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id="toc-Female_pubertal_development-sublist" class="vector-toc-list"> <li id="toc-Breast_development" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Breast_development"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2.1</span> <span>Breast development</span> </div> </a> <ul id="toc-Breast_development-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Female_reproductive_system" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Female_reproductive_system"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Female reproductive system</span> </div> </a> <ul id="toc-Female_reproductive_system-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Neuroprotection_and_DNA_repair" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Neuroprotection_and_DNA_repair"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.4</span> <span>Neuroprotection and DNA repair</span> </div> </a> <ul id="toc-Neuroprotection_and_DNA_repair-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Brain_and_behavior" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Brain_and_behavior"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.5</span> <span>Brain and behavior</span> </div> </a> <ul id="toc-Brain_and_behavior-sublist" class="vector-toc-list"> <li id="toc-Sex_drive" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Sex_drive"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.5.1</span> <span>Sex drive</span> </div> </a> <ul id="toc-Sex_drive-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cognition" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Cognition"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.5.2</span> <span>Cognition</span> </div> </a> <ul id="toc-Cognition-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Mental_health" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Mental_health"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.5.3</span> <span>Mental health</span> </div> </a> <ul id="toc-Mental_health-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Parenthood" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Parenthood"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.5.4</span> <span>Parenthood</span> </div> </a> <ul id="toc-Parenthood-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Binge_eating" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Binge_eating"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.5.5</span> <span>Binge eating</span> </div> </a> <ul id="toc-Binge_eating-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Masculinization_in_rodents" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Masculinization_in_rodents"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.5.6</span> <span>Masculinization in rodents</span> </div> </a> <ul id="toc-Masculinization_in_rodents-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Skeletal_system" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Skeletal_system"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.6</span> <span>Skeletal system</span> </div> </a> <ul id="toc-Skeletal_system-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cardiovascular_system" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cardiovascular_system"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.7</span> <span>Cardiovascular system</span> </div> </a> <ul id="toc-Cardiovascular_system-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Immune_system" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Immune_system"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.8</span> <span>Immune system</span> </div> </a> <ul id="toc-Immune_system-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Associated_conditions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Associated_conditions"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.9</span> <span>Associated conditions</span> </div> </a> <ul id="toc-Associated_conditions-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Biochemistry" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Biochemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Biochemistry</span> </div> </a> <button aria-controls="toc-Biochemistry-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Biochemistry subsection</span> </button> <ul id="toc-Biochemistry-sublist" class="vector-toc-list"> <li id="toc-Biosynthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Biosynthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Biosynthesis</span> </div> </a> <ul id="toc-Biosynthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Distribution" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Distribution"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Distribution</span> </div> </a> <ul id="toc-Distribution-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metabolism" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Metabolism"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Metabolism</span> </div> </a> <ul id="toc-Metabolism-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Excretion" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Excretion"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>Excretion</span> </div> </a> <ul id="toc-Excretion-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Medical_use" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Medical_use"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Medical use</span> </div> </a> <ul id="toc-Medical_use-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Chemistry" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Chemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</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"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</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"> <a class="vector-toc-link" href="#Society_and_culture"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</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-Etymology" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Etymology"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.1</span> <span>Etymology</span> </div> </a> <ul id="toc-Etymology-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Environment" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Environment"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.2</span> <span>Environment</span> </div> </a> <ul id="toc-Environment-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cosmetics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cosmetics"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.3</span> <span>Cosmetics</span> </div> </a> <ul id="toc-Cosmetics-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Estrogen</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 77 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-77" 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">77 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A5%D8%B3%D8%AA%D8%B1%D9%88%D8%AC%D9%8A%D9%86" title="إستروجين – Arabic" lang="ar" hreflang="ar" data-title="إستروجين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-as mw-list-item"><a href="https://as.wikipedia.org/wiki/%E0%A6%8F%E0%A6%B7%E0%A7%8D%E0%A6%9F%E0%A7%8D%E0%A7%B0%E0%A7%8B%E0%A6%9C%E0%A7%87%E0%A6%A8" title="এষ্ট্ৰোজেন – Assamese" lang="as" hreflang="as" data-title="এষ্ট্ৰোজেন" data-language-autonym="অসমীয়া" data-language-local-name="Assamese" class="interlanguage-link-target"><span>অসমীয়া</span></a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/Estr%C3%B3xenu" title="Estróxenu – Asturian" lang="ast" hreflang="ast" data-title="Estróxenu" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target"><span>Asturianu</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Estrogen" title="Estrogen – Azerbaijani" lang="az" hreflang="az" data-title="Estrogen" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%87%E0%A6%B8%E0%A7%8D%E0%A6%9F%E0%A7%8D%E0%A6%B0%E0%A7%8B%E0%A6%9C%E0%A7%87%E0%A6%A8" title="ইস্ট্রোজেন – Bangla" lang="bn" hreflang="bn" data-title="ইস্ট্রোজেন" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%AD%D1%81%D1%82%D1%80%D0%B0%D0%B3%D0%B5%D0%BD%D1%8B" title="Эстрагены – Belarusian" lang="be" hreflang="be" data-title="Эстрагены" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-be-x-old mw-list-item"><a href="https://be-tarask.wikipedia.org/wiki/%D0%AD%D1%81%D1%82%D1%80%D0%B0%D0%B3%D0%B5%D0%BD%D1%8B" title="Эстрагены – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Эстрагены" data-language-autonym="Беларуская (тарашкевіца)" data-language-local-name="Belarusian (Taraškievica orthography)" class="interlanguage-link-target"><span>Беларуская (тарашкевіца)</span></a></li><li class="interlanguage-link interwiki-bcl mw-list-item"><a href="https://bcl.wikipedia.org/wiki/Estroheno" title="Estroheno – Central Bikol" lang="bcl" hreflang="bcl" data-title="Estroheno" data-language-autonym="Bikol Central" data-language-local-name="Central Bikol" class="interlanguage-link-target"><span>Bikol Central</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%95%D1%81%D1%82%D1%80%D0%BE%D0%B3%D0%B5%D0%BD" title="Естроген – Bulgarian" lang="bg" hreflang="bg" data-title="Естроген" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Estrogen" title="Estrogen – Bosnian" lang="bs" hreflang="bs" data-title="Estrogen" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Estrogen" title="Estrogen – Catalan" lang="ca" hreflang="ca" data-title="Estrogen" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Estrogen" title="Estrogen – Czech" lang="cs" hreflang="cs" data-title="Estrogen" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/%C3%98strogen" title="Østrogen – Danish" lang="da" hreflang="da" data-title="Østrogen" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Estrogene" title="Estrogene – German" lang="de" hreflang="de" data-title="Estrogene" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-dv mw-list-item"><a href="https://dv.wikipedia.org/wiki/%DE%87%DE%AC%DE%90%DE%B0%DE%93%DE%B0%DE%83%DE%A6%DE%96%DE%A6%DE%82%DE%B0" title="އެސްޓްރަޖަން – Divehi" lang="dv" hreflang="dv" data-title="އެސްޓްރަޖަން" data-language-autonym="ދިވެހިބަސް" data-language-local-name="Divehi" class="interlanguage-link-target"><span>ދިވެހިބަސް</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/%C3%96strogeenid" title="Östrogeenid – Estonian" lang="et" hreflang="et" data-title="Östrogeenid" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9F%CE%B9%CF%83%CF%84%CF%81%CE%BF%CE%B3%CF%8C%CE%BD%CE%BF" title="Οιστρογόνο – Greek" lang="el" hreflang="el" data-title="Οιστρογόνο" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Estr%C3%B3geno" title="Estrógeno – Spanish" lang="es" hreflang="es" data-title="Estrógeno" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Estrogeno" title="Estrogeno – Esperanto" lang="eo" hreflang="eo" data-title="Estrogeno" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Estrogeno" title="Estrogeno – Basque" lang="eu" hreflang="eu" data-title="Estrogeno" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%D8%B3%D8%AA%D8%B1%D9%88%DA%98%D9%86" title="استروژن – Persian" lang="fa" hreflang="fa" data-title="استروژن" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fo mw-list-item"><a href="https://fo.wikipedia.org/wiki/%C3%98strogen" title="Østrogen – Faroese" lang="fo" hreflang="fo" data-title="Østrogen" data-language-autonym="Føroyskt" data-language-local-name="Faroese" class="interlanguage-link-target"><span>Føroyskt</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/%C5%92strog%C3%A8ne" title="Œstrogène – French" lang="fr" hreflang="fr" data-title="Œstrogène" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/%C3%89astraigin" title="Éastraigin – Irish" lang="ga" hreflang="ga" data-title="Éastraigin" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Estr%C3%B3xeno" title="Estróxeno – Galician" lang="gl" hreflang="gl" data-title="Estróxeno" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%97%90%EC%8A%A4%ED%8A%B8%EB%A1%9C%EA%B2%90" title="에스트로겐 – Korean" lang="ko" hreflang="ko" data-title="에스트로겐" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%B7%D5%BD%D5%BF%D6%80%D5%B8%D5%A3%D5%A5%D5%B6%D5%B6%D5%A5%D6%80" title="Էստրոգեններ – Armenian" lang="hy" hreflang="hy" data-title="Էստրոգեններ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Estrogeni" title="Estrogeni – Croatian" lang="hr" hreflang="hr" data-title="Estrogeni" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Estrogen" title="Estrogen – Indonesian" lang="id" hreflang="id" data-title="Estrogen" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-ia mw-list-item"><a href="https://ia.wikipedia.org/wiki/Estrogeno" title="Estrogeno – Interlingua" lang="ia" hreflang="ia" data-title="Estrogeno" data-language-autonym="Interlingua" data-language-local-name="Interlingua" class="interlanguage-link-target"><span>Interlingua</span></a></li><li class="interlanguage-link interwiki-is mw-list-item"><a href="https://is.wikipedia.org/wiki/Estr%C3%B3gen" title="Estrógen – Icelandic" lang="is" hreflang="is" data-title="Estrógen" data-language-autonym="Íslenska" data-language-local-name="Icelandic" class="interlanguage-link-target"><span>Íslenska</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Estrogeno" title="Estrogeno – Italian" lang="it" hreflang="it" data-title="Estrogeno" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%90%D7%A1%D7%98%D7%A8%D7%95%D7%92%D7%9F" title="אסטרוגן – Hebrew" lang="he" hreflang="he" data-title="אסטרוגן" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-jv mw-list-item"><a href="https://jv.wikipedia.org/wiki/Estrogen" title="Estrogen – Javanese" lang="jv" hreflang="jv" data-title="Estrogen" data-language-autonym="Jawa" data-language-local-name="Javanese" class="interlanguage-link-target"><span>Jawa</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%94%E1%83%A1%E1%83%A2%E1%83%A0%E1%83%9D%E1%83%92%E1%83%94%E1%83%9C%E1%83%98" title="ესტროგენი – Georgian" lang="ka" hreflang="ka" data-title="ესტროგენი" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%AD%D1%81%D1%82%D1%80%D0%BE%D0%B3%D0%B5%D0%BD" title="Эстроген – Kazakh" lang="kk" hreflang="kk" data-title="Эстроген" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-sw mw-list-item"><a href="https://sw.wikipedia.org/wiki/Estrojeni" title="Estrojeni – Swahili" lang="sw" hreflang="sw" data-title="Estrojeni" data-language-autonym="Kiswahili" data-language-local-name="Swahili" class="interlanguage-link-target"><span>Kiswahili</span></a></li><li class="interlanguage-link interwiki-ku mw-list-item"><a href="https://ku.wikipedia.org/wiki/%C3%8Astrocen" title="Êstrocen – Kurdish" lang="ku" hreflang="ku" data-title="Êstrocen" data-language-autonym="Kurdî" data-language-local-name="Kurdish" class="interlanguage-link-target"><span>Kurdî</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%AD%D1%81%D1%82%D1%80%D0%BE%D0%B3%D0%B5%D0%BD" title="Эстроген – Kyrgyz" lang="ky" hreflang="ky" data-title="Эстроген" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Oestrogenum" title="Oestrogenum – Latin" lang="la" hreflang="la" data-title="Oestrogenum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Estrog%C4%93ns" title="Estrogēns – Latvian" lang="lv" hreflang="lv" data-title="Estrogēns" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Estrogenai" title="Estrogenai – Lithuanian" lang="lt" hreflang="lt" data-title="Estrogenai" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/T%C3%BCsz%C5%91hormon" title="Tüszőhormon – Hungarian" lang="hu" hreflang="hu" data-title="Tüszőhormon" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%95%D1%81%D1%82%D1%80%D0%BE%D0%B3%D0%B5%D0%BD" title="Естроген – Macedonian" lang="mk" hreflang="mk" data-title="Естроген" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%88%E0%B4%B8%E0%B5%8D%E0%B4%9F%E0%B5%8D%E0%B4%B0%E0%B4%9C%E0%B5%BB" title="ഈസ്ട്രജൻ – Malayalam" lang="ml" hreflang="ml" data-title="ഈസ്ട്രജൻ" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Estrogen" title="Estrogen – Malay" lang="ms" hreflang="ms" data-title="Estrogen" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Oestrogeen" title="Oestrogeen – Dutch" lang="nl" hreflang="nl" data-title="Oestrogeen" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A8%E3%82%B9%E3%83%88%E3%83%AD%E3%82%B2%E3%83%B3" title="エストロゲン – Japanese" lang="ja" hreflang="ja" data-title="エストロゲン" 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/%C3%98strogen" title="Østrogen – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Østrogen" 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-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/%C3%98strogen" title="Østrogen – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Østrogen" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Estrog%C3%A8n" title="Estrogèn – Occitan" lang="oc" hreflang="oc" data-title="Estrogèn" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Estrogenlar" title="Estrogenlar – Uzbek" lang="uz" hreflang="uz" data-title="Estrogenlar" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pnb mw-list-item"><a href="https://pnb.wikipedia.org/wiki/%D8%A7%DB%8C%D8%B3%D9%B9%D8%B1%D9%88%D8%AC%D9%86" title="ایسٹروجن – Western Punjabi" lang="pnb" hreflang="pnb" data-title="ایسٹروجن" data-language-autonym="پنجابی" data-language-local-name="Western Punjabi" class="interlanguage-link-target"><span>پنجابی</span></a></li><li class="interlanguage-link interwiki-ps mw-list-item"><a href="https://ps.wikipedia.org/wiki/%D8%A7%DB%90%D8%B3%D9%BC%D8%B1%D9%88%D8%AC%D9%86" title="اېسټروجن – Pashto" lang="ps" hreflang="ps" data-title="اېسټروجن" data-language-autonym="پښتو" data-language-local-name="Pashto" class="interlanguage-link-target"><span>پښتو</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Estrogeny" title="Estrogeny – Polish" lang="pl" hreflang="pl" data-title="Estrogeny" 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/Estrog%C3%AAnio" title="Estrogênio – Portuguese" lang="pt" hreflang="pt" data-title="Estrogênio" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Estrogen" title="Estrogen – Romanian" lang="ro" hreflang="ro" data-title="Estrogen" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%AD%D1%81%D1%82%D1%80%D0%BE%D0%B3%D0%B5%D0%BD%D1%8B" title="Эстрогены – Russian" lang="ru" hreflang="ru" data-title="Эстрогены" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sah mw-list-item"><a href="https://sah.wikipedia.org/wiki/%D0%AD%D1%81%D1%82%D1%80%D0%BE%D0%B3%D0%B5%D0%BD%D0%BD%D0%B0%D1%80" title="Эстрогеннар – Yakut" lang="sah" hreflang="sah" data-title="Эстрогеннар" data-language-autonym="Саха тыла" data-language-local-name="Yakut" class="interlanguage-link-target"><span>Саха тыла</span></a></li><li class="interlanguage-link interwiki-sco mw-list-item"><a href="https://sco.wikipedia.org/wiki/Estrogen" title="Estrogen – Scots" lang="sco" hreflang="sco" data-title="Estrogen" data-language-autonym="Scots" data-language-local-name="Scots" class="interlanguage-link-target"><span>Scots</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Estrogen" title="Estrogen – Simple English" lang="en-simple" hreflang="en-simple" data-title="Estrogen" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Estrog%C3%A9n" title="Estrogén – Slovak" lang="sk" hreflang="sk" data-title="Estrogén" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Estrogen" title="Estrogen – Slovenian" lang="sl" hreflang="sl" data-title="Estrogen" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-ckb mw-list-item"><a href="https://ckb.wikipedia.org/wiki/%D8%A6%DB%8E%D8%B3%D8%AA%D8%B1%DB%86%D8%AC%DB%8C%D9%86" title="ئێسترۆجین – Central Kurdish" lang="ckb" hreflang="ckb" data-title="ئێسترۆجین" data-language-autonym="کوردی" data-language-local-name="Central Kurdish" class="interlanguage-link-target"><span>کوردی</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%95%D1%81%D1%82%D1%80%D0%BE%D0%B3%D0%B5%D0%BD" title="Естроген – Serbian" lang="sr" hreflang="sr" data-title="Естроген" 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/Estrogeni" title="Estrogeni – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Estrogeni" 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-su mw-list-item"><a href="https://su.wikipedia.org/wiki/%C3%89strog%C3%A9n" title="Éstrogén – Sundanese" lang="su" hreflang="su" data-title="Éstrogén" data-language-autonym="Sunda" data-language-local-name="Sundanese" class="interlanguage-link-target"><span>Sunda</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Estrogeenit" title="Estrogeenit – Finnish" lang="fi" hreflang="fi" data-title="Estrogeenit" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/%C3%96strogen" title="Östrogen – Swedish" lang="sv" hreflang="sv" data-title="Östrogen" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%88%E0%AE%A4%E0%AF%8D%E0%AE%A4%E0%AE%BF%E0%AE%B0%E0%AF%8B%E0%AE%9A%E0%AE%A9%E0%AF%8D" title="ஈத்திரோசன் – Tamil" lang="ta" hreflang="ta" data-title="ஈத்திரோசன்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%80%E0%B8%AD%E0%B8%AA%E0%B9%82%E0%B8%95%E0%B8%A3%E0%B9%80%E0%B8%88%E0%B8%99" title="เอสโตรเจน – Thai" lang="th" hreflang="th" data-title="เอสโตรเจน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/%C3%96strojen" title="Östrojen – Turkish" lang="tr" hreflang="tr" data-title="Östrojen" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%95%D1%81%D1%82%D1%80%D0%BE%D0%B3%D0%B5%D0%BD%D0%B8" title="Естрогени – Ukrainian" lang="uk" hreflang="uk" data-title="Естрогени" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Estrogen" title="Estrogen – Vietnamese" lang="vi" hreflang="vi" data-title="Estrogen" 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-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E9%9B%8C%E6%BF%80%E7%B4%A0" title="雌激素 – Wu" lang="wuu" hreflang="wuu" data-title="雌激素" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E5%A5%B3%E6%80%A7%E8%B3%80%E7%88%BE%E8%92%99" title="女性賀爾蒙 – Cantonese" lang="yue" hreflang="yue" data-title="女性賀爾蒙" 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/%E9%9B%8C%E6%BF%80%E7%B4%A0" title="雌激素 – Chinese" lang="zh" hreflang="zh" data-title="雌激素" 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 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searchaux" style="display:none">Primary female sex hormone</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">This article is about estrogens as hormones. For their use as medications, see <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogen (medication)</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"><tbody><tr><th colspan="2" class="infobox-above" style="background-color: #ddbbee">Estrogen</th></tr><tr><td colspan="2" class="infobox-subheader"><i><a href="/wiki/Drug_class" title="Drug class">Drug class</a></i></td></tr><tr><td colspan="2" class="infobox-image"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Estradiol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Estradiol.svg/225px-Estradiol.svg.png" decoding="async" width="225" height="142" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Estradiol.svg/338px-Estradiol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/00/Estradiol.svg/450px-Estradiol.svg.png 2x" data-file-width="512" data-file-height="324" /></a></span><div class="infobox-caption"><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a>, the major estrogen sex hormone in humans and a widely used medication</div></td></tr><tr><th colspan="2" class="infobox-header" style="background: #e8e8e8;">Class identifiers</th></tr><tr><th scope="row" class="infobox-label">Use</th><td class="infobox-data"><a href="/wiki/Hormonal_contraception" title="Hormonal contraception">Contraception</a>, <a href="/wiki/Menopause" title="Menopause">menopause</a>, <a href="/wiki/Hypogonadism" title="Hypogonadism">hypogonadism</a>, <a href="/wiki/Feminizing_hormone_therapy" title="Feminizing hormone therapy">transgender women</a>, <a href="/wiki/Prostate_cancer" title="Prostate cancer">prostate cancer</a>, <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a>, others</td></tr><tr><th scope="row" class="infobox-label"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><a href="/wiki/ATC_code_G03C" class="mw-redirect" title="ATC code G03C">G03C</a></td></tr><tr><th scope="row" class="infobox-label"><a href="/wiki/Biological_target" title="Biological target">Biological target</a></th><td class="infobox-data"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor">Estrogen receptors</a> (<a href="/wiki/ER%CE%B1" class="mw-redirect" title="ERα">ERα</a>, <a href="/wiki/ER%CE%B2" class="mw-redirect" title="ERβ">ERβ</a>, <a href="/wiki/Membrane_estrogen_receptor" title="Membrane estrogen receptor">mERs</a> (e.g., <a href="/wiki/GPER" title="GPER">GPER</a>, others))</td></tr><tr><th colspan="2" class="infobox-header" style="background: #e8e8e8;">External links</th></tr><tr><th scope="row" class="infobox-label"><a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a></th><td class="infobox-data"><span class="reflink plainlinks nourlexpansion"><a rel="nofollow" class="external text" href="https://meshb.nlm.nih.gov/record/ui?ui=D004967">D004967</a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background: #e8e8e8;">Legal status</th></tr><tr><td colspan="2" class="infobox-below" style="background: #e8e8e8; text-align: center"><a href="https://www.wikidata.org/wiki/Q277954" class="extiw" title="d:Q277954">In Wikidata</a></td></tr></tbody></table> <p><b>Estrogen</b> (also spelled <b>oestrogen</b> in <a href="/wiki/British_English" title="British English">British English</a>; <a href="/wiki/American_and_British_English_spelling_differences#ae_and_oe" title="American and British English spelling differences">see spelling differences</a>) is a category of <a href="/wiki/Sex_steroid" class="mw-redirect" title="Sex steroid">sex hormone</a> responsible for the development and regulation of the <a href="/wiki/Female_reproductive_system" title="Female reproductive system">female reproductive system</a> and <a href="/wiki/Secondary_sex_characteristic" title="Secondary sex characteristic">secondary sex characteristics</a>.<sup id="cite_ref-Huether_1-0" class="reference"><a href="#cite_note-Huether-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Satoskar_2-0" class="reference"><a href="#cite_note-Satoskar-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> There are three major <a href="/wiki/Endogeny_(biology)" title="Endogeny (biology)">endogenous</a> estrogens that have estrogenic hormonal activity: <a href="/wiki/Estrone" title="Estrone">estrone</a> (E1), <a href="/wiki/Estradiol" title="Estradiol">estradiol</a> (E2), and <a href="/wiki/Estriol" title="Estriol">estriol</a> (E3).<sup id="cite_ref-Huether_1-1" class="reference"><a href="#cite_note-Huether-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Delgado_3-0" class="reference"><a href="#cite_note-Delgado-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Estradiol, an <a href="/wiki/Estrane" title="Estrane">estrane</a>, is the most potent and prevalent.<sup id="cite_ref-Huether_1-2" class="reference"><a href="#cite_note-Huether-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Another estrogen called <a href="/wiki/Estetrol" title="Estetrol">estetrol</a> (E4) is produced only during pregnancy. </p><p>Estrogens are synthesized in all vertebrates<sup id="cite_ref-pmid7083198_4-0" class="reference"><a href="#cite_note-pmid7083198-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> and some insects.<sup id="cite_ref-Mechoulam_2005_5-0" class="reference"><a href="#cite_note-Mechoulam_2005-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Quantitatively, estrogens circulate at lower levels than <a href="/wiki/Androgen" title="Androgen">androgens</a> in both men and women.<sup id="cite_ref-Burger2002_6-0" class="reference"><a href="#cite_note-Burger2002-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> While estrogen levels are significantly lower in males than in females, estrogens nevertheless have important physiological roles in males.<sup id="cite_ref-pmid11403894_7-0" class="reference"><a href="#cite_note-pmid11403894-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>Like all <a href="/wiki/Steroid_hormone" title="Steroid hormone">steroid hormones</a>, estrogens readily <a href="/wiki/Diffusion" title="Diffusion">diffuse</a> across the <a href="/wiki/Cell_membrane" title="Cell membrane">cell membrane</a>. Once inside the cell, they bind to and activate <a href="/wiki/Estrogen_receptor" title="Estrogen receptor">estrogen receptors</a> (ERs) which in turn <a href="/wiki/Regulation_of_gene_expression" title="Regulation of gene expression">modulate</a> the <a href="/wiki/Gene_expression" title="Gene expression">expression</a> of many <a href="/wiki/Gene" title="Gene">genes</a>.<sup id="cite_ref-isbn978-1-85996-252-7_8-0" class="reference"><a href="#cite_note-isbn978-1-85996-252-7-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Additionally, estrogens bind to and activate rapid-signaling <a href="/wiki/Membrane_estrogen_receptor" title="Membrane estrogen receptor">membrane estrogen receptors</a> (mERs),<sup id="cite_ref-pmid23756388_9-0" class="reference"><a href="#cite_note-pmid23756388-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid22538318_10-0" class="reference"><a href="#cite_note-pmid22538318-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> such as <a href="/wiki/GPER" title="GPER">GPER</a> (GPR30).<sup id="cite_ref-pmid17222505_11-0" class="reference"><a href="#cite_note-pmid17222505-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>In addition to their role as natural hormones, estrogens are used as <a href="/wiki/Medication" title="Medication">medications</a>, for instance in <a href="/wiki/Menopausal_hormone_therapy" class="mw-redirect" title="Menopausal hormone therapy">menopausal hormone therapy</a>, <a href="/wiki/Hormonal_birth_control" class="mw-redirect" title="Hormonal birth control">hormonal birth control</a> and <a href="/wiki/Feminizing_hormone_therapy" title="Feminizing hormone therapy">feminizing hormone therapy</a> for <a href="/wiki/Trans_woman" title="Trans woman">transgender women</a>, <a href="/wiki/Intersex" title="Intersex">intersex</a> people, and <a href="/wiki/Non-binary_gender" title="Non-binary gender">nonbinary people</a>. </p><p>Synthetic and natural estrogens have been found in the environment and are referred to as <a href="/wiki/Xenoestrogen" title="Xenoestrogen">xenoestrogens</a>. Estrogens are among the wide range of endocrine-disrupting compounds (EDCs) and can cause health issues and reproductive disfunction in both wildlife and humans.<sup id="cite_ref-Wang_2008_12-0" class="reference"><a href="#cite_note-Wang_2008-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:1_13-0" class="reference"><a href="#cite_note-:1-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </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="Types_and_examples">Types and examples</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estrogen&action=edit&section=1" title="Edit section: Types and examples"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table role="presentation" cellpadding="0" style="border-spacing:0; clear:right; float:right;"> <tbody><tr> <td><div class="thumb tright"> <div class="thumbinner" style="width:396px;"> <div style="clear: both; font-weight: bold; font-size: 106.4%; text-align: center; background-color: light-dark(aliceblue,var(--background-color-neutral)); color:var(--color-base,light-dark(#202122,#eaecf0)); margin-bottom:3px;"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul ul{display:inline}.mw-parser-output .hlist .mw-empty-li{display:none}.mw-parser-output .hlist dt::after{content:": "}.mw-parser-output .hlist dd::after,.mw-parser-output .hlist li::after{content:" · ";font-weight:bold}.mw-parser-output .hlist dd:last-child::after,.mw-parser-output .hlist dt:last-child::after,.mw-parser-output .hlist li:last-child::after{content:none}.mw-parser-output .hlist dd dd:first-child::before,.mw-parser-output .hlist dd dt:first-child::before,.mw-parser-output .hlist dd li:first-child::before,.mw-parser-output .hlist dt dd:first-child::before,.mw-parser-output .hlist dt dt:first-child::before,.mw-parser-output .hlist dt li:first-child::before,.mw-parser-output .hlist li dd:first-child::before,.mw-parser-output .hlist li dt:first-child::before,.mw-parser-output .hlist li li:first-child::before{content:" (";font-weight:normal}.mw-parser-output .hlist dd dd:last-child::after,.mw-parser-output .hlist dd dt:last-child::after,.mw-parser-output .hlist dd li:last-child::after,.mw-parser-output .hlist dt dd:last-child::after,.mw-parser-output .hlist dt dt:last-child::after,.mw-parser-output .hlist dt li:last-child::after,.mw-parser-output .hlist li dd:last-child::after,.mw-parser-output .hlist li dt:last-child::after,.mw-parser-output .hlist li li:last-child::after{content:")";font-weight:normal}.mw-parser-output .hlist ol{counter-reset:listitem}.mw-parser-output .hlist ol>li{counter-increment:listitem}.mw-parser-output .hlist ol>li::before{content:" "counter(listitem)"\a0 "}.mw-parser-output .hlist dd ol>li:first-child::before,.mw-parser-output .hlist dt ol>li:first-child::before,.mw-parser-output .hlist li ol>li:first-child::before{content:" ("counter(listitem)"\a0 "}</style><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Chemical_structures_of_major_endogenous_estrogens" title="Template:Chemical structures of major endogenous estrogens"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Chemical_structures_of_major_endogenous_estrogens" title="Template talk:Chemical structures of major endogenous estrogens"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Chemical_structures_of_major_endogenous_estrogens" title="Special:EditPage/Template:Chemical structures of major endogenous estrogens"><abbr title="Edit this template">e</abbr></a></li></ul></div> Structures of major endogenous estrogens</div> <div class="skin-invert" style="position:relative; width:394px; height:260px; overflow:hidden; border:solid #ccc 1px; background-color:white;"> <div style="left:0px; top:0px; width:394px; position:absolute"> <span typeof="mw:File"><span><img alt="Chemical structures of major endogenous estrogens" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6e/Chemical_structures_of_major_endogenous_estrogens_no_labels.png/394px-Chemical_structures_of_major_endogenous_estrogens_no_labels.png" decoding="async" width="394" height="262" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6e/Chemical_structures_of_major_endogenous_estrogens_no_labels.png/591px-Chemical_structures_of_major_endogenous_estrogens_no_labels.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6e/Chemical_structures_of_major_endogenous_estrogens_no_labels.png/788px-Chemical_structures_of_major_endogenous_estrogens_no_labels.png 2x" data-file-width="2560" data-file-height="1700" /></span></span> </div> <div style="text-align:center; font-size:14px; line-height:110%"> <div style="background-color:transparent; color:black"><div id="annotation_53x107" style="position:absolute; left:53px; top:107px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Estrone" title="Estrone">Estrone</a> (E1)</span></div> <div id="annotation_251x107" style="position:absolute; left:251px; top:107px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a> (E2)</span></div> <div id="annotation_55x235" style="position:absolute; left:55px; top:235px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Estriol" title="Estriol">Estriol</a> (E3)</span></div> <div id="annotation_253x235" style="position:absolute; left:253px; top:235px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Estetrol" title="Estetrol">Estetrol</a> (E4)</span></div></div> </div> </div> <div class="thumbcaption" style="clear:left"><div style="float:left;margin-right:0.5em"><span typeof="mw:File"><span title="The image above contains clickable links"><img alt="The image above contains clickable links" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/18px-Interactive_icon.svg.png" decoding="async" width="18" height="27" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/27px-Interactive_icon.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/36px-Interactive_icon.svg.png 2x" data-file-width="133" data-file-height="200" /></span></span></div>Note the <a href="/wiki/Hydroxyl_group" class="mw-redirect" title="Hydroxyl group">hydroxyl</a> (–OH) <a href="/wiki/Functional_group" title="Functional group">groups</a>: estrone (E1) has one, estradiol (E2) has two, estriol (E3) has three, and estetrol (E4) has four.</div> </div> </div> </td></tr></tbody></table> <p>The four major naturally occurring estrogens in women are <a href="/wiki/Estrone" title="Estrone">estrone</a> (E1), <a href="/wiki/Estradiol" title="Estradiol">estradiol</a> (E2), <a href="/wiki/Estriol" title="Estriol">estriol</a> (E3), and <a href="/wiki/Estetrol" title="Estetrol">estetrol</a> (E4). Estradiol (E2) is the predominant estrogen during reproductive years both in terms of absolute serum levels as well as in terms of estrogenic activity. During <a href="/wiki/Menopause" title="Menopause">menopause</a>, estrone is the predominant circulating estrogen and during pregnancy estriol is the predominant circulating estrogen in terms of serum levels. Given by <a href="/wiki/Subcutaneous_injection" class="mw-redirect" title="Subcutaneous injection">subcutaneous injection</a> in mice, estradiol is about 10-fold more potent than estrone and about 100-fold more potent than estriol.<sup id="cite_ref-Labhart2012_14-0" class="reference"><a href="#cite_note-Labhart2012-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Thus, estradiol is the most important estrogen in non-pregnant females who are between the <a href="/wiki/Menarche" title="Menarche">menarche</a> and menopause stages of life. However, during <a href="/wiki/Pregnancy" title="Pregnancy">pregnancy</a> this role shifts to estriol, and in postmenopausal women estrone becomes the primary form of estrogen in the body. Another type of estrogen called <a href="/wiki/Estetrol" title="Estetrol">estetrol</a> (E4) is produced only during pregnancy. All of the different forms of estrogen are synthesized from <a href="/wiki/Androgen" title="Androgen">androgens</a>, specifically <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> and <a href="/wiki/Androstenedione" title="Androstenedione">androstenedione</a>, by the <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> <a href="/wiki/Aromatase" title="Aromatase">aromatase</a>.<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. (January 2025)">citation needed</span></a></i>]</sup> </p><p>Minor endogenous estrogens, the biosyntheses of which do not involve <a href="/wiki/Aromatase" title="Aromatase">aromatase</a>, include <a href="/wiki/27-hydroxycholesterol" class="mw-redirect" title="27-hydroxycholesterol">27-hydroxycholesterol</a>, <a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">dehydroepiandrosterone</a> (DHEA), <a href="/wiki/7-oxo-DHEA" class="mw-redirect" title="7-oxo-DHEA">7-oxo-DHEA</a>, <a href="/wiki/7%CE%B1-hydroxy-DHEA" class="mw-redirect" title="7α-hydroxy-DHEA">7α-hydroxy-DHEA</a>, <a href="/wiki/16%CE%B1-hydroxy-DHEA" class="mw-redirect" title="16α-hydroxy-DHEA">16α-hydroxy-DHEA</a>, <a href="/wiki/7%CE%B2-hydroxyepiandrosterone" class="mw-redirect" title="7β-hydroxyepiandrosterone">7β-hydroxyepiandrosterone</a>, <a href="/wiki/Androstenedione" title="Androstenedione">androstenedione</a> (A4), <a href="/wiki/Androstenediol" title="Androstenediol">androstenediol</a> (A5), <a href="/wiki/3%CE%B1-androstanediol" class="mw-redirect" title="3α-androstanediol">3α-androstanediol</a>, and <a href="/wiki/3%CE%B2-androstanediol" class="mw-redirect" title="3β-androstanediol">3β-androstanediol</a>.<sup id="cite_ref-pmid23313336_15-0" class="reference"><a href="#cite_note-pmid23313336-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid23123738_16-0" class="reference"><a href="#cite_note-pmid23123738-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> Some estrogen metabolites, such as the <a href="/wiki/Catechol_estrogen" title="Catechol estrogen">catechol estrogens</a> <a href="/wiki/2-hydroxyestradiol" class="mw-redirect" title="2-hydroxyestradiol">2-hydroxyestradiol</a>, <a href="/wiki/2-hydroxyestrone" class="mw-redirect" title="2-hydroxyestrone">2-hydroxyestrone</a>, <a href="/wiki/4-hydroxyestradiol" class="mw-redirect" title="4-hydroxyestradiol">4-hydroxyestradiol</a>, and <a href="/wiki/4-hydroxyestrone" class="mw-redirect" title="4-hydroxyestrone">4-hydroxyestrone</a>, as well as <a href="/wiki/16%CE%B1-hydroxyestrone" class="mw-redirect" title="16α-hydroxyestrone">16α-hydroxyestrone</a>, are also estrogens with varying degrees of activity.<sup id="cite_ref-pmid10865186_17-0" class="reference"><a href="#cite_note-pmid10865186-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> The biological importance of these minor estrogens is not entirely clear. </p> <div class="mw-heading mw-heading2"><h2 id="Biological_function">Biological function</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estrogen&action=edit&section=2" title="Edit section: Biological function"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Estradiol_during_menstrual_cycle.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Estradiol_during_menstrual_cycle.png/350px-Estradiol_during_menstrual_cycle.png" decoding="async" width="350" height="156" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Estradiol_during_menstrual_cycle.png/525px-Estradiol_during_menstrual_cycle.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Estradiol_during_menstrual_cycle.png/700px-Estradiol_during_menstrual_cycle.png 2x" data-file-width="3682" data-file-height="1640" /></a><figcaption><a href="/wiki/Reference_ranges_for_blood_tests" title="Reference ranges for blood tests">Reference ranges for the blood content</a> of estradiol, the primary type of estrogen, during the <a href="/wiki/Menstrual_cycle" title="Menstrual cycle">menstrual cycle</a><sup id="cite_ref-Häggström2014_18-0" class="reference"><a href="#cite_note-Häggström2014-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup></figcaption></figure> <p>The actions of estrogen are mediated by the <a href="/wiki/Estrogen_receptor" title="Estrogen receptor">estrogen receptor</a> (ER), a dimeric nuclear protein that binds to DNA and controls <a href="/wiki/Gene_expression" title="Gene expression">gene expression</a>. Like other steroid hormones, estrogen enters passively into the cell where it binds to and activates the estrogen receptor. The estrogen:ER complex binds to specific DNA sequences called a <a href="/wiki/Hormone_response_element" class="mw-redirect" title="Hormone response element">hormone response element</a> to activate the transcription of target genes (in a study using an estrogen-dependent breast cancer cell line as model, 89 such genes were identified).<sup id="cite_ref-pmid15345050_19-0" class="reference"><a href="#cite_note-pmid15345050-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> Since estrogen enters all cells, its actions are dependent on the presence of the ER in the cell. The ER is expressed in specific tissues including the ovary, uterus and breast. The metabolic effects of estrogen in postmenopausal women have been linked to the genetic polymorphism of the ER.<sup id="cite_ref-pmid21117950_20-0" class="reference"><a href="#cite_note-pmid21117950-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p><p>While estrogens are present in both <a href="/wiki/Man" title="Man">men</a> and <a href="/wiki/Woman" title="Woman">women</a>, they are usually present at significantly higher levels in women of reproductive age. They promote the development of female <a href="/wiki/Secondary_sexual_characteristic" class="mw-redirect" title="Secondary sexual characteristic">secondary sexual characteristics</a>, such as <a href="/wiki/Breasts" class="mw-redirect" title="Breasts">breasts</a>, darkening and enlargement of <a href="/wiki/Nipples" class="mw-redirect" title="Nipples">nipples</a>,<sup id="cite_ref-Lauwers_Shinskie_2004_p._93_21-0" class="reference"><a href="#cite_note-Lauwers_Shinskie_2004_p._93-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> and thickening of the <a href="/wiki/Endometrium" title="Endometrium">endometrium</a> and other aspects of regulating the menstrual cycle. In males, estrogen regulates certain functions of the <a href="/wiki/Reproductive_system" title="Reproductive system">reproductive system</a> important to the maturation of <a href="/wiki/Sperm" title="Sperm">sperm</a><sup id="cite_ref-titleScience_News_Online_(12/6/97):_Estrogens_Emerging_Manly_Alter_Ego_22-0" class="reference"><a href="#cite_note-titleScience_News_Online_(12/6/97):_Estrogens_Emerging_Manly_Alter_Ego-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid9393999_23-0" class="reference"><a href="#cite_note-pmid9393999-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Science_Blog_24-0" class="reference"><a href="#cite_note-Science_Blog-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> and may be necessary for a healthy <a href="/wiki/Libido" title="Libido">libido</a>.<sup id="cite_ref-pmid15555924_25-0" class="reference"><a href="#cite_note-pmid15555924-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable sortable mw-collapsible mw-collapsed" style="font-size: small; text-align:left; margin-left:auto; margin-right:auto; border:none;"> <caption class="nowrap"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Affinities_of_estrogen_receptor_ligands_for_the_ER%CE%B1_and_ER%CE%B2" title="Template:Affinities of estrogen receptor ligands for the ERα and ERβ"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Affinities_of_estrogen_receptor_ligands_for_the_ER%CE%B1_and_ER%CE%B2" title="Template talk:Affinities of estrogen receptor ligands for the ERα and ERβ"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Affinities_of_estrogen_receptor_ligands_for_the_ER%CE%B1_and_ER%CE%B2" title="Special:EditPage/Template:Affinities of estrogen receptor ligands for the ERα and ERβ"><abbr title="Edit this template">e</abbr></a></li></ul></div> <span style="font-size:104%;">Affinities of estrogen receptor ligands for the ERα and ERβ</span> </caption> <tbody><tr> <th rowspan="2"><a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">Ligand</a></th> <th rowspan="2" class="unsortable">Other names</th> <th colspan="2"><a href="/wiki/Relative_binding_affinity" class="mw-redirect" title="Relative binding affinity">Relative binding affinities</a> (RBA, %)<sup>a</sup></th> <th colspan="2"><a href="/wiki/Absolute_binding_affinity" class="mw-redirect" title="Absolute binding affinity">Absolute binding affinities</a> (K<sub>i</sub>, nM)<sup>a</sup></th> <th rowspan="2">Action </th></tr> <tr> <th><a href="/wiki/ER%CE%B1" class="mw-redirect" title="ERα">ERα</a></th> <th><a href="/wiki/ER%CE%B2" class="mw-redirect" title="ERβ">ERβ</a></th> <th><a href="/wiki/ER%CE%B1" class="mw-redirect" title="ERα">ERα</a></th> <th><a href="/wiki/ER%CE%B2" class="mw-redirect" title="ERβ">ERβ</a> </th></tr> <tr> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a></td> <td>E2; 17β-Estradiol</td> <td>100</td> <td>100</td> <td>0.115 (0.04–0.24)</td> <td>0.15 (0.10–2.08)</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Estrone_(medication)" title="Estrone (medication)">Estrone</a></td> <td>E1; 17-Ketoestradiol</td> <td>16.39 (0.7–60)</td> <td>6.5 (1.36–52)</td> <td>0.445 (0.3–1.01)</td> <td>1.75 (0.35–9.24)</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Estriol_(medication)" title="Estriol (medication)">Estriol</a></td> <td>E3; 16α-OH-17β-E2</td> <td>12.65 (4.03–56)</td> <td>26 (14.0–44.6)</td> <td>0.45 (0.35–1.4)</td> <td>0.7 (0.63–0.7)</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Estetrol_(medication)" title="Estetrol (medication)">Estetrol</a></td> <td>E4; 15α,16α-Di-OH-17β-E2</td> <td>4.0</td> <td>3.0</td> <td>4.9</td> <td>19</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Alfatradiol" title="Alfatradiol">Alfatradiol</a></td> <td>17α-Estradiol</td> <td>20.5 (7–80.1)</td> <td>8.195 (2–42)</td> <td>0.2–0.52</td> <td>0.43–1.2</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/16-Epiestriol" class="mw-redirect" title="16-Epiestriol">16-Epiestriol</a></td> <td>16β-Hydroxy-17β-estradiol</td> <td>7.795 (4.94–63)</td> <td>50</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/17-Epiestriol" class="mw-redirect" title="17-Epiestriol">17-Epiestriol</a></td> <td>16α-Hydroxy-17α-estradiol</td> <td>55.45 (29–103)</td> <td>79–80</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/16,17-Epiestriol" class="mw-redirect" title="16,17-Epiestriol">16,17-Epiestriol</a></td> <td>16β-Hydroxy-17α-estradiol</td> <td>1.0</td> <td>13</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/2-Hydroxyestradiol" title="2-Hydroxyestradiol">2-Hydroxyestradiol</a></td> <td>2-OH-E2</td> <td>22 (7–81)</td> <td>11–35</td> <td>2.5</td> <td>1.3</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/2-Methoxyestradiol" title="2-Methoxyestradiol">2-Methoxyestradiol</a></td> <td>2-MeO-E2</td> <td>0.0027–2.0</td> <td>1.0</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/4-Hydroxyestradiol" title="4-Hydroxyestradiol">4-Hydroxyestradiol</a></td> <td>4-OH-E2</td> <td>13 (8–70)</td> <td>7–56</td> <td>1.0</td> <td>1.9</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/4-Methoxyestradiol" title="4-Methoxyestradiol">4-Methoxyestradiol</a></td> <td>4-MeO-E2</td> <td>2.0</td> <td>1.0</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/2-Hydroxyestrone" title="2-Hydroxyestrone">2-Hydroxyestrone</a></td> <td>2-OH-E1</td> <td>2.0–4.0</td> <td>0.2–0.4</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/2-Methoxyestrone" title="2-Methoxyestrone">2-Methoxyestrone</a></td> <td>2-MeO-E1</td> <td><0.001–<1</td> <td><1</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/4-Hydroxyestrone" title="4-Hydroxyestrone">4-Hydroxyestrone</a></td> <td>4-OH-E1</td> <td>1.0–2.0</td> <td>1.0</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/4-Methoxyestrone" title="4-Methoxyestrone">4-Methoxyestrone</a></td> <td>4-MeO-E1</td> <td><1</td> <td><1</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/16%CE%B1-Hydroxyestrone" title="16α-Hydroxyestrone">16α-Hydroxyestrone</a></td> <td>16α-OH-E1; 17-Ketoestriol</td> <td>2.0–6.5</td> <td>35</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/2-Hydroxyestriol" title="2-Hydroxyestriol">2-Hydroxyestriol</a></td> <td>2-OH-E3</td> <td>2.0</td> <td>1.0</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/4-Methoxyestriol" title="4-Methoxyestriol">4-Methoxyestriol</a></td> <td>4-MeO-E3</td> <td>1.0</td> <td>1.0</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/Estradiol_sulfate" title="Estradiol sulfate">Estradiol sulfate</a></td> <td>E2S; Estradiol 3-sulfate</td> <td><1</td> <td><1</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/Estradiol_disulfate" title="Estradiol disulfate">Estradiol disulfate</a></td> <td>Estradiol 3,17β-disulfate</td> <td>0.0004</td> <td>?</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/Estradiol_3-glucuronide" title="Estradiol 3-glucuronide">Estradiol 3-glucuronide</a></td> <td>E2-3G</td> <td>0.0079</td> <td>?</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/Estradiol_17%CE%B2-glucuronide" class="mw-redirect" title="Estradiol 17β-glucuronide">Estradiol 17β-glucuronide</a></td> <td>E2-17G</td> <td>0.0015</td> <td>?</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/Estradiol_3-glucuronide_17%CE%B2-sulfate" title="Estradiol 3-glucuronide 17β-sulfate">Estradiol 3-gluc. 17β-sulfate</a></td> <td>E2-3G-17S</td> <td>0.0001</td> <td>?</td> <td>?</td> <td>?</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/Estrone_sulfate_(medication)" title="Estrone sulfate (medication)">Estrone sulfate</a></td> <td>E1S; Estrone 3-sulfate</td> <td><1</td> <td><1</td> <td>>10</td> <td>>10</td> <td>Metabolite </td></tr> <tr> <td><a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">Estradiol benzoate</a></td> <td>EB; Estradiol 3-benzoate</td> <td>10</td> <td>?</td> <td>?</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Estradiol_17%CE%B2-benzoate" title="Estradiol 17β-benzoate">Estradiol 17β-benzoate</a></td> <td>E2-17B</td> <td>11.3</td> <td>32.6</td> <td>?</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Estrone_methyl_ether" title="Estrone methyl ether">Estrone methyl ether</a></td> <td>Estrone 3-methyl ether</td> <td>0.145</td> <td>?</td> <td>?</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Ent-Estradiol" title="Ent-Estradiol"><i>ent</i>-Estradiol</a></td> <td>1-Estradiol</td> <td>1.31–12.34</td> <td>9.44–80.07</td> <td>?</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Equilin" title="Equilin">Equilin</a></td> <td>7-Dehydroestrone</td> <td>13 (4.0–28.9)</td> <td>13.0–49</td> <td>0.79</td> <td>0.36</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Equilenin" title="Equilenin">Equilenin</a></td> <td>6,8-Didehydroestrone</td> <td>2.0–15</td> <td>7.0–20</td> <td>0.64</td> <td>0.62</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/17%CE%B2-Dihydroequilin" title="17β-Dihydroequilin">17β-Dihydroequilin</a></td> <td>7-Dehydro-17β-estradiol</td> <td>7.9–113</td> <td>7.9–108</td> <td>0.09</td> <td>0.17</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/17%CE%B1-Dihydroequilin" title="17α-Dihydroequilin">17α-Dihydroequilin</a></td> <td>7-Dehydro-17α-estradiol</td> <td>18.6 (18–41)</td> <td>14–32</td> <td>0.24</td> <td>0.57</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/17%CE%B2-Dihydroequilenin" title="17β-Dihydroequilenin">17β-Dihydroequilenin</a></td> <td>6,8-Didehydro-17β-estradiol</td> <td>35–68</td> <td>90–100</td> <td>0.15</td> <td>0.20</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/17%CE%B1-Dihydroequilenin" title="17α-Dihydroequilenin">17α-Dihydroequilenin</a></td> <td>6,8-Didehydro-17α-estradiol</td> <td>20</td> <td>49</td> <td>0.50</td> <td>0.37</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/8,9-Dehydroestradiol" title="8,9-Dehydroestradiol">Δ<sup>8</sup>-Estradiol</a></td> <td>8,9-Dehydro-17β-estradiol</td> <td>68</td> <td>72</td> <td>0.15</td> <td>0.25</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/8,9-Dehydroestrone" title="8,9-Dehydroestrone">Δ<sup>8</sup>-Estrone</a></td> <td>8,9-Dehydroestrone</td> <td>19</td> <td>32</td> <td>0.52</td> <td>0.57</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a></td> <td>EE; 17α-Ethynyl-17β-E2</td> <td>120.9 (68.8–480)</td> <td>44.4 (2.0–144)</td> <td>0.02–0.05</td> <td>0.29–0.81</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Mestranol" title="Mestranol">Mestranol</a></td> <td>EE 3-methyl ether</td> <td>?</td> <td>2.5</td> <td>?</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Moxestrol" title="Moxestrol">Moxestrol</a></td> <td>RU-2858; 11β-Methoxy-EE</td> <td>35–43</td> <td>5–20</td> <td>0.5</td> <td>2.6</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Methylestradiol" title="Methylestradiol">Methylestradiol</a></td> <td>17α-Methyl-17β-estradiol</td> <td>70</td> <td>44</td> <td>?</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a></td> <td>DES; Stilbestrol</td> <td>129.5 (89.1–468)</td> <td>219.63 (61.2–295)</td> <td>0.04</td> <td>0.05</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Hexestrol" title="Hexestrol">Hexestrol</a></td> <td>Dihydrodiethylstilbestrol</td> <td>153.6 (31–302)</td> <td>60–234</td> <td>0.06</td> <td>0.06</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Dienestrol" title="Dienestrol">Dienestrol</a></td> <td>Dehydrostilbestrol</td> <td>37 (20.4–223)</td> <td>56–404</td> <td>0.05</td> <td>0.03</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Benzestrol" title="Benzestrol">Benzestrol (B2)</a></td> <td>–</td> <td>114</td> <td>?</td> <td>?</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Chlorotrianisene" title="Chlorotrianisene">Chlorotrianisene</a></td> <td>TACE</td> <td>1.74</td> <td>?</td> <td>15.30</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Triphenylethylene" title="Triphenylethylene">Triphenylethylene</a></td> <td>TPE</td> <td>0.074</td> <td>?</td> <td>?</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Triphenylbromoethylene" title="Triphenylbromoethylene">Triphenylbromoethylene</a></td> <td>TPBE</td> <td>2.69</td> <td>?</td> <td>?</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a></td> <td>ICI-46,474</td> <td>3 (0.1–47)</td> <td>3.33 (0.28–6)</td> <td>3.4–9.69</td> <td>2.5</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Afimoxifene" title="Afimoxifene">Afimoxifene</a></td> <td>4-Hydroxytamoxifen; 4-OHT</td> <td>100.1 (1.7–257)</td> <td>10 (0.98–339)</td> <td>2.3 (0.1–3.61)</td> <td>0.04–4.8</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Toremifene" title="Toremifene">Toremifene</a></td> <td>4-Chlorotamoxifen; 4-CT</td> <td>?</td> <td>?</td> <td>7.14–20.3</td> <td>15.4</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Clomifene" title="Clomifene">Clomifene</a></td> <td>MRL-41</td> <td>25 (19.2–37.2)</td> <td>12</td> <td>0.9</td> <td>1.2</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Cyclofenil" title="Cyclofenil">Cyclofenil</a></td> <td>F-6066; Sexovid</td> <td>151–152</td> <td>243</td> <td>?</td> <td>?</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Nafoxidine" title="Nafoxidine">Nafoxidine</a></td> <td>U-11,000A</td> <td>30.9–44</td> <td>16</td> <td>0.3</td> <td>0.8</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></td> <td>–</td> <td>41.2 (7.8–69)</td> <td>5.34 (0.54–16)</td> <td>0.188–0.52</td> <td>20.2</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Arzoxifene" title="Arzoxifene">Arzoxifene</a></td> <td>LY-353,381</td> <td>?</td> <td>?</td> <td>0.179</td> <td>?</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Lasofoxifene" title="Lasofoxifene">Lasofoxifene</a></td> <td>CP-336,156</td> <td>10.2–166</td> <td>19.0</td> <td>0.229</td> <td>?</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Ormeloxifene" title="Ormeloxifene">Ormeloxifene</a></td> <td>Centchroman</td> <td>?</td> <td>?</td> <td>0.313</td> <td>?</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Levormeloxifene" title="Levormeloxifene">Levormeloxifene</a></td> <td>6720-CDRI; NNC-460,020</td> <td>1.55</td> <td>1.88</td> <td>?</td> <td>?</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Ospemifene" title="Ospemifene">Ospemifene</a></td> <td>Deaminohydroxytoremifene</td> <td>0.82–2.63</td> <td>0.59–1.22</td> <td>?</td> <td>?</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Bazedoxifene" title="Bazedoxifene">Bazedoxifene</a></td> <td>–</td> <td>?</td> <td>?</td> <td>0.053</td> <td>?</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/Etacstil" title="Etacstil">Etacstil</a></td> <td>GW-5638</td> <td>4.30</td> <td>11.5</td> <td>?</td> <td>?</td> <td>SERM </td></tr> <tr> <td><a href="/wiki/ICI-164,384" class="mw-redirect" title="ICI-164,384">ICI-164,384</a></td> <td>–</td> <td>63.5 (3.70–97.7)</td> <td>166</td> <td>0.2</td> <td>0.08</td> <td>Antiestrogen </td></tr> <tr> <td><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant</a></td> <td>ICI-182,780</td> <td>43.5 (9.4–325)</td> <td>21.65 (2.05–40.5)</td> <td>0.42</td> <td>1.3</td> <td>Antiestrogen </td></tr> <tr> <td><a href="/wiki/Propylpyrazoletriol" title="Propylpyrazoletriol">Propylpyrazoletriol</a></td> <td>PPT</td> <td>49 (10.0–89.1)</td> <td>0.12</td> <td>0.40</td> <td>92.8</td> <td>ERα agonist </td></tr> <tr> <td><a href="/wiki/16%CE%B1-LE2" title="16α-LE2">16α-LE2</a></td> <td>16α-Lactone-17β-estradiol</td> <td>14.6–57</td> <td>0.089</td> <td>0.27</td> <td>131</td> <td>ERα agonist </td></tr> <tr> <td><a href="/wiki/16%CE%B1-Iodo-E2" title="16α-Iodo-E2">16α-Iodo-E2</a></td> <td>16α-Iodo-17β-estradiol</td> <td>30.2</td> <td>2.30</td> <td>?</td> <td>?</td> <td>ERα agonist </td></tr> <tr> <td><a href="/wiki/Methylpiperidinopyrazole" title="Methylpiperidinopyrazole">Methylpiperidinopyrazole</a></td> <td>MPP</td> <td>11</td> <td>0.05</td> <td>?</td> <td>?</td> <td>ERα antagonist </td></tr> <tr> <td><a href="/wiki/Diarylpropionitrile" title="Diarylpropionitrile">Diarylpropionitrile</a></td> <td>DPN</td> <td>0.12–0.25</td> <td>6.6–18</td> <td>32.4</td> <td>1.7</td> <td>ERβ agonist </td></tr> <tr> <td><a href="/wiki/8%CE%B2-VE2" title="8β-VE2">8β-VE2</a></td> <td>8β-Vinyl-17β-estradiol</td> <td>0.35</td> <td>22.0–83</td> <td>12.9</td> <td>0.50</td> <td>ERβ agonist </td></tr> <tr> <td><a href="/wiki/Prinaberel" title="Prinaberel">Prinaberel</a></td> <td>ERB-041; WAY-202,041</td> <td>0.27</td> <td>67–72</td> <td>?</td> <td>?</td> <td>ERβ agonist </td></tr> <tr> <td><a href="/wiki/ERB-196" title="ERB-196">ERB-196</a></td> <td>WAY-202,196</td> <td>?</td> <td>180</td> <td>?</td> <td>?</td> <td>ERβ agonist </td></tr> <tr> <td><a href="/wiki/Erteberel" title="Erteberel">Erteberel</a></td> <td>SERBA-1; LY-500,307</td> <td>?</td> <td>?</td> <td>2.68</td> <td>0.19</td> <td>ERβ agonist </td></tr> <tr> <td><a href="/wiki/SERBA-2" title="SERBA-2">SERBA-2</a></td> <td>–</td> <td>?</td> <td>?</td> <td>14.5</td> <td>1.54</td> <td>ERβ agonist </td></tr> <tr> <td><a href="/wiki/Coumestrol" title="Coumestrol">Coumestrol</a></td> <td>–</td> <td>9.225 (0.0117–94)</td> <td>64.125 (0.41–185)</td> <td>0.14–80.0</td> <td>0.07–27.0</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Genistein" title="Genistein">Genistein</a></td> <td>–</td> <td>0.445 (0.0012–16)</td> <td>33.42 (0.86–87)</td> <td>2.6–126</td> <td>0.3–12.8</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Equol" title="Equol">Equol</a></td> <td>–</td> <td>0.2–0.287</td> <td>0.85 (0.10–2.85)</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Daidzein" title="Daidzein">Daidzein</a></td> <td>–</td> <td>0.07 (0.0018–9.3)</td> <td>0.7865 (0.04–17.1)</td> <td>2.0</td> <td>85.3</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Biochanin_A" title="Biochanin A">Biochanin A</a></td> <td>–</td> <td>0.04 (0.022–0.15)</td> <td>0.6225 (0.010–1.2)</td> <td>174</td> <td>8.9</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Kaempferol" title="Kaempferol">Kaempferol</a></td> <td>–</td> <td>0.07 (0.029–0.10)</td> <td>2.2 (0.002–3.00)</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Naringenin" title="Naringenin">Naringenin</a></td> <td>–</td> <td>0.0054 (<0.001–0.01)</td> <td>0.15 (0.11–0.33)</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/8-Prenylnaringenin" title="8-Prenylnaringenin">8-Prenylnaringenin</a></td> <td>8-PN</td> <td>4.4</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Quercetin" title="Quercetin">Quercetin</a></td> <td>–</td> <td><0.001–0.01</td> <td>0.002–0.040</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Ipriflavone" title="Ipriflavone">Ipriflavone</a></td> <td>–</td> <td><0.01</td> <td><0.01</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Miroestrol" title="Miroestrol">Miroestrol</a></td> <td>–</td> <td>0.39</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Deoxymiroestrol" class="mw-redirect" title="Deoxymiroestrol">Deoxymiroestrol</a></td> <td>–</td> <td>2.0</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/%CE%92-Sitosterol" title="Β-Sitosterol">β-Sitosterol</a></td> <td>–</td> <td><0.001–0.0875</td> <td><0.001–0.016</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Resveratrol" title="Resveratrol">Resveratrol</a></td> <td>–</td> <td><0.001–0.0032</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/%CE%91-Zearalenol" title="Α-Zearalenol">α-Zearalenol</a></td> <td>–</td> <td>48 (13–52.5)</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/%CE%92-Zearalenol" title="Β-Zearalenol">β-Zearalenol</a></td> <td>–</td> <td>0.6 (0.032–13)</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Zeranol" title="Zeranol">Zeranol</a></td> <td>α-Zearalanol</td> <td>48–111</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Taleranol" title="Taleranol">Taleranol</a></td> <td>β-Zearalanol</td> <td>16 (13–17.8)</td> <td>14</td> <td>0.8</td> <td>0.9</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Zearalenone" title="Zearalenone">Zearalenone</a></td> <td>ZEN</td> <td>7.68 (2.04–28)</td> <td>9.45 (2.43–31.5)</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Zearalanone" title="Zearalanone">Zearalanone</a></td> <td>ZAN</td> <td>0.51</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Bisphenol_A" title="Bisphenol A">Bisphenol A</a></td> <td>BPA</td> <td>0.0315 (0.008–1.0)</td> <td>0.135 (0.002–4.23)</td> <td>195</td> <td>35</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Endosulfan" title="Endosulfan">Endosulfan</a></td> <td>EDS</td> <td><0.001–<0.01</td> <td><0.01</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Kepone" class="mw-redirect" title="Kepone">Kepone</a></td> <td>Chlordecone</td> <td>0.0069–0.2</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/O,p%27-DDT" class="mw-redirect" title="O,p'-DDT"><i>o,p'</i>-DDT</a></td> <td>–</td> <td>0.0073–0.4</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/P,p%27-DDT" class="mw-redirect" title="P,p'-DDT"><i>p,p'</i>-DDT</a></td> <td>–</td> <td>0.03</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Methoxychlor" title="Methoxychlor">Methoxychlor</a></td> <td><i>p,p'</i>-Dimethoxy-DDT</td> <td>0.01 (<0.001–0.02)</td> <td>0.01–0.13</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/HPTE" title="HPTE">HPTE</a></td> <td>Hydroxychlor; <i>p,p'</i>-OH-DDT</td> <td>1.2–1.7</td> <td>?</td> <td>?</td> <td>?</td> <td>Xenoestrogen </td></tr> <tr> <td><a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">Testosterone</a></td> <td>T; 4-Androstenolone</td> <td><0.0001–<0.01</td> <td><0.002–0.040</td> <td>>5000</td> <td>>5000</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/Androstanolone" title="Androstanolone">Dihydrotestosterone</a></td> <td>DHT; 5α-Androstanolone</td> <td>0.01 (<0.001–0.05)</td> <td>0.0059–0.17</td> <td>221–>5000</td> <td>73–1688</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/Nandrolone" title="Nandrolone">Nandrolone</a></td> <td>19-Nortestosterone; 19-NT</td> <td>0.01</td> <td>0.23</td> <td>765</td> <td>53</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/Prasterone" title="Prasterone">Dehydroepiandrosterone</a></td> <td>DHEA; Prasterone</td> <td>0.038 (<0.001–0.04)</td> <td>0.019–0.07</td> <td>245–1053</td> <td>163–515</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/5-Androstenediol" class="mw-redirect" title="5-Androstenediol">5-Androstenediol</a></td> <td>A5; Androstenediol</td> <td>6</td> <td>17</td> <td>3.6</td> <td>0.9</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/4-Androstenediol" title="4-Androstenediol">4-Androstenediol</a></td> <td>–</td> <td>0.5</td> <td>0.6</td> <td>23</td> <td>19</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/4-Androstenedione" class="mw-redirect" title="4-Androstenedione">4-Androstenedione</a></td> <td>A4; Androstenedione</td> <td><0.01</td> <td><0.01</td> <td>>10000</td> <td>>10000</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></td> <td>3α-Adiol</td> <td>0.07</td> <td>0.3</td> <td>260</td> <td>48</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/3%CE%B2-Androstanediol" title="3β-Androstanediol">3β-Androstanediol</a></td> <td>3β-Adiol</td> <td>3</td> <td>7</td> <td>6</td> <td>2</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/Androstanedione" title="Androstanedione">Androstanedione</a></td> <td>5α-Androstanedione</td> <td><0.01</td> <td><0.01</td> <td>>10000</td> <td>>10000</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/Etiocholanedione" title="Etiocholanedione">Etiocholanedione</a></td> <td>5β-Androstanedione</td> <td><0.01</td> <td><0.01</td> <td>>10000</td> <td>>10000</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/Methyltestosterone" title="Methyltestosterone">Methyltestosterone</a></td> <td>17α-Methyltestosterone</td> <td><0.0001</td> <td>?</td> <td>?</td> <td>?</td> <td>Androgen </td></tr> <tr> <td><a href="/wiki/Ethinyl-3%CE%B1-androstanediol" class="mw-redirect" title="Ethinyl-3α-androstanediol">Ethinyl-3α-androstanediol</a></td> <td>17α-Ethynyl-3α-adiol</td> <td>4.0</td> <td><0.07</td> <td>?</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Ethinyl-3%CE%B2-androstanediol" class="mw-redirect" title="Ethinyl-3β-androstanediol">Ethinyl-3β-androstanediol</a></td> <td>17α-Ethynyl-3β-adiol</td> <td>50</td> <td>5.6</td> <td>?</td> <td>?</td> <td>Estrogen </td></tr> <tr> <td><a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">Progesterone</a></td> <td>P4; 4-Pregnenedione</td> <td><0.001–0.6</td> <td><0.001–0.010</td> <td>?</td> <td>?</td> <td>Progestogen </td></tr> <tr> <td><a href="/wiki/Norethisterone" title="Norethisterone">Norethisterone</a></td> <td>NET; 17α-Ethynyl-19-NT</td> <td>0.085 (0.0015–<0.1)</td> <td>0.1 (0.01–0.3)</td> <td>152</td> <td>1084</td> <td>Progestogen </td></tr> <tr> <td><a href="/wiki/Norethynodrel" class="mw-redirect" title="Norethynodrel">Norethynodrel</a></td> <td>5(10)-Norethisterone</td> <td>0.5 (0.3–0.7)</td> <td><0.1–0.22</td> <td>14</td> <td>53</td> <td>Progestogen </td></tr> <tr> <td><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></td> <td>7α-Methylnorethynodrel</td> <td>0.5 (0.45–2.0)</td> <td>0.2–0.076</td> <td>?</td> <td>?</td> <td>Progestogen </td></tr> <tr> <td><a href="/wiki/%CE%944-Tibolone" title="Δ4-Tibolone">Δ<sup>4</sup>-Tibolone</a></td> <td>7α-Methylnorethisterone</td> <td>0.069–<0.1</td> <td>0.027–<0.1</td> <td>?</td> <td>?</td> <td>Progestogen </td></tr> <tr> <td><a href="/wiki/3%CE%B1-Hydroxytibolone" title="3α-Hydroxytibolone">3α-Hydroxytibolone</a></td> <td>–</td> <td>2.5 (1.06–5.0)</td> <td>0.6–0.8</td> <td>?</td> <td>?</td> <td>Progestogen </td></tr> <tr> <td><a href="/wiki/3%CE%B2-Hydroxytibolone" title="3β-Hydroxytibolone">3β-Hydroxytibolone</a></td> <td>–</td> <td>1.6 (0.75–1.9)</td> <td>0.070–0.1</td> <td>?</td> <td>?</td> <td>Progestogen </td></tr> <tr class="sortbottom skin-invert"> <td colspan="7" style="width: 1px; background-color:#eaecf0; text-align: center;"><b>Footnotes:</b> <sup>a</sup> = (1) <a href="/wiki/Binding_affinity" class="mw-redirect" title="Binding affinity">Binding affinity</a> values are of the format "median (range)" (# (#–#)), "range" (#–#), or "value" (#) depending on the values available. The full sets of values within the ranges can be found in the Wiki code. (2) Binding affinities were determined via displacement studies in a variety of <i><a href="/wiki/In-vitro" class="mw-redirect" title="In-vitro">in-vitro</a></i> systems with <a href="/wiki/Radiolabel" class="mw-redirect" title="Radiolabel">labeled</a> estradiol and human <a href="/wiki/ER%CE%B1" class="mw-redirect" title="ERα">ERα</a> and <a href="/wiki/ER%CE%B2" class="mw-redirect" title="ERβ">ERβ</a> proteins (except the ERβ values from Kuiper et al. (1997), which are rat ERβ). <b>Sources:</b> See template page. </td></tr></tbody></table> <table class="wikitable sortable mw-collapsible mw-collapsed" style="text-align:left; margin-left:auto; margin-right:auto; border:none;"> <caption class="nowrap"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Relative_affinities_of_estrogens_for_steroid_hormone_receptors_and_blood_proteins" title="Template:Relative affinities of estrogens for steroid hormone receptors and blood proteins"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Relative_affinities_of_estrogens_for_steroid_hormone_receptors_and_blood_proteins" title="Template talk:Relative affinities of estrogens for steroid hormone receptors and blood proteins"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Relative_affinities_of_estrogens_for_steroid_hormone_receptors_and_blood_proteins" title="Special:EditPage/Template:Relative affinities of estrogens for steroid hormone receptors and blood proteins"><abbr title="Edit this template">e</abbr></a></li></ul></div> Relative affinities of estrogens for steroid hormone receptors and blood proteins </caption> <tbody><tr> <th rowspan="2"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogen</a></th> <th colspan="7"><a href="/wiki/Relative_binding_affinity" class="mw-redirect" title="Relative binding affinity">Relative binding affinities</a> (%) </th></tr> <tr> <th><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor</span></th> <th><a href="/wiki/Androgen_receptor" title="Androgen receptor"><abbr title="Androgen receptor">AR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Androgen receptor</span></th> <th><a href="/wiki/Progesterone_receptor" title="Progesterone receptor"><abbr title="Progesterone receptor">PR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Progesterone receptor</span></th> <th><a href="/wiki/Glucocorticoid_receptor" title="Glucocorticoid receptor"><abbr title="Glucocorticoid receptor">GR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Glucocorticoid receptor</span></th> <th><a href="/wiki/Mineralocorticoid_receptor" title="Mineralocorticoid receptor"><abbr title="Mineralocorticoid receptor">MR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Mineralocorticoid receptor</span></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/Corticosteroid_binding_globulin" class="mw-redirect" title="Corticosteroid binding globulin"><abbr title="Corticosteroid binding globulin">CBG</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Corticosteroid binding globulin</span> </th></tr> <tr> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a></td> <td>100</td> <td>7.9</td> <td>2.6</td> <td>0.6</td> <td>0.13</td> <td>8.7–12</td> <td><0.1 </td></tr> <tr> <td><a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">Estradiol benzoate</a></td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td><0.1–0.16</td> <td><0.1 </td></tr> <tr> <td><a href="/wiki/Estradiol_valerate" title="Estradiol valerate">Estradiol valerate</a></td> <td>2</td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>? </td></tr> <tr> <td><a href="/wiki/Estrone_(medication)" title="Estrone (medication)">Estrone</a></td> <td>11–35</td> <td><1</td> <td><1</td> <td><1</td> <td><1</td> <td>2.7</td> <td><0.1 </td></tr> <tr> <td><a href="/wiki/Estrone_sulfate_(medication)" title="Estrone sulfate (medication)">Estrone sulfate</a></td> <td>2</td> <td>2</td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>? </td></tr> <tr> <td><a href="/wiki/Estriol_(medication)" title="Estriol (medication)">Estriol</a></td> <td>10–15</td> <td><1</td> <td><1</td> <td><1</td> <td><1</td> <td><0.1</td> <td><0.1 </td></tr> <tr> <td><a href="/wiki/Equilin" title="Equilin">Equilin</a></td> <td>40</td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>0 </td></tr> <tr> <td><a href="/wiki/Alfatradiol" title="Alfatradiol">Alfatradiol</a></td> <td>15</td> <td><1</td> <td><1</td> <td><1</td> <td><1</td> <td>?</td> <td>? </td></tr> <tr> <td><a href="/wiki/Epiestriol" title="Epiestriol">Epiestriol</a></td> <td>20</td> <td><1</td> <td><1</td> <td><1</td> <td><1</td> <td>?</td> <td>? </td></tr> <tr> <td><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a></td> <td>100–112</td> <td>1–3</td> <td>15–25</td> <td>1–3</td> <td><1</td> <td>0.18</td> <td><0.1 </td></tr> <tr> <td><a href="/wiki/Mestranol" title="Mestranol">Mestranol</a></td> <td>1</td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td><0.1</td> <td><0.1 </td></tr> <tr> <td><a href="/wiki/Methylestradiol" title="Methylestradiol">Methylestradiol</a></td> <td>67</td> <td>1–3</td> <td>3–25</td> <td>1–3</td> <td><1</td> <td>?</td> <td>? </td></tr> <tr> <td><a href="/wiki/Moxestrol" title="Moxestrol">Moxestrol</a></td> <td>12</td> <td><0.1</td> <td>0.8</td> <td>3.2</td> <td><0.1</td> <td><0.2</td> <td><0.1 </td></tr> <tr> <td><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a></td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td><0.1</td> <td><0.1 </td></tr> <tr class="sortbottom"> <td colspan="8" style="width: 1px; background-color:#eaecf0; text-align: center;"><b>Notes:</b> Reference <a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">ligands</a> (100%) were <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a> for the <a href="/wiki/Progesterone_receptor" title="Progesterone receptor"><abbr title="progesterone receptor">PR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip progesterone receptor</span>, <a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">testosterone</a> for the <a href="/wiki/Androgen_receptor" title="Androgen receptor"><abbr title="androgen receptor">AR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip androgen receptor</span>, <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a> for the <a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip estrogen receptor</span>, <a href="/wiki/Dexamethasone" title="Dexamethasone">dexamethasone</a> for the <a href="/wiki/Glucocorticoid_receptor" title="Glucocorticoid receptor"><abbr title="glucocorticoid receptor">GR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip glucocorticoid receptor</span>, <a href="/wiki/Aldosterone" title="Aldosterone">aldosterone</a> for the <a href="/wiki/Mineralocorticoid_receptor" title="Mineralocorticoid receptor"><abbr title="mineralocorticoid receptor">MR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip mineralocorticoid receptor</span>, <a href="/wiki/Androstanolone" title="Androstanolone">dihydrotestosterone</a> for <a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin"><abbr title="sex hormone-binding globulin">SHBG</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip sex hormone-binding globulin</span>, and <a href="/wiki/Hydrocortisone" title="Hydrocortisone">cortisol</a> for <a href="/wiki/Corticosteroid-binding_globulin" class="mw-redirect" title="Corticosteroid-binding globulin"><abbr title="Corticosteroid-binding globulin">CBG</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Corticosteroid-binding globulin</span>. <b>Sources:</b> See template. </td></tr></tbody></table> <table class="wikitable sortable mw-collapsible mw-collapsed" style="text-align:left; margin-left:auto; margin-right:auto; border:none;"> <caption class="nowrap"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Affinities_and_estrogenic_potencies_of_estrogen_esters_and_ethers_at_the_estrogen_receptors" title="Template:Affinities and estrogenic potencies of estrogen esters and ethers at the estrogen receptors"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Affinities_and_estrogenic_potencies_of_estrogen_esters_and_ethers_at_the_estrogen_receptors" title="Template talk:Affinities and estrogenic potencies of estrogen esters and ethers at the estrogen receptors"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Affinities_and_estrogenic_potencies_of_estrogen_esters_and_ethers_at_the_estrogen_receptors" title="Special:EditPage/Template:Affinities and estrogenic potencies of estrogen esters and ethers at the estrogen receptors"><abbr title="Edit this template">e</abbr></a></li></ul></div> Affinities and estrogenic potencies of estrogen esters and ethers at the estrogen receptors </caption> <tbody><tr> <th rowspan="2"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogen</a> </th> <th rowspan="2" class="unsortable">Other names </th> <th><a href="/wiki/Relative_binding_affinity" class="mw-redirect" title="Relative binding affinity"><abbr title="Relative binding affinity">RBA</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Relative binding affinity</span> (%)<sup>a</sup> </th> <th colspan="2"><a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)"><abbr title="Relative estrogenic potency">REP</abbr></a> (%)<sup>b</sup> </th></tr> <tr> <th><a href="/wiki/Estrogen_receptor" title="Estrogen receptor">ER</a> </th> <th><a href="/wiki/ER%CE%B1" class="mw-redirect" title="ERα">ERα</a> </th> <th><a href="/wiki/ER%CE%B2" class="mw-redirect" title="ERβ">ERβ</a> </th></tr> <tr> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a> </td> <td>E2 </td> <td>100 </td> <td>100 </td> <td>100 </td></tr> <tr> <td><a href="/wiki/Estradiol_3-sulfate" class="mw-redirect" title="Estradiol 3-sulfate">Estradiol 3-sulfate</a> </td> <td>E2S; E2-3S </td> <td>? </td> <td>0.02 </td> <td>0.04 </td></tr> <tr> <td><a href="/wiki/Estradiol_3-glucuronide" title="Estradiol 3-glucuronide">Estradiol 3-glucuronide</a> </td> <td>E2-3G </td> <td>? </td> <td>0.02 </td> <td>0.09 </td></tr> <tr> <td><a href="/wiki/Estradiol_17%CE%B2-glucuronide" class="mw-redirect" title="Estradiol 17β-glucuronide">Estradiol 17β-glucuronide</a> </td> <td>E2-17G </td> <td>? </td> <td>0.002 </td> <td>0.0002 </td></tr> <tr> <td><a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">Estradiol benzoate</a> </td> <td>EB; Estradiol 3-benzoate </td> <td>10 </td> <td>1.1 </td> <td>0.52 </td></tr> <tr> <td><a href="/wiki/Estradiol_17%CE%B2-acetate" title="Estradiol 17β-acetate">Estradiol 17β-acetate</a> </td> <td>E2-17A </td> <td>31–45 </td> <td>24 </td> <td>? </td></tr> <tr> <td><a href="/wiki/Estradiol_diacetate" title="Estradiol diacetate">Estradiol diacetate</a> </td> <td>EDA; Estradiol 3,17β-diacetate </td> <td>? </td> <td>0.79 </td> <td>? </td></tr> <tr> <td><a href="/wiki/Estradiol_17%CE%B2-propionate" class="mw-redirect" title="Estradiol 17β-propionate">Estradiol propionate</a> </td> <td>EP; Estradiol 17β-propionate </td> <td>19–26 </td> <td>2.6 </td> <td>? </td></tr> <tr> <td><a href="/wiki/Estradiol_valerate" title="Estradiol valerate">Estradiol valerate</a> </td> <td>EV; Estradiol 17β-valerate </td> <td>2–11 </td> <td>0.04–21 </td> <td>? </td></tr> <tr> <td><a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">Estradiol cypionate</a> </td> <td>EC; Estradiol 17β-cypionate </td> <td>?<sup>c</sup> </td> <td>4.0 </td> <td>? </td></tr> <tr> <td><a href="/wiki/Estradiol_palmitate" title="Estradiol palmitate">Estradiol palmitate</a> </td> <td>Estradiol 17β-palmitate </td> <td>0 </td> <td>? </td> <td>? </td></tr> <tr> <td><a href="/wiki/Estradiol_stearate" title="Estradiol stearate">Estradiol stearate</a> </td> <td>Estradiol 17β-stearate </td> <td>0 </td> <td>? </td> <td>? </td></tr> <tr> <td><a href="/wiki/Estrone_(medication)" title="Estrone (medication)">Estrone</a> </td> <td>E1; 17-Ketoestradiol </td> <td>11 </td> <td>5.3–38 </td> <td>14 </td></tr> <tr> <td><a href="/wiki/Estrone_sulfate" title="Estrone sulfate">Estrone sulfate</a> </td> <td>E1S; Estrone 3-sulfate </td> <td>2 </td> <td>0.004 </td> <td>0.002 </td></tr> <tr> <td><a href="/wiki/Estrone_glucuronide" title="Estrone glucuronide">Estrone glucuronide</a> </td> <td>E1G; Estrone 3-glucuronide </td> <td>? </td> <td><0.001 </td> <td>0.0006 </td></tr> <tr> <td><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a> </td> <td>EE; 17α-Ethynylestradiol </td> <td>100 </td> <td>17–150 </td> <td>129 </td></tr> <tr> <td><a href="/wiki/Mestranol" title="Mestranol">Mestranol</a> </td> <td>EE 3-methyl ether </td> <td>1 </td> <td>1.3–8.2 </td> <td>0.16 </td></tr> <tr> <td><a href="/wiki/Quinestrol" title="Quinestrol">Quinestrol</a> </td> <td>EE 3-cyclopentyl ether </td> <td>? </td> <td>0.37 </td> <td>? </td></tr> <tr class="sortbottom"> <td colspan="7" style="width: 1px; background-color:#eaecf0; text-align: center;"><b>Footnotes:</b> <sup>a</sup> = <a href="/wiki/Relative_binding_affinity" class="mw-redirect" title="Relative binding affinity">Relative binding affinities</a> (RBAs) were determined via <i><a href="/wiki/In_vitro" title="In vitro">in-vitro</a></i> displacement of <a href="/wiki/Radiolabel" class="mw-redirect" title="Radiolabel">labeled</a> <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a> from <a href="/wiki/Estrogen_receptor" title="Estrogen receptor">estrogen receptors</a> (ERs) generally of <a href="/wiki/Rodent" title="Rodent">rodent</a> <a href="/wiki/Uterus" title="Uterus">uterine</a> <a href="/wiki/Cytosol" title="Cytosol">cytosol</a>. <a href="/wiki/Estrogen_ester" title="Estrogen ester">Estrogen esters</a> are variably <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolyzed</a> into estrogens in these systems (shorter ester chain length -> greater rate of hydrolysis) and the ER RBAs of the esters decrease strongly when hydrolysis is prevented. <sup>b</sup> = Relative estrogenic potencies (REPs) were calculated from <a href="/wiki/Half-maximal_effective_concentration" class="mw-redirect" title="Half-maximal effective concentration">half-maximal effective concentrations</a> (EC<sub>50</sub>) that were determined via <i>in-vitro</i> <a href="/wiki/%CE%92%E2%80%90galactosidase" class="mw-redirect" title="Β‐galactosidase">β‐galactosidase</a> (β-gal) and <a href="/wiki/Green_fluorescent_protein" title="Green fluorescent protein">green fluorescent protein</a> (GFP) <a href="/wiki/Biosynthesis" title="Biosynthesis">production</a> <a href="/wiki/Bioassay" title="Bioassay">assays</a> in <a href="/wiki/Yeast" title="Yeast">yeast</a> expressing human <a href="/wiki/ER%CE%B1" class="mw-redirect" title="ERα">ERα</a> and human <a href="/wiki/ER%CE%B2" class="mw-redirect" title="ERβ">ERβ</a>. Both <a href="/wiki/Mammal" title="Mammal">mammalian</a> <a href="/wiki/Cell_(biology)" title="Cell (biology)">cells</a> and yeast have the capacity to hydrolyze estrogen esters. <sup>c</sup> = The affinities of <a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">estradiol cypionate</a> for the ERs are similar to those of <a href="/wiki/Estradiol_valerate" title="Estradiol valerate">estradiol valerate</a> and <a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">estradiol benzoate</a> (<a href="/wiki/File:Inhibition_of_estradiol_binding_by_selected_estrogens,_antiestrogens,_and_estrogen_esters_to_human_aortic_tissue_in_vitro.png" title="File:Inhibition of estradiol binding by selected estrogens, antiestrogens, and estrogen esters to human aortic tissue in vitro.png">figure</a>). <b>Sources:</b> See template page. </td></tr></tbody></table> <table class="wikitable sortable mw-collapsible" style="text-align:left; margin-left:auto; margin-right:auto; border:none;"> <caption class="nowrap"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Selected_biological_properties_of_endogenous_estrogens_in_rats" title="Template:Selected biological properties of endogenous estrogens in rats"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Selected_biological_properties_of_endogenous_estrogens_in_rats" title="Template talk:Selected biological properties of endogenous estrogens in rats"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Selected_biological_properties_of_endogenous_estrogens_in_rats" title="Special:EditPage/Template:Selected biological properties of endogenous estrogens in rats"><abbr title="Edit this template">e</abbr></a></li></ul></div> Selected biological properties of endogenous estrogens in rats </caption> <tbody><tr> <th><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogen</a></th> <th><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor</span> <a href="/wiki/Relative_binding_affinity" class="mw-redirect" title="Relative binding affinity"><abbr title="relative binding affinity">RBA</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip relative binding affinity</span> (%)</th> <th><a href="/wiki/Uterus" title="Uterus">Uterine weight</a> (%)</th> <th><a href="/wiki/Uterotrophy" class="mw-redirect" title="Uterotrophy">Uterotrophy</a></th> <th><a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone"><abbr title="Luteinizing hormone">LH</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Luteinizing hormone</span> levels (%)</th> <th><a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin"><abbr title="Sex hormone-binding globulin">SHBG</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Sex hormone-binding globulin</span> <a href="/wiki/Relative_binding_affinity" class="mw-redirect" title="Relative binding affinity"><abbr title="relative binding affinity">RBA</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip relative binding affinity</span> (%) </th></tr> <tr> <td>Control</td> <td>–</td> <td>100</td> <td>–</td> <td>100</td> <td>– </td></tr> <tr> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol (E2)</a></td> <td>100</td> <td>506 ± 20</td> <td>+++</td> <td>12–19</td> <td>100 </td></tr> <tr> <td><a href="/wiki/Estrone_(medication)" title="Estrone (medication)">Estrone (E1)</a></td> <td>11 ± 8</td> <td>490 ± 22</td> <td>+++</td> <td>?</td> <td>20 </td></tr> <tr> <td><a href="/wiki/Estriol_(medication)" title="Estriol (medication)">Estriol (E3)</a></td> <td>10 ± 4</td> <td>468 ± 30</td> <td>+++</td> <td>8–18</td> <td>3 </td></tr> <tr> <td><a href="/wiki/Estetrol_(medication)" title="Estetrol (medication)">Estetrol (E4)</a></td> <td>0.5 ± 0.2</td> <td>?</td> <td>Inactive</td> <td>?</td> <td>1 </td></tr> <tr> <td><a href="/wiki/Alfatradiol" title="Alfatradiol">17α-Estradiol</a></td> <td>4.2 ± 0.8</td> <td>?</td> <td>?</td> <td>?</td> <td>? </td></tr> <tr> <td><a href="/wiki/2-Hydroxyestradiol" title="2-Hydroxyestradiol">2-Hydroxyestradiol</a></td> <td>24 ± 7</td> <td>285 ± 8</td> <td>+<sup>b</sup></td> <td>31–61</td> <td>28 </td></tr> <tr> <td><a href="/wiki/2-Methoxyestradiol" title="2-Methoxyestradiol">2-Methoxyestradiol</a></td> <td>0.05 ± 0.04</td> <td>101</td> <td>Inactive</td> <td>?</td> <td>130 </td></tr> <tr> <td><a href="/wiki/4-Hydroxyestradiol" title="4-Hydroxyestradiol">4-Hydroxyestradiol</a></td> <td>45 ± 12</td> <td>?</td> <td>?</td> <td>?</td> <td>? </td></tr> <tr> <td><a href="/wiki/4-Methoxyestradiol" title="4-Methoxyestradiol">4-Methoxyestradiol</a></td> <td>1.3 ± 0.2</td> <td>260</td> <td>++</td> <td>?</td> <td>9 </td></tr> <tr> <td><a href="/wiki/4-Fluoroestradiol" title="4-Fluoroestradiol">4-Fluoroestradiol</a><sup>a</sup></td> <td>180 ± 43</td> <td>?</td> <td>+++</td> <td>?</td> <td>? </td></tr> <tr> <td><a href="/wiki/2-Hydroxyestrone" title="2-Hydroxyestrone">2-Hydroxyestrone</a></td> <td>1.9 ± 0.8</td> <td>130 ± 9</td> <td>Inactive</td> <td>110–142</td> <td>8 </td></tr> <tr> <td><a href="/wiki/2-Methoxyestrone" title="2-Methoxyestrone">2-Methoxyestrone</a></td> <td>0.01 ± 0.00</td> <td>103 ± 7</td> <td>Inactive</td> <td>95–100</td> <td>120 </td></tr> <tr> <td><a href="/wiki/4-Hydroxyestrone" title="4-Hydroxyestrone">4-Hydroxyestrone</a></td> <td>11 ± 4</td> <td>351</td> <td>++</td> <td>21–50</td> <td>35 </td></tr> <tr> <td><a href="/wiki/4-Methoxyestrone" title="4-Methoxyestrone">4-Methoxyestrone</a></td> <td>0.13 ± 0.04</td> <td>338</td> <td>++</td> <td>65–92</td> <td>12 </td></tr> <tr> <td><a href="/wiki/16%CE%B1-Hydroxyestrone" title="16α-Hydroxyestrone">16α-Hydroxyestrone</a></td> <td>2.8 ± 1.0</td> <td>552 ± 42</td> <td>+++</td> <td>7–24</td> <td><0.5 </td></tr> <tr> <td><a href="/wiki/2-Hydroxyestriol" title="2-Hydroxyestriol">2-Hydroxyestriol</a></td> <td>0.9 ± 0.3</td> <td>302</td> <td>+<sup>b</sup></td> <td>?</td> <td>? </td></tr> <tr> <td><a href="/wiki/2-Methoxyestriol" title="2-Methoxyestriol">2-Methoxyestriol</a></td> <td>0.01 ± 0.00</td> <td>?</td> <td>Inactive</td> <td>?</td> <td>4 </td></tr> <tr class="sortbottom"> <td colspan="6" style="width: 1px; background-color:#eaecf0; text-align: center;"><b>Notes:</b> Values are mean ± SD or range. <abbr title="estrogen receptor">ER</abbr> <abbr title="Relative binding affinity">RBA</abbr> = <a href="/wiki/Relative_binding_affinity" class="mw-redirect" title="Relative binding affinity">Relative binding affinity</a> to <a href="/wiki/Estrogen_receptor" title="Estrogen receptor">estrogen receptors</a> of rat <a href="/wiki/Uterus" title="Uterus">uterine</a> <a href="/wiki/Cytosol" title="Cytosol">cytosol</a>. Uterine weight = Percentage change in uterine wet weight of <a href="/wiki/Ovariectomy" class="mw-redirect" title="Ovariectomy">ovariectomized</a> rats after 72 hours with continuous administration of 1 μg/hour via <a href="/wiki/Subcutaneous_implant" title="Subcutaneous implant">subcutaneously implanted</a> <a href="/wiki/Osmotic_pump" class="mw-redirect" title="Osmotic pump">osmotic pumps</a>. <abbr title="Luteinizing hormone">LH</abbr> levels = <a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone">Luteinizing hormone</a> levels relative to baseline of ovariectomized rats after 24 to 72 hours of continuous administration via subcutaneous implant. <b>Footnotes:</b> <sup>a</sup> = <a href="/wiki/Synthetic_compound" class="mw-redirect" title="Synthetic compound">Synthetic</a> (i.e., not <a href="/wiki/Endogenous" class="mw-redirect" title="Endogenous">endogenous</a>). <sup>b</sup> = Atypical uterotrophic effect which plateaus within 48 hours (estradiol's uterotrophy continues linearly up to 72 hours). <b>Sources:</b> See template. </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Overview_of_actions">Overview of actions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estrogen&action=edit&section=3" title="Edit section: Overview of actions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1251242444">.mw-parser-output .ambox{border:1px solid #a2a9b1;border-left:10px solid #36c;background-color:#fbfbfb;box-sizing:border-box}.mw-parser-output .ambox+link+.ambox,.mw-parser-output .ambox+link+style+.ambox,.mw-parser-output .ambox+link+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+style+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+link+.ambox{margin-top:-1px}html body.mediawiki .mw-parser-output .ambox.mbox-small-left{margin:4px 1em 4px 0;overflow:hidden;width:238px;border-collapse:collapse;font-size:88%;line-height:1.25em}.mw-parser-output .ambox-speedy{border-left:10px solid #b32424;background-color:#fee7e6}.mw-parser-output .ambox-delete{border-left:10px solid #b32424}.mw-parser-output .ambox-content{border-left:10px solid #f28500}.mw-parser-output .ambox-style{border-left:10px solid #fc3}.mw-parser-output .ambox-move{border-left:10px solid #9932cc}.mw-parser-output .ambox-protection{border-left:10px solid #a2a9b1}.mw-parser-output .ambox .mbox-text{border:none;padding:0.25em 0.5em;width:100%}.mw-parser-output .ambox .mbox-image{border:none;padding:2px 0 2px 0.5em;text-align:center}.mw-parser-output .ambox .mbox-imageright{border:none;padding:2px 0.5em 2px 0;text-align:center}.mw-parser-output .ambox .mbox-empty-cell{border:none;padding:0;width:1px}.mw-parser-output .ambox .mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-Prose plainlinks metadata ambox ambox-style ambox-Prose" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/f/f2/Edit-clear.svg/40px-Edit-clear.svg.png" decoding="async" width="40" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/f2/Edit-clear.svg/60px-Edit-clear.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/f2/Edit-clear.svg/80px-Edit-clear.svg.png 2x" data-file-width="48" data-file-height="48" /></span></span></div></td><td class="mbox-text"><div class="mbox-text-span">This section <b>is in <a href="/wiki/MOS:LIST" class="mw-redirect" title="MOS:LIST">list</a> format but may read better as <a href="/wiki/MOS:PROSE" class="mw-redirect" title="MOS:PROSE">prose</a></b>.<span class="hide-when-compact"> You can help by <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Estrogen&action=edit">converting this section</a>, if appropriate. <a href="/wiki/Help:Editing" title="Help:Editing">Editing help</a> is available.</span> <span class="date-container"><i>(<span class="date">October 2019</span>)</i></span></div></td></tr></tbody></table> <ul><li>Musculoskeletal <ul><li><a href="/wiki/Anabolic" class="mw-redirect" title="Anabolic">Anabolic</a>: Increases <a href="/wiki/Muscle_mass" class="mw-redirect" title="Muscle mass">muscle mass</a> and strength, speed of muscle regeneration, and <a href="/wiki/Bone_density" title="Bone density">bone density</a>, increased sensitivity to exercise, protection against muscle damage, stronger <a href="/wiki/Collagen" title="Collagen">collagen</a> synthesis, increases the collagen content of <a href="/wiki/Connective_tissues" class="mw-redirect" title="Connective tissues">connective tissues</a>, <a href="/wiki/Tendon" title="Tendon">tendons</a>, and <a href="/wiki/Ligament" title="Ligament">ligaments</a>, but also decreases stiffness of <a href="/wiki/Tendon" title="Tendon">tendons</a> and <a href="/wiki/Ligament" title="Ligament">ligaments</a> (especially during <a href="/wiki/Menstruation" title="Menstruation">menstruation</a>). Decreased stiffness of tendons gives women much lower predisposition to muscle strains but soft ligaments are much more prone to injuries (<a href="/wiki/Anterior_cruciate_ligament_injury" title="Anterior cruciate ligament injury">ACL</a> tears are 2-8x more common among women than men).<sup id="cite_ref-urlFrontiers_|_Effect_of_Estrogen_on_Musculoskeletal_Performance_and_Injury_Risk_|_Physiology_26-0" class="reference"><a href="#cite_note-urlFrontiers_|_Effect_of_Estrogen_on_Musculoskeletal_Performance_and_Injury_Risk_|_Physiology-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-urlMechanisms_behind_Estrogens'_Beneficial_Effect_on_Muscle_Strength_in_Females_27-0" class="reference"><a href="#cite_note-urlMechanisms_behind_Estrogens'_Beneficial_Effect_on_Muscle_Strength_in_Females-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Max_1984_28-0" class="reference"><a href="#cite_note-Max_1984-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid1958566_29-0" class="reference"><a href="#cite_note-pmid1958566-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup></li> <li>Reduce <a href="/wiki/Bone_resorption" title="Bone resorption">bone resorption</a>, increase bone formation</li> <li>In mice, estrogen has been shown to increase the proportion of the fastest-twitch (type IIX) muscle fibers by over 40%.<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></li></ul></li> <li>Metabolic <ul><li>Anti-inflammatory properties</li> <li>Accelerate <a href="/wiki/Metabolism" title="Metabolism">metabolism</a></li> <li><a href="/wiki/Gynoid_fat_distribution" title="Gynoid fat distribution">Gynoid fat distribution</a>: increased <a href="/wiki/Fat_distribution" class="mw-redirect" title="Fat distribution">fat storage</a> or <a href="/wiki/Estrogenic_fat" title="Estrogenic fat">estrogenic fat</a> in some body parts such as breasts, buttocks, and legs but decreased abdominal and <a href="/wiki/Visceral_fat" class="mw-redirect" title="Visceral fat">visceral fat</a> (androgenic obesity).<sup id="cite_ref-pmid30097511_31-0" class="reference"><a href="#cite_note-pmid30097511-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-urlMetabolic_impact_of_sex_hormones_on_obesity_-_PubMed_32-0" class="reference"><a href="#cite_note-urlMetabolic_impact_of_sex_hormones_on_obesity_-_PubMed-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-urlTestosterone_and_Visceral_Fat_in_Midlife_Women:_The_Study_of_Women's_Health_Across_the_Nation_(SWAN)_Fat_Patterning_Study_33-0" class="reference"><a href="#cite_note-urlTestosterone_and_Visceral_Fat_in_Midlife_Women:_The_Study_of_Women's_Health_Across_the_Nation_(SWAN)_Fat_Patterning_Study-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a> also regulates energy expenditure, body weight <a href="/wiki/Homeostasis" title="Homeostasis">homeostasis</a>, and seems to have much stronger anti-obesity effects than testosterone in general.<sup id="cite_ref-urlChapter_24:_Estrogens_and_Body_Weight_Regulation_in_Men_34-0" class="reference"><a href="#cite_note-urlChapter_24:_Estrogens_and_Body_Weight_Regulation_in_Men-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup></li></ul></li> <li>Other structural <ul><li>Maintenance of vessels and skin</li></ul></li> <li><a href="/wiki/Protein" title="Protein">Protein</a> synthesis <ul><li>Increase <a href="/wiki/Hepatic_production" class="mw-redirect" title="Hepatic production">hepatic production</a> of <a href="/wiki/Binding_protein" title="Binding protein">binding proteins</a></li> <li>Increase production of the hepatokine <a href="/wiki/Adropin" title="Adropin">adropin</a>.<sup id="cite_ref-Hepatic_adropin_is_regulated_by_est_35-0" class="reference"><a href="#cite_note-Hepatic_adropin_is_regulated_by_est-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup></li></ul></li> <li><a href="/wiki/Coagulation" title="Coagulation">Coagulation</a> <ul><li>Increase circulating level of <a href="/wiki/Coagulation_factor" class="mw-redirect" title="Coagulation factor">factors</a> <a href="/wiki/Factor_II" class="mw-redirect" title="Factor II">2</a>, <a href="/wiki/Factor_VII" title="Factor VII">7</a>, <a href="/wiki/Factor_IX" title="Factor IX">9</a>, <a href="/wiki/Factor_X" title="Factor X">10</a>, <a href="/wiki/Plasminogen" class="mw-redirect" title="Plasminogen">plasminogen</a></li> <li>Decrease <a href="/wiki/Antithrombin" title="Antithrombin">antithrombin</a> III</li> <li>Increase <a href="/wiki/Platelet" title="Platelet">platelet</a> adhesiveness</li> <li>Increase <a href="/wiki/Von_Willebrand_factor" title="Von Willebrand factor">vWF</a> (estrogen -> <a href="/wiki/Angiotensin" title="Angiotensin">Angiotensin II</a> -> <a href="/wiki/Vasopressin" title="Vasopressin">Vasopressin</a>)</li> <li>Increase <a href="/wiki/PAI-1" class="mw-redirect" title="PAI-1">PAI-1</a> and <a href="/wiki/Plasminogen_activator_inhibitor-2" title="Plasminogen activator inhibitor-2">PAI-2</a> also through Angiotensin II</li></ul></li> <li><a href="/wiki/Lipid" title="Lipid">Lipid</a> <ul><li>Increase <a href="/wiki/High_density_lipoprotein" class="mw-redirect" title="High density lipoprotein">HDL</a>, <a href="/wiki/Triglyceride" title="Triglyceride">triglyceride</a></li> <li>Decrease <a href="/wiki/Low_density_lipoprotein" class="mw-redirect" title="Low density lipoprotein">LDL</a>, fat deposition</li></ul></li> <li>Fluid balance <ul><li>Salt (<a href="/wiki/Sodium_in_biology" title="Sodium in biology">sodium</a>) and water retention, including facial swelling and <a href="/wiki/Edema" title="Edema">edema</a><sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup></li> <li>Estrogen is associated with <a href="/wiki/Edema" title="Edema">edema</a>, including facial and abdominal swelling.</li></ul></li> <li><a href="/wiki/Melanin" title="Melanin">Melanin</a> <ul><li>Estrogen is known to cause darkening of skin, especially in the face and <a href="/wiki/Areolae" class="mw-redirect" title="Areolae">areolae</a>.<sup id="cite_ref-Pawlina_2023_p._1481_38-0" class="reference"><a href="#cite_note-Pawlina_2023_p._1481-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> Pale skinned women will develop browner and yellower skin during pregnancy, as a result of the increase of estrogen, known as the <a href="/wiki/Melasma" title="Melasma">"mask of pregnancy"</a>.<sup id="cite_ref-Greenberg_Bruess_Oswalt_2014_p._248_39-0" class="reference"><a href="#cite_note-Greenberg_Bruess_Oswalt_2014_p._248-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> Estrogen may explain why women have darker eyes than men, and also a lower risk of skin cancer than men; a European study found that women generally have darker skin than men.<sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup></li></ul></li> <li><a href="/wiki/Lung_function" class="mw-redirect" title="Lung function">Lung function</a> <ul><li>Promotes lung function by supporting <a href="/wiki/Pulmonary_alveolus" title="Pulmonary alveolus">alveoli</a> (in rodents but probably in humans).<sup id="cite_ref-pmid15298854_42-0" class="reference"><a href="#cite_note-pmid15298854-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup></li></ul></li> <li>Sexual <ul><li>Mediate formation of female <a href="/wiki/Secondary_sex_characteristics" class="mw-redirect" title="Secondary sex characteristics">secondary sex characteristics</a></li> <li>Stimulate <a href="/wiki/Endometrium" title="Endometrium">endometrial</a> growth</li> <li>Increase <a href="/wiki/Uterus" title="Uterus">uterine</a> growth</li> <li>Increase <a href="/wiki/Vaginal_lubrication" title="Vaginal lubrication">vaginal lubrication</a></li> <li>Thicken the <a href="/wiki/Vagina" title="Vagina">vaginal</a> wall</li></ul></li> <li><a href="/wiki/Uterus" title="Uterus">Uterus</a> lining <ul><li>Estrogen together with <a href="/wiki/Progesterone" title="Progesterone">progesterone</a> promotes and maintains the uterus lining in preparation for implantation of fertilized egg and maintenance of uterus function during gestation period, also upregulates <a href="/wiki/Oxytocin" title="Oxytocin">oxytocin</a> receptor in myometrium</li></ul></li> <li><a href="/wiki/Ovulation" title="Ovulation">Ovulation</a> <ul><li>Surge in estrogen level induces the release of <a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone">luteinizing hormone</a>, which then triggers ovulation by releasing the egg from the <a href="/wiki/Graafian_follicle" class="mw-redirect" title="Graafian follicle">Graafian follicle</a> in the <a href="/wiki/Ovary" title="Ovary">ovary</a>.</li></ul></li> <li><a href="/wiki/Sexual_behavior" class="mw-redirect" title="Sexual behavior">Sexual behavior</a> <ul><li>Estrogen is required for female mammals to engage in <a href="/wiki/Lordosis_behavior" title="Lordosis behavior">lordosis behavior</a> during <a href="/wiki/Estrus" class="mw-redirect" title="Estrus">estrus</a> (when animals are "in heat").<sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid21851428_44-0" class="reference"><a href="#cite_note-pmid21851428-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> This behavior is required for sexual receptivity in these mammals and is regulated by the <a href="/wiki/Ventromedial_nucleus" class="mw-redirect" title="Ventromedial nucleus">ventromedial nucleus</a> of the <a href="/wiki/Hypothalamus" title="Hypothalamus">hypothalamus</a>.<sup id="cite_ref-pmid9638959_45-0" class="reference"><a href="#cite_note-pmid9638959-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Sex_drive" class="mw-redirect" title="Sex drive">Sex drive</a> is dependent on <a href="/wiki/Androgen" title="Androgen">androgen</a> levels<sup id="cite_ref-pmid16037752_46-0" class="reference"><a href="#cite_note-pmid16037752-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> only in the presence of estrogen, but without estrogen, free testosterone level actually decreases sexual desire (instead of increasing sex drive), as demonstrated for those women who have <a href="/wiki/Hypoactive_sexual_desire_disorder" title="Hypoactive sexual desire disorder">hypoactive sexual desire disorder</a>, and the sexual desire in these women can be restored by administration of estrogen (using oral contraceptive).<sup id="cite_ref-pmid21514299_47-0" class="reference"><a href="#cite_note-pmid21514299-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup></li></ul></li></ul> <div class="mw-heading mw-heading3"><h3 id="Female_pubertal_development">Female pubertal development</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estrogen&action=edit&section=4" title="Edit section: Female pubertal development"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Estrogens are responsible for the development of female <a href="/wiki/Secondary_sexual_characteristic" class="mw-redirect" title="Secondary sexual characteristic">secondary sexual characteristics</a> during <a href="/wiki/Puberty" title="Puberty">puberty</a>, including <a href="/wiki/Breast_development" title="Breast development">breast development</a>, widening of the <a href="/wiki/Hip" title="Hip">hips</a>, and female <a href="/wiki/Fat_distribution" class="mw-redirect" title="Fat distribution">fat distribution</a>. Conversely, <a href="/wiki/Androgen" title="Androgen">androgens</a> are responsible for <a href="/wiki/Pubic_hair" title="Pubic hair">pubic</a> and <a href="/wiki/Body_hair" title="Body hair">body hair</a> <a href="/wiki/Hair_growth" class="mw-redirect" title="Hair growth">growth</a>, as well as <a href="/wiki/Acne" title="Acne">acne</a> and <a href="/wiki/Body_odor" title="Body odor">axillary odor</a>. </p> <div class="mw-heading mw-heading4"><h4 id="Breast_development">Breast development</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estrogen&action=edit&section=5" title="Edit section: Breast development"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Breast_development#Biochemistry" title="Breast development">Breast development § Biochemistry</a></div> <p>Estrogen, in conjunction with <a href="/wiki/Growth_hormone" title="Growth hormone">growth hormone</a> (GH) and its secretory product <a href="/wiki/Insulin-like_growth_factor_1" title="Insulin-like growth factor 1">insulin-like growth factor 1</a> (IGF-1), is critical in mediating breast development during <a href="/wiki/Puberty" title="Puberty">puberty</a>, as well as breast maturation during <a href="/wiki/Pregnancy" title="Pregnancy">pregnancy</a> in preparation of <a href="/wiki/Lactation" title="Lactation">lactation</a> and <a href="/wiki/Breastfeeding" title="Breastfeeding">breastfeeding</a>.<sup id="cite_ref-Malley2010_48-0" class="reference"><a href="#cite_note-Malley2010-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid9516076_49-0" class="reference"><a href="#cite_note-pmid9516076-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> Estrogen is primarily and directly responsible for inducing the ductal component of breast development,<sup id="cite_ref-Johnson2003_50-0" class="reference"><a href="#cite_note-Johnson2003-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-NormanHenry2014_51-0" class="reference"><a href="#cite_note-NormanHenry2014-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-CoadDunstall2011_52-0" class="reference"><a href="#cite_note-CoadDunstall2011-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> as well as for causing <a href="/wiki/Fat_deposition" class="mw-redirect" title="Fat deposition">fat deposition</a> and <a href="/wiki/Connective_tissue" title="Connective tissue">connective tissue</a> growth.<sup id="cite_ref-Johnson2003_50-1" class="reference"><a href="#cite_note-Johnson2003-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-NormanHenry2014_51-1" class="reference"><a href="#cite_note-NormanHenry2014-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> It is also indirectly involved in the lobuloalveolar component, by increasing <a href="/wiki/Progesterone_receptor" title="Progesterone receptor">progesterone receptor</a> expression in the breasts<sup id="cite_ref-Johnson2003_50-2" class="reference"><a href="#cite_note-Johnson2003-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-CoadDunstall2011_52-1" class="reference"><a href="#cite_note-CoadDunstall2011-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HaslamOsuch2006_53-0" class="reference"><a href="#cite_note-HaslamOsuch2006-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> and by inducing the secretion of <a href="/wiki/Prolactin" title="Prolactin">prolactin</a>.<sup id="cite_ref-SilbernaglDespopoulos2011_54-0" class="reference"><a href="#cite_note-SilbernaglDespopoulos2011-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Fadem2007_55-0" class="reference"><a href="#cite_note-Fadem2007-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> Allowed for by estrogen, <a href="/wiki/Progesterone" title="Progesterone">progesterone</a> and prolactin work together to complete lobuloalveolar development during pregnancy.<sup id="cite_ref-NormanHenry2014_51-2" class="reference"><a href="#cite_note-NormanHenry2014-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Blackburn2014_56-0" class="reference"><a href="#cite_note-Blackburn2014-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Androgen" title="Androgen">Androgens</a> such as testosterone powerfully oppose estrogen action in the breasts, such as by reducing <a href="/wiki/Estrogen_receptor" title="Estrogen receptor">estrogen receptor</a> expression in them.<sup id="cite_ref-IIIBarbieri2013_57-0" class="reference"><a href="#cite_note-IIIBarbieri2013-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-WilsonNizet2015_58-0" class="reference"><a href="#cite_note-WilsonNizet2015-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Female_reproductive_system">Female reproductive system</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estrogen&action=edit&section=6" title="Edit section: Female reproductive system"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Estrogens are responsible for maturation and maintenance of the <a href="/wiki/Vagina" title="Vagina">vagina</a> and <a href="/wiki/Uterus" title="Uterus">uterus</a>, and are also involved in <a href="/wiki/Ovary" title="Ovary">ovarian</a> function, such as maturation of <a href="/wiki/Ovarian_follicle" title="Ovarian follicle">ovarian follicles</a>. In addition, estrogens play an important role in regulation of <a href="/wiki/Gonadotropin" title="Gonadotropin">gonadotropin</a> <a href="/wiki/Secretion" title="Secretion">secretion</a>. For these reasons, estrogens are required for female <a href="/wiki/Fertility" title="Fertility">fertility</a>.<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. (January 2025)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading3"><h3 id="Neuroprotection_and_DNA_repair">Neuroprotection and DNA repair</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estrogen&action=edit&section=7" title="Edit section: Neuroprotection and DNA repair"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Estrogen regulated <a href="/wiki/DNA_repair" title="DNA repair">DNA repair</a> mechanisms in the <a href="/wiki/Brain" title="Brain">brain</a> have neuroprotective effects.<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> Estrogen regulates the <a href="/wiki/Transcription_(biology)" title="Transcription (biology)">transcription</a> of DNA <a href="/wiki/Base_excision_repair" title="Base excision repair">base excision repair</a> genes as well as the translocation of the base excision repair enzymes between different subcellular compartments. </p> <div class="mw-heading mw-heading3"><h3 id="Brain_and_behavior">Brain and behavior</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estrogen&action=edit&section=8" title="Edit section: Brain and behavior"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="Sex_drive">Sex drive</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estrogen&action=edit&section=9" title="Edit section: Sex drive"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Sexual_motivation_and_hormones" class="mw-redirect" title="Sexual motivation and hormones">Sexual motivation and hormones</a></div> <p>Estrogens are involved in <a href="/wiki/Libido" title="Libido">libido</a> (sex drive) in both women and men. </p> <div class="mw-heading mw-heading4"><h4 id="Cognition">Cognition</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estrogen&action=edit&section=10" title="Edit section: Cognition"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Verbal_memory" title="Verbal memory">Verbal memory</a> scores are frequently used as one measure of higher level <a href="/wiki/Cognition" title="Cognition">cognition</a>. These scores vary in direct proportion to estrogen levels throughout the menstrual cycle, pregnancy, and menopause. Furthermore, estrogens when administered shortly after natural or surgical menopause prevents decreases in verbal memory. In contrast, estrogens have little effect on verbal memory if first administered years after menopause.<sup id="cite_ref-pmid22004260_60-0" class="reference"><a href="#cite_note-pmid22004260-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup> Estrogens also have positive influences on other measures of cognitive function.<sup id="cite_ref-pmid26109339_61-0" class="reference"><a href="#cite_note-pmid26109339-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> However the effect of estrogens on cognition is not uniformly favorable and is dependent on the timing of the dose and the type of cognitive skill being measured.<sup id="cite_ref-pmid26149525_62-0" class="reference"><a href="#cite_note-pmid26149525-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> </p><p>The protective effects of estrogens on cognition may be mediated by estrogen's anti-inflammatory effects in the brain.<sup id="cite_ref-pmid26774208_63-0" class="reference"><a href="#cite_note-pmid26774208-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup> Studies have also shown that the Met allele gene and level of estrogen mediates the efficiency of <a href="/wiki/Prefrontal_cortex" title="Prefrontal cortex">prefrontal cortex</a> dependent working memory tasks.<sup id="cite_ref-64" class="reference"><a href="#cite_note-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup><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> Researchers have urged for further research to illuminate the role of estrogen and its potential for improvement on cognitive function.<sup id="cite_ref-66" class="reference"><a href="#cite_note-66"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Mental_health">Mental health</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estrogen&action=edit&section=11" title="Edit section: Mental health"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Estrogen is considered to play a significant role in women's <a href="/wiki/Mental_health" title="Mental health">mental health</a>. Sudden estrogen withdrawal, fluctuating estrogen, and <a href="/wiki/Period_of_time" class="mw-redirect" title="Period of time">periods</a> of sustained low estrogen levels correlate with a significant lowering of mood. Clinical recovery from <a href="/wiki/Postnatal" class="mw-redirect" title="Postnatal">postpartum</a>, <a href="/wiki/Perimenopause" class="mw-redirect" title="Perimenopause">perimenopause</a>, and <a href="/wiki/Postmenopause" class="mw-redirect" title="Postmenopause">postmenopause</a> depression has been shown to be effective after levels of estrogen were stabilized and/or restored.<sup id="cite_ref-pmid16292022_67-0" class="reference"><a href="#cite_note-pmid16292022-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid16388113_68-0" class="reference"><a href="#cite_note-pmid16388113-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid17909167_69-0" class="reference"><a href="#cite_note-pmid17909167-69"><span class="cite-bracket">[</span>69<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Menstrual_psychosis" class="mw-redirect" title="Menstrual psychosis">Menstrual exacerbation (including menstrual psychosis)</a> is typically triggered by low estrogen levels,<sup id="cite_ref-70" class="reference"><a href="#cite_note-70"><span class="cite-bracket">[</span>70<span class="cite-bracket">]</span></a></sup> and is often mistaken for <a href="/wiki/Premenstrual_dysphoric_disorder" title="Premenstrual dysphoric disorder">premenstrual dysphoric disorder</a>.<sup id="cite_ref-71" class="reference"><a href="#cite_note-71"><span class="cite-bracket">[</span>71<span class="cite-bracket">]</span></a></sup> </p><p>Compulsions in male lab mice, such as those in obsessive-compulsive disorder (OCD), may be caused by low estrogen levels. When estrogen levels were raised through the increased activity of the enzyme <a href="/wiki/Aromatase" title="Aromatase">aromatase</a> in male lab mice, OCD rituals were dramatically decreased. <a href="/wiki/Hypothalamus" title="Hypothalamus">Hypothalamic</a> protein levels in the gene <a href="/wiki/Catechol-O-methyl_transferase" class="mw-redirect" title="Catechol-O-methyl transferase">COMT</a> are enhanced by increasing estrogen levels which are believed to return mice that displayed OCD rituals to normal activity. Aromatase deficiency is ultimately suspected which is involved in the synthesis of estrogen in humans and has therapeutic implications in humans having obsessive-compulsive disorder.<sup id="cite_ref-pmid16566897_72-0" class="reference"><a href="#cite_note-pmid16566897-72"><span class="cite-bracket">[</span>72<span class="cite-bracket">]</span></a></sup> </p><p>Local application of estrogen in the rat hippocampus has been shown to inhibit the re-uptake of <a href="/wiki/Serotonin" title="Serotonin">serotonin</a>. Contrarily, local application of estrogen has been shown to block the ability of <a href="/wiki/Fluvoxamine" title="Fluvoxamine">fluvoxamine</a> to slow serotonin clearance, suggesting that the same pathways which are involved in SSRI efficacy may also be affected by components of local estrogen signaling pathways.<sup id="cite_ref-pmid22225849_73-0" class="reference"><a href="#cite_note-pmid22225849-73"><span class="cite-bracket">[</span>73<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Parenthood">Parenthood</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estrogen&action=edit&section=12" title="Edit section: Parenthood"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Studies have also found that fathers had lower levels of cortisol and testosterone but higher levels of estrogen (estradiol) than did non-fathers.<sup id="cite_ref-74" class="reference"><a href="#cite_note-74"><span class="cite-bracket">[</span>74<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Binge_eating">Binge eating</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estrogen&action=edit&section=13" title="Edit section: Binge eating"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Estrogen may play a role in suppressing <a href="/wiki/Binge_eating" title="Binge eating">binge eating</a>. Hormone replacement therapy using estrogen may be a possible treatment for binge eating behaviors in females. Estrogen replacement has been shown to suppress binge eating behaviors in female mice.<sup id="cite_ref-Cao_75-0" class="reference"><a href="#cite_note-Cao-75"><span class="cite-bracket">[</span>75<span class="cite-bracket">]</span></a></sup> The mechanism by which estrogen replacement inhibits binge-like eating involves the replacement of <a href="/wiki/Serotonin" title="Serotonin">serotonin</a> (5-HT) neurons. Women exhibiting binge eating behaviors are found to have increased brain uptake of neuron 5-HT, and therefore less of the neurotransmitter serotonin in the cerebrospinal fluid.<sup id="cite_ref-Jimerson_76-0" class="reference"><a href="#cite_note-Jimerson-76"><span class="cite-bracket">[</span>76<span class="cite-bracket">]</span></a></sup> Estrogen works to activate 5-HT neurons, leading to suppression of binge like eating behaviors.<sup id="cite_ref-Cao_75-1" class="reference"><a href="#cite_note-Cao-75"><span class="cite-bracket">[</span>75<span class="cite-bracket">]</span></a></sup> </p><p>It is also suggested that there is an interaction between hormone levels and eating at different points in the female <a href="/wiki/Menstrual_cycle" title="Menstrual cycle">menstrual cycle</a>. Research has predicted increased emotional eating during hormonal flux, which is characterized by high <a href="/wiki/Progesterone" title="Progesterone">progesterone</a> and <a href="/wiki/Estradiol" title="Estradiol">estradiol</a> levels that occur during the mid-<a href="/wiki/Luteal_phase" title="Luteal phase">luteal phase</a>. It is hypothesized that these changes occur due to brain changes across the menstrual cycle that are likely a genomic effect of hormones. These effects produce menstrual cycle changes, which result in hormone release leading to behavioral changes, notably binge and emotional eating. These occur especially prominently among women who are genetically vulnerable to binge eating phenotypes.<sup id="cite_ref-Klump2013_77-0" class="reference"><a href="#cite_note-Klump2013-77"><span class="cite-bracket">[</span>77<span class="cite-bracket">]</span></a></sup> </p><p>Binge eating is associated with decreased estradiol and increased progesterone.<sup id="cite_ref-Edler_78-0" class="reference"><a href="#cite_note-Edler-78"><span class="cite-bracket">[</span>78<span class="cite-bracket">]</span></a></sup> Klump et al.<sup id="cite_ref-Klump2014_79-0" class="reference"><a href="#cite_note-Klump2014-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup> Progesterone may moderate the effects of low estradiol (such as during dysregulated eating behavior), but that this may only be true in women who have had clinically diagnosed binge episodes (BEs). Dysregulated eating is more strongly associated with such ovarian hormones in women with BEs than in women without BEs.<sup id="cite_ref-Klump2014_79-1" class="reference"><a href="#cite_note-Klump2014-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup> </p><p>The implantation of 17β-estradiol pellets in ovariectomized mice significantly reduced binge eating behaviors and injections of GLP-1 in ovariectomized mice decreased binge-eating behaviors.<sup id="cite_ref-Cao_75-2" class="reference"><a href="#cite_note-Cao-75"><span class="cite-bracket">[</span>75<span class="cite-bracket">]</span></a></sup> </p><p>The associations between binge eating, menstrual-cycle phase and ovarian hormones correlated.<sup id="cite_ref-Edler_78-1" class="reference"><a href="#cite_note-Edler-78"><span class="cite-bracket">[</span>78<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Klump2008_80-0" class="reference"><a href="#cite_note-Klump2008-80"><span class="cite-bracket">[</span>80<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Lester_81-0" class="reference"><a href="#cite_note-Lester-81"><span class="cite-bracket">[</span>81<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Masculinization_in_rodents">Masculinization in rodents</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estrogen&action=edit&section=14" title="Edit section: Masculinization in rodents"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In rodents, estrogens (which are locally aromatized from androgens in the brain) play an important role in psychosexual differentiation, for example, by masculinizing territorial behavior;<sup id="cite_ref-pmid19804754_82-0" class="reference"><a href="#cite_note-pmid19804754-82"><span class="cite-bracket">[</span>82<span class="cite-bracket">]</span></a></sup> the same is not true in humans.<sup id="cite_ref-pmid19707181_83-0" class="reference"><a href="#cite_note-pmid19707181-83"><span class="cite-bracket">[</span>83<span class="cite-bracket">]</span></a></sup> In humans, the masculinizing effects of prenatal androgens on behavior (and other tissues, with the possible exception of effects on bone) appear to act exclusively through the androgen receptor.<sup id="cite_ref-pmid11534997_84-0" class="reference"><a href="#cite_note-pmid11534997-84"><span class="cite-bracket">[</span>84<span class="cite-bracket">]</span></a></sup> Consequently, the utility of rodent models for studying human psychosexual differentiation has been questioned.<sup id="cite_ref-pmid16876166_85-0" class="reference"><a href="#cite_note-pmid16876166-85"><span class="cite-bracket">[</span>85<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Skeletal_system">Skeletal system</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estrogen&action=edit&section=15" title="Edit section: Skeletal system"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Estrogens are responsible for both the pubertal growth spurt, which causes an acceleration in linear growth, and <a href="/wiki/Epiphyseal_closure" class="mw-redirect" title="Epiphyseal closure">epiphyseal closure</a>, which limits <a href="/wiki/Human_height" title="Human height">height</a> and <a href="/wiki/Limb_(anatomy)" title="Limb (anatomy)">limb</a> length, in both females and males. In addition, estrogens are responsible for bone maturation and maintenance of <a href="/wiki/Bone_mineral_density" class="mw-redirect" title="Bone mineral density">bone mineral density</a> throughout life. Due to hypoestrogenism, the risk of <a href="/wiki/Osteoporosis" title="Osteoporosis">osteoporosis</a> increases during <a href="/wiki/Menopause" title="Menopause">menopause</a>.<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. (January 2025)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading3"><h3 id="Cardiovascular_system">Cardiovascular system</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estrogen&action=edit&section=16" title="Edit section: Cardiovascular system"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Women are less impacted by heart disease due to vasculo-protective action of estrogen which helps in preventing atherosclerosis.<sup id="cite_ref-pmid10500455_86-0" class="reference"><a href="#cite_note-pmid10500455-86"><span class="cite-bracket">[</span>86<span class="cite-bracket">]</span></a></sup> It also helps in maintaining the delicate balance between fighting infections and protecting arteries from damage thus lowering the risk of cardiovascular disease.<sup id="cite_ref-pmid21836070_87-0" class="reference"><a href="#cite_note-pmid21836070-87"><span class="cite-bracket">[</span>87<span class="cite-bracket">]</span></a></sup> During <a href="/wiki/Pregnancy" title="Pregnancy">pregnancy</a>, high levels of estrogens increase <a href="/wiki/Coagulation" title="Coagulation">coagulation</a> and the risk of <a href="/wiki/Venous_thromboembolism" class="mw-redirect" title="Venous thromboembolism">venous thromboembolism</a>. Estrogen has been shown to upregulate the <a href="/wiki/Peptide_hormone" title="Peptide hormone">peptide hormone</a> <a href="/wiki/Adropin" title="Adropin">adropin</a>.<sup id="cite_ref-Hepatic_adropin_is_regulated_by_est_35-1" class="reference"><a href="#cite_note-Hepatic_adropin_is_regulated_by_est-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable mw-collapsible" style="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:Venous_thromboembolism_incidence_during_pregnancy_and_the_postpartum_period" title="Template:Venous thromboembolism incidence during pregnancy and the postpartum period"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Venous_thromboembolism_incidence_during_pregnancy_and_the_postpartum_period" title="Template talk:Venous thromboembolism incidence during pregnancy and the postpartum period"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Venous_thromboembolism_incidence_during_pregnancy_and_the_postpartum_period" title="Special:EditPage/Template:Venous thromboembolism incidence during pregnancy and the postpartum period"><abbr title="Edit this template">e</abbr></a></li></ul></div> Absolute and relative incidence of venous thromboembolism (VTE) during pregnancy and the postpartum period </caption> <tbody><tr> <th colspan="9">Absolute incidence of first VTE per 10,000 person–years during pregnancy and the postpartum period </th></tr> <tr> <th> </th> <th colspan="2">Swedish data A </th> <th colspan="2">Swedish data B </th> <th colspan="2">English data </th> <th colspan="2">Danish data </th></tr> <tr> <th>Time period </th> <th>N </th> <th>Rate (95% CI) </th> <th>N </th> <th>Rate (95% CI) </th> <th>N </th> <th>Rate (95% CI) </th> <th>N </th> <th>Rate (95% CI) </th></tr> <tr> <td>Outside pregnancy </td> <td>1105 </td> <td>4.2 (4.0–4.4) </td> <td>1015 </td> <td>3.8 (?) </td> <td>1480 </td> <td>3.2 (3.0–3.3) </td> <td>2895 </td> <td>3.6 (3.4–3.7) </td></tr> <tr> <td>Antepartum </td> <td>995 </td> <td>20.5 (19.2–21.8) </td> <td>690 </td> <td>14.2 (13.2–15.3) </td> <td>156 </td> <td>9.9 (8.5–11.6) </td> <td>491 </td> <td>10.7 (9.7–11.6) </td></tr> <tr> <td>  Trimester 1 </td> <td>207 </td> <td>13.6 (11.8–15.5) </td> <td>172 </td> <td>11.3 (9.7–13.1) </td> <td>23 </td> <td>4.6 (3.1–7.0) </td> <td>61 </td> <td>4.1 (3.2–5.2) </td></tr> <tr> <td>  Trimester 2 </td> <td>275 </td> <td>17.4 (15.4–19.6) </td> <td>178 </td> <td>11.2 (9.7–13.0) </td> <td>30 </td> <td>5.8 (4.1–8.3) </td> <td>75 </td> <td>5.7 (4.6–7.2) </td></tr> <tr> <td>  Trimester 3 </td> <td>513 </td> <td>29.2 (26.8–31.9) </td> <td>340 </td> <td>19.4 (17.4–21.6) </td> <td>103 </td> <td>18.2 (15.0–22.1) </td> <td>355 </td> <td>19.7 (17.7–21.9) </td></tr> <tr> <td>Around delivery </td> <td>115 </td> <td>154.6 (128.8–185.6) </td> <td>79 </td> <td>106.1 (85.1–132.3) </td> <td>34 </td> <td>142.8 (102.0–199.8) </td> <td colspan="2"><div class="center" style="width:auto; margin-left:auto; margin-right:auto;">–</div> </td></tr> <tr> <td>Postpartum </td> <td>649 </td> <td>42.3 (39.2–45.7) </td> <td>509 </td> <td>33.1 (30.4–36.1) </td> <td>135 </td> <td>27.4 (23.1–32.4) </td> <td>218 </td> <td>17.5 (15.3–20.0) </td></tr> <tr> <td>  Early postpartum </td> <td>584 </td> <td>75.4 (69.6–81.8) </td> <td>460 </td> <td>59.3 (54.1–65.0) </td> <td>177 </td> <td>46.8 (39.1–56.1) </td> <td>199 </td> <td>30.4 (26.4–35.0) </td></tr> <tr> <td>  Late postpartum </td> <td>65 </td> <td>8.5 (7.0–10.9) </td> <td>49 </td> <td>6.4 (4.9–8.5) </td> <td>18 </td> <td>7.3 (4.6–11.6) </td> <td>319 </td> <td>3.2 (1.9–5.0) </td></tr> <tr> <th colspan="9">Incidence rate ratios (IRRs) of first VTE during pregnancy and the postpartum period </th></tr> <tr> <th> </th> <th colspan="2">Swedish data A </th> <th colspan="2">Swedish data B </th> <th colspan="2">English data </th> <th colspan="2">Danish data </th></tr> <tr> <th>Time period </th> <th colspan="2">IRR* (95% CI) </th> <th colspan="2">IRR* (95% CI) </th> <th colspan="2">IRR (95% CI)† </th> <th colspan="2">IRR (95% CI)† </th></tr> <tr> <td>Outside pregnancy </td> <td colspan="8"><div class="center" style="width:auto; margin-left:auto; margin-right:auto;">Reference (i.e., 1.00)</div> </td></tr> <tr> <td>Antepartum </td> <td colspan="2">5.08 (4.66–5.54) </td> <td colspan="2">3.80 (3.44–4.19) </td> <td colspan="2">3.10 (2.63–3.66) </td> <td colspan="2">2.95 (2.68–3.25) </td></tr> <tr> <td>  Trimester 1 </td> <td colspan="2">3.42 (2.95–3.98) </td> <td colspan="2">3.04 (2.58–3.56) </td> <td colspan="2">1.46 (0.96–2.20) </td> <td colspan="2">1.12 (0.86–1.45) </td></tr> <tr> <td>  Trimester 2 </td> <td colspan="2">4.31 (3.78–4.93) </td> <td colspan="2">3.01 (2.56–3.53) </td> <td colspan="2">1.82 (1.27–2.62) </td> <td colspan="2">1.58 (1.24–1.99) </td></tr> <tr> <td>  Trimester 3 </td> <td colspan="2">7.14 (6.43–7.94) </td> <td colspan="2">5.12 (4.53–5.80) </td> <td colspan="2">5.69 (4.66–6.95) </td> <td colspan="2">5.48 (4.89–6.12) </td></tr> <tr> <td>Around delivery </td> <td colspan="2">37.5 (30.9–44.45) </td> <td colspan="2">27.97 (22.24–35.17) </td> <td colspan="2">44.5 (31.68–62.54) </td> <td colspan="2"><div class="center" style="width:auto; margin-left:auto; margin-right:auto;">–</div> </td></tr> <tr> <td>Postpartum </td> <td colspan="2">10.21 (9.27–11.25) </td> <td colspan="2">8.72 (7.83–9.70) </td> <td colspan="2">8.54 (7.16–10.19) </td> <td colspan="2">4.85 (4.21–5.57) </td></tr> <tr> <td>  Early postpartum </td> <td colspan="2">19.27 (16.53–20.21) </td> <td colspan="2">15.62 (14.00–17.45) </td> <td colspan="2">14.61 (12.10–17.67) </td> <td colspan="2">8.44 (7.27–9.75) </td></tr> <tr> <td>  Late postpartum </td> <td colspan="2">2.06 (1.60–2.64) </td> <td colspan="2">1.69 (1.26–2.25) </td> <td colspan="2">2.29 (1.44–3.65) </td> <td colspan="2">0.89 (0.53–1.39) </td></tr> <tr class="sortbottom"> <td colspan="9" style="width: 1px; background-color:#eaecf0; text-align: center;"><b>Notes:</b> Swedish data A = Using any code for VTE regardless of confirmation. Swedish data B = Using only algorithm-confirmed VTE. Early postpartum = First 6 weeks after delivery. Late postpartum = More than 6 weeks after delivery. * = Adjusted for age and calendar year. † = Unadjusted ratio calculated based on the data provided. <b>Source:</b> <sup id="cite_ref-pmid26560059_88-0" class="reference"><a href="#cite_note-pmid26560059-88"><span class="cite-bracket">[</span>88<span class="cite-bracket">]</span></a></sup> </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Immune_system">Immune system</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estrogen&action=edit&section=17" title="Edit section: Immune system"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The effect of estrogen on the <a href="/wiki/Immune_system" title="Immune system">immune system</a> is in general described as <a href="/wiki/Th2" class="mw-redirect" title="Th2">Th2</a> favoring, rather than suppressive, as is the case of the effect of male sex hormone - testosterone.<sup id="cite_ref-Foo_et_al_2016_89-0" class="reference"><a href="#cite_note-Foo_et_al_2016-89"><span class="cite-bracket">[</span>89<span class="cite-bracket">]</span></a></sup> Indeed, women respond better to <a href="/wiki/Vaccine" title="Vaccine">vaccines</a>, <a href="/wiki/Infection" title="Infection">infections</a> and are generally less likely to develop <a href="/wiki/Cancer" title="Cancer">cancer</a>, the tradeoff of this is that they are more likely to develop an <a href="/wiki/Autoimmune_disease" title="Autoimmune disease">autoimmune disease</a>.<sup id="cite_ref-Taneja_2018_90-0" class="reference"><a href="#cite_note-Taneja_2018-90"><span class="cite-bracket">[</span>90<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Th2" class="mw-redirect" title="Th2">Th2</a> shift manifests itself in a decrease of cellular immunity and increase in humoral immunity (<a href="/wiki/Antibody" title="Antibody">antibody</a> production) shifts it from cellular to humoral by downregulating cell-mediated immunity and enhancing Th2 immune response by stimulating IL-4 production and Th2 differentiation.<sup id="cite_ref-Foo_et_al_2016_89-1" class="reference"><a href="#cite_note-Foo_et_al_2016-89"><span class="cite-bracket">[</span>89<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Roved_et_al_2017_91-0" class="reference"><a href="#cite_note-Roved_et_al_2017-91"><span class="cite-bracket">[</span>91<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Th1_cell" class="mw-redirect" title="Th1 cell">Type 1</a> and <a href="/wiki/Th17" class="mw-redirect" title="Th17">type 17</a> immune responses are downregulated, likely to be at least partially due to <a href="/wiki/Interleukin_4" title="Interleukin 4">IL-4</a>, which inhibits Th1. Effect of estrogen on different immune cells' cell types is in line with its Th2 bias. Activity of <a href="/wiki/Basophil" title="Basophil">basophils</a>, <a href="/wiki/Eosinophil" title="Eosinophil">eosinophils</a>, M2 <a href="/wiki/Macrophage" title="Macrophage">macrophages</a> and is enhanced, whereas activity of <a href="/wiki/NK_cell" class="mw-redirect" title="NK cell">NK cells</a> is downregulated. Conventional <a href="/wiki/Dendritic_cell" title="Dendritic cell">dendritic cells</a> are biased towards Th2 under the influence of estrogen, whereas plasmacytoid dendritic cells, key players in antiviral defence, have increased <a href="/wiki/IFN-g" class="mw-redirect" title="IFN-g">IFN-g</a> secretion.<sup id="cite_ref-Roved_et_al_2017_91-1" class="reference"><a href="#cite_note-Roved_et_al_2017-91"><span class="cite-bracket">[</span>91<span class="cite-bracket">]</span></a></sup> Estrogen also influences <a href="/wiki/B_cell" title="B cell">B cells</a> by increasing their survival, proliferation, differentiation and function, which corresponds with higher antibody and B cell count generally detected in women.<sup id="cite_ref-Khan_Ansar_2016_92-0" class="reference"><a href="#cite_note-Khan_Ansar_2016-92"><span class="cite-bracket">[</span>92<span class="cite-bracket">]</span></a></sup> </p><p>On a molecular level estrogen induces the above-mentioned effects on cell via acting on intracellular <a href="/wiki/Receptor_(biochemistry)" title="Receptor (biochemistry)">receptors</a> termed ER α and ER β, which upon ligation form either homo or heterodimers. The genetic and nongenetic targets of the receptors differ between homo and heterodimers.<sup id="cite_ref-Kovats_2015_93-0" class="reference"><a href="#cite_note-Kovats_2015-93"><span class="cite-bracket">[</span>93<span class="cite-bracket">]</span></a></sup> Ligation of these receptors allows them to translocate to the <a href="/wiki/Cell_nucleus" title="Cell nucleus">nucleus</a> and act as <a href="/wiki/Transcription_factor" title="Transcription factor">transcription factors</a> either by binding estrogen response elements (ERE) on <a href="/wiki/DNA" title="DNA">DNA</a> or binding DNA together with other transcriptional factors e.g. <a href="/w/index.php?title=Nf-kB&action=edit&redlink=1" class="new" title="Nf-kB (page does not exist)">Nf-kB</a> or <a href="/wiki/Activator_protein_1" class="mw-redirect" title="Activator protein 1">AP-1</a>, both of which result in <a href="/wiki/RNA_polymerase" title="RNA polymerase">RNA polymerase</a> recruitment and further <a href="/w/index.php?title=Chromatin_remodelation&action=edit&redlink=1" class="new" title="Chromatin remodelation (page does not exist)">chromatin remodelation</a>.<sup id="cite_ref-Kovats_2015_93-1" class="reference"><a href="#cite_note-Kovats_2015-93"><span class="cite-bracket">[</span>93<span class="cite-bracket">]</span></a></sup> A non-transcriptional response to oestrogen stimulation was also documented (termed membrane-initiated steroid signalling, MISS). This pathway stimulates the ERK and PI3K/AKT pathways, which are known to increase cellular proliferation and affect chromatin remodelation.<sup id="cite_ref-Kovats_2015_93-2" class="reference"><a href="#cite_note-Kovats_2015-93"><span class="cite-bracket">[</span>93<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Associated_conditions">Associated conditions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estrogen&action=edit&section=18" title="Edit section: Associated conditions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Researchers have implicated estrogens in various <a href="/wiki/Estrogen-dependent_condition" title="Estrogen-dependent condition">estrogen-dependent conditions</a>, such as ER-positive <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a>, as well as a number of <a href="/wiki/Genetic_condition" class="mw-redirect" title="Genetic condition">genetic conditions</a> involving estrogen signaling or metabolism, such as <a href="/wiki/Estrogen_insensitivity_syndrome" title="Estrogen insensitivity syndrome">estrogen insensitivity syndrome</a>, <a href="/wiki/Aromatase_deficiency" title="Aromatase deficiency">aromatase deficiency</a>, and <a href="/wiki/Aromatase_excess_syndrome" title="Aromatase excess syndrome">aromatase excess syndrome</a>.<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. (January 2025)">citation needed</span></a></i>]</sup> </p><p>High estrogen can amplify <a href="/wiki/Stress_hormone" title="Stress hormone">stress-hormone</a> responses in stressful situations.<sup id="cite_ref-94" class="reference"><a href="#cite_note-94"><span class="cite-bracket">[</span>94<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Biochemistry">Biochemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estrogen&action=edit&section=19" title="Edit section: Biochemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Estradiol#Biochemistry" title="Estradiol">Estradiol § Biochemistry</a></div> <div class="mw-heading mw-heading3"><h3 id="Biosynthesis">Biosynthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estrogen&action=edit&section=20" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Steroidogenesis.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/13/Steroidogenesis.svg/450px-Steroidogenesis.svg.png" decoding="async" width="450" height="399" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/13/Steroidogenesis.svg/675px-Steroidogenesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/13/Steroidogenesis.svg/900px-Steroidogenesis.svg.png 2x" data-file-width="1245" data-file-height="1105" /></a><figcaption><a href="/wiki/Steroidogenesis" class="mw-redirect" title="Steroidogenesis">Steroidogenesis</a>, showing estrogens at bottom right as in pink triangle<sup id="cite_ref-HäggströmRichfield2014_95-0" class="reference"><a href="#cite_note-HäggströmRichfield2014-95"><span class="cite-bracket">[</span>95<span class="cite-bracket">]</span></a></sup></figcaption></figure> <p>Estrogens, in females, are produced primarily by the <a href="/wiki/Ovary" title="Ovary">ovaries</a>, and during pregnancy, the <a href="/wiki/Placenta" title="Placenta">placenta</a>.<sup id="cite_ref-Marieb_96-0" class="reference"><a href="#cite_note-Marieb-96"><span class="cite-bracket">[</span>96<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Follicle-stimulating_hormone" title="Follicle-stimulating hormone">Follicle-stimulating hormone</a> (FSH) stimulates the ovarian production of estrogens by the <a href="/wiki/Granulosa_cell" title="Granulosa cell">granulosa cells</a> of the <a href="/wiki/Ovarian_follicle" title="Ovarian follicle">ovarian follicles</a> and <a href="/wiki/Corpus_luteum" title="Corpus luteum">corpora lutea</a>. Some estrogens are also produced in smaller amounts by other tissues such as the <a href="/wiki/Liver" title="Liver">liver</a>, <a href="/wiki/Pancreas" title="Pancreas">pancreas</a>, <a href="/wiki/Bone" title="Bone">bone</a>, <a href="/wiki/Adrenal_gland" title="Adrenal gland">adrenal glands</a>, <a href="/wiki/Skin" title="Skin">skin</a>, <a href="/wiki/Brain" title="Brain">brain</a>, <a href="/wiki/Adipose_tissue" title="Adipose tissue">adipose tissue</a>,<sup id="cite_ref-pmid4815174_97-0" class="reference"><a href="#cite_note-pmid4815174-97"><span class="cite-bracket">[</span>97<span class="cite-bracket">]</span></a></sup> and the <a href="/wiki/Breast" title="Breast">breasts</a>.<sup id="cite_ref-98" class="reference"><a href="#cite_note-98"><span class="cite-bracket">[</span>98<span class="cite-bracket">]</span></a></sup> These secondary sources of estrogens are especially important in postmenopausal women.<sup id="cite_ref-pmid11511861_99-0" class="reference"><a href="#cite_note-pmid11511861-99"><span class="cite-bracket">[</span>99<span class="cite-bracket">]</span></a></sup> The pathway of estrogen biosynthesis in extragonadal tissues is different. These tissues are not able to synthesize C19 steroids, and therefore depend on C19 supplies from other tissues<sup id="cite_ref-pmid11511861_99-1" class="reference"><a href="#cite_note-pmid11511861-99"><span class="cite-bracket">[</span>99<span class="cite-bracket">]</span></a></sup> and the level of aromatase.<sup id="cite_ref-100" class="reference"><a href="#cite_note-100"><span class="cite-bracket">[</span>100<span class="cite-bracket">]</span></a></sup> </p><p>In females, synthesis of estrogens starts in <a href="/wiki/Theca_interna" title="Theca interna">theca interna</a> cells in the ovary, by the synthesis of <a href="/wiki/Androstenedione" title="Androstenedione">androstenedione</a> from <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a>. Androstenedione is a substance of weak androgenic activity which serves predominantly as a <a href="/wiki/Precursor_(biochemistry)" class="mw-redirect" title="Precursor (biochemistry)">precursor</a> for more potent androgens such as testosterone as well as estrogen. This compound crosses the <a href="/wiki/Basal_membrane" class="mw-redirect" title="Basal membrane">basal membrane</a> into the surrounding granulosa cells, where it is converted either immediately into estrone, or into testosterone and then estradiol in an additional step. The conversion of androstenedione to testosterone is catalyzed by <a href="/wiki/17%CE%B2-hydroxysteroid_dehydrogenase" class="mw-redirect" title="17β-hydroxysteroid dehydrogenase">17β-hydroxysteroid dehydrogenase</a> (17β-HSD), whereas the conversion of androstenedione and testosterone into estrone and estradiol, respectively is catalyzed by aromatase, enzymes which are both expressed in granulosa cells. In contrast, granulosa cells lack <a href="/wiki/17%CE%B1-hydroxylase" class="mw-redirect" title="17α-hydroxylase">17α-hydroxylase</a> and <a href="/wiki/17,20-lyase" class="mw-redirect" title="17,20-lyase">17,20-lyase</a>, whereas theca cells express these enzymes and 17β-HSD but lack aromatase. Hence, both granulosa and theca cells are essential for the production of estrogen in the ovaries.<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. (January 2025)">citation needed</span></a></i>]</sup> </p><p>Estrogen levels vary through the <a href="/wiki/Menstrual_cycle" title="Menstrual cycle">menstrual cycle</a>, with levels highest near the end of the <a href="/wiki/Follicular_phase" title="Follicular phase">follicular phase</a> just before <a href="/wiki/Ovulation" title="Ovulation">ovulation</a>. </p><p>Note that in males, estrogen is also produced by the <a href="/wiki/Sertoli_cell" title="Sertoli cell">Sertoli cells</a> when FSH binds to their FSH receptors. </p> <table class="wikitable mw-collapsible mw-collapsed" style="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:Production_rates,_secretion_rates,_clearance_rates,_and_blood_levels_of_major_sex_hormones" title="Template:Production rates, secretion rates, clearance rates, and blood levels of major sex hormones"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Production_rates,_secretion_rates,_clearance_rates,_and_blood_levels_of_major_sex_hormones" title="Template talk:Production rates, secretion rates, clearance rates, and blood levels of major sex hormones"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Production_rates,_secretion_rates,_clearance_rates,_and_blood_levels_of_major_sex_hormones" title="Special:EditPage/Template:Production rates, secretion rates, clearance rates, and blood levels of major sex hormones"><abbr title="Edit this template">e</abbr></a></li></ul></div> Production rates, secretion rates, clearance rates, and blood levels of major sex hormones </caption> <tbody><tr> <th rowspan="2">Sex </th> <th rowspan="2">Sex hormone </th> <th rowspan="2">Reproductive<br />phase </th> <th rowspan="2">Blood<br />production rate </th> <th rowspan="2">Gonadal<br />secretion rate </th> <th rowspan="2">Metabolic<br />clearance rate </th> <th colspan="2">Reference range (serum levels) </th></tr> <tr> <th><abbr title="Système International">SI</abbr> units </th> <th>Non-<abbr title="Système International">SI</abbr> units </th></tr> <tr> <td rowspan="5">Men </td> <td><a href="/wiki/Androstenedione" title="Androstenedione">Androstenedione</a> </td> <td><div class="center" style="width:auto; margin-left:auto; margin-right:auto;">–</div> </td> <td>2.8 mg/day </td> <td>1.6 mg/day </td> <td>2200 L/day </td> <td>2.8–7.3 nmol/L </td> <td>80–210 ng/dL </td></tr> <tr> <td><a href="/wiki/Testosterone" title="Testosterone">Testosterone</a> </td> <td><div class="center" style="width:auto; margin-left:auto; margin-right:auto;">–</div> </td> <td>6.5 mg/day </td> <td>6.2 mg/day </td> <td>950 L/day </td> <td>6.9–34.7 nmol/L </td> <td>200–1000 ng/dL </td></tr> <tr> <td><a href="/wiki/Estrone" title="Estrone">Estrone</a> </td> <td><div class="center" style="width:auto; margin-left:auto; margin-right:auto;">–</div> </td> <td>150 μg/day </td> <td>110 μg/day </td> <td>2050 L/day </td> <td>37–250 pmol/L </td> <td>10–70 pg/mL </td></tr> <tr> <td><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a> </td> <td><div class="center" style="width:auto; margin-left:auto; margin-right:auto;">–</div> </td> <td>60 μg/day </td> <td>50 μg/day </td> <td>1600 L/day </td> <td><37–210 pmol/L </td> <td>10–57 pg/mL </td></tr> <tr> <td><a href="/wiki/Estrone_sulfate" title="Estrone sulfate">Estrone sulfate</a> </td> <td><div class="center" style="width:auto; margin-left:auto; margin-right:auto;">–</div> </td> <td>80 μg/day </td> <td>Insignificant </td> <td>167 L/day </td> <td>600–2500 pmol/L </td> <td>200–900 pg/mL </td></tr> <tr> <td rowspan="12">Women </td> <td><a href="/wiki/Androstenedione" title="Androstenedione">Androstenedione</a> </td> <td><div class="center" style="width:auto; margin-left:auto; margin-right:auto;">–</div> </td> <td>3.2 mg/day </td> <td>2.8 mg/day </td> <td>2000 L/day </td> <td>3.1–12.2 nmol/L </td> <td>89–350 ng/dL </td></tr> <tr> <td><a href="/wiki/Testosterone" title="Testosterone">Testosterone</a> </td> <td><div class="center" style="width:auto; margin-left:auto; margin-right:auto;">–</div> </td> <td>190 μg/day </td> <td>60 μg/day </td> <td>500 L/day </td> <td>0.7–2.8 nmol/L </td> <td>20–81 ng/dL </td></tr> <tr> <td rowspan="3"><a href="/wiki/Estrone" title="Estrone">Estrone</a> </td> <td>Follicular phase </td> <td>110 μg/day </td> <td>80 μg/day </td> <td>2200 L/day </td> <td>110–400 pmol/L </td> <td>30–110 pg/mL </td></tr> <tr> <td>Luteal phase </td> <td>260 μg/day </td> <td>150 μg/day </td> <td>2200 L/day </td> <td>310–660 pmol/L </td> <td>80–180 pg/mL </td></tr> <tr> <td>Postmenopause </td> <td>40 μg/day </td> <td>Insignificant </td> <td>1610 L/day </td> <td>22–230 pmol/L </td> <td>6–60 pg/mL </td></tr> <tr> <td rowspan="3"><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a> </td> <td>Follicular phase </td> <td>90 μg/day </td> <td>80 μg/day </td> <td>1200 L/day </td> <td><37–360 pmol/L </td> <td>10–98 pg/mL </td></tr> <tr> <td>Luteal phase </td> <td>250 μg/day </td> <td>240 μg/day </td> <td>1200 L/day </td> <td>699–1250 pmol/L </td> <td>190–341 pg/mL </td></tr> <tr> <td>Postmenopause </td> <td>6 μg/day </td> <td>Insignificant </td> <td>910 L/day </td> <td><37–140 pmol/L </td> <td>10–38 pg/mL </td></tr> <tr> <td rowspan="2"><a href="/wiki/Estrone_sulfate" title="Estrone sulfate">Estrone sulfate</a> </td> <td>Follicular phase </td> <td>100 μg/day </td> <td>Insignificant </td> <td>146 L/day </td> <td>700–3600 pmol/L </td> <td>250–1300 pg/mL </td></tr> <tr> <td>Luteal phase </td> <td>180 μg/day </td> <td>Insignificant </td> <td>146 L/day </td> <td>1100–7300 pmol/L </td> <td>400–2600 pg/mL </td></tr> <tr> <td rowspan="2"><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a> </td> <td>Follicular phase </td> <td>2 mg/day </td> <td>1.7 mg/day </td> <td>2100 L/day </td> <td>0.3–3 nmol/L </td> <td>0.1–0.9 ng/mL </td></tr> <tr> <td>Luteal phase </td> <td>25 mg/day </td> <td>24 mg/day </td> <td>2100 L/day </td> <td>19–45 nmol/L </td> <td>6–14 ng/mL </td></tr> <tr> <td colspan="8" style="width: 1px; background-color:#eaecf0; text-align: center;"><style data-mw-deduplicate="TemplateStyles:r1214851843">.mw-parser-output .hidden-begin{box-sizing:border-box;width:100%;padding:5px;border:none;font-size:95%}.mw-parser-output .hidden-title{font-weight:bold;line-height:1.6;text-align:left}.mw-parser-output .hidden-content{text-align:left}@media all and (max-width:500px){.mw-parser-output .hidden-begin{width:auto!important;clear:none!important;float:none!important}}</style><div class="hidden-begin mw-collapsible mw-collapsed" style=""><div class="hidden-title skin-nightmode-reset-color" style="text-align:center;">Notes and sources</div><div class="hidden-content mw-collapsible-content" style=""> <span style="font-size:small;"><b>Notes:</b> "The <i>concentration</i> of a steroid in the circulation is determined by the rate at which it is secreted from glands, the rate of metabolism of precursor or prehormones into the steroid, and the rate at which it is extracted by tissues and metabolized. The <i>secretion rate</i> of a steroid refers to the total secretion of the compound from a gland per unit time. Secretion rates have been assessed by sampling the venous effluent from a gland over time and subtracting out the arterial and peripheral venous hormone concentration. The <i>metabolic clearance rate</i> of a steroid is defined as the volume of blood that has been completely cleared of the hormone per unit time. The <i>production rate</i> of a steroid hormone refers to entry into the blood of the compound from all possible sources, including secretion from glands and conversion of prohormones into the steroid of interest. At steady state, the amount of hormone entering the blood from all sources will be equal to the rate at which it is being cleared (metabolic clearance rate) multiplied by blood concentration (production rate = metabolic clearance rate × concentration). If there is little contribution of prohormone metabolism to the circulating pool of steroid, then the production rate will approximate the secretion rate." <b>Sources:</b> See template.</span></div></div> </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Distribution">Distribution</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estrogen&action=edit&section=21" title="Edit section: Distribution"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Estrogens are <a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">plasma protein bound</a> to <a href="/wiki/Human_serum_albumin" title="Human serum albumin">albumin</a> and/or <a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin">sex hormone-binding globulin</a> in the circulation. </p> <div class="mw-heading mw-heading3"><h3 id="Metabolism">Metabolism</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estrogen&action=edit&section=22" title="Edit section: Metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Estradiol#Metabolism" title="Estradiol">Estradiol § Metabolism</a>, and <a href="/wiki/Estradiol_(medication)#Metabolism" title="Estradiol (medication)">Estradiol (medication) § Metabolism</a></div> <p>Estrogens are <a href="/wiki/Metabolism" title="Metabolism">metabolized</a> via <a href="/wiki/Hydroxylation" title="Hydroxylation">hydroxylation</a> by <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> <a href="/wiki/Enzyme" title="Enzyme">enzymes</a> such as <a href="/wiki/CYP1A1" title="CYP1A1">CYP1A1</a> and <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a> and via <a href="/wiki/Conjugation_(biochemistry)" class="mw-redirect" title="Conjugation (biochemistry)">conjugation</a> by <a href="/wiki/Estrogen_sulfotransferase" class="mw-redirect" title="Estrogen sulfotransferase">estrogen sulfotransferases</a> (<a href="/wiki/Sulfation" title="Sulfation">sulfation</a>) and <a href="/wiki/UDP-glucuronyltransferase" class="mw-redirect" title="UDP-glucuronyltransferase">UDP-glucuronyltransferases</a> (<a href="/wiki/Glucuronidation" title="Glucuronidation">glucuronidation</a>). In addition, estradiol is <a href="/wiki/Dehydrogenation" title="Dehydrogenation">dehydrogenated</a> by <a href="/wiki/17%CE%B2-hydroxysteroid_dehydrogenase" class="mw-redirect" title="17β-hydroxysteroid dehydrogenase">17β-hydroxysteroid dehydrogenase</a> into the much less potent estrogen estrone. These reactions occur primarily in the <a href="/wiki/Liver" title="Liver">liver</a>, but also in other <a href="/wiki/Tissue_(biology)" title="Tissue (biology)">tissues</a>.<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. (January 2025)">citation needed</span></a></i>]</sup> </p> <table role="presentation" cellpadding="0" style="border-spacing:0; margin-left: auto; margin-right: auto; border: none;"> <tbody><tr> <td><div class="thumb center" style="margin: 1em auto;"> <div class="thumbinner" style="width:487px;"> <div style="clear: both; font-weight: bold; font-size: 106.4%; text-align: center; background-color: light-dark(aliceblue,var(--background-color-neutral)); color:var(--color-base,light-dark(#202122,#eaecf0)); margin-bottom:3px;"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Estradiol_metabolism" title="Template:Estradiol metabolism"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Estradiol_metabolism" title="Template talk:Estradiol metabolism"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Estradiol_metabolism" title="Special:EditPage/Template:Estradiol metabolism"><abbr title="Edit this template">e</abbr></a></li></ul></div> Estrogen metabolism in humans</div> <div class="skin-invert" style="position:relative; width:485px; height:400px; overflow:hidden; border:solid #ccc 1px; background-color:white;"> <div style="left:0px; top:0px; width:485px; position:absolute"> <span typeof="mw:File"><span><img alt="Graphic of the metabolic pathways of estradiol in humans" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Estradiol_metabolism_structures.svg/485px-Estradiol_metabolism_structures.svg.png" decoding="async" width="485" height="385" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Estradiol_metabolism_structures.svg/728px-Estradiol_metabolism_structures.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Estradiol_metabolism_structures.svg/970px-Estradiol_metabolism_structures.svg.png 2x" data-file-width="1305" data-file-height="1036" /></span></span> </div> <div style="text-align:center; font-size:13px; line-height:110%"> <div style="background-color:transparent; color:black"><div id="annotation_40x68" style="position:absolute; left:40px; top:68px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><b><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></b> </span></div> <div id="annotation_186x68" style="position:absolute; left:186px; top:68px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Estrone_sulfate" title="Estrone sulfate">Estrone sulfate</a> </span></div> <div id="annotation_338x83" style="position:absolute; left:338px; top:83px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Estrone_glucuronide" title="Estrone glucuronide">Estrone glucuronide</a> </span></div> <p><br /> </p> <div id="annotation_10x180" style="position:absolute; left:10px; top:180px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/2-Hydroxyestrone" title="2-Hydroxyestrone">2-Hydroxyestrone</a> </span></div> <div id="annotation_210x180" style="position:absolute; left:210px; top:180px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><b><a href="/wiki/Estrone" title="Estrone">Estrone</a></b> </span></div> <div id="annotation_365x186" style="position:absolute; left:365px; top:186px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/4-Hydroxyestrone" title="4-Hydroxyestrone">4-Hydroxyestrone</a> </span></div> <p><br /> </p> <div id="annotation_10x280" style="position:absolute; left:10px; top:280px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/2-Methoxyestrone" title="2-Methoxyestrone">2-Methoxyestrone</a> </span></div> <div id="annotation_180x280" style="position:absolute; left:180px; top:280px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/16%CE%B1-Hydroxyestrone" title="16α-Hydroxyestrone">16α-Hydroxyestrone</a> </span></div> <div id="annotation_365x295" style="position:absolute; left:365px; top:295px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/4-Methoxyestrone" title="4-Methoxyestrone">4-Methoxyestrone</a> </span></div> <p><br /> </p> <div id="annotation_25x384" style="position:absolute; left:25px; top:384px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/17-Epiestriol" class="mw-redirect" title="17-Epiestriol">17-Epiestriol</a> </span></div> <div id="annotation_210x384" style="position:absolute; left:210px; top:384px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><b><a href="/wiki/Estriol" title="Estriol">Estriol</a></b> </span></div> <div id="annotation_375x384" style="position:absolute; left:375px; top:384px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/16-Epiestriol" class="mw-redirect" title="16-Epiestriol">16-Epiestriol</a> </span></div> <p><br /> </p><p><br /> </p> <div id="annotation_150x84" style="position:absolute; left:150px; top:84px; font-size:12px; font-size:12; line-height:14px; text-align:left;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/17%CE%B2-Hydroxysteroid_dehydrogenase#Overview" title="17β-Hydroxysteroid dehydrogenase"><span style="color:DeepSkyBlue">17β-HSD</span></a></span></div> <div id="annotation_192x100" style="position:absolute; left:192px; top:100px; font-size:12px; font-size:12; line-height:14px; text-align:right;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Estrone_sulfotransferase#Types" title="Estrone sulfotransferase"><span style="color:DeepSkyBlue">EST</span></a></span></div> <div id="annotation_225x100" style="position:absolute; left:225px; top:100px; font-size:12px; font-size:12; line-height:14px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Steroid_sulfatase" title="Steroid sulfatase"><span style="color:DeepSkyBlue">STS</span></a></span></div> <div id="annotation_272x76" style="position:absolute; left:272px; top:76px; font-size:12px; font-size:12; line-height:14px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/UGT1A3" title="UGT1A3"><span style="color:DeepSkyBlue">UGT1A3</span></a><br /><a href="/wiki/UGT1A9" title="UGT1A9"><span style="color:DeepSkyBlue">UGT1A9</span></a></span></div> <p><br /> </p><p><br /> </p> <div id="annotation_130x134" style="position:absolute; left:130px; top:134px; font-size:12px; font-size:12; line-height:14px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/CYP450" class="mw-redirect" title="CYP450"><span style="color:DeepSkyBlue">CYP450</span></a></span></div> <div id="annotation_296x134" style="position:absolute; left:296px; top:134px; font-size:12px; font-size:12; line-height:14px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/CYP450" class="mw-redirect" title="CYP450"><span style="color:DeepSkyBlue">CYP450</span></a></span></div> <p><br /> </p><p><br /> </p> <div id="annotation_16x206" style="position:absolute; left:16px; top:206px; font-size:12px; font-size:12; line-height:14px; text-align:right;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Catechol-O-methyltransferase" title="Catechol-O-methyltransferase"><span style="color:DeepSkyBlue">COMT</span></a></span></div> <div id="annotation_228x198" style="position:absolute; left:228px; top:198px; font-size:12px; font-size:12; line-height:14px; text-align:right;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/CYP450" class="mw-redirect" title="CYP450"><span style="color:DeepSkyBlue">CYP450</span></a></span></div> <div id="annotation_364x206" style="position:absolute; left:364px; top:206px; font-size:12px; font-size:12; line-height:14px; text-align:right;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Catechol-O-methyltransferase" title="Catechol-O-methyltransferase"><span style="color:DeepSkyBlue">COMT</span></a></span></div> <p><br /> </p><p><br /> </p> <div id="annotation_128x298" style="position:absolute; left:128px; top:298px; font-size:12px; font-size:12; line-height:14px; text-align:left;"><span style="background-color:transparent; color:inherit;">unidentified</span></div> <div id="annotation_226x300" style="position:absolute; left:226px; top:300px; font-size:12px; font-size:12; line-height:14px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/17%CE%B2-Hydroxysteroid_dehydrogenase" title="17β-Hydroxysteroid dehydrogenase"><span style="color:DeepSkyBlue">17β-HSD</span></a></span></div> <div id="annotation_296x298" style="position:absolute; left:296px; top:298px; font-size:12px; font-size:12; line-height:14px; text-align:right;"><span style="background-color:transparent; color:inherit;">unidentified</span></div></div> </div> </div> <div class="thumbcaption" style="clear:left"><div style="float:left;margin-right:0.5em"><span typeof="mw:File"><span title="The image above contains clickable links"><img alt="The image above contains clickable links" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/18px-Interactive_icon.svg.png" decoding="async" width="18" height="27" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/27px-Interactive_icon.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/36px-Interactive_icon.svg.png 2x" data-file-width="133" data-file-height="200" /></span></span></div><b>Description:</b> The <a href="/wiki/Metabolic_pathway" title="Metabolic pathway">metabolic pathways</a> involved in the <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> of <a href="/wiki/Estradiol" title="Estradiol">estradiol</a> and other <a href="/wiki/Natural_product" title="Natural product">natural</a> estrogens (e.g., <a href="/wiki/Estrone" title="Estrone">estrone</a>, <a href="/wiki/Estriol" title="Estriol">estriol</a>) in humans. In addition to the <a href="/wiki/Biotransformation" title="Biotransformation">metabolic transformations</a> shown in the diagram, <a href="/wiki/Conjugation_(biochemistry)" class="mw-redirect" title="Conjugation (biochemistry)">conjugation</a> (e.g., <a href="/wiki/Sulfation" title="Sulfation">sulfation</a> and <a href="/wiki/Glucuronidation" title="Glucuronidation">glucuronidation</a>) occurs in the case of estradiol and <a href="/wiki/Metabolite" title="Metabolite">metabolites</a> of estradiol that have one or more available <a href="/wiki/Hydroxyl_group" class="mw-redirect" title="Hydroxyl group">hydroxyl</a> (–OH) <a href="/wiki/Functional_group" title="Functional group">groups</a>. <b>Sources:</b> See template page.</div> </div> </div> </td></tr></tbody></table> <p><br /> </p> <div class="mw-heading mw-heading3"><h3 id="Excretion">Excretion</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estrogen&action=edit&section=23" title="Edit section: Excretion"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Estrogens are inactivated primarily by the <a href="/wiki/Kidney" title="Kidney">kidneys</a> and <a href="/wiki/Liver" title="Liver">liver</a> and excreted via the <a href="/wiki/Gastrointestinal_tract" title="Gastrointestinal tract">gastrointestinal tract</a><sup id="cite_ref-Trachsler_Thorn_Labhart_Bürgi_2012_p._530_101-0" class="reference"><a href="#cite_note-Trachsler_Thorn_Labhart_Bürgi_2012_p._530-101"><span class="cite-bracket">[</span>101<span class="cite-bracket">]</span></a></sup> in the form of <a href="/wiki/Conjugation_(biochemistry)" class="mw-redirect" title="Conjugation (biochemistry)">conjugates</a>, found in <a href="/wiki/Feces" title="Feces">feces</a>, <a href="/wiki/Bile" title="Bile">bile</a>, and <a href="/wiki/Urine" title="Urine">urine</a>.<sup id="cite_ref-Fuentes_Silveyra_2019_102-0" class="reference"><a href="#cite_note-Fuentes_Silveyra_2019-102"><span class="cite-bracket">[</span>102<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Medical_use">Medical use</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estrogen&action=edit&section=24" title="Edit section: Medical use"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogen (medication)</a></div> <p>Estrogens are used as <a href="/wiki/Medication" title="Medication">medications</a>, mainly in <a href="/wiki/Hormonal_contraception" title="Hormonal contraception">hormonal contraception</a>, <a href="/wiki/Hormone_replacement_therapy" title="Hormone replacement therapy">hormone replacement therapy</a>,<sup id="cite_ref-pmid16112947_103-0" class="reference"><a href="#cite_note-pmid16112947-103"><span class="cite-bracket">[</span>103<span class="cite-bracket">]</span></a></sup> and to treat gender dysphoria in <a href="/wiki/Trans_woman" title="Trans woman">transgender women</a> and other <a href="/wiki/Non-binary_gender" title="Non-binary gender">transfeminine individuals</a> as part of feminizing hormone therapy.<sup id="cite_ref-104" class="reference"><a href="#cite_note-104"><span class="cite-bracket">[</span>104<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=Estrogen&action=edit&section=25" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/List_of_estrogens" title="List of estrogens">List of estrogens</a></div> <p>The estrogen <a href="/wiki/Steroid" title="Steroid">steroid</a> hormones are <a href="/wiki/Estrane" title="Estrane">estrane</a> steroids.<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. (January 2025)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estrogen&action=edit&section=26" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Estradiol#History" title="Estradiol">Estradiol § History</a>, <a href="/wiki/Estrone#History" title="Estrone">Estrone § History</a>, and <a href="/wiki/Estrogen_(medication)#History" title="Estrogen (medication)">Estrogen (medication) § History</a></div> <p>In 1929, <a href="/wiki/Adolf_Butenandt" title="Adolf Butenandt">Adolf Butenandt</a> and <a href="/wiki/Edward_Adelbert_Doisy" title="Edward Adelbert Doisy">Edward Adelbert Doisy</a> independently isolated and purified estrone, the first estrogen to be discovered.<sup id="cite_ref-pmid15940278_105-0" class="reference"><a href="#cite_note-pmid15940278-105"><span class="cite-bracket">[</span>105<span class="cite-bracket">]</span></a></sup> Then, estriol and estradiol were discovered in 1930 and 1933, respectively. Shortly following their discovery, estrogens, both natural and synthetic, were introduced for medical use. Examples include <a href="/wiki/Estriol_glucuronide" title="Estriol glucuronide">estriol glucuronide</a> (<a href="/wiki/Emmenin" class="mw-redirect" title="Emmenin">Emmenin</a>, <a href="/wiki/Progynon" class="mw-redirect" title="Progynon">Progynon</a>), <a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">estradiol benzoate</a>, <a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">conjugated estrogens</a> (<a href="/wiki/Premarin" class="mw-redirect" title="Premarin">Premarin</a>), <a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">diethylstilbestrol</a>, and <a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">ethinylestradiol</a>. </p><p>The word estrogen derives from <a href="/wiki/Ancient_Greek" title="Ancient Greek">Ancient Greek</a>. It is derived from "oestros"<sup id="cite_ref-bioetymology_106-0" class="reference"><a href="#cite_note-bioetymology-106"><span class="cite-bracket">[</span>106<span class="cite-bracket">]</span></a></sup> (a periodic state of sexual activity in female mammals), and genos (generating).<sup id="cite_ref-bioetymology_106-1" class="reference"><a href="#cite_note-bioetymology-106"><span class="cite-bracket">[</span>106<span class="cite-bracket">]</span></a></sup> It was first published in the early 1920s and referenced as "oestrin".<sup id="cite_ref-107" class="reference"><a href="#cite_note-107"><span class="cite-bracket">[</span>107<span class="cite-bracket">]</span></a></sup> With the years, American English adapted the spelling of estrogen to fit with its phonetic pronunciation. </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=Estrogen&action=edit&section=27" 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="Etymology">Etymology</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estrogen&action=edit&section=28" title="Edit section: Etymology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The name <i>estrogen</i> is derived from the <a href="/wiki/Greek_language" title="Greek language">Greek</a> <span title="Ancient Greek (to 1453)-language text"><span lang="grc">οἶστρος</span></span> (<span title="Ancient Greek (to 1453)-language romanization"><i lang="grc-Latn">oîstros</i></span>), literally meaning "verve" or "inspiration" but figuratively sexual passion or desire,<sup id="cite_ref-108" class="reference"><a href="#cite_note-108"><span class="cite-bracket">[</span>108<span class="cite-bracket">]</span></a></sup> and the suffix <i><a href="https://en.wiktionary.org/wiki/-gen" class="extiw" title="wikt:-gen">-gen</a></i>, meaning "producer of". </p> <div class="mw-heading mw-heading3"><h3 id="Environment">Environment</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estrogen&action=edit&section=29" title="Edit section: Environment"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A range of synthetic and natural substances that possess estrogenic activity have been identified in the <a href="/wiki/Natural_environment" title="Natural environment">environment</a> and are referred to <a href="/wiki/Xenoestrogen" title="Xenoestrogen">xenoestrogens</a>.<sup id="cite_ref-pmid11258977_109-0" class="reference"><a href="#cite_note-pmid11258977-109"><span class="cite-bracket">[</span>109<span class="cite-bracket">]</span></a></sup> </p> <ul><li>Synthetic substances such as <a href="/wiki/Bisphenol_A" title="Bisphenol A">bisphenol A</a> as well as <a href="/wiki/Metalloestrogen" title="Metalloestrogen">metalloestrogens</a> (e.g., <a href="/wiki/Cadmium" title="Cadmium">cadmium</a>).</li> <li>Plant products with estrogenic activity are called <a href="/wiki/Phytoestrogen" title="Phytoestrogen">phytoestrogens</a> (e.g., <a href="/wiki/Coumestrol" title="Coumestrol">coumestrol</a>, <a href="/wiki/Daidzein" title="Daidzein">daidzein</a>, <a href="/wiki/Genistein" title="Genistein">genistein</a>, <a href="/wiki/Miroestrol" title="Miroestrol">miroestrol</a>).</li> <li>Those produced by fungi are known as <a href="/wiki/Mycoestrogens" class="mw-redirect" title="Mycoestrogens">mycoestrogens</a> (e.g., <a href="/wiki/Zearalenone" title="Zearalenone">zearalenone</a>).</li></ul> <p>Estrogens are among the wide range of <a href="/wiki/Endocrine_disruptor" title="Endocrine disruptor">endocrine-disrupting compounds</a> (EDCs) because they have high estrogenic potency. When an EDC makes its way into the environment, it may cause male reproductive dysfunction to wildlife and humans.<sup id="cite_ref-Wang_2008_12-1" class="reference"><a href="#cite_note-Wang_2008-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:1_13-1" class="reference"><a href="#cite_note-:1-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> The estrogen excreted from farm animals makes its way into fresh water systems.<sup id="cite_ref-pmid20977246_110-0" class="reference"><a href="#cite_note-pmid20977246-110"><span class="cite-bracket">[</span>110<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-111" class="reference"><a href="#cite_note-111"><span class="cite-bracket">[</span>111<span class="cite-bracket">]</span></a></sup> During the germination period of reproduction the fish are exposed to low levels of estrogen which may cause reproductive dysfunction to male fish.<sup id="cite_ref-pmid16203238_112-0" class="reference"><a href="#cite_note-pmid16203238-112"><span class="cite-bracket">[</span>112<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid16818244_113-0" class="reference"><a href="#cite_note-pmid16818244-113"><span class="cite-bracket">[</span>113<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Cosmetics">Cosmetics</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estrogen&action=edit&section=30" title="Edit section: Cosmetics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Some hair <a href="/wiki/Shampoo" title="Shampoo">shampoos</a> on the market include estrogens and placental extracts; others contain <a href="/wiki/Phytoestrogen" title="Phytoestrogen">phytoestrogens</a>. In 1998, there were case reports of four prepubescent African-American girls developing breasts after exposure to these shampoos.<sup id="cite_ref-114" class="reference"><a href="#cite_note-114"><span class="cite-bracket">[</span>114<span class="cite-bracket">]</span></a></sup> In 1993, the FDA determined that not all <a href="/wiki/Over-the-counter_drug" title="Over-the-counter drug">over-the-counter</a> topically applied hormone-containing drug products for human use are <a href="/wiki/Generally_recognized_as_safe_and_effective" title="Generally recognized as safe and effective">generally recognized as safe and effective</a> and are misbranded. An accompanying proposed rule deals with cosmetics, concluding that any use of natural estrogens in a cosmetic product makes the product an unapproved new drug and that any cosmetic using the term "hormone" in the text of its labeling or in its ingredient statement makes an implied drug claim, subjecting such a product to regulatory action.<sup id="cite_ref-FDA_cosmetics_115-0" class="reference"><a href="#cite_note-FDA_cosmetics-115"><span class="cite-bracket">[</span>115<span class="cite-bracket">]</span></a></sup> </p><p>In addition to being considered misbranded drugs, products claiming to contain placental extract may also be deemed to be misbranded cosmetics if the extract has been prepared from placentas from which the hormones and other biologically active substances have been removed and the extracted substance consists principally of protein. The FDA recommends that this substance be identified by a name other than "placental extract" and describing its composition more accurately because consumers associate the name "placental extract" with a therapeutic use of some biological activity.<sup id="cite_ref-FDA_cosmetics_115-1" class="reference"><a href="#cite_note-FDA_cosmetics-115"><span class="cite-bracket">[</span>115<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estrogen&action=edit&section=31" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/List_of_steroid_abbreviations" title="List of steroid abbreviations">List of steroid abbreviations</a></li> <li><a href="/wiki/Breastfeeding_and_fertility" class="mw-redirect" title="Breastfeeding and fertility">Breastfeeding and fertility</a></li> <li><a href="/wiki/Vasoprotective" title="Vasoprotective">Vasoprotective</a></li></ul> <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=Estrogen&action=edit&section=32" 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 reflist-columns references-column-width" style="column-width: 32em;"> <ol class="references"> <li id="cite_note-Huether-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Huether_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Huether_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Huether_1-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFHuetherMcCance2019" class="citation book cs1">Huether SE, McCance KL (2019). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=oF2yDwAAQBAJ&pg=PA767"><i>Understanding Pathophysiology</i></a>. Elsevier Health Sciences. p. 767. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-32-367281-8" title="Special:BookSources/978-0-32-367281-8"><bdi>978-0-32-367281-8</bdi></a>. <q>Estrogen is a generic term for any of three similar hormones derived from cholesterol: estradiol, estrone, and estriol.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Understanding+Pathophysiology&rft.pages=767&rft.pub=Elsevier+Health+Sciences&rft.date=2019&rft.isbn=978-0-32-367281-8&rft.aulast=Huether&rft.aufirst=SE&rft.au=McCance%2C+KL&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DoF2yDwAAQBAJ%26pg%3DPA767&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstrogen" class="Z3988"></span></span> </li> <li id="cite_note-Satoskar-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-Satoskar_2-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSatoskarRegeBhandarkar2017" class="citation book cs1">Satoskar RS, Rege N, Bhandarkar SD (2017). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=f9LQDwAAQBAJ&pg=PA943"><i>Pharmacology and Pharmacotherapeutics</i></a>. Elsevier Health Sciences. p. 943. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-8-13-124941-3" title="Special:BookSources/978-8-13-124941-3"><bdi>978-8-13-124941-3</bdi></a>. <q>The natural estrogens are steroids. However, typical estrogenic activity is also shown by chemicals which are not steroids. Hence, the term 'estrogen' is used as a generic term to describe all the compounds having estrogenic activity.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Pharmacology+and+Pharmacotherapeutics&rft.pages=943&rft.pub=Elsevier+Health+Sciences&rft.date=2017&rft.isbn=978-8-13-124941-3&rft.aulast=Satoskar&rft.aufirst=RS&rft.au=Rege%2C+N&rft.au=Bhandarkar%2C+SD&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Df9LQDwAAQBAJ%26pg%3DPA943&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstrogen" class="Z3988"></span></span> </li> <li id="cite_note-Delgado-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-Delgado_3-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDelgadoLopez-Ojeda2021" class="citation book cs1">Delgado BJ, Lopez-Ojeda W (20 December 2021). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/books/NBK538260/">"Estrogen"</a>. <i>StatPearls [Internet]</i>. StatPearls Publishing. <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/30855848">30855848</a>. <q>Estrogen is a steroid hormone associated with the female reproductive organs and is responsible for the development of female sexual characteristics. Estrogen is often referred to as estrone, estradiol, and estriol. ... Synthetic estrogen is also available for clinical use, designed to increase absorption and effectiveness by altering the estrogen chemical structure for topical or oral administration. Synthetic steroid estrogens include ethinyl estradiol, estradiol valerate, estropipate, conjugate esterified estrogen, and quinestrol.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Estrogen&rft.btitle=StatPearls+%5BInternet%5D&rft.pub=StatPearls+Publishing&rft.date=2021-12-20&rft_id=info%3Apmid%2F30855848&rft.aulast=Delgado&rft.aufirst=BJ&rft.au=Lopez-Ojeda%2C+W&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fbooks%2FNBK538260%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstrogen" class="Z3988"></span></span> </li> <li id="cite_note-pmid7083198-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid7083198_4-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRyan1982" class="citation journal cs1">Ryan KJ (August 1982). 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"Estrogens in insects". <i>Cellular and Molecular Life Sciences</i>. <b>40</b> (9): <span class="nowrap">942–</span>944. <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%2FBF01946450">10.1007/BF01946450</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:31950471">31950471</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Cellular+and+Molecular+Life+Sciences&rft.atitle=Estrogens+in+insects&rft.volume=40&rft.issue=9&rft.pages=%3Cspan+class%3D%22nowrap%22%3E942-%3C%2Fspan%3E944&rft.date=2005-09&rft_id=info%3Adoi%2F10.1007%2FBF01946450&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A31950471%23id-name%3DS2CID&rft.aulast=Mechoulam&rft.aufirst=R&rft.au=Brueggemeier%2C+RW&rft.au=Denlinger%2C+DL&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstrogen" class="Z3988"></span></span> </li> <li id="cite_note-Burger2002-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-Burger2002_6-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBurger2002" class="citation journal cs1">Burger HG (April 2002). <a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0015-0282%2802%2902985-0">"Androgen production in women"</a>. <i>Fertility and Sterility</i>. <b>77</b> (Suppl 4): <span class="nowrap">S3 –</span> <span class="nowrap">S5</span>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0015-0282%2802%2902985-0">10.1016/S0015-0282(02)02985-0</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/12007895">12007895</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Fertility+and+Sterility&rft.atitle=Androgen+production+in+women&rft.volume=77&rft.issue=Suppl+4&rft.pages=%3Cspan+class%3D%22nowrap%22%3ES3+-%3C%2Fspan%3E+%3Cspan+class%3D%22nowrap%22%3ES5%3C%2Fspan%3E&rft.date=2002-04&rft_id=info%3Adoi%2F10.1016%2FS0015-0282%2802%2902985-0&rft_id=info%3Apmid%2F12007895&rft.aulast=Burger&rft.aufirst=HG&rft_id=https%3A%2F%2Fdoi.org%2F10.1016%252FS0015-0282%252802%252902985-0&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstrogen" class="Z3988"></span></span> </li> <li id="cite_note-pmid11403894-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid11403894_7-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLombardiZarrilliColaoPaesano2001" class="citation journal cs1">Lombardi G, Zarrilli S, Colao A, Paesano L, Di Somma C, Rossi F, et al. 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(18 March 2016). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4797181">"Sex-specific genetic effects associated with pigmentation, sensitivity to sunlight, and melanoma in a population of Spanish origin"</a>. <i>Biology of Sex Differences</i>. <b>7</b> (1): 17. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1186%2Fs13293-016-0070-1">10.1186/s13293-016-0070-1</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4797181">4797181</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/26998216">26998216</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Biology+of+Sex+Differences&rft.atitle=Sex-specific+genetic+effects+associated+with+pigmentation%2C+sensitivity+to+sunlight%2C+and+melanoma+in+a+population+of+Spanish+origin&rft.volume=7&rft.issue=1&rft.pages=17&rft.date=2016-03-18&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4797181%23id-name%3DPMC&rft_id=info%3Apmid%2F26998216&rft_id=info%3Adoi%2F10.1186%2Fs13293-016-0070-1&rft.aulast=Hernando&rft.aufirst=B&rft.au=Ibarrola-Villava%2C+M&rft.au=Fernandez%2C+LP&rft.au=Pe%C3%B1a-Chilet%2C+M&rft.au=Llorca-Carde%C3%B1osa%2C+M&rft.au=Oltra%2C+SS&rft.au=Alonso%2C+S&rft.au=Boyano%2C+MD&rft.au=Martinez-Cadenas%2C+C&rft.au=Ribas%2C+G&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4797181&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstrogen" class="Z3988"></span> "The results of this study suggest that there are indeed sex-specific genetic effects in human pigmentation, with larger effects for darker pigmentation in females compared to males. A plausible cause might be the differentially expressed melanogenic genes in females due to higher oestrogen levels. These sex-specific genetic effects would help explain the presence of darker eye and skin pigmentation in females, as well as the well-known higher melanoma risk displayed by males."</span> </li> <li id="cite_note-pmid15298854-42"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid15298854_42-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMassaroMassaro2004" class="citation journal cs1">Massaro D, Massaro GD (December 2004). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20190225225427/http://pdfs.semanticscholar.org/65aa/5f698c0b57e4d3746dace1af255260ebeae5.pdf">"Estrogen regulates pulmonary alveolar formation, loss, and regeneration in mice"</a> <span class="cs1-format">(PDF)</span>. <i>American Journal of Physiology. 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Elsevier Health Sciences. p. 413. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7020-3489-3" title="Special:BookSources/978-0-7020-3489-3"><bdi>978-0-7020-3489-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Anatomy+and+Physiology+for+Midwives%2C+with+Pageburst+online+access%2C3%3A+Anatomy+and+Physiology+for+Midwives&rft.pages=413&rft.pub=Elsevier+Health+Sciences&rft.date=2011&rft.isbn=978-0-7020-3489-3&rft.aulast=Coad&rft.aufirst=J&rft.au=Dunstall%2C+M&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DOmSKoYD-iW0C%26pg%3DPA413&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstrogen" class="Z3988"></span></span> </li> <li id="cite_note-HaslamOsuch2006-53"><span class="mw-cite-backlink"><b><a href="#cite_ref-HaslamOsuch2006_53-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHaslamOsuch2006" class="citation book cs1">Haslam SZ, Osuch JR (1 January 2006). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=wGaKtDw50K0C&pg=PA69"><i>Hormones and Breast Cancer in Post-Menopausal Women</i></a>. 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Thieme. pp. 305–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-13-149521-1" title="Special:BookSources/978-3-13-149521-1"><bdi>978-3-13-149521-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Color+Atlas+of+Physiology&rft.pages=305-&rft.pub=Thieme&rft.date=2011-01-01&rft.isbn=978-3-13-149521-1&rft.aulast=Silbernagl&rft.aufirst=S&rft.au=Despopoulos%2C+A&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DWyuCGhv4kvwC%26pg%3DPA305&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstrogen" class="Z3988"></span></span> </li> <li id="cite_note-Fadem2007-55"><span class="mw-cite-backlink"><b><a href="#cite_ref-Fadem2007_55-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFadem2007" class="citation book cs1">Fadem B (2007). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=d-MxROzDPgcC&pg=PA445"><i>High-yield Comprehensive USMLE Step 1 Review</i></a>. Lippincott Williams & Wilkins. pp. 445–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7817-7427-7" title="Special:BookSources/978-0-7817-7427-7"><bdi>978-0-7817-7427-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=High-yield+Comprehensive+USMLE+Step+1+Review&rft.pages=445-&rft.pub=Lippincott+Williams+%26+Wilkins&rft.date=2007&rft.isbn=978-0-7817-7427-7&rft.aulast=Fadem&rft.aufirst=B&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dd-MxROzDPgcC%26pg%3DPA445&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstrogen" class="Z3988"></span></span> </li> <li id="cite_note-Blackburn2014-56"><span class="mw-cite-backlink"><b><a href="#cite_ref-Blackburn2014_56-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBlackburn2014" class="citation book cs1">Blackburn S (14 April 2014). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=RNLsAwAAQBAJ&pg=PA146"><i>Maternal, Fetal, & Neonatal Physiology</i></a>. Elsevier Health Sciences. pp. 146–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-323-29296-2" title="Special:BookSources/978-0-323-29296-2"><bdi>978-0-323-29296-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Maternal%2C+Fetal%2C+%26+Neonatal+Physiology&rft.pages=146-&rft.pub=Elsevier+Health+Sciences&rft.date=2014-04-14&rft.isbn=978-0-323-29296-2&rft.aulast=Blackburn&rft.aufirst=S&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DRNLsAwAAQBAJ%26pg%3DPA146&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstrogen" class="Z3988"></span></span> </li> <li id="cite_note-IIIBarbieri2013-57"><span class="mw-cite-backlink"><b><a href="#cite_ref-IIIBarbieri2013_57-0">^</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=PA236"><i>Yen and Jaffe's Reproductive Endocrinology</i></a>. Elsevier Health Sciences. pp. 236–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4557-2758-2" title="Special:BookSources/978-1-4557-2758-2"><bdi>978-1-4557-2758-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Yen+and+Jaffe%27s+Reproductive+Endocrinology&rft.pages=236-&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%3DPA236&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstrogen" class="Z3988"></span></span> </li> <li id="cite_note-WilsonNizet2015-58"><span class="mw-cite-backlink"><b><a href="#cite_ref-WilsonNizet2015_58-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWilsonNizetMaldonadoRemington2015" class="citation book cs1">Wilson CB, Nizet V, Maldonado Y, Remington JS, Klein JO (24 February 2015). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=VuZ1BwAAQBAJ&pg=PA190"><i>Remington and Klein's Infectious Diseases of the Fetus and Newborn Infant</i></a>. 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Retrieved <span class="nowrap">4 June</span> 2008</span>.</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=Preschool+Puberty%2C+and+a+Search+for+the+Causes&rft.date=2006-10-17&rft.aulast=Sanghavi&rft.aufirst=DM&rft_id=https%3A%2F%2Fwww.nytimes.com%2F2006%2F10%2F17%2Fscience%2F17puberty.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstrogen" class="Z3988"></span></span> </li> <li id="cite_note-FDA_cosmetics-115"><span class="mw-cite-backlink">^ <a href="#cite_ref-FDA_cosmetics_115-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-FDA_cosmetics_115-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFDA1995" class="citation web cs1">FDA (February 1995). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20071014014542/https://www.fda.gov/ora/inspect_ref/igs/cosmet.html">"Products containing estrogenic hormones, placental extract or vitamins"</a>. <i>Guide to Inspections of Cosmetic Product Manufacturers</i>. Archived from <a rel="nofollow" class="external text" href="https://www.fda.gov/ora/inspect_ref/igs/cosmet.html">the original</a> on 14 October 2007<span class="reference-accessdate">. Retrieved <span class="nowrap">24 October</span> 2006</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Guide+to+Inspections+of+Cosmetic+Product+Manufacturers&rft.atitle=Products+containing+estrogenic+hormones%2C+placental+extract+or+vitamins&rft.date=1995-02&rft.au=FDA&rft_id=https%3A%2F%2Fwww.fda.gov%2Fora%2Finspect_ref%2Figs%2Fcosmet.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstrogen" class="Z3988"></span></span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estrogen&action=edit&section=33" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>Nussey and Whitehead: <i><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/books/bv.fcgi?call=bv.View..ShowTOC&rid=endocrin.TOC&depth=10">Endocrinology, an integrated approach</a></i>, Taylor and Francis 2001. Free online textbook.</li></ul> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1236075235">.mw-parser-output .navbox{box-sizing:border-box;border:1px solid #a2a9b1;width:100%;clear:both;font-size:88%;text-align:center;padding:1px;margin:1em auto 0}.mw-parser-output .navbox .navbox{margin-top:0}.mw-parser-output .navbox+.navbox,.mw-parser-output .navbox+.navbox-styles+.navbox{margin-top:-1px}.mw-parser-output .navbox-inner,.mw-parser-output .navbox-subgroup{width:100%}.mw-parser-output .navbox-group,.mw-parser-output .navbox-title,.mw-parser-output .navbox-abovebelow{padding:0.25em 1em;line-height:1.5em;text-align:center}.mw-parser-output .navbox-group{white-space:nowrap;text-align:right}.mw-parser-output .navbox,.mw-parser-output .navbox-subgroup{background-color:#fdfdfd}.mw-parser-output .navbox-list{line-height:1.5em;border-color:#fdfdfd}.mw-parser-output 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estradiol">Pharmacokinetics of estradiol</a></li> <li><a class="mw-selflink selflink">Estrogen (as a hormone)</a></li> <li><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogen (as a medication)</a></li> <li><a href="/wiki/Hormone_replacement_therapy" title="Hormone replacement therapy">Menopausal hormone therapy</a></li> <li><a href="/wiki/Feminizing_hormone_therapy" title="Feminizing hormone therapy">Feminizing hormone therapy</a></li> <li><a href="/wiki/Estradiol-containing_birth_control_pill" title="Estradiol-containing birth control pill">Estradiol-containing birth control pill</a></li> <li><a href="/wiki/Combined_injectable_birth_control" title="Combined injectable birth control">Combined injectable birth control</a></li> <li><a href="/wiki/High-dose_estrogen" class="mw-redirect" title="High-dose estrogen">High-dose estrogen</a></li> <li><a href="/wiki/Hydroxylation_of_estradiol" title="Hydroxylation of estradiol">Hydroxylation of estradiol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Estrogen_ester" title="Estrogen ester">Esters</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/Estradiol_acetate" title="Estradiol acetate">Estradiol acetate</a></li> <li><a href="/wiki/Estradiol_acetylsalicylate" title="Estradiol acetylsalicylate">Estradiol acetylsalicylate</a></li> <li><a href="/wiki/Estradiol_anthranilate" title="Estradiol anthranilate">Estradiol anthranilate</a></li> <li><a href="/wiki/Estradiol_benzoate_butyrate" title="Estradiol benzoate butyrate">Estradiol benzoate butyrate</a></li> <li><a href="/wiki/Estradiol_benzoate_cyclooctenyl_ether" title="Estradiol benzoate cyclooctenyl ether">Estradiol benzoate cyclooctenyl ether</a></li> <li><a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">Estradiol benzoate</a></li> <li><a href="/wiki/Estradiol_butyrylacetate" title="Estradiol butyrylacetate">Estradiol butyrylacetate</a></li> <li><a href="/wiki/Estradiol_cyclooctyl_acetate" title="Estradiol cyclooctyl acetate">Estradiol cyclooctyl acetate</a></li> <li><a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">Estradiol cypionate</a></li> <li><a href="/wiki/Estradiol_decanoate" title="Estradiol decanoate">Estradiol decanoate</a></li> <li><a href="/wiki/Estradiol_diacetate" title="Estradiol diacetate">Estradiol diacetate</a></li> <li><a href="/wiki/Estradiol_dibutyrate" title="Estradiol dibutyrate">Estradiol dibutyrate</a></li> <li><a href="/wiki/Estradiol_dienantate" title="Estradiol dienantate">Estradiol dienantate</a></li> <li><a href="/wiki/Estradiol_dipropionate" title="Estradiol dipropionate">Estradiol dipropionate</a></li> <li><a href="/wiki/Estradiol_distearate" title="Estradiol distearate">Estradiol distearate</a></li> <li><a href="/wiki/Estradiol_disulfate" title="Estradiol disulfate">Estradiol disulfate</a></li> <li><a href="/wiki/Estradiol_diundecylate" title="Estradiol diundecylate">Estradiol diundecylate</a></li> <li><a href="/wiki/Estradiol_diundecylenate" title="Estradiol diundecylenate">Estradiol diundecylenate</a></li> <li><a href="/wiki/Estradiol_enantate" title="Estradiol enantate">Estradiol enantate</a></li> <li><a href="/wiki/Estradiol_furoate" title="Estradiol furoate">Estradiol furoate</a></li> <li><a href="/wiki/Estradiol_glucuronide" title="Estradiol glucuronide">Estradiol glucuronide</a></li> <li><a href="/wiki/Estradiol_hemisuccinate" title="Estradiol hemisuccinate">Estradiol hemisuccinate</a></li> <li><a href="/wiki/Estradiol_hexahydrobenzoate" title="Estradiol hexahydrobenzoate">Estradiol hexahydrobenzoate</a></li> <li><a href="/wiki/Estradiol_monopropionate" title="Estradiol monopropionate">Estradiol monopropionate</a></li> <li><a href="/wiki/Estradiol_mustard" title="Estradiol mustard">Estradiol mustard</a></li> <li><a href="/wiki/Estradiol_palmitate" title="Estradiol palmitate">Estradiol palmitate</a></li> <li><a href="/wiki/Estradiol_phenylpropionate" title="Estradiol phenylpropionate">Estradiol phenylpropionate</a></li> <li><a href="/wiki/Estradiol_phosphate" title="Estradiol phosphate">Estradiol phosphate</a></li> <li><a href="/wiki/Estradiol_pivalate" title="Estradiol pivalate">Estradiol pivalate</a></li> <li><a href="/wiki/Estradiol_propoxyphenylpropionate" title="Estradiol propoxyphenylpropionate">Estradiol propoxyphenylpropionate</a></li> <li><a href="/wiki/Estradiol_salicylate" title="Estradiol salicylate">Estradiol salicylate</a></li> <li><a href="/wiki/Estradiol_stearate" title="Estradiol stearate">Estradiol stearate</a></li> <li><a href="/wiki/Estradiol_sulfamate" title="Estradiol sulfamate">Estradiol sulfamate</a></li> <li><a href="/wiki/Estradiol_sulfate" title="Estradiol sulfate">Estradiol sulfate</a></li> <li><a href="/wiki/Estradiol_undecylate" title="Estradiol undecylate">Estradiol undecylate</a></li> <li><a href="/wiki/Estradiol_undecylenate" title="Estradiol undecylenate">Estradiol undecylenate</a></li> <li><a href="/wiki/Estradiol_valerate" title="Estradiol valerate">Estradiol valerate</a></li> <li><a href="/wiki/Estramustine_phosphate" title="Estramustine phosphate">Estramustine phosphate (estradiol normustine phosphate)</a></li> <li><a href="/wiki/Estrogen_ester" title="Estrogen ester">Estrogen ester</a></li> <li><a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">Polyestradiol phosphate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">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/Estrone_(medication)" title="Estrone (medication)">Estrone</a></li> <li><a href="/wiki/Estriol_(medication)" title="Estriol (medication)">Estriol</a></li> <li><a href="/wiki/Estetrol_(medication)" title="Estetrol (medication)">Estetrol</a></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a></li> <li><a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a></li> <li><a href="/wiki/Esterified_estrogens" title="Esterified estrogens">Esterified estrogens</a></li> <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> </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="Hormones57" 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:Hormones" title="Template:Hormones"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Hormones" title="Template talk:Hormones"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Hormones" title="Special:EditPage/Template:Hormones"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Hormones57" style="font-size:114%;margin:0 4em"><a href="/wiki/Hormone" title="Hormone">Hormones</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Endocrine_gland" title="Endocrine gland">Endocrine<br />glands</a></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 id="Hypothalamic–pituitary250" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hypothalamic%E2%80%93pituitary_hormone" title="Hypothalamic–pituitary hormone">Hypothalamic–<br />pituitary</a></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:1%"><a href="/wiki/Hypothalamus" title="Hypothalamus">Hypothalamus</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Gonadotropin-releasing_hormone" title="Gonadotropin-releasing hormone">GnRH</a></li> <li><a href="/wiki/Thyrotropin-releasing_hormone" title="Thyrotropin-releasing hormone">TRH</a></li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/Corticotropin-releasing_hormone" title="Corticotropin-releasing hormone">CRH</a></li> <li><a href="/wiki/Growth_hormone%E2%80%93releasing_hormone" title="Growth hormone–releasing hormone">GHRH</a></li> <li><a href="/wiki/Somatostatin" title="Somatostatin">Somatostatin (GHIH)</a></li> <li><a href="/wiki/Melanin_concentrating_hormone" class="mw-redirect" title="Melanin concentrating hormone">MCH</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Posterior_pituitary" title="Posterior pituitary">Posterior pituitary</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Oxytocin" title="Oxytocin">Oxytocin</a></li> <li><a href="/wiki/Vasopressin" title="Vasopressin">Vasopressin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Anterior_pituitary" title="Anterior pituitary">Anterior pituitary</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Follicle-stimulating_hormone" title="Follicle-stimulating hormone">FSH</a></li> <li><a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone">LH</a></li> <li><a href="/wiki/Thyroid-stimulating_hormone" title="Thyroid-stimulating hormone">TSH</a></li> <li><a href="/wiki/Prolactin" title="Prolactin">Prolactin</a></li> <li><a href="/wiki/Proopiomelanocortin" title="Proopiomelanocortin">POMC</a> <ul><li><a href="/wiki/Corticotropin-like_intermediate_peptide" title="Corticotropin-like intermediate peptide">CLIP</a></li> <li><a href="/wiki/Adrenocorticotropic_hormone" title="Adrenocorticotropic hormone">ACTH</a></li> <li><a href="/wiki/Melanocyte-stimulating_hormone" title="Melanocyte-stimulating hormone">MSH</a></li> <li><a href="/wiki/Endorphins" title="Endorphins">Endorphins</a></li> <li><a href="/wiki/Lipotropin" title="Lipotropin">Lipotropin</a></li></ul></li> <li><a href="/wiki/Growth_hormone" title="Growth hormone">GH</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hypothalamic%E2%80%93pituitary%E2%80%93adrenal_axis" title="Hypothalamic–pituitary–adrenal axis">Adrenal axis</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adrenal_gland#Adrenal_cortex" title="Adrenal gland">Adrenal cortex</a> <ul><li><a href="/wiki/Aldosterone" title="Aldosterone">Aldosterone</a></li> <li><a href="/wiki/Cortisol" title="Cortisol">Cortisol</a></li> <li><a href="/wiki/Cortisone" title="Cortisone">Cortisone</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA-S</a></li> <li><a href="/wiki/Androstenedione" title="Androstenedione">Androstenedione</a></li></ul></li> <li><a href="/wiki/Adrenal_gland#Adrenal_medulla" title="Adrenal gland">Adrenal medulla</a> <ul><li><a href="/wiki/Adrenaline" title="Adrenaline">Adrenaline</a></li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Thyroid" title="Thyroid">Thyroid</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Thyroid_hormones" title="Thyroid hormones">Thyroid hormones</a> <ul><li><a href="/wiki/Triiodothyronine" title="Triiodothyronine">T<sub>3</sub></a></li> <li><a href="/wiki/Thyroxine" title="Thyroxine">T<sub>4</sub></a></li></ul></li> <li><a href="/wiki/Calcitonin" title="Calcitonin">Calcitonin</a></li> <li><a href="/wiki/Hypothalamic%E2%80%93pituitary%E2%80%93thyroid_axis" title="Hypothalamic–pituitary–thyroid axis">Thyroid axis</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Parathyroid_gland" title="Parathyroid gland">Parathyroid</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Parathyroid_hormone" title="Parathyroid hormone">PTH</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hypothalamic%E2%80%93pituitary%E2%80%93gonadal_axis" title="Hypothalamic–pituitary–gonadal axis">Gonadal axis</a></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:1%"><a href="/wiki/Testicle" title="Testicle">Testis</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Testosterone" title="Testosterone">Testosterone</a></li> <li><a href="/wiki/Anti-M%C3%BCllerian_hormone" title="Anti-Müllerian hormone">AMH</a></li> <li><a href="/wiki/Activin_and_inhibin" title="Activin and inhibin">Inhibin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ovary" title="Ovary">Ovary</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Activin_and_inhibin" title="Activin and inhibin">Activin</a></li> <li><a href="/wiki/Activin_and_inhibin" title="Activin and inhibin">Inhibin</a></li> <li><a href="/wiki/Relaxin" title="Relaxin">Relaxin</a></li> <li><a href="/wiki/Gonadotropin_surge-attenuating_factor" title="Gonadotropin surge-attenuating factor">GnSAF</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Placenta" title="Placenta">Placenta</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Human_chorionic_gonadotropin" title="Human chorionic gonadotropin">hCG</a></li> <li><a href="/wiki/Human_placental_lactogen" title="Human placental lactogen">HPL</a></li> <li><a class="mw-selflink selflink">Estrogen</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pancreas" title="Pancreas">Pancreas</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Glucagon" title="Glucagon">Glucagon</a></li> <li><a href="/wiki/Insulin" title="Insulin">Insulin</a></li> <li><a href="/wiki/Amylin" title="Amylin">Amylin</a></li> <li><a href="/wiki/Somatostatin" title="Somatostatin">Somatostatin</a></li> <li><a href="/wiki/Pancreatic_polypeptide" title="Pancreatic polypeptide">Pancreatic polypeptide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pineal_gland" title="Pineal gland">Pineal gland</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Melatonin" title="Melatonin">Melatonin</a></li> <li><a href="/wiki/N,N-Dimethyltryptamine" title="N,N-Dimethyltryptamine">N,N-Dimethyltryptamine</a></li> <li><a href="/wiki/5-Methoxy-N,N-dimethyltryptamine" class="mw-redirect" title="5-Methoxy-N,N-dimethyltryptamine">5-Methoxy-N,N-dimethyltryptamine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</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:1%"><a href="/wiki/Thymus" title="Thymus">Thymus</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Thymosin" title="Thymosin">Thymosins</a> <ul><li><a href="/wiki/Thymosin_%CE%B11" title="Thymosin α1">Thymosin α1</a></li> <li><a href="/wiki/Beta_thymosin" class="mw-redirect" title="Beta thymosin">Beta thymosins</a></li></ul></li> <li><a href="/wiki/Thymopoietin" title="Thymopoietin">Thymopoietin</a></li> <li><a href="/wiki/Thymulin" title="Thymulin">Thymulin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Digestion" title="Digestion">Digestive system</a></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:1%"><a href="/wiki/Stomach" title="Stomach">Stomach</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Gastrin" title="Gastrin">Gastrin</a></li> <li><a href="/wiki/Ghrelin" title="Ghrelin">Ghrelin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Duodenum" title="Duodenum">Duodenum</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cholecystokinin" title="Cholecystokinin">CCK</a></li> <li><a href="/wiki/Gastric_inhibitory_polypeptide" title="Gastric inhibitory polypeptide">GIP</a></li> <li><a href="/wiki/Secretin" title="Secretin">Secretin</a></li> <li><a href="/wiki/Motilin" title="Motilin">Motilin</a></li> <li><a href="/wiki/Vasoactive_intestinal_peptide" title="Vasoactive intestinal peptide">VIP</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ileum" title="Ileum">Ileum</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Enteroglucagon" title="Enteroglucagon">Enteroglucagon</a></li> <li><a href="/wiki/Peptide_YY" title="Peptide YY">Peptide YY</a></li> <li><a href="/wiki/Glucagon-like_peptide-1" title="Glucagon-like peptide-1">GLP-1</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Liver" title="Liver">Liver</a>/other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Insulin-like_growth_factor" title="Insulin-like growth factor">Insulin-like growth factor</a> <ul><li><a href="/wiki/Insulin-like_growth_factor_1" title="Insulin-like growth factor 1">IGF-1</a></li> <li><a href="/wiki/Insulin-like_growth_factor_2" title="Insulin-like growth factor 2">IGF-2</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Adipose_tissue" title="Adipose tissue">Adipose tissue</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Leptin" title="Leptin">Leptin</a></li> <li><a href="/wiki/Adiponectin" title="Adiponectin">Adiponectin</a></li> <li><a href="/wiki/Resistin" title="Resistin">Resistin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Human_skeleton" title="Human skeleton">Skeleton</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Osteocalcin" title="Osteocalcin">Osteocalcin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Kidney" title="Kidney">Kidney</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Renin" title="Renin">Renin</a></li> <li><a href="/wiki/Erythropoietin" title="Erythropoietin">EPO</a></li> <li><a href="/wiki/Calcitriol" title="Calcitriol">Calcitriol</a></li> <li><a href="/wiki/Prostaglandin" title="Prostaglandin">Prostaglandin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Heart" title="Heart">Heart</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Natriuretic_peptide" title="Natriuretic peptide">Natriuretic peptide</a> <ul><li><a href="/wiki/Atrial_natriuretic_peptide" title="Atrial natriuretic peptide">ANP</a></li> <li><a href="/wiki/Brain_natriuretic_peptide_32" title="Brain natriuretic peptide 32">BNP</a></li></ul></li></ul> </div></td></tr></tbody></table><div></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="Endogenous_steroids141" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Steroid_hormones" title="Template:Steroid hormones"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Steroid_hormones" title="Template talk:Steroid hormones"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Steroid_hormones" title="Special:EditPage/Template:Steroid hormones"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Endogenous_steroids141" style="font-size:114%;margin:0 4em"><a href="/wiki/Endogenous" class="mw-redirect" title="Endogenous">Endogenous</a> <a href="/wiki/Steroid" title="Steroid">steroids</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">Precursors</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></li> <li><a href="/wiki/22R-Hydroxycholesterol" title="22R-Hydroxycholesterol">22<i>R</i>-Hydroxycholesterol</a></li> <li><a href="/wiki/20%CE%B1,22R-Dihydroxycholesterol" title="20α,22R-Dihydroxycholesterol">20α,22<i>R</i>-Dihydroxycholesterol</a></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a></li> <li><a href="/w/index.php?title=11%CE%B2-Hydroxypregnenolone&action=edit&redlink=1" class="new" title="11β-Hydroxypregnenolone (page does not exist)">11β-Hydroxypregnenolone</a></li> <li><a href="/wiki/17%CE%B1-Hydroxypregnenolone" title="17α-Hydroxypregnenolone">17α-Hydroxypregnenolone</a></li> <li><a href="/wiki/21-Hydroxypregnenolone" title="21-Hydroxypregnenolone">21-Hydroxypregnenolone</a></li> <li><a href="/w/index.php?title=17%CE%B1,21-Dihydroxypregnenolone&action=edit&redlink=1" class="new" title="17α,21-Dihydroxypregnenolone (page does not exist)">17α,21-Dihydroxypregnenolone</a></li> <li><a href="/w/index.php?title=11%CE%B2,17%CE%B1,21-Trihydroxypregnenolone&action=edit&redlink=1" class="new" title="11β,17α,21-Trihydroxypregnenolone (page does not exist)">11β,17α,21-Trihydroxypregnenolone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Corticosteroid" title="Corticosteroid">Corticosteroids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Glucocorticoid" title="Glucocorticoid">Glucocorticoids</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Tetrahydrocorticosterone" title="Tetrahydrocorticosterone">3α,5α-Tetrahydrocorticosterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydrocorticosterone" title="5α-Dihydrocorticosterone">5α-Dihydrocorticosterone</a></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone</a></li> <li><a href="/wiki/11-Deoxycortisol" title="11-Deoxycortisol">11-Deoxycortisol</a></li> <li><a href="/wiki/11-Ketoprogesterone" title="11-Ketoprogesterone">11-Ketoprogesterone</a></li> <li><a href="/wiki/21-Deoxycortisol" title="21-Deoxycortisol">21-Deoxycortisol</a></li> <li><a href="/wiki/21-Deoxycortisone" title="21-Deoxycortisone">21-Deoxycortisone</a></li> <li><a href="/wiki/Corticosterone" title="Corticosterone">Corticosterone</a></li> <li><a href="/wiki/Cortisol" title="Cortisol">Cortisol</a></li> <li><a href="/wiki/Cortisone" title="Cortisone">Cortisone</a></li> <li><a href="/wiki/17%CE%B1-Hydroxypregnenolone" title="17α-Hydroxypregnenolone">17α-Hydroxypregnenolone</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone</a></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li></ul> <ul><li><i>Metabolites:</i> <a href="/wiki/5%CE%B1-Dihydrocortisol" title="5α-Dihydrocortisol">5α-Dihydrocortisol</a></li> <li><a href="/w/index.php?title=3%CE%B1,5%CE%B1-Tetrahydrocortisol&action=edit&redlink=1" class="new" title="3α,5α-Tetrahydrocortisol (page does not exist)">3α,5α-Tetrahydrocortisol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Mineralocorticoid" title="Mineralocorticoid">Mineralocorticoids</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/5%CE%B1-Dihydroaldosterone" title="5α-Dihydroaldosterone">5α-Dihydroaldosterone</a></li> <li><a href="/wiki/11-Dehydrocorticosterone" title="11-Dehydrocorticosterone">11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone)</a></li> <li><a href="/wiki/11-Deoxycortisol" title="11-Deoxycortisol">11-Deoxycortisol</a></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone</a></li> <li><a href="/wiki/11%CE%B2-Hydroxyprogesterone" title="11β-Hydroxyprogesterone">11β-Hydroxyprogesterone (21-deoxycorticosterone)</a></li> <li><a href="/wiki/18-Hydroxy-11-deoxycorticosterone" title="18-Hydroxy-11-deoxycorticosterone">18-Hydroxy-11-deoxycorticosterone</a></li> <li><a href="/wiki/18-Hydroxycorticosterone" title="18-Hydroxycorticosterone">18-Hydroxycorticosterone</a></li> <li><a href="/w/index.php?title=18-Hydroxyprogesterone&action=edit&redlink=1" class="new" title="18-Hydroxyprogesterone (page does not exist)">18-Hydroxyprogesterone</a></li> <li><a href="/wiki/Aldosterone" title="Aldosterone">Aldosterone</a></li> <li><a href="/wiki/Corticosterone" title="Corticosterone">Corticosterone</a></li> <li><a href="/wiki/Cortisol" title="Cortisol">Cortisol</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sex_steroid" class="mw-redirect" title="Sex steroid">Sex steroids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Androgen" title="Androgen">Androgens</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/11-Ketodihydrotestosterone" title="11-Ketodihydrotestosterone">11-Ketodihydrotestosterone</a></li> <li><a href="/wiki/11-Ketotestosterone" title="11-Ketotestosterone">11-Ketotestosterone</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/11%CE%B2-Hydroxyandrostenedione" title="11β-Hydroxyandrostenedione">11β-Hydroxyandrostenedione</a></li> <li><a href="/wiki/Adrenosterone" title="Adrenosterone">Adrenosterone (11-ketoandrostenedione)</a></li> <li><a href="/wiki/Androstenediol" title="Androstenediol">Androstenediol</a></li> <li><a href="/wiki/Androstenedione" title="Androstenedione">Androstenedione</a></li> <li><a href="/wiki/Androsterone" title="Androsterone">Androsterone</a></li> <li><a href="/wiki/Dehydroandrosterone" title="Dehydroandrosterone">Dehydroandrosterone</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA sulfate</a></li> <li><a href="/wiki/Dihydrotestosterone" title="Dihydrotestosterone">Dihydrotestosterone</a></li> <li><a href="/wiki/Epiandrosterone" title="Epiandrosterone">Epiandrosterone</a></li> <li><a href="/wiki/Epitestosterone" title="Epitestosterone">Epitestosterone</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyandrostenedione" title="16α-Hydroxyandrostenedione">16α-Hydroxyandrostenedione</a></li> <li><a href="/wiki/16-Hydroxydehydroepiandrosterone" class="mw-redirect" title="16-Hydroxydehydroepiandrosterone">16α-Hydroxy-DHEA</a></li> <li><a href="/wiki/16-Hydroxydehydroepiandrosterone_sulfate" class="mw-redirect" title="16-Hydroxydehydroepiandrosterone sulfate">16α-Hydroxy-DHEA sulfate</a></li> <li><a href="/wiki/Testosterone" title="Testosterone">Testosterone</a></li></ul> <ul><li><i>Metabolites:</i> <a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/wiki/3%CE%B1-Androstanediol_glucuronide" class="mw-redirect" title="3α-Androstanediol glucuronide">3α-Androstanediol glucuronide</a></li> <li><a href="/wiki/3%CE%B2-Androstanediol" title="3β-Androstanediol">3β-Androstanediol</a></li> <li><a href="/wiki/5%CE%B2-Dihydrotestosterone" title="5β-Dihydrotestosterone">5β-Dihydrotestosterone</a></li> <li><a href="/wiki/3%CE%B1-Etiocholanediol" title="3α-Etiocholanediol">3α-Etiocholanediol</a></li> <li><a href="/wiki/3%CE%B2-Etiocholanediol" title="3β-Etiocholanediol">3β-Etiocholanediol</a></li> <li><a href="/w/index.php?title=Androstanetriol&action=edit&redlink=1" class="new" title="Androstanetriol (page does not exist)">Androstanetriols</a></li> <li><a href="/wiki/Androstenediol_sulfate" title="Androstenediol sulfate">Androstenediol sulfate</a></li> <li><a href="/wiki/Androstenetriol" title="Androstenetriol">Androstenetriol</a></li> <li><a href="/wiki/Androsterone_glucuronide" title="Androsterone glucuronide">Androsterone glucuronide</a></li> <li><a href="/wiki/Androsterone_sulfate" title="Androsterone sulfate">Androsterone sulfate</a></li> <li><a href="/w/index.php?title=Dihydrotestosterone_glucuronide&action=edit&redlink=1" class="new" title="Dihydrotestosterone glucuronide (page does not exist)">Dihydrotestosterone glucuronide</a></li> <li><a href="/w/index.php?title=Dihydrotestosterone_sulfate&action=edit&redlink=1" class="new" title="Dihydrotestosterone sulfate (page does not exist)">Dihydrotestosterone sulfate</a></li> <li><a href="/wiki/Etiocholanedione" title="Etiocholanedione">Etiocholanedione</a></li> <li><a href="/wiki/Etiocholanolone" title="Etiocholanolone">Etiocholanolone</a></li> <li><a href="/wiki/Etiocholanolone_glucuronide" title="Etiocholanolone glucuronide">Etiocholanolone glucuronide</a></li> <li><a href="/wiki/Epietiocholanolone" title="Epietiocholanolone">Epietiocholanolone</a></li> <li><a href="/wiki/Testosterone_glucuronide" title="Testosterone glucuronide">Testosterone glucuronide</a></li> <li><a href="/wiki/Testosterone_sulfate" title="Testosterone sulfate">Testosterone sulfate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a class="mw-selflink selflink">Estrogens</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Estranes:</i> <a href="/wiki/Estetrol" title="Estetrol">Estetrol</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/wiki/Estrone" title="Estrone">Estrone</a></li> <li><a href="/wiki/Estriol" title="Estriol">Estriol</a></li> <li><a href="/wiki/17%CE%B1-Estradiol" title="17α-Estradiol">17α-Estradiol</a></li> <li><a href="/wiki/Epiestriol" title="Epiestriol">16β-Epiestriol (16β-hydroxyestradiol)</a></li> <li><a href="/wiki/17%CE%B1-Epiestriol" title="17α-Epiestriol">17α-Epiestriol (16α-hydroxy-17α-estradiol)</a></li> <li><a href="/wiki/16%CE%B2,17%CE%B1-Epiestriol" title="16β,17α-Epiestriol">16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)</a></li> <li><a href="/wiki/2-Hydroxyestradiol" title="2-Hydroxyestradiol">2-Hydroxyestradiol</a></li> <li><a href="/wiki/2-Hydroxyestriol" title="2-Hydroxyestriol">2-Hydroxyestriol</a></li> <li><a href="/wiki/2-Hydroxyestrone" title="2-Hydroxyestrone">2-Hydroxyestrone</a></li> <li><a href="/wiki/4-Hydroxyestradiol" title="4-Hydroxyestradiol">4-Hydroxyestradiol</a></li> <li><a href="/wiki/4-Hydroxyestriol" title="4-Hydroxyestriol">4-Hydroxyestriol</a></li> <li><a href="/wiki/4-Hydroxyestrone" title="4-Hydroxyestrone">4-Hydroxyestrone</a></li> <li><a href="/wiki/4-Methoxyestradiol" title="4-Methoxyestradiol">4-Methoxyestradiol</a></li> <li><a href="/wiki/4-Methoxyestrone" title="4-Methoxyestrone">4-Methoxyestrone</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyestrone" title="16α-Hydroxyestrone">16α-Hydroxyestrone</a></li> <li><a href="/wiki/16%CE%B2-Hydroxyestrone" title="16β-Hydroxyestrone">16β-Hydroxyestrone</a></li> <li><a href="/wiki/16-Ketoestradiol" title="16-Ketoestradiol">16-Ketoestradiol</a></li> <li><a href="/wiki/16-Ketoestrone" title="16-Ketoestrone">16-Ketoestrone</a></li></ul> <ul><li><i>Others:</i> <a href="/wiki/27-Hydroxycholesterol" title="27-Hydroxycholesterol">27-Hydroxycholesterol</a></li> <li><a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/wiki/3%CE%B2-Androstanediol" title="3β-Androstanediol">3β-Androstanediol</a></li> <li><a href="/wiki/4-Androstenedione" class="mw-redirect" title="4-Androstenedione">4-Androstenedione</a></li> <li><a href="/wiki/5-Androstenediol" class="mw-redirect" title="5-Androstenediol">5-Androstenediol</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA sulfate</a></li> <li><a href="/wiki/7-Keto-DHEA" title="7-Keto-DHEA">7-Keto-DHEA</a></li> <li><a href="/wiki/7%CE%B1-Hydroxy-DHEA" title="7α-Hydroxy-DHEA">7α-Hydroxy-DHEA</a></li> <li><a href="/wiki/16-Hydroxydehydroepiandrosterone" class="mw-redirect" title="16-Hydroxydehydroepiandrosterone">16α-Hydroxy-DHEA</a></li></ul> <ul><li><i>Metabolites:</i> <a href="/wiki/2-Methoxyestradiol" title="2-Methoxyestradiol">2-Methoxyestradiol</a></li> <li><a href="/wiki/2-Methoxyestrone" title="2-Methoxyestrone">2-Methoxyestrone</a></li> <li><a href="/wiki/2-Methoxyestriol" title="2-Methoxyestriol">2-Methoxyestriol</a></li> <li><a href="/wiki/4-Methoxyestriol" title="4-Methoxyestriol">4-Methoxyestriol</a></li> <li><a href="/wiki/Estradiol_disulfate" title="Estradiol disulfate">Estradiol disulfate</a></li> <li><a href="/wiki/Estradiol_glucuronide" title="Estradiol glucuronide">Estradiol glucuronide</a></li> <li><a href="/wiki/Estradiol_3-glucuronide" title="Estradiol 3-glucuronide">Estradiol 3-glucuronide</a></li> <li><a href="/wiki/Estradiol_3-glucuronide_17%CE%B2-sulfate" title="Estradiol 3-glucuronide 17β-sulfate">Estradiol 3-glucuronide 17β-sulfate</a></li> <li><a href="/wiki/Estradiol_sulfate" title="Estradiol sulfate">Estradiol sulfate</a></li> <li><a href="/wiki/Estradiol_17%CE%B2-sulfate" title="Estradiol 17β-sulfate">Estradiol 17β-sulfate</a></li> <li><a href="/wiki/Estrone_glucuronide" title="Estrone glucuronide">Estrone glucuronide</a></li> <li><a href="/wiki/Estrone_sulfate" title="Estrone sulfate">Estrone sulfate</a></li> <li><a href="/wiki/Estriol_glucuronide" title="Estriol glucuronide">Estriol glucuronide</a></li> <li><a href="/wiki/Estriol_sulfate" title="Estriol sulfate">Estriol sulfate</a></li> <li><a href="/wiki/Lipoidal_estradiol" title="Lipoidal estradiol">Lipoidal estradiol</a> (e.g., <a href="/wiki/Estradiol_stearate" title="Estradiol stearate">estradiol stearate</a>, <a href="/wiki/Estradiol_palmitate" title="Estradiol palmitate">estradiol palmitate</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Progestogen" title="Progestogen">Progestogens</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyprogesterone" title="16α-Hydroxyprogesterone">16α-Hydroxyprogesterone</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone</a></li> <li><a href="/wiki/20%CE%B1-Dihydroprogesterone" title="20α-Dihydroprogesterone">20α-Dihydroprogesterone</a></li> <li><a href="/wiki/20%CE%B2-Dihydroprogesterone" title="20β-Dihydroprogesterone">20β-Dihydroprogesterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">5α-Dihydroprogesterone</a></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone</a></li> <li><a href="/wiki/Dihydrodeoxycorticosterone" title="Dihydrodeoxycorticosterone">5α-DHDOC</a></li></ul> <ul><li><i>Metabolites:</i> <a href="/wiki/Allopregnanediol" title="Allopregnanediol">Allopregnanediol</a></li> <li><a href="/wiki/Pregnanediol" title="Pregnanediol">Pregnanediol</a></li> <li><a href="/wiki/Pregnanediol_glucuronide" title="Pregnanediol glucuronide">Pregnanediol glucuronide</a></li> <li><a href="/wiki/Pregnanetriol" title="Pregnanetriol">Pregnanetriol</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Neuroactive_steroid" class="mw-redirect" title="Neuroactive steroid">Neurosteroids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Cholestanes:</i> <a href="/wiki/24S-hydroxycholesterol" class="mw-redirect" title="24S-hydroxycholesterol">24<i>S</i>-Hydroxycholesterol</a></li> <li><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></li></ul> <ul><li><i>Pregnanes:</i> <a href="/wiki/3%CE%B1-Dihydroprogesterone" title="3α-Dihydroprogesterone">3α-Dihydroprogesterone</a></li> <li><a href="/wiki/3%CE%B2-Dihydroprogesterone" title="3β-Dihydroprogesterone">3β-Dihydroprogesterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydrocorticosterone" title="5α-Dihydrocorticosterone">5α-Dihydrocorticosterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">5α-Dihydroprogesterone</a></li> <li><a href="/wiki/5%CE%B2-Dihydroprogesterone" title="5β-Dihydroprogesterone">5β-Dihydroprogesterone</a></li> <li><a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone</a></li> <li><a href="/wiki/Corticosterone" title="Corticosterone">Corticosterone</a></li> <li><a href="/wiki/Dihydrocorticosterone" class="mw-redirect" title="Dihydrocorticosterone">DHC</a></li> <li><a href="/wiki/Dihydrodeoxycorticosterone" title="Dihydrodeoxycorticosterone">DHDOC</a></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone</a></li> <li><a href="/wiki/Epipregnanolone" title="Epipregnanolone">Epipregnanolone</a></li> <li><a href="/wiki/Isopregnanolone" title="Isopregnanolone">Isopregnanolone</a></li> <li><a href="/wiki/Pregnanolone" title="Pregnanolone">Pregnanolone</a></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a></li> <li><a href="/wiki/Pregnenolone_sulfate" title="Pregnenolone sulfate">Pregnenolone sulfate</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Tetrahydrocorticosterone" title="Tetrahydrocorticosterone">THB</a></li> <li><a href="/wiki/Tetrahydrodeoxycorticosterone" title="Tetrahydrodeoxycorticosterone">THDOC</a></li></ul> <ul><li><i>Androstanes:</i> <a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/wiki/3%CE%B1-Androstenol" class="mw-redirect" title="3α-Androstenol">3α-Androstenol</a></li> <li><a href="/wiki/7-Keto-DHEA" title="7-Keto-DHEA">7-Keto-DHEA</a></li> <li><a href="/wiki/7%CE%B1-Hydroxy-DHEA" title="7α-Hydroxy-DHEA">7α-Hydroxy-DHEA</a></li> <li><a href="/wiki/7%CE%B2-Hydroxy-DHEA" title="7β-Hydroxy-DHEA">7β-Hydroxy-DHEA</a></li> <li><a href="/wiki/7%CE%B1-Hydroxyepiandrosterone" title="7α-Hydroxyepiandrosterone">7α-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/Androsterone" title="Androsterone">Androsterone</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA sulfate</a></li> <li><a href="/wiki/Etiocholanolone" title="Etiocholanolone">Etiocholanolone</a></li></ul> <ul><li><b><a href="/wiki/Pheromone" title="Pheromone">Pheromones</a>:</b> <a href="/wiki/3%CE%B1-Androstenol" class="mw-redirect" title="3α-Androstenol">3α-Androstenol</a></li> <li><a href="/wiki/3%CE%B2-Androstenol" title="3β-Androstenol">3β-Androstenol</a></li> <li><a href="/wiki/Androstadienol" title="Androstadienol">Androstadienol</a></li> <li><a href="/wiki/Androstadienone" title="Androstadienone">Androstadienone</a></li> <li><a href="/wiki/Androstenone" title="Androstenone">Androstenone</a></li> <li><a href="/wiki/Androsterone" title="Androsterone">Androsterone</a></li> <li><a href="/wiki/Estratetraenol" title="Estratetraenol">Estratetraenol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b><a href="/wiki/Vitamin_D" title="Vitamin D">Vitamin D</a>:</b> <a href="/wiki/7-Dehydrocholesterol" title="7-Dehydrocholesterol">7-Dehydrocholesterol</a></li> <li><a href="/wiki/Calcifediol" title="Calcifediol">Calcidiol/Calcifediol</a></li> <li><a href="/wiki/Calcitriol" title="Calcitriol">Calcitriol</a></li> <li><a href="/wiki/Cholecalciferol" title="Cholecalciferol">Cholecalciferol</a></li></ul> <ul><li><b>Others:</b> <a href="/wiki/7%CE%B1-Hydroxycholesterol" title="7α-Hydroxycholesterol">7α-Hydroxycholesterol</a></li> <li><a href="/wiki/11%CE%B1-Hydroxyprogesterone" title="11α-Hydroxyprogesterone">11α-Hydroxyprogesterone</a></li> <li><a href="/wiki/11%CE%B2-Hydroxyprogesterone" title="11β-Hydroxyprogesterone">11β-Hydroxyprogesterone</a></li> <li><a href="/wiki/Cholesterol_sulfate" title="Cholesterol sulfate">Cholesterol sulfate</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Estrogens_and_antiestrogens109" 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_antiestrogens109" 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"><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"><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 href="/wiki/Clomifene" title="Clomifene">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"><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="Estrogen_receptor_modulators1222" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Estrogen_receptor_modulators" title="Template talk:Estrogen receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Estrogen_receptor_modulators" title="Special:EditPage/Template:Estrogen receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Estrogen_receptor_modulators1222" style="font-size:114%;margin:0 4em"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor">Estrogen receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Steroidal:</i> <a href="/wiki/2-Hydroxyestradiol" title="2-Hydroxyestradiol">2-Hydroxyestradiol</a></li> <li><a href="/wiki/2-Hydroxyestrone" title="2-Hydroxyestrone">2-Hydroxyestrone</a></li> <li><a href="/wiki/3-Methyl-19-methyleneandrosta-3,5-dien-17%CE%B2-ol" title="3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol">3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol</a></li> <li><a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/w/index.php?title=3%CE%B1,5%CE%B1-Dihydrolevonorgestrel&action=edit&redlink=1" class="new" title="3α,5α-Dihydrolevonorgestrel (page does not exist)">3α,5α-Dihydrolevonorgestrel</a></li> <li><a href="/w/index.php?title=3%CE%B2,5%CE%B1-Dihydrolevonorgestrel&action=edit&redlink=1" class="new" title="3β,5α-Dihydrolevonorgestrel (page does not exist)">3β,5α-Dihydrolevonorgestrel</a></li> <li><a href="/wiki/3%CE%B1-Hydroxytibolone" title="3α-Hydroxytibolone">3α-Hydroxytibolone</a></li> <li><a href="/wiki/3%CE%B2-Hydroxytibolone" title="3β-Hydroxytibolone">3β-Hydroxytibolone</a></li> <li><a href="/wiki/3%CE%B2-Androstanediol" title="3β-Androstanediol">3β-Androstanediol</a></li> <li><a href="/wiki/4-Androstenediol" title="4-Androstenediol">4-Androstenediol</a></li> <li><a href="/wiki/4-Androstenedione" class="mw-redirect" title="4-Androstenedione">4-Androstenedione</a></li> <li><a href="/wiki/4-Fluoroestradiol" title="4-Fluoroestradiol">4-Fluoroestradiol</a></li> <li><a href="/wiki/4-Hydroxyestradiol" title="4-Hydroxyestradiol">4-Hydroxyestradiol</a></li> <li><a href="/wiki/4-Hydroxyestrone" title="4-Hydroxyestrone">4-Hydroxyestrone</a></li> <li><a href="/wiki/4-Methoxyestradiol" title="4-Methoxyestradiol">4-Methoxyestradiol</a></li> <li><a href="/wiki/4-Methoxyestrone" title="4-Methoxyestrone">4-Methoxyestrone</a></li> <li><a href="/wiki/5-Androstenediol" class="mw-redirect" title="5-Androstenediol">5-Androstenediol</a></li> <li><a href="/wiki/7-Keto-DHEA" title="7-Keto-DHEA">7-Oxo-DHEA</a></li> <li><a href="/wiki/7%CE%B1-Hydroxy-DHEA" title="7α-Hydroxy-DHEA">7α-Hydroxy-DHEA</a></li> <li><a href="/wiki/7%CE%B1-Methylestradiol" title="7α-Methylestradiol">7α-Methylestradiol</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/8,9-Dehydroestradiol" title="8,9-Dehydroestradiol">8,9-Dehydroestradiol</a></li> <li><a href="/wiki/8,9-Dehydroestrone" title="8,9-Dehydroestrone">8,9-Dehydroestrone</a></li> <li><a href="/wiki/8%CE%B2-VE2" title="8β-VE2">8β-VE2</a></li> <li><a href="/wiki/10%CE%B2,17%CE%B2-Dihydroxyestra-1,4-dien-3-one" title="10β,17β-Dihydroxyestra-1,4-dien-3-one">10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)</a></li> <li><a href="/wiki/11%CE%B2-Chloromethylestradiol" title="11β-Chloromethylestradiol">11β-Chloromethylestradiol</a></li> <li><a href="/wiki/11%CE%B2-Methoxyestradiol" title="11β-Methoxyestradiol">11β-Methoxyestradiol</a></li> <li><a href="/wiki/15%CE%B1-Hydroxyestradiol" title="15α-Hydroxyestradiol">15α-Hydroxyestradiol</a></li> <li><a href="/wiki/16-Ketoestradiol" title="16-Ketoestradiol">16-Ketoestradiol</a></li> <li><a href="/wiki/16-Ketoestrone" title="16-Ketoestrone">16-Ketoestrone</a></li> <li><a href="/wiki/16%CE%B1-Fluoroestradiol" class="mw-redirect" title="16α-Fluoroestradiol">16α-Fluoroestradiol</a></li> <li><a href="/wiki/16%CE%B1-Hydroxy-DHEA" title="16α-Hydroxy-DHEA">16α-Hydroxy-DHEA</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyestrone" title="16α-Hydroxyestrone">16α-Hydroxyestrone</a></li> <li><a href="/wiki/16%CE%B1-Iodoestradiol" class="mw-redirect" title="16α-Iodoestradiol">16α-Iodoestradiol</a></li> <li><a href="/wiki/16%CE%B1-LE2" title="16α-LE2">16α-LE2</a></li> <li><a href="/wiki/16%CE%B2-Hydroxyestrone" title="16β-Hydroxyestrone">16β-Hydroxyestrone</a></li> <li><a href="/wiki/16%CE%B2,17%CE%B1-Epiestriol" title="16β,17α-Epiestriol">16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)</a></li> <li><a href="/wiki/17%CE%B1-Estradiol" title="17α-Estradiol">17α-Estradiol</a> (<a href="/wiki/Alfatradiol" title="Alfatradiol">alfatradiol</a>)</li> <li><a href="/wiki/17%CE%B1-Dihydroequilenin" title="17α-Dihydroequilenin">17α-Dihydroequilenin</a></li> <li><a href="/wiki/17%CE%B1-Dihydroequilin" title="17α-Dihydroequilin">17α-Dihydroequilin</a></li> <li><a href="/wiki/17%CE%B1-Epiestriol" title="17α-Epiestriol">17α-Epiestriol (16α-hydroxy-17α-estradiol)</a></li> <li><a href="/wiki/17%CE%B1-Ethynyl-3%CE%B1-androstanediol" title="17α-Ethynyl-3α-androstanediol">17α-Ethynyl-3α-androstanediol</a></li> <li><a href="/wiki/17%CE%B1-Ethynyl-3%CE%B2-androstanediol" title="17α-Ethynyl-3β-androstanediol">17α-Ethynyl-3β-androstanediol</a></li> <li><a href="/wiki/17%CE%B2-Dihydroequilenin" title="17β-Dihydroequilenin">17β-Dihydroequilenin</a></li> <li><a href="/wiki/17%CE%B2-Dihydroequilin" title="17β-Dihydroequilin">17β-Dihydroequilin</a></li> <li><a href="/wiki/17%CE%B2-Methyl-17%CE%B1-dihydroequilenin" title="17β-Methyl-17α-dihydroequilenin">17β-Methyl-17α-dihydroequilenin</a></li> <li><a href="/wiki/Abiraterone" class="mw-redirect" title="Abiraterone">Abiraterone</a></li> <li><a href="/wiki/Abiraterone_acetate" title="Abiraterone acetate">Abiraterone acetate</a></li> <li><a href="/wiki/Alestramustine" title="Alestramustine">Alestramustine</a></li> <li><a href="/wiki/Almestrone" title="Almestrone">Almestrone</a></li> <li><a href="/wiki/Anabolic_steroid" title="Anabolic steroid">Anabolic steroids</a> (e.g., <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> and <a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">esters</a>, <a href="/wiki/Methyltestosterone" title="Methyltestosterone">methyltestosterone</a>, <a href="/wiki/Metandienone" title="Metandienone">metandienone (methandrostenolone)</a>, <a href="/wiki/Nandrolone" title="Nandrolone">nandrolone</a> and <a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">esters</a>, many others; via estrogenic metabolites)</li> <li><a href="/wiki/Atrimustine" title="Atrimustine">Atrimustine</a></li> <li><a href="/wiki/Bolandiol" title="Bolandiol">Bolandiol</a></li> <li><a href="/wiki/Bolandiol_dipropionate" title="Bolandiol dipropionate">Bolandiol dipropionate</a></li> <li><a href="/wiki/Butolame" title="Butolame">Butolame</a></li> <li><a href="/wiki/Clomestrone" title="Clomestrone">Clomestrone</a></li> <li><a href="/wiki/Cloxestradiol" title="Cloxestradiol">Cloxestradiol</a> <ul><li><a href="/wiki/Cloxestradiol_acetate" title="Cloxestradiol acetate">Cloxestradiol acetate</a></li></ul></li> <li><a href="/wiki/Conjugated_estriol" title="Conjugated estriol">Conjugated estriol</a></li> <li><a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a></li> <li><a href="/wiki/Cyclodiol" title="Cyclodiol">Cyclodiol</a></li> <li><a href="/wiki/Cyclotriol" title="Cyclotriol">Cyclotriol</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA-S</a></li> <li><a href="/wiki/Ent-Estradiol" title="Ent-Estradiol"><i>ent</i>-Estradiol</a></li> <li><a href="/wiki/Epiestriol" title="Epiestriol">Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)</a></li> <li><a href="/wiki/Epimestrol" title="Epimestrol">Epimestrol</a></li> <li><a href="/wiki/Equilenin" title="Equilenin">Equilenin</a></li> <li><a href="/wiki/Equilin" title="Equilin">Equilin</a></li> <li><a href="/wiki/ERA-63" title="ERA-63">ERA-63 (ORG-37663)</a></li> <li><a href="/wiki/Esterified_estrogens" title="Esterified estrogens">Esterified estrogens</a></li> <li><a href="/wiki/Estetrol" title="Estetrol">Estetrol</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estradiol_esters" title="List of estrogen esters">Estradiol esters</a></li> <li><a href="/wiki/Lipoidal_estradiol" title="Lipoidal estradiol">Lipoidal estradiol</a></li> <li><a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">Polyestradiol phosphate</a></li></ul></li> <li><a href="/wiki/Estramustine" title="Estramustine">Estramustine</a></li> <li><a href="/wiki/Estramustine_phosphate" title="Estramustine phosphate">Estramustine phosphate</a></li> <li><a href="/wiki/Estrapronicate" title="Estrapronicate">Estrapronicate</a></li> <li><a href="/wiki/Estrazinol" title="Estrazinol">Estrazinol</a></li> <li><a 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 href="/wiki/Clomifene" title="Clomifene">Clomifene</a></li> <li><a href="/wiki/Clomifenoxide" title="Clomifenoxide">Clomifenoxide</a></li> <li><a href="/w/index.php?title=CN-55945-27&action=edit&redlink=1" class="new" title="CN-55945-27 (page does not exist)">CN-55945-27</a></li> <li><a href="/wiki/Cyclofenil" title="Cyclofenil">Cyclofenil</a></li> <li><a href="/w/index.php?title=D-15413&action=edit&redlink=1" class="new" title="D-15413 (page does not exist)">D-15413</a></li> <li><a href="/wiki/Desmethylchlorotrianisene" title="Desmethylchlorotrianisene">Desmethylchlorotrianisene</a></li> <li><a href="/wiki/Droloxifene" title="Droloxifene">Droloxifene</a></li> <li><a href="/wiki/Enclomifene" title="Enclomifene">Enclomifene</a></li> <li><a href="/wiki/Endoxifen" title="Endoxifen">Endoxifen</a></li> <li><a href="/wiki/Etacstil" title="Etacstil">Etacstil (GW-5638, DPC-974)</a></li> <li><a href="/wiki/Ethamoxytriphetol" title="Ethamoxytriphetol">Ethamoxytriphetol (MER-25)</a></li> <li><a href="/wiki/Femarelle" title="Femarelle">Femarelle</a></li> <li><a href="/wiki/Fispemifene" title="Fispemifene">Fispemifene</a></li> <li><a href="/w/index.php?title=GW-7604&action=edit&redlink=1" class="new" title="GW-7604 (page does not exist)">GW-7604</a></li> <li><a href="/wiki/ICI-55548" class="mw-redirect" title="ICI-55548">ICI-55548</a></li> <li><a href="/wiki/Idoxifene" title="Idoxifene">Idoxifene</a></li> <li><a href="/wiki/Lasofoxifene" title="Lasofoxifene">Lasofoxifene</a></li> <li><a href="/wiki/Levormeloxifene" title="Levormeloxifene">Levormeloxifene</a></li> <li><a href="/wiki/LN-1643" class="mw-redirect" title="LN-1643">LN-1643</a></li> <li><a href="/wiki/LN-2299" class="mw-redirect" title="LN-2299">LN-2299</a></li> <li><a href="/w/index.php?title=LY-117018&action=edit&redlink=1" class="new" title="LY-117018 (page does not exist)">LY-117018</a></li> <li><a href="/wiki/Menerba" title="Menerba">Menerba</a></li> <li><a href="/wiki/Miproxifene" title="Miproxifene">Miproxifene</a></li> <li><a href="/wiki/Miproxifene_phosphate" title="Miproxifene phosphate">Miproxifene phosphate</a></li> <li><a href="/w/index.php?title=MRL-37&action=edit&redlink=1" class="new" title="MRL-37 (page does not exist)">MRL-37</a></li> <li><a href="/wiki/Nafoxidine" title="Nafoxidine">Nafoxidine</a></li> <li><a href="/wiki/Nitromifene" title="Nitromifene">Nitromifene</a></li> <li><a href="/wiki/NNC_45-0095" title="NNC 45-0095">NNC 45-0095</a></li> <li><a href="/w/index.php?title=NNC_45-0320&action=edit&redlink=1" class="new" title="NNC 45-0320 (page does not exist)">NNC 45-0320</a></li> <li><a href="/w/index.php?title=NNC_45-0781&action=edit&redlink=1" class="new" title="NNC 45-0781 (page does not exist)">NNC 45-0781</a></li> <li><a href="/w/index.php?title=NNC_45-1506&action=edit&redlink=1" class="new" title="NNC 45-1506 (page does not exist)">NNC 45-1506</a></li> <li><a href="/wiki/Ormeloxifene" title="Ormeloxifene">Ormeloxifene</a></li> <li><a href="/wiki/Ospemifene" title="Ospemifene">Ospemifene</a></li> <li><a href="/wiki/Panomifene" title="Panomifene">Panomifene</a></li> <li><a href="/wiki/Pipendoxifene" title="Pipendoxifene">Pipendoxifene</a></li> <li><a href="/w/index.php?title=Promensil&action=edit&redlink=1" class="new" title="Promensil (page does not exist)">Promensil</a></li> <li><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></li> <li><a href="/wiki/Rimostil" title="Rimostil">Rimostil (P-081)</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/w/index.php?title=SS1010&action=edit&redlink=1" class="new" title="SS1010 (page does not exist)">SS1010</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a></li> <li><a href="/wiki/TAS-108" title="TAS-108">TAS-108 (SR-16234)</a></li> <li><a href="/wiki/Toremifene" title="Toremifene">Toremifene</a></li> <li><a href="/wiki/Trioxifene" title="Trioxifene">Trioxifene</a></li> <li><a href="/w/index.php?title=TZE-5323&action=edit&redlink=1" class="new" title="TZE-5323 (page does not exist)">TZE-5323</a></li> <li><a href="/w/index.php?title=U-11555A&action=edit&redlink=1" class="new" title="U-11555A (page does not exist)">U-11555A</a></li> <li><a href="/w/index.php?title=U-11634&action=edit&redlink=1" class="new" title="U-11634 (page does not exist)">U-11634</a></li> <li><a href="/w/index.php?title=Y-134&action=edit&redlink=1" class="new" title="Y-134 (page does not exist)">Y-134</a></li> <li><a href="/wiki/Zindoxifene" title="Zindoxifene">Zindoxifene</a></li> <li><a href="/wiki/Zuclomifene" title="Zuclomifene">Zuclomifene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/(R,R)-Tetrahydrochrysene" title="(R,R)-Tetrahydrochrysene">(R,R)-THC</a></li> <li><a href="/wiki/7%CE%B2-Hydroxy-DHEA" title="7β-Hydroxy-DHEA">7β-Hydroxy-DHEA</a></li> <li><a href="/w/index.php?title=Chloroindazole&action=edit&redlink=1" class="new" title="Chloroindazole (page does not exist)">Chloroindazole</a></li> <li><a href="/wiki/Cytestrol_acetate" title="Cytestrol acetate">Cytestrol acetate</a></li> <li><a href="/w/index.php?title=EM-800&action=edit&redlink=1" class="new" title="EM-800 (page does not exist)">EM-800 (SCH-57050)</a></li> <li><a href="/wiki/Epitiostanol" title="Epitiostanol">Epitiostanol</a></li> <li><a href="/w/index.php?title=ERA-90&action=edit&redlink=1" class="new" title="ERA-90 (page does not exist)">ERA-90</a></li> <li><a href="/w/index.php?title=ERB-88&action=edit&redlink=1" class="new" title="ERB-88 (page does not exist)">ERB-88</a></li> <li><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant (ICI-182780)</a></li> <li><a href="/wiki/Glyceollin" title="Glyceollin">Glyceollins</a> (<a href="/wiki/Glyceollin_I" title="Glyceollin I">I</a>, <a href="/w/index.php?title=Glyceollin_II&action=edit&redlink=1" class="new" title="Glyceollin II (page does not exist)">II</a>, <a href="/wiki/Glyceollin_III" title="Glyceollin III">III</a>, <a href="/w/index.php?title=Glyceollin_IV&action=edit&redlink=1" class="new" title="Glyceollin IV (page does not exist)">IV</a>)</li> <li><a href="/wiki/ICI-164384" title="ICI-164384">ICI-164384</a></li> <li><a href="/w/index.php?title=MDL-101906&action=edit&redlink=1" class="new" title="MDL-101906 (page does not exist)">MDL-101906</a></li> <li><a href="/wiki/Mepitiostane" title="Mepitiostane">Mepitiostane</a></li> <li><a href="/wiki/Methylepitiostanol" title="Methylepitiostanol">Methylepitiostanol</a></li> <li><a href="/wiki/Methylpiperidinopyrazole" title="Methylpiperidinopyrazole">Methylpiperidinopyrazole</a></li> <li><a href="/wiki/MIBE" title="MIBE">MIBE</a></li> <li><a href="/w/index.php?title=Oxabicycloheptene_sulfonate&action=edit&redlink=1" class="new" title="Oxabicycloheptene sulfonate (page does not exist)">Oxabicycloheptene sulfonate</a></li> <li><a href="/wiki/Phenytoin" title="Phenytoin">Phenytoin</a></li> <li><a href="/wiki/PHTPP" title="PHTPP">PHTPP</a></li> <li><a href="/wiki/Prochloraz" title="Prochloraz">Prochloraz</a></li> <li><a href="/w/index.php?title=RU-39411&action=edit&redlink=1" class="new" title="RU-39411 (page does not exist)">RU-39411</a></li> <li><a href="/w/index.php?title=RU-58668&action=edit&redlink=1" class="new" title="RU-58668 (page does not exist)">RU-58668</a></li> <li><a href="/w/index.php?title=SS1020&action=edit&redlink=1" class="new" title="SS1020 (page does not exist)">SS1020</a></li> <li><a href="/wiki/TAS-108" title="TAS-108">TAS-108 (SR-16234)</a></li> <li><a href="/wiki/ZB716" title="ZB716">ZB716</a></li> <li><a href="/w/index.php?title=ZK-164015&action=edit&redlink=1" class="new" title="ZK-164015 (page does not exist)">ZK-164015</a></li> <li><a href="/w/index.php?title=ZK-191703&action=edit&redlink=1" class="new" title="ZK-191703 (page does not exist)">ZK-191703</a></li></ul> <ul><li><i>Coregulator-binding modulators:</i> <a href="/wiki/ERX-11" title="ERX-11">ERX-11</a></li></ul> <ul><li><i>Noncompetitive inhibitors:</i> <a href="/wiki/Trilostane" title="Trilostane">Trilostane</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/G_protein-coupled_estrogen_receptor" class="mw-redirect" title="G protein-coupled estrogen receptor"><abbr title="G protein-coupled estrogen receptor">GPER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip G protein-coupled estrogen receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Methoxyestradiol" title="2-Methoxyestradiol">2-Methoxyestradiol</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/Afimoxifene" title="Afimoxifene">Afimoxifene (4-hydroxytamoxifen)</a></li> <li><a href="/wiki/Aldosterone" title="Aldosterone">Aldosterone</a></li> <li><a href="/wiki/Atrazine" title="Atrazine">Atrazine</a></li> <li><a href="/wiki/Bisphenol_A" title="Bisphenol A">Bisphenol A</a></li> <li><a href="/wiki/Daidzein" title="Daidzein">Daidzein</a></li> <li><a href="/wiki/DDT" title="DDT">DDT</a> (<a href="/wiki/P,p%27-DDT" class="mw-redirect" title="P,p'-DDT">p,p'-DDT</a>, <a href="/w/index.php?title=O%27,p%27-DDE&action=edit&redlink=1" class="new" title="O',p'-DDE (page does not exist)">o',p'-DDE</a>)</li> <li><a href="/wiki/Diarylpropionitrile" title="Diarylpropionitrile">Diarylpropionitrile</a></li> <li><a href="/wiki/Equol" title="Equol">Equol</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a></li> <li><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant (ICI-182780)</a></li> <li><a href="/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/Nicotinic_acid" title="Nicotinic acid">Nicotinic acid</a></li> <li><a href="/wiki/Nicotinamide" title="Nicotinamide">Nicotinamide</a></li> <li><a href="/wiki/Nonylphenol" title="Nonylphenol">Nonylphenol</a></li> <li><a href="/wiki/Oleuropein" title="Oleuropein">Oleuropein</a></li> <li><a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">PCBs</a> (<a href="/w/index.php?title=2,2%27,5%27-PCB-4-OH&action=edit&redlink=1" class="new" title="2,2',5'-PCB-4-OH (page does not exist)">2,2',5'-PCB-4-OH</a>)</li> <li><a href="/wiki/Propylpyrazoletriol" title="Propylpyrazoletriol">Propylpyrazoletriol</a></li> <li><a href="/wiki/Quercetin" title="Quercetin">Quercetin</a></li> <li><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></li> <li><a href="/wiki/Resveratrol" title="Resveratrol">Resveratrol</a></li> <li><a href="/w/index.php?title=STX_(drug)&action=edit&redlink=1" class="new" title="STX (drug) (page does not exist)">STX</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a></li> <li><a href="/wiki/Tectoridin" title="Tectoridin">Tectoridin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/CCL18" title="CCL18">CCL18</a></li> <li><a href="/wiki/Estriol" title="Estriol">Estriol</a></li> <li><a href="/w/index.php?title=G-15_(drug)&action=edit&redlink=1" class="new" title="G-15 (drug) (page does not exist)">G-15</a></li> <li><a href="/w/index.php?title=G-36_(drug)&action=edit&redlink=1" class="new" title="G-36 (drug) (page does not exist)">G-36</a></li> <li><a href="/wiki/MIBE" title="MIBE">MIBE</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Unknown</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a></li> <li><a href="/wiki/Zearalenone" title="Zearalenone">Zearalenone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Estrogens_and_antiestrogens" title="Template:Estrogens and antiestrogens">Estrogens and antiestrogens</a></dd> <dd><a href="/wiki/Template:Androgen_receptor_modulators" title="Template:Androgen receptor modulators">Androgen receptor modulators</a></dd> <dd><a href="/wiki/Template:Progesterone_receptor_modulators" title="Template:Progesterone receptor modulators">Progesterone receptor modulators</a></dd> <dd><a href="/wiki/List_of_steroidal_estrogens" class="mw-redirect" title="List of steroidal estrogens">List of estrogens</a></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"><link 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