki/Estradiol_3-glucuronide" title="Estradiol 3-glucuronide">Estradiol 3-glucuronide</a></li> <li><a href="/wiki/Estradiol_3-glucuronide_17%CE%B2-sulfate" title="Estradiol 3-glucuronide 17β-sulfate">Estradiol 3-glucuronide 17β-sulfate</a></li> <li><a href="/wiki/Estradiol_sulfate" title="Estradiol sulfate">Estradiol sulfate</a></li> <li><a href="/wiki/Estradiol_17%CE%B2-sulfate" title="Estradiol 17β-sulfate">Estradiol 17β-sulfate</a></li> <li><a href="/wiki/Estrone_glucuronide" title="Estrone glucuronide">Estrone glucuronide</a></li> <li><a href="/wiki/Estrone_sulfate" title="Estrone sulfate">Estrone sulfate</a></li> <li><a href="/wiki/Estriol_glucuronide" title="Estriol glucuronide">Estriol glucuronide</a></li> <li><a href="/wiki/Estriol_sulfate" title="Estriol sulfate">Estriol sulfate</a></li> <li><a href="/wiki/Lipoidal_estradiol" title="Lipoidal estradiol">Lipoidal estradiol</a> (e.g., <a href="/wiki/Estradiol_stearate" title="Estradiol stearate">estradiol stearate</a>, <a href="/wiki/Estradiol_palmitate" title="Estradiol palmitate">estradiol palmitate</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Progestogen" title="Progestogen">Progestogens</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyprogesterone" title="16α-Hydroxyprogesterone">16α-Hydroxyprogesterone</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone</a></li> <li><a href="/wiki/20%CE%B1-Dihydroprogesterone" title="20α-Dihydroprogesterone">20α-Dihydroprogesterone</a></li> <li><a href="/wiki/20%CE%B2-Dihydroprogesterone" title="20β-Dihydroprogesterone">20β-Dihydroprogesterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">5α-Dihydroprogesterone</a></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone</a></li> <li><a href="/wiki/Dihydrodeoxycorticosterone" title="Dihydrodeoxycorticosterone">5α-DHDOC</a></li></ul> <ul><li><i>Metabolites:</i> <a href="/wiki/Allopregnanediol" title="Allopregnanediol">Allopregnanediol</a></li> <li><a href="/wiki/Pregnanediol" title="Pregnanediol">Pregnanediol</a></li> <li><a href="/wiki/Pregnanediol_glucuronide" title="Pregnanediol glucuronide">Pregnanediol glucuronide</a></li> <li><a href="/wiki/Pregnanetriol" title="Pregnanetriol">Pregnanetriol</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Neuroactive_steroid" class="mw-redirect" title="Neuroactive steroid">Neurosteroids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Cholestanes:</i> <a href="/wiki/24S-hydroxycholesterol" class="mw-redirect" title="24S-hydroxycholesterol">24<i>S</i>-Hydroxycholesterol</a></li> <li><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></li></ul> <ul><li><i>Pregnanes:</i> <a href="/wiki/3%CE%B1-Dihydroprogesterone" title="3α-Dihydroprogesterone">3α-Dihydroprogesterone</a></li> <li><a href="/wiki/3%CE%B2-Dihydroprogesterone" title="3β-Dihydroprogesterone">3β-Dihydroprogesterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydrocorticosterone" title="5α-Dihydrocorticosterone">5α-Dihydrocorticosterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">5α-Dihydroprogesterone</a></li> <li><a href="/wiki/5%CE%B2-Dihydroprogesterone" title="5β-Dihydroprogesterone">5β-Dihydroprogesterone</a></li> <li><a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone</a></li> <li><a href="/wiki/Corticosterone" title="Corticosterone">Corticosterone</a></li> <li><a href="/wiki/Dihydrocorticosterone" class="mw-redirect" title="Dihydrocorticosterone">DHC</a></li> <li><a href="/wiki/Dihydrodeoxycorticosterone" title="Dihydrodeoxycorticosterone">DHDOC</a></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone</a></li> <li><a href="/wiki/Epipregnanolone" title="Epipregnanolone">Epipregnanolone</a></li> <li><a href="/wiki/Isopregnanolone" title="Isopregnanolone">Isopregnanolone</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_sulfate" title="Pregnenolone sulfate">Pregnenolone sulfate</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Tetrahydrocorticosterone" title="Tetrahydrocorticosterone">THB</a></li> <li><a href="/wiki/Tetrahydrodeoxycorticosterone" title="Tetrahydrodeoxycorticosterone">THDOC</a></li></ul> <ul><li><i>Androstanes:</i> <a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/wiki/3%CE%B1-Androstenol" class="mw-redirect" title="3α-Androstenol">3α-Androstenol</a></li> <li><a href="/wiki/7-Keto-DHEA" title="7-Keto-DHEA">7-Keto-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%B2-Hydroxy-DHEA" title="7β-Hydroxy-DHEA">7β-Hydroxy-DHEA</a></li> <li><a href="/wiki/7%CE%B1-Hydroxyepiandrosterone" title="7α-Hydroxyepiandrosterone">7α-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/Androsterone" title="Androsterone">Androsterone</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA sulfate</a></li> <li><a href="/wiki/Etiocholanolone" title="Etiocholanolone">Etiocholanolone</a></li></ul> <ul><li><b><a href="/wiki/Pheromone" title="Pheromone">Pheromones</a>:</b> <a href="/wiki/3%CE%B1-Androstenol" class="mw-redirect" title="3α-Androstenol">3α-Androstenol</a></li> <li><a href="/wiki/3%CE%B2-Androstenol" title="3β-Androstenol">3β-Androstenol</a></li> <li><a href="/wiki/Androstadienol" title="Androstadienol">Androstadienol</a></li> <li><a href="/wiki/Androstadienone" title="Androstadienone">Androstadienone</a></li> <li><a href="/wiki/Androstenone" title="Androstenone">Androstenone</a></li> <li><a href="/wiki/Androsterone" title="Androsterone">Androsterone</a></li> <li><a href="/wiki/Estratetraenol" title="Estratetraenol">Estratetraenol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b><a href="/wiki/Vitamin_D" title="Vitamin D">Vitamin D</a>:</b> <a href="/wiki/7-Dehydrocholesterol" title="7-Dehydrocholesterol">7-Dehydrocholesterol</a></li> <li><a href="/wiki/Calcifediol" title="Calcifediol">Calcidiol/Calcifediol</a></li> <li><a href="/wiki/Calcitriol" title="Calcitriol">Calcitriol</a></li> <li><a href="/wiki/Cholecalciferol" title="Cholecalciferol">Cholecalciferol</a></li></ul> <ul><li><b>Others:</b> <a href="/wiki/7%CE%B1-Hydroxycholesterol" title="7α-Hydroxycholesterol">7α-Hydroxycholesterol</a></li> <li><a href="/wiki/11%CE%B1-Hydroxyprogesterone" title="11α-Hydroxyprogesterone">11α-Hydroxyprogesterone</a></li> <li><a href="/wiki/11%CE%B2-Hydroxyprogesterone" title="11β-Hydroxyprogesterone">11β-Hydroxyprogesterone</a></li> <li><a href="/wiki/Cholesterol_sulfate" title="Cholesterol sulfate">Cholesterol sulfate</a></li></ul> </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_modulators1222" 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_modulators1222" 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</span></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><i>Steroidal:</i> <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"><i>ent</i>-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 class="mw-selflink selflink">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 href="/wiki/Ethinylestradiol" title="Ethinylestradiol">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><i>Nonsteroidal:</i> <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"><i>meso</i>-Butestrol</a></li> <li><a href="/wiki/Meso-Hexestrol" class="mw-redirect" title="Meso-Hexestrol"><i>meso</i>-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><i>Unknown/unsorted:</i> <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><i>Xenoestrogens:</i> <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 (<i>cis</i>-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<br />(<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</span>)</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><i>Coregulator-binding modulators:</i> <a href="/wiki/ERX-11" title="ERX-11">ERX-11</a></li></ul> <ul><li><i>Noncompetitive inhibitors:</i> <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</span></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 href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a></li> <li><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant (ICI-182780)</a></li> <li><a href="/wiki/G-1_(drug)" class="mw-redirect" title="G-1 (drug)">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/Nicotinic_acid" title="Nicotinic acid">Nicotinic acid</a></li> <li><a href="/wiki/Nicotinamide" title="Nicotinamide">Nicotinamide</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 class="mw-selflink selflink">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><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" 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=Estriol&oldid=1267297848">https://en.wikipedia.org/w/index.php?title=Estriol&oldid=1267297848</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:Estranes" title="Category:Estranes">Estranes</a></li><li><a href="/wiki/Category:Estrogens" title="Category:Estrogens">Estrogens</a></li><li><a href="/wiki/Category:GPER_antagonists" title="Category:GPER antagonists">GPER antagonists</a></li><li><a href="/wiki/Category:Hormones_of_the_hypothalamus-pituitary-gonad_axis" title="Category:Hormones of the hypothalamus-pituitary-gonad axis">Hormones of the hypothalamus-pituitary-gonad axis</a></li><li><a href="/wiki/Category:Hormones_of_the_pregnant_female" title="Category:Hormones of the pregnant female">Hormones of the pregnant female</a></li><li><a href="/wiki/Category:Hydroxyarenes" title="Category:Hydroxyarenes">Hydroxyarenes</a></li><li><a href="/wiki/Category:Sex_hormones" title="Category:Sex hormones">Sex hormones</a></li><li><a href="/wiki/Category:Triols" title="Category:Triols">Triols</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_March_2024" title="Category:Articles with dead external links from March 2024">Articles with dead external links from March 2024</a></li><li><a href="/wiki/Category:Articles_with_permanently_dead_external_links" title="Category:Articles with permanently dead external links">Articles with permanently dead external links</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:Articles_containing_unverified_chemical_infoboxes" title="Category:Articles containing unverified chemical infoboxes">Articles containing unverified chemical infoboxes</a></li><li><a href="/wiki/Category:Chembox_image_size_set" title="Category:Chembox image size set">Chembox image size set</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_matches_Wikidata" title="Category:Short description matches Wikidata">Short description matches 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_October_2016" title="Category:Articles with unsourced statements from October 2016">Articles with unsourced statements from October 2016</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 4 January 2025, at 13:46<span class="anonymous-show"> (UTC)</span>.</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=Estriol&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"><picture><source media="(min-width: 500px)" srcset="/static/images/footer/wikimedia-button.svg" width="84" height="29"><img src="/static/images/footer/wikimedia.svg" width="25" height="25" alt="Wikimedia Foundation" lang="en" loading="lazy"></picture></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"><picture><source media="(min-width: 500px)" srcset="/w/resources/assets/poweredby_mediawiki.svg" width="88" height="31"><img src="/w/resources/assets/mediawiki_compact.svg" alt="Powered by MediaWiki" lang="en" width="25" height="25" loading="lazy"></picture></a></li> </ul> </footer> </div> </div> </div> <div class="vector-header-container vector-sticky-header-container"> <div id="vector-sticky-header" class="vector-sticky-header"> <div class="vector-sticky-header-start"> <div class="vector-sticky-header-icon-start vector-button-flush-left vector-button-flush-right" aria-hidden="true"> <button class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-sticky-header-search-toggle" tabindex="-1" data-event-name="ui.vector-sticky-search-form.icon"><span class="vector-icon mw-ui-icon-search mw-ui-icon-wikimedia-search"></span> <span>Search</span> </button> </div> <div role="search" class="vector-search-box-vue vector-search-box-show-thumbnail vector-search-box"> <div class="vector-typeahead-search-container"> <div class="cdx-typeahead-search cdx-typeahead-search--show-thumbnail"> <form action="/w/index.php" id="vector-sticky-search-form" class="cdx-search-input cdx-search-input--has-end-button"> <div 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"> <span class="cdx-text-input__icon cdx-text-input__start-icon"></span> </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> <div class="vector-sticky-header-context-bar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-sticky-header-toc" class="vector-dropdown mw-portlet mw-portlet-sticky-header-toc vector-sticky-header-toc vector-button-flush-left" > <input type="checkbox" id="vector-sticky-header-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-sticky-header-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-sticky-header-toc-label" for="vector-sticky-header-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" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-sticky-header-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <div class="vector-sticky-header-context-bar-primary" aria-hidden="true" ><span class="mw-page-title-main">Estriol</span></div> </div> </div> <div class="vector-sticky-header-end" aria-hidden="true"> <div class="vector-sticky-header-icons"> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-talk-sticky-header" tabindex="-1" data-event-name="talk-sticky-header"><span class="vector-icon mw-ui-icon-speechBubbles mw-ui-icon-wikimedia-speechBubbles"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-subject-sticky-header" tabindex="-1" data-event-name="subject-sticky-header"><span class="vector-icon mw-ui-icon-article mw-ui-icon-wikimedia-article"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-history-sticky-header" tabindex="-1" data-event-name="history-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-history mw-ui-icon-wikimedia-wikimedia-history"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only mw-watchlink" id="ca-watchstar-sticky-header" tabindex="-1" data-event-name="watch-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-star mw-ui-icon-wikimedia-wikimedia-star"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-edit-sticky-header" tabindex="-1" data-event-name="wikitext-edit-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-wikiText mw-ui-icon-wikimedia-wikimedia-wikiText"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-ve-edit-sticky-header" tabindex="-1" data-event-name="ve-edit-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-edit mw-ui-icon-wikimedia-wikimedia-edit"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-viewsource-sticky-header" tabindex="-1" data-event-name="ve-edit-protected-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-editLock mw-ui-icon-wikimedia-wikimedia-editLock"></span> <span></span> </a> </div> <div class="vector-sticky-header-buttons"> <button class="cdx-button cdx-button--weight-quiet mw-interlanguage-selector" id="p-lang-btn-sticky-header" tabindex="-1" data-event-name="ui.dropdown-p-lang-btn-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-language mw-ui-icon-wikimedia-wikimedia-language"></span> <span>26 languages</span> </button> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive" id="ca-addsection-sticky-header" tabindex="-1" data-event-name="addsection-sticky-header"><span class="vector-icon mw-ui-icon-speechBubbleAdd-progressive mw-ui-icon-wikimedia-speechBubbleAdd-progressive"></span> <span>Add topic</span> </a> </div> <div class="vector-sticky-header-icon-end"> <div class="vector-user-links"> </div> </div> </div> </div> </div> <div class="mw-portlet mw-portlet-dock-bottom emptyPortlet" id="p-dock-bottom"> <ul> </ul> </div> <script>(RLQ=window.RLQ||[]).push(function(){mw.config.set({"wgHostname":"mw-web.eqiad.main-78bdfcd464-rvnbh","wgBackendResponseTime":207,"wgPageParseReport":{"limitreport":{"cputime":"0.823","walltime":"1.172","ppvisitednodes":{"value":8234,"limit":1000000},"postexpandincludesize":{"value":250328,"limit":2097152},"templateargumentsize":{"value":25475,"limit":2097152},"expansiondepth":{"value":18,"limit":100},"expensivefunctioncount":{"value":6,"limit":500},"unstrip-depth":{"value":1,"limit":20},"unstrip-size":{"value":156636,"limit":5000000},"entityaccesscount":{"value":1,"limit":400},"timingprofile":["100.00% 962.927 1 -total"," 36.41% 350.572 1 Template:Chembox"," 25.93% 249.640 1 Template:Reflist"," 22.56% 217.283 1 Template:Chembox_Identifiers"," 14.65% 141.070 1 Template:Selected_biological_properties_of_endogenous_estrogens_in_rats"," 11.50% 110.695 3 Template:Chembox_headerbar"," 11.21% 107.906 9 Template:Trim"," 10.67% 102.722 22 Template:No_selflink"," 10.30% 99.215 7 Template:Cite_journal"," 9.78% 94.205 22 Template:Cite_book"]},"scribunto":{"limitreport-timeusage":{"value":"0.414","limit":"10.000"},"limitreport-memusage":{"value":8398783,"limit":52428800}},"cachereport":{"origin":"mw-web.eqiad.main-8669bc5c8-q5ww2","timestamp":"20250318160328","ttl":2592000,"transientcontent":false}}});});</script> <script type="application/ld+json">{"@context":"https:\/\/schema.org","@type":"Article","name":"Estriol","url":"https:\/\/en.wikipedia.org\/wiki\/Estriol","sameAs":"http:\/\/www.wikidata.org\/entity\/Q409721","mainEntity":"http:\/\/www.wikidata.org\/entity\/Q409721","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":"2004-05-11T02:01:02Z","dateModified":"2025-01-04T13:46:38Z","image":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/8\/82\/Estriol.svg","headline":"chemical compound"}</script> </body> </html>