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id="toc-Medical_uses-sublist" class="vector-toc-list"> <li id="toc-Reproductive_medicine" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Reproductive_medicine"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>Reproductive medicine</span> </div> </a> <ul id="toc-Reproductive_medicine-sublist" class="vector-toc-list"> <li id="toc-Testosterone_replacement_therapy" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Testosterone_replacement_therapy"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1.1</span> <span>Testosterone replacement therapy</span> </div> </a> <ul id="toc-Testosterone_replacement_therapy-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Gynecomastia" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Gynecomastia"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1.2</span> <span>Gynecomastia</span> </div> 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class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Side effects</span> </div> </a> <button aria-controls="toc-Side_effects-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 Side effects subsection</span> </button> <ul id="toc-Side_effects-sublist" class="vector-toc-list"> <li id="toc-Cancer_risk" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cancer_risk"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Cancer risk</span> </div> </a> <ul id="toc-Cancer_risk-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Pharmacology" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Pharmacology"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Pharmacology</span> </div> </a> <button aria-controls="toc-Pharmacology-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 Pharmacology subsection</span> </button> <ul id="toc-Pharmacology-sublist" class="vector-toc-list"> <li id="toc-Pharmacodynamics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmacodynamics"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Pharmacodynamics</span> </div> </a> <ul id="toc-Pharmacodynamics-sublist" class="vector-toc-list"> <li id="toc-Selective_estrogen_receptor_modulator_activity" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Selective_estrogen_receptor_modulator_activity"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1.1</span> <span>Selective estrogen receptor modulator activity</span> </div> </a> <ul id="toc-Selective_estrogen_receptor_modulator_activity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_activities" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Other_activities"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1.2</span> <span>Other activities</span> </div> </a> <ul id="toc-Other_activities-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Pharmacokinetics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmacokinetics"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Pharmacokinetics</span> </div> </a> <ul id="toc-Pharmacokinetics-sublist" class="vector-toc-list"> </ul> </li> </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">6</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">7</span> <span>History</span> </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Society_and_culture" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Society_and_culture"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Society and culture</span> </div> </a> <button aria-controls="toc-Society_and_culture-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 Society and culture subsection</span> </button> <ul id="toc-Society_and_culture-sublist" class="vector-toc-list"> <li id="toc-Brand_names" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Brand_names"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.1</span> <span>Brand names</span> </div> </a> <ul id="toc-Brand_names-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Regulation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Regulation"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.2</span> <span>Regulation</span> </div> </a> <ul id="toc-Regulation-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Research" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Research"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Research</span> </div> </a> <ul id="toc-Research-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">10</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label 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Available in 27 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-27" 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">27 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/%D9%83%D9%84%D9%88%D9%85%D9%8A%D9%81%D9%8A%D9%86" title="كلوميفين – Arabic" lang="ar" hreflang="ar" data-title="كلوميفين" 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/%DA%A9%D9%84%D9%88%D9%85%DB%8C%D9%81%D9%86_%D8%B3%DB%8C%D8%AA%D8%B1%D8%A7%D8%AA" title="کلومیفن سیترات – South Azerbaijani" lang="azb" hreflang="azb" data-title="کلومیفن سیترات" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Clomifen" title="Clomifen – German" lang="de" hreflang="de" data-title="Clomifen" 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/Clomifeno" title="Clomifeno – Spanish" lang="es" hreflang="es" data-title="Clomifeno" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%DA%A9%D9%84%D9%88%D9%85%DB%8C%D9%81%D9%86_%D8%B3%DB%8C%D8%AA%D8%B1%D8%A7%D8%AA" title="کلومیفن سیترات – Persian" lang="fa" hreflang="fa" data-title="کلومیفن سیترات" 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/Clomif%C3%A8ne" title="Clomifène – French" lang="fr" hreflang="fr" data-title="Clomifène" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ha mw-list-item"><a href="https://ha.wikipedia.org/wiki/Clomifen" title="Clomifen – Hausa" lang="ha" hreflang="ha" data-title="Clomifen" data-language-autonym="Hausa" data-language-local-name="Hausa" class="interlanguage-link-target"><span>Hausa</span></a></li><li class="interlanguage-link interwiki-ia mw-list-item"><a href="https://ia.wikipedia.org/wiki/Clomifeno" title="Clomifeno – Interlingua" lang="ia" hreflang="ia" data-title="Clomifeno" data-language-autonym="Interlingua" data-language-local-name="Interlingua" class="interlanguage-link-target"><span>Interlingua</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Clomifene" title="Clomifene – Italian" lang="it" hreflang="it" data-title="Clomifene" 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%A7%D7%9C%D7%95%D7%9E%D7%99%D7%A4%D7%9F" title="קלומיפן – Hebrew" lang="he" hreflang="he" data-title="קלומיפן" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Klomifenas" title="Klomifenas – Lithuanian" lang="lt" hreflang="lt" data-title="Klomifenas" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%95%E0%B5%8D%E0%B4%B2%E0%B5%8B%E0%B4%AE%E0%B4%BF%E0%B4%AB%E0%B5%80%E0%B5%BB" title="ക്ലോമിഫീൻ – Malayalam" lang="ml" hreflang="ml" data-title="ക്ലോമിഫീൻ" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Clomifeen" title="Clomifeen – Dutch" lang="nl" hreflang="nl" data-title="Clomifeen" 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%AF%E3%83%AD%E3%83%9F%E3%83%95%E3%82%A7%E3%83%B3" title="クロミフェン – Japanese" lang="ja" hreflang="ja" data-title="クロミフェン" 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-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Klomifen" title="Klomifen – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Klomifen" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-or mw-list-item"><a href="https://or.wikipedia.org/wiki/%E0%AC%95%E0%AD%8D%E0%AC%B2%E0%AD%8B%E0%AC%AE%E0%AC%BF%E0%AC%AB%E0%AC%BF%E0%AC%A8" title="କ୍ଲୋମିଫିନ – Odia" lang="or" hreflang="or" data-title="କ୍ଲୋମିଫିନ" data-language-autonym="ଓଡ଼ିଆ" data-language-local-name="Odia" class="interlanguage-link-target"><span>ଓଡ଼ିଆ</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Klomifen" title="Klomifen – Polish" lang="pl" hreflang="pl" data-title="Klomifen" 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/Clomifeno" title="Clomifeno – Portuguese" lang="pt" hreflang="pt" data-title="Clomifeno" 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%9A%D0%BB%D0%BE%D0%BC%D0%B8%D1%84%D0%B5%D0%BD" title="Кломифен – Russian" lang="ru" hreflang="ru" data-title="Кломифен" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Klomifen" title="Klomifen – Slovenian" lang="sl" hreflang="sl" data-title="Klomifen" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Klomifen" title="Klomifen – Serbian" lang="sr" hreflang="sr" data-title="Klomifen" 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/Klomifen" title="Klomifen – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Klomifen" 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/Klomifeeni" title="Klomifeeni – Finnish" lang="fi" hreflang="fi" data-title="Klomifeeni" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Klomifen" title="Klomifen – Turkish" lang="tr" hreflang="tr" data-title="Klomifen" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Clomifene" title="Clomifene – Vietnamese" lang="vi" hreflang="vi" data-title="Clomifene" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E5%A4%9A%E4%BB%94%E4%B8%B8" title="多仔丸 – Cantonese" lang="yue" hreflang="yue" data-title="多仔丸" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E5%8F%AF%E6%B4%9B%E7%B1%B3%E5%88%86" title="可洛米分 – Chinese" lang="zh" hreflang="zh" data-title="可洛米分" 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/Q418730#sitelinks-wikipedia" title="Edit interlanguage 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searchaux" style="display:none">Infertility treatment for women</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Clonidine" title="Clonidine">Clonidine</a>.</div> <p class="mw-empty-elt"> </p> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Clomifene">Clomifene</span></caption><tbody><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><span typeof="mw:File"><a href="/wiki/File:Clomifene.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/24/Clomifene.svg/250px-Clomifene.svg.png" decoding="async" width="250" height="173" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/24/Clomifene.svg/375px-Clomifene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/24/Clomifene.svg/500px-Clomifene.svg.png 2x" data-file-width="1465" data-file-height="1015" /></a></span></td></tr><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><span typeof="mw:File"><a href="/wiki/File:Clomifene-based-on-xtal-3D-bs-17.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f9/Clomifene-based-on-xtal-3D-bs-17.png/250px-Clomifene-based-on-xtal-3D-bs-17.png" decoding="async" width="250" height="220" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f9/Clomifene-based-on-xtal-3D-bs-17.png/375px-Clomifene-based-on-xtal-3D-bs-17.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f9/Clomifene-based-on-xtal-3D-bs-17.png/500px-Clomifene-based-on-xtal-3D-bs-17.png 2x" data-file-width="2569" data-file-height="2256" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Clomid, Serophene, others<sup id="cite_ref-Brands_1-0" class="reference"><a href="#cite_note-Brands-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">Clomiphene; Chloramifene; Chloramiphene; MRL-41; MRL/41; NSC-35770</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/American_Society_of_Health-System_Pharmacists" title="American Society of Health-System Pharmacists">AHFS</a>/<a href="/wiki/Drugs.com" title="Drugs.com">Drugs.com</a></th><td class="infobox-data"><span title="www.drugs.com"><a rel="nofollow" class="external text" href="https://www.drugs.com/monograph/clomiphene-citrate.html">Monograph</a></span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Pregnancy_category" title="Pregnancy category">Pregnancy<br />category</a></th><td class="infobox-data"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"> <ul><li><small><abbr class="country-name" title="Australia">AU</abbr>:</small> B3</li> <li class="mw-empty-elt"></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of<br />administration</a></th><td class="infobox-data"><a href="/wiki/Oral_administration" title="Oral administration">By mouth</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_class" title="Drug class">Drug class</a></th><td class="infobox-data"><a href="/wiki/Selective_estrogen_receptor_modulator" title="Selective estrogen receptor modulator">Selective estrogen receptor modulator</a>; <a href="/wiki/Progonadotropin" title="Progonadotropin">Progonadotropin</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a href="/wiki/ATC_code_G03" title="ATC code G03">G03GB02</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=G03GB02">WHO</a></span>) </li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li><small><abbr class="country-name" title="Australia">AU</abbr>:</small> <a href="/wiki/Standard_for_the_Uniform_Scheduling_of_Medicines_and_Poisons#Schedule_4" title="Standard for the Uniform Scheduling of Medicines and Poisons">S4</a> (Prescription only)</li> <li><small><abbr class="country-name" title="United Kingdom">UK</abbr>:</small> <a href="/wiki/Prescription_drug" title="Prescription drug">POM</a> (Prescription only)</li> <li><small><abbr class="country-name" title="United States">US</abbr>:</small> <a href="/wiki/Prescription_drug" title="Prescription drug">℞-only</a></li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a></th><td class="infobox-data">High (>90%)</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_metabolism" title="Drug metabolism">Metabolism</a></th><td class="infobox-data"><a href="/wiki/Liver" title="Liver">Liver</a> <a href="/wiki/CYP2D6" title="CYP2D6">CYP2D6</a> (with <a href="/wiki/Enterohepatic_circulation" title="Enterohepatic circulation">enterohepatic circulation</a>)<sup id="cite_ref-pmid29516347_2-3" class="reference"><a href="#cite_note-pmid29516347-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Metabolite" title="Metabolite">Metabolites</a></th><td class="infobox-data">4-Hydroxyclomiphene (4-OH-CLO), 4-Hydroxy-N-desethylclomiphene (4-OH-DE-CLO)</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Biological_half-life" title="Biological half-life">Elimination <span class="nowrap">half-life</span></a></th><td class="infobox-data">4 – 7 days <sup id="cite_ref-pmid29516347_2-0" class="reference"><a href="#cite_note-pmid29516347-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid29159661_3-0" class="reference"><a href="#cite_note-pmid29159661-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-singledosekinetics_4-0" class="reference"><a href="#cite_note-singledosekinetics-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> <br /> <p>active metabolites: <br /> 4-OH-CLO : 13 - 34 hrs<sup id="cite_ref-pmid29516347_2-1" class="reference"><a href="#cite_note-pmid29516347-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> <br /> </p> 4-OH-DE-CLO : 15 - 37 hrs<sup id="cite_ref-pmid29516347_2-2" class="reference"><a href="#cite_note-pmid29516347-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Excretion" title="Excretion">Excretion</a></th><td class="infobox-data">Mainly <a href="/wiki/Feces" title="Feces">feces</a>, some in <a href="/wiki/Urine" title="Urine">urine</a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">(<i>E</i>,<i>Z</i>)-2-(4-(2-chloro-1,2-diphenylethenyl)phenoxy)-<i>N</i>,<i>N</i>-diethylethanamine</div></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=911-45-5">911-45-5</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <span style="font-weight:normal"><abbr title="Compound ID">CID</abbr></span></th><td class="infobox-data"><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/2800">2800</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Guide_to_Pharmacology" title="Guide to Pharmacology">IUPHAR/BPS</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=4159">4159</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB00882">DB00882</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.2698.html">2698</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/1HRS458QU2">1HRS458QU2</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/KEGG" title="KEGG">KEGG</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D07726">D07726</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3752">CHEBI:3752</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL2355051">ChEMBL2355051</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></th><td class="infobox-data"><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/DTXSID1022843">DTXSID1022843</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q418730#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><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.011.826">100.011.826</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q418730#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><th colspan="2" class="infobox-header" style="background:#ddd">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data"><span title="Carbon">C</span><sub>26</sub><span title="Hydrogen">H</span><sub>28</sub><span title="Chlorine">Cl</span><span title="Nitrogen">N</span><span title="Oxygen">O</span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data"><span class="nowrap"><span data-sort-value="7002405970000000000♠"></span>405.97</span> g·mol<sup>−1</sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=ClC%28c1ccccc1%29%3DC%28c2ccc%28OCCN%28CC%29CC%29cc2%29c3ccccc3">Interactive image</a></span></li></ul></div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">ClC(c1ccccc1)=C(c2ccc(OCCN(CC)CC)cc2)c3ccccc3</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">InChI=1S/C26H28ClNO/c1-3-28(4-2)19-20-29-24-17-15-22(16-18-24)25(21-11-7-5-8-12-21)26(27)23-13-9-6-10-14-23/h5-18H,3-4,19-20H2,1-2H3<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:GKIRPKYJQBWNGO-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-below"><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style><span class="nobold"> <sup><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup> <a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">(what is this?)</a></span><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488"><span class="nobold">  <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=460044105&page2=Clomifene">(verify)</a></span></span></td></tr></tbody></table> <p><b>Clomifene</b>, also known as <b>clomiphene</b>, is a medication used to treat <a href="/wiki/Infertility" title="Infertility">infertility</a> in women who <a href="/wiki/Anovulation" title="Anovulation">do not ovulate</a>, including those with <a href="/wiki/Polycystic_ovary_syndrome" title="Polycystic ovary syndrome">polycystic ovary syndrome</a>.<sup id="cite_ref-AHFS2016_5-0" class="reference"><a href="#cite_note-AHFS2016-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> It is taken <a href="/wiki/By_mouth" class="mw-redirect" title="By mouth">by mouth</a>.<sup id="cite_ref-AHFS2016_5-1" class="reference"><a href="#cite_note-AHFS2016-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>Common side effects include <a href="/wiki/Pelvic_pain" title="Pelvic pain">pelvic pain</a> and <a href="/wiki/Hot_flashes" class="mw-redirect" title="Hot flashes">hot flashes</a>.<sup id="cite_ref-AHFS2016_5-2" class="reference"><a href="#cite_note-AHFS2016-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Other side effects can include changes in vision, vomiting, trouble sleeping, <a href="/wiki/Ovarian_cancer" title="Ovarian cancer">ovarian cancer</a>, and <a href="/wiki/Seizures" class="mw-redirect" title="Seizures">seizures</a>.<sup id="cite_ref-AHFS2016_5-3" class="reference"><a href="#cite_note-AHFS2016-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-WHO2008_6-0" class="reference"><a href="#cite_note-WHO2008-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> It is not recommended in people with <a href="/wiki/Liver_disease" title="Liver disease">liver disease</a> or <a href="/wiki/Abnormal_vaginal_bleeding" class="mw-redirect" title="Abnormal vaginal bleeding">abnormal vaginal bleeding</a> of unknown cause or who are <a href="/wiki/Pregnant" class="mw-redirect" title="Pregnant">pregnant</a>.<sup id="cite_ref-WHO2008_6-1" class="reference"><a href="#cite_note-WHO2008-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-FDAlabel_7-0" class="reference"><a href="#cite_note-FDAlabel-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Clomifene is in the <a href="/wiki/Selective_estrogen_receptor_modulator" title="Selective estrogen receptor modulator">selective estrogen receptor modulator</a> (SERM) family of medication and is a nonsteroidal medication.<sup id="cite_ref-FDAlabel_7-1" class="reference"><a href="#cite_note-FDAlabel-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> It works by causing the release of <a href="/wiki/GnRH" class="mw-redirect" title="GnRH">GnRH</a> by the <a href="/wiki/Hypothalamus" title="Hypothalamus">hypothalamus</a>, and subsequently <a href="/wiki/Gonadotropin" title="Gonadotropin">gonadotropin</a> from the <a href="/wiki/Anterior_pituitary" title="Anterior pituitary">anterior pituitary</a>.<sup id="cite_ref-WHO2008_6-2" class="reference"><a href="#cite_note-WHO2008-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Clomifene was approved for medical use in the United States in 1967.<sup id="cite_ref-AHFS2016_5-4" class="reference"><a href="#cite_note-AHFS2016-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> It is on the <a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">World Health Organization's List of Essential Medicines</a>, under the category "Ovulation inducers" (Complementary List).<sup id="cite_ref-WHO21st_9-0" class="reference"><a href="#cite_note-WHO21st-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Its introduction began the era of <a href="/wiki/Assisted_reproductive_technology" title="Assisted reproductive technology">assisted reproductive technology</a>.<sup id="cite_ref-Hist_10-0" class="reference"><a href="#cite_note-Hist-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>Clomifene (particularly the purified enclomiphene isomer) has also been found to have a powerful ability to boost or restore testosterone levels in <a href="/wiki/Hypogonadism" title="Hypogonadism">hypogonadal</a> men.<sup id="cite_ref-Enclomiphene_citrate_for_the_treatm_11-0" class="reference"><a href="#cite_note-Enclomiphene_citrate_for_the_treatm-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> It can be used to enhance performance in sports and is banned by the <a href="/wiki/World_Anti-Doping_Agency" title="World Anti-Doping Agency">World Anti-Doping Agency</a>. </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="Medical_uses">Medical uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Clomifene&action=edit&section=1" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Reproductive_medicine">Reproductive medicine</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Clomifene&action=edit&section=2" title="Edit section: Reproductive medicine"><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">Further information: <a href="/wiki/Ovulation_induction" title="Ovulation induction">Ovulation induction</a> and <a href="/wiki/Feminizing_hormone_therapy#Fertility" title="Feminizing hormone therapy">Feminizing hormone therapy § Fertility</a></div> <p>Clomifene is one of several alternatives for inducing <a href="/wiki/Ovulation" title="Ovulation">ovulation</a> in those who are infertile due to <a href="/wiki/Anovulation" title="Anovulation">anovulation</a> or <a href="/wiki/Oligoovulation" class="mw-redirect" title="Oligoovulation">oligoovulation</a>.<sup id="cite_ref-Committee2013_12-0" class="reference"><a href="#cite_note-Committee2013-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> Evidence is lacking for the use of clomifene in those who are infertile without a known reason.<sup id="cite_ref-Hugh2010_13-0" class="reference"><a href="#cite_note-Hugh2010-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> In such cases, studies have observed a clinical pregnancy rate 5.6% per cycle with clomifene treatment vs. 1.3%–4.2% per cycle without treatment.<sup id="cite_ref-Committee2013_12-1" class="reference"><a href="#cite_note-Committee2013-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> Clomifene has also been used with other <a href="/wiki/Assisted_reproductive_technology" title="Assisted reproductive technology">assisted reproductive technology</a> to increase success rates of these other modalities.<sup id="cite_ref-Induction_14-0" class="reference"><a href="#cite_note-Induction-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>Clomifene has been effectively used to restore <a href="/wiki/Spermatogenesis" title="Spermatogenesis">spermatogenesis</a> in trans women looking to have biological children.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> The effect of feminizing hormone therapy on fertility is not clear, but it is known that it can prevent sperm production.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Testosterone_replacement_therapy">Testosterone replacement therapy</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Clomifene&action=edit&section=3" title="Edit section: Testosterone replacement therapy"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Clomifene is sometimes used in the treatment of male <a href="/wiki/Hypogonadism" title="Hypogonadism">hypogonadism</a> as an alternative to <a href="/wiki/Testosterone_replacement_therapy" class="mw-redirect" title="Testosterone replacement therapy">testosterone replacement therapy</a>.<sup id="cite_ref-BachNajari2016_17-0" class="reference"><a href="#cite_note-BachNajari2016-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup class="noprint Inline-Template noprint Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:No_original_research#Primary,_secondary_and_tertiary_sources" title="Wikipedia:No original research"><span title="This claim needs references to reliable secondary sources. (August 2023)">non-primary source needed</span></a></i>]</sup> It has been found to increase testosterone levels by 2- to 2.5-times in hypogonadal men at such dosages.<sup id="cite_ref-BachNajari2016_17-1" class="reference"><a href="#cite_note-BachNajari2016-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-TrostKhera2014_18-0" class="reference"><a href="#cite_note-TrostKhera2014-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Despite the use of questionnaires in testosterone replacement comparator trials being called into question, clomifene's lower cost, therapeutic benefits, and greater value towards hypogonadism improvement have been noted.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup class="noprint Inline-Template noprint Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:No_original_research#Primary,_secondary_and_tertiary_sources" title="Wikipedia:No original research"><span title="This claim needs references to reliable secondary sources. (August 2023)">non-primary source needed</span></a></i>]</sup> </p><p>Clomifene consists of two <a href="/wiki/Stereoisomers" class="mw-redirect" title="Stereoisomers">stereoisomers</a> in equal proportion: <a href="/wiki/Enclomifene" title="Enclomifene">enclomifene</a> and <a href="/wiki/Zuclomifene" title="Zuclomifene">zuclomifene</a>. Zuclomifene has pro-estrogenic properties, whereas enclomifene is pro-androgenic, i.e. it promotes testosterone production through stimulation of the <a href="/wiki/HPG_axis" class="mw-redirect" title="HPG axis">HPG axis</a>. For this reason, purified enclomifene isomer has been found to be twice as effective in boosting testosterone compared to the standard mix of both isomers.<sup id="cite_ref-Enclomiphene_citrate_for_the_treatm_11-1" class="reference"><a href="#cite_note-Enclomiphene_citrate_for_the_treatm-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Additionally, enclomifene has a <a href="/wiki/Half-life" title="Half-life">half-life</a> of just 10 hours,<sup id="cite_ref-singledosekinetics_4-1" class="reference"><a href="#cite_note-singledosekinetics-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> but zuclomifene has a half-life on the order of several days to a week, so if the goal is to boost testosterone, taking regular clomifene may produce far longer-lasting pro-estrogenic effects than pro-androgenic effects.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Gynecomastia">Gynecomastia</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Clomifene&action=edit&section=4" title="Edit section: Gynecomastia"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Clomifene has been used in the treatment of <a href="/wiki/Gynecomastia" title="Gynecomastia">gynecomastia</a>.<sup id="cite_ref-Becker2001_21-0" class="reference"><a href="#cite_note-Becker2001-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> It has been found to be useful in the treatment of some cases of gynecomastia but it is not as effective as <a href="/wiki/Tamoxifen" title="Tamoxifen">tamoxifen</a> or <a href="/wiki/Raloxifene" title="Raloxifene">raloxifene</a> for this indication.<sup id="cite_ref-AgrawalGanie2017_22-0" class="reference"><a href="#cite_note-AgrawalGanie2017-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> It has shown variable results for gynecomastia (probably because the zuclomifene isomer is estrogenic), and hence is not recommended for treatment of the condition.<sup id="cite_ref-pmid18622190_23-0" class="reference"><a href="#cite_note-pmid18622190-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> Pure enclomifene isomer is likely to be more effective than clomifene at treating gynecomastia, because of the lack of the zuclomifene isomer (as noted above).<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (May 2024)">medical citation needed</span></a></i>]</sup> </p><p>Due to its long half-life, zuclomifene can be detected in urine for at least 261 days after discontinuation<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> (261 days after discontinuation with a half-life of 30 days, there is still 0.24% of the peak level of zuclomifene being excreted, whereas with a half-life of 10 hours, enclomifene reaches the same 0.24% level in less than 4 days<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (May 2024)">medical citation needed</span></a></i>]</sup>). </p> <div class="mw-heading mw-heading2"><h2 id="Prohibited_use_in_sports">Prohibited use in sports</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Clomifene&action=edit&section=5" title="Edit section: Prohibited use in sports"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/World_Anti-Doping_Agency" title="World Anti-Doping Agency">World Anti-Doping Agency</a> (WADA) prohibits clomifene under category S4 of hormone and metabolic modulators. It can be present as an undeclared ingredient in black market products available online to enhance athletic performance. Like other substances with <a href="/wiki/Anabolic_steroid" title="Anabolic steroid">anabolic</a> properties, clomifene leads to increased muscle mass in males.<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><p>Because clomifene can enhance <a href="/wiki/Poultry_farming#Egg-laying_chickens" title="Poultry farming">egg production in hens</a>, athletes may inadvertently consume the substance through contaminated food. A WADA study found that clomifene given to laying hens migrates into their eggs but was able to develop a method of distinguishing egg ingestion from doping.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Contraindications">Contraindications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Clomifene&action=edit&section=6" title="Edit section: Contraindications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Contraindications include an allergy to the medication, pregnancy, prior liver problems, abnormal vaginal bleeding of unclear cause, ovarian cysts other than those due to polycystic ovarian syndrome, unmanaged adrenal or thyroid problems, and <a href="/wiki/Pituitary_tumors" class="mw-redirect" title="Pituitary tumors">pituitary tumors</a>.<sup id="cite_ref-FDAlabel_7-2" class="reference"><a href="#cite_note-FDAlabel-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Side_effects">Side effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Clomifene&action=edit&section=7" title="Edit section: Side effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The most common <a href="/wiki/Adverse_drug_reaction" title="Adverse drug reaction">adverse drug reaction</a> associated with the use of clomifene (>10% of people) is reversible ovarian enlargement.<sup id="cite_ref-FDAlabel_7-3" class="reference"><a href="#cite_note-FDAlabel-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>Less common effects (1–10% of people) include visual symptoms (blurred vision, <a href="/wiki/Diplopia" title="Diplopia">double vision</a>, floaters, <a href="/wiki/Photophobia" title="Photophobia">eye sensitivity to light</a>, <a href="/wiki/Scotomata" class="mw-redirect" title="Scotomata">scotomata</a>), headaches, vasomotor flushes (or <a href="/wiki/Hot_flash" title="Hot flash">hot flashes</a>), light sensitivity and pupil constriction, abnormal uterine bleeding and/or abdominal discomfort.<sup id="cite_ref-FDAlabel_7-4" class="reference"><a href="#cite_note-FDAlabel-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>Rare adverse events (<1% of people) include: <a href="/wiki/Hypertriglyceridemia" title="Hypertriglyceridemia">high blood level of triglycerides</a>, <a href="/wiki/Hepatitis" title="Hepatitis">liver inflammation</a>, reversible <a href="/wiki/Alopecia" class="mw-redirect" title="Alopecia">baldness</a> and/or <a href="/wiki/Ovarian_hyperstimulation_syndrome" title="Ovarian hyperstimulation syndrome">ovarian hyperstimulation syndrome</a>.<sup id="cite_ref-FDAlabel_7-5" class="reference"><a href="#cite_note-FDAlabel-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>Clomifene can lead to multiple ovulation, hence increasing the chance of <a href="/wiki/Twin" title="Twin">twins</a> (10% of births instead of ~1% in the general population) and <a href="/wiki/Multiple_birth" title="Multiple birth">triplets</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (May 2024)">medical citation needed</span></a></i>]</sup> </p><p>Rates of birth defects and miscarriages do not appear to change with the use of clomifene for fertility.<sup id="cite_ref-FDAlabel_7-6" class="reference"><a href="#cite_note-FDAlabel-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Clomifene has been associated with <a href="/wiki/Liver_abnormalities" class="mw-redirect" title="Liver abnormalities">liver abnormalities</a> and a couple of cases of <a href="/wiki/Hepatotoxicity" title="Hepatotoxicity">hepatotoxicity</a>.<sup id="cite_ref-CameronFeuer2012_27-0" class="reference"><a href="#cite_note-CameronFeuer2012-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Cancer_risk">Cancer risk</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Clomifene&action=edit&section=8" title="Edit section: Cancer risk"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Some studies have suggested that clomifene if used for more than a year may increase the risk of <a href="/wiki/Ovarian_cancer" title="Ovarian cancer">ovarian cancer</a>.<sup id="cite_ref-Hugh2010_13-1" class="reference"><a href="#cite_note-Hugh2010-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> This may only be the case in those who have never been and do not become pregnant.<sup id="cite_ref-Trabert_28-0" class="reference"><a href="#cite_note-Trabert-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> Subsequent studies have failed to support those findings.<sup id="cite_ref-Committee2013_12-2" class="reference"><a href="#cite_note-Committee2013-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p><p>Clomifene has been shown to be associated with an increased risk of malignant <a href="/wiki/Melanoma" title="Melanoma">melanomas</a> and <a href="/wiki/Thyroid_cancer" title="Thyroid cancer">thyroid cancer</a>.<sup id="cite_ref-pmid29159661_3-1" class="reference"><a href="#cite_note-pmid29159661-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Thyroid cancer risk was not associated with the number of pregnancies carried to viability.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Clomifene&action=edit&section=9" title="Edit section: Pharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Pharmacodynamics">Pharmacodynamics</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Clomifene&action=edit&section=10" title="Edit section: Pharmacodynamics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="Selective_estrogen_receptor_modulator_activity">Selective estrogen receptor modulator activity</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Clomifene&action=edit&section=11" title="Edit section: Selective estrogen receptor modulator activity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Clomifene is a <a href="/wiki/Nonsteroidal" title="Nonsteroidal">nonsteroidal</a> <a href="/wiki/Triphenylethylene" title="Triphenylethylene">triphenylethylene</a> <a href="/wiki/Chemical_derivative" class="mw-redirect" title="Chemical derivative">derivative</a> that acts as a <a href="/wiki/Selective_estrogen_receptor_modulator" title="Selective estrogen receptor modulator">selective estrogen receptor modulator</a> (SERM).<sup id="cite_ref-Induction_14-1" class="reference"><a href="#cite_note-Induction-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> It consists of a non-racemic mixture of <a href="/wiki/Zuclomifene" title="Zuclomifene">zuclomifene</a> (~38%) and <a href="/wiki/Enclomifene" title="Enclomifene">enclomifene</a> (~62%), each of which has unique <a href="/wiki/Pharmacology" title="Pharmacology">pharmacologic</a> properties.<sup id="cite_ref-:1_31-0" class="reference"><a href="#cite_note-:1-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> It is a mixed <a href="/wiki/Agonist" title="Agonist">agonist</a> and <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonist</a> of the <a href="/wiki/Estrogen_receptor" title="Estrogen receptor">estrogen receptor</a> (ER). Clomifene activates the <a href="/wiki/ER%CE%B1" class="mw-redirect" title="ERα">ERα</a> in the setting of low baseline <a href="/wiki/Estrogen" title="Estrogen">estrogen</a> levels and partially blocks the receptor in the context of high baseline estrogen levels.<sup id="cite_ref-TrostKhera2014_18-1" class="reference"><a href="#cite_note-TrostKhera2014-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Conversely, it is an <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonist</a> of the <a href="/wiki/ER%CE%B2" class="mw-redirect" title="ERβ">ERβ</a>.<sup id="cite_ref-TrostKhera2014_18-2" class="reference"><a href="#cite_note-TrostKhera2014-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Clomifene has antiestrogenic effects in the <a href="/wiki/Uterus" title="Uterus">uterus</a>.<sup id="cite_ref-Goldstein2000_32-0" class="reference"><a href="#cite_note-Goldstein2000-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> There is little clinical research on the influence of clomifene in many target tissues, such as <a href="/wiki/Lipid" title="Lipid">lipids</a>, the <a href="/wiki/Cardiovascular_system" class="mw-redirect" title="Cardiovascular system">cardiovascular system</a>, and the <a href="/wiki/Breast" title="Breast">breasts</a>.<sup id="cite_ref-Goldstein2000_32-1" class="reference"><a href="#cite_note-Goldstein2000-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Haskell2003_33-0" class="reference"><a href="#cite_note-Haskell2003-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> Positive effects of clomifene on <a href="/wiki/Bone" title="Bone">bone</a> have been observed.<sup id="cite_ref-TrostKhera2014_18-3" class="reference"><a href="#cite_note-TrostKhera2014-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Goldstein2000_32-2" class="reference"><a href="#cite_note-Goldstein2000-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Haskell2003_33-1" class="reference"><a href="#cite_note-Haskell2003-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> Clomifene has been found to decrease <a href="/wiki/Insulin-like_growth_factor_1" title="Insulin-like growth factor 1">insulin-like growth factor 1</a> (IGF-1) levels in women.<sup id="cite_ref-pmid27704479_34-0" class="reference"><a href="#cite_note-pmid27704479-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p><p>Clomifene is a long-acting ER <a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">ligand</a>, with a <a href="/wiki/Nuclear_retention" class="mw-redirect" title="Nuclear retention">nuclear retention</a> of greater than 48 hours.<sup id="cite_ref-RunnebaumRabe2013_35-0" class="reference"><a href="#cite_note-RunnebaumRabe2013-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> Clomifene is a <a href="/wiki/Prodrug" title="Prodrug">prodrug</a> being activated via similar <a href="/wiki/Metabolic_pathway" title="Metabolic pathway">metabolic pathways</a> as the related triphenylethylene SERMs tamoxifen and <a href="/wiki/Toremifene" title="Toremifene">toremifene</a>.<sup id="cite_ref-RocheZito2019_36-0" class="reference"><a href="#cite_note-RocheZito2019-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid23406671_37-0" class="reference"><a href="#cite_note-pmid23406671-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Affinity_(pharmacology)" class="mw-redirect" title="Affinity (pharmacology)">affinity</a> of clomifene for the ER relative to <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a> ranges from 0.1 to 12% in different studies, which is similar to the range for tamoxifen (0.06–16%).<sup id="cite_ref-WittliffKerr2005_38-0" class="reference"><a href="#cite_note-WittliffKerr2005-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid10746941_39-0" class="reference"><a href="#cite_note-pmid10746941-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid11258977_40-0" class="reference"><a href="#cite_note-pmid11258977-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> 4-Hydroxyclomifene, a major active metabolite of clomifene, and <a href="/wiki/Afimoxifene" title="Afimoxifene">afimoxifene</a> (4-hydroxytamoxifen), a major active metabolite of tamoxifen, show 89–251% and 41–246% of the affinity of estradiol for the ER in human <a href="/wiki/MCF-7" title="MCF-7">MCF-7</a> <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a> <a href="/wiki/Cell_(biology)" title="Cell (biology)">cells</a>, respectively.<sup id="cite_ref-pmid9586957_41-0" class="reference"><a href="#cite_note-pmid9586957-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid3778464_42-0" class="reference"><a href="#cite_note-pmid3778464-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> The ER affinities of the <a href="/wiki/Isomer" title="Isomer">isomers</a> of 4-hydroxyclomifene were 285% for (<i>E</i>)-4-hydroxyclomifene and 16% for (<i>Z</i>)-4-hydroxyclomifene relative to estradiol.<sup id="cite_ref-pmid9586957_41-1" class="reference"><a href="#cite_note-pmid9586957-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> 4-Hydroxy-<i>N</i>-desmethylclomifene has similar affinity to 4-hydroxyclomifene for the ER.<sup id="cite_ref-pmid23406671_37-1" class="reference"><a href="#cite_note-pmid23406671-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> In one study, the affinities of clomifene and its metabolites for the <a href="/wiki/ER%CE%B1" class="mw-redirect" title="ERα">ERα</a> were ~100 nM for clomifene, ~2.4 nM for 4-hydroxyclomifene, ~125 nM for <i>N</i>-desmethylclomifene, and ~1.4 nM for 4-hydroxy-<i>N</i>-desmethylclomifene.<sup id="cite_ref-pmid23406671_37-2" class="reference"><a href="#cite_note-pmid23406671-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> </p><p>Even though clomifene has some <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogenic</a> effect, the <a href="/wiki/Antiestrogen" title="Antiestrogen">antiestrogenic</a> property is believed to be the primary source for <a href="/wiki/Ovulation_induction" title="Ovulation induction">stimulating ovulation</a>.<sup id="cite_ref-AHFS2016_5-5" class="reference"><a href="#cite_note-AHFS2016-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Clomifene appears to act mostly in the <a href="/wiki/Hypothalamus" title="Hypothalamus">hypothalamus</a> where it depletes hypothalamic ERs and blocks the <a href="/wiki/Negative_feedback" title="Negative feedback">negative feedback</a> effect of circulating <a href="/wiki/Endogenous" class="mw-redirect" title="Endogenous">endogenous</a> <a href="/wiki/Estradiol" title="Estradiol">estradiol</a>, which in turn results in an increase in <a href="/wiki/Hypothalamus" title="Hypothalamus">hypothalamic</a> <a href="/wiki/Gonadotropin-releasing_hormone" title="Gonadotropin-releasing hormone">gonadotropin-releasing hormone</a> (GnRH) pulse frequency and circulating concentrations of <a href="/wiki/Follicle-stimulating_hormone" title="Follicle-stimulating hormone">follicle-stimulating hormone</a> (FSH) and <a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone">luteinizing hormone</a> (LH).<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (May 2024)">medical citation needed</span></a></i>]</sup> </p><p>In normal physiologic female hormonal cycling, at seven days past <a href="/wiki/Ovulation" title="Ovulation">ovulation</a>, high levels of estrogen and <a href="/wiki/Progesterone" title="Progesterone">progesterone</a> produced from the corpus luteum inhibit GnRH, FSH, and LH at the hypothalamus and anterior pituitary.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (May 2024)">medical citation needed</span></a></i>]</sup> If fertilization does not occur in the post-ovulation period the <a href="/wiki/Corpus_luteum" title="Corpus luteum">corpus luteum</a> disintegrates due to a lack of <a href="/wiki/Human_chorionic_gonadotropin" title="Human chorionic gonadotropin">human chorionic gonadotropin</a> (hCG).<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (May 2024)">medical citation needed</span></a></i>]</sup> This would normally be produced by the embryo in the effort of maintaining progesterone and estrogen levels during pregnancy.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (May 2024)">medical citation needed</span></a></i>]</sup> </p><p>Therapeutically, clomifene is given early in the <a href="/wiki/Menstrual_cycle" title="Menstrual cycle">menstrual cycle</a> to produce follicles.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (May 2024)">medical citation needed</span></a></i>]</sup> Follicles, in turn, produce the estrogen, which circulates in serum.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (May 2024)">medical citation needed</span></a></i>]</sup> In the presence of clomifene, the body perceives a low level of estrogen, similar to day 22 in the previous cycle.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (May 2024)">medical citation needed</span></a></i>]</sup> Since estrogen can no longer effectively exert negative feedback on the hypothalamus, GnRH secretion becomes more rapidly pulsatile, which results in increased pituitary gonadotropin release.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (May 2024)">medical citation needed</span></a></i>]</sup> (More rapid, lower amplitude pulses of GnRH lead to increased LH and FSH secretion, while more irregular, larger amplitude pulses of GnRH leads to a decrease in the ratio of LH to FSH.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (May 2024)">medical citation needed</span></a></i>]</sup>) Increased FSH levels cause the growth of more ovarian follicles, and subsequently rupture of follicles resulting in ovulation. Ovulation occurs most often 6 to 7 days after a course of clomifene.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (May 2024)">medical citation needed</span></a></i>]</sup> </p><p>In normal men, 50 mg/day clomifene for 8 months has been found to increase <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> levels by around 870 ng/dL in younger men and by around 490 ng/dL in elderly men.<sup id="cite_ref-TrostKhera2014_18-4" class="reference"><a href="#cite_note-TrostKhera2014-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Estradiol" title="Estradiol">Estradiol</a> levels increased by 62 pg/mL in younger men and by 40 pg/mL in elderly men.<sup id="cite_ref-TrostKhera2014_18-5" class="reference"><a href="#cite_note-TrostKhera2014-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> These findings suggest that the <a href="/wiki/Progonadotropic" class="mw-redirect" title="Progonadotropic">progonadotropic</a> effects of clomifene are stronger in younger men than in older men.<sup id="cite_ref-TrostKhera2014_18-6" class="reference"><a href="#cite_note-TrostKhera2014-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> In men with <a href="/wiki/Hypogonadism" title="Hypogonadism">hypogonadism</a>, clomifene has been found to increase testosterone levels by 293 to 362 ng/dL and estradiol levels by 5.5 to 13 pg/mL.<sup id="cite_ref-TrostKhera2014_18-7" class="reference"><a href="#cite_note-TrostKhera2014-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> In a large clinical study of men with low testosterone levels (<400 ng/dL), 25 mg/day clomifene increased testosterone levels from 309 ng/dL to 642 ng/dL after 3 months of therapy.<sup id="cite_ref-pmid27601965_43-0" class="reference"><a href="#cite_note-pmid27601965-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> No significant changes in <a href="/wiki/HDL_cholesterol" class="mw-redirect" title="HDL cholesterol">HDL cholesterol</a>, <a href="/wiki/Triglyceride" title="Triglyceride">triglycerides</a>, fasting <a href="/wiki/Glucose" title="Glucose">glucose</a>, or <a href="/wiki/Prolactin" title="Prolactin">prolactin</a> levels were observed, although <a href="/wiki/Total_cholesterol" class="mw-redirect" title="Total cholesterol">total cholesterol</a> levels decreased significantly.<sup id="cite_ref-TrostKhera2014_18-8" class="reference"><a href="#cite_note-TrostKhera2014-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid27601965_43-1" class="reference"><a href="#cite_note-pmid27601965-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable mw-collapsible mw-collapsed" style="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 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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:Tissue-specific_estrogenic_and_antiestrogenic_activity_of_SERMs" title="Template:Tissue-specific estrogenic and antiestrogenic activity of SERMs"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Tissue-specific_estrogenic_and_antiestrogenic_activity_of_SERMs" title="Template talk:Tissue-specific estrogenic and antiestrogenic activity of SERMs"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Tissue-specific_estrogenic_and_antiestrogenic_activity_of_SERMs" title="Special:EditPage/Template:Tissue-specific estrogenic and antiestrogenic activity of SERMs"><abbr title="Edit this template">e</abbr></a></li></ul></div> Tissue-specific estrogenic and antiestrogenic activity of <abbr title="selective estrogen receptor modulators">SERMs</abbr> </caption> <tbody><tr> <th rowspan="2">Medication</th> <th rowspan="2"><a href="/wiki/Breast" title="Breast">Breast</a></th> <th rowspan="2"><a href="/wiki/Bone" title="Bone">Bone</a></th> <th colspan="4"><a href="/wiki/Liver" title="Liver">Liver</a></th> <th rowspan="2"><a href="/wiki/Uterus" title="Uterus">Uterus</a></th> <th rowspan="2"><a href="/wiki/Vagina" title="Vagina">Vagina</a></th> <th colspan="3"><a href="/wiki/Brain" title="Brain">Brain</a> </th></tr> <tr> <th><a href="/wiki/Lipids" class="mw-redirect" title="Lipids">Lipids</a></th> <th><a href="/wiki/Coagulation" title="Coagulation">Coagulation</a></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></th> <th><a href="/wiki/Insulin-like_growth_factor_1" title="Insulin-like growth factor 1"><abbr title="Insulin-like growth factor 1">IGF-1</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 Insulin-like growth factor 1</span></th> <th><a href="/wiki/Hot_flash" title="Hot flash">Hot flashes</a></th> <th><a href="/wiki/Gonadotropin" title="Gonadotropin">Gonadotropins</a> </th></tr> <tr> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a></td> <td><style data-mw-deduplicate="TemplateStyles:r1239334494">@media screen{html.skin-theme-clientpref-night .mw-parser-output div:not(.notheme)>.tmp-color,html.skin-theme-clientpref-night .mw-parser-output p>.tmp-color,html.skin-theme-clientpref-night .mw-parser-output table:not(.notheme) .tmp-color{color:inherit!important}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output div:not(.notheme)>.tmp-color,html.skin-theme-clientpref-os .mw-parser-output p>.tmp-color,html.skin-theme-clientpref-os .mw-parser-output table:not(.notheme) .tmp-color{color:inherit!important}}</style><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span> </td></tr> <tr> <td>"Ideal SERM"</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Limegreen">±</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Limegreen">±</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Limegreen">±</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Limegreen">±</span> </td></tr> <tr> <td><a href="/wiki/Bazedoxifene" title="Bazedoxifene">Bazedoxifene</a></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td>?</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Limegreen">±</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td>? </td></tr> <tr> <td>Clomifene</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td>?</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td>?</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Limegreen">±</span> </td></tr> <tr> <td><a href="/wiki/Lasofoxifene" title="Lasofoxifene">Lasofoxifene</a></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td>?</td> <td>?</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Limegreen">±</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Limegreen">±</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td>? </td></tr> <tr> <td><a href="/wiki/Ospemifene" title="Ospemifene">Ospemifene</a></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Limegreen">±</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Limegreen">±</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Limegreen">±</span> </td></tr> <tr> <td><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Limegreen">±</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Limegreen">±</span> </td></tr> <tr> <td><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Limegreen">±</span> </td></tr> <tr> <td><a href="/wiki/Toremifene" title="Toremifene">Toremifene</a></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Limegreen">±</span> </td></tr> <tr class="sortbottom"> <td colspan="15" style="width: 1px; background-color:#eaecf0; text-align: center;"><b>Effect:</b> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span> = <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogenic</a> / <a href="/wiki/Agonist" title="Agonist">agonistic</a>. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Limegreen">±</span> = Mixed or neutral. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span> = <a href="/wiki/Antiestrogen" title="Antiestrogen">Antiestrogenic</a> / <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonistic</a>. <b>Note:</b> SERMs generally increase gonadotropin levels in hypogonadal and eugonadal men as well as premenopausal women (antiestrogenic) but decrease gonadotropin levels in postmenopausal women (estrogenic). <b>Sources:</b> See template. </td></tr></tbody></table> <div class="mw-heading mw-heading4"><h4 id="Other_activities">Other activities</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Clomifene&action=edit&section=12" title="Edit section: Other activities"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Clomifene is an <a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibitor</a> of the conversion of <a href="/wiki/Desmosterol" title="Desmosterol">desmosterol</a> into <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a> by the <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> <a href="/wiki/24-dehydrocholesterol_reductase" class="mw-redirect" title="24-dehydrocholesterol reductase">24-dehydrocholesterol reductase</a>.<sup id="cite_ref-Zhang2018_44-0" class="reference"><a href="#cite_note-Zhang2018-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MaximovMcDaniel2013a_45-0" class="reference"><a href="#cite_note-MaximovMcDaniel2013a-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> Concerns about possible induction of <a href="/wiki/Desmosterolosis" title="Desmosterolosis">desmosterolosis</a> and associated symptoms such as <a href="/wiki/Cataract" title="Cataract">cataracts</a> and <a href="/wiki/Ichthyosis" title="Ichthyosis">ichthyosis</a> with extended exposure precluded the use of clomifene in the treatment of breast cancer.<sup id="cite_ref-Zhang2018_44-1" class="reference"><a href="#cite_note-Zhang2018-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MaximovMcDaniel2013a_45-1" class="reference"><a href="#cite_note-MaximovMcDaniel2013a-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> Continuous use of clomifene has been found to increase desmosterol levels by 10% and continuous high doses of clomifene (200 mg/day) have been reported to produce <a href="/wiki/Visual_disturbance" class="mw-redirect" title="Visual disturbance">visual disturbances</a>.<sup id="cite_ref-Jucker2013_46-0" class="reference"><a href="#cite_note-Jucker2013-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Pharmacokinetics">Pharmacokinetics</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Clomifene&action=edit&section=13" title="Edit section: Pharmacokinetics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Clomifene produces <i>N</i>-desmethylclomifene, <a href="/wiki/Clomifenoxide" title="Clomifenoxide">clomifenoxide</a> (clomifene <i>N</i>-oxide), 4-hydroxyclomifene, and 4-hydroxy-<i>N</i>-desmethylclomifene as <a href="/wiki/Metabolite" title="Metabolite">metabolites</a>.<sup id="cite_ref-pmid29516347_2-4" class="reference"><a href="#cite_note-pmid29516347-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-AcademicPress1998_48-0" class="reference"><a href="#cite_note-AcademicPress1998-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> Clomifene is a <a href="/wiki/Prodrug" title="Prodrug">prodrug</a> most importantly of 4-hydroxyclomifene and 4-hydroxy-<i>N</i>-desmethylclomifene, which are the most active of its metabolites.<sup id="cite_ref-RocheZito2019_36-1" class="reference"><a href="#cite_note-RocheZito2019-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid23406671_37-3" class="reference"><a href="#cite_note-pmid23406671-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> In one study, the <a href="/wiki/Peak_levels" class="mw-redirect" title="Peak levels">peak levels</a> after a single 50 mg dose of clomifene were 20.37 nmol/L for clomifene, 0.95 nmol/L for 4-hydroxyclomifene, and 1.15 nmol/L for 4-hydroxy-<i>N</i>-desmethylclomifene.<sup id="cite_ref-pmid29516347_2-5" class="reference"><a href="#cite_note-pmid29516347-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>Clomifene has an <a href="/wiki/Onset_of_action" title="Onset of action">onset of action</a> of 5 to 10 days following course of treatment and an <a href="/wiki/Elimination_half-life" class="mw-redirect" title="Elimination half-life">elimination half-life</a> about 4 - 7days.<sup id="cite_ref-pmid29516347_2-6" class="reference"><a href="#cite_note-pmid29516347-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-singledosekinetics_4-2" class="reference"><a href="#cite_note-singledosekinetics-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> In one study, after a single 50 mg dose of clomifene, the half-life of clomifene was 128 hours (5.3 days), of 4-hydroxyclomifene was 13 hours, and of 4-hydroxy-<i>N</i>-desmethylclomifene was 15 hours.<sup id="cite_ref-pmid29516347_2-7" class="reference"><a href="#cite_note-pmid29516347-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Individuals with the CYP2D6*10 <a href="/wiki/Allele" title="Allele">allele</a> showed longer half-lives for 4-hydroxyclomifene and 4-hydroxy-<i>N</i>-desmethylclomifene.<sup id="cite_ref-pmid29516347_2-8" class="reference"><a href="#cite_note-pmid29516347-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Primarily due to differences in CYP2D6 genetics, steady state concentrations and individual response to clomifene are highly variable.<sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> </p><p>Most clomifene metabolism occurs in the <a href="/wiki/Liver" title="Liver">liver</a>, where it undergoes <a href="/wiki/Enterohepatic_recirculation" class="mw-redirect" title="Enterohepatic recirculation">enterohepatic recirculation</a>. Clomifene and its metabolites are <a href="/wiki/Excretion" title="Excretion">excreted</a> primarily through <a href="/wiki/Feces" title="Feces">feces</a> (42%), and excretion can occur up to 6 weeks after discontinuation.<sup id="cite_ref-:1_31-1" class="reference"><a href="#cite_note-:1-31"><span class="cite-bracket">[</span>31<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=Clomifene&action=edit&section=14" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Clomifene is a <a href="/wiki/Triphenylethylene" title="Triphenylethylene">triphenylethylene</a> derivative. It is a mixture of two <a href="/wiki/Geometric_isomerism" class="mw-redirect" title="Geometric isomerism">geometric isomers</a>, the cis <a href="/wiki/Enclomifene" title="Enclomifene">enclomifene</a> (<i>(E)</i>-clomifene) form and trans <a href="/wiki/Zuclomifene" title="Zuclomifene">zuclomifene</a> (<i>(Z)</i>-clomifene) form. These two isomers contribute to the mixed estrogenic and antiestrogenic properties of clomifene.<sup id="cite_ref-Hist_10-1" class="reference"><a href="#cite_note-Hist-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> The typical ratio of these isomers after synthesis is 38% zuclomiphene and 62% enclomiphene.<sup id="cite_ref-singledosekinetics_4-3" class="reference"><a href="#cite_note-singledosekinetics-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> The United States Pharmacopeia specifies that clomifene preparations must contain between 30% and 50% zuclomiphene.<sup id="cite_ref-singledosekinetics_4-4" class="reference"><a href="#cite_note-singledosekinetics-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <table> <tbody><tr> <td><figure typeof="mw:File/Frame"><a href="/wiki/File:Enclomifene.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/f/f6/Enclomifene.png" decoding="async" width="202" height="118" class="mw-file-element" data-file-width="202" data-file-height="118" /></a><figcaption><a href="/wiki/Enclomifene" title="Enclomifene">Enclomifene</a></figcaption></figure> </td> <td><figure typeof="mw:File/Frame"><a href="/wiki/File:Zuclomifene.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/6/61/Zuclomifene.png" decoding="async" width="201" height="117" class="mw-file-element" data-file-width="201" data-file-height="117" /></a><figcaption><a href="/wiki/Zuclomifene" title="Zuclomifene">Zuclomifene</a></figcaption></figure> </td></tr></tbody></table> <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=Clomifene&action=edit&section=15" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A team at <a href="/wiki/William_S._Merrell_Chemical_Company" class="mw-redirect" title="William S. Merrell Chemical Company">William S. Merrell Chemical Company</a> led by Frank Palopoli synthesized clomifene in 1956; after its biological activity was confirmed a patent was filed and issued in November 1959.<sup id="cite_ref-Hist_10-2" class="reference"><a href="#cite_note-Hist-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> Scientists at Merrell had previously synthesized <a href="/wiki/Chlorotrianisene" title="Chlorotrianisene">chlorotrianisene</a> and <a href="/wiki/Ethamoxytriphetol" title="Ethamoxytriphetol">ethamoxytriphetol</a>.<sup id="cite_ref-Hist_10-3" class="reference"><a href="#cite_note-Hist-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Clomifene was studied in the treatment of <a href="/wiki/Advanced_breast_cancer" class="mw-redirect" title="Advanced breast cancer">advanced breast cancer</a> during the period of 1964 to 1974 and was found to be effective but was abandoned due to concerns about <a href="/wiki/Desmosterolosis" title="Desmosterolosis">desmosterolosis</a> with extended use.<sup id="cite_ref-Zhang2018_44-2" class="reference"><a href="#cite_note-Zhang2018-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid12796359_51-0" class="reference"><a href="#cite_note-pmid12796359-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HowellJordan2013B_52-0" class="reference"><a href="#cite_note-HowellJordan2013B-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> Short-term use (e.g. days to months) did not raise the same concerns and clomifene continued to be studied for other indications.<sup id="cite_ref-MaximovMcDaniel2013a_45-2" class="reference"><a href="#cite_note-MaximovMcDaniel2013a-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Jucker2013_46-1" class="reference"><a href="#cite_note-Jucker2013-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable" style="font-size:small; margin: 1em auto;"> <caption class="nowrap"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Comparison_of_early_clinical_experience_with_antiestrogens_for_advanced_breast_cancer" title="Template:Comparison of early clinical experience with antiestrogens for advanced breast cancer"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Comparison_of_early_clinical_experience_with_antiestrogens_for_advanced_breast_cancer" title="Template talk:Comparison of early clinical experience with antiestrogens for advanced breast cancer"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Comparison_of_early_clinical_experience_with_antiestrogens_for_advanced_breast_cancer" title="Special:EditPage/Template:Comparison of early clinical experience with antiestrogens for advanced breast cancer"><abbr title="Edit this template">e</abbr></a></li></ul></div> <span style="font-size:105%;">Comparison of early clinical experience with antiestrogens for advanced breast cancer</span> </caption> <tbody><tr> <th>Antiestrogen </th> <th>Dosage </th> <th>Year(s) </th> <th>Response rate </th> <th>Adverse effects </th></tr> <tr> <td><a href="/wiki/Ethamoxytriphetol" title="Ethamoxytriphetol">Ethamoxytriphetol</a> </td> <td>500–4,500 mg/day </td> <td>1960 </td> <td>25% </td> <td><a href="/wiki/Acute_psychotic_episode" class="mw-redirect" title="Acute psychotic episode">Acute psychotic episodes</a> </td></tr> <tr> <td>Clomifene </td> <td>100–300 mg/day </td> <td>1964–1974 </td> <td>34% </td> <td>Risks of <a href="/wiki/Cataract" title="Cataract">cataracts</a> </td></tr> <tr> <td><a href="/wiki/Nafoxidine" title="Nafoxidine">Nafoxidine</a> </td> <td>180–240 mg/day </td> <td>1976 </td> <td>31% </td> <td><a href="/wiki/Cataract" title="Cataract">Cataracts</a>, <a href="/wiki/Ichthyosis" title="Ichthyosis">ichthyosis</a>, <a href="/wiki/Photophobia" title="Photophobia">photophobia</a> </td></tr> <tr> <td><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a> </td> <td>20–40 mg/day </td> <td>1971–1973 </td> <td>31% </td> <td>Transient <a href="/wiki/Thrombocytopenia" title="Thrombocytopenia">thrombocytopenia</a><sup>a</sup> </td></tr> <tr> <td colspan="5" style="width: 1px; background-color:#eaecf0; text-align: center;"><b>Footnotes:</b> <sup>a</sup> = "The particular advantage of this drug is the low incidence of troublesome side effects (25)." "Side effects were usually trivial (26)." <b>Sources:</b> <sup id="cite_ref-pmid12796359_51-1" class="reference"><a href="#cite_note-pmid12796359-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HowellJordan2013_53-0" class="reference"><a href="#cite_note-HowellJordan2013-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> </td></tr></tbody></table> <p>Clinical studies were conducted under an <a href="/wiki/Investigational_New_Drug" title="Investigational New Drug">Investigational New Drug</a> Application; clomifene was third drug for which an IND had been filed under the 1962 <a href="/wiki/Kefauver_Harris_Amendment" class="mw-redirect" title="Kefauver Harris Amendment">Kefauver Harris Amendment</a> to the <a href="/wiki/Federal_Food,_Drug,_and_Cosmetic_Act" class="mw-redirect" title="Federal Food, Drug, and Cosmetic Act">Federal Food, Drug, and Cosmetic Act</a> that had been passed in response to the <a href="/wiki/Thalidomide" title="Thalidomide">thalidomide</a> tragedy.<sup id="cite_ref-Hist_10-4" class="reference"><a href="#cite_note-Hist-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> It was approved for marketing in 1967 under the brand name Clomid.<sup id="cite_ref-Hist_10-5" class="reference"><a href="#cite_note-Hist-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-54" class="reference"><a href="#cite_note-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> It was first used to treat cases of <a href="/wiki/Oligomenorrhea" title="Oligomenorrhea">oligomenorrhea</a> but was expanded to include treatment of <a href="/wiki/Anovulation" title="Anovulation">anovulation</a> when women undergoing treatment had higher than expected rates of pregnancy.<sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> </p><p>The drug is widely considered to have been a revolution in the treatment of female infertility, the beginning of the modern era of <a href="/wiki/Assisted_reproductive_technology" title="Assisted reproductive technology">assisted reproductive technology</a>, and the beginning of what in the words of <a href="/wiki/Eli_Y._Adashi" class="mw-redirect" title="Eli Y. Adashi">Eli Y. Adashi</a>, was "the onset of the US multiple births epidemic".<sup id="cite_ref-Hist_10-6" class="reference"><a href="#cite_note-Hist-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-56" class="reference"><a href="#cite_note-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> </p><p>The company was acquired by <a href="/wiki/Dow_Chemical" class="mw-redirect" title="Dow Chemical">Dow Chemical</a> in 1980,<sup id="cite_ref-Los_Angeles_Times_57-0" class="reference"><a href="#cite_note-Los_Angeles_Times-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-58" class="reference"><a href="#cite_note-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> and in 1989 Dow Chemical acquired 67 percent interest of Marion Laboratories, which was renamed Marion Merrell Dow.<sup id="cite_ref-Los_Angeles_Times_57-1" class="reference"><a href="#cite_note-Los_Angeles_Times-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> In 1995 Hoechst AG acquired the pharmaceutical business of Marion Merrell Dow.<sup id="cite_ref-59" class="reference"><a href="#cite_note-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> Hoechst in turn became part of <a href="/wiki/Aventis" class="mw-redirect" title="Aventis">Aventis</a> in 1999,<sup id="cite_ref-Bris_60-0" class="reference"><a href="#cite_note-Bris-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 9–11">: 9–11 </span></sup> and subsequently a part of <a href="/wiki/Sanofi" title="Sanofi">Sanofi</a>.<sup id="cite_ref-61" class="reference"><a href="#cite_note-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> It became the most widely prescribed drug for <a href="/wiki/Ovulation_induction" title="Ovulation induction">ovulation induction</a> to reverse <a href="/wiki/Anovulation" title="Anovulation">anovulation</a> or <a href="/wiki/Oligoovulation" class="mw-redirect" title="Oligoovulation">oligoovulation</a>.<sup id="cite_ref-StraussBarbieri2013_62-0" class="reference"><a href="#cite_note-StraussBarbieri2013-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Clomifene&action=edit&section=16" title="Edit section: Society and culture"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Brand_names">Brand names</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Clomifene&action=edit&section=17" title="Edit section: Brand names"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Clomifene is marketed under many brand names worldwide, including Beclom, Bemot, Biogen, Blesifen, Chloramiphene, Clofert, Clomene, ClomHEXAL, Clomi, Clomid, Clomidac, Clomifen, Clomifencitrat, Clomifene, Clomifène, Clomifene citrate, Clomifeni citras, Clomifeno, Clomifert, Clomihexal, Clomiphen, Clomiphene, Clomiphene Citrate, Cloninn, Clostil, Clostilbegyt, Clovertil, Clovul, Dipthen, Dufine, Duinum, Fensipros, Fertab, Fertec, Fertex, Ferticlo, Fertil, Fertilan, Fertilphen, Fertin, Fertomid, Ferton, Fertotab, Fertyl, Fetrop, Folistim, Genoclom, Genozym, Hete, I-Clom, Ikaclomin, Klofit, Klomen, Klomifen, Lomifen, MER 41, Milophene, Ofertil, Omifin, Ova-mit, Ovamit, Ovinum, Ovipreg, Ovofar, Ovuclon, Ovulet, Pergotime, Pinfetil, Profertil, Prolifen, Provula, Reomen, Serofene, Serophene, Serpafar, Serpafar, Surole, Tocofeno, and Zimaquin.<sup id="cite_ref-Brands_1-1" class="reference"><a href="#cite_note-Brands-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Regulation">Regulation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Clomifene&action=edit&section=18" title="Edit section: Regulation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Clomifene is included on the <a href="/wiki/World_Anti-Doping_Agency" title="World Anti-Doping Agency">World Anti-Doping Agency</a> list of illegal doping agents in sport.<sup id="cite_ref-63" class="reference"><a href="#cite_note-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup> It is listed because it is an "anti-estrogenic substance".<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. (May 2024)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Clomifene&action=edit&section=19" title="Edit section: Research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Clomifene has been used almost exclusively for ovulation induction in <a href="/wiki/Premenopausal" class="mw-redirect" title="Premenopausal">premenopausal</a> women, and has been studied very limitedly in <a href="/wiki/Postmenopausal" class="mw-redirect" title="Postmenopausal">postmenopausal</a> women.<sup id="cite_ref-Palacios2007_64-0" class="reference"><a href="#cite_note-Palacios2007-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> </p><p>Clomifene was studied for treatment and prevention of <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a>, but issues with toxicity led to abandonment of this indication, as did the discovery of <a href="/wiki/Tamoxifen" title="Tamoxifen">tamoxifen</a>.<sup id="cite_ref-65" class="reference"><a href="#cite_note-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> Like the structurally related drug <a href="/wiki/Triparanol" title="Triparanol">triparanol</a>, clomifene is known to <a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibit</a> the <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> <a href="/wiki/24-dehydrocholesterol_reductase" class="mw-redirect" title="24-dehydrocholesterol reductase">24-dehydrocholesterol reductase</a> and increase circulating <a href="/wiki/Desmosterol" title="Desmosterol">desmosterol</a> levels, making it unfavorable for extended use in breast cancer due to risk of side effects like irreversible <a href="/wiki/Cataracts" class="mw-redirect" title="Cataracts">cataracts</a>.<sup id="cite_ref-Elsevier2013_66-0" class="reference"><a href="#cite_note-Elsevier2013-66"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MaximovMcDaniel2013b_67-0" class="reference"><a href="#cite_note-MaximovMcDaniel2013b-67"><span class="cite-bracket">[</span>67<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=Clomifene&action=edit&section=20" 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-Brands-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Brands_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Brands_1-1"><sup><i><b>b</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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.drugs.com/international/clomifene.html">"International brands of clomifene -"</a>. Drugs.com. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20160920215822/https://www.drugs.com/international/clomifene.html">Archived</a> from the original on 20 September 2016<span class="reference-accessdate">. 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World Scientific. pp. 229–254. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1142%2F9781848169586_0010">10.1142/9781848169586_0010</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-84816-959-3" title="Special:BookSources/978-1-84816-959-3"><bdi>978-1-84816-959-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Adjuvant+Antihormone+Therapy&rft.btitle=Estrogen+Action%2C+Selective+Estrogen+Receptor+Modulators+And+Women%27s+Health%3A+Progress+And+Promise&rft.pages=229-254&rft.pub=World+Scientific&rft.date=2013&rft_id=info%3Adoi%2F10.1142%2F9781848169586_0010&rft.isbn=978-1-84816-959-3&rft.aulast=Howell&rft.aufirst=A&rft.au=Jordan%2C+VC&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DZM26CgAAQBAJ%26pg%3DPA229&rfr_id=info%3Asid%2Fen.wikipedia.org%3AClomifene" class="Z3988"></span></span> </li> <li id="cite_note-HowellJordan2013-53"><span class="mw-cite-backlink"><b><a href="#cite_ref-HowellJordan2013_53-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHowellJordan2013" class="citation book cs1">Howell A, Jordan VC (2013). 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Reuters. 5 May 1995. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20161006125440/http://www.sfgate.com/business/article/Hoechst-AG-to-Buy-Marion-Merrell-Dow-3035234.php">Archived</a> from the original on 6 October 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=San+Francisco+Chronicle&rft.atitle=Hoechst+AG+to+Buy+Marion+Merrell+Dow+%2F+Acquisition+worth+over+%247+billion&rft.date=1995-05-05&rft_id=http%3A%2F%2Fwww.sfgate.com%2Fbusiness%2Farticle%2FHoechst-AG-to-Buy-Marion-Merrell-Dow-3035234.php&rfr_id=info%3Asid%2Fen.wikipedia.org%3AClomifene" class="Z3988"></span></span> </li> <li id="cite_note-Bris-60"><span class="mw-cite-backlink"><b><a href="#cite_ref-Bris_60-0">^</a></b></span> <span class="reference-text">Arturo Bris and Christos Cabolis, <a rel="nofollow" class="external text" href="http://citeseerx.ist.psu.edu/viewdoc/download?doi=10.1.1.365.5937&rep=rep1&type=pdf">Corporate Governance Convergence Through Cross-Border Mergers The Case of Aventis</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20140421081504/http://citeseerx.ist.psu.edu/viewdoc/download?doi=10.1.1.365.5937&rep=rep1&type=pdf">Archived</a> 21 April 2014 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a>, Chapter 4 in <a rel="nofollow" class="external text" href="https://books.google.com/books?id=Cfc22UYifJQC">Corporate Governance and Regulatory Impact on Mergers and Acquisitions: Research and Analysis on Activity Worldwide Since 1990</a>. Eds Greg N. Gregoriou, Luc Renneboog. Academic Press, 26 July 2007</span> </li> <li id="cite_note-61"><span class="mw-cite-backlink"><b><a href="#cite_ref-61">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTimmonsBennhold2004" class="citation news cs1">Timmons H, Bennhold K (27 April 2004). <a rel="nofollow" class="external text" href="https://www.nytimes.com/2004/04/27/business/france-helped-broker-the-aventis-sanofi-deal.html?_r=0">"France Helped Broker the Aventis-Sanofi Deal"</a>. <i>The New York Times</i>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20171105200804/http://www.nytimes.com/2004/04/27/business/france-helped-broker-the-aventis-sanofi-deal.html?_r=0">Archived</a> from the original on 5 November 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+New+York+Times&rft.atitle=France+Helped+Broker+the+Aventis-Sanofi+Deal&rft.date=2004-04-27&rft.aulast=Timmons&rft.aufirst=H&rft.au=Bennhold%2C+K&rft_id=https%3A%2F%2Fwww.nytimes.com%2F2004%2F04%2F27%2Fbusiness%2Ffrance-helped-broker-the-aventis-sanofi-deal.html%3F_r%3D0&rfr_id=info%3Asid%2Fen.wikipedia.org%3AClomifene" class="Z3988"></span></span> </li> <li id="cite_note-StraussBarbieri2013-62"><span class="mw-cite-backlink"><b><a href="#cite_ref-StraussBarbieri2013_62-0">^</a></b></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=PA518"><i>Yen and Jaffe's Reproductive Endocrinology</i></a>. Elsevier Health Sciences. pp. 518–. <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>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20171105200803/https://books.google.com/books?id=KZ95AAAAQBAJ&pg=PA518">Archived</a> from the original on 5 November 2017.</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=518-&rft.pub=Elsevier+Health+Sciences&rft.date=2013-09-13&rft.isbn=978-1-4557-2758-2&rft.aulast=Strauss&rft.aufirst=JF&rft.au=Barbieri%2C+RL&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DKZ95AAAAQBAJ%26pg%3DPA518&rfr_id=info%3Asid%2Fen.wikipedia.org%3AClomifene" class="Z3988"></span></span> </li> <li id="cite_note-63"><span class="mw-cite-backlink"><b><a href="#cite_ref-63">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://wada-main-prod.s3.amazonaws.com/resources/files/wada-2016-prohibited-list-en.pdf">The WADA Prohibited List 2016 (listed as clomiphene)</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20160306124802/https://wada-main-prod.s3.amazonaws.com/resources/files/wada-2016-prohibited-list-en.pdf">Archived</a> 6 March 2016 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a></span> </li> <li id="cite_note-Palacios2007-64"><span class="mw-cite-backlink"><b><a href="#cite_ref-Palacios2007_64-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPalacios2007" class="citation journal cs1">Palacios S (March 2007). "The future of the new selective estrogen receptor modulators". <i>Menopause International</i>. <b>13</b> (1): 27–34. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1258%2F175404507780456791">10.1258/175404507780456791</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/17448265">17448265</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:29053109">29053109</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Menopause+International&rft.atitle=The+future+of+the+new+selective+estrogen+receptor+modulators&rft.volume=13&rft.issue=1&rft.pages=27-34&rft.date=2007-03&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A29053109%23id-name%3DS2CID&rft_id=info%3Apmid%2F17448265&rft_id=info%3Adoi%2F10.1258%2F175404507780456791&rft.aulast=Palacios&rft.aufirst=S&rfr_id=info%3Asid%2Fen.wikipedia.org%3AClomifene" class="Z3988"></span></span> </li> <li id="cite_note-65"><span class="mw-cite-backlink"><b><a href="#cite_ref-65">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMaximovLeeJordan2013" class="citation journal cs1">Maximov PY, Lee TM, Jordan VC (May 2013). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3624793">"The discovery and development of selective estrogen receptor modulators (SERMs) for clinical practice"</a>. <i>Current Clinical Pharmacology</i>. <b>8</b> (2): 135–55. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.2174%2F1574884711308020006">10.2174/1574884711308020006</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/PMC3624793">3624793</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/23062036">23062036</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Current+Clinical+Pharmacology&rft.atitle=The+discovery+and+development+of+selective+estrogen+receptor+modulators+%28SERMs%29+for+clinical+practice&rft.volume=8&rft.issue=2&rft.pages=135-55&rft.date=2013-05&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3624793%23id-name%3DPMC&rft_id=info%3Apmid%2F23062036&rft_id=info%3Adoi%2F10.2174%2F1574884711308020006&rft.aulast=Maximov&rft.aufirst=PY&rft.au=Lee%2C+TM&rft.au=Jordan%2C+VC&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3624793&rfr_id=info%3Asid%2Fen.wikipedia.org%3AClomifene" class="Z3988"></span></span> </li> <li id="cite_note-Elsevier2013-66"><span class="mw-cite-backlink"><b><a href="#cite_ref-Elsevier2013_66-0">^</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=vBvzF6HQ4-QC&pg=PA13"><i>Hormones and Breast Cancer</i></a>. Elsevier. 25 June 2013. pp. 13–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-12-416676-9" title="Special:BookSources/978-0-12-416676-9"><bdi>978-0-12-416676-9</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20171105200803/https://books.google.com/books?id=vBvzF6HQ4-QC&pg=PA13">Archived</a> from the original on 5 November 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Hormones+and+Breast+Cancer&rft.pages=13-&rft.pub=Elsevier&rft.date=2013-06-25&rft.isbn=978-0-12-416676-9&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DvBvzF6HQ4-QC%26pg%3DPA13&rfr_id=info%3Asid%2Fen.wikipedia.org%3AClomifene" class="Z3988"></span></span> </li> <li id="cite_note-MaximovMcDaniel2013b-67"><span class="mw-cite-backlink"><b><a href="#cite_ref-MaximovMcDaniel2013b_67-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMaximovMcDanielJordan2013" class="citation book cs1">Maximov PY, McDaniel RE, Jordan VC (2013). "Tamoxifen Goes Forward Alone". <i>Tamoxifen</i>. Milestones in Drug Therapy. Springer. pp. 31–46. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-3-0348-0664-0_2">10.1007/978-3-0348-0664-0_2</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-0348-0663-3" title="Special:BookSources/978-3-0348-0663-3"><bdi>978-3-0348-0663-3</bdi></a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/2296-6064">2296-6064</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Tamoxifen+Goes+Forward+Alone&rft.btitle=Tamoxifen&rft.series=Milestones+in+Drug+Therapy&rft.pages=31-46&rft.pub=Springer&rft.date=2013&rft.issn=2296-6064&rft_id=info%3Adoi%2F10.1007%2F978-3-0348-0664-0_2&rft.isbn=978-3-0348-0663-3&rft.aulast=Maximov&rft.aufirst=PY&rft.au=McDaniel%2C+RE&rft.au=Jordan%2C+VC&rfr_id=info%3Asid%2Fen.wikipedia.org%3AClomifene" class="Z3988"></span></span> </li> </ol></div></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1236075235">.mw-parser-output .navbox{box-sizing:border-box;border:1px solid #a2a9b1;width:100%;clear:both;font-size:88%;text-align:center;padding:1px;margin:1em auto 0}.mw-parser-output .navbox .navbox{margin-top:0}.mw-parser-output .navbox+.navbox,.mw-parser-output .navbox+.navbox-styles+.navbox{margin-top:-1px}.mw-parser-output .navbox-inner,.mw-parser-output .navbox-subgroup{width:100%}.mw-parser-output .navbox-group,.mw-parser-output .navbox-title,.mw-parser-output .navbox-abovebelow{padding:0.25em 1em;line-height:1.5em;text-align:center}.mw-parser-output .navbox-group{white-space:nowrap;text-align:right}.mw-parser-output .navbox,.mw-parser-output .navbox-subgroup{background-color:#fdfdfd}.mw-parser-output .navbox-list{line-height:1.5em;border-color:#fdfdfd}.mw-parser-output .navbox-list-with-group{text-align:left;border-left-width:2px;border-left-style:solid}.mw-parser-output tr+tr>.navbox-abovebelow,.mw-parser-output tr+tr>.navbox-group,.mw-parser-output tr+tr>.navbox-image,.mw-parser-output tr+tr>.navbox-list{border-top:2px solid #fdfdfd}.mw-parser-output .navbox-title{background-color:#ccf}.mw-parser-output .navbox-abovebelow,.mw-parser-output .navbox-group,.mw-parser-output .navbox-subgroup .navbox-title{background-color:#ddf}.mw-parser-output .navbox-subgroup .navbox-group,.mw-parser-output .navbox-subgroup .navbox-abovebelow{background-color:#e6e6ff}.mw-parser-output .navbox-even{background-color:#f7f7f7}.mw-parser-output .navbox-odd{background-color:transparent}.mw-parser-output .navbox .hlist td dl,.mw-parser-output .navbox .hlist td ol,.mw-parser-output .navbox .hlist td ul,.mw-parser-output .navbox td.hlist dl,.mw-parser-output .navbox td.hlist ol,.mw-parser-output .navbox td.hlist ul{padding:0.125em 0}.mw-parser-output .navbox .navbar{display:block;font-size:100%}.mw-parser-output .navbox-title .navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Estrogens_and_antiestrogens" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Estrogens_and_antiestrogens" title="Template:Estrogens and antiestrogens"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Estrogens_and_antiestrogens" title="Template talk:Estrogens and antiestrogens"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Estrogens_and_antiestrogens" title="Special:EditPage/Template:Estrogens and antiestrogens"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Estrogens_and_antiestrogens" style="font-size:114%;margin:0 4em"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogens</a> and <a href="/wiki/Antiestrogen" title="Antiestrogen">antiestrogens</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogens</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0;background:#DDDDFF;"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor</span> 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/Alfatradiol" title="Alfatradiol">Alfatradiol</a></li> <li>Certain <a href="/wiki/Androgen" title="Androgen">androgens</a>/<a href="/wiki/Anabolic_steroid" title="Anabolic steroid">anabolic steroids</a> (e.g., <a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">testosterone</a>, <a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">testosterone esters</a>, <a href="/wiki/Methyltestosterone" title="Methyltestosterone">methyltestosterone</a>, <a href="/wiki/Metandienone" title="Metandienone">metandienone</a>, <a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">nandrolone esters</a>) (via estrogenic metabolites)</li> <li>Certain <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestins</a> (e.g., <a href="/wiki/Norethisterone" title="Norethisterone">norethisterone</a>, <a href="/wiki/Noretynodrel" title="Noretynodrel">noretynodrel</a>, <a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">etynodiol diacetate</a>, <a href="/wiki/Tibolone" title="Tibolone">tibolone</a>)</li> <li><a href="/wiki/Clomestrone" title="Clomestrone">Clomestrone</a></li> <li><a href="/wiki/Cloxestradiol_acetate" title="Cloxestradiol acetate">Cloxestradiol acetate</a></li> <li><a href="/wiki/Conjugated_estriol" title="Conjugated estriol">Conjugated estriol</a></li> <li><a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a></li> <li><a href="/wiki/Epiestriol" title="Epiestriol">Epiestriol</a></li> <li><a href="/wiki/Epimestrol" title="Epimestrol">Epimestrol</a></li> <li><a href="/wiki/Esterified_estrogens" title="Esterified estrogens">Esterified estrogens</a></li> <li><a href="/wiki/Estetrol_(medication)" title="Estetrol (medication)">Estetrol</a><sup>†</sup></li> <li><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a></li> <li><a href="/wiki/List_of_estrogen_esters#Estradiol_esters" title="List of estrogen esters">Estradiol esters</a> (e.g., <a href="/wiki/Estradiol_acetate" title="Estradiol acetate">estradiol acetate</a>, <a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">estradiol benzoate</a>, <a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">estradiol cypionate</a>, <a href="/wiki/Estradiol_enanthate" class="mw-redirect" title="Estradiol enanthate">estradiol enanthate</a>, <a href="/wiki/Estradiol_undecylate" title="Estradiol undecylate">estradiol undecylate</a>, <a href="/wiki/Estradiol_valerate" title="Estradiol valerate">estradiol valerate</a>, <a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">polyestradiol phosphate</a>, <a href="/wiki/Estradiol_ester_mixture" class="mw-redirect" title="Estradiol ester mixture">estradiol ester mixtures</a> (<a href="/wiki/Climacteron" class="mw-redirect" title="Climacteron">Climacteron</a>))</li> <li><a href="/wiki/Estramustine_phosphate" title="Estramustine phosphate">Estramustine phosphate</a></li> <li><a href="/wiki/Estriol_(medication)" title="Estriol (medication)">Estriol</a></li> <li><a href="/wiki/List_of_estrogen_esters#Estriol_esters" title="List of estrogen esters">Estriol esters</a> (e.g., <a href="/wiki/Estriol_succinate" title="Estriol succinate">estriol succinate</a>, <a href="/wiki/Polyestriol_phosphate" title="Polyestriol phosphate">polyestriol phosphate</a>)</li> <li><a href="/wiki/Estrogenic_substances" title="Estrogenic substances">Estrogenic substances</a></li> <li><a href="/wiki/Estrone_(medication)" title="Estrone (medication)">Estrone</a></li> <li><a href="/wiki/List_of_estrogen_esters#Estrone_esters" title="List of estrogen esters">Estrone esters</a> <ul><li><a href="/wiki/Estrone_sulfate_(medication)" title="Estrone sulfate (medication)">Estrone sulfate</a></li> <li><a href="/wiki/Estropipate" title="Estropipate">Estropipate (piperazine estrone sulfate)</a></li></ul></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a><sup>#</sup> <ul><li><a href="/wiki/Ethinylestradiol_sulfonate" title="Ethinylestradiol sulfonate">Ethinylestradiol sulfonate</a></li></ul></li> <li><a href="/wiki/Hydroxyestrone_diacetate" title="Hydroxyestrone diacetate">Hydroxyestrone diacetate</a></li> <li><a href="/wiki/Mestranol" title="Mestranol">Mestranol</a></li> <li><a href="/wiki/Methylestradiol" title="Methylestradiol">Methylestradiol</a></li> <li><a href="/wiki/Moxestrol" title="Moxestrol">Moxestrol</a></li> <li><a href="/wiki/Nilestriol" title="Nilestriol">Nilestriol</a></li> <li><a href="/wiki/Prasterone" title="Prasterone">Prasterone (dehydroepiandrosterone; DHEA)</a> <ul><li><a href="/wiki/Prasterone_enanthate" title="Prasterone enanthate">Prasterone enanthate</a></li> <li><a href="/wiki/Prasterone_sulfate" title="Prasterone sulfate">Prasterone sulfate</a></li></ul></li> <li><a href="/wiki/Promestriene" title="Promestriene">Promestriene</a></li> <li><a href="/wiki/Quinestradol" title="Quinestradol">Quinestradol</a></li> <li><a href="/wiki/Quinestrol" title="Quinestrol">Quinestrol</a></li></ul> <ul><li><i>Nonsteroidal:</i> <a href="/wiki/Benzestrol" title="Benzestrol">Benzestrol</a></li> <li><a href="/wiki/Bifluranol" title="Bifluranol">Bifluranol</a></li> <li><a href="/wiki/Chlorotrianisene" title="Chlorotrianisene">Chlorotrianisene</a></li> <li><a href="/wiki/Dienestrol" title="Dienestrol">Dienestrol</a> <ul><li><a href="/wiki/Dienestrol_diacetate" title="Dienestrol diacetate">Dienestrol diacetate</a></li></ul></li> <li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol (stilbestrol)</a></li> <li><a href="/wiki/List_of_estrogen_esters#Diethylstilbestrol_esters" title="List of estrogen esters">Diethylstilbestrol esters/ethers</a> <ul><li><a href="/wiki/Dimestrol" title="Dimestrol">Dimestrol (diethylstilbestrol dimethyl ether)</a></li> <li><a href="/wiki/Fosfestrol" title="Fosfestrol">Fosfestrol (diethylstilbestrol diphosphate)</a></li> <li><a href="/wiki/Mestilbol" title="Mestilbol">Mestilbol (diethylstilbestrol monomethyl ether)</a></li></ul></li> <li><a href="/wiki/Doisynoestrol" title="Doisynoestrol">Doisynoestrol (fenocycline)</a></li> <li><a href="/wiki/Hexestrol" title="Hexestrol">Hexestrol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Hexestrol_esters" title="List of estrogen esters">Hexestrol esters</a></li></ul></li> <li><a href="/wiki/Methallenestril" title="Methallenestril">Methallenestril</a></li> <li><a href="/wiki/Methestrol" title="Methestrol">Methestrol (promethestrol)</a> <ul><li><a href="/wiki/Methestrol_dipropionate" title="Methestrol dipropionate">Methestrol dipropionate (promethestrol dipropionate)</a></li></ul></li> <li><a href="/wiki/Paroxypropione" title="Paroxypropione">Paroxypropione</a></li> <li><a href="/wiki/Quadrosilan" title="Quadrosilan">Quadrosilan</a></li> <li><a href="/wiki/Triphenylbromoethylene" title="Triphenylbromoethylene">Triphenylbromoethylene</a></li> <li><a href="/wiki/Triphenylchloroethylene" title="Triphenylchloroethylene">Triphenylchloroethylene</a></li> <li><a href="/wiki/Zeranol" title="Zeranol">Zeranol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Progonadotropin" title="Progonadotropin">Progonadotropins</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Antiandrogen" title="Antiandrogen">Antiandrogens</a> (e.g., <a href="/wiki/Bicalutamide" title="Bicalutamide">bicalutamide</a>)</li> <li><a href="/wiki/GnRH_agonist" class="mw-redirect" title="GnRH agonist"><abbr title="gonadotropin-releasing hormone">GnRH</abbr> agonists</a> (e.g., <a href="/wiki/Gonadotropin-releasing_hormone" title="Gonadotropin-releasing hormone"><abbr title="gonadotropin-releasing hormone">GnRH</abbr> (gonadorelin)</a>, <a href="/wiki/Leuprorelin" title="Leuprorelin">leuprorelin</a>)</li> <li><a href="/wiki/Gonadotropin" title="Gonadotropin">Gonadotropins</a> (e.g., <a href="/wiki/Follicle-stimulating_hormone" title="Follicle-stimulating hormone"><abbr title="follicle-stimulating hormone">FSH</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip follicle-stimulating hormone</span>, <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>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Antiestrogen" title="Antiestrogen">Antiestrogens</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0;background:#DDDDFF;"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor</span> antagonists<br />(incl. <a href="/wiki/Selective_estrogen_receptor_modulators" class="mw-redirect" title="Selective estrogen receptor modulators"><abbr title="selective estrogen receptor modulators">SERMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip selective estrogen receptor modulators</span>/<a href="/wiki/Selective_estrogen_receptor_downregulators" class="mw-redirect" title="Selective estrogen receptor downregulators"><abbr title="selective estrogen receptor downregulators">SERDs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip selective estrogen receptor downregulators</span>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acolbifene" title="Acolbifene">Acolbifene</a><sup>†</sup></li> <li><a href="/wiki/Anordrin" title="Anordrin">Anordrin</a></li> <li><a href="/wiki/Bazedoxifene" title="Bazedoxifene">Bazedoxifene</a></li> <li><a href="/wiki/Broparestrol" title="Broparestrol">Broparestrol</a></li> <li><a class="mw-selflink selflink">Clomifene</a><sup>#</sup></li> <li><a href="/wiki/Cyclofenil" title="Cyclofenil">Cyclofenil</a></li> <li><a href="/wiki/Enclomifene" title="Enclomifene">Enclomifene</a><sup>†</sup></li> <li><a href="/wiki/Epitiostanol" title="Epitiostanol">Epitiostanol</a></li> <li><a href="/wiki/Lasofoxifene" title="Lasofoxifene">Lasofoxifene</a></li> <li><a href="/wiki/Mepitiostane" title="Mepitiostane">Mepitiostane</a></li> <li><a href="/wiki/Ormeloxifene" title="Ormeloxifene">Ormeloxifene</a></li> <li><a href="/wiki/Ospemifene" title="Ospemifene">Ospemifene</a></li> <li><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a><sup>#</sup></li> <li><a href="/wiki/Toremifene" title="Toremifene">Toremifene</a></li></ul> <ul><li><i>Exclusively antagonistic:</i> <a href="/wiki/Elacestrant" title="Elacestrant">Elacestrant</a></li> <li><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant</a></li></ul> <ul><li><i>Noncompetitive inhibitors:</i> <a href="/wiki/Trilostane" title="Trilostane">Trilostane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Aromatase_inhibitor" title="Aromatase inhibitor">Aromatase inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>First-generation:</i> <a href="/wiki/Aminoglutethimide" title="Aminoglutethimide">Aminoglutethimide</a></li> <li><a href="/wiki/Testolactone" title="Testolactone">Testolactone</a></li></ul> <ul><li><i>Second-generation:</i> <a href="/wiki/Fadrozole" title="Fadrozole">Fadrozole</a></li> <li><a href="/wiki/Formestane" title="Formestane">Formestane</a></li></ul> <ul><li><i>Third-generation:</i> <a href="/wiki/Anastrozole" title="Anastrozole">Anastrozole</a></li> <li><a href="/wiki/Exemestane" title="Exemestane">Exemestane</a></li> <li><a href="/wiki/Letrozole" title="Letrozole">Letrozole</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Antigonadotropin" title="Antigonadotropin">Antigonadotropins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Androgen" title="Androgen">Androgens</a>/<a href="/wiki/Anabolic_steroid" title="Anabolic steroid">anabolic steroids</a> (e.g., <a href="/wiki/Testosterone" title="Testosterone">testosterone</a>, <a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">testosterone esters</a>, <a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">nandrolone esters</a>, <a href="/wiki/Oxandrolone" title="Oxandrolone">oxandrolone</a>, <a href="/wiki/Fluoxymesterone" title="Fluoxymesterone">fluoxymesterone</a>)</li> <li><a href="/wiki/D2_receptor" class="mw-redirect" title="D2 receptor">D<sub>2</sub> receptor</a> <a href="/wiki/Dopamine_antagonist" title="Dopamine antagonist">antagonists</a> (<a href="/wiki/Prolactin" title="Prolactin">prolactin</a> releasers) (e.g., <a href="/wiki/Domperidone" title="Domperidone">domperidone</a>, <a href="/wiki/Metoclopramide" title="Metoclopramide">metoclopramide</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>, <a href="/wiki/Haloperidol" title="Haloperidol">haloperidol</a>, <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>, <a href="/wiki/Sulpiride" title="Sulpiride">sulpiride</a>)</li> <li><a href="/wiki/GnRH_agonist" class="mw-redirect" title="GnRH agonist"><abbr title="gonadotropin-releasing hormone">GnRH</abbr> agonists</a> (e.g., <a href="/wiki/Leuprorelin" title="Leuprorelin">leuprorelin</a>, <a href="/wiki/Goserelin" title="Goserelin">goserelin</a>)</li> <li><a href="/wiki/GnRH_antagonist" class="mw-redirect" title="GnRH antagonist"><abbr title="gonadotropin-releasing hormone">GnRH</abbr> antagonists</a> (e.g., <a href="/wiki/Cetrorelix" title="Cetrorelix">cetrorelix</a>, <a href="/wiki/Elagolix" title="Elagolix">elagolix</a>)</li> <li><a href="/wiki/Progestogen" title="Progestogen">Progestogens</a> (e.g., <a href="/wiki/Chlormadinone_acetate" title="Chlormadinone acetate">chlormadinone acetate</a>, <a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">cyproterone acetate</a>, <a href="/wiki/Gestonorone_caproate" title="Gestonorone caproate">gestonorone caproate</a>, <a href="/wiki/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">hydroxyprogesterone caproate</a>, <a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">medroxyprogesterone acetate</a>, <a href="/wiki/Megestrol_acetate" title="Megestrol acetate">megestrol acetate</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Mixed mechanism of action:</i> <a href="/wiki/Danazol" title="Danazol">Danazol</a></li> <li><a href="/wiki/Gestrinone" title="Gestrinone">Gestrinone</a></li></ul> <ul><li><i>Androstenedione immunogens:</i> <a href="/wiki/Androvax" title="Androvax">Androvax (androstenedione albumin)</a></li> <li><a href="/wiki/Ovandrotone_albumin" title="Ovandrotone albumin">Ovandrotone albumin (Fecundin)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0;background:#DDDDFF;"><div style="padding:0 0.25em"><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators">Estrogen receptor modulators</a></dd> <dd><a href="/wiki/Template:Androgens_and_antiandrogens" title="Template:Androgens and antiandrogens">Androgens and antiandrogens</a></dd> <dd><a href="/wiki/Template:Progestogens_and_antiprogestogens" title="Template:Progestogens and antiprogestogens">Progestogens and antiprogestogens</a></dd> <dd><a href="/wiki/List_of_steroidal_estrogens" class="mw-redirect" title="List of steroidal estrogens">List of estrogens</a></dd></dl></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Assisted_reproductive_technology" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse 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:Assisted_reproductive_technology" title="Template:Assisted reproductive technology"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Assisted_reproductive_technology" title="Template talk:Assisted reproductive technology"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Assisted_reproductive_technology" title="Special:EditPage/Template:Assisted reproductive technology"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Assisted_reproductive_technology" style="font-size:114%;margin:0 4em"><a href="/wiki/Assisted_reproductive_technology" title="Assisted reproductive technology">Assisted reproductive technology</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Infertility" title="Infertility">Infertility</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/Female_infertility" title="Female infertility">Female</a></li> <li><a href="/wiki/Male_infertility" title="Male infertility">Male</a></li> <li><a href="/wiki/LGBT_reproduction" class="mw-redirect" title="LGBT reproduction">LGBT</a></li> <li><a href="/wiki/Fertility_clinic" title="Fertility clinic">Fertility clinic</a></li> <li><a href="/wiki/Fertility_testing" title="Fertility testing">Fertility testing</a></li> <li><a href="/wiki/Fertility_tourism" title="Fertility tourism">Fertility tourism</a></li> <li><a href="/wiki/Male_infertility_crisis" title="Male infertility crisis">Male infertility crisis</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Fertility_medication" title="Fertility medication">Fertility medication</a></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><a href="/wiki/Estrogen_antagonist" class="mw-redirect" title="Estrogen antagonist">Estrogen antagonists</a> <ul><li><a href="/wiki/Aromatase_inhibitor" title="Aromatase inhibitor">aromatase inhibitor</a></li> <li><a class="mw-selflink selflink">clomifene</a></li></ul></li> <li><a href="/wiki/Follicle-stimulating_hormone" title="Follicle-stimulating hormone">FSH</a></li> <li><a href="/wiki/Gonadotropin-releasing_hormone_agonist" title="Gonadotropin-releasing hormone agonist">GnRH agonists</a></li> <li><a href="/wiki/Gonadotropin" title="Gonadotropin">Gonadotropins</a> <ul><li><a href="/wiki/Menotropin" title="Menotropin">menotropins</a></li></ul></li> <li><a href="/wiki/Human_chorionic_gonadotropin#Use_as_medication" title="Human chorionic gonadotropin">hCG</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/In_vitro_fertilisation" title="In vitro fertilisation">In vitro fertilisation</a> (IVF)<br /> and expansions</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/Assisted_zona_hatching" title="Assisted zona hatching">Assisted zona hatching</a></li> <li><a href="/wiki/Autologous_endometrial_coculture" title="Autologous endometrial coculture">Autologous endometrial coculture</a></li> <li><a href="/wiki/Cytoplasmic_transfer" class="mw-redirect" title="Cytoplasmic transfer">Cytoplasmic transfer</a></li> <li><a href="/wiki/Embryo_transfer" title="Embryo transfer">Embryo transfer</a></li> <li><a href="/wiki/Gestational_carrier" class="mw-redirect" title="Gestational carrier">Gestational carrier</a></li> <li><a href="/wiki/In_vitro_maturation" title="In vitro maturation">In vitro maturation</a></li> <li><a href="/wiki/Intracytoplasmic_sperm_injection" title="Intracytoplasmic sperm injection">Intracytoplasmic sperm injection</a></li> <li><a href="/wiki/Oocyte_selection" title="Oocyte selection">Oocyte selection</a></li> <li><a href="/wiki/Controlled_ovarian_hyperstimulation" title="Controlled ovarian hyperstimulation">Ovarian hyperstimulation</a></li> <li><a href="/wiki/Partner-assisted_reproduction" title="Partner-assisted reproduction">Partner-assisted reproduction</a></li> <li><a href="/wiki/Preimplantation_genetic_diagnosis" title="Preimplantation genetic diagnosis">Preimplantation genetic diagnosis</a></li> <li><a href="/wiki/Transvaginal_oocyte_retrieval" title="Transvaginal oocyte retrieval">Transvaginal ovum retrieval</a></li> <li><a href="/wiki/Zygote_intrafallopian_transfer" title="Zygote intrafallopian transfer">Zygote intrafallopian transfer</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other methods</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><a href="/wiki/Artificial_insemination" title="Artificial insemination">Artificial insemination</a></li> <li><a href="/wiki/Ovulation_induction" title="Ovulation induction">Ovulation induction</a></li> <li><a href="/wiki/Cryopreservation" title="Cryopreservation">Cryopreservation</a> <ul><li><a href="/wiki/Embryo_cryopreservation" title="Embryo cryopreservation">embryos</a></li> <li><a href="/wiki/Oocyte_cryopreservation" title="Oocyte cryopreservation">oocyte</a></li> <li><a href="/wiki/Ovarian_tissue_cryopreservation" title="Ovarian tissue cryopreservation">ovarian tissue</a></li> <li><a href="/wiki/Semen_cryopreservation" title="Semen cryopreservation">semen</a></li></ul></li> <li><a href="/wiki/Gamete_intrafallopian_transfer" title="Gamete intrafallopian transfer">Gamete intrafallopian transfer</a></li> <li><a href="/wiki/Reproductive_surgery" title="Reproductive surgery">Reproductive surgery</a> <ul><li><a href="/wiki/Vasectomy_reversal" title="Vasectomy reversal">Vasectomy reversal</a></li></ul></li> <li><a href="/wiki/Selective_reduction" title="Selective reduction">Selective reduction</a></li> <li><a href="/wiki/Sex_selection" title="Sex selection">Sex selection</a></li> <li><a href="/wiki/Surrogacy" title="Surrogacy">Surrogacy</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Donation</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/Donor_registration" title="Donor registration">Donor registration</a></li> <li><a href="/wiki/Donor_Sibling_Registry" title="Donor Sibling Registry">Donor Sibling Registry</a></li> <li><a href="/wiki/Egg_donation" title="Egg donation">Egg donation</a></li> <li><a href="/wiki/Embryo_donation" title="Embryo donation">Embryo</a></li> <li><a href="/wiki/Sperm_donation" title="Sperm donation">Sperm</a></li> <li><a href="/wiki/Semen_collection" title="Semen collection">Semen collection</a></li> <li><a href="/wiki/Sperm_bank" title="Sperm bank">Sperm bank</a></li> <li><a href="/wiki/Ova_bank" title="Ova bank">Ova bank</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Ethics</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><a href="/wiki/Accidental_incest" title="Accidental incest">Accidental incest</a></li> <li><a href="/wiki/Fertility_fraud" title="Fertility fraud">Fertility fraud</a></li> <li><a href="/wiki/Genetic_diagnosis_of_intersex" title="Genetic diagnosis of intersex">Genetic diagnosis of intersex</a></li> <li><a href="/wiki/Religious_response_to_assisted_reproductive_technology" title="Religious response to assisted reproductive technology">Religious response to ART</a></li> <li><a href="/wiki/Mitochondrial_donation" class="mw-redirect" title="Mitochondrial donation">Mitochondrial donation</a></li> <li><a href="/wiki/Sex_selection" title="Sex selection">Sex selection</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Related</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/Reproduction_and_pregnancy_in_speculative_fiction" title="Reproduction and pregnancy in speculative fiction">Reproduction and pregnancy in speculative fiction</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_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Estrogen_receptor_modulators" title="Template talk:Estrogen receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Estrogen_receptor_modulators" title="Special:EditPage/Template:Estrogen receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Estrogen_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor">Estrogen receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor</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 href="/wiki/Estriol" title="Estriol">Estriol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estriol_esters" title="List of estrogen esters">Estriol esters</a></li> <li><a href="/wiki/Polyestriol_phosphate" title="Polyestriol phosphate">Polyestriol phosphate</a></li></ul></li> <li><a href="/wiki/Estrofurate" title="Estrofurate">Estrofurate</a></li> <li><a href="/wiki/Estrogenic_substances" title="Estrogenic substances">Estrogenic substances</a></li> <li><a href="/wiki/Estromustine" title="Estromustine">Estromustine</a></li> <li><a href="/wiki/Estrone" title="Estrone">Estrone</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estrone_esters" title="List of estrogen esters">Estrone esters</a></li> <li><a href="/wiki/Estrone_methyl_ether" title="Estrone methyl ether">Estrone methyl ether</a></li> <li><a href="/wiki/Estropipate" title="Estropipate">Estropipate</a></li></ul></li> <li><a href="/wiki/Etamestrol" title="Etamestrol">Etamestrol (eptamestrol)</a></li> <li><a href="/wiki/Ethinylandrostenediol" title="Ethinylandrostenediol">Ethinylandrostenediol</a> <ul><li><a href="/wiki/Ethandrostate" title="Ethandrostate">Ethandrostate</a></li></ul></li> <li><a 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 class="mw-selflink selflink">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="/w/index.php?title=G-1_(drug)&action=edit&redlink=1" class="new" title="G-1 (drug) (page does not exist)">G-1</a></li> <li><a href="/wiki/Genistein" title="Genistein">Genistein</a></li> <li><a href="/w/index.php?title=GPER-L1&action=edit&redlink=1" class="new" title="GPER-L1 (page does not exist)">GPER-L1</a></li> <li><a href="/w/index.php?title=GPER-L2&action=edit&redlink=1" class="new" title="GPER-L2 (page does not exist)">GPER-L2</a></li> <li><a href="/wiki/Hydroxytyrosol" title="Hydroxytyrosol">Hydroxytyrosol</a></li> <li><a href="/wiki/Kepone" class="mw-redirect" title="Kepone">Kepone</a></li> <li><a href="/wiki/Niacin" title="Niacin">Niacin</a></li> <li><a href="/wiki/Niacinamide" class="mw-redirect" title="Niacinamide">Niacinamide</a></li> <li><a href="/wiki/Nonylphenol" title="Nonylphenol">Nonylphenol</a></li> <li><a href="/wiki/Oleuropein" title="Oleuropein">Oleuropein</a></li> <li><a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">PCBs</a> (<a href="/w/index.php?title=2,2%27,5%27-PCB-4-OH&action=edit&redlink=1" class="new" title="2,2',5'-PCB-4-OH (page does not exist)">2,2',5'-PCB-4-OH</a>)</li> <li><a href="/wiki/Propylpyrazoletriol" title="Propylpyrazoletriol">Propylpyrazoletriol</a></li> <li><a href="/wiki/Quercetin" title="Quercetin">Quercetin</a></li> <li><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></li> <li><a href="/wiki/Resveratrol" title="Resveratrol">Resveratrol</a></li> <li><a href="/w/index.php?title=STX_(drug)&action=edit&redlink=1" class="new" title="STX (drug) (page does not exist)">STX</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a></li> <li><a href="/wiki/Tectoridin" title="Tectoridin">Tectoridin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/CCL18" title="CCL18">CCL18</a></li> <li><a href="/wiki/Estriol" title="Estriol">Estriol</a></li> <li><a href="/w/index.php?title=G-15_(drug)&action=edit&redlink=1" class="new" title="G-15 (drug) (page does not exist)">G-15</a></li> <li><a href="/w/index.php?title=G-36_(drug)&action=edit&redlink=1" class="new" title="G-36 (drug) (page does not exist)">G-36</a></li> <li><a href="/wiki/MIBE" title="MIBE">MIBE</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Unknown</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a></li> <li><a href="/wiki/Zearalenone" title="Zearalenone">Zearalenone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Estrogens_and_antiestrogens" title="Template:Estrogens and antiestrogens">Estrogens and antiestrogens</a></dd> 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