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class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Breasts"> <div class="vector-toc-text"> 2.4 Breasts </div> </a> <ul id="toc-Breasts-sublist" class="vector-toc-list"> <li id="toc-Lobuloalveolar_development" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Lobuloalveolar_development"> <div class="vector-toc-text"> 2.4.1 Lobuloalveolar development </div> </a> <ul id="toc-Lobuloalveolar_development-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Ductal_development" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Ductal_development"> <div class="vector-toc-text"> 2.4.2 Ductal development </div> </a> <ul id="toc-Ductal_development-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Breast_cancer_risk" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Breast_cancer_risk"> <div class="vector-toc-text"> 2.4.3 Breast cancer risk </div> </a> <ul id="toc-Breast_cancer_risk-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Skin_health" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Skin_health"> <div class="vector-toc-text"> 2.5 Skin health </div> </a> <ul id="toc-Skin_health-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Sexuality" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Sexuality"> <div class="vector-toc-text"> 2.6 Sexuality </div> </a> <ul id="toc-Sexuality-sublist" class="vector-toc-list"> <li id="toc-Libido" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Libido"> <div class="vector-toc-text"> 2.6.1 Libido </div> </a> <ul id="toc-Libido-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Homosexuality" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Homosexuality"> <div class="vector-toc-text"> 2.6.2 Homosexuality </div> </a> <ul id="toc-Homosexuality-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Nervous_system" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Nervous_system"> <div class="vector-toc-text"> 2.7 Nervous system </div> </a> <ul id="toc-Nervous_system-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Brain_damage" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Brain_damage"> <div class="vector-toc-text"> 2.8 Brain damage </div> </a> <ul id="toc-Brain_damage-sublist" class="vector-toc-list"> <li id="toc-Proposed_mechanism" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Proposed_mechanism"> <div class="vector-toc-text"> 2.8.1 Proposed mechanism </div> </a> <ul id="toc-Proposed_mechanism-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Addiction" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Addiction"> <div class="vector-toc-text"> 2.9 Addiction </div> </a> <ul id="toc-Addiction-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Societal" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Societal"> <div class="vector-toc-text"> 2.10 Societal </div> </a> <ul id="toc-Societal-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_effects" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other_effects"> <div class="vector-toc-text"> 2.11 Other effects </div> </a> <ul id="toc-Other_effects-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"> 3 Biochemistry </div> </a> <button aria-controls="toc-Biochemistry-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Biochemistry subsection </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"> 3.1 Biosynthesis </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"> 3.2 Distribution </div> </a> <ul id="toc-Distribution-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metabolism" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Metabolism"> <div class="vector-toc-text"> 3.3 Metabolism </div> </a> <ul id="toc-Metabolism-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Levels" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Levels"> <div class="vector-toc-text"> 3.4 Levels </div> </a> <ul id="toc-Levels-sublist" class="vector-toc-list"> <li id="toc-Ranges" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Ranges"> <div class="vector-toc-text"> 3.4.1 Ranges </div> </a> <ul id="toc-Ranges-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Sources" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Sources"> <div class="vector-toc-text"> 3.5 Sources </div> </a> <ul id="toc-Sources-sublist" class="vector-toc-list"> <li id="toc-Animal" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Animal"> <div class="vector-toc-text"> 3.5.1 Animal </div> </a> <ul id="toc-Animal-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Plants" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Plants"> <div class="vector-toc-text"> 3.5.2 Plants </div> </a> <ul id="toc-Plants-sublist" class="vector-toc-list"> </ul> </li> </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"> 4 Medical use </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"> 5 Chemistry </div> </a> <button aria-controls="toc-Chemistry-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Chemistry subsection </button> <ul id="toc-Chemistry-sublist" class="vector-toc-list"> <li id="toc-Synthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Synthesis"> <div class="vector-toc-text"> 5.1 Synthesis </div> </a> <ul id="toc-Synthesis-sublist" class="vector-toc-list"> <li id="toc-Marker_semisynthesis" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Marker_semisynthesis"> <div class="vector-toc-text"> 5.1.1 Marker semisynthesis </div> </a> <ul id="toc-Marker_semisynthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Soy_semisynthesis" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Soy_semisynthesis"> <div class="vector-toc-text"> 5.1.2 Soy semisynthesis </div> </a> <ul id="toc-Soy_semisynthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Total_synthesis" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Total_synthesis"> <div class="vector-toc-text"> 5.1.3 Total synthesis </div> </a> <ul id="toc-Total_synthesis-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> 6 History </div> </a> <button aria-controls="toc-History-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle History subsection </button> <ul id="toc-History-sublist" class="vector-toc-list"> <li id="toc-Veterinary_use" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Veterinary_use"> <div class="vector-toc-text"> 6.1 Veterinary use </div> </a> <ul id="toc-Veterinary_use-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pricing" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pricing"> <div class="vector-toc-text"> 6.2 Pricing </div> </a> <ul id="toc-Pricing-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> 7 References </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"> 8 External links </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" > Toggle the table of contents </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading">Progesterone</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 58 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-58" aria-hidden="true" > 58 languages </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A8%D8%B1%D9%88%D8%AC%D8%B3%D8%AA%D9%8A%D8%B1%D9%88%D9%86" title="بروجستيرون – Arabic" lang="ar" hreflang="ar" data-title="بروجستيرون" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target">العربية</a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Progesteron" title="Progesteron – Azerbaijani" lang="az" hreflang="az" data-title="Progesteron" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target">Azərbaycanca</a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%BE%D8%B1%D9%88%DA%98%D8%B3%D8%AA%D8%B1%D9%88%D9%86" title="پروژسترون – South Azerbaijani" lang="azb" hreflang="azb" data-title="پروژسترون" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target">تۆرکجه</a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%AA%E0%A7%8D%E0%A6%B0%E0%A7%8B%E0%A6%9C%E0%A7%87%E0%A6%B8%E0%A7%8D%E0%A6%9F%E0%A7%87%E0%A6%B0%E0%A6%A8" title="প্রোজেস্টেরন – Bangla" lang="bn" hreflang="bn" data-title="প্রোজেস্টেরন" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target">বাংলা</a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%9F%D1%80%D0%B0%D0%B3%D0%B5%D1%81%D1%82%D1%8D%D1%80%D0%BE%D0%BD" title="Прагестэрон – Belarusian" lang="be" hreflang="be" data-title="Прагестэрон" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target">Беларуская</a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%9F%D1%80%D0%BE%D0%B3%D0%B5%D1%81%D1%82%D0%B5%D1%80%D0%BE%D0%BD" title="Прогестерон – Bulgarian" lang="bg" hreflang="bg" data-title="Прогестерон" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target">Български</a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Progesteron" title="Progesteron – Bosnian" lang="bs" hreflang="bs" data-title="Progesteron" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target">Bosanski</a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Progesterona" title="Progesterona – Catalan" lang="ca" hreflang="ca" data-title="Progesterona" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target">Català</a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Progesteron" title="Progesteron – Czech" lang="cs" hreflang="cs" data-title="Progesteron" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target">Čeština</a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Progesteron" title="Progesteron – Welsh" lang="cy" hreflang="cy" data-title="Progesteron" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target">Cymraeg</a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Progesteron" title="Progesteron – Danish" lang="da" hreflang="da" data-title="Progesteron" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target">Dansk</a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Progesteron" title="Progesteron – German" lang="de" hreflang="de" data-title="Progesteron" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target">Deutsch</a></li><li class="interlanguage-link interwiki-dv mw-list-item"><a href="https://dv.wikipedia.org/wiki/%DE%95%DE%B0%DE%83%DE%AF%DE%96%DE%AC%DE%90%DE%B0%DE%93%DE%A6%DE%83%DE%AF%DE%82%DE%B0" title="ޕްރޯޖެސްޓަރޯން – Divehi" lang="dv" hreflang="dv" data-title="ޕްރޯޖެސްޓަރޯން" data-language-autonym="ދިވެހިބަސް" data-language-local-name="Divehi" class="interlanguage-link-target">ދިވެހިބަސް</a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Progesteroon" title="Progesteroon – Estonian" lang="et" hreflang="et" data-title="Progesteroon" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target">Eesti</a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A0%CF%81%CE%BF%CE%B3%CE%B5%CF%83%CF%84%CE%B5%CF%81%CF%8C%CE%BD%CE%B7" title="Προγεστερόνη – Greek" lang="el" hreflang="el" data-title="Προγεστερόνη" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target">Ελληνικά</a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Progesterona" title="Progesterona – Spanish" lang="es" hreflang="es" data-title="Progesterona" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target">Español</a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Progesterona" title="Progesterona – Basque" lang="eu" hreflang="eu" data-title="Progesterona" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target">Euskara</a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%BE%D8%B1%D9%88%DA%98%D8%B3%D8%AA%D8%B1%D9%88%D9%86" title="پروژسترون – Persian" lang="fa" hreflang="fa" data-title="پروژسترون" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target">فارسی</a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Progest%C3%A9rone" title="Progestérone – French" lang="fr" hreflang="fr" data-title="Progestérone" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target">Français</a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Pr%C3%B3gaist%C3%A9ar%C3%B3n" title="Prógaistéarón – Irish" lang="ga" hreflang="ga" data-title="Prógaistéarón" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target">Gaeilge</a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Proxesterona" title="Proxesterona – Galician" lang="gl" hreflang="gl" data-title="Proxesterona" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target">Galego</a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%99%A9%EC%B2%B4_%ED%98%B8%EB%A5%B4%EB%AA%AC" title="황체 호르몬 – Korean" lang="ko" hreflang="ko" data-title="황체 호르몬" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target">한국어</a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%8A%D6%80%D5%B8%D5%A3%D5%A5%D5%BD%D5%BF%D5%A5%D6%80%D5%B8%D5%B6" title="Պրոգեստերոն – Armenian" lang="hy" hreflang="hy" data-title="Պրոգեստերոն" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target">Հայերեն</a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Progesteron" title="Progesteron – Indonesian" lang="id" hreflang="id" data-title="Progesteron" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target">Bahasa Indonesia</a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Progesterone" title="Progesterone – Italian" lang="it" hreflang="it" data-title="Progesterone" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target">Italiano</a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A4%D7%A8%D7%95%D7%92%D7%A1%D7%98%D7%A8%D7%95%D7%9F" title="פרוגסטרון – Hebrew" lang="he" hreflang="he" data-title="פרוגסטרון" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target">עברית</a></li><li class="interlanguage-link interwiki-ku mw-list-item"><a href="https://ku.wikipedia.org/wiki/Procesteron" title="Procesteron – Kurdish" lang="ku" hreflang="ku" data-title="Procesteron" data-language-autonym="Kurdî" data-language-local-name="Kurdish" class="interlanguage-link-target">Kurdî</a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%9F%D1%80%D0%BE%D0%B3%D0%B5%D1%81%D1%82%D0%B5%D1%80%D0%BE%D0%BD" title="Прогестерон – Kyrgyz" lang="ky" hreflang="ky" data-title="Прогестерон" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target">Кыргызча</a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Progesteronas" title="Progesteronas – Lithuanian" lang="lt" hreflang="lt" data-title="Progesteronas" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target">Lietuvių</a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/S%C3%A1rgatesthormon" title="Sárgatesthormon – Hungarian" lang="hu" hreflang="hu" data-title="Sárgatesthormon" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target">Magyar</a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%9F%D1%80%D0%BE%D0%B3%D0%B5%D1%81%D1%82%D0%B5%D1%80%D0%BE%D0%BD" title="Прогестерон – Macedonian" lang="mk" hreflang="mk" data-title="Прогестерон" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target">Македонски</a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%AA%E0%B5%8D%E0%B4%B0%E0%B5%8A%E0%B4%9C%E0%B4%B8%E0%B5%8D%E0%B4%B1%E0%B5%8D%E0%B4%B1%E0%B4%BF%E0%B4%B1%E0%B5%8B%E0%B5%BA" title="പ്രൊജസ്റ്റിറോൺ – Malayalam" lang="ml" hreflang="ml" data-title="പ്രൊജസ്റ്റിറോൺ" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target">മലയാളം</a></li><li class="interlanguage-link interwiki-mr mw-list-item"><a href="https://mr.wikipedia.org/wiki/%E0%A4%AA%E0%A5%8D%E0%A4%B0%E0%A5%8B%E0%A4%9C%E0%A5%87%E0%A4%B8%E0%A5%8D%E0%A4%9F%E0%A5%87%E0%A4%B0%E0%A5%89%E0%A4%A8" title="प्रोजेस्टेरॉन – Marathi" lang="mr" hreflang="mr" data-title="प्रोजेस्टेरॉन" data-language-autonym="मराठी" data-language-local-name="Marathi" class="interlanguage-link-target">मराठी</a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Progesteron" title="Progesteron – Dutch" lang="nl" hreflang="nl" data-title="Progesteron" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target">Nederlands</a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%97%E3%83%AD%E3%82%B2%E3%82%B9%E3%83%86%E3%83%AD%E3%83%B3" title="プロゲステロン – Japanese" lang="ja" hreflang="ja" data-title="プロゲステロン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target">日本語</a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Progesteron" title="Progesteron – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Progesteron" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target">Norsk bokmål</a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Progesterona" title="Progesterona – Occitan" lang="oc" hreflang="oc" data-title="Progesterona" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target">Occitan</a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Progesteron" title="Progesteron – Uzbek" lang="uz" hreflang="uz" data-title="Progesteron" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target">Oʻzbekcha / ўзбекча</a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Progesteron" title="Progesteron – Polish" lang="pl" hreflang="pl" data-title="Progesteron" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target">Polski</a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Progesterona" title="Progesterona – Portuguese" lang="pt" hreflang="pt" data-title="Progesterona" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target">Português</a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Progesteron" title="Progesteron – Romanian" lang="ro" hreflang="ro" data-title="Progesteron" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target">Română</a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9F%D1%80%D0%BE%D0%B3%D0%B5%D1%81%D1%82%D0%B5%D1%80%D0%BE%D0%BD" title="Прогестерон – Russian" lang="ru" hreflang="ru" data-title="Прогестерон" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target">Русский</a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Progesterone" title="Progesterone – Simple English" lang="en-simple" hreflang="en-simple" data-title="Progesterone" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target">Simple English</a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Progester%C3%B3n" title="Progesterón – Slovak" lang="sk" hreflang="sk" data-title="Progesterón" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target">Slovenčina</a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Progesteron" title="Progesteron – Slovenian" lang="sl" hreflang="sl" data-title="Progesteron" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target">Slovenščina</a></li><li class="interlanguage-link interwiki-ckb mw-list-item"><a href="https://ckb.wikipedia.org/wiki/%D9%BE%DA%95%DB%86%D8%AC%DB%8E%D8%B3%D8%AA%D8%B1%DB%86%D9%86" title="پڕۆجێسترۆن – Central Kurdish" lang="ckb" hreflang="ckb" data-title="پڕۆجێسترۆن" data-language-autonym="کوردی" data-language-local-name="Central Kurdish" class="interlanguage-link-target">کوردی</a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Progesteron" title="Progesteron – Serbian" lang="sr" hreflang="sr" data-title="Progesteron" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target">Српски / srpski</a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Progesteron" title="Progesteron – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Progesteron" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target">Srpskohrvatski / српскохрватски</a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Keltarauhashormoni" title="Keltarauhashormoni – Finnish" lang="fi" hreflang="fi" data-title="Keltarauhashormoni" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target">Suomi</a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Progesteron" title="Progesteron – Swedish" lang="sv" hreflang="sv" data-title="Progesteron" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target">Svenska</a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%AA%E0%AF%81%E0%AE%B0%E0%AF%8B%E0%AE%9C%E0%AF%86%E0%AE%B8%E0%AF%8D%E0%AE%9F%E0%AE%BF%E0%AE%B0%E0%AF%8B%E0%AE%A9%E0%AF%8D" title="புரோஜெஸ்டிரோன் – Tamil" lang="ta" hreflang="ta" data-title="புரோஜெஸ்டிரோன்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target">தமிழ்</a></li><li class="interlanguage-link interwiki-te mw-list-item"><a href="https://te.wikipedia.org/wiki/%E0%B0%AA%E0%B1%8D%E0%B0%B0%E0%B1%8A%E0%B0%9C%E0%B1%86%E0%B0%B8%E0%B1%8D%E0%B0%9F%E0%B1%86%E0%B0%B0%E0%B0%BE%E0%B0%A8%E0%B1%8D" title="ప్రొజెస్టెరాన్ – Telugu" lang="te" hreflang="te" data-title="ప్రొజెస్టెరాన్" data-language-autonym="తెలుగు" data-language-local-name="Telugu" class="interlanguage-link-target">తెలుగు</a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%82%E0%B8%9E%E0%B8%A3%E0%B9%80%E0%B8%88%E0%B8%AA%E0%B9%80%E0%B8%97%E0%B8%AD%E0%B9%82%E0%B8%A3%E0%B8%99" title="โพรเจสเทอโรน – Thai" lang="th" hreflang="th" data-title="โพรเจสเทอโรน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target">ไทย</a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Progesteron" title="Progesteron – Turkish" lang="tr" hreflang="tr" data-title="Progesteron" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target">Türkçe</a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9F%D1%80%D0%BE%D0%B3%D0%B5%D1%81%D1%82%D0%B5%D1%80%D0%BE%D0%BD" title="Прогестерон – Ukrainian" lang="uk" hreflang="uk" data-title="Прогестерон" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target">Українська</a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Progesterone" title="Progesterone – Vietnamese" lang="vi" hreflang="vi" data-title="Progesterone" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target">Tiếng Việt</a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E9%BB%83%E9%AB%94%E7%B4%A0" title="黃體素 – Cantonese" lang="yue" hreflang="yue" data-title="黃體素" data-language-autonym="粵語" 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searchaux" style="display:none">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 progesterone as a hormone. For its use as a medication, see <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone (medication)</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1268415487">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> <table class="infobox ib-chembox"> <caption>Progesterone </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center skin-invert" typeof="mw:File"><a href="/wiki/File:Progesterone.svg" class="mw-file-description"><img alt="The chemical structure of progesterone." src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a8/Progesterone.svg/225px-Progesterone.svg.png" decoding="async" width="225" height="166" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a8/Progesterone.svg/338px-Progesterone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a8/Progesterone.svg/450px-Progesterone.svg.png 2x" data-file-width="512" data-file-height="377" /></a><figcaption></figcaption></figure> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Progesterone-3D-balls.png" class="mw-file-description"><img alt="A ball-and-stick model of progesterone." src="//upload.wikimedia.org/wikipedia/commons/thumb/7/73/Progesterone-3D-balls.png/225px-Progesterone-3D-balls.png" decoding="async" width="225" height="149" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/73/Progesterone-3D-balls.png/338px-Progesterone-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/73/Progesterone-3D-balls.png/450px-Progesterone-3D-balls.png 2x" data-file-width="2000" data-file-height="1324" /></a><figcaption></figcaption></figure> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Pregn-4-ene-3,20-dione<a href="#cite_note-Adler-2012-2">[2]</a><a href="#cite_note-ChEBI-17026-3">[3]</a></div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">(1S,3aS,3bS,9aR,9bS,11aS)-1-Acetyl-9a,11a-dimethyl-1,2,3,3a,3b,4,5,8,9,9a,9b,10,11,11a-tetradecahydro-7H-cyclopenta[a]phenanthren-7-one</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">P4;<a href="#cite_note-James2015-1">[1]</a> Pregnenedione</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=57-83-0">57-83-0</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CC%28%3DO%29%5BC%40H%5D1CC%5BC%40%40H%5D2%5BC%40%40%5D1%28CC%5BC%40H%5D3%5BC%40H%5D2CCC4%3DCC%28%3DO%29CC%5BC%40%5D34C%29C">Interactive image</a></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=17026">CHEBI:17026</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL103">ChEMBL103</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.5773.html">5773</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div> </td></tr> <tr> <td><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB00396">DB00396</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard">ECHA InfoCard</a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.318">100.000.318</a> <a href="https://www.wikidata.org/wiki/Q26963#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C00410">C00410</a> <img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" />N</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/5994">5994</a></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/4G7DS2Q64Y">4G7DS2Q64Y</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> (<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID3022370">DTXSID3022370</a> <a href="https://www.wikidata.org/wiki/Q26963#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C21H30O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12,16-19H,4-11H2,1-3H3/t16-,17+,18-,19-,20-,21+/m0/s1 <img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" />N</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: RJKFOVLPORLFTN-LEKSSAKUSA-N <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td>C21H30O2 </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>314.469 g/mol </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.171 </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>126 </td></tr> <tr> <td><a href="/wiki/Partition_coefficient" title="Partition coefficient">log P</a> </td> <td>4.04<a href="#cite_note-chemsrc-4">[4]</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Pharmacology </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></div> </td> <td><a href="/wiki/ATC_code_G03" title="ATC code G03">G03DA04</a> (<a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=G03DA04">WHO</a>) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of administration</a></div> </td> <td><a href="/wiki/Oral_administration" title="Oral administration">By mouth</a>, <a href="/wiki/Topical_medication" title="Topical medication">topical</a>/<a href="/wiki/Transdermal" title="Transdermal">transdermal</a>, <a href="/wiki/Intravaginal_administration" title="Intravaginal administration">vaginal</a>, <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">intramuscular injection</a>, <a href="/wiki/Subcutaneous_injection" class="mw-redirect" title="Subcutaneous injection">subcutaneous injection</a>, <a href="/wiki/Implant_(medicine)" title="Implant (medicine)">subcutaneous implant</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetics</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a></div> </td> <td><abbr title="oral micronized progesterone">OMP</abbr>: <10%<a href="#cite_note-pmid12215716-5">[5]</a><a href="#cite_note-pmid8513955-6">[6]</a> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">Protein binding</a></div> </td> <td>• <a href="/wiki/Human_serum_albumin" title="Human serum albumin">Albumin</a>: 80% • <a href="/wiki/Corticosteroid-binding_globulin" class="mw-redirect" title="Corticosteroid-binding globulin">CBG</a>: 18% • <a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin">SHBG</a>: <1% • Free: 1–2%<a href="#cite_note-FritzSperoff2012-7">[7]</a><a href="#cite_note-MarshallD.2008-8">[8]</a> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Metabolism" title="Metabolism">Metabolism</a></div> </td> <td><a href="/wiki/Hepatic" class="mw-redirect" title="Hepatic">Hepatic</a> (<a href="/wiki/CYP2C19" title="CYP2C19">CYP2C19</a>, <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a>, <a href="/wiki/CYP2C9" title="CYP2C9">CYP2C9</a>, <a href="/wiki/5%CE%B1-reductase" class="mw-redirect" title="5α-reductase">5α-reductase</a>, <a href="/wiki/3%CE%B1-hydroxysteroid_dehydrogenase" class="mw-redirect" title="3α-hydroxysteroid dehydrogenase"><abbr title="3α-hydroxysteroid dehydrogenase">3α-HSD</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip 3α-hydroxysteroid dehydrogenase, <a href="/wiki/17%CE%B1-hydroxylase" class="mw-redirect" title="17α-hydroxylase">17α-hydroxylase</a>, <a href="/wiki/21-hydroxylase" class="mw-redirect" title="21-hydroxylase">21-hydroxylase</a>, <a href="/wiki/20%CE%B1-hydroxysteroid_dehydrogenase" class="mw-redirect" title="20α-hydroxysteroid dehydrogenase"><abbr title="20α-hydroxysteroid dehydrogenase">20α-HSD</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip 20α-hydroxysteroid dehydrogenase)<a href="#cite_note-pmid9328296-9">[9]</a><a href="#cite_note-McKayWalters2013-10">[10]</a> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Biological_half-life" title="Biological half-life">Biological half-life</a></div> </td> <td><abbr title="oral micronized progesterone">OMP</abbr>: 16–18 hours<a href="#cite_note-pmid12215716-5">[5]</a><a href="#cite_note-pmid8513955-6">[6]</a><a href="#cite_note-Zutshi-2005-11">[11]</a> <abbr title="Intramuscular">IM</abbr>: 22–26 hours<a href="#cite_note-pmid8513955-6">[6]</a><a href="#cite_note-pmid26342177-12">[12]</a> <abbr title="Subcutaneous">SC</abbr>: 13–18 hours<a href="#cite_note-pmid26342177-12">[12]</a> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Excretion" title="Excretion">Excretion</a></div> </td> <td><a href="/wiki/Renal" class="mw-redirect" title="Renal">Renal</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" />N <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=444066687&page2=Progesterone">verify</a> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y<img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" />N ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> Progesterone (<a href="/wiki/Help:IPA/English" title="Help:IPA/English">/proʊˈdʒɛstəroʊn/</a> <span data-nosnippet="" id="ooui-php-1" class="noexcerpt ext-phonos-PhonosButton ext-phonos-PhonosButton-emptylabel oo-ui-widget oo-ui-widget-enabled oo-ui-buttonElement oo-ui-buttonElement-frameless oo-ui-iconElement oo-ui-buttonWidget" data-ooui="{"_":"mw.Phonos.PhonosButton","href":"\/\/upload.wikimedia.org\/wikipedia\/commons\/transcoded\/2\/21\/LL-Q1860_%28eng%29-Flame%2C_not_lame-progesterone.wav\/LL-Q1860_%28eng%29-Flame%2C_not_lame-progesterone.wav.mp3","rel":["nofollow"],"framed":false,"icon":"volumeUp","data":{"ipa":"","text":"","lang":"en","wikibase":"","file":"LL-Q1860 (eng)-Flame, not lame-progesterone.wav"},"classes":["noexcerpt","ext-phonos-PhonosButton","ext-phonos-PhonosButton-emptylabel"]}"><a role="button" tabindex="0" href="//upload.wikimedia.org/wikipedia/commons/transcoded/2/21/LL-Q1860_%28eng%29-Flame%2C_not_lame-progesterone.wav/LL-Q1860_%28eng%29-Flame%2C_not_lame-progesterone.wav.mp3" rel="nofollow" aria-label="Play audio" title="Play audio" class="oo-ui-buttonElement-button"></a><a href="/wiki/File:LL-Q1860_(eng)-Flame,_not_lame-progesterone.wav" title="File:LL-Q1860 (eng)-Flame, not lame-progesterone.wav">ⓘ</a>; P4) is an <a href="/wiki/Endogenous" class="mw-redirect" title="Endogenous">endogenous</a> <a href="/wiki/Steroid" title="Steroid">steroid</a> and <a href="/wiki/Progestogen" title="Progestogen">progestogen</a> <a href="/wiki/Sex_hormone" title="Sex hormone">sex hormone</a> involved in the <a href="/wiki/Menstrual_cycle" title="Menstrual cycle">menstrual cycle</a>, <a href="/wiki/Pregnancy" title="Pregnancy">pregnancy</a>, and <a href="/wiki/Embryogenesis" class="mw-redirect" title="Embryogenesis">embryogenesis</a> of humans and other species.<a href="#cite_note-James2015-1">[1]</a><a href="#cite_note-KingBrucker2010-13">[13]</a> It belongs to a group of steroid hormones called the <a href="/wiki/Progestogen" title="Progestogen">progestogens</a><a href="#cite_note-KingBrucker2010-13">[13]</a> and is the major progestogen in the body. Progesterone has a variety of important functions in the body. It is also a crucial <a href="/wiki/Metabolic_intermediate" title="Metabolic intermediate">metabolic intermediate</a> in the production of other endogenous <a href="/wiki/Steroid" title="Steroid">steroids</a>, including the <a href="/wiki/Sex_hormone" title="Sex hormone">sex hormones</a> and the <a href="/wiki/Corticosteroid" title="Corticosteroid">corticosteroids</a>, and plays an important role in brain function as a <a href="/wiki/Neurosteroid" title="Neurosteroid">neurosteroid</a>.<a href="#cite_note-pmid11108866-14">[14]</a> In addition to its role as a natural hormone, progesterone is also used as a medication, such as in combination with <a href="/wiki/Estrogen" title="Estrogen">estrogen</a> for <a href="/wiki/Contraception" class="mw-redirect" title="Contraception">contraception</a>, to reduce the risk of <a href="/wiki/Uterine_cancer" title="Uterine cancer">uterine</a> or <a href="/wiki/Cervical_cancer" title="Cervical cancer">cervical cancer</a>, in <a href="/wiki/Hormone_replacement_therapy" title="Hormone replacement therapy">hormone replacement therapy</a>, and in <a href="/wiki/Feminizing_hormone_therapy" title="Feminizing hormone therapy">feminizing hormone therapy</a>.<a href="#cite_note-pmid30608551-15">[15]</a> It was first prescribed in 1934.<a href="#cite_note-Fis2006-16">[16]</a> <style data-mw-deduplicate="TemplateStyles:r886046785">.mw-parser-output .toclimit-2 .toclevel-1 ul,.mw-parser-output .toclimit-3 .toclevel-2 ul,.mw-parser-output .toclimit-4 .toclevel-3 ul,.mw-parser-output .toclimit-5 .toclevel-4 ul,.mw-parser-output .toclimit-6 .toclevel-5 ul,.mw-parser-output .toclimit-7 .toclevel-6 ul{display:none}</style><div class="toclimit-3"><meta property="mw:PageProp/toc" /></div> <div class="mw-heading mw-heading2"><h2 id="Biological_activity">Biological activity</h2>[<a href="/w/index.php?title=Progesterone&action=edit&section=1" title="Edit section: Biological activity">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Pharmacodynamics_of_progesterone#Mechanism_of_action" title="Pharmacodynamics of progesterone">Pharmacodynamics of progesterone § Mechanism of action</a></div> Progesterone is the most important progestogen in the body. As a potent <a href="/wiki/Agonist" title="Agonist">agonist</a> of the <a href="/wiki/Progesterone_receptor" title="Progesterone receptor">nuclear progesterone receptor</a> (nPR) (with an <a href="/wiki/Affinity_(pharmacology)" class="mw-redirect" title="Affinity (pharmacology)">affinity</a> of KD = 1 nM) the resulting effects on ribosomal transcription plays a major role in regulation of female reproduction.<a href="#cite_note-KingBrucker2010-13">[13]</a><a href="#cite_note-Josimovich2013-17">[17]</a> In addition, progesterone is an agonist of the more recently discovered <a href="/wiki/Membrane_progesterone_receptor" title="Membrane progesterone receptor">membrane progesterone receptors</a> (mPRs),<a href="#cite_note-pmid22687885-18">[18]</a> of which the expression has regulation effects in reproduction function (<a href="/wiki/Oocyte_maturation" class="mw-redirect" title="Oocyte maturation">oocyte maturation</a>, labor, and <a href="/wiki/Sperm_motility" title="Sperm motility">sperm motility</a>) and cancer although additional research is required to further define the roles.<a href="#cite_note-pmid27368976-19">[19]</a> It also functions as a ligand of the <a href="/wiki/PGRMC1" title="PGRMC1">PGRMC1</a> (progesterone receptor membrane component 1) which impacts <a href="/wiki/Tumor_progression" title="Tumor progression">tumor progression</a>, metabolic regulation, and viability control of <a href="/wiki/Nerve_cells" class="mw-redirect" title="Nerve cells">nerve cells</a>.<a href="#cite_note-pmid9516722-20">[20]</a><a href="#cite_note-pmid30087538-21">[21]</a><a href="#cite_note-pmid28396637-22">[22]</a> Moreover, progesterone is also known to be an antagonist of the <a href="/wiki/Sigma_receptor" title="Sigma receptor">sigma</a> <a href="/wiki/Sigma-1_receptor" title="Sigma-1 receptor">σ1 receptor</a>,<a href="#cite_note-pmid11744080-23">[23]</a><a href="#cite_note-pmid21084640-24">[24]</a> a <a href="/wiki/Negative_allosteric_modulator" class="mw-redirect" title="Negative allosteric modulator">negative allosteric modulator</a> of <a href="/wiki/Nicotinic_acetylcholine_receptor" title="Nicotinic acetylcholine receptor">nicotinic acetylcholine receptors</a>,<a href="#cite_note-pmid11108866-14">[14]</a> and a potent antagonist of the <a href="/wiki/Mineralocorticoid_receptor" title="Mineralocorticoid receptor">mineralocorticoid receptor</a> (MR).<a href="#cite_note-pmid8282004-25">[25]</a> Progesterone prevents MR activation by binding to this receptor with an affinity exceeding even those of <a href="/wiki/Aldosterone" title="Aldosterone">aldosterone</a> and <a href="/wiki/Glucocorticoid" title="Glucocorticoid">glucocorticoids</a> such as <a href="/wiki/Cortisol" title="Cortisol">cortisol</a> and <a href="/wiki/Corticosterone" title="Corticosterone">corticosterone</a>,<a href="#cite_note-pmid8282004-25">[25]</a> and produces <a href="/wiki/Antimineralocorticoid" class="mw-redirect" title="Antimineralocorticoid">antimineralocorticoid</a> effects, such as <a href="/wiki/Natriuresis" title="Natriuresis">natriuresis</a>, at physiological concentrations.<a href="#cite_note-pmid14667981-26">[26]</a> In addition, progesterone binds to and behaves as a <a href="/wiki/Partial_agonist" title="Partial agonist">partial agonist</a> of the <a href="/wiki/Glucocorticoid_receptor" title="Glucocorticoid receptor">glucocorticoid receptor</a> (GR), albeit with very low potency (<a href="/wiki/EC50" title="EC50">EC50</a> >100-fold less relative to <a href="/wiki/Cortisol" title="Cortisol">cortisol</a>).<a href="#cite_note-pmid18060946-27">[27]</a><a href="#cite_note-pmid23209664-28">[28]</a> Progesterone, through its <a href="/wiki/Neurosteroid" title="Neurosteroid">neurosteroid</a> <a href="/wiki/Active_metabolite" title="Active metabolite">active metabolites</a> such as <a href="/wiki/5%CE%B1-dihydroprogesterone" class="mw-redirect" title="5α-dihydroprogesterone">5α-dihydroprogesterone</a> and <a href="/wiki/Allopregnanolone" title="Allopregnanolone">allopregnanolone</a>, acts indirectly as a <a href="/wiki/Positive_allosteric_modulator" class="mw-redirect" title="Positive allosteric modulator">positive allosteric modulator</a> of the <a href="/wiki/GABAA_receptor" title="GABAA receptor">GABAA receptor</a>.<a href="#cite_note-pmid1347506-29">[29]</a> Progesterone and some of its metabolites, such as <a href="/wiki/5%CE%B2-dihydroprogesterone" class="mw-redirect" title="5β-dihydroprogesterone">5β-dihydroprogesterone</a>, are agonists of the <a href="/wiki/Pregnane_X_receptor" title="Pregnane X receptor">pregnane X receptor</a> (PXR),<a href="#cite_note-pmid12372848-30">[30]</a> albeit weakly so (<a href="/wiki/EC50" title="EC50">EC50</a> >10 μM).<a href="#cite_note-pmid9727070-31">[31]</a> In accordance, progesterone <a href="/wiki/Enzyme_inducer" title="Enzyme inducer">induces</a> several <a href="/wiki/Hepatic" class="mw-redirect" title="Hepatic">hepatic</a> <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> <a href="/wiki/Enzyme" title="Enzyme">enzymes</a>,<a href="#cite_note-Meanwell2014-32">[32]</a> such as <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a>,<a href="#cite_note-LegatoBilezikian2004-33">[33]</a><a href="#cite_note-LemkeWilliams2012_p164-34">[34]</a> especially during <a href="/wiki/Pregnancy" title="Pregnancy">pregnancy</a> when concentrations are much higher than usual.<a href="#cite_note-ScholarlyEditions2013-35">[35]</a> Perimenopausal women have been found to have greater CYP3A4 activity relative to men and postmenopausal women, and it has been inferred that this may be due to the higher progesterone levels present in perimenopausal women.<a href="#cite_note-LegatoBilezikian2004-33">[33]</a> Progesterone modulates the activity of <a href="/wiki/Cation_channels_of_sperm" title="Cation channels of sperm">CatSper</a> (cation channels of sperm) <a href="/wiki/Voltage-gated_ion_channel" title="Voltage-gated ion channel">voltage-gated</a> Ca2+ channels. Since eggs release progesterone, sperm may use progesterone as a homing signal to swim toward eggs (<a href="/wiki/Chemotaxis" title="Chemotaxis">chemotaxis</a>). As a result, it has been suggested that substances that block the progesterone binding site on CatSper channels could potentially be used in <a href="/wiki/Male_contraception" class="mw-redirect" title="Male contraception">male contraception</a>.<a href="#cite_note-pmid21412338-36">[36]</a><a href="#cite_note-pmid21412339-37">[37]</a> <div class="mw-heading mw-heading2"><h2 id="Biological_function">Biological function</h2>[<a href="/w/index.php?title=Progesterone&action=edit&section=2" title="Edit section: Biological function">edit</a>]</div> <figure class="mw-default-size skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Estradiol_and_progesterone_%25_changes_across_the_menstrual_cycle.tif" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/87/Estradiol_and_progesterone_%25_changes_across_the_menstrual_cycle.tif/lossless-page1-340px-Estradiol_and_progesterone_%25_changes_across_the_menstrual_cycle.tif.png" decoding="async" width="340" height="210" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/87/Estradiol_and_progesterone_%25_changes_across_the_menstrual_cycle.tif/lossless-page1-510px-Estradiol_and_progesterone_%25_changes_across_the_menstrual_cycle.tif.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/87/Estradiol_and_progesterone_%25_changes_across_the_menstrual_cycle.tif/lossless-page1-680px-Estradiol_and_progesterone_%25_changes_across_the_menstrual_cycle.tif.png 2x" data-file-width="1522" data-file-height="939" /></a><figcaption>During the menstrual cycle, levels of estradiol (an estrogen) vary by 200 percent. Levels of progesterone vary by over 1200 percent.<a href="#cite_note-Prior-2020-38">[38]</a></figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Hormonal_interactions">Hormonal interactions</h3>[<a href="/w/index.php?title=Progesterone&action=edit&section=3" title="Edit section: Hormonal interactions">edit</a>]</div> Progesterone has a number of physiological effects that are amplified in the presence of <a href="/wiki/Estrogen" title="Estrogen">estrogens</a>. Estrogens through <a href="/wiki/Estrogen_receptor" title="Estrogen receptor">estrogen receptors</a> (ERs) induce or <a href="/wiki/Upregulation" class="mw-redirect" title="Upregulation">upregulate</a> the <a href="/wiki/Gene_expression" title="Gene expression">expression</a> of the PR.<a href="#cite_note-pmid2328727-39">[39]</a> One example of this is in <a href="/wiki/Breast" title="Breast">breast</a> tissue, where estrogens allow progesterone to mediate <a href="/wiki/Lobuloalveolar" class="mw-redirect" title="Lobuloalveolar">lobuloalveolar</a> development.<a href="#cite_note-pmid16917139-40">[40]</a><a href="#cite_note-Johnson2003-41">[41]</a><a href="#cite_note-CoadDunstall2011-42">[42]</a> Elevated levels of progesterone potently reduce the sodium-retaining activity of aldosterone, resulting in natriuresis and a reduction in extracellular fluid volume. Progesterone withdrawal, on the other hand, is associated with a temporary increase in sodium retention (reduced natriuresis, with an increase in extracellular fluid volume) due to the compensatory increase in aldosterone production, which combats the blockade of the mineralocorticoid receptor by the previously elevated level of progesterone.<a href="#cite_note-pmid13263410-43">[43]</a> <div class="mw-heading mw-heading3"><h3 id="Early_sexual_differentiation">Early sexual differentiation</h3>[<a href="/w/index.php?title=Progesterone&action=edit&section=4" title="Edit section: Early sexual differentiation">edit</a>]</div> Progesterone plays a role in early human sexual differentiation.<a href="#cite_note-wj-44">[44]</a> <a href="/wiki/Placenta" title="Placenta">Placental</a> progesterone is the feedstock for the <a href="/wiki/5%CE%B1-dihydrotestosterone" class="mw-redirect" title="5α-dihydrotestosterone">5α-dihydrotestosterone</a> (DHT) produced via the <a href="/wiki/Androgen_backdoor_pathway" title="Androgen backdoor pathway">backdoor pathway</a> found operating in multiple non-gonadal tissues of the <a href="/wiki/Fetus" title="Fetus">fetus</a>,<a href="#cite_note-pmid30763313-45">[45]</a> whereas deficiencies in this pathway lead to undervirilization of the male fetus, resulting in incomplete development of the male genitalia.<a href="#cite_note-pmid24793988-46">[46]</a><a href="#cite_note-pmid8636249-47">[47]</a> DHT is a potent <a href="/wiki/Androgen" title="Androgen">androgen</a> that is responsible for the development of male genitalia, including the <a href="/wiki/Penis" title="Penis">penis</a> and <a href="/wiki/Scrotum" title="Scrotum">scrotum</a>.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] During early fetal development, the undifferentiated gonads can develop into either testes or ovaries. The presence of the <a href="/wiki/Y_chromosome" title="Y chromosome">Y chromosome</a> leads to the development of testes. The testes then produce testosterone, which is converted to DHT via the enzyme <a href="/wiki/5%CE%B1-Reductase" title="5α-Reductase">5α-reductase</a>. DHT is a potent androgen that is responsible for the masculinization of the external genitalia and the development of the prostate gland. Progesterone, produced by the placenta during pregnancy, plays a role in fetal sexual differentiation by serving as a precursor molecule for the synthesis of DHT via the backdoor pathway. In the absence of adequate levels of <a href="/wiki/Steroidogenic_enzymes" class="mw-redirect" title="Steroidogenic enzymes">steroidogenic enzymes</a> during fetal development, the <a href="/wiki/Androgen_backdoor_pathway#Dihydrotestosterone_backdoor_biosynthesis" title="Androgen backdoor pathway">backdoor pathway for DHT synthesis</a> can become deficient, leading to undermasculinization of the male fetus. This can result in the development of ambiguous genitalia or even female genitalia in some cases. Therefore, both DHT and progesterone play crucial roles in early fetal sexual differentiation, with progesterone acting as a precursor molecule for DHT synthesis and DHT promoting the development of male genitalia.<a href="#cite_note-wj-44">[44]</a> <div class="mw-heading mw-heading3"><h3 id="Reproductive_system">Reproductive system</h3>[<a href="/w/index.php?title=Progesterone&action=edit&section=5" title="Edit section: Reproductive system">edit</a>]</div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Endometrium_ocp_use3.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/83/Endometrium_ocp_use3.jpg/220px-Endometrium_ocp_use3.jpg" decoding="async" width="220" height="169" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/83/Endometrium_ocp_use3.jpg/330px-Endometrium_ocp_use3.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/83/Endometrium_ocp_use3.jpg/440px-Endometrium_ocp_use3.jpg 2x" data-file-width="1676" data-file-height="1284" /></a><figcaption><a href="/wiki/Micrograph" title="Micrograph">Micrograph</a> showing changes to the <a href="/wiki/Endometrium" title="Endometrium">endometrium</a> due to progesterone (<a href="/wiki/Decidualization" title="Decidualization">decidualization</a>) <a href="/wiki/H%26E_stain" title="H&E stain">H&E stain</a>.</figcaption></figure> Progesterone has key effects via non-genomic signalling on human sperm as they migrate through the female reproductive tract before <a href="/wiki/Fertilization" class="mw-redirect" title="Fertilization">fertilization</a> occurs, though the receptor(s) as yet remain unidentified.<a href="#cite_note-pmid17447210-48">[48]</a> Detailed characterisation of the events occurring in sperm in response to progesterone has elucidated certain events including intracellular calcium transients and maintained changes,<a href="#cite_note-pmid10837122-49">[49]</a> slow calcium oscillations,<a href="#cite_note-pmid14606954-50">[50]</a> now thought to possibly regulate motility.<a href="#cite_note-pmid15322137-51">[51]</a> It is produced by the ovaries.<a href="#cite_note-Marieb-52">[52]</a> Progesterone has also been shown to demonstrate effects on octopus spermatozoa.<a href="#cite_note-pmid11335951-53">[53]</a> Progesterone is sometimes called the "hormone of <a href="/wiki/Pregnancy" title="Pregnancy">pregnancy</a>",<a href="#cite_note-colostate-54">[54]</a> and it has many roles relating to the development of the fetus: <ul><li>Progesterone converts the <a href="/wiki/Endometrium" title="Endometrium">endometrium</a> to its secretory stage to prepare the uterus for implantation. At the same time progesterone affects the <a href="/wiki/Vaginal_epithelium" title="Vaginal epithelium">vaginal epithelium</a> and <a href="/wiki/Cervix#Cervical_mucus" title="Cervix">cervical mucus</a>, making it thick and impenetrable to <a href="/wiki/Sperm" title="Sperm">sperm</a>. Progesterone is anti-<a href="/wiki/Mitosis" title="Mitosis">mitogenic</a> in endometrial epithelial cells, and as such, mitigates the tropic effects of <a href="/wiki/Estrogen" title="Estrogen">estrogen</a>.<a href="#cite_note-pmid25406186-55">[55]</a> If pregnancy does not occur, progesterone levels will decrease, leading to <a href="/wiki/Menstruate" class="mw-redirect" title="Menstruate">menstruation</a>. Normal menstrual bleeding is progesterone-withdrawal bleeding. If ovulation does not occur and the <a href="/wiki/Corpus_luteum" title="Corpus luteum">corpus luteum</a> does not develop, levels of progesterone may be low, leading to <a href="/wiki/Dysfunctional_uterine_bleeding#Anovulatory_DUB" class="mw-redirect" title="Dysfunctional uterine bleeding">anovulatory dysfunctional uterine bleeding.</a></li> <li>During implantation and <a href="/wiki/Gestation" title="Gestation">gestation</a>, progesterone appears to decrease the maternal <a href="/wiki/Immune_system" title="Immune system">immune</a> response to allow for the acceptance of the pregnancy.<a href="#cite_note-pmid27662646-56">[56]</a></li> <li>Progesterone decreases contractility of the uterine <a href="/wiki/Smooth_muscle" title="Smooth muscle">smooth muscle</a>.<a href="#cite_note-colostate-54">[54]</a> This effect contributes to prevention of <a href="/wiki/Preterm_labor" class="mw-redirect" title="Preterm labor">preterm labor</a>.<a href="#cite_note-pmid27662646-56">[56]</a> Studies have shown that in individuals who are pregnant with a single fetus, asymptomatic in the prenatal stage, and at a high risk of giving pre-term birth spontaneously, vaginal progesterone medication has been found to be effective in preventing spontaneous pre-term birth. Individuals who are at a high risk of giving pre-term birth spontaneously are those who have a short cervix of less than 25 mm or have previously given pre-term birth spontaneously. Although pre-term births are generally considered to be less than 37 weeks, these studies found that vaginal progesterone is associated with fewer pre-term births of less than 34 weeks.<a href="#cite_note-pmid35168930-57">[57]</a></li> <li>A drop in progesterone levels is possibly one step that facilitates the onset of <a href="/wiki/Labor_(childbirth)" class="mw-redirect" title="Labor (childbirth)">labor</a>.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>]</li> <li>In addition, progesterone inhibits <a href="/wiki/Lactation" title="Lactation">lactation</a> during pregnancy. The fall in progesterone levels following delivery is one of the triggers for milk production.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>]</li></ul> The <a href="/wiki/Fetus" title="Fetus">fetus</a> <a href="/wiki/Metabolize" class="mw-redirect" title="Metabolize">metabolizes</a> placental progesterone in the production of <a href="/wiki/Adrenal" class="mw-redirect" title="Adrenal">adrenal</a> steroids.<a href="#cite_note-pmid30763313-45">[45]</a> <div class="mw-heading mw-heading3"><h3 id="Breasts">Breasts</h3>[<a href="/w/index.php?title=Progesterone&action=edit&section=6" title="Edit section: Breasts">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Breast_development#Biochemistry" title="Breast development">Breast development § Biochemistry</a></div> <div class="mw-heading mw-heading4"><h4 id="Lobuloalveolar_development">Lobuloalveolar development</h4>[<a href="/w/index.php?title=Progesterone&action=edit&section=7" title="Edit section: Lobuloalveolar development">edit</a>]</div> Progesterone plays an important role in <a href="/wiki/Breast_development" title="Breast development">breast development</a>. In conjunction with <a href="/wiki/Prolactin" title="Prolactin">prolactin</a>, it mediates <a href="/wiki/Mammary_alveolus" title="Mammary alveolus">lobuloalveolar</a> maturation of the <a href="/wiki/Mammary_gland" title="Mammary gland">mammary glands</a> during pregnancy to allow for milk production and thus <a href="/wiki/Lactation" title="Lactation">lactation</a> and <a href="/wiki/Breastfeeding" title="Breastfeeding">breastfeeding</a> of <a href="/wiki/Offspring" title="Offspring">offspring</a> following <a href="/wiki/Parturition" class="mw-redirect" title="Parturition">parturition</a> (childbirth).<a href="#cite_note-pmid22844349-58">[58]</a> <a href="/wiki/Estrogen" title="Estrogen">Estrogen</a> induces expression of the PR in breast tissue and hence progesterone is dependent on estrogen to mediate lobuloalveolar development.<a href="#cite_note-pmid16917139-40">[40]</a><a href="#cite_note-Johnson2003-41">[41]</a><a href="#cite_note-CoadDunstall2011-42">[42]</a> It has been found that <a href="/wiki/Receptor_activator_of_nuclear_factor_kappa-B_ligand" class="mw-redirect" title="Receptor activator of nuclear factor kappa-B ligand"><abbr title="Receptor activator of nuclear factor kappa-B ligand">RANKL</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 Receptor activator of nuclear factor kappa-B ligand is a critical downstream mediator of progesterone-induced lobuloalveolar maturation.<a href="#cite_note-pmid26266959-59">[59]</a> RANKL <a href="/wiki/Knockout_mice" class="mw-redirect" title="Knockout mice">knockout mice</a> show an almost identical mammary phenotype to PR knockout mice, including normal mammary ductal development but complete failure of the development of lobuloalveolar structures.<a href="#cite_note-pmid26266959-59">[59]</a> <div class="mw-heading mw-heading4"><h4 id="Ductal_development">Ductal development</h4>[<a href="/w/index.php?title=Progesterone&action=edit&section=8" title="Edit section: Ductal development">edit</a>]</div> Though to a far lesser extent than estrogen, which is the major mediator of mammary ductal development (via the <a href="/wiki/Estrogen_receptor_alpha" title="Estrogen receptor alpha">ERα</a>),<a href="#cite_note-StraussBarbieri2013-60">[60]</a><a href="#cite_note-pmid24718936-61">[61]</a> progesterone may be involved in ductal development of the mammary glands to some extent as well.<a href="#cite_note-pmid23705924-62">[62]</a> PR knockout mice or mice treated with the <a href="/wiki/Antiprogestogen" title="Antiprogestogen">PR antagonist</a> <a href="/wiki/Mifepristone" title="Mifepristone">mifepristone</a> show delayed although otherwise normal mammary ductal development at puberty.<a href="#cite_note-pmid23705924-62">[62]</a> In addition, mice modified to have <a href="/wiki/Overexpression" class="mw-redirect" title="Overexpression">overexpression</a> of <a href="/wiki/Progesterone_receptor_A" title="Progesterone receptor A">PRA</a> display ductal hyperplasia,<a href="#cite_note-pmid26266959-59">[59]</a> and progesterone induces ductal growth in the mouse mammary gland.<a href="#cite_note-pmid23705924-62">[62]</a> Progesterone mediates ductal development mainly via induction of the <a href="/wiki/Gene_expression" title="Gene expression">expression</a> of <a href="/wiki/Amphiregulin" title="Amphiregulin">amphiregulin</a>, the same <a href="/wiki/Growth_factor" title="Growth factor">growth factor</a> that estrogen primarily induces the expression of to mediate ductal development.<a href="#cite_note-pmid23705924-62">[62]</a> These animal findings suggest that, while not essential for full mammary ductal development, progesterone seems to play a potentiating or accelerating role in estrogen-mediated mammary ductal development.<a href="#cite_note-pmid23705924-62">[62]</a> <div class="mw-heading mw-heading4"><h4 id="Breast_cancer_risk">Breast cancer risk</h4>[<a href="/w/index.php?title=Progesterone&action=edit&section=9" title="Edit section: Breast cancer risk">edit</a>]</div> Progesterone also appears to be involved in the <a href="/wiki/Pathophysiology" title="Pathophysiology">pathophysiology</a> of <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a>, though its role, and whether it is a promoter or inhibitor of breast cancer risk, has not been fully elucidated.<a href="#cite_note-pmid23336704-63">[63]</a><a href="#cite_note-pmid31512725-64">[64]</a> Most <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestins</a>, or <a href="/wiki/Synthetic_compound" class="mw-redirect" title="Synthetic compound">synthetic</a> progestogens, like <a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">medroxyprogesterone acetate</a>, have been found to increase the risk of breast cancer in postmenopausal people in combination with estrogen as a component of <a href="/wiki/Menopausal_hormone_therapy" class="mw-redirect" title="Menopausal hormone therapy">menopausal hormone therapy</a>.<a href="#cite_note-pmid31474332-65">[65]</a><a href="#cite_note-pmid31512725-64">[64]</a> The combination of natural oral progesterone or the atypical progestin <a href="/wiki/Dydrogesterone" title="Dydrogesterone">dydrogesterone</a> with estrogen has been associated with less risk of breast cancer than progestins plus estrogen.<a href="#cite_note-pmid29384406-66">[66]</a><a href="#cite_note-pmid27456847-67">[67]</a><a href="#cite_note-pmid29852797-68">[68]</a> However, this may simply be an artifact of the low progesterone levels produced with oral progesterone.<a href="#cite_note-pmid23336704-63">[63]</a><a href="#cite_note-pmid29526116-69">[69]</a> More research is needed on the role of progesterone in breast cancer.<a href="#cite_note-pmid31512725-64">[64]</a> <div class="mw-heading mw-heading3"><h3 id="Skin_health">Skin health</h3>[<a href="/w/index.php?title=Progesterone&action=edit&section=10" title="Edit section: Skin health">edit</a>]</div> The <a href="/wiki/Estrogen_receptor" title="Estrogen receptor">estrogen receptor</a>, as well as the <a href="/wiki/Progesterone_receptor" title="Progesterone receptor">progesterone receptor</a>, have been detected in the <a href="/wiki/Human_skin" title="Human skin">skin</a>, including in <a href="/wiki/Keratinocyte" title="Keratinocyte">keratinocytes</a> and <a href="/wiki/Fibroblast" title="Fibroblast">fibroblasts</a>.<a href="#cite_note-pmid12762829-70">[70]</a><a href="#cite_note-pmid16120154-71">[71]</a> At <a href="/wiki/Menopause" title="Menopause">menopause</a> and thereafter, decreased levels of female <a href="/wiki/Sex_hormone" title="Sex hormone">sex hormones</a> result in <a href="/wiki/Atrophy" title="Atrophy">atrophy</a>, thinning, and increased <a href="/wiki/Wrinkling" class="mw-redirect" title="Wrinkling">wrinkling</a> of the skin and a reduction in skin <a href="/wiki/Elasticity_(physics)" title="Elasticity (physics)">elasticity</a>, firmness, and strength.<a href="#cite_note-pmid12762829-70">[70]</a><a href="#cite_note-pmid16120154-71">[71]</a> These skin changes constitute an acceleration in <a href="/wiki/Human_skin#Aging" title="Human skin">skin aging</a> and are the result of decreased <a href="/wiki/Collagen" title="Collagen">collagen</a> content, irregularities in the <a href="/wiki/Morphology_(biology)" title="Morphology (biology)">morphology</a> of <a href="/wiki/Epidermis_(skin)" class="mw-redirect" title="Epidermis (skin)">epidermal</a> <a href="/wiki/Skin_cell" class="mw-redirect" title="Skin cell">skin cells</a>, decreased <a href="/wiki/Ground_substance" title="Ground substance">ground substance</a> between <a href="/wiki/Skin_fiber" class="mw-redirect" title="Skin fiber">skin fibers</a>, and reduced <a href="/wiki/Capillary" title="Capillary">capillaries</a> and <a href="/wiki/Blood_flow" class="mw-redirect" title="Blood flow">blood flow</a>.<a href="#cite_note-pmid12762829-70">[70]</a><a href="#cite_note-pmid16120154-71">[71]</a> The skin also becomes more <a href="/wiki/Dry_skin" class="mw-redirect" title="Dry skin">dry</a> during menopause, which is due to reduced skin <a href="/wiki/Tissue_hydration" title="Tissue hydration">hydration</a> and <a href="/wiki/Sebum" class="mw-redirect" title="Sebum">surface lipids</a> (sebum production).<a href="#cite_note-pmid12762829-70">[70]</a> Along with chronological aging and photoaging, estrogen deficiency in menopause is one of the three main factors that predominantly influences skin aging.<a href="#cite_note-pmid12762829-70">[70]</a> Hormone replacement therapy, consisting of systemic treatment with estrogen alone or in combination with a progestogen, has well-documented and considerable beneficial effects on the skin of postmenopausal people.<a href="#cite_note-pmid12762829-70">[70]</a><a href="#cite_note-pmid16120154-71">[71]</a> These benefits include increased skin collagen content, skin thickness and elasticity, and skin hydration and surface lipids.<a href="#cite_note-pmid12762829-70">[70]</a><a href="#cite_note-pmid16120154-71">[71]</a> Topical estrogen has been found to have similar beneficial effects on the skin.<a href="#cite_note-pmid12762829-70">[70]</a> In addition, a study has found that topical 2% progesterone cream significantly increases skin elasticity and firmness and observably decreases wrinkles in peri- and postmenopausal people.<a href="#cite_note-pmid16120154-71">[71]</a> Skin hydration and surface lipids, on the other hand, did not significantly change with topical progesterone.<a href="#cite_note-pmid16120154-71">[71]</a> These findings suggest that progesterone, like estrogen, also has beneficial effects on the skin, and may be independently protective against skin aging.<a href="#cite_note-pmid16120154-71">[71]</a> <div class="mw-heading mw-heading3"><h3 id="Sexuality">Sexuality</h3>[<a href="/w/index.php?title=Progesterone&action=edit&section=11" title="Edit section: Sexuality">edit</a>]</div> <div class="mw-heading mw-heading4"><h4 id="Libido">Libido</h4>[<a href="/w/index.php?title=Progesterone&action=edit&section=12" title="Edit section: Libido">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Sexual_motivation_and_hormones" class="mw-redirect" title="Sexual motivation and hormones">Sexual motivation and hormones</a></div> Progesterone and its <a href="/wiki/Neurosteroid" title="Neurosteroid">neurosteroid</a> <a href="/wiki/Active_metabolite" title="Active metabolite">active metabolite</a> <a href="/wiki/Allopregnanolone" title="Allopregnanolone">allopregnanolone</a> appear to be importantly involved in <a href="/wiki/Libido" title="Libido">libido</a> in females.<a href="#cite_note-King2012-72">[72]</a> <div class="mw-heading mw-heading4"><h4 id="Homosexuality">Homosexuality</h4>[<a href="/w/index.php?title=Progesterone&action=edit&section=13" title="Edit section: Homosexuality">edit</a>]</div> Dr. <a href="/wiki/Diana_Fleischman" title="Diana Fleischman">Diana Fleischman</a>, of the <a href="/wiki/University_of_Portsmouth" title="University of Portsmouth">University of Portsmouth</a>, and colleagues looked for a relationship between progesterone and sexual attitudes in 92 women. Their research, published in the <a href="/wiki/Archives_of_Sexual_Behavior" title="Archives of Sexual Behavior">Archives of Sexual Behavior</a> found that women who had higher levels of progesterone scored higher on a questionnaire measuring homoerotic motivation. They also found that men who had high levels of progesterone were more likely to have higher homoerotic motivation scores after affiliative priming compared to men with low levels of progesterone.<a href="#cite_note-pmid25420899-73">[73]</a><a href="#cite_note-UoP-News-Homos-74">[74]</a><a href="#cite_note-The-Telegraph-2014-75">[75]</a><a href="#cite_note-HuffPost-2014-76">[76]</a> <div class="mw-heading mw-heading3"><h3 id="Nervous_system">Nervous system</h3>[<a href="/w/index.php?title=Progesterone&action=edit&section=14" title="Edit section: Nervous system">edit</a>]</div> Progesterone, like <a href="/wiki/Pregnenolone" title="Pregnenolone">pregnenolone</a> and <a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">dehydroepiandrosterone</a> (DHEA), belongs to an important group of endogenous steroids called <a href="/wiki/Neurosteroid" title="Neurosteroid">neurosteroids</a>. It can be metabolized within all parts of the <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a>.<a href="#cite_note-pmid558037-77">[77]</a> Neurosteroids are <a href="/wiki/Neuromodulator" class="mw-redirect" title="Neuromodulator">neuromodulators</a>, and are <a href="/wiki/Neuroprotective" class="mw-redirect" title="Neuroprotective">neuroprotective</a>, <a href="/wiki/Neurogenic" class="mw-redirect" title="Neurogenic">neurogenic</a>, and regulate <a href="/wiki/Neurotransmission" title="Neurotransmission">neurotransmission</a> and <a href="/wiki/Myelin" title="Myelin">myelination</a>.<a href="#cite_note-pmid15135772-78">[78]</a> The effects of progesterone as a neurosteroid are mediated predominantly through its interactions with non-nuclear PRs, namely the mPRs and <a href="/wiki/PGRMC1" title="PGRMC1">PGRMC1</a>, as well as certain other receptors, such as the σ1 and nACh receptors.<a href="#cite_note-pmid24065876-79">[79]</a> <div class="mw-heading mw-heading3"><h3 id="Brain_damage">Brain damage</h3>[<a href="/w/index.php?title=Progesterone&action=edit&section=15" title="Edit section: Brain damage">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Progesterone_(medication)#Other_uses" title="Progesterone (medication)">Progesterone (medication) § Other uses</a></div> Previous studies have shown that progesterone supports the normal development of neurons in the brain, and that the hormone has a protective effect on damaged brain tissue. It has been observed in animal models that females have reduced susceptibility to <a href="/wiki/Traumatic_brain_injury" title="Traumatic brain injury">traumatic brain injury</a> and this protective effect has been hypothesized to be caused by increased circulating levels of <a href="/wiki/Estrogen" title="Estrogen">estrogen</a> and progesterone in females.<a href="#cite_note-pmid10833057-80">[80]</a> <div class="mw-heading mw-heading4"><h4 id="Proposed_mechanism">Proposed mechanism</h4>[<a href="/w/index.php?title=Progesterone&action=edit&section=16" title="Edit section: Proposed mechanism">edit</a>]</div> The mechanism of progesterone protective effects may be the reduction of inflammation that follows brain trauma and hemorrhage.<a href="#cite_note-pmid18188998-81">[81]</a><a href="#cite_note-pmid27143417-82">[82]</a> Damage incurred by traumatic brain injury is believed to be caused in part by mass <a href="/wiki/Depolarization" title="Depolarization">depolarization</a> leading to <a href="/wiki/Excitotoxicity" title="Excitotoxicity">excitotoxicity</a>. One way in which progesterone helps to alleviate some of this excitotoxicity is by blocking the <a href="/wiki/Voltage-dependent_calcium_channel" class="mw-redirect" title="Voltage-dependent calcium channel">voltage-dependent calcium channels</a> that trigger <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitter</a> release.<a href="#cite_note-pmid22101209-83">[83]</a> It does so by manipulating the signaling pathways of <a href="/wiki/Transcription_factor" title="Transcription factor">transcription factors</a> involved in this release. Another method for reducing the excitotoxicity is by up-regulating the <a href="/wiki/GABAA_receptor" title="GABAA receptor">GABAA</a>, a widespread inhibitory neurotransmitter receptor.<a href="#cite_note-pmid17826842-84">[84]</a> Progesterone has also been shown to prevent <a href="/wiki/Apoptosis" title="Apoptosis">apoptosis</a> in neurons, a common consequence of brain injury. It does so by inhibiting enzymes involved in the apoptosis pathway specifically concerning the mitochondria, such as activated <a href="/wiki/Caspase_3" title="Caspase 3">caspase 3</a> and <a href="/wiki/Cytochrome_c" title="Cytochrome c">cytochrome c</a>.<a href="#cite_note-pmid22088981-85">[85]</a> Not only does progesterone help prevent further damage, it has also been shown to aid in <a href="/wiki/Neuroregeneration" title="Neuroregeneration">neuroregeneration</a>.<a href="#cite_note-pmid26746666-86">[86]</a> One of the serious effects of traumatic brain injury includes edema. Animal studies show that progesterone treatment leads to a decrease in <a href="/wiki/Edema" title="Edema">edema</a> levels by increasing the concentration of <a href="/wiki/Macrophage" title="Macrophage">macrophages</a> and <a href="/wiki/Microglia" title="Microglia">microglia</a> sent to the injured tissue.<a href="#cite_note-pmid22101209-83">[83]</a><a href="#cite_note-pmid19401954-87">[87]</a> This was observed in the form of reduced leakage from the <a href="/wiki/Blood_brain_barrier" class="mw-redirect" title="Blood brain barrier">blood brain barrier</a> in secondary recovery in progesterone treated rats. In addition, progesterone was observed to have <a href="/wiki/Antioxidant" title="Antioxidant">antioxidant</a> properties, reducing the concentration of <a href="/wiki/Reactive_oxygen_species" title="Reactive oxygen species">oxygen free radicals</a> faster than without.<a href="#cite_note-pmid17826842-84">[84]</a> There is also evidence that the addition of progesterone can also help re<a href="/wiki/Myelin" title="Myelin">myelinate</a> damaged <a href="/wiki/Axons" class="mw-redirect" title="Axons">axons</a> due to trauma, restoring some lost neural signal conduction.<a href="#cite_note-pmid17826842-84">[84]</a> Another way progesterone aids in regeneration includes increasing the circulation of endothelial progenitor cells in the brain. This helps new <a href="/wiki/Vasculature" class="mw-redirect" title="Vasculature">vasculature</a> to grow around scar tissue which helps repair the area of insult.<a href="#cite_note-pmid21534727-88">[88]</a> <div class="mw-heading mw-heading3"><h3 id="Addiction">Addiction</h3>[<a href="/w/index.php?title=Progesterone&action=edit&section=17" title="Edit section: Addiction">edit</a>]</div> Progesterone enhances the function of <a href="/wiki/Serotonin_receptor" class="mw-redirect" title="Serotonin receptor">serotonin receptors</a> in the brain, so an excess or deficit of progesterone has the potential to result in significant neurochemical issues. This provides an explanation for why some people resort to substances that enhance <a href="/wiki/Serotonin" title="Serotonin">serotonin</a> activity such as <a href="/wiki/Nicotine" title="Nicotine">nicotine</a>, <a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">alcohol</a>, and <a href="/wiki/Cannabis_(drug)" title="Cannabis (drug)">cannabis</a> when their progesterone levels fall below optimal levels.<a href="#cite_note-pmid21186920-89">[89]</a> <ul><li>Sex differences in hormone levels may induce women to respond differently than men to nicotine. When women undergo cyclic changes or different hormonal transition phases (menopause, pregnancy, adolescence), there are changes in their progesterone levels.<a href="#cite_note-pmid22474108-90">[90]</a> Therefore, females have an increased biological vulnerability to nicotine's reinforcing effects compared to males and progesterone may be used to counter this enhanced vulnerability. This information supports the idea that progesterone can affect behavior.<a href="#cite_note-pmid21186920-89">[89]</a></li> <li>Similar to nicotine, cocaine also increases the release of dopamine in the brain. The neurotransmitter is involved in the reward center and is one of the main neurotransmitters involved with substance abuse and reliance. In a study of cocaine users, it was reported that progesterone reduced craving and the feeling of being stimulated by cocaine. Thus, progesterone was suggested as an agent that decreases cocaine craving by reducing the dopaminergic properties of the drug.<a href="#cite_note-pmid21796112-91">[91]</a></li></ul> <div class="mw-heading mw-heading3"><h3 id="Societal">Societal</h3>[<a href="/w/index.php?title=Progesterone&action=edit&section=18" title="Edit section: Societal">edit</a>]</div> In a 2012 University of Amsterdam study of 120 women, women's luteal phase (higher levels of progesterone, and increasing levels of estrogen) was correlated with a lower level of competitive behavior in gambling and math contest scenarios, while their premenstrual phase (sharply-decreasing levels of progesterone, and decreasing levels of estrogen) was correlated with a higher level of competitive behavior.<a href="#cite_note-Buser-2012-92">[92]</a> <div class="mw-heading mw-heading3"><h3 id="Other_effects">Other effects</h3>[<a href="/w/index.php?title=Progesterone&action=edit&section=19" title="Edit section: Other effects">edit</a>]</div> <ul><li>Progesterone also has a role in skin elasticity and bone strength, in <a href="/wiki/Respiration_(physiology)" title="Respiration (physiology)">respiration</a>, in nerve tissue and in <a href="/wiki/Female_sexuality" class="mw-redirect" title="Female sexuality">female sexuality</a>, and the presence of progesterone receptors in certain muscle and fat tissue may hint at a role in <a href="/wiki/Sexual_dimorphism" title="Sexual dimorphism">sexually dimorphic</a> proportions of those.<a href="#cite_note-medicinalchem-93">[93]</a></li> <li>During pregnancy, progesterone is said to decrease uterine irritability.<a href="#cite_note-Blackburn2014-94">[94]</a></li> <li>During pregnancy, progesterone helps to suppress immune responses of the mother to fetal antigens, which prevents rejection of the fetus.<a href="#cite_note-Blackburn2014-94">[94]</a></li> <li>Progesterone raises <a href="/wiki/Epidermal_growth_factor-1" class="mw-redirect" title="Epidermal growth factor-1">epidermal growth factor-1</a> (EGF-1) levels, a factor often used to induce proliferation, and used to sustain cultures, of <a href="/wiki/Stem_cell" title="Stem cell">stem cells</a>.<a href="#cite_note-pmid17074804-95">[95]</a></li> <li>Progesterone increases core temperature (thermogenic function) during ovulation.<a href="#cite_note-GeorgiaPhysiology-96">[96]</a><a href="#cite_note-Rothchild-1969-97">[97]</a></li> <li>Progesterone reduces <a href="/wiki/Spasm" title="Spasm">spasm</a> and relaxes <a href="/wiki/Smooth_muscle" title="Smooth muscle">smooth muscle</a>. <a href="/wiki/Bronchi" class="mw-redirect" title="Bronchi">Bronchi</a> are widened and <a href="/wiki/Mucus" title="Mucus">mucus</a> regulated. (PRs are widely present in <a href="/wiki/Mucous_membrane" title="Mucous membrane">submucosal tissue</a>.)[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>]</li> <li>Progesterone acts as an <a href="/wiki/Inflammation" title="Inflammation">antiinflammatory</a> agent and regulates the <a href="/wiki/Immune_response" title="Immune response">immune response</a>.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>]</li> <li>Progesterone reduces <a href="/wiki/Gall-bladder" class="mw-redirect" title="Gall-bladder">gall-bladder</a> activity.<a href="#cite_note-pmid3184927-98">[98]</a></li> <li>Progesterone normalizes <a href="/wiki/Blood" title="Blood">blood</a> clotting and vascular tone, <a href="/wiki/Zinc" title="Zinc">zinc</a> and <a href="/wiki/Copper" title="Copper">copper</a> levels, <a href="/wiki/Cell_(biology)" title="Cell (biology)">cell</a> <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> levels, and use of fat stores for energy.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>]</li> <li>Progesterone may affect gum health, increasing risk of gingivitis (gum inflammation).<a href="#cite_note-WebMD-Hormones-Oral-Health-99">[99]</a></li> <li>Progesterone appears to prevent <a href="/wiki/Endometrial_cancer" title="Endometrial cancer">endometrial cancer</a> (involving the uterine lining) by regulating the effects of estrogen.</li> <li>Progesterone plays an important role in the signaling of insulin release and pancreatic function, and may affect the susceptibility to diabetes or gestational diabetes.<a href="#cite_note-pmid12438645-100">[100]</a><a href="#cite_note-pmid12591170-101">[101]</a></li> <li>Progesterone levels in the blood were found to be lower in those who had higher weight and higher BMI among those who became pregnant through in vitro fertilization.<a href="#cite_note-pmid34278354-102">[102]</a></li> <li>Current data shows that micronized progesterone, which is chemically identical to the progesterone produced in people's bodies, in combination with estrogen in menopausal hormone therapy does not seem to have significant effects on venous thromboembolism (blood clots in veins) and ischemic stroke (lack of blood flow to the brain due to blockage of a blood vessel that supplies the brain). However, more studies need to be conducted to see whether or not micronized progesterone alone or in combined menopausal hormone therapy changes the risk of myocardial infarctions (heart attacks).<a href="#cite_note-pmid35112635-103">[103]</a></li> <li>There have not been any studies done yet on the effects of micronized progesterone on hair loss due to menopause.<a href="#cite_note-pmid33527841-104">[104]</a></li> <li>Despite suggestions for using hormone therapy to prevent loss of muscle mass in post-menopausal individuals (50 and older), menopausal hormone therapy involving either estrogen alone or estrogen and progesterone has not been found to preserve muscle mass.<a href="#cite_note-pmid31461147-105">[105]</a> Menopausal hormone therapy also does not result in body weight reduction, BMI reduction, or change in glucose metabolism.<a href="#cite_note-pmid30477366-106">[106]</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="Biochemistry">Biochemistry</h2>[<a href="/w/index.php?title=Progesterone&action=edit&section=20" title="Edit section: Biochemistry">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Biosynthesis">Biosynthesis</h3>[<a href="/w/index.php?title=Progesterone&action=edit&section=21" title="Edit section: Biosynthesis">edit</a>]</div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Steroidogenesis.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/13/Steroidogenesis.svg/400px-Steroidogenesis.svg.png" decoding="async" width="400" height="355" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/13/Steroidogenesis.svg/600px-Steroidogenesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/13/Steroidogenesis.svg/800px-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 progesterone among the progestogens in yellow area.<a href="#cite_note-HäggströmRichfield2014-107">[107]</a></figcaption></figure> In mammals, progesterone, like all other <a href="/wiki/Steroid" title="Steroid">steroid</a> <a href="/wiki/Hormone" title="Hormone">hormones</a>, is synthesized from <a href="/wiki/Pregnenolone" title="Pregnenolone">pregnenolone</a>, which itself is derived from <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a>.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] Cholesterol undergoes double oxidation to produce <a href="/wiki/22R-hydroxycholesterol" class="mw-redirect" title="22R-hydroxycholesterol">22R-hydroxycholesterol</a> and then <a href="/wiki/20%CE%B1,22R-dihydroxycholesterol" class="mw-redirect" title="20α,22R-dihydroxycholesterol">20α,22R-dihydroxycholesterol</a>. This vicinal <a href="/wiki/Diol" title="Diol">diol</a> is then further oxidized with loss of the side chain starting at position C22 to produce pregnenolone. This reaction is catalyzed by <a href="/wiki/Cytochrome" title="Cytochrome">cytochrome</a> <a href="/wiki/P450scc" class="mw-redirect" title="P450scc">P450scc</a>.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] The conversion of pregnenolone to progesterone takes place in two steps. First, the 3β-<a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> group is oxidized to a <a href="/wiki/Ketone" title="Ketone">keto</a> group and second, the <a href="/wiki/Double_bond" title="Double bond">double bond</a> is moved to C4, from C5 through a keto/<a href="/wiki/Enol" title="Enol">enol</a> <a href="/wiki/Tautomer" title="Tautomer">tautomerization</a> reaction.<a href="#cite_note-isbn0-471-49641-3-108">[108]</a> This reaction is catalyzed by <a href="/wiki/3%CE%B2-hydroxysteroid_dehydrogenase" class="mw-redirect" title="3β-hydroxysteroid dehydrogenase">3β-hydroxysteroid dehydrogenase/δ5-4-isomerase</a>.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] Progesterone in turn is the precursor of the mineralocorticoid <a href="/wiki/Aldosterone" title="Aldosterone">aldosterone</a>, and after conversion to <a href="/wiki/17%CE%B1-hydroxyprogesterone" class="mw-redirect" title="17α-hydroxyprogesterone">17α-hydroxyprogesterone</a>, of <a href="/wiki/Cortisol" title="Cortisol">cortisol</a> and <a href="/wiki/Androstenedione" title="Androstenedione">androstenedione</a>. Androstenedione can be converted to <a href="/wiki/Testosterone" title="Testosterone">testosterone</a>, <a href="/wiki/Estrone" title="Estrone">estrone</a>, and <a href="/wiki/Estradiol" title="Estradiol">estradiol</a>, highlighting the critical role of progesterone in testosterone synthesis.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] Pregnenolone and progesterone can also be synthesized by <a href="/wiki/Yeast" title="Yeast">yeast</a>.<a href="#cite_note-pmid9487528-109">[109]</a> Approximately 25 mg of progesterone is secreted from the ovaries per day, while the adrenal glands produce about 2 mg of progesterone per day.<a href="#cite_note-LemkeWilliams2012_p1397-110">[110]</a> <table class="wikitable mw-collapsible mw-collapsed" style="margin: 1em auto;"> <caption class="nowrap"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist 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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: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 phase </th> <th rowspan="2">Blood production rate </th> <th rowspan="2">Gonadal secretion rate </th> <th rowspan="2">Metabolic 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">Progesterone </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=""> Notes: "The concentration 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 secretion rate 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 metabolic clearance rate of a steroid is defined as the volume of blood that has been completely cleared of the hormone per unit time. The production rate 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." Sources: See template.</div></div> </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Distribution">Distribution</h3>[<a href="/w/index.php?title=Progesterone&action=edit&section=22" title="Edit section: Distribution">edit</a>]</div> Progesterone binds extensively to <a href="/wiki/Plasma_protein" title="Plasma protein">plasma proteins</a>, including <a href="/wiki/Albumin" title="Albumin">albumin</a> (50–54%) and <a href="/wiki/Transcortin" title="Transcortin">transcortin</a> (43–48%).<a href="#cite_note-Drugs.com-111">[111]</a> It has similar affinity for albumin relative to the PR.<a href="#cite_note-Josimovich2013-17">[17]</a> <div class="mw-heading mw-heading3"><h3 id="Metabolism">Metabolism</h3>[<a href="/w/index.php?title=Progesterone&action=edit&section=23" title="Edit section: Metabolism">edit</a>]</div> The <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> of progesterone is rapid and extensive and occurs mainly in the <a href="/wiki/Liver" title="Liver">liver</a>,<a href="#cite_note-FalconeHurd2007-112">[112]</a><a href="#cite_note-Cupps1991-113">[113]</a><a href="#cite_note-pmid14667980-114">[114]</a> though <a href="/wiki/Enzyme" title="Enzyme">enzymes</a> that metabolize progesterone are also expressed widely in the <a href="/wiki/Brain" title="Brain">brain</a>, <a href="/wiki/Skin" title="Skin">skin</a>, and various other <a href="https://en.wiktionary.org/wiki/extrahepatic" class="extiw" title="wikt:extrahepatic">extrahepatic</a> <a href="/wiki/Tissue_(biology)" title="Tissue (biology)">tissues</a>.<a href="#cite_note-pmid558037-77">[77]</a><a href="#cite_note-DowdJohnson2016-115">[115]</a> Progesterone has an <a href="/wiki/Elimination_half-life" class="mw-redirect" title="Elimination half-life">elimination half-life</a> of only approximately 5 minutes in <a href="/wiki/Circulatory_system" title="Circulatory system">circulation</a>.<a href="#cite_note-FalconeHurd2007-112">[112]</a> The metabolism of progesterone is complex, and it may form as many as 35 different <a href="/wiki/Conjugation_(biochemistry)" class="mw-redirect" title="Conjugation (biochemistry)">unconjugated</a> <a href="/wiki/Metabolite" title="Metabolite">metabolites</a> when it is ingested orally.<a href="#cite_note-pmid14667980-114">[114]</a><a href="#cite_note-pmid16112947-116">[116]</a> Progesterone is highly susceptible to enzymatic <a href="/wiki/Redox" title="Redox">reduction</a> via <a href="/wiki/Reductase" class="mw-redirect" title="Reductase">reductases</a> and <a href="/wiki/Hydroxysteroid_dehydrogenase" title="Hydroxysteroid dehydrogenase">hydroxysteroid dehydrogenases</a> due to its <a href="/wiki/Double_bond" title="Double bond">double bond</a> (between the C4 and C5 positions) and its two <a href="/wiki/Ketone" title="Ketone">ketones</a> (at the C3 and C20 positions).<a href="#cite_note-pmid14667980-114">[114]</a> The major <a href="/wiki/Metabolic_pathway" title="Metabolic pathway">metabolic pathway</a> of progesterone is reduction by <a href="/wiki/5%CE%B1-reductase" class="mw-redirect" title="5α-reductase">5α-reductase</a><a href="#cite_note-pmid558037-77">[77]</a> and <a href="/wiki/5%CE%B2-reductase" class="mw-redirect" title="5β-reductase">5β-reductase</a> into the dihydrogenated <a href="/wiki/5%CE%B1-dihydroprogesterone" class="mw-redirect" title="5α-dihydroprogesterone">5α-dihydroprogesterone</a> and <a href="/wiki/5%CE%B2-dihydroprogesterone" class="mw-redirect" title="5β-dihydroprogesterone">5β-dihydroprogesterone</a>, respectively.<a href="#cite_note-Cupps1991-113">[113]</a><a href="#cite_note-pmid14667980-114">[114]</a><a href="#cite_note-PlantZeleznik2014-117">[117]</a><a href="#cite_note-SantoroNeal-Perry2010-118">[118]</a> This is followed by the further reduction of these metabolites via <a href="/wiki/3%CE%B1-hydroxysteroid_dehydrogenase" class="mw-redirect" title="3α-hydroxysteroid dehydrogenase">3α-hydroxysteroid dehydrogenase</a> and <a href="/wiki/3%CE%B2-hydroxysteroid_dehydrogenase" class="mw-redirect" title="3β-hydroxysteroid dehydrogenase">3β-hydroxysteroid dehydrogenase</a> into the tetrahydrogenated <a href="/wiki/Allopregnanolone" title="Allopregnanolone">allopregnanolone</a>, <a href="/wiki/Pregnanolone" title="Pregnanolone">pregnanolone</a>, <a href="/wiki/Isopregnanolone" title="Isopregnanolone">isopregnanolone</a>, and <a href="/wiki/Epipregnanolone" title="Epipregnanolone">epipregnanolone</a>.<a href="#cite_note-pmid21094889-119">[119]</a><a href="#cite_note-Cupps1991-113">[113]</a><a href="#cite_note-pmid14667980-114">[114]</a><a href="#cite_note-PlantZeleznik2014-117">[117]</a> Subsequently, <a href="/wiki/20%CE%B1-hydroxysteroid_dehydrogenase" class="mw-redirect" title="20α-hydroxysteroid dehydrogenase">20α-hydroxysteroid dehydrogenase</a> and <a href="/wiki/20%CE%B2-hydroxysteroid_dehydrogenase" class="mw-redirect" title="20β-hydroxysteroid dehydrogenase">20β-hydroxysteroid dehydrogenase</a> reduce these metabolites to form the corresponding hexahydrogenated <a href="/wiki/Pregnanediol" title="Pregnanediol">pregnanediols</a> (eight different <a href="/wiki/Isomer" title="Isomer">isomers</a> in total),<a href="#cite_note-Cupps1991-113">[113]</a><a href="#cite_note-SantoroNeal-Perry2010-118">[118]</a> which are then conjugated via <a href="/wiki/Glucuronidation" title="Glucuronidation">glucuronidation</a> and/or <a href="/wiki/Sulfation" title="Sulfation">sulfation</a>, released from the liver into circulation, and <a href="/wiki/Excretion" title="Excretion">excreted</a> by the <a href="/wiki/Kidney" title="Kidney">kidneys</a> into the <a href="/wiki/Urine" title="Urine">urine</a>.<a href="#cite_note-FalconeHurd2007-112">[112]</a><a href="#cite_note-pmid14667980-114">[114]</a> The major metabolite of progesterone in the urine is the 3α,5β,20α isomer of <a href="/wiki/Pregnanediol_glucuronide" title="Pregnanediol glucuronide">pregnanediol glucuronide</a>, which has been found to constitute 15 to 30% of an injection of progesterone.<a href="#cite_note-Josimovich2013-17">[17]</a><a href="#cite_note-BaulieuKelly1990-120">[120]</a> Other metabolites of progesterone formed by the enzymes in this pathway include <a href="/wiki/3%CE%B1-dihydroprogesterone" class="mw-redirect" title="3α-dihydroprogesterone">3α-dihydroprogesterone</a>, <a href="/wiki/3%CE%B2-dihydroprogesterone" class="mw-redirect" title="3β-dihydroprogesterone">3β-dihydroprogesterone</a>, <a href="/wiki/20%CE%B1-dihydroprogesterone" class="mw-redirect" title="20α-dihydroprogesterone">20α-dihydroprogesterone</a>, and <a href="/wiki/20%CE%B2-dihydroprogesterone" class="mw-redirect" title="20β-dihydroprogesterone">20β-dihydroprogesterone</a>, as well as various combination products of the enzymes aside from those already mentioned.<a href="#cite_note-Josimovich2013-17">[17]</a><a href="#cite_note-pmid14667980-114">[114]</a><a href="#cite_note-BaulieuKelly1990-120">[120]</a><a href="#cite_note-pmid21182831-121">[121]</a> Progesterone can also first be <a href="/wiki/Hydroxylation" title="Hydroxylation">hydroxylated</a> (see below) and then reduced.<a href="#cite_note-pmid14667980-114">[114]</a> Endogenous progesterone is metabolized approximately 50% into 5α-dihydroprogesterone in the <a href="/wiki/Corpus_luteum" title="Corpus luteum">corpus luteum</a>, 35% into 3β-dihydroprogesterone in the liver, and 10% into 20α-dihydroprogesterone.<a href="#cite_note-pmid15492972-122">[122]</a> Relatively small portions of progesterone are <a href="/wiki/Hydroxylation" title="Hydroxylation">hydroxylated</a> via <a href="/wiki/17%CE%B1-hydroxylase" class="mw-redirect" title="17α-hydroxylase">17α-hydroxylase</a> (CYP17A1) and <a href="/wiki/21-hydroxylase" class="mw-redirect" title="21-hydroxylase">21-hydroxylase</a> (CYP21A2) into <a href="/wiki/17%CE%B1-hydroxyprogesterone" class="mw-redirect" title="17α-hydroxyprogesterone">17α-hydroxyprogesterone</a> and <a href="/wiki/11-deoxycorticosterone" class="mw-redirect" title="11-deoxycorticosterone">11-deoxycorticosterone</a> (21-hydroxyprogesterone), respectively,<a href="#cite_note-pmid16112947-116">[116]</a> and <a href="/wiki/Pregnanetriol" title="Pregnanetriol">pregnanetriols</a> are formed secondarily to 17α-hydroxylation.<a href="#cite_note-GreenblattBrogan2016-123">[123]</a><a href="#cite_note-Graham2012-124">[124]</a> Even smaller amounts of progesterone may be also hydroxylated via <a href="/wiki/11%CE%B2-hydroxylase" class="mw-redirect" title="11β-hydroxylase">11β-hydroxylase</a> (CYP11B1) and to a lesser extent via <a href="/wiki/Aldosterone_synthase" title="Aldosterone synthase">aldosterone synthase</a> (CYP11B2) into <a href="/wiki/11%CE%B2-hydroxyprogesterone" class="mw-redirect" title="11β-hydroxyprogesterone">11β-hydroxyprogesterone</a>.<a href="#cite_note-pmid23322723-125">[125]</a><a href="#cite_note-pmid29277707-126">[126]</a><a href="#cite_note-wj-44">[44]</a> In addition, progesterone can be hydroxylated in the liver by other <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> enzymes which are not steroid-specific.<a href="#cite_note-Piccinato2008-127">[127]</a> 6β-Hydroxylation, which is catalyzed mainly by <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a>, is the major transformation, and is responsible for approximately 70% of cytochrome P450-mediated progesterone metabolism.<a href="#cite_note-Piccinato2008-127">[127]</a> Other routes include 6α-, 16α-, and 16β-hydroxylation.<a href="#cite_note-pmid14667980-114">[114]</a> However, treatment of women with <a href="/wiki/Ketoconazole" title="Ketoconazole">ketoconazole</a>, a strong CYP3A4 inhibitor, had minimal effects on progesterone levels, producing only a slight and non-significant increase, and this suggests that cytochrome P450 enzymes play only a small role in progesterone metabolism.<a href="#cite_note-pmid1825737-128">[128]</a> <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:752px;"> <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:Progesterone_metabolism" title="Template:Progesterone metabolism"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Progesterone_metabolism" title="Template talk:Progesterone metabolism"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Progesterone_metabolism" title="Special:EditPage/Template:Progesterone metabolism"><abbr title="Edit this template">e</abbr></a></li></ul></div> <a href="/wiki/Metabolic_pathway" title="Metabolic pathway">Metabolism</a> of progesterone in humans<a href="#cite_note-pmid945344-129">[129]</a></div> <div class="skin-invert" style="position:relative; width:750px; height:506px; overflow:hidden; border:solid #ccc 1px; background-color:white;"> <div style="left:0px; top:0px; width:750px; position:absolute"> <img alt="Progesterone metabolism" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0b/Progesterone_metabolism_no_labels.png/750px-Progesterone_metabolism_no_labels.png" decoding="async" width="750" height="507" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0b/Progesterone_metabolism_no_labels.png/1125px-Progesterone_metabolism_no_labels.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0b/Progesterone_metabolism_no_labels.png/1500px-Progesterone_metabolism_no_labels.png 2x" data-file-width="3700" data-file-height="2500" /> </div> <div style="text-align:center; font-size:14px; line-height:110%"> <div style="background-color:transparent; color:black"><div id="annotation_334x110" style="position:absolute; left:334px; top:110px; line-height:110%;">Progesterone</div> <div id="annotation_92x118" style="position:absolute; left:92px; top:118px; line-height:110%;"><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone</a></div> <div id="annotation_519x115" style="position:absolute; left:519px; top:115px; line-height:110%;"><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone</a></div> <div id="annotation_35x275" style="position:absolute; left:35px; top:275px; line-height:110%;"><a href="/wiki/Pregnanetriols" class="mw-redirect" title="Pregnanetriols">Pregnanetriols</a> (8 isomers)</div> <div id="annotation_163x273" style="position:absolute; left:163px; top:273px; line-height:110%;"><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">5α-Dihydroprogesterone</a></div> <div id="annotation_425x273" style="position:absolute; left:425px; top:273px; line-height:110%;"><a href="/wiki/5%CE%B2-Dihydroprogesterone" title="5β-Dihydroprogesterone">5β-Dihydroprogesterone</a></div> <div id="annotation_68x445" style="position:absolute; left:68px; top:445px; line-height:110%;"><a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone</a></div> <div id="annotation_221x445" style="position:absolute; left:221px; top:445px; line-height:110%;"><a href="/wiki/Isopregnanolone" title="Isopregnanolone">Isopregnanolone</a></div> <div id="annotation_396x442" style="position:absolute; left:396px; top:442px; line-height:110%;"><a href="/wiki/Pregnanolone" title="Pregnanolone">Pregnanolone</a></div> <div id="annotation_535x442" style="position:absolute; left:535px; top:442px; line-height:110%;"><a href="/wiki/Epipregnanolone" title="Epipregnanolone">Epipregnanolone</a></div> <div id="annotation_594x272" style="position:absolute; left:594px; top:272px; line-height:110%;"><a href="/wiki/Pregnanediols" class="mw-redirect" title="Pregnanediols">Pregnanediols</a> (8 isomers)</div> <div id="annotation_224x93" style="position:absolute; left:224px; top:93px; font-size:12px; font-size:12; line-height:14px;"><a href="/wiki/17%CE%B1-Hydroxylase" class="mw-redirect" title="17α-Hydroxylase">17α-Hydroxylase</a></div> <div id="annotation_432x93" style="position:absolute; left:432px; top:93px; font-size:12px; font-size:12; line-height:14px;"><a href="/wiki/21-Hydroxylase" title="21-Hydroxylase">21-Hydroxylase</a></div> <div id="annotation_160x153" style="position:absolute; left:160px; top:153px; font-size:12px; font-size:12; line-height:14px;">Multiple</div> <div id="annotation_224x134" style="position:absolute; left:224px; top:134px; font-size:12px; font-size:12; line-height:14px;"><a href="/wiki/5%CE%B1-Reductase" title="5α-Reductase">5α-Reductase</a></div> <div id="annotation_455x132" style="position:absolute; left:455px; top:132px; font-size:12px; font-size:12; line-height:14px;"><a href="/wiki/5%CE%B2-Reductase" title="5β-Reductase">5β-Reductase</a></div> <div id="annotation_132x300" style="position:absolute; left:132px; top:300px; font-size:12px; font-size:12; line-height:14px;"><a href="/wiki/3%CE%B1-Hydroxysteroid_dehydrogenase" title="3α-Hydroxysteroid dehydrogenase"><abbr title="3α-Hydroxysteroid dehydrogenase">3α-HSD</abbr></a></div> <div id="annotation_285x300" style="position:absolute; left:285px; top:300px; font-size:12px; font-size:12; line-height:14px;"><a href="/wiki/3%CE%B2-Hydroxysteroid_dehydrogenase" title="3β-Hydroxysteroid dehydrogenase"><abbr title="3β-Hydroxysteroid dehydrogenase">3β-HSD</abbr></a></div> <div id="annotation_409x300" style="position:absolute; left:409px; top:300px; font-size:12px; font-size:12; line-height:14px;"><a href="/wiki/3%CE%B1-Hydroxysteroid_dehydrogenase" title="3α-Hydroxysteroid dehydrogenase"><abbr title="3α-Hydroxysteroid dehydrogenase">3α-HSD</abbr></a></div> <div id="annotation_560x300" style="position:absolute; left:560px; top:300px; font-size:12px; font-size:12; line-height:14px;"><a href="/wiki/3%CE%B2-Hydroxysteroid_dehydrogenase" title="3β-Hydroxysteroid dehydrogenase"><abbr title="3β-Hydroxysteroid dehydrogenase">3β-HSD</abbr></a></div> <div id="annotation_662x395" style="position:absolute; left:662px; top:395px; font-size:12px; font-size:12; line-height:14px;"><a href="/wiki/20%CE%B1-Hydroxysteroid_dehydrogenase" class="mw-redirect" title="20α-Hydroxysteroid dehydrogenase"><abbr title="20α-Hydroxysteroid dehydrogenase">20α-HSD</abbr></a></div> <div id="annotation_662x411" style="position:absolute; left:662px; top:411px; font-size:12px; font-size:12; line-height:14px;"><a href="/wiki/20%CE%B2-Hydroxysteroid_dehydrogenase" class="mw-redirect" title="20β-Hydroxysteroid dehydrogenase"><abbr title="20β-Hydroxysteroid dehydrogenase">20β-HSD</abbr></a></div></div> </div> </div> <div class="thumbcaption" style="clear:left"><div style="float:left;margin-right:0.5em"><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" /></div>This diagram illustrates the <a href="/wiki/Metabolic_pathway" title="Metabolic pathway">metabolic pathways</a> involved in the <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> of progesterone in humans. In addition to the <a href="/wiki/Biotransformation" title="Biotransformation">transformations</a> shown in the diagram, <a href="/wiki/Conjugation_(biochemistry)" class="mw-redirect" title="Conjugation (biochemistry)">conjugation</a>, specifically <a href="/wiki/Glucuronidation" title="Glucuronidation">glucuronidation</a> and <a href="/wiki/Sulfation" title="Sulfation">sulfation</a>, occurs with <a href="/wiki/Metabolite" title="Metabolite">metabolites</a> of progesterone 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>.</div> </div> </div> </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Levels">Levels</h3>[<a href="/w/index.php?title=Progesterone&action=edit&section=24" title="Edit section: Levels">edit</a>]</div> <figure class="mw-default-size mw-halign-right skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Progesterone_levels_across_the_normal_menstrual_cycle_in_women.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Progesterone_levels_across_the_normal_menstrual_cycle_in_women.png/500px-Progesterone_levels_across_the_normal_menstrual_cycle_in_women.png" decoding="async" width="500" height="318" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Progesterone_levels_across_the_normal_menstrual_cycle_in_women.png/750px-Progesterone_levels_across_the_normal_menstrual_cycle_in_women.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Progesterone_levels_across_the_normal_menstrual_cycle_in_women.png/1000px-Progesterone_levels_across_the_normal_menstrual_cycle_in_women.png 2x" data-file-width="1970" data-file-height="1252" /></a><figcaption>Progesterone levels across the menstrual cycle in normally cycling and ovulatory women.<a href="#cite_note-pmid16776638-130">[130]</a> The horizontal lines are the mean integrated levels for each curve. The vertical line is mid-cycle.</figcaption></figure> Progesterone levels are relatively low during the preovulatory phase of the <a href="/wiki/Menstrual_cycle" title="Menstrual cycle">menstrual cycle</a>, rise after <a href="/wiki/Ovulation" title="Ovulation">ovulation</a>, and are elevated during the <a href="/wiki/Luteal_phase" title="Luteal phase">luteal phase</a>, as shown in the diagram above. Progesterone levels tend to be less than 2 ng/mL prior to ovulation and greater than 5 ng/mL after ovulation. If <a href="/wiki/Pregnancy" title="Pregnancy">pregnancy</a> occurs, <a href="/wiki/Human_chorionic_gonadotropin" title="Human chorionic gonadotropin">human chorionic gonadotropin</a> is released, maintaining the corpus luteum and allowing it to maintain levels of progesterone. Between 7 and 9 weeks, the placenta begins to produce progesterone in place of the corpus luteum in a process called the luteal-placental shift.<a href="#cite_note-pmid4688578-131">[131]</a> After the luteal-placental shift, progesterone levels start to rise further and may reach 100 to 200 ng/mL at term. Whether a decrease in progesterone levels is critical for the initiation of <a href="/wiki/Labor_(childbirth)" class="mw-redirect" title="Labor (childbirth)">labor</a> has been argued and may be species-specific. After delivery of the placenta and during lactation, progesterone levels are very low.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] Progesterone levels are low in children and postmenopausal people.<a href="#cite_note-132">[132]</a> Adult males have levels similar to those in women during the follicular phase of the menstrual cycle. <div style="clear:both;" class=""></div> <table class="wikitable sortable mw-collapsible" style="text-align:left; margin-left:auto; margin-right:auto; border:none;"> <caption class="nowrap">Endogenous <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a> production rates and plasma progesterone levels </caption> <tbody><tr> <th>Group</th> <th><abbr title="Progesterone">P4</abbr> production</th> <th><abbr title="Progesterone">P4</abbr> levels </th></tr> <tr> <td><a href="/wiki/Prepuberty" class="mw-redirect" title="Prepuberty">Prepubertal</a> children</td> <td><abbr title="No data">ND</abbr></td> <td>0.06–0.5 ng/mL </td></tr> <tr> <td><a href="/wiki/Puberty" title="Puberty">Pubertal</a> girls   <a href="/wiki/Tanner_scale#Definitions_of_stages" title="Tanner scale">Tanner stage I</a> (childhood)   <a href="/wiki/Tanner_scale#Definitions_of_stages" title="Tanner scale">Tanner stage II</a> (ages 8–12)   <a href="/wiki/Tanner_scale#Definitions_of_stages" title="Tanner scale">Tanner stage III</a> (ages 10–13)   <a href="/wiki/Tanner_scale#Definitions_of_stages" title="Tanner scale">Tanner stage IV</a> (ages 11–14)   <a href="/wiki/Tanner_scale#Definitions_of_stages" title="Tanner scale">Tanner stage V</a> (ages 12–15)     <a href="/wiki/Follicular_phase" title="Follicular phase">Follicular phase</a> (days 1–14)     <a href="/wiki/Luteal_phase" title="Luteal phase">Luteal phase</a> (days 15–28)</td> <td>  <abbr title="No data">ND</abbr> <abbr title="No data">ND</abbr> <abbr title="No data">ND</abbr> <abbr title="No data">ND</abbr>   <abbr title="No data">ND</abbr> <abbr title="No data">ND</abbr></td> <td>  0.22 (<0.10–0.32) ng/mL 0.30 (0.10–0.51) ng/mL 0.36 (0.10–0.75) ng/mL 1.75 (<0.10–25.0) ng/mL   0.35 (0.13–0.75) ng/mL 2.0–25.0 ng/mL </td></tr> <tr> <td><a href="/wiki/Premenopause" class="mw-redirect" title="Premenopause">Premenopausal</a> women   <a href="/wiki/Follicular_phase" title="Follicular phase">Follicular phase</a> (days 1–14)   <a href="/wiki/Luteal_phase" title="Luteal phase">Luteal phase</a> (days 15–28)   <a href="/wiki/Oral_contraceptive" class="mw-redirect" title="Oral contraceptive">Oral contraceptive</a> (<a href="/wiki/Anovulation" title="Anovulation">anovulatory</a>)</td> <td>  0.75–5.4 mg/day 15–50 mg/day <abbr title="No data">ND</abbr></td> <td>  0.02–1.2 ng/mL 4–30 ng/mL 0.1–0.3 ng/mL </td></tr> <tr> <td><a href="/wiki/Menopause" title="Menopause">Postmenopausal</a> women <a href="/wiki/Oophorectomy" title="Oophorectomy">Oophorectomized</a> women <a href="/wiki/Oophorectomy" title="Oophorectomy">Oophorectomized</a> and <a href="/wiki/Adrenalectomy" title="Adrenalectomy">adrenalectomized</a> women</td> <td><abbr title="No data">ND</abbr> 1.2 mg/day <0.3 mg/day</td> <td>0.03–0.3 ng/mL 0.39 ng/mL <abbr title="No data">ND</abbr> </td></tr> <tr> <td><a href="/wiki/Pregnancy" title="Pregnancy">Pregnant</a> women   <a href="/wiki/First_trimester" class="mw-redirect" title="First trimester">First trimester</a> (weeks 1–12)   <a href="/wiki/Second_trimester" class="mw-redirect" title="Second trimester">Second trimester</a> (weeks 13–26)   <a href="/wiki/Third_trimester" class="mw-redirect" title="Third trimester">Third trimester</a> (weeks 27–40)   <a href="/wiki/Postpartum" class="mw-redirect" title="Postpartum">Postpartum</a> (at 24 hours)</td> <td>  55 mg/day 92–100 mg/day 190–563 mg/day <abbr title="No data">ND</abbr></td> <td>  9–75 ng/mL 17–146 ng/mL 55–255 ng/mL 19 ng/mL </td></tr> <tr> <td>Men</td> <td>0.75–3 mg/day</td> <td>0.1–0.3 ng/mL </td></tr> <tr class="sortbottom"> <td colspan="5" style="width: 1px; background-color:#eaecf0; text-align: center;">Notes: Mean levels are given as a single value and ranges are given after in parentheses. Sources: <a href="#cite_note-pmid945344-129">[129]</a><a href="#cite_note-Chernecky_Berger_2012-133">[133]</a><a href="#cite_note-Becker_2001-134">[134]</a><a href="#cite_note-Josimovich2013b-135">[135]</a><a href="#cite_note-KeepUtian2012-136">[136]</a><a href="#cite_note-StraussBarbieri2009-137">[137]</a><a href="#cite_note-Bajaj_Berman2011-138">[138]</a><a href="#cite_note-Lauritzen1988-139">[139]</a><a href="#cite_note-LittleBilliar1983-140">[140]</a> </td></tr></tbody></table> <div class="mw-heading mw-heading4"><h4 id="Ranges">Ranges</h4>[<a href="/w/index.php?title=Progesterone&action=edit&section=25" title="Edit section: Ranges">edit</a>]</div> Blood test results should always be interpreted using the reference ranges provided by the laboratory that performed the results. Example reference ranges are listed below. <table class="wikitable" align="center"> <tbody><tr> <th rowspan="2">Person type</th> <th colspan="3"><a href="/wiki/Reference_range_for_blood_test" class="mw-redirect" title="Reference range for blood test">Reference range for blood test</a> </th></tr> <tr> <th>Lower limit</th> <th>Upper limit</th> <th>Unit </th></tr> <tr> <td>Female - menstrual cycle</td> <td colspan="3">(see diagram below) </td></tr> <tr> <td rowspan="2">Female - postmenopausal</td> <td><a href="/wiki/Less_than" class="mw-redirect" title="Less than"><</a>0.2<a href="#cite_note-nih2009-141">[141]</a></td> <td>1<a href="#cite_note-nih2009-141">[141]</a></td> <td><a href="/wiki/Nanogram" class="mw-redirect" title="Nanogram">ng</a>/<a href="/wiki/Millilitre" class="mw-redirect" title="Millilitre">mL</a> </td></tr> <tr> <td><0.6<a href="#cite_note-mass-converted-142">[142]</a></td> <td>3<a href="#cite_note-mass-converted-142">[142]</a></td> <td><a href="/wiki/Nanomole" class="mw-redirect" title="Nanomole">nmol</a>/<a href="/wiki/Litre" title="Litre">L</a> </td></tr> <tr> <td rowspan="2">Female on <a href="/wiki/Oral_contraceptive" class="mw-redirect" title="Oral contraceptive">oral contraceptives</a></td> <td>0.34<a href="#cite_note-nih2009-141">[141]</a></td> <td>0.92<a href="#cite_note-nih2009-141">[141]</a></td> <td>ng/mL </td></tr> <tr> <td>1.1<a href="#cite_note-mass-converted-142">[142]</a></td> <td>2.9<a href="#cite_note-mass-converted-142">[142]</a></td> <td>nmol/L </td></tr> <tr> <td rowspan="2">Males <a href="/wiki/Greater_than_or_equal_to" class="mw-redirect" title="Greater than or equal to">≥</a>16 years</td> <td>0.27<a href="#cite_note-nih2009-141">[141]</a></td> <td>0.9<a href="#cite_note-nih2009-141">[141]</a></td> <td>ng/mL </td></tr> <tr> <td>0.86<a href="#cite_note-mass-converted-142">[142]</a></td> <td>2.9<a href="#cite_note-mass-converted-142">[142]</a></td> <td>nmol/L </td></tr> <tr> <td rowspan="2">Female or male 1–9 years</td> <td>0.1<a href="#cite_note-nih2009-141">[141]</a></td> <td>4.1<a href="#cite_note-nih2009-141">[141]</a> or 4.5<a href="#cite_note-nih2009-141">[141]</a></td> <td>ng/mL </td></tr> <tr> <td>0.3<a href="#cite_note-mass-converted-142">[142]</a></td> <td>13<a href="#cite_note-mass-converted-142">[142]</a></td> <td>nmol/L </td></tr></tbody></table> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1214851843"><div class="hidden-begin mw-collapsible mw-collapsible-leftside-toggle mw-collapsed" style=""><div class="hidden-title skin-nightmode-reset-color" style="">Reference ranges for the blood content of progesterone during the menstrual cycle</div><div class="hidden-content mw-collapsible-content" style=""> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Progesterone_during_menstrual_cycle.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/48/Progesterone_during_menstrual_cycle.png/880px-Progesterone_during_menstrual_cycle.png" decoding="async" width="880" height="392" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/48/Progesterone_during_menstrual_cycle.png/1320px-Progesterone_during_menstrual_cycle.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/48/Progesterone_during_menstrual_cycle.png/1760px-Progesterone_during_menstrual_cycle.png 2x" data-file-width="3682" data-file-height="1640" /></a><figcaption>Progesterone levels during the <a href="/wiki/Menstrual_cycle" title="Menstrual cycle">menstrual cycle</a>.<a href="#cite_note-Häggström2014-143">[143]</a> • The ranges denoted By biological stage may be used in closely monitored menstrual cycles in regard to other markers of its biological progression, with the time scale being compressed or stretched to how much faster or slower, respectively, the cycle progresses compared to an average cycle. • The ranges denoted Inter-cycle variability are more appropriate to use in non-monitored cycles with only the beginning of menstruation known, but where the woman accurately knows her average cycle lengths and time of ovulation, and that they are somewhat averagely regular, with the time scale being compressed or stretched to how much a woman's average cycle length is shorter or longer, respectively, than the average of the population. • The ranges denoted Inter-woman variability are more appropriate to use when the average cycle lengths and time of ovulation are unknown, but only the beginning of menstruation is given.</figcaption></figure><div style="clear:both;" class=""></div> </div></div> <div class="mw-heading mw-heading3"><h3 id="Sources">Sources</h3>[<a href="/w/index.php?title=Progesterone&action=edit&section=26" title="Edit section: Sources">edit</a>]</div> <div class="mw-heading mw-heading4"><h4 id="Animal">Animal</h4>[<a href="/w/index.php?title=Progesterone&action=edit&section=27" title="Edit section: Animal">edit</a>]</div> Progesterone is produced in high amounts in the <a href="/wiki/Ovaries" class="mw-redirect" title="Ovaries">ovaries</a> (by the <a href="/wiki/Corpus_luteum" title="Corpus luteum">corpus luteum</a>) from the onset of <a href="/wiki/Puberty" title="Puberty">puberty</a> to <a href="/wiki/Menopause" title="Menopause">menopause</a>, and is also produced in smaller amounts by the <a href="/wiki/Adrenal_gland" title="Adrenal gland">adrenal glands</a> after the onset of <a href="/wiki/Adrenarche" title="Adrenarche">adrenarche</a> in both males and females. To a lesser extent, progesterone is produced in <a href="/wiki/Nervous_tissue" title="Nervous tissue">nervous tissue</a>, especially in the brain, and in <a href="/wiki/Adipose_tissue" title="Adipose tissue">adipose (fat) tissue</a>, as well. During human <a href="/wiki/Pregnancy" title="Pregnancy">pregnancy</a>, progesterone is produced in increasingly high amounts by the ovaries and <a href="/wiki/Placenta" title="Placenta">placenta</a>. At first, the source is the corpus luteum that has been "rescued" by the presence of <a href="/wiki/Human_chorionic_gonadotropin" title="Human chorionic gonadotropin">human chorionic gonadotropin</a> (hCG) from the conceptus. However, after the 8th week, production of progesterone shifts to the placenta. The placenta utilizes maternal cholesterol as the initial substrate, and most of the produced progesterone enters the maternal circulation, but some is picked up by the fetal circulation and used as substrate for fetal corticosteroids. At term the placenta produces about 250 mg progesterone per day. An additional animal source of progesterone is milk products. After consumption of milk products the level of bioavailable progesterone goes up.<a href="#cite_note-titleResult_Content_View-144">[144]</a> <div class="mw-heading mw-heading4"><h4 id="Plants">Plants</h4>[<a href="/w/index.php?title=Progesterone&action=edit&section=28" title="Edit section: Plants">edit</a>]</div> In at least one plant, <a href="/wiki/Juglans_regia" title="Juglans regia">Juglans regia</a>, progesterone has been detected.<a href="#cite_note-pmid20108949-145">[145]</a> In addition, progesterone-like <a href="/wiki/Steroid" title="Steroid">steroids</a> are found in <a href="/wiki/Dioscorea_mexicana" title="Dioscorea mexicana">Dioscorea mexicana</a>. Dioscorea mexicana is a plant that is part of the <a href="/wiki/Yam_(vegetable)" title="Yam (vegetable)">yam</a> family native to <a href="/wiki/Mexico" title="Mexico">Mexico</a>.<a href="#cite_note-pmid12255132-146">[146]</a> It contains a steroid called <a href="/wiki/Diosgenin" title="Diosgenin">diosgenin</a> that is taken from the plant and is converted into progesterone.<a href="#cite_note-pmid16946542-147">[147]</a> Diosgenin and progesterone are also found in other <a href="/wiki/Dioscorea" title="Dioscorea">Dioscorea</a> species, as well as in other plants that are not closely related, such as <a href="/wiki/Fenugreek" title="Fenugreek">fenugreek</a>. Another plant that contains substances readily convertible to progesterone is <a href="/wiki/Dioscorea_pseudojaponica" class="mw-redirect" title="Dioscorea pseudojaponica">Dioscorea pseudojaponica</a> native to <a href="/wiki/Taiwan" title="Taiwan">Taiwan</a>. Research has shown that the Taiwanese yam contains <a href="/wiki/Saponin" title="Saponin">saponins</a> — steroids that can be converted to diosgenin and thence to progesterone.<a href="#cite_note-pmid14558759-148">[148]</a> Many other Dioscorea species of the yam family contain steroidal substances from which progesterone can be produced. Among the more notable of these are <a href="/wiki/Dioscorea_villosa" title="Dioscorea villosa">Dioscorea villosa</a> and <a href="/wiki/Dioscorea_polygonoides" class="mw-redirect" title="Dioscorea polygonoides">Dioscorea polygonoides</a>. One study showed that the Dioscorea villosa contains 3.5% diosgenin.<a href="#cite_note-pmid15513824-149">[149]</a> <a href="/wiki/Dioscorea_polygonoides" class="mw-redirect" title="Dioscorea polygonoides">Dioscorea polygonoides</a> has been found to contain 2.64% diosgenin as shown by <a href="/wiki/Gas_chromatography-mass_spectrometry" class="mw-redirect" title="Gas chromatography-mass spectrometry">gas chromatography-mass spectrometry</a>.<a href="#cite_note-Nino-2007-150">[150]</a> Many of the Dioscorea species that originate from the yam family grow in countries that have tropical and subtropical climates.<a href="#cite_note-Myoda-2005-151">[151]</a> <div class="mw-heading mw-heading2"><h2 id="Medical_use">Medical use</h2>[<a href="/w/index.php?title=Progesterone&action=edit&section=29" title="Edit section: Medical use">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main articles: <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">Progesterone (medication)</a>, <a href="/wiki/Pharmacodynamics_of_progesterone" title="Pharmacodynamics of progesterone">Pharmacodynamics of progesterone</a>, and <a href="/wiki/Pharmacokinetics_of_progesterone" title="Pharmacokinetics of progesterone">Pharmacokinetics of progesterone</a></div> Progesterone is used as a <a href="/wiki/Medication" title="Medication">medication</a>. It is used in combination with <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogens</a> mainly in <a href="/wiki/Hormone_replacement_therapy" title="Hormone replacement therapy">hormone therapy</a> for <a href="/wiki/Menopause" title="Menopause">menopausal</a> <a href="/wiki/Symptom" class="mw-redirect" title="Symptom">symptoms</a> and <a href="/wiki/Hypogonadism" title="Hypogonadism">low sex hormone levels</a>.<a href="#cite_note-pmid16112947-116">[116]</a><a href="#cite_note-pmid28159148-152">[152]</a> It may also be used alone to treat menopausal symptoms. Studies have shown that transdermal progesterone (skin patch) and oral micronized progesterone are effective treatments for certain symptoms of menopause such as hot flashes and night sweats, which are otherwise referred to as vasomotor symptoms or VMS.<a href="#cite_note-pmid33109992-153">[153]</a> It is also used to support <a href="/wiki/Pregnancy" title="Pregnancy">pregnancy</a> and <a href="/wiki/Fertility" title="Fertility">fertility</a> and to treat <a href="/wiki/Gynecological_disorder" class="mw-redirect" title="Gynecological disorder">gynecological disorders</a>.<a href="#cite_note-pmid25113944-154">[154]</a><a href="#cite_note-pmid26443945-155">[155]</a><a href="#cite_note-pmid26345161-156">[156]</a><a href="#cite_note-pmid28989916-157">[157]</a> Progesterone has been shown to prevent miscarriage in those with 1) vaginal bleeding early in their current pregnancy and 2) a previous history of miscarriage.<a href="#cite_note-pmid32609084-158">[158]</a> Progesterone can be taken <a href="/wiki/Oral_administration" title="Oral administration">by mouth</a>, <a href="/wiki/Intravaginal_administration" title="Intravaginal administration">through the vagina</a>, and by <a href="/wiki/Injection_(medicine)" title="Injection (medicine)">injection</a> into <a href="/wiki/Muscle" title="Muscle">muscle</a> or <a href="/wiki/Fat" title="Fat">fat</a>, among other <a href="/wiki/Route_of_administration" title="Route of administration">routes</a>.<a href="#cite_note-pmid16112947-116">[116]</a> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2>[<a href="/w/index.php?title=Progesterone&action=edit&section=30" title="Edit section: Chemistry">edit</a>]</div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Sample_of_Progesterone.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9a/Sample_of_Progesterone.jpg/170px-Sample_of_Progesterone.jpg" decoding="async" width="170" height="248" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9a/Sample_of_Progesterone.jpg/255px-Sample_of_Progesterone.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9a/Sample_of_Progesterone.jpg/340px-Sample_of_Progesterone.jpg 2x" data-file-width="2762" data-file-height="4025" /></a><figcaption>A sample of progesterone</figcaption></figure> <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_neurosteroids" title="List of neurosteroids">List of neurosteroids</a></div> Progesterone is a <a href="/wiki/Natural_product" title="Natural product">naturally occurring</a> <a href="/wiki/Pregnane" title="Pregnane">pregnane</a> <a href="/wiki/Steroid" title="Steroid">steroid</a> and is also known as pregn-4-ene-3,20-dione.<a href="#cite_note-Elks2014-159">[159]</a><a href="#cite_note-IndexNominum2000-160">[160]</a> It has a <a href="/wiki/Double_bond" title="Double bond">double bond</a> (<a href="/wiki/-ene" title="-ene">4-ene</a>) between the C4 and C5 positions and two <a href="/wiki/Ketone" title="Ketone">ketone</a> <a href="/wiki/Functional_group" title="Functional group">groups</a> (3,20-<a href="/wiki/Diketone" class="mw-redirect" title="Diketone">dione</a>), one at the C3 position and the other at the C20 position.<a href="#cite_note-Elks2014-159">[159]</a><a href="#cite_note-IndexNominum2000-160">[160]</a> <div class="mw-heading mw-heading3"><h3 id="Synthesis">Synthesis</h3>[<a href="/w/index.php?title=Progesterone&action=edit&section=31" title="Edit section: Synthesis">edit</a>]</div> Progesterone is commercially produced by semisynthesis. Two main routes are used: one from yam <a href="/wiki/Diosgenin" title="Diosgenin">diosgenin</a> first pioneered by Marker in 1940, and one based on soy <a href="/wiki/Phytosterol" title="Phytosterol">phytosterols</a> scaled up in the 1970s. Additional (not necessarily economical) semisyntheses of progesterone have also been reported starting from a variety of steroids. For the example, <a href="/wiki/Cortisone" title="Cortisone">cortisone</a> can be simultaneously deoxygenated at the C-17 and C-21 position by treatment with iodotrimethylsilane in <a href="/wiki/Chloroform" title="Chloroform">chloroform</a> to produce 11-keto-progesterone (ketogestin), which in turn can be reduced at position-11 to yield progesterone.<a href="#cite_note-pmid3815593-161">[161]</a> <div class="mw-heading mw-heading4"><h4 id="Marker_semisynthesis">Marker semisynthesis</h4>[<a href="/w/index.php?title=Progesterone&action=edit&section=32" title="Edit section: Marker semisynthesis">edit</a>]</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/Marker_degradation" title="Marker degradation">Marker degradation</a></div> An economical <a href="/wiki/Semisynthesis" title="Semisynthesis">semisynthesis</a> of progesterone from the plant steroid <a href="/wiki/Diosgenin" title="Diosgenin">diosgenin</a> isolated from yams was developed by <a href="/wiki/Russell_Earl_Marker" title="Russell Earl Marker">Russell Marker</a> in 1940 for the <a href="/wiki/Parke-Davis" title="Parke-Davis">Parke-Davis</a> pharmaceutical company.<a href="#cite_note-Marker1940-162">[162]</a> This synthesis is known as the <a href="/wiki/Marker_degradation" title="Marker degradation">Marker degradation</a>. <figure class="mw-default-size mw-halign-center skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Marker_snythesis.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/22/Marker_snythesis.png/800px-Marker_snythesis.png" decoding="async" width="800" height="366" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/22/Marker_snythesis.png/1200px-Marker_snythesis.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/22/Marker_snythesis.png/1600px-Marker_snythesis.png 2x" data-file-width="2753" data-file-height="1261" /></a><figcaption>The Marker <a href="/wiki/Semisynthesis" title="Semisynthesis">semisynthesis</a> of progesterone from <a href="/wiki/Diosgenin" title="Diosgenin">diosgenin</a>.<a href="#cite_note-Marker1940-162">[162]</a></figcaption></figure> The <a href="/wiki/16-DPA" class="mw-redirect" title="16-DPA">16-DPA</a> intermediate is important to the synthesis of many other medically important steroids. A very similar approach can produce 16-DPA from <a href="/wiki/Solanine" title="Solanine">solanine</a>.<a href="#cite_note-Goswami-2003-163">[163]</a> <div class="mw-heading mw-heading4"><h4 id="Soy_semisynthesis">Soy semisynthesis</h4>[<a href="/w/index.php?title=Progesterone&action=edit&section=33" title="Edit section: Soy semisynthesis">edit</a>]</div> Progesterone can also be made from the <a href="/wiki/Stigmasterol" title="Stigmasterol">stigmasterol</a> found in <a href="/wiki/Soybean_oil" title="Soybean oil">soybean oil</a> also. c.f. <a href="/wiki/Percy_Julian" class="mw-redirect" title="Percy Julian">Percy Julian</a>. <figure class="mw-default-size mw-halign-center skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Stigmasterol_to_progesterone_synthesis.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Stigmasterol_to_progesterone_synthesis.png/800px-Stigmasterol_to_progesterone_synthesis.png" decoding="async" width="800" height="309" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Stigmasterol_to_progesterone_synthesis.png/1200px-Stigmasterol_to_progesterone_synthesis.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Stigmasterol_to_progesterone_synthesis.png/1600px-Stigmasterol_to_progesterone_synthesis.png 2x" data-file-width="4011" data-file-height="1551" /></a><figcaption><a href="/wiki/Stigmasterol" title="Stigmasterol">Stigmasterol</a> to progesterone synthesis.<a href="#cite_note-Heyl-164">[164]</a><a href="#cite_note-Slomp-1958-165">[165]</a><a href="#cite_note-pmid915584-166">[166]</a><a href="#cite_note-PBS.org-2007-167">[167]</a><a href="#cite_note-lipidlibrary.aocs.org-168">[168]</a></figcaption></figure> <div class="mw-heading mw-heading4"><h4 id="Total_synthesis">Total synthesis</h4>[<a href="/w/index.php?title=Progesterone&action=edit&section=34" title="Edit section: Total synthesis">edit</a>]</div> <figure class="mw-default-size mw-halign-right skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Progesterone_Synthesis.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Progesterone_Synthesis.png/440px-Progesterone_Synthesis.png" decoding="async" width="440" height="804" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Progesterone_Synthesis.png/660px-Progesterone_Synthesis.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Progesterone_Synthesis.png/880px-Progesterone_Synthesis.png 2x" data-file-width="1353" data-file-height="2472" /></a><figcaption>The Johnson total synthesis of progesterone.<a href="#cite_note-pmid5131151-169">[169]</a></figcaption></figure> A <a href="/wiki/Total_synthesis" title="Total synthesis">total synthesis</a> of progesterone was reported in 1971 by <a href="/wiki/William_Summer_Johnson" title="William Summer Johnson">W.S. Johnson</a>.<a href="#cite_note-pmid5131151-169">[169]</a> The synthesis begins with reacting the <a href="/wiki/Phosphonium_salt" class="mw-redirect" title="Phosphonium salt">phosphonium salt</a> 7 with <a href="/wiki/Organolithium_reagent" title="Organolithium reagent">phenyl lithium</a> to produce the <a href="/wiki/Phosphonium_ylide" class="mw-redirect" title="Phosphonium ylide">phosphonium ylide</a> 8. The ylide 8 is reacted with an <a href="/wiki/Aldehyde" title="Aldehyde">aldehyde</a> to produce the <a href="/wiki/Alkene" title="Alkene">alkene</a> 9. The <a href="/wiki/Ketal" class="mw-redirect" title="Ketal">ketal</a> <a href="/wiki/Protecting_group" title="Protecting group">protecting groups</a> of 9 are hydrolyzed to produce the diketone 10, which in turn is cyclized to form the cyclopentenone 11. The ketone of 11 is reacted with methyl lithium to yield the tertiary alcohol 12, which in turn is treated with acid to produce the tertiary cation 13. The key step of the synthesis is the π-cation cyclization of 13 in which the B-, C-, and D-rings of the steroid are simultaneously formed to produce 14. This step resembles the cationic cyclization reaction used in the biosynthesis of steroids and hence is referred to as biomimetic. In the next step the <a href="/wiki/Enol" title="Enol">enol</a> <a href="/wiki/Orthoester" class="mw-redirect" title="Orthoester">orthoester</a> is hydrolyzed to produce the ketone 15. The cyclopentene A-ring is then opened by oxidizing with ozone to produce 16. Finally, the diketone 17 undergoes an intramolecular <a href="/wiki/Aldol_condensation" title="Aldol condensation">aldol condensation</a> by treating with aqueous potassium hydroxide to produce progesterone.<a href="#cite_note-pmid5131151-169">[169]</a> <div class="mw-heading mw-heading2"><h2 id="History">History</h2>[<a href="/w/index.php?title=Progesterone&action=edit&section=35" title="Edit section: History">edit</a>]</div> <a href="/wiki/George_W._Corner" title="George W. Corner">George W. Corner</a> and <a href="/wiki/Willard_Myron_Allen" title="Willard Myron Allen">Willard M. Allen</a> discovered the hormonal action of progesterone in 1929.<a href="#cite_note-Josimovich2013-17">[17]</a><a href="#cite_note-Corner-1929-170">[170]</a><a href="#cite_note-CoutinhoSegal1999-171">[171]</a><a href="#cite_note-Walker2008-172">[172]</a> By 1931–1932, nearly pure crystalline material of high progestational activity had been isolated from the <a href="/wiki/Corpus_luteum" title="Corpus luteum">corpus luteum</a> of animals, and by 1934, pure crystalline progesterone had been refined and obtained and the <a href="/wiki/Chemical_structure" title="Chemical structure">chemical structure</a> of progesterone was determined.<a href="#cite_note-Josimovich2013-17">[17]</a><a href="#cite_note-CoutinhoSegal1999-171">[171]</a> This was achieved by <a href="/wiki/Adolf_Butenandt" title="Adolf Butenandt">Adolf Butenandt</a> at the <a href="/wiki/Faculty_of_Chemistry,_Gda%C5%84sk_University_of_Technology" class="mw-redirect" title="Faculty of Chemistry, Gdańsk University of Technology">Chemisches Institut</a> of <a href="/wiki/Gda%C5%84sk_University_of_Technology" title="Gdańsk University of Technology">Technical University</a> in <a href="/wiki/Danzig" class="mw-redirect" title="Danzig">Danzig</a>, who extracted this new compound from several thousand liters of <a href="/wiki/Urine" title="Urine">urine</a>.<a href="#cite_note-Piosik-2003-173">[173]</a> <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">Chemical synthesis</a> of progesterone from <a href="/wiki/Stigmasterol" title="Stigmasterol">stigmasterol</a> and <a href="/wiki/Pregnanediol" title="Pregnanediol">pregnanediol</a> was accomplished later that year.<a href="#cite_note-CoutinhoSegal1999-171">[171]</a><a href="#cite_note-Ginsburg2012-174">[174]</a> Up to this point, progesterone, known generically as corpus luteum hormone, had been being referred to by several groups by different names, including corporin, lutein, luteosterone, and progestin.<a href="#cite_note-Josimovich2013-17">[17]</a><a href="#cite_note-Rolleston1936-175">[175]</a> In 1935, at the time of the Second International Conference on the Standardization of Sex Hormones in <a href="/wiki/London,_England" class="mw-redirect" title="London, England">London, England</a>, a compromise was made between the groups and the name progesterone (progestational steroidal ketone) was created.<a href="#cite_note-Josimovich2013-17">[17]</a><a href="#cite_note-pmid4922128-176">[176]</a> <div class="mw-heading mw-heading3"><h3 id="Veterinary_use">Veterinary use</h3>[<a href="/w/index.php?title=Progesterone&action=edit&section=36" title="Edit section: Veterinary use">edit</a>]</div> The use of progesterone tests in dog breeding to pinpoint ovulation is becoming more widely used. There are several tests available but the most reliable test is a blood test with blood drawn by a veterinarian and sent to a lab for processing. Results can usually be obtained with 24 to 72 hours. The rationale for using progesterone tests is that increased numbers begin in close proximity to preovulatory surge in gonadotrophins and continue through ovulation and estrus. When progesterone levels reach certain levels they can signal the stage of estrus the female is. Prediction of birth date of the pending litter can be very accurate if ovulation date is known. Puppies deliver with a day or two of 9 weeks gestation in most cases. It is not possible to determine pregnancy using progesterone tests once a breeding has taken place, however. This is due to the fact that, in dogs, progesterone levels remain elevated throughout the estrus period.<a href="#cite_note-Refsal-2009-177">[177]</a> <div class="mw-heading mw-heading3"><h3 id="Pricing">Pricing</h3>[<a href="/w/index.php?title=Progesterone&action=edit&section=37" title="Edit section: Pricing">edit</a>]</div> Pricing for progesterone can vary depending location, insurance coverage, discount coupons, quantity, shortages, manufacturers, brand or generic versions, different pharmacies, and so on. As of currently, 30 capsules of 100 mg of the generic version, Prometrium, from CVS Pharmacy is around $40 without any discounts or insurance applied. The brand version, Progesterone, is around $450 for 30 capsules without any discounts or insurance applied.<a href="#cite_note-www.goodrx.com-prices-178">[178]</a> In comparison, Walgreens offers 30 capsules of 100 mg in the generic version for $51 without insurance or coupons applied. The brand name costs around $431 for 30 capsules of 100 mg.<a href="#cite_note-www.goodrx.com-prices-2-179">[179]</a> <div style="clear:both;" class=""></div> <div class="mw-heading mw-heading2"><h2 id="References">References</h2>[<a href="/w/index.php?title=Progesterone&action=edit&section=38" title="Edit section: References">edit</a>]</div> <ul><li><a href="//creativecommons.org/licenses/by-sa/3.0/" title="creativecommons:by-sa/3.0/"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d9/Creative_Commons_by-sa_small.svg/80px-Creative_Commons_by-sa_small.svg.png" decoding="async" width="80" height="15" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d9/Creative_Commons_by-sa_small.svg/120px-Creative_Commons_by-sa_small.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d9/Creative_Commons_by-sa_small.svg/160px-Creative_Commons_by-sa_small.svg.png 2x" data-file-width="80" data-file-height="15" /></a> This article incorporates <a class="external text" href="https://en.wikiversity.org/wiki?curid=269289">text</a> available under the <a href="//creativecommons.org/licenses/by-sa/3.0/" class="extiw" title="creativecommons:by-sa/3.0/">CC BY-SA 3.0</a> license.</li></ul> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-James2015-1">^ <a href="#cite_ref-James2015_1-0">a</a> <a href="#cite_ref-James2015_1-1">b</a> <style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFJamesonDe_Groot2015" class="citation book cs1">Jameson JL, De Groot LJ (25 February 2015). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=xmLeBgAAQBAJ&pg=PA2179">Endocrinology: Adult and Pediatric E-Book</a>. Elsevier Health Sciences. p. 2179. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-323-32195-2" title="Special:BookSources/978-0-323-32195-2"><bdi>978-0-323-32195-2</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230114025031/https://books.google.com/books?id=xmLeBgAAQBAJ&pg=PA2179">Archived</a> from the original on 14 January 2023. Retrieved 29 October 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Endocrinology%3A+Adult+and+Pediatric+E-Book&rft.pages=2179&rft.pub=Elsevier+Health+Sciences&rft.date=2015-02-25&rft.isbn=978-0-323-32195-2&rft.aulast=Jameson&rft.aufirst=JL&rft.au=De+Groot%2C+LJ&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DxmLeBgAAQBAJ%26pg%3DPA2179&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-Adler-2012-2"><a href="#cite_ref-Adler-2012_2-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAdlerPfaffGoy2012" class="citation book cs1">Adler N, Pfaff D, Goy RW (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=MoDrBwAAQBAJ&q=pregn-4-ene-3,20-dione;+abbreviated+as+P4&pg=PA189">Handbook of Behavioral Neurobiology Volume 7 Reproduction</a> (1st ed.). New York: Plenum Press. p. 189. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4684-4834-4" title="Special:BookSources/978-1-4684-4834-4"><bdi>978-1-4684-4834-4</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230114024946/https://books.google.com/books?id=MoDrBwAAQBAJ&q=pregn-4-ene-3,20-dione;+abbreviated+as+P4&pg=PA189">Archived</a> from the original on 14 January 2023. Retrieved 4 July 2015.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Handbook+of+Behavioral+Neurobiology+Volume+7+Reproduction&rft.place=New+York&rft.pages=189&rft.edition=1st&rft.pub=Plenum+Press&rft.date=2012-12-06&rft.isbn=978-1-4684-4834-4&rft.aulast=Adler&rft.aufirst=N&rft.au=Pfaff%2C+D&rft.au=Goy%2C+RW&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DMoDrBwAAQBAJ%26q%3Dpregn-4-ene-3%2C20-dione%3B%2Babbreviated%2Bas%2BP4%26pg%3DPA189&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-ChEBI-17026-3"><a href="#cite_ref-ChEBI-17026_3-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.ebi.ac.uk/chebi/searchId.do;jsessionid=309FCC7D184C0AD58410071F3F163155?chebiId=17026&structureView=applet&viewTermLineage=">"progesterone (CHEBI:17026)"</a>. ChEBI. European Molecular Biology Laboratory-EBI. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20160320211423/http://www.ebi.ac.uk/chebi/searchId.do;jsessionid=309FCC7D184C0AD58410071F3F163155?chebiId=17026&structureView=applet&viewTermLineage=">Archived</a> from the original on 20 March 2016. Retrieved 4 July 2015.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=ChEBI&rft.atitle=progesterone+%28CHEBI%3A17026%29&rft_id=http%3A%2F%2Fwww.ebi.ac.uk%2Fchebi%2FsearchId.do%3Bjsessionid%3D309FCC7D184C0AD58410071F3F163155%3FchebiId%3D17026%26structureView%3Dapplet%26viewTermLineage%3D&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-chemsrc-4"><a href="#cite_ref-chemsrc_4-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.chemsrc.com/en/cas/57-83-0_1068061.html">"Progesterone_msds"</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210212022152/https://www.chemsrc.com/en/cas/57-83-0_1068061.html">Archived</a> from the original on 12 February 2021. Retrieved 19 April 2018.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Progesterone_msds&rft_id=https%3A%2F%2Fwww.chemsrc.com%2Fen%2Fcas%2F57-83-0_1068061.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-pmid12215716-5">^ <a href="#cite_ref-pmid12215716_5-0">a</a> <a href="#cite_ref-pmid12215716_5-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFStanczyk2002" class="citation journal cs1">Stanczyk FZ (September 2002). "Pharmacokinetics and potency of progestins used for hormone replacement therapy and contraception". Reviews in Endocrine & Metabolic Disorders. 3 (3): 211–224. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1023%2FA%3A1020072325818">10.1023/A:1020072325818</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/12215716">12215716</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:27018468">27018468</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Reviews+in+Endocrine+%26+Metabolic+Disorders&rft.atitle=Pharmacokinetics+and+potency+of+progestins+used+for+hormone+replacement+therapy+and+contraception&rft.volume=3&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E211-%3C%2Fspan%3E224&rft.date=2002-09&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A27018468%23id-name%3DS2CID&rft_id=info%3Apmid%2F12215716&rft_id=info%3Adoi%2F10.1023%2FA%3A1020072325818&rft.aulast=Stanczyk&rft.aufirst=FZ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-pmid8513955-6">^ <a href="#cite_ref-pmid8513955_6-0">a</a> <a href="#cite_ref-pmid8513955_6-1">b</a> <a href="#cite_ref-pmid8513955_6-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSimonRobinsonAndrewsHildebrand1993" class="citation journal cs1">Simon JA, Robinson DE, Andrews MC, Hildebrand JR, Rocci ML, Blake RE, Hodgen GD (July 1993). <a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0015-0282%2816%2956031-2">"The absorption of oral micronized progesterone: the effect of food, dose proportionality, and comparison with intramuscular progesterone"</a>. Fertility and Sterility. 60 (1): 26–33. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0015-0282%2816%2956031-2">10.1016/S0015-0282(16)56031-2</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/8513955">8513955</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=The+absorption+of+oral+micronized+progesterone%3A+the+effect+of+food%2C+dose+proportionality%2C+and+comparison+with+intramuscular+progesterone&rft.volume=60&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E26-%3C%2Fspan%3E33&rft.date=1993-07&rft_id=info%3Adoi%2F10.1016%2FS0015-0282%2816%2956031-2&rft_id=info%3Apmid%2F8513955&rft.aulast=Simon&rft.aufirst=JA&rft.au=Robinson%2C+DE&rft.au=Andrews%2C+MC&rft.au=Hildebrand%2C+JR&rft.au=Rocci%2C+ML&rft.au=Blake%2C+RE&rft.au=Hodgen%2C+GD&rft_id=https%3A%2F%2Fdoi.org%2F10.1016%252FS0015-0282%252816%252956031-2&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-FritzSperoff2012-7"><a href="#cite_ref-FritzSperoff2012_7-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFritzSperoff2012" class="citation book cs1">Fritz MA, Speroff L (28 March 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=KZLubBxJEwEC&pg=PA44">Clinical Gynecologic Endocrinology and Infertility</a>. Lippincott Williams & Wilkins. pp. 44–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4511-4847-3" title="Special:BookSources/978-1-4511-4847-3"><bdi>978-1-4511-4847-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Clinical+Gynecologic+Endocrinology+and+Infertility&rft.pages=44-&rft.pub=Lippincott+Williams+%26+Wilkins&rft.date=2012-03-28&rft.isbn=978-1-4511-4847-3&rft.aulast=Fritz&rft.aufirst=MA&rft.au=Speroff%2C+L&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DKZLubBxJEwEC%26pg%3DPA44&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-MarshallD.2008-8"><a href="#cite_ref-MarshallD.2008_8-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMarshallBangert2008" class="citation book cs1">Marshall WJ, Bangert SK (2008). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=Gjc704GR5YEC&pg=PA192">Clinical Chemistry</a>. Elsevier Health Sciences. pp. 192–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7234-3455-9" title="Special:BookSources/978-0-7234-3455-9"><bdi>978-0-7234-3455-9</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230114024953/https://books.google.com/books?id=Gjc704GR5YEC&pg=PA192">Archived</a> from the original on 14 January 2023. Retrieved 5 October 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Clinical+Chemistry&rft.pages=192-&rft.pub=Elsevier+Health+Sciences&rft.date=2008&rft.isbn=978-0-7234-3455-9&rft.aulast=Marshall&rft.aufirst=WJ&rft.au=Bangert%2C+SK&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DGjc704GR5YEC%26pg%3DPA192&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-pmid9328296-9"><a href="#cite_ref-pmid9328296_9-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFYamazakiShimada1997" class="citation journal cs1">Yamazaki H, Shimada T (October 1997). "Progesterone and testosterone hydroxylation by cytochromes P450 2C19, 2C9, and 3A4 in human liver microsomes". Archives of Biochemistry and Biophysics. 346 (1): 161–169. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1006%2Fabbi.1997.0302">10.1006/abbi.1997.0302</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/9328296">9328296</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Archives+of+Biochemistry+and+Biophysics&rft.atitle=Progesterone+and+testosterone+hydroxylation+by+cytochromes+P450+2C19%2C+2C9%2C+and+3A4+in+human+liver+microsomes&rft.volume=346&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E161-%3C%2Fspan%3E169&rft.date=1997-10&rft_id=info%3Adoi%2F10.1006%2Fabbi.1997.0302&rft_id=info%3Apmid%2F9328296&rft.aulast=Yamazaki&rft.aufirst=H&rft.au=Shimada%2C+T&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-McKayWalters2013-10"><a href="#cite_ref-McKayWalters2013_10-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMcKayWalters2013" class="citation book cs1">McKay GA, Walters MR (6 February 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=OGOqcfN_Cc8C&pg=PT33">Lecture Notes: Clinical Pharmacology and Therapeutics</a>. John Wiley & Sons. p. 33. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-118-34489-7" title="Special:BookSources/978-1-118-34489-7"><bdi>978-1-118-34489-7</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230114024939/https://books.google.com/books?id=OGOqcfN_Cc8C&pg=PT33">Archived</a> from the original on 14 January 2023. Retrieved 27 June 2015.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Lecture+Notes%3A+Clinical+Pharmacology+and+Therapeutics&rft.pages=33&rft.pub=John+Wiley+%26+Sons&rft.date=2013-02-06&rft.isbn=978-1-118-34489-7&rft.aulast=McKay&rft.aufirst=GA&rft.au=Walters%2C+MR&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DOGOqcfN_Cc8C%26pg%3DPT33&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-Zutshi-2005-11"><a href="#cite_ref-Zutshi-2005_11-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFZutshiRathoreSharma2005" class="citation book cs1">Zutshi V, Rathore AM, Sharma K (1 January 2005). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=IBxBbaDjXw0C&pg=PA74">Hormones in Obstetrics and Gynaecology</a>. Jaypee Brothers Publishers. p. 74. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-81-8061-427-9" title="Special:BookSources/978-81-8061-427-9"><bdi>978-81-8061-427-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Hormones+in+Obstetrics+and+Gynaecology&rft.pages=74&rft.pub=Jaypee+Brothers+Publishers&rft.date=2005-01-01&rft.isbn=978-81-8061-427-9&rft.aulast=Zutshi&rft.aufirst=V&rft.au=Rathore%2C+AM&rft.au=Sharma%2C+K&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DIBxBbaDjXw0C%26pg%3DPA74&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988">[<a href="/wiki/Wikipedia:Link_rot" title="Wikipedia:Link rot">permanent dead link</a>‍] </li> <li id="cite_note-pmid26342177-12">^ <a href="#cite_ref-pmid26342177_12-0">a</a> <a href="#cite_ref-pmid26342177_12-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCometti2015" class="citation journal cs1">Cometti B (November 2015). <a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Faogs.12765">"Pharmaceutical and clinical development of a novel progesterone formulation"</a>. Acta Obstetricia et Gynecologica Scandinavica. 94 (Suppl 161): 28–37. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Faogs.12765">10.1111/aogs.12765</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/26342177">26342177</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:31974637">31974637</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Obstetricia+et+Gynecologica+Scandinavica&rft.atitle=Pharmaceutical+and+clinical+development+of+a+novel+progesterone+formulation&rft.volume=94&rft.issue=Suppl+161&rft.pages=%3Cspan+class%3D%22nowrap%22%3E28-%3C%2Fspan%3E37&rft.date=2015-11&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A31974637%23id-name%3DS2CID&rft_id=info%3Apmid%2F26342177&rft_id=info%3Adoi%2F10.1111%2Faogs.12765&rft.aulast=Cometti&rft.aufirst=B&rft_id=https%3A%2F%2Fdoi.org%2F10.1111%252Faogs.12765&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-KingBrucker2010-13">^ <a href="#cite_ref-KingBrucker2010_13-0">a</a> <a href="#cite_ref-KingBrucker2010_13-1">b</a> <a href="#cite_ref-KingBrucker2010_13-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKingBrucker2010" class="citation book cs1">King TL, Brucker MC (25 October 2010). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=E9qVyrNPsBkC&pg=PA373">Pharmacology for Women's Health</a>. Jones & Bartlett Publishers. pp. 372–373. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4496-5800-7" title="Special:BookSources/978-1-4496-5800-7"><bdi>978-1-4496-5800-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Pharmacology+for+Women%27s+Health&rft.pages=%3Cspan+class%3D%22nowrap%22%3E372-%3C%2Fspan%3E373&rft.pub=Jones+%26+Bartlett+Publishers&rft.date=2010-10-25&rft.isbn=978-1-4496-5800-7&rft.aulast=King&rft.aufirst=TL&rft.au=Brucker%2C+MC&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DE9qVyrNPsBkC%26pg%3DPA373&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-pmid11108866-14">^ <a href="#cite_ref-pmid11108866_14-0">a</a> <a href="#cite_ref-pmid11108866_14-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBaulieuSchumacher2000" class="citation journal cs1">Baulieu E, Schumacher M (2000). "Progesterone as a neuroactive neurosteroid, with special reference to the effect of progesterone on myelination". Steroids. 65 (10–11): 605–612. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fs0039-128x%2800%2900173-2">10.1016/s0039-128x(00)00173-2</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/11108866">11108866</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:14952168">14952168</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Steroids&rft.atitle=Progesterone+as+a+neuroactive+neurosteroid%2C+with+special+reference+to+the+effect+of+progesterone+on+myelination&rft.volume=65&rft.issue=%3Cspan+class%3D%22nowrap%22%3E10%E2%80%93%3C%2Fspan%3E11&rft.pages=%3Cspan+class%3D%22nowrap%22%3E605-%3C%2Fspan%3E612&rft.date=2000&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A14952168%23id-name%3DS2CID&rft_id=info%3Apmid%2F11108866&rft_id=info%3Adoi%2F10.1016%2Fs0039-128x%2800%2900173-2&rft.aulast=Baulieu&rft.aufirst=E&rft.au=Schumacher%2C+M&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-pmid30608551-15"><a href="#cite_ref-pmid30608551_15-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPrior2019" class="citation journal cs1">Prior JC (April 2019). <a rel="nofollow" class="external text" href="https://doi.org/10.1210%2Fjc.2018-01777">"Progesterone Is Important for Transgender Women's Therapy-Applying Evidence for the Benefits of Progesterone in Ciswomen"</a>. The Journal of Clinical Endocrinology and Metabolism. 104 (4): 1181–1186. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1210%2Fjc.2018-01777">10.1210/jc.2018-01777</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/30608551">30608551</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:58620122">58620122</a>. <q>Evidence has accrued that normal progesterone (and ovulation), as well as physiological estradiol levels, is necessary during ciswomen's premenopausal menstrual cycles for current fertility and long-term health; transgender women may require progesterone therapy and similar potential physiological benefits</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Clinical+Endocrinology+and+Metabolism&rft.atitle=Progesterone+Is+Important+for+Transgender+Women%27s+Therapy-Applying+Evidence+for+the+Benefits+of+Progesterone+in+Ciswomen&rft.volume=104&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1181-%3C%2Fspan%3E1186&rft.date=2019-04&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A58620122%23id-name%3DS2CID&rft_id=info%3Apmid%2F30608551&rft_id=info%3Adoi%2F10.1210%2Fjc.2018-01777&rft.aulast=Prior&rft.aufirst=JC&rft_id=https%3A%2F%2Fdoi.org%2F10.1210%252Fjc.2018-01777&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-Fis2006-16"><a href="#cite_ref-Fis2006_16-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFischerGanellin2006" class="citation book cs1">Fischer J, Ganellin CR (2006). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA47X">Analogue-based Drug Discovery</a>. John Wiley & Sons. p. 47X. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9783527607495" title="Special:BookSources/9783527607495"><bdi>9783527607495</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Analogue-based+Drug+Discovery&rft.pages=47X&rft.pub=John+Wiley+%26+Sons&rft.date=2006&rft.isbn=9783527607495&rft.aulast=Fischer&rft.aufirst=J&rft.au=Ganellin%2C+CR&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DFjKfqkaKkAAC%26pg%3DPA47X&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-Josimovich2013-17">^ <a href="#cite_ref-Josimovich2013_17-0">a</a> <a href="#cite_ref-Josimovich2013_17-1">b</a> <a href="#cite_ref-Josimovich2013_17-2">c</a> <a href="#cite_ref-Josimovich2013_17-3">d</a> <a href="#cite_ref-Josimovich2013_17-4">e</a> <a href="#cite_ref-Josimovich2013_17-5">f</a> <a href="#cite_ref-Josimovich2013_17-6">g</a> <a href="#cite_ref-Josimovich2013_17-7">h</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJosimovich2013" class="citation book cs1">Josimovich JB (11 November 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=9vv2BwAAQBAJ&pg=PA25">Gynecologic Endocrinology</a>. Springer Science & Business Media. pp. 9, 25–29. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4613-2157-6" title="Special:BookSources/978-1-4613-2157-6"><bdi>978-1-4613-2157-6</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230114024947/https://books.google.com/books?id=9vv2BwAAQBAJ&pg=PA25">Archived</a> from the original on 14 January 2023. 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Journal of Clinical Biochemistry and Nutrition. 63 (1): 12–17. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3164%2Fjcbn.17-132">10.3164/jcbn.17-132</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6064819">6064819</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/30087538">30087538</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Clinical+Biochemistry+and+Nutrition&rft.atitle=Function+and+structural+regulation+of+the+carbon+monoxide+%28CO%29-responsive+membrane+protein+PGRMC1&rft.volume=63&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E12-%3C%2Fspan%3E17&rft.date=2018-07&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6064819%23id-name%3DPMC&rft_id=info%3Apmid%2F30087538&rft_id=info%3Adoi%2F10.3164%2Fjcbn.17-132&rft.aulast=Kabe&rft.aufirst=Y&rft.au=Handa%2C+H&rft.au=Suematsu%2C+M&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6064819&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-pmid28396637-22"><a href="#cite_ref-pmid28396637_22-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRyuKleinZanger2017" class="citation journal cs1">Ryu CS, Klein K, Zanger UM (27 March 2017). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5366339">"Membrane Associated Progesterone Receptors: Promiscuous Proteins with Pleiotropic Functions - Focus on Interactions with Cytochromes P450"</a>. 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Gulf Professional Publishing. pp. 146–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-12-440906-4" title="Special:BookSources/978-0-12-440906-4"><bdi>978-0-12-440906-4</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230114024928/https://books.google.com/books?id=TiLxa8nPbLkC&pg=PA146">Archived</a> from the original on 14 January 2023. 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Lippincott Williams & Wilkins. p. 164. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-60913-345-0" title="Special:BookSources/978-1-60913-345-0"><bdi>978-1-60913-345-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Drug+Metabolism&rft.btitle=Foye%27s+Principles+of+Medicinal+Chemistry&rft.pages=164&rft.pub=Lippincott+Williams+%26+Wilkins&rft.date=2012-01-24&rft.isbn=978-1-60913-345-0&rft.aulast=Williams&rft.aufirst=DA&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DSd6ot9ul-bUC%26pg%3DPA164&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-ScholarlyEditions2013-35"><a href="#cite_ref-ScholarlyEditions2013_35-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1"><a rel="nofollow" class="external text" href="https://books.google.com/books?id=9WdGK_3ujQMC&pg=PA4">Estrogens—Advances in Research and Application: 2013 Edition: ScholarlyBrief</a>. ScholarlyEditions. 21 June 2013. pp. 4–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4816-7550-5" title="Special:BookSources/978-1-4816-7550-5"><bdi>978-1-4816-7550-5</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230114024941/https://books.google.com/books?id=9WdGK_3ujQMC&pg=PA4">Archived</a> from the original on 14 January 2023. Retrieved 1 February 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Estrogens%E2%80%94Advances+in+Research+and+Application%3A+2013+Edition%3A+ScholarlyBrief&rft.pages=4-&rft.pub=ScholarlyEditions&rft.date=2013-06-21&rft.isbn=978-1-4816-7550-5&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D9WdGK_3ujQMC%26pg%3DPA4&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-pmid21412338-36"><a href="#cite_ref-pmid21412338_36-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFStrünkerGoodwinBrenkerKashikar2011" class="citation journal cs1">Strünker T, Goodwin N, Brenker C, Kashikar ND, Weyand I, Seifert R, Kaupp UB (March 2011). "The CatSper channel mediates progesterone-induced Ca2+ influx in human sperm". Nature. 471 (7338): 382–386. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2011Natur.471..382S">2011Natur.471..382S</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fnature09769">10.1038/nature09769</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/21412338">21412338</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:4431334">4431334</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nature&rft.atitle=The+CatSper+channel+mediates+progesterone-induced+Ca2%2B+influx+in+human+sperm&rft.volume=471&rft.issue=7338&rft.pages=%3Cspan+class%3D%22nowrap%22%3E382-%3C%2Fspan%3E386&rft.date=2011-03&rft_id=info%3Adoi%2F10.1038%2Fnature09769&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A4431334%23id-name%3DS2CID&rft_id=info%3Apmid%2F21412338&rft_id=info%3Abibcode%2F2011Natur.471..382S&rft.aulast=Str%C3%BCnker&rft.aufirst=T&rft.au=Goodwin%2C+N&rft.au=Brenker%2C+C&rft.au=Kashikar%2C+ND&rft.au=Weyand%2C+I&rft.au=Seifert%2C+R&rft.au=Kaupp%2C+UB&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-pmid21412339-37"><a href="#cite_ref-pmid21412339_37-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLishkoBotchkinaKirichok2011" class="citation journal cs1">Lishko PV, Botchkina IL, Kirichok Y (March 2011). 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Drug Discovery Today: Disease Models. 32 (Part B): 31–40. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.ddmod.2020.11.005">10.1016/j.ddmod.2020.11.005</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Drug+Discovery+Today%3A+Disease+Models&rft.atitle=Women%27s+reproductive+system+as+balanced+estradiol+and+progesterone+actions%E2%80%94A+revolutionary%2C+paradigm-shifting+concept+in+women%27s+health&rft.volume=32&rft.issue=Part+B&rft.pages=%3Cspan+class%3D%22nowrap%22%3E31-%3C%2Fspan%3E40&rft.date=2020&rft_id=info%3Adoi%2F10.1016%2Fj.ddmod.2020.11.005&rft.aulast=Prior&rft.aufirst=JC&rft_id=https%3A%2F%2Fdoi.org%2F10.1016%252Fj.ddmod.2020.11.005&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-pmid2328727-39"><a href="#cite_ref-pmid2328727_39-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKastnerKrustTurcotteStropp1990" class="citation journal cs1">Kastner P, Krust A, Turcotte B, Stropp U, Tora L, Gronemeyer H, Chambon P (May 1990). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC551856">"Two distinct estrogen-regulated promoters generate transcripts encoding the two functionally different human progesterone receptor forms A and B"</a>. The EMBO Journal. 9 (5): 1603–1614. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fj.1460-2075.1990.tb08280.x">10.1002/j.1460-2075.1990.tb08280.x</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC551856">551856</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/2328727">2328727</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+EMBO+Journal&rft.atitle=Two+distinct+estrogen-regulated+promoters+generate+transcripts+encoding+the+two+functionally+different+human+progesterone+receptor+forms+A+and+B&rft.volume=9&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1603-%3C%2Fspan%3E1614&rft.date=1990-05&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC551856%23id-name%3DPMC&rft_id=info%3Apmid%2F2328727&rft_id=info%3Adoi%2F10.1002%2Fj.1460-2075.1990.tb08280.x&rft.aulast=Kastner&rft.aufirst=P&rft.au=Krust%2C+A&rft.au=Turcotte%2C+B&rft.au=Stropp%2C+U&rft.au=Tora%2C+L&rft.au=Gronemeyer%2C+H&rft.au=Chambon%2C+P&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC551856&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-pmid16917139-40">^ <a href="#cite_ref-pmid16917139_40-0">a</a> <a href="#cite_ref-pmid16917139_40-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFClineWood2006" class="citation journal cs1">Cline JM, Wood CE (1 January 2006). Hallam SZ, Osuch JR (eds.). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=wGaKtDw50K0C&pg=PA61">"Hormonal effects on the mammary gland of postmenopausal nonhuman primates"</a>. Breast Disease. 24. IOS Press: 59–70. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3233%2Fbd-2006-24105">10.3233/bd-2006-24105</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-58603-653-9" title="Special:BookSources/978-1-58603-653-9"><bdi>978-1-58603-653-9</bdi></a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16917139">16917139</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20231127222130/https://books.google.com/books?id=wGaKtDw50K0C&pg=PA61">Archived</a> from the original on 27 November 2023. 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Elsevier. pp. 101–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-08-057109-6" title="Special:BookSources/978-0-08-057109-6"><bdi>978-0-08-057109-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Reproduction+in+Domestic+Animals&rft.pages=101-&rft.pub=Elsevier&rft.date=1991-02-20&rft.isbn=978-0-08-057109-6&rft.aulast=Cupps&rft.aufirst=PT&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dbbb-ow0N7K4C%26pg%3DPA101&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-pmid14667980-114">^ <a href="#cite_ref-pmid14667980_114-0">a</a> <a href="#cite_ref-pmid14667980_114-1">b</a> <a href="#cite_ref-pmid14667980_114-2">c</a> <a href="#cite_ref-pmid14667980_114-3">d</a> <a href="#cite_ref-pmid14667980_114-4">e</a> <a href="#cite_ref-pmid14667980_114-5">f</a> <a href="#cite_ref-pmid14667980_114-6">g</a> <a href="#cite_ref-pmid14667980_114-7">h</a> <a href="#cite_ref-pmid14667980_114-8">i</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFStanczyk2003" class="citation journal cs1">Stanczyk FZ (November 2003). 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Steroids. 68 (10–13): 879–890. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.steroids.2003.08.003">10.1016/j.steroids.2003.08.003</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/14667980">14667980</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:44601264">44601264</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Steroids&rft.atitle=All+progestins+are+not+created+equal&rft.volume=68&rft.issue=%3Cspan+class%3D%22nowrap%22%3E10%E2%80%93%3C%2Fspan%3E13&rft.pages=%3Cspan+class%3D%22nowrap%22%3E879-%3C%2Fspan%3E890&rft.date=2003-11&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A44601264%23id-name%3DS2CID&rft_id=info%3Apmid%2F14667980&rft_id=info%3Adoi%2F10.1016%2Fj.steroids.2003.08.003&rft.aulast=Stanczyk&rft.aufirst=FZ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-DowdJohnson2016-115"><a href="#cite_ref-DowdJohnson2016_115-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDowdJohnsonMariotti2016" class="citation book cs1">Dowd FJ, Johnson B, Mariotti A (3 September 2016). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=6xT7DAAAQBAJ&pg=PA448">Pharmacology and Therapeutics for Dentistry</a>. Elsevier Health Sciences. pp. 448–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-323-44595-5" title="Special:BookSources/978-0-323-44595-5"><bdi>978-0-323-44595-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Pharmacology+and+Therapeutics+for+Dentistry&rft.pages=448-&rft.pub=Elsevier+Health+Sciences&rft.date=2016-09-03&rft.isbn=978-0-323-44595-5&rft.aulast=Dowd&rft.aufirst=FJ&rft.au=Johnson%2C+B&rft.au=Mariotti%2C+A&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D6xT7DAAAQBAJ%26pg%3DPA448&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-pmid16112947-116">^ <a href="#cite_ref-pmid16112947_116-0">a</a> <a href="#cite_ref-pmid16112947_116-1">b</a> <a href="#cite_ref-pmid16112947_116-2">c</a> <a href="#cite_ref-pmid16112947_116-3">d</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKuhl2005" class="citation journal cs1">Kuhl H (August 2005). 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Climacteric. 8 (Suppl 1): 3–63. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F13697130500148875">10.1080/13697130500148875</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16112947">16112947</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:24616324">24616324</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Climacteric&rft.atitle=Pharmacology+of+estrogens+and+progestogens%3A+influence+of+different+routes+of+administration&rft.volume=8&rft.issue=Suppl+1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E3-%3C%2Fspan%3E63&rft.date=2005-08&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A24616324%23id-name%3DS2CID&rft_id=info%3Apmid%2F16112947&rft_id=info%3Adoi%2F10.1080%2F13697130500148875&rft.aulast=Kuhl&rft.aufirst=H&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-PlantZeleznik2014-117">^ <a href="#cite_ref-PlantZeleznik2014_117-0">a</a> <a href="#cite_ref-PlantZeleznik2014_117-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPlantZeleznik2014" class="citation book cs1">Plant TM, Zeleznik AJ (15 November 2014). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=I1ACBAAAQBAJ&pg=PA304">Knobil and Neill's Physiology of Reproduction</a>. Academic Press. pp. 304–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-12-397769-4" title="Special:BookSources/978-0-12-397769-4"><bdi>978-0-12-397769-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Knobil+and+Neill%27s+Physiology+of+Reproduction&rft.pages=304-&rft.pub=Academic+Press&rft.date=2014-11-15&rft.isbn=978-0-12-397769-4&rft.aulast=Plant&rft.aufirst=TM&rft.au=Zeleznik%2C+AJ&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DI1ACBAAAQBAJ%26pg%3DPA304&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-SantoroNeal-Perry2010-118">^ <a href="#cite_ref-SantoroNeal-Perry2010_118-0">a</a> <a href="#cite_ref-SantoroNeal-Perry2010_118-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSantoroNeal-Perry2010" class="citation book cs1">Santoro NF, Neal-Perry G (11 September 2010). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=4836MLkPoIYC&pg=PA13">Amenorrhea: A Case-Based, Clinical Guide</a>. Springer Science & Business Media. pp. 13–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-60327-864-5" title="Special:BookSources/978-1-60327-864-5"><bdi>978-1-60327-864-5</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230114025033/https://books.google.com/books?id=4836MLkPoIYC&pg=PA13">Archived</a> from the original on 14 January 2023. Retrieved 6 November 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Amenorrhea%3A+A+Case-Based%2C+Clinical+Guide&rft.pages=13-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2010-09-11&rft.isbn=978-1-60327-864-5&rft.aulast=Santoro&rft.aufirst=NF&rft.au=Neal-Perry%2C+G&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D4836MLkPoIYC%26pg%3DPA13&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-pmid21094889-119"><a href="#cite_ref-pmid21094889_119-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFReddy2010" class="citation book cs1">Reddy DS (2010). "Neurosteroids". Sex Differences in the Human Brain, their Underpinnings and Implications. Progress in Brain Research. Vol. 186. Elsevier. pp. 113–37. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FB978-0-444-53630-3.00008-7">10.1016/B978-0-444-53630-3.00008-7</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780444536303" title="Special:BookSources/9780444536303"><bdi>9780444536303</bdi></a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3139029">3139029</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/21094889">21094889</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Neurosteroids&rft.btitle=Sex+Differences+in+the+Human+Brain%2C+their+Underpinnings+and+Implications&rft.series=Progress+in+Brain+Research&rft.pages=%3Cspan+class%3D%22nowrap%22%3E113-%3C%2Fspan%3E37&rft.pub=Elsevier&rft.date=2010&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3139029%23id-name%3DPMC&rft_id=info%3Apmid%2F21094889&rft_id=info%3Adoi%2F10.1016%2FB978-0-444-53630-3.00008-7&rft.isbn=9780444536303&rft.aulast=Reddy&rft.aufirst=DS&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-BaulieuKelly1990-120">^ <a href="#cite_ref-BaulieuKelly1990_120-0">a</a> <a href="#cite_ref-BaulieuKelly1990_120-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBaulieuKelly1990" class="citation book cs1">Baulieu E, Kelly PA (30 November 1990). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=Seddp4-dulIC&pg=PA401">Hormones: From Molecules to Disease</a>. Springer Science & Business Media. pp. 401–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-412-02791-8" title="Special:BookSources/978-0-412-02791-8"><bdi>978-0-412-02791-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Hormones%3A+From+Molecules+to+Disease&rft.pages=401-&rft.pub=Springer+Science+%26+Business+Media&rft.date=1990-11-30&rft.isbn=978-0-412-02791-8&rft.aulast=Baulieu&rft.aufirst=E&rft.au=Kelly%2C+PA&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DSeddp4-dulIC%26pg%3DPA401&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-pmid21182831-121"><a href="#cite_ref-pmid21182831_121-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBeraničGobecRižner2011" class="citation journal cs1">Beranič N, Gobec S, Rižner TL (May 2011). 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Chemico-Biological Interactions. 191 (1–3): 227–233. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2011CBI...191..227B">2011CBI...191..227B</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.cbi.2010.12.012">10.1016/j.cbi.2010.12.012</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/21182831">21182831</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemico-Biological+Interactions&rft.atitle=Progestins+as+inhibitors+of+the+human+20-ketosteroid+reductases%2C+AKR1C1+and+AKR1C3&rft.volume=191&rft.issue=%3Cspan+class%3D%22nowrap%22%3E1%E2%80%93%3C%2Fspan%3E3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E227-%3C%2Fspan%3E233&rft.date=2011-05&rft_id=info%3Apmid%2F21182831&rft_id=info%3Adoi%2F10.1016%2Fj.cbi.2010.12.012&rft_id=info%3Abibcode%2F2011CBI...191..227B&rft.aulast=Berani%C4%8D&rft.aufirst=N&rft.au=Gobec%2C+S&rft.au=Ri%C5%BEner%2C+TL&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-pmid15492972-122"><a href="#cite_ref-pmid15492972_122-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAndersonOdegard2004" class="citation journal cs1">Anderson GD, Odegard PS (October 2004). 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CRC Press. pp. 201–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4987-0230-0" title="Special:BookSources/978-1-4987-0230-0"><bdi>978-1-4987-0230-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Integrative+Therapies+for+Depression%3A+Redefining+Models+for+Assessment%2C+Treatment+and+Prevention&rft.pages=201-&rft.pub=CRC+Press&rft.date=2016-04-27&rft.isbn=978-1-4987-0230-0&rft.aulast=Greenblatt&rft.aufirst=JM&rft.au=Brogan%2C+K&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DGpHwCgAAQBAJ%26pg%3DPA201&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-Graham2012-124"><a href="#cite_ref-Graham2012_124-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGraham2012" class="citation book cs1">Graham C (2 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=iUA0CdGhYksC&pg=PA179">Reproductive Biology of the Great Apes: Comparative and Biomedical Perspectives</a>. Elsevier. pp. 179–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-323-14971-6" title="Special:BookSources/978-0-323-14971-6"><bdi>978-0-323-14971-6</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230114024936/https://books.google.com/books?id=iUA0CdGhYksC&pg=PA179">Archived</a> from the original on 14 January 2023. 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Molecular Endocrinology. 27 (2): 315–324. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1210%2Fme.2012-1287">10.1210/me.2012-1287</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5417327">5417327</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/23322723">23322723</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Molecular+Endocrinology&rft.atitle=Structural+insights+into+aldosterone+synthase+substrate+specificity+and+targeted+inhibition&rft.volume=27&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E315-%3C%2Fspan%3E324&rft.date=2013-02&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5417327%23id-name%3DPMC&rft_id=info%3Apmid%2F23322723&rft_id=info%3Adoi%2F10.1210%2Fme.2012-1287&rft.aulast=Strushkevich&rft.aufirst=N&rft.au=Gilep%2C+AA&rft.au=Shen%2C+L&rft.au=Arrowsmith%2C+CH&rft.au=Edwards%2C+AM&rft.au=Usanov%2C+SA&rft.au=Park%2C+HW&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5417327&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-pmid29277707-126"><a href="#cite_ref-pmid29277707_126-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFvan_RooyenGentBarnardSwart2018" class="citation journal cs1">van Rooyen D, Gent R, Barnard L, Swart AC (April 2018). 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Acta Endocrinologica. 124 (1): 19–22. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1530%2Facta.0.1240019">10.1530/acta.0.1240019</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/1825737">1825737</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:9831739">9831739</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Endocrinologica&rft.atitle=Effects+of+ketoconazole+in+hirsute+women&rft.volume=124&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E19-%3C%2Fspan%3E22&rft.date=1991-01&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A9831739%23id-name%3DS2CID&rft_id=info%3Apmid%2F1825737&rft_id=info%3Adoi%2F10.1530%2Facta.0.1240019&rft.aulast=Akalin&rft.aufirst=S&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-pmid945344-129">^ <a href="#cite_ref-pmid945344_129-0">a</a> <a href="#cite_ref-pmid945344_129-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAufrèreBenson1976" class="citation journal cs1">Aufrère MB, Benson H (June 1976). 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United States National Institutes of Health. Archived from <a rel="nofollow" class="external text" href="http://cclnprod.cc.nih.gov/dlm/testguide.nsf/Index/CB26894E1EB28DEF85256BA5005B000E?OpenDocument">the original</a> on 9 January 2009. Retrieved 12 March 2008.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Progesterone+Historical+Reference+Ranges&rft.pub=United+States+National+Institutes+of+Health&rft.date=2004-08-16&rft.au=NIH+Clinical+Center&rft_id=http%3A%2F%2Fcclnprod.cc.nih.gov%2Fdlm%2Ftestguide.nsf%2FIndex%2FCB26894E1EB28DEF85256BA5005B000E%3FOpenDocument&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-Chernecky_Berger_2012-133"><a href="#cite_ref-Chernecky_Berger_2012_133-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCherneckyBerger2012" class="citation book cs1">Chernecky CC, Berger BJ (31 October 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=dWHYcOJK-cgC&pg=PA908">Laboratory Tests and Diagnostic Procedures - E-Book</a>. Elsevier Health Sciences. pp. 908–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4557-4502-9" title="Special:BookSources/978-1-4557-4502-9"><bdi>978-1-4557-4502-9</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20240227031646/https://books.google.com/books?id=dWHYcOJK-cgC&pg=PA908#v=onepage&q&f=false">Archived</a> from the original on 27 February 2024. Retrieved 23 August 2023.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Laboratory+Tests+and+Diagnostic+Procedures+-+E-Book&rft.pages=908-&rft.pub=Elsevier+Health+Sciences&rft.date=2012-10-31&rft.isbn=978-1-4557-4502-9&rft.aulast=Chernecky&rft.aufirst=CC&rft.au=Berger%2C+BJ&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DdWHYcOJK-cgC%26pg%3DPA908&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-Becker_2001-134"><a href="#cite_ref-Becker_2001_134-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBecker2001" class="citation book cs1">Becker KL (2001). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=FVfzRvaucq8C&pg=PA940">Principles and Practice of Endocrinology and Metabolism</a>. Lippincott Williams & Wilkins. pp. 889, 940. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7817-1750-2" title="Special:BookSources/978-0-7817-1750-2"><bdi>978-0-7817-1750-2</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20240227031703/https://books.google.com/books?id=FVfzRvaucq8C&pg=PA940#v=onepage&q&f=false">Archived</a> from the original on 27 February 2024. Retrieved 23 August 2023.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Principles+and+Practice+of+Endocrinology+and+Metabolism&rft.pages=889%2C+940&rft.pub=Lippincott+Williams+%26+Wilkins&rft.date=2001&rft.isbn=978-0-7817-1750-2&rft.aulast=Becker&rft.aufirst=KL&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DFVfzRvaucq8C%26pg%3DPA940&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-Josimovich2013b-135"><a href="#cite_ref-Josimovich2013b_135-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJosimovich2013" class="citation book cs1">Josimovich JB (11 November 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=9vv2BwAAQBAJ&pg=PA25">Gynecologic Endocrinology</a>. Springer Science & Business Media. pp. 9, 25–29, 139. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4613-2157-6" title="Special:BookSources/978-1-4613-2157-6"><bdi>978-1-4613-2157-6</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230114024947/https://books.google.com/books?id=9vv2BwAAQBAJ&pg=PA25">Archived</a> from the original on 14 January 2023. Retrieved 1 February 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Gynecologic+Endocrinology&rft.pages=9%2C+%3Cspan+class%3D%22nowrap%22%3E25-%3C%2Fspan%3E29%2C+139&rft.pub=Springer+Science+%26+Business+Media&rft.date=2013-11-11&rft.isbn=978-1-4613-2157-6&rft.aulast=Josimovich&rft.aufirst=JB&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D9vv2BwAAQBAJ%26pg%3DPA25&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-KeepUtian2012-136"><a href="#cite_ref-KeepUtian2012_136-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFvan_KeepUtian2012" class="citation book cs1">van Keep P, Utian W (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=0IAJBgAAQBAJ&pg=PA51">The Premenstrual Syndrome: Proceedings of a workshop held during the Sixth International Congress of Psychosomatic Obstetrics and Gynecology, Berlin, September 1980</a>. Springer Science & Business Media. pp. 51–52. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-94-011-6255-5" title="Special:BookSources/978-94-011-6255-5"><bdi>978-94-011-6255-5</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230114025337/https://books.google.com/books?id=0IAJBgAAQBAJ&pg=PA51">Archived</a> from the original on 14 January 2023. Retrieved 1 February 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Premenstrual+Syndrome%3A+Proceedings+of+a+workshop+held+during+the+Sixth+International+Congress+of+Psychosomatic+Obstetrics+and+Gynecology%2C+Berlin%2C+September+1980&rft.pages=%3Cspan+class%3D%22nowrap%22%3E51-%3C%2Fspan%3E52&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-94-011-6255-5&rft.aulast=van+Keep&rft.aufirst=P&rft.au=Utian%2C+W&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D0IAJBgAAQBAJ%26pg%3DPA51&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-StraussBarbieri2009-137"><a href="#cite_ref-StraussBarbieri2009_137-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFStraussBarbieri2009" class="citation book cs1">Strauss JF, Barbieri RL (2009). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=NudwnhxY8kYC&pg=PA807">Yen and Jaffe's Reproductive Endocrinology: Physiology, Pathophysiology, and Clinical Management</a>. Elsevier Health Sciences. pp. 807–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4160-4907-4" title="Special:BookSources/978-1-4160-4907-4"><bdi>978-1-4160-4907-4</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230110014157/https://books.google.com/books?id=NudwnhxY8kYC&pg=PA807">Archived</a> from the original on 10 January 2023. Retrieved 23 August 2023.</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%3A+Physiology%2C+Pathophysiology%2C+and+Clinical+Management&rft.pages=807-&rft.pub=Elsevier+Health+Sciences&rft.date=2009&rft.isbn=978-1-4160-4907-4&rft.aulast=Strauss&rft.aufirst=JF&rft.au=Barbieri%2C+RL&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DNudwnhxY8kYC%26pg%3DPA807&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-Bajaj_Berman2011-138"><a href="#cite_ref-Bajaj_Berman2011_138-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBajajBerman2011" class="citation book cs1">Bajaj L, Berman S (1 January 2011). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=NPhnHrDQ1_kC&pg=PA160">Berman's Pediatric Decision Making</a>. Elsevier Health Sciences. pp. 160–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-323-05405-8" title="Special:BookSources/978-0-323-05405-8"><bdi>978-0-323-05405-8</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230111143033/https://books.google.com/books?id=NPhnHrDQ1_kC&pg=PA160">Archived</a> from the original on 11 January 2023. Retrieved 23 August 2023.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Berman%27s+Pediatric+Decision+Making&rft.pages=160-&rft.pub=Elsevier+Health+Sciences&rft.date=2011-01-01&rft.isbn=978-0-323-05405-8&rft.aulast=Bajaj&rft.aufirst=L&rft.au=Berman%2C+S&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DNPhnHrDQ1_kC%26pg%3DPA160&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-Lauritzen1988-139"><a href="#cite_ref-Lauritzen1988_139-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLauritzen1988" class="citation book cs1 cs1-prop-foreign-lang-source">Lauritzen C (1988). "Natürliche und Synthetische Sexualhormone – Biologische Grundlagen und Behandlungsprinzipien" [Natural and Synthetic Sexual Hormones – Biological Basis and Medical Treatment Principles]. In Hermann P. G. Schneider, Christian Lauritzen, Eberhard Nieschlag (eds.). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=v4HvAQAACAAJ">Grundlagen und Klinik der Menschlichen Fortpflanzung</a> [Foundations and Clinic of Human Reproduction] (in German). Walter de Gruyter. pp. 229–306. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3110109689" title="Special:BookSources/978-3110109689"><bdi>978-3110109689</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/35483492">35483492</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20231001111615/https://books.google.com/books?id=v4HvAQAACAAJ">Archived</a> from the original on 1 October 2023. Retrieved 23 August 2023.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Nat%C3%BCrliche+und+Synthetische+Sexualhormone+%E2%80%93+Biologische+Grundlagen+und+Behandlungsprinzipien&rft.btitle=Grundlagen+und+Klinik+der+Menschlichen+Fortpflanzung&rft.pages=%3Cspan+class%3D%22nowrap%22%3E229-%3C%2Fspan%3E306&rft.pub=Walter+de+Gruyter&rft.date=1988&rft_id=info%3Aoclcnum%2F35483492&rft.isbn=978-3110109689&rft.aulast=Lauritzen&rft.aufirst=C&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dv4HvAQAACAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-LittleBilliar1983-140"><a href="#cite_ref-LittleBilliar1983_140-0">^</a> Little, A. B., & Billiar, R. B. (1983). Progestagens. In Endocrinology of Pregnancy, 3rd Edition (pp. 92–111). Harper and Row Philadelphia. <a rel="nofollow" class="external free" href="https://scholar.google.com/scholar?cluster=2512291948467467634">https://scholar.google.com/scholar?cluster=2512291948467467634</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20220222083312/https://scholar.google.com/scholar?cluster=2512291948467467634">Archived</a> 22 February 2022 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a> </li> <li id="cite_note-nih2009-141">^ <a href="#cite_ref-nih2009_141-0">a</a> <a href="#cite_ref-nih2009_141-1">b</a> <a href="#cite_ref-nih2009_141-2">c</a> <a href="#cite_ref-nih2009_141-3">d</a> <a href="#cite_ref-nih2009_141-4">e</a> <a href="#cite_ref-nih2009_141-5">f</a> <a href="#cite_ref-nih2009_141-6">g</a> <a href="#cite_ref-nih2009_141-7">h</a> <a href="#cite_ref-nih2009_141-8">i</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20150701024923/http://cclnprod.cc.nih.gov/dlm/testguide.nsf/0/CB26894E1EB28DEF85256BA5005B000E?OpenDocument">Progesterone Reference Ranges</a>, Performed at the Clinical Center at the National Institutes of Health, Bethesda MD, 03Feb09 </li> <li id="cite_note-mass-converted-142">^ <a href="#cite_ref-mass-converted_142-0">a</a> <a href="#cite_ref-mass-converted_142-1">b</a> <a href="#cite_ref-mass-converted_142-2">c</a> <a href="#cite_ref-mass-converted_142-3">d</a> <a href="#cite_ref-mass-converted_142-4">e</a> <a href="#cite_ref-mass-converted_142-5">f</a> <a href="#cite_ref-mass-converted_142-6">g</a> <a href="#cite_ref-mass-converted_142-7">h</a> Converted from mass values using molar mass of 314.46 g/mol </li> <li id="cite_note-Häggström2014-143"><a href="#cite_ref-Häggström2014_143-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHäggström2014" class="citation journal cs1">Häggström M (2014). <a rel="nofollow" class="external text" href="https://doi.org/10.15347%2Fwjm%2F2014.001">"Reference ranges for estradiol, progesterone, luteinizing hormone and follicle-stimulating hormone during the menstrual cycle"</a>. WikiJournal of Medicine. 1 (1). <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15347%2Fwjm%2F2014.001">10.15347/wjm/2014.001</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/2002-4436">2002-4436</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:88035135">88035135</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=WikiJournal+of+Medicine&rft.atitle=Reference+ranges+for+estradiol%2C+progesterone%2C+luteinizing+hormone+and+follicle-stimulating+hormone+during+the+menstrual+cycle&rft.volume=1&rft.issue=1&rft.date=2014&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A88035135%23id-name%3DS2CID&rft.issn=2002-4436&rft_id=info%3Adoi%2F10.15347%2Fwjm%2F2014.001&rft.aulast=H%C3%A4ggstr%C3%B6m&rft.aufirst=M&rft_id=https%3A%2F%2Fdoi.org%2F10.15347%252Fwjm%252F2014.001&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-titleResult_Content_View-144"><a href="#cite_ref-titleResult_Content_View_144-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGoodson_IIIHandagamaMoore_IIDairkee2007" class="citation web cs1">Goodson III WH, Handagama P, Moore II DH, Dairkee S (13 December 2007). <a rel="nofollow" class="external text" href="https://www.docguide.com/news/content.nsf/news/852571020057CCF6852573B1007803AD">"Milk products are a source of dietary progesterone"</a>. 30th Annual San Antonio Breast Cancer Symposium. pp. abstract # 2028. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20080920110341/http://www.docguide.com/news/content.nsf/news/852571020057CCF6852573B1007803AD">Archived</a> from the original on 20 September 2008. Retrieved 12 March 2008.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Milk+products+are+a+source+of+dietary+progesterone&rft.pages=abstract+%23+2028&rft.pub=30th+Annual+San+Antonio+Breast+Cancer+Symposium&rft.date=2007-12-13&rft.aulast=Goodson+III&rft.aufirst=WH&rft.au=Handagama%2C+P&rft.au=Moore+II%2C+DH&rft.au=Dairkee%2C+S&rft_id=http%3A%2F%2Fwww.docguide.com%2Fnews%2Fcontent.nsf%2Fnews%2F852571020057CCF6852573B1007803AD&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-pmid20108949-145"><a href="#cite_ref-pmid20108949_145-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPauliFriesenGödeckeFarnsworth2010" class="citation journal cs1">Pauli GF, Friesen JB, Gödecke T, Farnsworth NR, Glodny B (March 2010). "Occurrence of progesterone and related animal steroids in two higher plants". Journal of Natural Products. 73 (3): 338–345. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fnp9007415">10.1021/np9007415</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/20108949">20108949</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:26467578">26467578</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Natural+Products&rft.atitle=Occurrence+of+progesterone+and+related+animal+steroids+in+two+higher+plants&rft.volume=73&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E338-%3C%2Fspan%3E345&rft.date=2010-03&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A26467578%23id-name%3DS2CID&rft_id=info%3Apmid%2F20108949&rft_id=info%3Adoi%2F10.1021%2Fnp9007415&rft.aulast=Pauli&rft.aufirst=GF&rft.au=Friesen%2C+JB&rft.au=G%C3%B6decke%2C+T&rft.au=Farnsworth%2C+NR&rft.au=Glodny%2C+B&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-pmid12255132-146"><a href="#cite_ref-pmid12255132_146-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFApplezweig1969" class="citation journal cs1">Applezweig N (May 1969). 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Chemical & Pharmaceutical Bulletin. 54 (9): 1312–1314. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1248%2Fcpb.54.1312">10.1248/cpb.54.1312</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16946542">16946542</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+%26+Pharmaceutical+Bulletin&rft.atitle=Metabolism+of+tomato+steroidal+glycosides+in+humans&rft.volume=54&rft.issue=9&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1312-%3C%2Fspan%3E1314&rft.date=2006-09&rft_id=info%3Adoi%2F10.1248%2Fcpb.54.1312&rft_id=info%3Apmid%2F16946542&rft.aulast=Noguchi&rft.aufirst=E&rft.au=Fujiwara%2C+Y&rft.au=Matsushita%2C+S&rft.au=Ikeda%2C+T&rft.au=Ono%2C+M&rft.au=Nohara%2C+T&rft_id=https%3A%2F%2Fdoi.org%2F10.1248%252Fcpb.54.1312&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-pmid14558759-148"><a href="#cite_ref-pmid14558759_148-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFYangLuHwang2003" class="citation journal cs1">Yang DJ, Lu TJ, Hwang LS (October 2003). <a rel="nofollow" class="external text" href="http://ntur.lib.ntu.edu.tw/bitstream/246246/189462/1/58.pdf">"Isolation and identification of steroidal saponins in Taiwanese yam cultivar (Dioscorea pseudojaponica Yamamoto)"</a> (PDF). 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Retrieved 5 October 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Is+Menstruation+Obsolete%3F&rft.pages=31-&rft.pub=Oxford+University+Press&rft.date=1999&rft.isbn=978-0-19-513021-8&rft.aulast=Coutinho&rft.aufirst=EM&rft.au=Segal%2C+SJ&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D1ZzmCwAAQBAJ%26pg%3DPA31&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-Walker2008-172"><a href="#cite_ref-Walker2008_172-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWalker2008" class="citation book cs1">Walker A (7 March 2008). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=7HQBAwAAQBAJ&pg=PA49">The Menstrual Cycle</a>. Routledge. pp. 49–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-134-71411-7" title="Special:BookSources/978-1-134-71411-7"><bdi>978-1-134-71411-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Menstrual+Cycle&rft.pages=49-&rft.pub=Routledge&rft.date=2008-03-07&rft.isbn=978-1-134-71411-7&rft.aulast=Walker&rft.aufirst=A&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D7HQBAwAAQBAJ%26pg%3DPA49&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-Piosik-2003-173"><a href="#cite_ref-Piosik-2003_173-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPiosik2003" class="citation journal cs1">Piosik R (2003). "Adolf Butenandt und sein Wirken an der Technischen Hochschule Danzig". CHEMKON. 10 (3): 135–138. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fckon.200390038">10.1002/ckon.200390038</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=CHEMKON&rft.atitle=Adolf+Butenandt+und+sein+Wirken+an+der+Technischen+Hochschule+Danzig&rft.volume=10&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E135-%3C%2Fspan%3E138&rft.date=2003&rft_id=info%3Adoi%2F10.1002%2Fckon.200390038&rft.aulast=Piosik&rft.aufirst=R&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-Ginsburg2012-174"><a href="#cite_ref-Ginsburg2012_174-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGinsburg2012" class="citation book cs1">Ginsburg B (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=HTLoBwAAQBAJ&pg=PA274">Premenstrual Syndrome: Ethical and Legal Implications in a Biomedical Perspective</a>. Springer Science & Business Media. pp. 274–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4684-5275-4" title="Special:BookSources/978-1-4684-5275-4"><bdi>978-1-4684-5275-4</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230114025025/https://books.google.com/books?id=HTLoBwAAQBAJ&pg=PA274">Archived</a> from the original on 14 January 2023. Retrieved 5 October 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Premenstrual+Syndrome%3A+Ethical+and+Legal+Implications+in+a+Biomedical+Perspective&rft.pages=274-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-1-4684-5275-4&rft.aulast=Ginsburg&rft.aufirst=B&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DHTLoBwAAQBAJ%26pg%3DPA274&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-Rolleston1936-175"><a href="#cite_ref-Rolleston1936_175-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRolleston1936" class="citation book cs1">Rolleston HD (1936). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=tkgbAAAAIAAJ">The Endocrine Organs in Health and Disease: With an Historical Review</a>. Oxford University Press, H. Milford. p. 406. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230114024937/https://books.google.com/books?id=tkgbAAAAIAAJ">Archived</a> from the original on 14 January 2023. Retrieved 5 October 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Endocrine+Organs+in+Health+and+Disease%3A+With+an+Historical+Review&rft.pages=406&rft.pub=Oxford+University+Press%2C+H.+Milford&rft.date=1936&rft.aulast=Rolleston&rft.aufirst=HD&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DtkgbAAAAIAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-pmid4922128-176"><a href="#cite_ref-pmid4922128_176-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAllen1970" class="citation journal cs1">Allen WM (October 1970). "Progesterone: how did the name originate?". Southern Medical Journal. 63 (10): 1151–1155. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1097%2F00007611-197010000-00012">10.1097/00007611-197010000-00012</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/4922128">4922128</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:35867375">35867375</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Southern+Medical+Journal&rft.atitle=Progesterone%3A+how+did+the+name+originate%3F&rft.volume=63&rft.issue=10&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1151-%3C%2Fspan%3E1155&rft.date=1970-10&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A35867375%23id-name%3DS2CID&rft_id=info%3Apmid%2F4922128&rft_id=info%3Adoi%2F10.1097%2F00007611-197010000-00012&rft.aulast=Allen&rft.aufirst=WM&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-Refsal-2009-177"><a href="#cite_ref-Refsal-2009_177-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRefsal2009" class="citation journal cs1">Refsal K (February 2009). <a rel="nofollow" class="external text" href="https://www.dcpah.msu.edu/sections/endocrinology/Progesterone_Guidelines.pdf">"Interpretation of Serum Progesterone Results for Management of Breeding in Dogs"</a> (PDF). Webcd.endo.ref. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210829011032/https://cvm.msu.edu/vdl">Archived</a> from the original on 29 August 2021. Retrieved 26 February 2018.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Webcd.endo.ref&rft.atitle=Interpretation+of+Serum+Progesterone+Results+for+Management+of+Breeding+in+Dogs&rft.date=2009-02&rft.aulast=Refsal&rft.aufirst=K&rft_id=https%3A%2F%2Fwww.dcpah.msu.edu%2Fsections%2Fendocrinology%2FProgesterone_Guidelines.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-www.goodrx.com-prices-178"><a href="#cite_ref-www.goodrx.com-prices_178-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.goodrx.com/progesterone">"Progesterone Prices, Coupons & Savings Tips - GoodRx"</a>. www.goodrx.com. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230330054318/https://www.goodrx.com/progesterone">Archived</a> from the original on 30 March 2023. Retrieved 1 August 2023.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=www.goodrx.com&rft.atitle=Progesterone+Prices%2C+Coupons+%26+Savings+Tips+-+GoodRx&rft_id=https%3A%2F%2Fwww.goodrx.com%2Fprogesterone&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> <li id="cite_note-www.goodrx.com-prices-2-179"><a href="#cite_ref-www.goodrx.com-prices-2_179-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.goodrx.com/progesterone">"Progesterone Prices, Coupons & Savings Tips - GoodRx"</a>. www.goodrx.com. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230330054318/https://www.goodrx.com/progesterone">Archived</a> from the original on 30 March 2023. Retrieved 1 August 2023.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=www.goodrx.com&rft.atitle=Progesterone+Prices%2C+Coupons+%26+Savings+Tips+-+GoodRx&rft_id=https%3A%2F%2Fwww.goodrx.com%2Fprogesterone&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProgesterone" class="Z3988"> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2>[<a href="/w/index.php?title=Progesterone&action=edit&section=39" title="Edit section: External links">edit</a>]</div> <ul><li><a rel="nofollow" class="external text" href="http://gmd.mpimp-golm.mpg.de/Spectrums/5e8993d3-17a1-4a05-96f5-03ba3c2270af.aspx">Progesterone MS Spectrum</a></li> <li><a rel="nofollow" class="external text" href="https://meshb.nlm.nih.gov/record/ui?name=Progesterone">Progesterone</a> at the U.S. National Library of Medicine <a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">Medical Subject Headings</a> (MeSH)</li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKimball2007" class="citation web cs1">Kimball JW (27 May 2007). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20080618062909/http://users.rcn.com/jkimball.ma.ultranet/BiologyPages/P/Progesterone.html">"Progesterone"</a>. Kimball's Biology Pages. Archived from <a rel="nofollow" class="external text" href="http://users.rcn.com/jkimball.ma.ultranet/BiologyPages/P/Progesterone.html">the original</a> on 18 June 2008. 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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 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– 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">T3</a></li> <li><a href="/wiki/Thyroxine" title="Thyroxine">T4</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 class="mw-selflink selflink">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 href="/wiki/Estrogen" title="Estrogen">Estrogen</a></li> <li><a class="mw-selflink selflink">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">22R-Hydroxycholesterol</a></li> <li><a href="/wiki/20%CE%B1,22R-Dihydroxycholesterol" title="20α,22R-Dihydroxycholesterol">20α,22R-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 class="mw-selflink selflink">Progesterone</a></li></ul> <ul><li>Metabolites: <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>Metabolites: <a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/wiki/3%CE%B1-Androstanediol_glucuronide" class="mw-redirect" title="3α-Androstanediol glucuronide">3α-Androstanediol glucuronide</a></li> <li><a href="/wiki/3%CE%B2-Androstanediol" title="3β-Androstanediol">3β-Androstanediol</a></li> <li><a href="/wiki/5%CE%B2-Dihydrotestosterone" title="5β-Dihydrotestosterone">5β-Dihydrotestosterone</a></li> <li><a href="/wiki/3%CE%B1-Etiocholanediol" title="3α-Etiocholanediol">3α-Etiocholanediol</a></li> <li><a href="/wiki/3%CE%B2-Etiocholanediol" title="3β-Etiocholanediol">3β-Etiocholanediol</a></li> <li><a href="/w/index.php?title=Androstanetriol&action=edit&redlink=1" class="new" title="Androstanetriol (page does not exist)">Androstanetriols</a></li> <li><a href="/wiki/Androstenediol_sulfate" title="Androstenediol sulfate">Androstenediol sulfate</a></li> <li><a href="/wiki/Androstenetriol" title="Androstenetriol">Androstenetriol</a></li> <li><a href="/wiki/Androsterone_glucuronide" title="Androsterone glucuronide">Androsterone glucuronide</a></li> <li><a href="/wiki/Androsterone_sulfate" title="Androsterone sulfate">Androsterone sulfate</a></li> <li><a href="/w/index.php?title=Dihydrotestosterone_glucuronide&action=edit&redlink=1" class="new" title="Dihydrotestosterone glucuronide (page does not exist)">Dihydrotestosterone glucuronide</a></li> <li><a href="/w/index.php?title=Dihydrotestosterone_sulfate&action=edit&redlink=1" class="new" title="Dihydrotestosterone sulfate (page does not exist)">Dihydrotestosterone sulfate</a></li> <li><a href="/wiki/Etiocholanedione" title="Etiocholanedione">Etiocholanedione</a></li> <li><a href="/wiki/Etiocholanolone" title="Etiocholanolone">Etiocholanolone</a></li> <li><a href="/wiki/Etiocholanolone_glucuronide" title="Etiocholanolone glucuronide">Etiocholanolone glucuronide</a></li> <li><a href="/wiki/Epietiocholanolone" title="Epietiocholanolone">Epietiocholanolone</a></li> <li><a href="/wiki/Testosterone_glucuronide" title="Testosterone glucuronide">Testosterone glucuronide</a></li> <li><a href="/wiki/Testosterone_sulfate" title="Testosterone sulfate">Testosterone sulfate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Estrogen" title="Estrogen">Estrogens</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Estranes: <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>Others: <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>Metabolites: <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 class="mw-selflink selflink">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>Metabolites: <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>Cholestanes: <a href="/wiki/24S-hydroxycholesterol" class="mw-redirect" title="24S-hydroxycholesterol">24S-Hydroxycholesterol</a></li> <li><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></li></ul> <ul><li>Pregnanes: <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 class="mw-selflink selflink">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>Androstanes: <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><a href="/wiki/Pheromone" title="Pheromone">Pheromones</a>: <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><a href="/wiki/Vitamin_D" title="Vitamin D">Vitamin D</a>: <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>Others: <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="Progestogens_and_antiprogestogens153" 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:Progestogens_and_antiprogestogens" title="Template:Progestogens and antiprogestogens"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Progestogens_and_antiprogestogens" title="Template talk:Progestogens and antiprogestogens"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Progestogens_and_antiprogestogens" title="Special:EditPage/Template:Progestogens and antiprogestogens"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Progestogens_and_antiprogestogens153" style="font-size:114%;margin:0 4em"><a href="/wiki/Progestogen_(medication)" title="Progestogen (medication)">Progestogens</a> and <a href="/wiki/Antiprogestogen" title="Antiprogestogen">antiprogestogens</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Progestogen_(medication)" title="Progestogen (medication)">Progestogens</a> (and <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestins</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 id="PRTooltip_Progesterone_receptor_agonists408" scope="row" class="navbox-group" style="width:8em;;text-align:center;"><a href="/wiki/Progesterone_receptor" title="Progesterone receptor"><abbr title="Progesterone receptor">PR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Progesterone receptor <a href="/wiki/Agonist" title="Agonist">agonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Progesterone derivatives: <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">Progesterone</a></li> <li><a href="/wiki/Quingestrone" title="Quingestrone">Quingestrone</a></li></ul> <ul><li>Retroprogesterone derivatives: <a href="/wiki/Dydrogesterone" title="Dydrogesterone">Dydrogesterone</a></li> <li><a href="/wiki/Trengestone" title="Trengestone">Trengestone</a></li></ul> <ul><li>17α-Hydroxyprogesterone (and closely related) derivatives: 17α-Hydroxylated: <a href="/wiki/Acetomepregenol" title="Acetomepregenol">Acetomepregenol (mepregenol diacetate)</a></li> <li><a href="/wiki/Algestone_acetophenide" title="Algestone acetophenide">Algestone acetophenide (dihydroxyprogesterone acetophenide)</a></li> <li><a href="/wiki/Anagestone_acetate" title="Anagestone acetate">Anagestone acetate</a></li> <li><a href="/wiki/Chlormadinone_acetate" title="Chlormadinone acetate">Chlormadinone acetate</a></li> <li><a href="/wiki/Chlormethenmadinone_acetate" title="Chlormethenmadinone acetate">Chlormethenmadinone acetate</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Delmadinone_acetate" title="Delmadinone acetate">Delmadinone acetate</a></li> <li><a href="/wiki/Flugestone_acetate" title="Flugestone acetate">Flugestone acetate (flurogestone acetate)</a></li> <li><a href="/wiki/Flumedroxone_acetate" title="Flumedroxone acetate">Flumedroxone acetate</a></li> <li><a href="/wiki/Hydroxyprogesterone_acetate" title="Hydroxyprogesterone acetate">Hydroxyprogesterone acetate</a></li> <li><a href="/wiki/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">Hydroxyprogesterone caproate</a></li> <li><a href="/wiki/Hydroxyprogesterone_heptanoate" title="Hydroxyprogesterone heptanoate">Hydroxyprogesterone heptanoate</a></li> <li><a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">Medroxyprogesterone acetate</a>#</li> <li><a href="/wiki/Megestrol_acetate" title="Megestrol acetate">Megestrol acetate</a></li> <li><a href="/wiki/Melengestrol_acetate" title="Melengestrol acetate">Melengestrol acetate</a></li> <li><a href="/wiki/Methenmadinone_acetate" title="Methenmadinone acetate">Methenmadinone acetate</a></li> <li><a href="/wiki/Osaterone_acetate" title="Osaterone acetate">Osaterone acetate</a></li> <li><a href="/wiki/Pentagestrone_acetate" title="Pentagestrone acetate">Pentagestrone acetate</a></li> <li><a href="/wiki/Proligestone" title="Proligestone">Proligestone</a>; 17α-Methylated: <a href="/wiki/Medrogestone" title="Medrogestone">Medrogestone</a>; Others: <a href="/wiki/Haloprogesterone" title="Haloprogesterone">Haloprogesterone</a></li></ul> <ul><li>19-Norprogesterone derivatives: 17α-Hydroxylated: <a href="/wiki/Gestonorone_caproate" title="Gestonorone caproate">Gestonorone caproate (gestronol hexanoate)</a></li> <li><a href="/wiki/Nomegestrol_acetate" title="Nomegestrol acetate">Nomegestrol acetate</a></li> <li><a href="/wiki/Norgestomet" title="Norgestomet">Norgestomet</a></li> <li><a href="/wiki/Segesterone_acetate" title="Segesterone acetate">Segesterone acetate (nestorone, elcometrine)</a>; 17α-Methylated: <a href="/wiki/Demegestone" title="Demegestone">Demegestone</a></li> <li><a href="/wiki/Promegestone" title="Promegestone">Promegestone</a></li> <li><a href="/wiki/Trimegestone" title="Trimegestone">Trimegestone</a></li></ul> <ul><li>Testosterone derivatives: Estranes: <a href="/wiki/Danazol" title="Danazol">Danazol</a></li> <li><a href="/wiki/Dimethisterone" title="Dimethisterone">Dimethisterone</a></li> <li><a href="/wiki/Ethisterone" title="Ethisterone">Ethisterone</a></li></ul> <ul><li>19-Nortestosterone derivatives: Estranes: <a href="/wiki/Allylestrenol" title="Allylestrenol">Allylestrenol</a></li> <li><a href="/wiki/Altrenogest" title="Altrenogest">Altrenogest</a></li> <li><a href="/wiki/Dienogest" title="Dienogest">Dienogest</a></li> <li><a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">Etynodiol diacetate</a></li> <li><a href="/wiki/Lynestrenol" title="Lynestrenol">Lynestrenol</a></li> <li><a href="/wiki/Norethisterone" title="Norethisterone">Norethisterone (norethindrone)</a>#</li> <li><a href="/wiki/Norethisterone_acetate" title="Norethisterone acetate">Norethisterone acetate</a></li> <li><a href="/wiki/Norethisterone_enanthate" title="Norethisterone enanthate">Norethisterone enanthate</a></li> <li><a href="/wiki/Noretynodrel" title="Noretynodrel">Noretynodrel</a></li> <li><a href="/wiki/Norgesterone" title="Norgesterone">Norgesterone</a></li> <li><a href="/wiki/Norgestrienone" title="Norgestrienone">Norgestrienone</a></li> <li><a href="/wiki/Normethandrone" title="Normethandrone">Normethandrone (methylestrenolone)</a></li> <li><a href="/wiki/Norvinisterone" title="Norvinisterone">Norvinisterone</a></li> <li><a href="/wiki/Oxendolone" title="Oxendolone">Oxendolone</a></li> <li><a href="/wiki/Quingestanol_acetate" title="Quingestanol acetate">Quingestanol acetate</a></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a>; Gonanes: <a href="/wiki/Desogestrel" title="Desogestrel">Desogestrel</a></li> <li><a href="/wiki/Etonogestrel" title="Etonogestrel">Etonogestrel</a></li> <li><a href="/wiki/Gestodene" title="Gestodene">Gestodene</a></li> <li><a href="/wiki/Gestrinone" title="Gestrinone">Gestrinone</a></li> <li><a href="/wiki/Levonorgestrel" title="Levonorgestrel">Levonorgestrel</a>#</li> <li><a href="/wiki/Norelgestromin" title="Norelgestromin">Norelgestromin</a></li> <li><a href="/wiki/Norgestimate" title="Norgestimate">Norgestimate</a></li> <li><a href="/wiki/Norgestrel" title="Norgestrel">Norgestrel</a></li></ul> <ul><li>Spirolactone derivatives: <a href="/wiki/Drospirenone" title="Drospirenone">Drospirenone</a></li></ul> <ul><li>Others: <a href="/wiki/Anabolic%E2%80%93androgenic_steroid" class="mw-redirect" title="Anabolic–androgenic steroid">Anabolic–androgenic steroids</a> (e.g., <a href="/wiki/Nandrolone" title="Nandrolone">nandrolone</a> and <a href="/wiki/Nandrolone_ester" class="mw-redirect" title="Nandrolone ester">esters</a>, <a href="/wiki/Trenbolone" title="Trenbolone">trenbolone</a> and <a href="/wiki/Trenbolone_ester" class="mw-redirect" title="Trenbolone ester">esters</a>, <a href="/wiki/Ethylestrenol" title="Ethylestrenol">ethylestrenol</a>, <a href="/wiki/Norethandrolone" title="Norethandrolone">norethandrolone</a>, others)</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/Antiprogestogen" title="Antiprogestogen">Antiprogestogens</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:8em;;text-align:center;"><a href="/wiki/Selective_progesterone_receptor_modulators" class="mw-redirect" title="Selective progesterone receptor modulators"><abbr title="Selective progesterone receptor modulators">SPRMs</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 progesterone receptor modulators</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Telapristone" title="Telapristone">Telapristone</a>§</li> <li><a href="/wiki/Ulipristal_acetate" title="Ulipristal acetate">Ulipristal acetate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8em;;text-align:center;"><a href="/wiki/Progesterone_receptor" title="Progesterone receptor"><abbr title="Progesterone receptor">PR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Progesterone receptor <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonists</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/Aglepristone" title="Aglepristone">Aglepristone</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td colspan="2" class="navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><div class="hlist"> <ul><li>#<a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li>‡<a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li>†<a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li>§Never to phase III</li></ul></li></ul> </div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Progesterone_receptor_modulators" title="Template:Progesterone receptor modulators">Progesterone 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:Estrogens_and_antiestrogens" title="Template:Estrogens and antiestrogens">Estrogens and antiestrogens</a></dd> <dd><a href="/wiki/List_of_steroidal_progestogens" class="mw-redirect" title="List of steroidal progestogens">List of progestogens</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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Mineralocorticoids_and_antimineralocorticoids_(H02)173" 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:Mineralocorticoids_and_antimineralocorticoids" title="Template:Mineralocorticoids and antimineralocorticoids"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Mineralocorticoids_and_antimineralocorticoids" title="Template talk:Mineralocorticoids and antimineralocorticoids"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Mineralocorticoids_and_antimineralocorticoids" title="Special:EditPage/Template:Mineralocorticoids and antimineralocorticoids"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Mineralocorticoids_and_antimineralocorticoids_(H02)173" style="font-size:114%;margin:0 4em"><a href="/wiki/Mineralocorticoid" title="Mineralocorticoid">Mineralocorticoids</a> and <a href="/wiki/Antimineralocorticoid" class="mw-redirect" title="Antimineralocorticoid">antimineralocorticoids</a> (<a href="/wiki/ATC_code_H02" title="ATC code H02">H02</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Mineralocorticoid" title="Mineralocorticoid">Mineralocorticoids</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/Deoxycortone" class="mw-redirect" title="Deoxycortone">Desoxycortone (desoxycorticosterone)</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Desoxycortone_esters" title="List of corticosteroid esters">Desoxycortone esters</a></li></ul></li> <li><a href="/wiki/Hydrocortisone" title="Hydrocortisone">Hydrocortisone (cortisol)</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Hydrocortisone_esters" title="List of corticosteroid esters">Hydrocortisone esters</a></li></ul></li> <li><a href="/wiki/Fludrocortisone" title="Fludrocortisone">Fludrocortisone</a> <ul><li><a href="/wiki/Fludrocortisone_acetate" class="mw-redirect" title="Fludrocortisone acetate">Fludrocortisone acetate</a></li></ul></li> <li><a href="/wiki/Methylprednisolone" title="Methylprednisolone">Methylprednisolone</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Methylprednisolone_esters" title="List of corticosteroid esters">Methylprednisolone esters</a></li></ul></li> <li><a href="/wiki/Prednisolone" title="Prednisolone">Prednisolone</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Prednisolone_esters" title="List of corticosteroid esters">Prednisolone esters</a></li></ul></li> <li><a href="/wiki/Prednisone" title="Prednisone">Prednisone</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Prednisone_esters" title="List of corticosteroid esters">Prednisone esters</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Antimineralocorticoid" class="mw-redirect" title="Antimineralocorticoid">Antimineralocorticoids</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>Steroidal: <a href="/wiki/Potassium_canrenoate" title="Potassium canrenoate">Canrenoate potassium (potassium canrenoate)</a></li> <li><a href="/wiki/Canrenone" title="Canrenone">Canrenone</a></li> <li><a href="/wiki/Drospirenone" title="Drospirenone">Drospirenone</a></li> <li><a href="/wiki/Dydrogesterone" title="Dydrogesterone">Dydrogesterone</a></li> <li><a href="/wiki/Eplerenone" title="Eplerenone">Eplerenone</a></li> <li><a href="/wiki/Gestodene" title="Gestodene">Gestodene</a></li> <li><a href="/wiki/Medrogestone" title="Medrogestone">Medrogestone</a></li> <li><a class="mw-selflink selflink">Progesterone</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/wiki/Trimegestone" title="Trimegestone">Trimegestone</a></li></ul> <ul><li>Nonsteroidal: <a href="/wiki/Amlodipine" title="Amlodipine">Amlodipine</a></li> <li><a href="/wiki/Apararenone" title="Apararenone">Apararenone</a>§</li> <li><a href="/wiki/Benidipine" title="Benidipine">Benidipine</a></li> <li><a href="/wiki/Esaxerenone" title="Esaxerenone">Esaxerenone</a>†</li> <li><a href="/wiki/Felodipine" title="Felodipine">Felodipine</a></li> <li><a href="/wiki/Finerenone" title="Finerenone">Finerenone</a></li> <li><a href="/wiki/Nifedipine" title="Nifedipine">Nifedipine</a></li> <li><a href="/wiki/Nimodipine" title="Nimodipine">Nimodipine</a></li> <li><a href="/wiki/Nitrendipine" title="Nitrendipine">Nitrendipine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Steroidogenesis_inhibitor" title="Steroidogenesis inhibitor">Synthesis modifiers</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/Acetoxolone" title="Acetoxolone">Acetoxolone</a></li> <li><a href="/wiki/Aminoglutethimide" title="Aminoglutethimide">Aminoglutethimide</a></li> <li><a href="/wiki/Carbenoxolone" title="Carbenoxolone">Carbenoxolone</a></li> <li><a href="/wiki/Enoxolone" title="Enoxolone">Enoxolone</a></li> <li><a href="/wiki/Ketoconazole" title="Ketoconazole">Ketoconazole</a></li> <li><a href="/wiki/Metyrapone" title="Metyrapone">Metyrapone</a></li> <li><a href="/wiki/Mitotane" title="Mitotane">Mitotane</a></li> <li><a href="/wiki/Trilostane" title="Trilostane">Trilostane</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><div class="hlist"> <ul><li>#<a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li>‡<a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li>†<a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li>§Never to phase III</li></ul></li></ul> </div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Mineralocorticoid_receptor_modulators" title="Template:Mineralocorticoid receptor modulators">Mineralocorticoid receptor modulators</a></dd> <dd><a href="/wiki/Template:Glucocorticoids_and_antiglucocorticoids" title="Template:Glucocorticoids and antiglucocorticoids">Glucocorticoids and antiglucocorticoids</a></dd> <dd><a href="/wiki/List_of_corticosteroids" title="List of corticosteroids">List of corticosteroids</a></dd></dl></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Biological_activity108" 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" style="background:#e8e8ff;background:#ccccff"><div id="Biological_activity108" style="font-size:114%;margin:0 4em"><a href="/wiki/Biological_activity" title="Biological activity">Biological activity</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;font-size:114%"><div style="padding:0px"> <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="GABAA_receptor_positive_modulators746" 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:GABAA_receptor_positive_modulators" title="Template:GABAA receptor positive modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:GABAA_receptor_positive_modulators" title="Template talk:GABAA receptor positive modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:GABAA_receptor_positive_modulators" title="Special:EditPage/Template:GABAA receptor positive modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="GABAA_receptor_positive_modulators746" style="font-size:114%;margin:0 4em"><a href="/wiki/GABAA_receptor_positive_allosteric_modulator" title="GABAA receptor positive allosteric modulator"><abbr title="γ-Aminobutyric acid">GABA</abbr>A receptor positive modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohols</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="/w/index.php?title=Brometone&action=edit&redlink=1" class="new" title="Brometone (page does not exist)">Brometone</a></li> <li><a href="/wiki/1-Butanol" title="1-Butanol">Butanol</a></li> <li><a href="/wiki/Chloralodol" title="Chloralodol">Chloralodol</a></li> <li><a href="/wiki/Chlorobutanol" title="Chlorobutanol">Chlorobutanol (cloretone)</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a> (<a href="/wiki/Alcoholic_drink" class="mw-redirect" title="Alcoholic drink">alcoholic drink</a>)</li> <li><a href="/wiki/Ethchlorvynol" title="Ethchlorvynol">Ethchlorvynol</a></li> <li><a href="/wiki/Isobutanol" title="Isobutanol">Isobutanol</a></li> <li><a href="/wiki/Isopropanol" class="mw-redirect" title="Isopropanol">Isopropanol</a></li> <li><a href="/wiki/Menthol" title="Menthol">Menthol</a></li> <li><a href="/wiki/Methanol" title="Methanol">Methanol</a></li> <li><a href="/wiki/Methylpentynol" title="Methylpentynol">Methylpentynol</a></li> <li><a href="/wiki/1-Pentanol" title="1-Pentanol">Pentanol</a></li> <li><a href="/wiki/Petrichloral" title="Petrichloral">Petrichloral</a></li> <li><a href="/wiki/1-Propanol" title="1-Propanol">Propanol</a></li> <li><a href="/wiki/Tert-Butanol" class="mw-redirect" title="Tert-Butanol">tert-Butanol (2M2P)</a></li> <li><a href="/wiki/Tert-Pentanol" class="mw-redirect" title="Tert-Pentanol">tert-Pentanol (2M2B)</a></li> <li><a href="/wiki/Tribromoethanol" title="Tribromoethanol">Tribromoethanol</a></li> <li><a href="/wiki/Trichloroethanol" class="mw-redirect" title="Trichloroethanol">Trichloroethanol</a></li> <li><a href="/wiki/Triclofos" title="Triclofos">Triclofos</a></li> <li><a href="/wiki/Trifluoroethanol" class="mw-redirect" title="Trifluoroethanol">Trifluoroethanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Barbiturate" title="Barbiturate">Barbiturates</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/(-)-5-(1,3-Dimethylbutyl)-5-ethylbarbituric_acid" class="mw-redirect" title="(-)-5-(1,3-Dimethylbutyl)-5-ethylbarbituric acid">(-)-DMBB</a></li> <li><a href="/wiki/Allobarbital" title="Allobarbital">Allobarbital</a></li> <li><a href="/wiki/Alphenal" title="Alphenal">Alphenal</a></li> <li><a href="/wiki/Amobarbital" title="Amobarbital">Amobarbital</a></li> <li><a href="/wiki/Aprobarbital" title="Aprobarbital">Aprobarbital</a></li> <li><a href="/wiki/Barbexaclone" title="Barbexaclone">Barbexaclone</a></li> <li><a href="/wiki/Barbital" title="Barbital">Barbital</a></li> <li><a href="/wiki/Benzobarbital" title="Benzobarbital">Benzobarbital</a></li> <li><a href="/wiki/Benzylbutylbarbiturate" title="Benzylbutylbarbiturate">Benzylbutylbarbiturate</a></li> <li><a href="/wiki/Brallobarbital" title="Brallobarbital">Brallobarbital</a></li> <li><a href="/wiki/Brophebarbital" title="Brophebarbital">Brophebarbital</a></li> <li><a href="/wiki/Butabarbital" title="Butabarbital">Butabarbital/Secbutabarbital</a></li> <li><a href="/wiki/Butalbital" title="Butalbital">Butalbital</a></li> <li><a href="/wiki/Buthalital" title="Buthalital">Buthalital</a></li> <li><a href="/wiki/Butobarbital" title="Butobarbital">Butobarbital</a></li> <li><a href="/wiki/Butallylonal" title="Butallylonal">Butallylonal</a></li> <li><a href="/wiki/Carbubarb" title="Carbubarb">Carbubarb</a></li> <li><a href="/wiki/Crotylbarbital" title="Crotylbarbital">Crotylbarbital</a></li> <li><a href="/wiki/Cyclobarbital" title="Cyclobarbital">Cyclobarbital</a></li> <li><a href="/wiki/Cyclopentobarbital" title="Cyclopentobarbital">Cyclopentobarbital</a></li> <li><a href="/wiki/Difebarbamate" title="Difebarbamate">Difebarbamate</a></li> <li><a href="/wiki/Enallylpropymal" title="Enallylpropymal">Enallylpropymal</a></li> <li><a href="/wiki/Ethallobarbital" title="Ethallobarbital">Ethallobarbital</a></li> <li><a href="/wiki/Eterobarb" title="Eterobarb">Eterobarb</a></li> <li><a href="/wiki/Febarbamate" title="Febarbamate">Febarbamate</a></li> <li><a href="/wiki/Heptabarb" title="Heptabarb">Heptabarb</a></li> <li><a href="/wiki/Heptobarbital" title="Heptobarbital">Heptobarbital</a></li> <li><a href="/wiki/Hexethal" title="Hexethal">Hexethal</a></li> <li><a href="/wiki/Hexobarbital" title="Hexobarbital">Hexobarbital</a></li> <li><a href="/wiki/Metharbital" title="Metharbital">Metharbital</a></li> <li><a href="/wiki/Methitural" title="Methitural">Methitural</a></li> <li><a href="/wiki/Methohexital" title="Methohexital">Methohexital</a></li> <li><a href="/wiki/Methylphenobarbital" title="Methylphenobarbital">Methylphenobarbital</a></li> <li><a href="/wiki/Narcobarbital" title="Narcobarbital">Narcobarbital</a></li> <li><a href="/wiki/Nealbarbital" title="Nealbarbital">Nealbarbital</a></li> <li><a href="/wiki/Pentobarbital" title="Pentobarbital">Pentobarbital</a></li> <li><a href="/wiki/Phenallymal" class="mw-redirect" title="Phenallymal">Phenallymal</a></li> <li><a href="/wiki/Phenobarbital" title="Phenobarbital">Phenobarbital</a></li> <li><a href="/wiki/Phetharbital" title="Phetharbital">Phetharbital</a></li> <li><a href="/wiki/Primidone" title="Primidone">Primidone</a></li> <li><a href="/wiki/Probarbital" title="Probarbital">Probarbital</a></li> <li><a href="/wiki/Propallylonal" title="Propallylonal">Propallylonal</a></li> <li><a href="/wiki/Propylbarbital" title="Propylbarbital">Propylbarbital</a></li> <li><a href="/wiki/Proxibarbital" title="Proxibarbital">Proxibarbital</a></li> <li><a href="/wiki/Reposal" title="Reposal">Reposal</a></li> <li><a href="/wiki/Secobarbital" title="Secobarbital">Secobarbital</a></li> <li><a href="/wiki/Sigmodal" title="Sigmodal">Sigmodal</a></li> <li><a href="/wiki/Spirobarbital" title="Spirobarbital">Spirobarbital</a></li> <li><a href="/wiki/Talbutal" title="Talbutal">Talbutal</a></li> <li><a href="/wiki/Tetrabamate" title="Tetrabamate">Tetrabamate</a></li> <li><a href="/wiki/Tetrabarbital" title="Tetrabarbital">Tetrabarbital</a></li> <li><a href="/wiki/Thialbarbital" title="Thialbarbital">Thialbarbital</a></li> <li><a href="/wiki/Thiamylal" title="Thiamylal">Thiamylal</a></li> <li><a href="/wiki/Thiobarbital" title="Thiobarbital">Thiobarbital</a></li> <li><a href="/wiki/Thiobutabarbital" title="Thiobutabarbital">Thiobutabarbital</a></li> <li><a href="/wiki/Sodium_thiopental" title="Sodium thiopental">Thiopental</a></li> <li><a href="/wiki/Thiotetrabarbital" title="Thiotetrabarbital">Thiotetrabarbital</a></li> <li><a href="/wiki/Valofane" title="Valofane">Valofane</a></li> <li><a href="/wiki/Vinbarbital" title="Vinbarbital">Vinbarbital</a></li> <li><a href="/wiki/Vinylbital" title="Vinylbital">Vinylbital</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</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/2-Oxoquazepam" title="2-Oxoquazepam">2-Oxoquazepam</a></li> <li><a href="/wiki/3-Hydroxyphenazepam" title="3-Hydroxyphenazepam">3-Hydroxyphenazepam</a></li> <li><a href="/wiki/Adinazolam" title="Adinazolam">Adinazolam</a></li> <li><a href="/wiki/Alprazolam" title="Alprazolam">Alprazolam</a></li> <li><a href="/wiki/Arfendazam" title="Arfendazam">Arfendazam</a></li> <li><a href="/wiki/Avizafone" title="Avizafone">Avizafone</a></li> <li><a href="/wiki/Bentazepam" title="Bentazepam">Bentazepam</a></li> <li><a href="/wiki/Bretazenil" title="Bretazenil">Bretazenil</a></li> <li><a href="/wiki/Bromazepam" title="Bromazepam">Bromazepam</a></li> <li><a href="/wiki/Bromazolam" title="Bromazolam">Bromazolam</a></li> <li><a href="/wiki/Brotizolam" title="Brotizolam">Brotizolam</a></li> <li><a href="/wiki/Camazepam" title="Camazepam">Camazepam</a></li> <li><a href="/wiki/Carburazepam" title="Carburazepam">Carburazepam</a></li> <li><a href="/wiki/Chlordiazepoxide" title="Chlordiazepoxide">Chlordiazepoxide</a></li> <li><a href="/wiki/Ciclotizolam" title="Ciclotizolam">Ciclotizolam</a></li> <li><a href="/wiki/Cinazepam" title="Cinazepam">Cinazepam</a></li> <li><a href="/wiki/Cinolazepam" title="Cinolazepam">Cinolazepam</a></li> <li><a href="/wiki/Clazolam" title="Clazolam">Clazolam</a></li> <li><a href="/wiki/Climazolam" title="Climazolam">Climazolam</a></li> <li><a href="/wiki/Clobazam" title="Clobazam">Clobazam</a></li> <li><a href="/wiki/Clonazepam" title="Clonazepam">Clonazepam</a></li> <li><a href="/wiki/Clonazolam" title="Clonazolam">Clonazolam</a></li> <li><a href="/wiki/Cloniprazepam" title="Cloniprazepam">Cloniprazepam</a></li> <li><a href="/wiki/Clorazepate" title="Clorazepate">Clorazepate</a></li> <li><a href="/wiki/Clotiazepam" title="Clotiazepam">Clotiazepam</a></li> <li><a href="/wiki/Cloxazolam" title="Cloxazolam">Cloxazolam</a></li> <li><a href="/wiki/CP-1414S" title="CP-1414S">CP-1414S</a></li> <li><a href="/wiki/Cyprazepam" title="Cyprazepam">Cyprazepam</a></li> <li><a href="/wiki/Delorazepam" title="Delorazepam">Delorazepam</a></li> <li><a href="/wiki/Demoxepam" title="Demoxepam">Demoxepam</a></li> <li><a href="/wiki/Diazepam" title="Diazepam">Diazepam</a></li> <li><a href="/wiki/Diclazepam" title="Diclazepam">Diclazepam</a></li> <li><a href="/wiki/Dimdazenil" title="Dimdazenil">Dimdazenil</a></li> <li><a href="/wiki/Doxefazepam" title="Doxefazepam">Doxefazepam</a></li> <li><a href="/wiki/Elfazepam" title="Elfazepam">Elfazepam</a></li> <li><a href="/wiki/Estazolam" title="Estazolam">Estazolam</a></li> <li><a href="/wiki/Ethyl_carfluzepate" title="Ethyl carfluzepate">Ethyl carfluzepate</a></li> <li><a href="/wiki/Ethyl_dirazepate" title="Ethyl dirazepate">Ethyl dirazepate</a></li> <li><a href="/wiki/Ethyl_loflazepate" title="Ethyl loflazepate">Ethyl loflazepate</a></li> <li><a href="/wiki/Etizolam" title="Etizolam">Etizolam</a></li> <li><a href="/wiki/FG-8205" title="FG-8205">FG-8205</a></li> <li><a href="/wiki/Fletazepam" title="Fletazepam">Fletazepam</a></li> <li><a href="/wiki/Flubromazepam" title="Flubromazepam">Flubromazepam</a></li> <li><a href="/wiki/Flubromazolam" title="Flubromazolam">Flubromazolam</a></li> <li><a href="/wiki/Fludiazepam" title="Fludiazepam">Fludiazepam</a></li> <li><a href="/wiki/Flunitrazepam" title="Flunitrazepam">Flunitrazepam</a></li> <li><a href="/wiki/Flunitrazolam" title="Flunitrazolam">Flunitrazolam</a></li> <li><a href="/wiki/Flurazepam" title="Flurazepam">Flurazepam</a></li> <li><a href="/wiki/Flutazolam" title="Flutazolam">Flutazolam</a></li> <li><a href="/wiki/Flutemazepam" title="Flutemazepam">Flutemazepam</a></li> <li><a href="/wiki/Flutoprazepam" title="Flutoprazepam">Flutoprazepam</a></li> <li><a href="/wiki/Fosazepam" title="Fosazepam">Fosazepam</a></li> <li><a href="/wiki/Gidazepam" title="Gidazepam">Gidazepam</a></li> <li><a href="/wiki/Halazepam" title="Halazepam">Halazepam</a></li> <li><a href="/wiki/Haloxazolam" title="Haloxazolam">Haloxazolam</a></li> <li><a href="/wiki/Iclazepam" title="Iclazepam">Iclazepam</a></li> <li><a href="/wiki/Imidazenil" title="Imidazenil">Imidazenil</a></li> <li><a href="/wiki/Irazepine" title="Irazepine">Irazepine</a></li> <li><a href="/wiki/Ketazolam" title="Ketazolam">Ketazolam</a></li> <li><a href="/wiki/Lofendazam" title="Lofendazam">Lofendazam</a></li> <li><a href="/wiki/Lopirazepam" title="Lopirazepam">Lopirazepam</a></li> <li><a href="/wiki/Loprazolam" title="Loprazolam">Loprazolam</a></li> <li><a href="/wiki/Lorazepam" title="Lorazepam">Lorazepam</a></li> <li><a href="/wiki/Lormetazepam" title="Lormetazepam">Lormetazepam</a></li> <li><a href="/wiki/Meclonazepam" title="Meclonazepam">Meclonazepam</a></li> <li><a href="/wiki/Medazepam" title="Medazepam">Medazepam</a></li> <li><a href="/wiki/Menitrazepam" title="Menitrazepam">Menitrazepam</a></li> <li><a href="/wiki/Metaclazepam" title="Metaclazepam">Metaclazepam</a></li> <li><a href="/wiki/Mexazolam" title="Mexazolam">Mexazolam</a></li> <li><a href="/wiki/Midazolam" title="Midazolam">Midazolam</a></li> <li><a href="/wiki/Motrazepam" title="Motrazepam">Motrazepam</a></li> <li><a href="/wiki/N-Desalkylflurazepam" title="N-Desalkylflurazepam">N-Desalkylflurazepam</a></li> <li><a href="/wiki/Nifoxipam" title="Nifoxipam">Nifoxipam</a></li> <li><a href="/wiki/Nimetazepam" title="Nimetazepam">Nimetazepam</a></li> <li><a href="/wiki/Nitrazepam" title="Nitrazepam">Nitrazepam</a></li> <li><a href="/wiki/Nitrazepate" title="Nitrazepate">Nitrazepate</a></li> <li><a href="/wiki/Nitrazolam" title="Nitrazolam">Nitrazolam</a></li> <li><a href="/wiki/Nordazepam" title="Nordazepam">Nordazepam</a></li> <li><a href="/wiki/Nortetrazepam" title="Nortetrazepam">Nortetrazepam</a></li> <li><a href="/wiki/Oxazepam" title="Oxazepam">Oxazepam</a></li> <li><a href="/wiki/Oxazolam" title="Oxazolam">Oxazolam</a></li> <li><a href="/wiki/Phenazepam" title="Phenazepam">Phenazepam</a></li> <li><a href="/wiki/Pinazepam" title="Pinazepam">Pinazepam</a></li> <li><a href="/wiki/Pivoxazepam" title="Pivoxazepam">Pivoxazepam</a></li> <li><a href="/wiki/Prazepam" title="Prazepam">Prazepam</a></li> <li><a href="/wiki/Premazepam" title="Premazepam">Premazepam</a></li> <li><a href="/wiki/Proflazepam" title="Proflazepam">Proflazepam</a></li> <li><a href="/wiki/Pyrazolam" title="Pyrazolam">Pyrazolam</a></li> <li><a href="/wiki/QH-II-66" title="QH-II-66">QH-II-66</a></li> <li><a href="/wiki/Quazepam" title="Quazepam">Quazepam</a></li> <li><a href="/wiki/Reclazepam" title="Reclazepam">Reclazepam</a></li> <li><a href="/wiki/Remimazolam" title="Remimazolam">Remimazolam</a></li> <li><a href="/wiki/Rilmazafone" title="Rilmazafone">Rilmazafone</a></li> <li><a href="/wiki/Ripazepam" title="Ripazepam">Ripazepam</a></li> <li><a href="/wiki/Ro48-6791" title="Ro48-6791">Ro48-6791</a></li> <li><a href="/wiki/Ro48-8684" title="Ro48-8684">Ro48-8684</a></li> <li><a href="/wiki/SH-053-R-CH3-2%E2%80%B2F" title="SH-053-R-CH3-2′F">SH-053-R-CH3-2′F</a></li> <li><a href="/wiki/Sulazepam" title="Sulazepam">Sulazepam</a></li> <li><a href="/wiki/Temazepam" title="Temazepam">Temazepam</a></li> <li><a href="/wiki/Tetrazepam" title="Tetrazepam">Tetrazepam</a></li> <li><a href="/wiki/Tolufazepam" class="mw-redirect" title="Tolufazepam">Tolufazepam</a></li> <li><a href="/wiki/Triazolam" title="Triazolam">Triazolam</a></li> <li><a href="/wiki/Triflubazam" title="Triflubazam">Triflubazam</a></li> <li><a href="/wiki/Triflunordazepam" title="Triflunordazepam">Triflunordazepam (Ro5-2904)</a></li> <li><a href="/wiki/Tuclazepam" title="Tuclazepam">Tuclazepam</a></li> <li><a href="/wiki/Uldazepam" title="Uldazepam">Uldazepam</a></li> <li><a href="/wiki/Zapizolam" title="Zapizolam">Zapizolam</a></li> <li><a href="/wiki/Zolazepam" title="Zolazepam">Zolazepam</a></li> <li><a href="/wiki/Zomebazam" title="Zomebazam">Zomebazam</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Carbamate" title="Carbamate">Carbamates</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/Carisbamate" title="Carisbamate">Carisbamate</a></li> <li><a href="/wiki/Carisoprodol" title="Carisoprodol">Carisoprodol</a></li> <li><a href="/wiki/Clocental" title="Clocental">Clocental</a></li> <li><a href="/wiki/Cyclarbamate" title="Cyclarbamate">Cyclarbamate</a></li> <li><a href="/wiki/Difebarbamate" title="Difebarbamate">Difebarbamate</a></li> <li><a href="/wiki/Emylcamate" title="Emylcamate">Emylcamate</a></li> <li><a href="/wiki/Ethinamate" title="Ethinamate">Ethinamate</a></li> <li><a href="/wiki/Febarbamate" title="Febarbamate">Febarbamate</a></li> <li><a href="/wiki/Felbamate" title="Felbamate">Felbamate</a></li> <li><a href="/wiki/Hexapropymate" title="Hexapropymate">Hexapropymate</a></li> <li><a href="/wiki/Hydroxyphenamate" title="Hydroxyphenamate">Hydroxyphenamate</a></li> <li><a href="/wiki/Lorbamate" title="Lorbamate">Lorbamate</a></li> <li><a href="/wiki/Mebutamate" title="Mebutamate">Mebutamate</a></li> <li><a href="/wiki/Meprobamate" title="Meprobamate">Meprobamate</a></li> <li><a href="/wiki/Nisobamate" title="Nisobamate">Nisobamate</a></li> <li><a href="/wiki/Pentabamate" title="Pentabamate">Pentabamate</a></li> <li><a href="/wiki/Phenprobamate" title="Phenprobamate">Phenprobamate</a></li> <li><a href="/wiki/Procymate" title="Procymate">Procymate</a></li> <li><a href="/wiki/Styramate" title="Styramate">Styramate</a></li> <li><a href="/wiki/Tetrabamate" title="Tetrabamate">Tetrabamate</a></li> <li><a href="/wiki/Tybamate" title="Tybamate">Tybamate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Flavonoid" title="Flavonoid">Flavonoids</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/6-Methylapigenin" title="6-Methylapigenin">6-Methylapigenin</a></li> <li><a href="/wiki/Ampelopsin" title="Ampelopsin">Ampelopsin (dihydromyricetin)</a></li> <li><a href="/wiki/Apigenin" title="Apigenin">Apigenin</a></li> <li><a href="/wiki/Baicalein" title="Baicalein">Baicalein</a></li> <li><a href="/wiki/Baicalin" title="Baicalin">Baicalin</a></li> <li><a href="/wiki/Catechin" title="Catechin">Catechin</a></li> <li><a href="/wiki/Epigallocatechin" class="mw-redirect" title="Epigallocatechin">EGC</a></li> <li><a href="/wiki/Epigallocatechin_gallate" title="Epigallocatechin gallate">EGCG</a></li> <li><a href="/wiki/Hispidulin" title="Hispidulin">Hispidulin</a></li> <li><a href="/w/index.php?title=Linarin&action=edit&redlink=1" class="new" title="Linarin (page does not exist)">Linarin</a></li> <li><a href="/wiki/Luteolin" title="Luteolin">Luteolin</a></li> <li><a href="/w/index.php?title=Trans-6,4%E2%80%B2-dimethoxyretrochalcone&action=edit&redlink=1" class="new" title="Trans-6,4′-dimethoxyretrochalcone (page does not exist)">Rc-OMe</a></li> <li><a href="/wiki/Scutellaria" title="Scutellaria">Skullcap</a> constituents (e.g., <a href="/wiki/Baicalin" title="Baicalin">baicalin</a>)</li> <li><a href="/wiki/Wogonin" title="Wogonin">Wogonin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Imidazole" title="Imidazole">Imidazoles</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/Etomidate" title="Etomidate">Etomidate</a></li> <li><a href="/wiki/Metomidate" title="Metomidate">Metomidate</a></li> <li><a href="/wiki/Propoxate" title="Propoxate">Propoxate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Kava" title="Kava">Kava</a> constituents</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="/w/index.php?title=10-Methoxyyangonin&action=edit&redlink=1" class="new" title="10-Methoxyyangonin (page does not exist)">10-Methoxyyangonin</a></li> <li><a href="/w/index.php?title=11-Methoxyyangonin&action=edit&redlink=1" class="new" title="11-Methoxyyangonin (page does not exist)">11-Methoxyyangonin</a></li> <li><a href="/w/index.php?title=11-Hydroxyyangonin&action=edit&redlink=1" class="new" title="11-Hydroxyyangonin (page does not exist)">11-Hydroxyyangonin</a></li> <li><a href="/wiki/Desmethoxyyangonin" title="Desmethoxyyangonin">Desmethoxyyangonin</a></li> <li><a href="/w/index.php?title=11-Methoxy-12-hydroxydehydrokavain&action=edit&redlink=1" class="new" title="11-Methoxy-12-hydroxydehydrokavain (page does not exist)">11-Methoxy-12-hydroxydehydrokavain</a></li> <li><a href="/w/index.php?title=7,8-Dihydroyangonin&action=edit&redlink=1" class="new" title="7,8-Dihydroyangonin (page does not exist)">7,8-Dihydroyangonin</a></li> <li><a href="/wiki/Kavain" title="Kavain">Kavain</a></li> <li><a href="/w/index.php?title=5-Hydroxykavain&action=edit&redlink=1" class="new" title="5-Hydroxykavain (page does not exist)">5-Hydroxykavain</a></li> <li><a href="/w/index.php?title=5,6-Dihydroyangonin&action=edit&redlink=1" class="new" title="5,6-Dihydroyangonin (page does not exist)">5,6-Dihydroyangonin</a></li> <li><a href="/w/index.php?title=7,8-Dihydrokavain&action=edit&redlink=1" class="new" title="7,8-Dihydrokavain (page does not exist)">7,8-Dihydrokavain</a></li> <li><a href="/w/index.php?title=5,6,7,8-Tetrahydroyangonin&action=edit&redlink=1" class="new" title="5,6,7,8-Tetrahydroyangonin (page does not exist)">5,6,7,8-Tetrahydroyangonin</a></li> <li><a href="/w/index.php?title=5,6-Dehydromethysticin&action=edit&redlink=1" class="new" title="5,6-Dehydromethysticin (page does not exist)">5,6-Dehydromethysticin</a></li> <li><a href="/wiki/Methysticin" title="Methysticin">Methysticin</a></li> <li><a href="/w/index.php?title=7,8-Dihydromethysticin&action=edit&redlink=1" class="new" title="7,8-Dihydromethysticin (page does not exist)">7,8-Dihydromethysticin</a></li> <li><a href="/wiki/Yangonin" title="Yangonin">Yangonin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Monoureide" class="mw-redirect" title="Monoureide">Monoureides</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/Acecarbromal" title="Acecarbromal">Acecarbromal</a></li> <li><a href="/wiki/Apronal" title="Apronal">Apronal (apronalide)</a></li> <li><a href="/wiki/Bromisoval" title="Bromisoval">Bromisoval</a></li> <li><a href="/wiki/Carbromal" title="Carbromal">Carbromal</a></li> <li><a href="/w/index.php?title=Capuride&action=edit&redlink=1" class="new" title="Capuride (page does not exist)">Capuride</a></li> <li><a href="/w/index.php?title=Ectylurea&action=edit&redlink=1" class="new" title="Ectylurea (page does not exist)">Ectylurea</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Neuroactive_steroid" class="mw-redirect" title="Neuroactive steroid">Neuroactive 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"> <ul><li><a href="/wiki/Acebrochol" title="Acebrochol">Acebrochol</a></li> <li><a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone (brexanolone)</a></li> <li><a href="/wiki/Alfadolone" title="Alfadolone">Alfadolone</a></li> <li><a href="/wiki/Alfaxalone" title="Alfaxalone">Alfaxalone</a></li> <li><a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/wiki/Androstenol" title="Androstenol">Androstenol</a></li> <li><a href="/wiki/Androsterone" title="Androsterone">Androsterone</a></li> <li>Certain <a href="/wiki/Anabolic-androgenic_steroid" class="mw-redirect" title="Anabolic-androgenic steroid">anabolic-androgenic steroids</a></li> <li><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></li> <li><a href="/wiki/Dihydrodeoxycorticosterone" title="Dihydrodeoxycorticosterone">DHDOC</a></li> <li><a href="/wiki/3%CE%B1-Dihydroprogesterone" title="3α-Dihydroprogesterone">3α-DHP</a></li> <li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">5α-DHP</a></li> <li><a href="/wiki/5%CE%B2-Dihydroprogesterone" title="5β-Dihydroprogesterone">5β-DHP</a></li> <li><a href="/wiki/Dihydrotestosterone" title="Dihydrotestosterone">DHT</a></li> <li><a href="/wiki/Etiocholanolone" title="Etiocholanolone">Etiocholanolone</a></li> <li><a href="/wiki/Ganaxolone" title="Ganaxolone">Ganaxolone</a></li> <li><a href="/wiki/Hydroxydione" title="Hydroxydione">Hydroxydione</a></li> <li><a href="/wiki/Minaxolone" title="Minaxolone">Minaxolone</a></li> <li><a href="/wiki/ORG-20599" title="ORG-20599">ORG-20599</a></li> <li><a href="/wiki/ORG-21465" title="ORG-21465">ORG-21465</a></li> <li><a href="/wiki/P1-185" title="P1-185">P1-185</a></li> <li><a href="/wiki/Posovolone" title="Posovolone">Posovolone</a></li> <li><a href="/wiki/Pregnanolone" title="Pregnanolone">Pregnanolone (eltanolone)</a></li> <li><a class="mw-selflink selflink">Progesterone</a></li> <li><a href="/wiki/Renanolone" title="Renanolone">Renanolone</a></li> <li><a href="/w/index.php?title=SAGE-105&action=edit&redlink=1" class="new" title="SAGE-105 (page does not exist)">SAGE-105</a></li> <li><a href="/wiki/SAGE-324" title="SAGE-324">SAGE-324</a></li> <li><a href="/w/index.php?title=SAGE-516&action=edit&redlink=1" class="new" title="SAGE-516 (page does not exist)">SAGE-516</a></li> <li><a href="/w/index.php?title=SAGE-689&action=edit&redlink=1" class="new" title="SAGE-689 (page does not exist)">SAGE-689</a></li> <li><a href="/w/index.php?title=SAGE-872&action=edit&redlink=1" class="new" title="SAGE-872 (page does not exist)">SAGE-872</a></li> <li><a href="/wiki/Testosterone" title="Testosterone">Testosterone</a></li> <li><a href="/wiki/Tetrahydrodeoxycorticosterone" title="Tetrahydrodeoxycorticosterone">THDOC</a></li> <li><a href="/wiki/Zuranolone" title="Zuranolone">Zuranolone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Nonbenzodiazepine" title="Nonbenzodiazepine">Nonbenzodiazepines</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/Cyclopyrrolone" class="mw-redirect" title="Cyclopyrrolone">Cyclopyrrolones</a>: <a href="/wiki/Eszopiclone" title="Eszopiclone">Eszopiclone</a></li> <li><a href="/wiki/Pagoclone" title="Pagoclone">Pagoclone</a></li> <li><a href="/wiki/Pazinaclone" title="Pazinaclone">Pazinaclone</a></li> <li><a href="/wiki/Suproclone" title="Suproclone">Suproclone</a></li> <li><a href="/wiki/Suriclone" title="Suriclone">Suriclone</a></li> <li><a href="/wiki/Zopiclone" title="Zopiclone">Zopiclone</a></li></ul> <ul><li><a href="/wiki/Imidazopyridine" title="Imidazopyridine">Imidazopyridines</a>: <a href="/wiki/Alpidem" title="Alpidem">Alpidem</a></li> <li><a href="/wiki/DS-1_(drug)" title="DS-1 (drug)">DS-1</a></li> <li><a href="/wiki/Necopidem" title="Necopidem">Necopidem</a></li> <li><a href="/wiki/Saripidem" title="Saripidem">Saripidem</a></li> <li><a href="/wiki/Zolpidem" title="Zolpidem">Zolpidem</a></li></ul> <ul><li><a href="/wiki/Pyrazolopyrimidine" title="Pyrazolopyrimidine">Pyrazolopyrimidines</a>: <a href="/wiki/Divaplon" title="Divaplon">Divaplon</a></li> <li><a href="/wiki/Fasiplon" title="Fasiplon">Fasiplon</a></li> <li><a href="/wiki/Indiplon" title="Indiplon">Indiplon</a></li> <li><a href="/wiki/Lorediplon" title="Lorediplon">Lorediplon</a></li> <li><a href="/wiki/Ocinaplon" title="Ocinaplon">Ocinaplon</a></li> <li><a href="/wiki/Panadiplon" title="Panadiplon">Panadiplon</a></li> <li><a href="/wiki/Taniplon" title="Taniplon">Taniplon</a></li> <li><a href="/wiki/Zaleplon" title="Zaleplon">Zaleplon</a></li></ul> <ul><li>Others: <a href="/wiki/Adipiplon" title="Adipiplon">Adipiplon</a></li> <li><a href="/wiki/CGS-8216" title="CGS-8216">CGS-8216</a></li> <li><a href="/wiki/CGS-9896" title="CGS-9896">CGS-9896</a></li> <li><a href="/wiki/CGS-13767" title="CGS-13767">CGS-13767</a></li> <li><a href="/wiki/CGS-20625" title="CGS-20625">CGS-20625</a></li> <li><a href="/wiki/CL-218,872" title="CL-218,872">CL-218,872</a></li> <li><a href="/wiki/CP-615,003" title="CP-615,003">CP-615,003</a></li> <li><a href="/w/index.php?title=CTP-354&action=edit&redlink=1" class="new" title="CTP-354 (page does not exist)">CTP-354</a></li> <li><a href="/wiki/ELB-139" title="ELB-139">ELB-139</a></li> <li><a href="/wiki/GBLD-345" title="GBLD-345">GBLD-345</a></li> <li><a href="/wiki/Imepitoin" title="Imepitoin">Imepitoin</a></li> <li><a href="/wiki/JM-1232" title="JM-1232">JM-1232</a></li> <li><a href="/wiki/L-838,417" title="L-838,417">L-838,417</a></li> <li><a href="/wiki/Lirequinil" title="Lirequinil">Lirequinil (Ro41-3696)</a></li> <li><a href="/wiki/NS-2664" title="NS-2664">NS-2664</a></li> <li><a href="/wiki/NS-2710" title="NS-2710">NS-2710</a></li> <li><a href="/wiki/NS-11394" title="NS-11394">NS-11394</a></li> <li><a href="/wiki/Pipequaline" title="Pipequaline">Pipequaline</a></li> <li><a href="/wiki/ROD-188" title="ROD-188">ROD-188</a></li> <li><a href="/wiki/RWJ-51204" title="RWJ-51204">RWJ-51204</a></li> <li><a href="/wiki/SB-205,384" class="mw-redirect" title="SB-205,384">SB-205,384</a></li> <li><a href="/wiki/SX-3228" title="SX-3228">SX-3228</a></li> <li><a href="/w/index.php?title=TGSC01AA&action=edit&redlink=1" class="new" title="TGSC01AA (page does not exist)">TGSC01AA</a></li> <li><a href="/wiki/TP-003" title="TP-003">TP-003</a></li> <li><a href="/wiki/TPA-023" title="TPA-023">TPA-023</a></li> <li><a href="/wiki/TP-13" title="TP-13">TP-13</a></li> <li><a href="/wiki/U-89843A" title="U-89843A">U-89843A</a></li> <li><a href="/wiki/U-90042" title="U-90042">U-90042</a></li> <li><a href="/wiki/Viqualine" title="Viqualine">Viqualine</a></li> <li><a href="/wiki/Y-23684" title="Y-23684">Y-23684</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Phenol" title="Phenol">Phenols</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/Fospropofol" title="Fospropofol">Fospropofol</a></li> <li><a href="/wiki/Propofol" title="Propofol">Propofol</a></li> <li><a href="/wiki/Thymol" title="Thymol">Thymol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Piperidinedione" class="mw-redirect" title="Piperidinedione">Piperidinediones</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/Glutethimide" title="Glutethimide">Glutethimide</a></li> <li><a href="/wiki/Methyprylon" title="Methyprylon">Methyprylon</a></li> <li><a href="/wiki/Piperidione" title="Piperidione">Piperidione</a></li> <li><a href="/wiki/Pyrithyldione" title="Pyrithyldione">Pyrithyldione</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Pyrazolopyridine" class="mw-redirect" title="Pyrazolopyridine">Pyrazolopyridines</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/Cartazolate" title="Cartazolate">Cartazolate</a></li> <li><a href="/wiki/Etazolate" title="Etazolate">Etazolate</a></li> <li><a href="/wiki/ICI-190,622" title="ICI-190,622">ICI-190,622</a></li> <li><a href="/wiki/Tracazolate" title="Tracazolate">Tracazolate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Quinazolinone" title="Quinazolinone">Quinazolinones</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/Afloqualone" title="Afloqualone">Afloqualone</a></li> <li><a href="/wiki/Cloroqualone" title="Cloroqualone">Cloroqualone</a></li> <li><a href="/wiki/Diproqualone" title="Diproqualone">Diproqualone</a></li> <li><a href="/wiki/Etaqualone" title="Etaqualone">Etaqualone</a></li> <li><a href="/wiki/Mebroqualone" title="Mebroqualone">Mebroqualone</a></li> <li><a href="/wiki/Mecloqualone" title="Mecloqualone">Mecloqualone</a></li> <li><a href="/wiki/Methaqualone" title="Methaqualone">Methaqualone</a></li> <li><a href="/wiki/Methylmethaqualone" title="Methylmethaqualone">Methylmethaqualone</a></li> <li><a href="/wiki/Nitromethaqualone" title="Nitromethaqualone">Nitromethaqualone</a></li> <li><a href="/wiki/SL-164" title="SL-164">SL-164</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Inhalational_anaesthetic" class="mw-redirect" title="Inhalational anaesthetic">Volatiles</a>/<a href="/wiki/Inhalational_anaesthetic" class="mw-redirect" title="Inhalational anaesthetic">gases</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/Acetone" title="Acetone">Acetone</a></li> <li><a href="/wiki/Acetophenone" title="Acetophenone">Acetophenone</a></li> <li><a href="/wiki/Acetylglycinamide_chloral_hydrate" title="Acetylglycinamide chloral hydrate">Acetylglycinamide chloral hydrate</a></li> <li><a href="/wiki/Aliflurane" title="Aliflurane">Aliflurane</a></li> <li><a href="/wiki/Benzene" title="Benzene">Benzene</a></li> <li><a href="/wiki/Butane" title="Butane">Butane</a></li> <li><a href="/wiki/Butylene" class="mw-redirect" title="Butylene">Butylene</a></li> <li><a href="/wiki/Centalun" title="Centalun">Centalun</a></li> <li><a href="/wiki/Chloral" title="Chloral">Chloral</a></li> <li><a href="/wiki/Chloral_betaine" title="Chloral betaine">Chloral betaine</a></li> <li><a href="/wiki/Chloral_hydrate" title="Chloral hydrate">Chloral hydrate</a></li> <li><a href="/wiki/Chloroform" title="Chloroform">Chloroform</a></li> <li><a href="/wiki/Cryofluorane" class="mw-redirect" title="Cryofluorane">Cryofluorane</a></li> <li><a href="/wiki/Desflurane" title="Desflurane">Desflurane</a></li> <li><a href="/wiki/Dichloralphenazone" title="Dichloralphenazone">Dichloralphenazone</a></li> <li><a href="/wiki/Dichloromethane" title="Dichloromethane">Dichloromethane</a></li> <li><a href="/wiki/Diethyl_ether" title="Diethyl ether">Diethyl ether</a></li> <li><a href="/wiki/Enflurane" title="Enflurane">Enflurane</a></li> <li><a href="/wiki/Chloroethane" title="Chloroethane">Ethyl chloride</a></li> <li><a href="/wiki/Ethylene" title="Ethylene">Ethylene</a></li> <li><a href="/wiki/Fluroxene" title="Fluroxene">Fluroxene</a></li> <li><a href="/wiki/Gasoline" title="Gasoline">Gasoline</a></li> <li><a href="/wiki/Halopropane" title="Halopropane">Halopropane</a></li> <li><a href="/wiki/Halothane" title="Halothane">Halothane</a></li> <li><a href="/wiki/Isoflurane" title="Isoflurane">Isoflurane</a></li> <li><a href="/wiki/Kerosene" title="Kerosene">Kerosine</a></li> <li><a href="/wiki/Methoxyflurane" title="Methoxyflurane">Methoxyflurane</a></li> <li><a href="/wiki/Methoxypropane" title="Methoxypropane">Methoxypropane</a></li> <li><a href="/wiki/Nitric_oxide" title="Nitric oxide">Nitric oxide</a></li> <li><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li> <li><a href="/wiki/Norflurane" class="mw-redirect" title="Norflurane">Norflurane</a></li> <li><a href="/wiki/Paraldehyde" title="Paraldehyde">Paraldehyde</a></li> <li><a href="/wiki/Propane" title="Propane">Propane</a></li> <li><a href="/wiki/Propene" class="mw-redirect" title="Propene">Propylene</a></li> <li><a href="/wiki/Roflurane" title="Roflurane">Roflurane</a></li> <li><a href="/wiki/Sevoflurane" title="Sevoflurane">Sevoflurane</a></li> <li><a href="/wiki/Synthane" title="Synthane">Synthane</a></li> <li><a href="/wiki/Teflurane" title="Teflurane">Teflurane</a></li> <li><a href="/wiki/Toluene" title="Toluene">Toluene</a></li> <li><a href="/wiki/1,1,1-Trichloroethane" title="1,1,1-Trichloroethane">Trichloroethane (methyl chloroform)</a></li> <li><a href="/wiki/Trichloroethylene" title="Trichloroethylene">Trichloroethylene</a></li> <li><a href="/wiki/Divinyl_ether" title="Divinyl ether">Vinyl ether</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;">Others/unsorted</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/3-Hydroxybutanal" title="3-Hydroxybutanal">3-Hydroxybutanal</a></li> <li><a href="/w/index.php?title=%CE%91-Ethyl-%CE%B1-methylthiobutyrolactone&action=edit&redlink=1" class="new" title="Α-Ethyl-α-methylthiobutyrolactone (page does not exist)">α-EMTBL</a></li> <li><a href="/w/index.php?title=AA-29504&action=edit&redlink=1" class="new" title="AA-29504 (page does not exist)">AA-29504</a></li> <li><a href="/wiki/Alogabat" title="Alogabat">Alogabat</a></li> <li><a href="/wiki/Avermectin" title="Avermectin">Avermectins</a> (e.g., <a href="/wiki/Ivermectin" title="Ivermectin">ivermectin</a>)</li> <li><a href="/wiki/Bromide" title="Bromide">Bromide</a> compounds (e.g., <a href="/wiki/Lithium_bromide" title="Lithium bromide">lithium bromide</a>, <a href="/wiki/Potassium_bromide" title="Potassium bromide">potassium bromide</a>, <a href="/wiki/Sodium_bromide" title="Sodium bromide">sodium bromide</a>)</li> <li><a href="/wiki/Carbamazepine" title="Carbamazepine">Carbamazepine</a></li> <li><a href="/wiki/Chloralose" title="Chloralose">Chloralose</a></li> <li><a href="/wiki/Chlormezanone" title="Chlormezanone">Chlormezanone</a></li> <li><a href="/wiki/Clomethiazole" title="Clomethiazole">Clomethiazole</a></li> <li><a href="/wiki/Darigabat" title="Darigabat">Darigabat</a></li> <li><a href="/wiki/3,3-Diethyl-2-pyrrolidinone" title="3,3-Diethyl-2-pyrrolidinone">DEABL</a></li> <li><a href="/wiki/Deuterated_etifoxine" title="Deuterated etifoxine">Deuterated etifoxine</a></li> <li><a href="/wiki/Dihydroergoline" class="mw-redirect" title="Dihydroergoline">Dihydroergolines</a> (e.g., <a href="/wiki/Dihydroergocryptine" title="Dihydroergocryptine">dihydroergocryptine</a>, <a href="/w/index.php?title=Dihydroergosine&action=edit&redlink=1" class="new" title="Dihydroergosine (page does not exist)">dihydroergosine</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Ergoloid" title="Ergoloid">ergoloid (dihydroergotoxine)</a>)</li> <li><a href="/w/index.php?title=4-Chloro-N-(2-(2-thienyl)imidazo(1,2-a)pyridin-3-yl)benzamide&action=edit&redlink=1" class="new" title="4-Chloro-N-(2-(2-thienyl)imidazo(1,2-a)pyridin-3-yl)benzamide (page does not exist)">DS2</a></li> <li><a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Etazepine" title="Etazepine">Etazepine</a></li> <li><a href="/wiki/Etifoxine" title="Etifoxine">Etifoxine</a></li> <li><a href="/wiki/Fenamate" class="mw-redirect" title="Fenamate">Fenamates</a> (e.g., <a href="/wiki/Flufenamic_acid" title="Flufenamic acid">flufenamic acid</a>, <a href="/wiki/Mefenamic_acid" title="Mefenamic acid">mefenamic acid</a>, <a href="/wiki/Niflumic_acid" title="Niflumic acid">niflumic acid</a>, <a href="/wiki/Tolfenamic_acid" title="Tolfenamic acid">tolfenamic acid</a>)</li> <li><a href="/wiki/Fluoxetine" title="Fluoxetine">Fluoxetine</a></li> <li><a href="/wiki/Flupirtine" title="Flupirtine">Flupirtine</a></li> <li><a href="/wiki/Hopantenic_acid" title="Hopantenic acid">Hopantenic acid</a></li> <li><a href="/wiki/KRM-II-81" title="KRM-II-81">KRM-II-81</a></li> <li><a href="/wiki/Lanthanum" title="Lanthanum">Lanthanum</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/4-O-methylhonokiol" class="mw-redirect" title="4-O-methylhonokiol">4-O-methylhonokiol</a>, <a href="/wiki/Honokiol" title="Honokiol">honokiol</a>, <a href="/wiki/Magnolol" title="Magnolol">magnolol</a>, <a href="/wiki/Obovatol" title="Obovatol">obovatol</a>)</li> <li><a href="/wiki/Loreclezole" title="Loreclezole">Loreclezole</a></li> <li><a href="/wiki/Menthyl_isovalerate" title="Menthyl isovalerate">Menthyl isovalerate (validolum)</a></li> <li><a href="/wiki/Monastrol" title="Monastrol">Monastrol</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/Org_25435" class="mw-redirect" title="Org 25435">Org 25,435</a></li> <li><a href="/wiki/Phenytoin" title="Phenytoin">Phenytoin</a></li> <li><a href="/wiki/Propanidid" title="Propanidid">Propanidid</a></li> <li><a href="/wiki/Retigabine" title="Retigabine">Retigabine (ezogabine)</a></li> <li><a href="/wiki/Safranal" title="Safranal">Safranal</a></li> <li><a href="/wiki/Seproxetine" title="Seproxetine">Seproxetine</a></li> <li><a href="/wiki/Stiripentol" title="Stiripentol">Stiripentol</a></li> <li><a href="/w/index.php?title=Sulfonylalkane&action=edit&redlink=1" class="new" title="Sulfonylalkane (page does not exist)">Sulfonylalkanes</a> (e.g., <a href="/wiki/Sulfonmethane" title="Sulfonmethane">sulfonmethane (sulfonal)</a>, <a href="/wiki/Tetronal" title="Tetronal">tetronal</a>, <a href="/wiki/Trional" title="Trional">trional</a>)</li> <li><a href="/wiki/Terpenoid" title="Terpenoid">Terpenoids</a> (e.g., <a href="/wiki/Borneol" title="Borneol">borneol</a>)</li> <li><a href="/wiki/Topiramate" title="Topiramate">Topiramate</a></li> <li><a href="/wiki/Valerian_(herb)" title="Valerian (herb)">Valerian</a> constituents (e.g., <a href="/wiki/3-methylbutanoic_acid" class="mw-redirect" title="3-methylbutanoic acid">isovaleric acid</a>, <a href="/wiki/Isovaleramide" title="Isovaleramide">isovaleramide</a>, <a href="/wiki/Valerenic_acid" title="Valerenic acid">valerenic acid</a>, <a href="/w/index.php?title=Valerenol&action=edit&redlink=1" class="new" title="Valerenol (page does not exist)">valerenol</a>)</li></ul> <ul><li>Unsorted benzodiazepine site positive modulators: <a href="/wiki/%CE%91-Pinene" title="Α-Pinene">α-Pinene</a></li> <li><a href="/wiki/MRK-409_(MK-0343)" class="mw-redirect" title="MRK-409 (MK-0343)">MRK-409 (MK-0343)</a></li> <li><a href="/w/index.php?title=TCS-1105&action=edit&redlink=1" class="new" title="TCS-1105 (page does not exist)">TCS-1105</a></li> <li><a href="/wiki/TCS-1205" title="TCS-1205">TCS-1205</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div>See also: <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a> • <a href="/wiki/Template:GABA_receptor_modulators" title="Template:GABA receptor modulators">GABA receptor modulators</a> • <a href="/wiki/Template:GABA_metabolism_and_transport_modulators" title="Template:GABA metabolism and transport modulators">GABA metabolism/transport modulators</a></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="Glucocorticoid_receptor_modulators752" 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:Glucocorticoid_receptor_modulators" title="Template:Glucocorticoid receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Glucocorticoid_receptor_modulators" title="Template talk:Glucocorticoid receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Glucocorticoid_receptor_modulators" title="Special:EditPage/Template:Glucocorticoid receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Glucocorticoid_receptor_modulators752" style="font-size:114%;margin:0 4em"><a href="/wiki/Glucocorticoid_receptor" title="Glucocorticoid receptor">Glucocorticoid 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/Glucocorticoid_receptor" title="Glucocorticoid receptor"><abbr title="Glucocorticoid receptor">GR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Glucocorticoid receptor</th><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"><a href="/wiki/Glucocorticoid" title="Glucocorticoid">Agonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Cortisol-like and related (16-unsubstituted): <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/9%CE%B1-Fluorocortisone" title="9α-Fluorocortisone">9α-Fluorocortisone (alfluorone)</a></li> <li><a href="/wiki/11-Dehydrocorticosterone" title="11-Dehydrocorticosterone">11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone)</a> <ul><li><a href="/w/index.php?title=11-Dehydrocorticosterone_acetate&action=edit&redlink=1" class="new" title="11-Dehydrocorticosterone acetate (page does not exist)">11-Dehydrocorticosterone acetate</a></li></ul></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone (desoxycortone, deoxycortone, desoxycorticosterone)</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Desoxycortone_esters" title="List of corticosteroid esters">Desoxycortone esters</a></li></ul></li> <li><a href="/wiki/11-Deoxycortisol" title="11-Deoxycortisol">11-Deoxycortisol (cortodoxone, cortexolone)</a> <ul><li><a href="/wiki/Cortifen" title="Cortifen">Cortifen (cortiphen, kortifen)</a></li> <li><a href="/w/index.php?title=Cortodoxone_acetate&action=edit&redlink=1" class="new" title="Cortodoxone acetate (page does not exist)">Cortodoxone acetate</a></li></ul></li> <li><a href="/wiki/21-Deoxycortisol" title="21-Deoxycortisol">21-Deoxycortisol</a></li> <li><a href="/wiki/%CE%947-Prednisolone" title="Δ7-Prednisolone">Δ7-Prednisolone</a> <ul><li><a href="/w/index.php?title=%CE%947-Prednisolone_21-acetate&action=edit&redlink=1" class="new" title="Δ7-Prednisolone 21-acetate (page does not exist)">Δ7-Prednisolone 21-acetate</a></li></ul></li> <li><a href="/wiki/Amebucort" title="Amebucort">Amebucort</a></li> <li><a href="/wiki/Chloroprednisone" title="Chloroprednisone">Chloroprednisone</a> <ul><li><a href="/wiki/Chloroprednisone_acetate" title="Chloroprednisone acetate">Chloroprednisone acetate</a></li></ul></li> <li><a href="/wiki/Cloprednol" title="Cloprednol">Cloprednol</a> <ul><li><a href="/w/index.php?title=Cloprednol_acetate&action=edit&redlink=1" class="new" title="Cloprednol acetate (page does not exist)">Cloprednol acetate</a></li></ul></li> <li><a href="/wiki/Corticosterone" title="Corticosterone">Corticosterone</a> <ul><li><a href="/w/index.php?title=Corticosterone_acetate&action=edit&redlink=1" class="new" title="Corticosterone acetate (page does not exist)">Corticosterone acetate</a></li> <li><a href="/w/index.php?title=Corticosterone_benzoate&action=edit&redlink=1" class="new" title="Corticosterone benzoate (page does not exist)">Corticosterone benzoate</a></li></ul></li> <li><a href="/wiki/Cortisol" title="Cortisol">Cortisol</a> (<a href="/wiki/Hydrocortisone" title="Hydrocortisone">hydrocortisone</a>) <ul><li><a href="/wiki/Benzodrocortisone" title="Benzodrocortisone">Benzodrocortisone (hydrocortisone benzoate)</a></li> <li><a href="/wiki/Hydrocortamate" title="Hydrocortamate">Hydrocortamate (hydrocortisone diethylaminoacetate)</a></li> <li><a href="/wiki/List_of_corticosteroid_esters#Hydrocortisone_esters" title="List of corticosteroid esters">Hydrocortisone esters</a></li></ul></li> <li><a href="/wiki/Cortisone" title="Cortisone">Cortisone</a> <ul><li><a href="/wiki/Cortisone_acetate" title="Cortisone acetate">Cortisone acetate</a></li></ul></li> <li><a href="/wiki/Deprodone" title="Deprodone">Deprodone</a> <ul><li><a href="/w/index.php?title=Deprodone_propionate&action=edit&redlink=1" class="new" title="Deprodone propionate (page does not exist)">Deprodone propionate</a></li></ul></li> <li><a href="/wiki/Dichlorisone" title="Dichlorisone">Dichlorisone</a> <ul><li><a href="/w/index.php?title=Dichlorisone_acetate&action=edit&redlink=1" class="new" title="Dichlorisone acetate (page does not exist)">Dichlorisone acetate</a></li> <li><a href="/w/index.php?title=Dichlorisone_diacetate&action=edit&redlink=1" class="new" title="Dichlorisone diacetate (page does not exist)">Dichlorisone diacetate</a></li></ul></li> <li><a href="/wiki/Difluprednate" title="Difluprednate">Difluprednate</a></li> <li><a href="/wiki/Endrisone" title="Endrisone">Endrisone (endrysone)</a></li> <li><a href="/wiki/Etiprednol" title="Etiprednol">Etiprednol</a> <ul><li><a href="/w/index.php?title=Etiprednol_dicloacetate&action=edit&redlink=1" class="new" title="Etiprednol dicloacetate (page does not exist)">Etiprednol dicloacetate (etiprednol dichloroacetate)</a></li></ul></li> <li><a href="/wiki/Fludrocortisone" title="Fludrocortisone">Fludrocortisone (fludrocortone)</a> <ul><li><a href="/wiki/Fludrocortisone_acetate" class="mw-redirect" title="Fludrocortisone acetate">Fludrocortisone acetate</a></li></ul></li> <li><a href="/wiki/Fluorometholone" title="Fluorometholone">Fluorometholone</a> <ul><li><a href="/wiki/Fluorometholone_acetate" title="Fluorometholone acetate">Fluorometholone acetate</a></li></ul></li> <li><a href="/wiki/Fluperolone" title="Fluperolone">Fluperolone</a> <ul><li><a href="/wiki/Fluperolone_acetate" title="Fluperolone acetate">Fluperolone acetate</a></li></ul></li> <li><a href="/wiki/Fluprednisolone" title="Fluprednisolone">Fluprednisolone</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Fluprednisolone_esters" title="List of corticosteroid esters">Fluprednisolone esters</a></li></ul></li> <li><a href="/wiki/Halopredone" title="Halopredone">Halopredone</a> <ul><li><a href="/w/index.php?title=Halopredone_acetate&action=edit&redlink=1" class="new" title="Halopredone acetate (page does not exist)">Halopredone acetate (halopredone diacetate)</a></li></ul></li> <li><a href="/wiki/Isoflupredone" title="Isoflupredone">Isoflupredone (9α-fluoroprednisolone)</a> <ul><li><a href="/w/index.php?title=Isoflupredone_acetate&action=edit&redlink=1" class="new" title="Isoflupredone acetate (page does not exist)">Isoflupredone acetate</a></li></ul></li> <li><a href="/wiki/Loteprednol" title="Loteprednol">Loteprednol</a></li> <li><a href="/wiki/Mazipredone" title="Mazipredone">Mazipredone (depersolone)</a></li> <li><a href="/wiki/Medrysone" title="Medrysone">Medrysone</a></li> <li><a href="/wiki/Methylprednisolone" title="Methylprednisolone">Methylprednisolone</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Methylprednisolone_esters" title="List of corticosteroid esters">Methylprednisolone esters</a></li></ul></li> <li><a href="/wiki/Prebediolone" class="mw-redirect" title="Prebediolone">Prebediolone</a> <ul><li><a href="/wiki/Prebediolone_acetate" title="Prebediolone acetate">Prebediolone acetate</a></li></ul></li> <li><a href="/wiki/Prednisolone" title="Prednisolone">Prednisolone</a> <ul><li><a href="/wiki/Prednazate" title="Prednazate">Prednazate</a></li> <li><a href="/wiki/Prednazoline" title="Prednazoline">Prednazoline</a></li> <li><a href="/wiki/Prednicarbate" title="Prednicarbate">Prednicarbate (prednisolone ethylcarbonate propionate)</a></li> <li><a href="/wiki/Prednimustine" title="Prednimustine">Prednimustine</a></li> <li><a href="/wiki/Prednisolamate" title="Prednisolamate">Prednisolamate (prednisolone diethylaminoacetate)</a></li> <li><a href="/wiki/List_of_corticosteroid_esters#Prednisolone_esters" title="List of corticosteroid esters">Prednisolone esters</a></li></ul></li> <li><a href="/wiki/Prednisone" title="Prednisone">Prednisone</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Prednisone_esters" title="List of corticosteroid esters">Prednisone esters</a></li></ul></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a> <ul><li><a href="/wiki/Pregnenolone_acetate" title="Pregnenolone acetate">Pregnenolone acetate</a></li> <li><a href="/wiki/Pregnenolone_succinate" title="Pregnenolone succinate">Pregnenolone succinate (pregnenolone hemisuccinate)</a></li></ul></li> <li><a href="/wiki/Resocortol" title="Resocortol">Resocortol</a></li> <li><a href="/wiki/Tipredane" title="Tipredane">Tipredane</a></li> <li><a href="/wiki/Tixocortol" title="Tixocortol">Tixocortol</a> <ul><li><a href="/wiki/Butixocort" title="Butixocort">Butixocort (tixocortol butyrate)</a> <ul><li><a href="/w/index.php?title=Butixocort_propionate&action=edit&redlink=1" class="new" title="Butixocort propionate (page does not exist)">Butixocort propionate</a></li></ul></li> <li><a href="/wiki/Tixocortol_pivalate" title="Tixocortol pivalate">Tixocortol pivalate</a></li></ul></li></ul> <ul><li>Methasones and related (16-substituted): <a href="/wiki/16%CE%B1-Methyl-11-oxoprednisolone" title="16α-Methyl-11-oxoprednisolone">16α-Methyl-11-oxoprednisolone</a></li> <li><a href="/wiki/Alclometasone" title="Alclometasone">Alclometasone</a> <ul><li><a href="/wiki/Alclometasone_dipropionate" title="Alclometasone dipropionate">Alclometasone dipropionate</a></li></ul></li> <li><a href="/wiki/Amelometasone" title="Amelometasone">Amelometasone</a></li> <li><a href="/wiki/Beclometasone" title="Beclometasone">Beclometasone (beclomethasone)</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Beclometasone_esters" title="List of corticosteroid esters">Beclometasone esters</a></li></ul></li> <li><a href="/wiki/Betamethasone" title="Betamethasone">Betamethasone (betametasone)</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Betamethasone_esters" title="List of corticosteroid esters">Betamethasone esters</a></li> <li><a href="/wiki/Cortobenzolone" title="Cortobenzolone">Cortobenzolone (betamethasone salicylate)</a></li></ul></li> <li><a href="/wiki/Ciclometasone" title="Ciclometasone">Ciclometasone (ciclomethasone, cyclomethasone)</a></li> <li><a href="/wiki/Clobetasol" title="Clobetasol">Clobetasol</a> <ul><li><a href="/wiki/Clobetasol_propionate" title="Clobetasol propionate">Clobetasol propionate</a></li></ul></li> <li><a href="/wiki/Clobetasone" title="Clobetasone">Clobetasone</a> <ul><li><a href="/wiki/Clobetasone_butyrate" title="Clobetasone butyrate">Clobetasone butyrate</a></li></ul></li> <li><a href="/wiki/Clocortolone" title="Clocortolone">Clocortolone</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Clocortolone_esters" title="List of corticosteroid esters">Clocortolone esters</a></li></ul></li> <li><a href="/wiki/Cloticasone" title="Cloticasone">Cloticasone</a> <ul><li><a href="/w/index.php?title=Cloticasone_propionate&action=edit&redlink=1" class="new" title="Cloticasone propionate (page does not exist)">Cloticasone propionate</a></li></ul></li> <li><a href="/wiki/Cormetasone" title="Cormetasone">Cormetasone (cormethasone)</a> <ul><li><a href="/w/index.php?title=Cormetasone_acetate&action=edit&redlink=1" class="new" title="Cormetasone acetate (page does not exist)">Cormetasone acetate</a></li></ul></li> <li><a href="/wiki/Descinolone" title="Descinolone">Descinolone</a></li> <li><a href="/wiki/Desoximetasone" title="Desoximetasone">Desoximetasone (desoxymethasone)</a></li> <li><a href="/wiki/Dexamethasone" title="Dexamethasone">Dexamethasone (dexametasone)</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Dexamethasone_esters" title="List of corticosteroid esters">Dexamethasone esters</a></li></ul></li> <li><a href="/wiki/Diflorasone" title="Diflorasone">Diflorasone</a> <ul><li><a href="/wiki/Diflorasone_diacetate" title="Diflorasone diacetate">Diflorasone diacetate</a></li></ul></li> <li><a href="/wiki/Diflucortolone" title="Diflucortolone">Diflucortolone</a> <ul><li><a href="/w/index.php?title=Diflucortolone_pivalate&action=edit&redlink=1" class="new" title="Diflucortolone pivalate (page does not exist)">Diflucortolone pivalate</a></li> <li><a href="/wiki/Diflucortolone_valerate" title="Diflucortolone valerate">Diflucortolone valerate</a></li></ul></li> <li><a href="/wiki/Dimesone" title="Dimesone">Dimesone</a> <ul><li><a href="/w/index.php?title=Dimesone_acetate&action=edit&redlink=1" class="new" title="Dimesone acetate (page does not exist)">Dimesone acetate</a></li></ul></li> <li><a href="/wiki/Doxibetasol" title="Doxibetasol">Doxibetasol (doxybetasol)</a></li> <li><a href="/wiki/Fluclorolone" title="Fluclorolone">Fluclorolone</a></li> <li><a href="/wiki/Flumetasone" title="Flumetasone">Flumetasone (flumethasone)</a> <ul><li><a href="/w/index.php?title=Flumetasone_acetate&action=edit&redlink=1" class="new" title="Flumetasone acetate (page does not exist)">Flumetasone acetate</a></li> <li><a href="/wiki/Flumetasone_pivalate" title="Flumetasone pivalate">Flumetasone pivalate</a></li></ul></li> <li><a href="/wiki/Fluocinolone" title="Fluocinolone">Fluocinolone</a></li> <li><a href="/wiki/Fluocortin" title="Fluocortin">Fluocortin</a> <ul><li><a href="/wiki/Fluocortin_butyl" title="Fluocortin butyl">Fluocortin butyl (fluocortin butylate)</a></li></ul></li> <li><a href="/wiki/Fluocortolone" title="Fluocortolone">Fluocortolone</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Fluocortolone_esters" title="List of corticosteroid esters">Fluocortolone esters</a></li></ul></li> <li><a href="/wiki/Fluprednidene" title="Fluprednidene">Fluprednidene (fluprednylidene)</a> <ul><li><a href="/wiki/Fluprednidene_acetate" title="Fluprednidene acetate">Fluprednidene acetate</a></li></ul></li> <li>Fluticasone <ul><li><a href="/wiki/Fluticasone_furoate" title="Fluticasone furoate">Fluticasone furoate</a></li> <li><a href="/wiki/Fluticasone_propionate" title="Fluticasone propionate">Fluticasone propionate</a></li></ul></li> <li><a href="/wiki/Halocortolone" title="Halocortolone">Halocortolone</a></li> <li><a href="/wiki/Halometasone" title="Halometasone">Halometasone</a></li> <li><a href="/wiki/Icometasone" title="Icometasone">Icometasone</a> <ul><li><a href="/w/index.php?title=Icometasone_enbutate&action=edit&redlink=1" class="new" title="Icometasone enbutate (page does not exist)">Icometasone enbutate (icometasone butyrate acetate)</a></li></ul></li> <li><a href="/wiki/Isoprednidene" title="Isoprednidene">Isoprednidene</a></li> <li><a href="/wiki/Locicortolone" title="Locicortolone">Locicortolone (locicortone)</a> <ul><li><a href="/w/index.php?title=Locicortolone_dicibate&action=edit&redlink=1" class="new" title="Locicortolone dicibate (page does not exist)">Locicortolone dicibate (locicortone dicibate)</a></li></ul></li> <li><a href="/wiki/Meclorisone" title="Meclorisone">Meclorisone</a> <ul><li><a href="/w/index.php?title=Meclorisone_dibutyrate&action=edit&redlink=1" class="new" title="Meclorisone dibutyrate (page does not exist)">Meclorisone dibutyrate</a></li></ul></li> <li><a href="/wiki/Meprednisone" title="Meprednisone">Meprednisone (methylprednisone)</a> <ul><li><a href="/w/index.php?title=Meprednisone_acetate&action=edit&redlink=1" class="new" title="Meprednisone acetate (page does not exist)">Meprednisone acetate</a></li> <li><a href="/w/index.php?title=Meprednisone_hydrogen_succinate&action=edit&redlink=1" class="new" title="Meprednisone hydrogen succinate (page does not exist)">Meprednisone hydrogen succinate (methylprednisone hemisuccinate)</a></li></ul></li> <li><a href="/wiki/Mometasone" title="Mometasone">Mometasone</a> <ul><li><a href="/wiki/Mometasone_furoate" class="mw-redirect" title="Mometasone furoate">Mometasone furoate</a></li></ul></li> <li><a href="/wiki/Paramethasone" title="Paramethasone">Paramethasone</a> <ul><li><a href="/wiki/Paramethasone_acetate" title="Paramethasone acetate">Paramethasone acetate</a></li> <li><a href="/w/index.php?title=Paramethasone_disodium_phosphate&action=edit&redlink=1" class="new" title="Paramethasone disodium phosphate (page does not exist)">Paramethasone disodium phosphate</a></li> <li><a href="/w/index.php?title=Paramethasone_phosphate&action=edit&redlink=1" class="new" title="Paramethasone phosphate (page does not exist)">Paramethasone phosphate</a></li></ul></li> <li><a href="/wiki/Prednylidene" title="Prednylidene">Prednylidene</a> <ul><li><a href="/w/index.php?title=Prednylidene_diethylaminoacetate&action=edit&redlink=1" class="new" title="Prednylidene diethylaminoacetate (page does not exist)">Prednylidene diethylaminoacetate</a></li></ul></li> <li><a href="/wiki/Rimexolone" title="Rimexolone">Rimexolone</a></li> <li><a href="/wiki/Ticabesone" title="Ticabesone">Ticabesone</a> <ul><li><a href="/w/index.php?title=Ticabesone_propionate&action=edit&redlink=1" class="new" title="Ticabesone propionate (page does not exist)">Ticabesone propionate</a></li></ul></li> <li><a href="/wiki/Timobesone" title="Timobesone">Timobesone</a> <ul><li><a href="/w/index.php?title=Timobesone_acetate&action=edit&redlink=1" class="new" title="Timobesone acetate (page does not exist)">Timobesone acetate</a></li></ul></li> <li><a href="/wiki/Triamcinolone" title="Triamcinolone">Triamcinolone</a> <ul><li><a href="/wiki/Triamcinolone_diacetate" title="Triamcinolone diacetate">Triamcinolone diacetate</a></li></ul></li> <li><a href="/wiki/Ulobetasol" title="Ulobetasol">Ulobetasol (halobetasol)</a> <ul><li><a href="/wiki/Ulobetasol_propionate" title="Ulobetasol propionate">Ulobetasol propionate</a></li></ul></li> <li><a href="/wiki/Vamorolone" title="Vamorolone">Vamorolone</a></li></ul> <ul><li>Cyclic ketals (16,17-cyclized): <a href="/wiki/Acrocinonide" title="Acrocinonide">Acrocinonide (triamcinolone acroleinide)</a></li> <li><a href="/wiki/Amcinafal" title="Amcinafal">Amcinafal (triamcinolone pentanonide)</a></li> <li><a href="/wiki/Amcinafide" title="Amcinafide">Amcinafide (triamcinolone acetophenide)</a></li> <li><a href="/wiki/Amcinonide" title="Amcinonide">Amcinonide (triamcinolone acetate cyclopentanonide)</a></li> <li><a href="/wiki/Budesonide" title="Budesonide">Budesonide</a></li> <li><a href="/wiki/Ciclesonide" title="Ciclesonide">Ciclesonide</a></li> <li><a href="/wiki/Cicortonide" title="Cicortonide">Cicortonide</a></li> <li><a href="/wiki/Deflazacort" title="Deflazacort">Deflazacort (azacort)</a></li> <li><a href="/wiki/Descinolone_acetonide" title="Descinolone acetonide">Descinolone acetonide</a></li> <li><a href="/wiki/Desonide" title="Desonide">Desonide (hydroxyprednisolone acetonide)</a> <ul><li><a href="/w/index.php?title=Desonide_disodium_phosphate&action=edit&redlink=1" class="new" title="Desonide disodium phosphate (page does not exist)">Desonide disodium phosphate</a></li> <li><a href="/w/index.php?title=Desonide_pivalate&action=edit&redlink=1" class="new" title="Desonide pivalate (page does not exist)">Desonide pivalate</a></li></ul></li> <li><a href="/wiki/Dexbudesonide" title="Dexbudesonide">Dexbudesonide</a></li> <li><a href="/wiki/Drocinonide" title="Drocinonide">Drocinonide</a> <ul><li><a href="/w/index.php?title=Drocinonide_phosphate&action=edit&redlink=1" class="new" title="Drocinonide phosphate (page does not exist)">Drocinonide phosphate</a></li></ul></li> <li><a href="/wiki/Fluazacort" title="Fluazacort">Fluazacort</a></li> <li><a href="/wiki/Fluclorolone_acetonide" title="Fluclorolone acetonide">Fluclorolone acetonide (flucloronide)</a></li> <li><a href="/wiki/Fludroxycortide" title="Fludroxycortide">Fludroxycortide (flurandrenolone, flurandrenolide)</a></li> <li><a href="/wiki/Flumoxonide" title="Flumoxonide">Flumoxonide</a></li> <li><a href="/wiki/Flunisolide" title="Flunisolide">Flunisolide</a> <ul><li><a href="/w/index.php?title=Flunisolide_acetate&action=edit&redlink=1" class="new" title="Flunisolide acetate (page does not exist)">Flunisolide acetate</a></li></ul></li> <li><a href="/wiki/Fluocinolone_acetonide" title="Fluocinolone acetonide">Fluocinolone acetonide</a> <ul><li><a href="/wiki/Ciprocinonide" title="Ciprocinonide">Ciprocinonide (fluocinolone acetonide cyclopropylcarboxylate)</a></li> <li><a href="/wiki/Fluocinonide" title="Fluocinonide">Fluocinonide (fluocinolide, fluocinolone acetonide acetate)</a></li> <li><a href="/wiki/Procinonide" title="Procinonide">Procinonide (fluocinolone acetonide propionate)</a></li></ul></li> <li><a href="/wiki/Formocortal" title="Formocortal">Formocortal</a></li> <li><a href="/wiki/Halcinonide" title="Halcinonide">Halcinonide</a></li> <li><a href="/wiki/Itrocinonide" title="Itrocinonide">Itrocinonide</a></li> <li><a href="/wiki/Rofleponide" title="Rofleponide">Rofleponide</a> <ul><li><a href="/wiki/Rofleponide_palmitate" class="mw-redirect" title="Rofleponide palmitate">Rofleponide palmitate</a></li></ul></li> <li><a href="/wiki/Tralonide" title="Tralonide">Tralonide</a></li> <li><a href="/wiki/Triamcinolone_acetonide" title="Triamcinolone acetonide">Triamcinolone acetonide</a> <ul><li><a href="/wiki/Flupamesone" title="Flupamesone">Flupamesone (triamcinolone acetonide metembonate)</a></li> <li><a href="/wiki/List_of_corticosteroid_esters#Triamcinolone_acetonide_esters" title="List of corticosteroid esters">Triamcinolone acetonide esters</a></li></ul></li> <li><a href="/wiki/Triamcinolone_aminobenzal_benzamidoisobutyrate" title="Triamcinolone aminobenzal benzamidoisobutyrate">Triamcinolone aminobenzal benzamidoisobutyrate (TBI-PAB)</a></li> <li><a href="/wiki/Triclonide" title="Triclonide">Triclonide</a></li></ul> <ul><li>Others/atypical (other expanded steroid ring systems, homosteroids, and non-pregnane steroids): <a href="/wiki/Cortisuzol" title="Cortisuzol">Cortisuzol</a></li> <li><a href="/wiki/Cortivazol" title="Cortivazol">Cortivazol</a></li> <li><a href="/wiki/Domoprednate" title="Domoprednate">Domoprednate</a></li> <li><a href="/wiki/Naflocort" title="Naflocort">Naflocort</a></li> <li><a href="/wiki/Nicocortonide" title="Nicocortonide">Nicocortonide</a> <ul><li><a href="/w/index.php?title=Nicocortonide_acetate&action=edit&redlink=1" class="new" title="Nicocortonide acetate (page does not exist)">Nicocortonide acetate</a></li></ul></li> <li><a href="/wiki/Nivacortol" title="Nivacortol">Nivacortol (nivazol)</a></li> <li><a href="/wiki/Oxisopred" title="Oxisopred">Oxisopred</a></li> <li><a href="/w/index.php?title=RU-26988&action=edit&redlink=1" class="new" title="RU-26988 (page does not exist)">RU-26988</a></li> <li><a href="/wiki/RU-28362" title="RU-28362">RU-28362</a></li></ul> <ul><li>Non-corticosteroids with some glucocorticoid activity: <a href="/wiki/15%CE%B2-Hydroxycyproterone_acetate" title="15β-Hydroxycyproterone acetate">15β-Hydroxycyproterone acetate</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone</a></li> <li><a href="/wiki/Bromoketoprogesterone" title="Bromoketoprogesterone">Bromoketoprogesterone</a></li> <li><a href="/wiki/Chlormadinone_acetate" title="Chlormadinone acetate">Chlormadinone acetate</a></li> <li><a href="/wiki/Cyproterone" title="Cyproterone">Cyproterone</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Danazol" title="Danazol">Danazol</a></li> <li><a href="/wiki/Delmadinone_acetate" title="Delmadinone acetate">Delmadinone acetate</a></li> <li><a href="/wiki/Desogestrel" title="Desogestrel">Desogestrel</a></li> <li><a href="/wiki/DU-41165" title="DU-41165">DU-41165</a></li> <li><a href="/wiki/Etonogestrel" title="Etonogestrel">Etonogestrel</a></li> <li><a href="/wiki/Flugestone" title="Flugestone">Flugestone</a></li> <li><a href="/wiki/Flugestone_acetate" title="Flugestone acetate">Flugestone acetate (flurogestone acetate)</a></li> <li><a href="/wiki/Fluoromedroxyprogesterone_acetate" title="Fluoromedroxyprogesterone acetate">Fluoromedroxyprogesterone acetate</a></li> <li><a href="/wiki/Fluoxymesterone" title="Fluoxymesterone">Fluoxymesterone</a></li> <li><a href="/wiki/Gestodene" title="Gestodene">Gestodene</a></li> <li><a href="/wiki/Medrogestone" title="Medrogestone">Medrogestone</a></li> <li><a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">Medroxyprogesterone acetate</a></li> <li><a href="/wiki/Megestrol_acetate" title="Megestrol acetate">Megestrol acetate</a></li> <li><a href="/wiki/Metribolone" title="Metribolone">Metribolone</a></li> <li><a href="/wiki/Norgestomet" title="Norgestomet">Norgestomet</a></li> <li><a href="/wiki/Osaterone_acetate" title="Osaterone acetate">Osaterone acetate</a></li> <li><a class="mw-selflink selflink">Progesterone</a></li> <li><a href="/wiki/Promegestone" title="Promegestone">Promegestone</a></li> <li><a href="/wiki/RU-2309" title="RU-2309">RU-2309</a></li> <li><a href="/wiki/Quingestrone" title="Quingestrone">Quingestrone</a></li> <li><a href="/wiki/Segesterone_acetate" title="Segesterone acetate">Segesterone acetate (nestorone)</a></li> <li><a href="/wiki/Tetrahydrogestrinone" title="Tetrahydrogestrinone">Tetrahydrogestrinone</a></li></ul> <ul><li>Nonsteroidal glucocorticoids: <a href="/wiki/AZD-5423" title="AZD-5423">AZD-5423</a></li> <li><a href="/w/index.php?title=GSK-9027&action=edit&redlink=1" class="new" title="GSK-9027 (page does not exist)">GSK-9027</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Mixed (<a href="/wiki/Selective_glucocorticoid_receptor_agonists" class="mw-redirect" title="Selective glucocorticoid receptor agonists"><abbr title="Selective glucocorticoid receptor agonists">SEGRMs</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 glucocorticoid receptor 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/Dagrocorat" title="Dagrocorat">Dagrocorat</a></li> <li><a href="/wiki/Fosdagrocorat" title="Fosdagrocorat">Fosdagrocorat</a></li> <li><a href="/wiki/Mapracorat" title="Mapracorat">Mapracorat</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center"><a href="/wiki/Antiglucocorticoid" title="Antiglucocorticoid">Antagonists</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/7%CE%B1-Hydroxy-DHEA" title="7α-Hydroxy-DHEA">7α-Hydroxy-DHEA</a></li> <li><a href="/wiki/17%CE%B1-Methylprogesterone" title="17α-Methylprogesterone">17α-Methylprogesterone</a></li> <li><a href="/wiki/Aglepristone" title="Aglepristone">Aglepristone</a></li> <li><a href="/wiki/Asoprisnil" title="Asoprisnil">Asoprisnil</a></li> <li><a href="/wiki/Asoprisnil_ecamate" title="Asoprisnil ecamate">Asoprisnil ecamate</a></li> <li><a href="/w/index.php?title=C108297&action=edit&redlink=1" class="new" title="C108297 (page does not exist)">C108297</a></li> <li><a href="/w/index.php?title=C113176&action=edit&redlink=1" class="new" title="C113176 (page does not exist)">C113176</a></li> <li><a href="/w/index.php?title=CORT-108297&action=edit&redlink=1" class="new" title="CORT-108297 (page does not exist)">CORT-108297</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/w/index.php?title=Dazucorilant&action=edit&redlink=1" class="new" title="Dazucorilant (page does not exist)">Dazucorilant</a></li> <li><a href="/w/index.php?title=Exicorilant&action=edit&redlink=1" class="new" title="Exicorilant (page does not exist)">Exicorilant (CORT-125281)</a></li> <li><a href="/wiki/Guggulsterone" title="Guggulsterone">Guggulsterone</a></li> <li><a href="/wiki/Ketoconazole" title="Ketoconazole">Ketoconazole</a></li> <li><a href="/wiki/Lilopristone" title="Lilopristone">Lilopristone</a></li> <li><a href="/w/index.php?title=LLY-2707&action=edit&redlink=1" class="new" title="LLY-2707 (page does not exist)">LLY-2707</a></li> <li><a href="/wiki/Metapristone" title="Metapristone">Metapristone (RU-42633)</a></li> <li><a href="/wiki/Miconazole" title="Miconazole">Miconazole</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone (RU-486)</a></li> <li><a href="/wiki/Miricorilant" title="Miricorilant">Miricorilant (CORT-118335)</a></li> <li><a href="/wiki/Onapristone" title="Onapristone">Onapristone</a></li> <li><a href="/w/index.php?title=ORG-34116&action=edit&redlink=1" class="new" title="ORG-34116 (page does not exist)">ORG-34116</a></li> <li><a href="/w/index.php?title=ORG-34517&action=edit&redlink=1" class="new" title="ORG-34517 (page does not exist)">ORG-34517 (SCH-900636)</a></li> <li><a href="/w/index.php?title=Org_34850&action=edit&redlink=1" class="new" title="Org 34850 (page does not exist)">ORG-34850</a></li> <li><a href="/wiki/Pregnenolone_16%CE%B1-carbonitrile" title="Pregnenolone 16α-carbonitrile">Pregnenolone 16α-carbonitrile</a></li> <li><a href="/wiki/Relacorilant" title="Relacorilant">Relacorilant (CORT-125134)</a></li> <li><a href="/wiki/RTI_3021%E2%80%93012" class="mw-redirect" title="RTI 3021–012">RTI 3021–012</a></li> <li><a href="/w/index.php?title=RTI_3021%E2%80%93022&action=edit&redlink=1" class="new" title="RTI 3021–022 (page does not exist)">RTI 3021–022</a></li> <li><a href="/wiki/Telapristone" title="Telapristone">Telapristone</a></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li> <li><a href="/wiki/Toripristone" title="Toripristone">Toripristone</a></li> <li><a href="/wiki/Ulipristal_acetate" title="Ulipristal acetate">Ulipristal acetate</a></li> <li><a href="/w/index.php?title=Zavacorilant&action=edit&redlink=1" class="new" title="Zavacorilant (page does not exist)">Zavacorilant</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;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>Antisense oligonucleotides: <a href="/wiki/IONIS-GCCRRx" title="IONIS-GCCRRx">IONIS-GCCRRx (ISIS-426115)</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:Glucocorticoids_and_antiglucocorticoids" title="Template:Glucocorticoids and antiglucocorticoids">Glucocorticoids and antiglucocorticoids</a></dd> <dd><a href="/wiki/Template:Mineralocorticoid_receptor_modulators" title="Template:Mineralocorticoid receptor modulators">Mineralocorticoid receptor modulators</a></dd> <dd><a href="/wiki/List_of_corticosteroids" title="List of corticosteroids">List of corticosteroids</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="Mineralocorticoid_receptor_modulators767" 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:Mineralocorticoid_receptor_modulators" title="Template:Mineralocorticoid receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Mineralocorticoid_receptor_modulators" title="Template talk:Mineralocorticoid receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Mineralocorticoid_receptor_modulators" title="Special:EditPage/Template:Mineralocorticoid receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Mineralocorticoid_receptor_modulators767" style="font-size:114%;margin:0 4em"><a href="/wiki/Mineralocorticoid_receptor" title="Mineralocorticoid receptor">Mineralocorticoid 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/Mineralocorticoid_receptor" title="Mineralocorticoid receptor"><abbr title="Mineralocorticoid receptor">MR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Mineralocorticoid receptor</th><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><a href="/wiki/11-Dehydrocorticosterone" title="11-Dehydrocorticosterone">11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone)</a> <ul><li><a href="/w/index.php?title=11-Dehydrocorticosterone_acetate&action=edit&redlink=1" class="new" title="11-Dehydrocorticosterone acetate (page does not exist)">11-Dehydrocorticosterone acetate</a></li></ul></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone (desoxycortone, deoxycortone, desoxycorticosterone)</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Desoxycortone_esters" title="List of corticosteroid esters">Desoxycortone esters</a></li></ul></li> <li><a href="/wiki/11-Deoxycortisol" title="11-Deoxycortisol">11-Deoxycortisol (cortodoxone, cortexolone)</a> <ul><li><a href="/wiki/Cortifen" title="Cortifen">Cortifen (cortiphen, kortifen)</a></li> <li><a href="/w/index.php?title=Cortodoxone_acetate&action=edit&redlink=1" class="new" title="Cortodoxone acetate (page does not exist)">Cortodoxone acetate</a></li></ul></li> <li><a href="/wiki/11%CE%B2-Hydroxyprogesterone" title="11β-Hydroxyprogesterone">11β-Hydroxyprogesterone</a></li> <li><a href="/w/index.php?title=16%CE%B1,18-Dihydroxy-11-deoxycorticosterone&action=edit&redlink=1" class="new" title="16α,18-Dihydroxy-11-deoxycorticosterone (page does not exist)">16α,18-Dihydroxy-11-deoxycorticosterone</a></li> <li><a href="/w/index.php?title=17%CE%B1-Hydroxyaldosterone&action=edit&redlink=1" class="new" title="17α-Hydroxyaldosterone (page does not exist)">17α-Hydroxyaldosterone</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/19-Norprogesterone" title="19-Norprogesterone">19-Norprogesterone</a></li> <li><a href="/wiki/Aldosterone" title="Aldosterone">Aldosterone</a></li> <li><a href="/wiki/Corticosterone" title="Corticosterone">Corticosterone</a> <ul><li><a href="/w/index.php?title=Corticosterone_acetate&action=edit&redlink=1" class="new" title="Corticosterone acetate (page does not exist)">Corticosterone acetate</a></li> <li><a href="/w/index.php?title=Corticosterone_benzoate&action=edit&redlink=1" class="new" title="Corticosterone benzoate (page does not exist)">Corticosterone benzoate</a></li></ul></li> <li><a href="/wiki/Cortisol" title="Cortisol">Cortisol</a> (<a href="/wiki/Hydrocortisone" title="Hydrocortisone">hydrocortisone</a>) <ul><li><a href="/wiki/Benzodrocortisone" title="Benzodrocortisone">Benzodrocortisone (hydrocortisone benzoate)</a></li> <li><a href="/wiki/Hydrocortamate" title="Hydrocortamate">Hydrocortamate (hydrocortisone diethylaminoacetate)</a></li> <li><a href="/wiki/List_of_corticosteroid_esters#Hydrocortisone_esters" title="List of corticosteroid esters">Hydrocortisone esters</a></li></ul></li> <li><a href="/wiki/Cortisone" title="Cortisone">Cortisone</a> <ul><li><a href="/wiki/Cortisone_acetate" title="Cortisone acetate">Cortisone acetate</a></li></ul></li> <li><a href="/wiki/Fludrocortisone" title="Fludrocortisone">Fludrocortisone (fludrocortone)</a> <ul><li><a href="/wiki/Fludrocortisone_acetate" class="mw-redirect" title="Fludrocortisone acetate">Fludrocortisone acetate</a></li></ul></li> <li><a href="/wiki/Mometasone" title="Mometasone">Mometasone</a> <ul><li><a href="/wiki/Mometasone_furoate" class="mw-redirect" title="Mometasone furoate">Mometasone furoate</a></li></ul></li> <li><a href="/wiki/Prednisolone" title="Prednisolone">Prednisolone</a> <ul><li><a href="/wiki/Prednazate" title="Prednazate">Prednazate</a></li> <li><a href="/wiki/Prednazoline" title="Prednazoline">Prednazoline</a></li> <li><a href="/wiki/Prednicarbate" title="Prednicarbate">Prednicarbate (prednisolone ethylcarbonate propionate)</a></li> <li><a href="/wiki/Prednimustine" title="Prednimustine">Prednimustine</a></li> <li><a href="/wiki/Prednisolamate" title="Prednisolamate">Prednisolamate (prednisolone diethylaminoacetate)</a></li> <li><a href="/wiki/List_of_corticosteroid_esters#Prednisolone_esters" title="List of corticosteroid esters">Prednisolone esters</a></li></ul></li> <li><a href="/wiki/Prednisone" title="Prednisone">Prednisone</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Prednisone_esters" title="List of corticosteroid esters">Prednisone esters</a></li></ul></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-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Steroidal: <a href="/wiki/6%CE%B2-Hydroxy-7%CE%B1-thiomethylspironolactone" title="6β-Hydroxy-7α-thiomethylspironolactone">6β-Hydroxy-7α-thiomethylspironolactone</a></li> <li><a href="/w/index.php?title=7%CE%B1-Acetylthio-17%CE%B1-hydroxyprogesterone&action=edit&redlink=1" class="new" title="7α-Acetylthio-17α-hydroxyprogesterone (page does not exist)">7α-Acetylthio-17α-hydroxyprogesterone</a></li> <li><a href="/wiki/7%CE%B1-Thiomethylspironolactone" title="7α-Thiomethylspironolactone">7α-Thiomethylspironolactone (SC-26519)</a></li> <li><a href="/wiki/7%CE%B1-Thioprogesterone" title="7α-Thioprogesterone">7α-Thioprogesterone (SC-8365)</a></li> <li><a href="/wiki/7%CE%B1-Thiospironolactone" title="7α-Thiospironolactone">7α-Thiospironolactone (SC-24813)</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 (hydroxyprogesterone)</a></li> <li><a href="/wiki/18-Deoxyaldosterone" title="18-Deoxyaldosterone">18-Deoxyaldosterone</a></li> <li><a href="/w/index.php?title=18,19-Dinorprogesterone&action=edit&redlink=1" class="new" title="18,19-Dinorprogesterone (page does not exist)">18,19-Dinorprogesterone</a></li> <li><a href="/wiki/Potassium_canrenoate" title="Potassium canrenoate">Canrenoate potassium (potassium canrenoate)</a></li> <li><a href="/wiki/Canrenoic_acid" title="Canrenoic acid">Canrenoic acid (canrenoate)</a></li> <li><a href="/wiki/Canrenone" title="Canrenone">Canrenone (canrenoate y-lactone)</a></li> <li><a href="/wiki/Dicirenone" title="Dicirenone">Dicirenone</a></li> <li><a href="/wiki/Dimethisterone" title="Dimethisterone">Dimethisterone</a></li> <li><a href="/wiki/Drospirenone" title="Drospirenone">Drospirenone</a></li> <li><a href="/wiki/Dydrogesterone" title="Dydrogesterone">Dydrogesterone</a></li> <li><a href="/wiki/Eplerenone" title="Eplerenone">Eplerenone</a></li> <li><a href="/wiki/Gestodene" title="Gestodene">Gestodene</a></li> <li><a href="/wiki/Guggulsterone" title="Guggulsterone">Guggulsterone</a></li> <li><a href="/wiki/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">Hydroxyprogesterone caproate</a></li> <li><a href="/wiki/Medrogestone" title="Medrogestone">Medrogestone</a></li> <li><a href="/wiki/Mespirenone" title="Mespirenone">Mespirenone</a></li> <li><a href="/wiki/Metribolone" title="Metribolone">Metribolone</a></li> <li><a href="/wiki/Mexrenoate_potassium" title="Mexrenoate potassium">Mexrenoate potassium</a></li> <li><a href="/wiki/Mexrenoic_acid" title="Mexrenoic acid">Mexrenoic acid (mexrenoate)</a></li> <li><a href="/wiki/Mexrenone" title="Mexrenone">Mexrenone</a></li> <li><a href="/wiki/Oxprenoic_acid" title="Oxprenoic acid">Oxprenoic acid (oxprenoate)</a></li> <li><a href="/wiki/Oxprenoate_potassium" title="Oxprenoate potassium">Oxprenoate potassium (RU-28318)</a></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a></li> <li><a class="mw-selflink selflink">Progesterone</a></li> <li><a href="/wiki/Prorenoate_potassium" title="Prorenoate potassium">Prorenoate potassium</a></li> <li><a href="/wiki/Prorenoic_acid" title="Prorenoic acid">Prorenoic acid (prorenoate)</a></li> <li><a href="/wiki/Prorenone" title="Prorenone">Prorenone</a></li> <li><a href="/w/index.php?title=RO-14-9012&action=edit&redlink=1" class="new" title="RO-14-9012 (page does not exist)">RO-14-9012</a></li> <li><a href="/w/index.php?title=RU-26752&action=edit&redlink=1" class="new" title="RU-26752 (page does not exist)">RU-26752</a></li> <li><a href="/wiki/SC-5233" title="SC-5233">SC-5233 (spirolactone)</a></li> <li><a href="/wiki/SC-8109" title="SC-8109">SC-8109</a></li> <li><a href="/w/index.php?title=SC-11927&action=edit&redlink=1" class="new" title="SC-11927 (page does not exist)">SC-11927 (CS-1)</a></li> <li><a href="/w/index.php?title=SC-19886&action=edit&redlink=1" class="new" title="SC-19886 (page does not exist)">SC-19886</a></li> <li><a href="/w/index.php?title=SC-27169&action=edit&redlink=1" class="new" title="SC-27169 (page does not exist)">SC-27169</a></li> <li><a href="/wiki/Spirorenone" title="Spirorenone">Spirorenone</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/wiki/Spiroxasone" title="Spiroxasone">Spiroxasone</a></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li> <li><a href="/wiki/Trimegestone" title="Trimegestone">Trimegestone</a></li> <li><a href="/wiki/Vamorolone" title="Vamorolone">Vamorolone</a></li> <li><a href="/w/index.php?title=ZK-91587&action=edit&redlink=1" class="new" title="ZK-91587 (page does not exist)">ZK-91587</a></li> <li><a href="/w/index.php?title=ZK-97894&action=edit&redlink=1" class="new" title="ZK-97894 (page does not exist)">ZK-97894</a></li></ul> <ul><li>Nonsteroidal: <a href="/wiki/Amlodipine" title="Amlodipine">Amlodipine</a></li> <li><a href="/wiki/Apararenone" title="Apararenone">Apararenone</a></li> <li><a href="/wiki/Benidipine" title="Benidipine">Benidipine</a></li> <li><a href="/w/index.php?title=BR-4628&action=edit&redlink=1" class="new" title="BR-4628 (page does not exist)">BR-4628</a></li> <li><a href="/wiki/Esaxerenone" title="Esaxerenone">Esaxerenone</a></li> <li><a href="/wiki/Felodipine" title="Felodipine">Felodipine</a></li> <li><a href="/wiki/Finerenone" title="Finerenone">Finerenone</a></li> <li><a href="/wiki/Miricorilant" title="Miricorilant">Miricorilant (CORT-118335)</a></li> <li><a href="/wiki/Nifedipine" title="Nifedipine">Nifedipine</a></li> <li><a href="/wiki/Nimodipine" title="Nimodipine">Nimodipine</a></li> <li><a href="/wiki/Nitrendipine" title="Nitrendipine">Nitrendipine</a></li> <li><a href="/wiki/Ocedurenone" title="Ocedurenone">Ocedurenone</a></li> <li><a href="/w/index.php?title=PF-03882845&action=edit&redlink=1" class="new" title="PF-03882845 (page does not exist)">PF-03882845</a></li> <li><a href="/w/index.php?title=SM-368229&action=edit&redlink=1" class="new" title="SM-368229 (page does not exist)">SM-368229</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:Mineralocorticoids_and_antimineralocorticoids" title="Template:Mineralocorticoids and antimineralocorticoids">Mineralocorticoids and antimineralocorticoids</a></dd> <dd><a href="/wiki/Template:Glucocorticoid_receptor_modulators" title="Template:Glucocorticoid receptor modulators">Glucocorticoid receptor modulators</a></dd> <dd><a href="/wiki/List_of_corticosteroids" title="List of corticosteroids">List of corticosteroids</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="Nicotinic_acetylcholine_receptor_modulators859" 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:Nicotinic_acetylcholine_receptor_modulators" title="Template:Nicotinic acetylcholine receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Nicotinic_acetylcholine_receptor_modulators" title="Template talk:Nicotinic acetylcholine receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Nicotinic_acetylcholine_receptor_modulators" title="Special:EditPage/Template:Nicotinic acetylcholine receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Nicotinic_acetylcholine_receptor_modulators859" style="font-size:114%;margin:0 4em"><a href="/wiki/Nicotinic_acetylcholine_receptor" title="Nicotinic acetylcholine receptor">Nicotinic acetylcholine 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/Nicotinic_acetylcholine_receptors" class="mw-redirect" title="Nicotinic acetylcholine receptors"><abbr title="Nicotinic acetylcholine receptors">nAChRs</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 Nicotinic acetylcholine receptors</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%;text-align:center;"><a href="/wiki/Receptor_agonist" class="mw-redirect" title="Receptor agonist">Agonists</a> (and <a href="/wiki/Positive_allosteric_modulators" class="mw-redirect" title="Positive allosteric modulators"><abbr title="positive allosteric modulators">PAMs</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 positive allosteric modulators)</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-Hydroxyindoleacetic_acid" title="5-Hydroxyindoleacetic acid">5-HIAA</a></li> <li><a href="/wiki/6-Chloronicotine" title="6-Chloronicotine">6-Chloronicotine</a></li> <li><a href="/wiki/A-84,543" title="A-84,543">A-84,543</a></li> <li><a href="/wiki/A-366,833" title="A-366,833">A-366,833</a></li> <li><a href="/w/index.php?title=A-582,941&action=edit&redlink=1" class="new" title="A-582,941 (page does not exist)">A-582,941</a></li> <li><a href="/w/index.php?title=A-867,744&action=edit&redlink=1" class="new" title="A-867,744 (page does not exist)">A-867,744</a></li> <li><a href="/wiki/ABT-202" title="ABT-202">ABT-202</a></li> <li><a href="/wiki/ABT-418" title="ABT-418">ABT-418</a></li> <li><a href="/w/index.php?title=ABT-560&action=edit&redlink=1" class="new" title="ABT-560 (page does not exist)">ABT-560</a></li> <li><a href="/w/index.php?title=ABT-894&action=edit&redlink=1" class="new" title="ABT-894 (page does not exist)">ABT-894</a></li> <li><a href="/wiki/Acetylcholine" title="Acetylcholine">Acetylcholine</a></li> <li><a href="/wiki/Altinicline" title="Altinicline">Altinicline</a></li> <li><a href="/wiki/Anabasine" title="Anabasine">Anabasine</a></li> <li><a href="/wiki/Anatabine" title="Anatabine">Anatabine</a></li> <li><a href="/wiki/Anatoxin-a" title="Anatoxin-a">Anatoxin-a</a></li> <li><a href="/wiki/AR-R17779" title="AR-R17779">AR-R17779</a></li> <li><a href="/wiki/Bephenium_hydroxynaphthoate" title="Bephenium hydroxynaphthoate">Bephenium hydroxynaphthoate</a></li> <li><a href="/wiki/Butinoline" title="Butinoline">Butinoline</a></li> <li><a href="/wiki/Butyrylcholine" title="Butyrylcholine">Butyrylcholine</a></li> <li><a href="/wiki/Carbachol" title="Carbachol">Carbachol</a></li> <li><a href="/wiki/Choline" title="Choline">Choline</a></li> <li><a href="/wiki/Choline_m-bromophenyl_ether" title="Choline m-bromophenyl ether">Choline m-bromophenyl ether</a></li> <li><a href="/wiki/Cotinine" title="Cotinine">Cotinine</a></li> <li><a href="/wiki/Cytisine" title="Cytisine">Cytisine</a></li> <li><a href="/wiki/Decamethonium" title="Decamethonium">Decamethonium</a></li> <li><a href="/wiki/Desformylflustrabromine" title="Desformylflustrabromine">Desformylflustrabromine</a></li> <li><a href="/wiki/Dianicline" title="Dianicline">Dianicline</a></li> <li><a href="/wiki/Dimethylphenylpiperazinium" title="Dimethylphenylpiperazinium">Dimethylphenylpiperazinium</a></li> <li><a href="/wiki/Epibatidine" title="Epibatidine">Epibatidine</a></li> <li><a href="/wiki/Epiboxidine" title="Epiboxidine">Epiboxidine</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a></li> <li><a href="/w/index.php?title=Ethoxysebacylcholine&action=edit&redlink=1" class="new" title="Ethoxysebacylcholine (page does not exist)">Ethoxysebacylcholine</a></li> <li><a href="/w/index.php?title=EVP-4473&action=edit&redlink=1" class="new" title="EVP-4473 (page does not exist)">EVP-4473</a></li> <li><a href="/wiki/EVP-6124" class="mw-redirect" title="EVP-6124">EVP-6124</a></li> <li><a href="/wiki/Galantamine" title="Galantamine">Galantamine</a></li> <li><a href="/wiki/GTS-21" title="GTS-21">GTS-21</a></li> <li><a href="/wiki/Ispronicline" title="Ispronicline">Ispronicline</a></li> <li><a href="/wiki/Ivermectin" title="Ivermectin">Ivermectin</a></li> <li><a href="/wiki/JNJ-39393406" title="JNJ-39393406">JNJ-39393406</a></li> <li><a href="/wiki/Levamisole" title="Levamisole">Levamisole</a></li> <li><a href="/wiki/Lobeline" title="Lobeline">Lobeline</a></li> <li><a href="/w/index.php?title=MEM-63,908&action=edit&redlink=1" class="new" title="MEM-63,908 (page does not exist)">MEM-63,908 (RG-3487)</a></li> <li><a href="/wiki/Morantel" title="Morantel">Morantel</a></li> <li><a href="/wiki/Nicotine" title="Nicotine">Nicotine</a> (<a href="/wiki/Tobacco" title="Tobacco">tobacco</a>)</li> <li><a href="/w/index.php?title=NS-1738&action=edit&redlink=1" class="new" title="NS-1738 (page does not exist)">NS-1738</a></li> <li><a href="/wiki/PHA-543,613" title="PHA-543,613">PHA-543,613</a></li> <li><a href="/w/index.php?title=PHA-709,829&action=edit&redlink=1" class="new" title="PHA-709,829 (page does not exist)">PHA-709,829</a></li> <li><a href="/wiki/PNU-120,596" title="PNU-120,596">PNU-120,596</a></li> <li><a href="/wiki/PNU-282,987" title="PNU-282,987">PNU-282,987</a></li> <li><a href="/wiki/Pozanicline" title="Pozanicline">Pozanicline</a></li> <li><a href="/wiki/Pyrantel" title="Pyrantel">Pyrantel</a></li> <li><a href="/wiki/Rivanicline" title="Rivanicline">Rivanicline</a></li> <li><a href="/wiki/RJR-2429" title="RJR-2429">RJR-2429</a></li> <li><a href="/wiki/Sazetidine_A" title="Sazetidine A">Sazetidine A</a></li> <li><a href="/wiki/SB-206553" title="SB-206553">SB-206553</a></li> <li><a href="/w/index.php?title=Sebacylcholine&action=edit&redlink=1" class="new" title="Sebacylcholine (page does not exist)">Sebacylcholine</a></li> <li><a href="/wiki/SIB-1508Y" class="mw-redirect" title="SIB-1508Y">SIB-1508Y</a></li> <li><a href="/wiki/SIB-1553A" title="SIB-1553A">SIB-1553A</a></li> <li><a href="/wiki/SSR-180,711" title="SSR-180,711">SSR-180,711</a></li> <li><a href="/w/index.php?title=Suberyldicholine&action=edit&redlink=1" class="new" title="Suberyldicholine (page does not exist)">Suberyldicholine</a></li> <li><a href="/wiki/Suxamethonium" class="mw-redirect" title="Suxamethonium">Suxamethonium (succinylcholine)</a></li> <li><a href="/wiki/Suxethonium_chloride" title="Suxethonium chloride">Suxethonium (succinyldicholine)</a></li> <li><a href="/wiki/TC-1698" title="TC-1698">TC-1698</a></li> <li><a href="/w/index.php?title=TC-1734&action=edit&redlink=1" class="new" title="TC-1734 (page does not exist)">TC-1734</a></li> <li><a href="/wiki/TC-1827" title="TC-1827">TC-1827</a></li> <li><a href="/wiki/TC-2216" title="TC-2216">TC-2216</a></li> <li><a href="/wiki/TC-5214" class="mw-redirect" title="TC-5214">TC-5214</a></li> <li><a href="/wiki/TC-5619" class="mw-redirect" title="TC-5619">TC-5619</a></li> <li><a href="/w/index.php?title=TC-6683&action=edit&redlink=1" class="new" title="TC-6683 (page does not exist)">TC-6683</a></li> <li><a href="/wiki/Tebanicline" title="Tebanicline">Tebanicline</a></li> <li><a href="/wiki/Tribendimidine" title="Tribendimidine">Tribendimidine</a></li> <li><a href="/wiki/Tropisetron" title="Tropisetron">Tropisetron</a></li> <li><a href="/wiki/UB-165" title="UB-165">UB-165</a></li> <li><a href="/wiki/Varenicline" title="Varenicline">Varenicline</a></li> <li><a href="/wiki/WAY-317,538" class="mw-redirect" title="WAY-317,538">WAY-317,538</a></li> <li><a href="/w/index.php?title=XY-4083&action=edit&redlink=1" class="new" title="XY-4083 (page does not exist)">XY-4083</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Receptor_antagonist" title="Receptor antagonist">Antagonists</a> (and <a href="/wiki/Negative_allosteric_modulators" class="mw-redirect" title="Negative allosteric modulators"><abbr title="negative allosteric modulators">NAMs</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 negative allosteric modulators)</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/18-Methylaminocoronaridine" title="18-Methylaminocoronaridine">18-MAC</a></li> <li><a href="/wiki/18-Methoxycoronaridine" title="18-Methoxycoronaridine">18-MC</a></li> <li><a href="/wiki/%CE%91-Neurotoxin" title="Α-Neurotoxin">α-Neurotoxins</a> (e.g., <a href="/wiki/%CE%91-bungarotoxin" class="mw-redirect" title="Α-bungarotoxin">α-bungarotoxin</a>, <a href="/wiki/%CE%91-cobratoxin" class="mw-redirect" title="Α-cobratoxin">α-cobratoxin</a>, <a href="/wiki/%CE%91-conotoxin" class="mw-redirect" title="Α-conotoxin">α-conotoxin</a>, many others)</li> <li><a href="/w/index.php?title=ABT-126&action=edit&redlink=1" class="new" title="ABT-126 (page does not exist)">ABT-126</a></li> <li><a href="/wiki/Alcuronium" class="mw-redirect" title="Alcuronium">Alcuronium</a></li> <li><a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone</a></li> <li><a href="/wiki/Amantadine" title="Amantadine">Amantadine</a></li> <li><a href="/w/index.php?title=Anatruxonium&action=edit&redlink=1" class="new" title="Anatruxonium (page does not exist)">Anatruxonium</a></li> <li><a href="/w/index.php?title=AQW051&action=edit&redlink=1" class="new" title="AQW051 (page does not exist)">AQW051</a></li> <li><a href="/wiki/Atracurium" class="mw-redirect" title="Atracurium">Atracurium</a></li> <li><a href="/wiki/Barbiturates" class="mw-redirect" title="Barbiturates">Barbiturates</a> (e.g., <a href="/wiki/Pentobarbital" title="Pentobarbital">pentobarbital</a>, <a href="/wiki/Sodium_thiopental" title="Sodium thiopental">sodium thiopental</a>)</li> <li><a href="/wiki/BNC-210" class="mw-redirect" title="BNC-210">BNC-210</a></li> <li><a href="/wiki/Bungarotoxin" title="Bungarotoxin">Bungarotoxins</a> (e.g., <a href="/wiki/%CE%91-bungarotoxin" class="mw-redirect" title="Α-bungarotoxin">α-bungarotoxin</a>, <a href="/wiki/%CE%9A-bungarotoxin" class="mw-redirect" title="Κ-bungarotoxin">κ-bungarotoxin</a>)</li> <li><a href="/wiki/Bupropion" title="Bupropion">Bupropion</a></li> <li><a href="/wiki/BW284C51" title="BW284C51">BW284C51</a></li> <li><a href="/wiki/BW-A444" title="BW-A444">BW-A444</a></li> <li><a href="/wiki/Candocuronium_iodide" title="Candocuronium iodide">Candocuronium iodide (chandonium iodide)</a></li> <li><a href="/wiki/Chlorisondamine" title="Chlorisondamine">Chlorisondamine</a></li> <li><a href="/wiki/Cisatracurium" class="mw-redirect" title="Cisatracurium">Cisatracurium</a></li> <li><a href="/wiki/Coclaurine" title="Coclaurine">Coclaurine</a></li> <li><a href="/wiki/Coronaridine" title="Coronaridine">Coronaridine</a></li> <li><a href="/wiki/Curare" title="Curare">Curare</a></li> <li><a href="/wiki/Cyclopropane" title="Cyclopropane">Cyclopropane</a></li> <li><a href="/wiki/Dacuronium_bromide" title="Dacuronium bromide">Dacuronium bromide</a></li> <li><a href="/wiki/Decamethonium" title="Decamethonium">Decamethonium</a></li> <li><a href="/wiki/Dehydronorketamine" title="Dehydronorketamine">Dehydronorketamine</a></li> <li><a href="/wiki/Desflurane" title="Desflurane">Desflurane</a></li> <li><a href="/wiki/Dextromethorphan" title="Dextromethorphan">Dextromethorphan</a></li> <li><a href="/wiki/Dextropropoxyphene" title="Dextropropoxyphene">Dextropropoxyphene</a></li> <li><a href="/wiki/Dextrorphan" title="Dextrorphan">Dextrorphan</a></li> <li><a href="/w/index.php?title=Diadonium&action=edit&redlink=1" class="new" title="Diadonium (page does not exist)">Diadonium</a></li> <li><a href="/w/index.php?title=Dihydro-beta-erythroidine&action=edit&redlink=1" class="new" title="Dihydro-beta-erythroidine (page does not exist)">DHβE</a></li> <li><a href="/wiki/Dihydrochandonium" title="Dihydrochandonium">Dihydrochandonium</a></li> <li><a href="/wiki/Dimethyltubocurarine" class="mw-redirect" title="Dimethyltubocurarine">Dimethyltubocurarine (metocurine)</a></li> <li><a href="/wiki/Dioscorine" title="Dioscorine">Dioscorine</a></li> <li><a href="/wiki/Dipyrandium" title="Dipyrandium">Dipyrandium</a></li> <li><a href="/wiki/Dizocilpine" title="Dizocilpine">Dizocilpine (MK-801)</a></li> <li><a href="/wiki/Doxacurium" class="mw-redirect" title="Doxacurium">Doxacurium</a></li> <li><a href="/wiki/Encenicline" title="Encenicline">Encenicline</a></li> <li><a href="/wiki/Enflurane" title="Enflurane">Enflurane</a></li> <li><a href="/wiki/Erythravine" title="Erythravine">Erythravine</a></li> <li><a href="/wiki/Esketamine" title="Esketamine">Esketamine</a></li> <li><a href="/wiki/Fazadinium" class="mw-redirect" title="Fazadinium">Fazadinium</a></li> <li><a href="/wiki/Gallamine" class="mw-redirect" title="Gallamine">Gallamine</a></li> <li><a href="/wiki/Gantacurium_chloride" title="Gantacurium chloride">Gantacurium chloride</a></li> <li><a href="/wiki/Halothane" title="Halothane">Halothane</a></li> <li><a href="/wiki/Hexafluronium" class="mw-redirect" title="Hexafluronium">Hexafluronium</a></li> <li><a href="/wiki/Hexamethonium" title="Hexamethonium">Hexamethonium (benzohexonium)</a></li> <li><a href="/wiki/Hydroxybupropion" title="Hydroxybupropion">Hydroxybupropion</a></li> <li><a href="/wiki/Hydroxynorketamine" title="Hydroxynorketamine">Hydroxynorketamine</a></li> <li><a href="/wiki/Ibogaine" title="Ibogaine">Ibogaine</a></li> <li><a href="/wiki/Isoflurane" title="Isoflurane">Isoflurane</a></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/Kynurenic_acid" title="Kynurenic acid">Kynurenic acid</a></li> <li><a href="/wiki/Laudanosine" title="Laudanosine">Laudanosine</a></li> <li><a href="/wiki/Laudexium" class="mw-redirect" title="Laudexium">Laudexium (laudolissin)</a></li> <li><a href="/wiki/Levacetylmethadol" title="Levacetylmethadol">Levacetylmethadol</a></li> <li><a href="/wiki/Levomethadone" title="Levomethadone">Levomethadone</a></li> <li><a href="/wiki/Malouetine" title="Malouetine">Malouetine</a></li> <li><a href="/wiki/2-Methoxyethyl-18-methoxycoronaridinate" title="2-Methoxyethyl-18-methoxycoronaridinate">ME-18-MC</a></li> <li><a href="/wiki/Mecamylamine" title="Mecamylamine">Mecamylamine</a></li> <li><a href="/wiki/Memantine" title="Memantine">Memantine</a></li> <li><a href="/wiki/Methadone" title="Methadone">Methadone</a></li> <li><a href="/wiki/Methorphan" title="Methorphan">Methorphan (racemethorphan)</a></li> <li><a href="/wiki/Methyllycaconitine" title="Methyllycaconitine">Methyllycaconitine</a></li> <li><a href="/wiki/Metocurine" title="Metocurine">Metocurine</a></li> <li><a href="/wiki/Mivacurium" class="mw-redirect" title="Mivacurium">Mivacurium</a></li> <li><a href="/wiki/Morphanol" class="mw-redirect" title="Morphanol">Morphanol (racemorphan)</a></li> <li><a href="/wiki/Neramexane" title="Neramexane">Neramexane</a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li> <li><a href="/wiki/Norketamine" title="Norketamine">Norketamine</a></li> <li><a href="/wiki/Pancuronium_bromide" title="Pancuronium bromide">Pancuronium bromide</a></li> <li><a href="/wiki/Pempidine" title="Pempidine">Pempidine</a></li> <li><a href="/wiki/Pentamine" title="Pentamine">Pentamine</a></li> <li><a href="/wiki/Pentolinium" title="Pentolinium">Pentolinium</a></li> <li><a href="/wiki/Phencyclidine" title="Phencyclidine">Phencyclidine</a></li> <li><a href="/wiki/Pipecuronium_bromide" title="Pipecuronium bromide">Pipecuronium bromide</a></li> <li><a class="mw-selflink selflink">Progesterone</a></li> <li><a href="/wiki/Promegestone" title="Promegestone">Promegestone</a></li> <li><a href="/wiki/Radafaxine" title="Radafaxine">Radafaxine</a></li> <li><a href="/wiki/Rapacuronium_bromide" title="Rapacuronium bromide">Rapacuronium bromide</a></li> <li><a href="/wiki/Reboxetine" title="Reboxetine">Reboxetine</a></li> <li><a href="/wiki/Rocuronium_bromide" title="Rocuronium bromide">Rocuronium bromide</a></li> <li><a href="/wiki/Sevoflurane" title="Sevoflurane">Sevoflurane</a></li> <li><a href="/wiki/Stercuronium_iodide" title="Stercuronium iodide">Stercuronium iodide</a></li> <li><a href="/wiki/Surugatoxin" title="Surugatoxin">Surugatoxin</a></li> <li><a href="/wiki/Thiocolchicoside" title="Thiocolchicoside">Thiocolchicoside</a></li> <li><a href="/wiki/Threohydrobupropion" title="Threohydrobupropion">Threohydrobupropion</a></li> <li><a href="/wiki/Toxiferine" title="Toxiferine">Toxiferine</a></li> <li><a href="/wiki/Tramadol" title="Tramadol">Tramadol</a></li> <li><a href="/wiki/Trimetaphan_camsilate" title="Trimetaphan camsilate">Trimetaphan camsilate (trimethaphan camsylate)</a></li> <li><a href="/w/index.php?title=Tropeinium&action=edit&redlink=1" class="new" title="Tropeinium (page does not exist)">Tropeinium</a></li> <li><a href="/wiki/Tubocurarine" class="mw-redirect" title="Tubocurarine">Tubocurarine</a></li> <li><a href="/wiki/Vanoxerine" title="Vanoxerine">Vanoxerine</a></li> <li><a href="/wiki/Vecuronium_bromide" title="Vecuronium bromide">Vecuronium bromide</a></li> <li><a href="/wiki/Xenon" title="Xenon">Xenon</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/Precursor_(chemistry)" title="Precursor (chemistry)">Precursors</a> (and <a href="/wiki/Prodrug" title="Prodrug">prodrugs</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/Acetyl-coA" class="mw-redirect" title="Acetyl-coA">Acetyl-coA</a></li> <li><a href="/wiki/Adafenoxate" title="Adafenoxate">Adafenoxate</a></li> <li><a href="/wiki/Choline" title="Choline">Choline</a> (<a href="/wiki/Lecithin" title="Lecithin">lecithin</a>)</li> <li><a href="/wiki/Citicoline" title="Citicoline">Citicoline</a></li> <li><a href="/wiki/Cyprodenate" title="Cyprodenate">Cyprodenate</a></li> <li><a href="/wiki/Dimethylethanolamine" title="Dimethylethanolamine">Dimethylethanolamine</a></li> <li><a href="/wiki/Glycerophosphocholine" class="mw-redirect" title="Glycerophosphocholine">Glycerophosphocholine</a></li> <li><a href="/wiki/Meclofenoxate" title="Meclofenoxate">Meclofenoxate (centrophenoxine)</a></li> <li><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">Phosphatidylcholine</a></li> <li><a href="/wiki/Phosphatidylethanolamine" title="Phosphatidylethanolamine">Phosphatidylethanolamine</a></li> <li><a href="/wiki/Phosphorylcholine" title="Phosphorylcholine">Phosphorylcholine</a></li> <li><a href="/wiki/Pirisudanol" title="Pirisudanol">Pirisudanol</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Muscarinic_acetylcholine_receptor_modulators" title="Template:Muscarinic acetylcholine receptor modulators">Muscarinic acetylcholine receptor modulators</a></dd> <dd><a href="/wiki/Template:Acetylcholine_metabolism_and_transport_modulators" title="Template:Acetylcholine metabolism and transport modulators">Acetylcholine metabolism/transport modulators</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="Progesterone_receptor_modulators1654" 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:Progesterone_receptor_modulators" title="Template:Progesterone receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Progesterone_receptor_modulators" title="Template talk:Progesterone receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Progesterone_receptor_modulators" title="Special:EditPage/Template:Progesterone receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Progesterone_receptor_modulators1654" style="font-size:114%;margin:0 4em"><a href="/wiki/Progesterone_receptor" title="Progesterone receptor">Progesterone 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/Progesterone_receptor" title="Progesterone receptor"><abbr title="Progesterone receptor">PR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Progesterone receptor</th><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>Progesterone derivatives: <a href="/wiki/3%CE%B2-Dihydroprogesterone" title="3β-Dihydroprogesterone">3β-Dihydroprogesterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">5α-Dihydroprogesterone</a></li> <li><a href="/wiki/6%CE%B1-Methylprogesterone" title="6α-Methylprogesterone">6α-Methylprogesterone</a></li> <li><a href="/wiki/9%CE%B1-Bromo-11-ketoprogesterone" class="mw-redirect" title="9α-Bromo-11-ketoprogesterone">9α-Bromo-11-ketoprogesterone</a></li> <li><a href="/wiki/11-Dehydroprogesterone" title="11-Dehydroprogesterone">11-Dehydroprogesterone</a></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyprogesterone" title="16α-Hydroxyprogesterone">16α-Hydroxyprogesterone</a></li> <li><a href="/w/index.php?title=17%CE%B1-Methyl-11-deoxycorticosterone_acetate&action=edit&redlink=1" class="new" title="17α-Methyl-11-deoxycorticosterone acetate (page does not exist)">17α-Methyl-11-deoxycorticosterone acetate</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/Dimepregnen" title="Dimepregnen">Dimepregnen</a></li> <li><a href="/wiki/Diosgenin" title="Diosgenin">Diosgenin</a></li> <li><a href="/wiki/P1-185" title="P1-185">P1-185</a></li> <li><a class="mw-selflink selflink">Progesterone</a></li> <li><a href="/wiki/Progesterone_3-acetyl_enol_ether" title="Progesterone 3-acetyl enol ether">Progesterone 3-acetyl enol ether</a></li> <li><a href="/wiki/Quingestrone" title="Quingestrone">Quingestrone</a></li></ul> <ul><li>Retroprogesterone derivatives: <a href="/wiki/20%CE%B1-Dihydrodydrogesterone" title="20α-Dihydrodydrogesterone">20α-Dihydrodydrogesterone</a></li> <li><a href="/wiki/20%CE%B1-Dihydrotrengestone" title="20α-Dihydrotrengestone">20α-Dihydrotrengestone</a></li> <li><a href="/wiki/DU-41164" title="DU-41164">DU-41164</a></li> <li><a href="/wiki/DU-41165" title="DU-41165">DU-41165</a></li> <li><a href="/wiki/Dydrogesterone" title="Dydrogesterone">Dydrogesterone</a></li> <li><a href="/wiki/Retroprogesterone" title="Retroprogesterone">Retroprogesterone</a></li> <li><a href="/wiki/Ro_6-3129" title="Ro 6-3129">Ro 6-3129</a></li> <li><a href="/wiki/Trengestone" title="Trengestone">Trengestone</a></li></ul> <ul><li>17α-Substituted progesterone derivatives: <a href="/wiki/6%CE%B1-Methyl-17%CE%B1-bromoprogesterone" title="6α-Methyl-17α-bromoprogesterone">6α-Methyl-17α-bromoprogesterone</a></li> <li><a href="/wiki/15%CE%B2-Hydroxycyproterone_acetate" title="15β-Hydroxycyproterone acetate">15β-Hydroxycyproterone acetate</a></li> <li><a href="/wiki/16-Methylene-17%CE%B1-hydroxyprogesterone_acetate" title="16-Methylene-17α-hydroxyprogesterone acetate">16-Methylene-17α-hydroxyprogesterone acetate</a></li> <li><a href="/wiki/17%CE%B1-Bromoprogesterone" title="17α-Bromoprogesterone">17α-Bromoprogesterone</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone (hydroxyprogesterone)</a></li> <li><a href="/wiki/17%CE%B1-Methylprogesterone" title="17α-Methylprogesterone">17α-Methylprogesterone</a></li> <li><a href="/wiki/Acetomepregenol" title="Acetomepregenol">Acetomepregenol (mepregenol diacetate)</a></li> <li><a href="/wiki/Algestone" title="Algestone">Algestone</a></li> <li><a href="/wiki/Algestone_acetonide" title="Algestone acetonide">Algestone acetonide</a></li> <li><a href="/wiki/Algestone_acetophenide" title="Algestone acetophenide">Algestone acetophenide</a></li> <li><a href="/wiki/Anagestone" title="Anagestone">Anagestone</a></li> <li><a href="/wiki/Anagestone_acetate" title="Anagestone acetate">Anagestone acetate</a></li> <li><a href="/w/index.php?title=Bromethenmadinone&action=edit&redlink=1" class="new" title="Bromethenmadinone (page does not exist)">Bromethenmadinone</a></li> <li><a href="/wiki/Bromethenmadinone_acetate" title="Bromethenmadinone acetate">Bromethenmadinone acetate</a></li> <li><a href="/wiki/Butagest" title="Butagest">Butagest (buterol)</a></li> <li><a href="/wiki/Chlormadinone" title="Chlormadinone">Chlormadinone</a></li> <li><a href="/wiki/Chlormadinone_acetate" title="Chlormadinone acetate">Chlormadinone acetate</a></li> <li><a href="/wiki/Chlormadinone_caproate" title="Chlormadinone caproate">Chlormadinone caproate</a></li> <li><a href="/w/index.php?title=Chlormethenmadinone&action=edit&redlink=1" class="new" title="Chlormethenmadinone (page does not exist)">Chlormethenmadinone</a></li> <li><a href="/wiki/Chlormethenmadinone_acetate" title="Chlormethenmadinone acetate">Chlormethenmadinone acetate</a></li> <li><a href="/wiki/Cismadinone" title="Cismadinone">Cismadinone</a></li> <li><a href="/wiki/Cismadinone_acetate" title="Cismadinone acetate">Cismadinone acetate</a></li> <li><a href="/wiki/Clogestone" title="Clogestone">Clogestone</a></li> <li><a href="/wiki/Clogestone_acetate" title="Clogestone acetate">Clogestone acetate</a></li> <li><a href="/wiki/Clomegestone" title="Clomegestone">Clomegestone</a></li> <li><a href="/wiki/Clomegestone_acetate" title="Clomegestone acetate">Clomegestone acetate</a></li> <li><a href="/wiki/Cymegesolate" title="Cymegesolate">Cymegesolate</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Delmadinone" title="Delmadinone">Delmadinone</a></li> <li><a href="/wiki/Delmadinone_acetate" title="Delmadinone acetate">Delmadinone acetate</a></li> <li><a href="/wiki/Edogestrone" title="Edogestrone">Edogestrone</a></li> <li><a href="/wiki/Flugestone" title="Flugestone">Flugestone</a></li> <li><a href="/wiki/Flugestone_acetate" title="Flugestone acetate">Flugestone acetate</a></li> <li><a href="/wiki/Fluorometholone" title="Fluorometholone">Fluorometholone</a></li> <li><a href="/wiki/Fluorometholone_acetate" title="Fluorometholone acetate">Fluorometholone acetate</a></li> <li><a href="/wiki/Flumedroxone" title="Flumedroxone">Flumedroxone</a></li> <li><a href="/wiki/Flumedroxone_acetate" title="Flumedroxone acetate">Flumedroxone acetate</a></li> <li><a href="/wiki/Fluoromedroxyprogesterone_acetate" title="Fluoromedroxyprogesterone acetate">Fluoromedroxyprogesterone acetate</a></li> <li><a href="/wiki/Gestaclone" title="Gestaclone">Gestaclone</a></li> <li><a href="/w/index.php?title=Gestobutanoyl&action=edit&redlink=1" class="new" title="Gestobutanoyl (page does not exist)">Gestobutanoyl</a></li> <li><a href="/wiki/Haloprogesterone" title="Haloprogesterone">Haloprogesterone</a></li> <li><a href="/wiki/Hydromadinone" title="Hydromadinone">Hydromadinone</a></li> <li><a href="/wiki/Hydromadinone_acetate" title="Hydromadinone acetate">Hydromadinone acetate</a></li> <li><a href="/wiki/Hydroxyprogesterone_acetate" title="Hydroxyprogesterone acetate">Hydroxyprogesterone acetate</a></li> <li><a href="/wiki/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">Hydroxyprogesterone caproate (hydroxyprogesterone hexanoate)</a></li> <li><a href="/wiki/Hydroxyprogesterone_heptanoate" title="Hydroxyprogesterone heptanoate">Hydroxyprogesterone heptanoate (hydroxyprogesterone enanthate)</a></li> <li><a href="/wiki/Hydroxyprogesterone_heptanoate_benzilic_acid_hydrazone" title="Hydroxyprogesterone heptanoate benzilic acid hydrazone">Hydroxyprogesterone heptanoate benzilic acid hydrazone</a></li> <li><a href="/wiki/Mecigestone" title="Mecigestone">Mecigestone (pentarane B)</a></li> <li><a href="/wiki/Medrogestone" title="Medrogestone">Medrogestone</a></li> <li><a href="/wiki/Medroxyprogesterone" title="Medroxyprogesterone">Medroxyprogesterone</a></li> <li><a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">Medroxyprogesterone acetate</a></li> <li><a href="/wiki/Medroxyprogesterone_caproate" title="Medroxyprogesterone caproate">Medroxyprogesterone caproate</a></li> <li><a href="/wiki/Megestrol" title="Megestrol">Megestrol</a></li> <li><a href="/wiki/Megestrol_acetate" title="Megestrol acetate">Megestrol acetate</a></li> <li><a href="/wiki/Megestrol_caproate" title="Megestrol caproate">Megestrol caproate</a></li> <li><a href="/wiki/Melengestrol" title="Melengestrol">Melengestrol</a></li> <li><a href="/wiki/Melengestrol_acetate" title="Melengestrol acetate">Melengestrol acetate</a></li> <li><a href="/wiki/Methenmadinone" title="Methenmadinone">Methenmadinone</a></li> <li><a href="/wiki/Methenmadinone_acetate" title="Methenmadinone acetate">Methenmadinone acetate</a></li> <li><a href="/wiki/Methenmadinone_caproate" title="Methenmadinone caproate">Methenmadinone caproate</a></li> <li><a href="/wiki/Mometasone" title="Mometasone">Mometasone</a></li> <li><a href="/wiki/Mometasone_furoate" class="mw-redirect" title="Mometasone furoate">Mometasone furoate</a></li> <li><a href="/wiki/Osaterone" title="Osaterone">Osaterone</a></li> <li><a href="/wiki/Osaterone_acetate" title="Osaterone acetate">Osaterone acetate</a></li> <li><a href="/wiki/Pentagestrone" title="Pentagestrone">Pentagestrone</a></li> <li><a href="/wiki/Pentagestrone_acetate" title="Pentagestrone acetate">Pentagestrone acetate</a></li> <li><a href="/wiki/Pentarane_A" title="Pentarane A">Pentarane A</a></li> <li><a href="/wiki/Proligestone" title="Proligestone">Proligestone</a></li> <li><a href="/wiki/Triamcinolone_acetonide" title="Triamcinolone acetonide">Triamcinolone acetonide</a></li></ul> <ul><li>19-Norprogesterone derivatives: <a href="/wiki/17%CE%B1-Methyl-19-norprogesterone" title="17α-Methyl-19-norprogesterone">17α-Methyl-19-norprogesterone</a></li> <li><a href="/wiki/18-Methylsegesterone_acetate" title="18-Methylsegesterone acetate">18-Methylsegesterone acetate</a></li> <li><a href="/wiki/19-Norprogesterone" title="19-Norprogesterone">19-Norprogesterone</a></li> <li><a href="/wiki/Amadinone" title="Amadinone">Amadinone</a></li> <li><a href="/wiki/Amadinone_acetate" title="Amadinone acetate">Amadinone acetate</a></li> <li><a href="/wiki/Demegestone" title="Demegestone">Demegestone</a></li> <li><a href="/w/index.php?title=Fluoro_ethyl_norprogesterone&action=edit&redlink=1" class="new" title="Fluoro ethyl norprogesterone (page does not exist)">Fluoro ethyl norprogesterone</a></li> <li><a href="/w/index.php?title=Fluoro_furanyl_norprogesterone&action=edit&redlink=1" class="new" title="Fluoro furanyl norprogesterone (page does not exist)">Fluoro furanyl norprogesterone</a></li> <li><a href="/wiki/Gestadienol" title="Gestadienol">Gestadienol</a></li> <li><a href="/wiki/Gestadienol_acetate" title="Gestadienol acetate">Gestadienol acetate</a></li> <li><a href="/wiki/Gestonorone_acetate" title="Gestonorone acetate">Gestonorone acetate (gestronol acetate)</a></li> <li><a href="/wiki/Gestonorone_caproate" title="Gestonorone caproate">Gestonorone caproate (gestronol hexanoate)</a></li> <li><a href="/wiki/Gestronol" title="Gestronol">Gestronol (gestonorone)</a></li> <li><a href="/wiki/Nomegestrol" title="Nomegestrol">Nomegestrol</a></li> <li><a href="/wiki/Nomegestrol_acetate" title="Nomegestrol acetate">Nomegestrol acetate</a></li> <li><a href="/wiki/Norgestomet" title="Norgestomet">Norgestomet</a></li> <li><a href="/wiki/ORG-2058" title="ORG-2058">ORG-2058</a></li> <li><a href="/wiki/Oxogestone" title="Oxogestone">Oxogestone</a></li> <li><a href="/wiki/Oxogestone_phenpropionate" title="Oxogestone phenpropionate">Oxogestone phenpropionate (xinogestone)</a></li> <li><a href="/wiki/Promegestone" title="Promegestone">Promegestone</a></li> <li><a href="/wiki/Segesterone" title="Segesterone">Segesterone</a></li> <li><a href="/wiki/Nestorone" class="mw-redirect" title="Nestorone">Segesterone acetate (nestorone)</a></li> <li><a href="/wiki/Trimegestone" title="Trimegestone">Trimegestone</a></li></ul> <ul><li>Testosterone derivatives: Progestins: <a href="/wiki/6,6-Difluoronorethisterone" title="6,6-Difluoronorethisterone">6,6-Difluoronorethisterone</a></li> <li><a href="/wiki/6,6-Difluoronorethisterone_acetate" title="6,6-Difluoronorethisterone acetate">6,6-Difluoronorethisterone acetate</a></li> <li><a href="/wiki/17%CE%B1-Allyl-19-nortestosterone" title="17α-Allyl-19-nortestosterone">17α-Allyl-19-nortestosterone</a></li> <li><a href="/wiki/Allylestrenol" title="Allylestrenol">Allylestrenol</a></li> <li><a href="/wiki/Altrenogest" title="Altrenogest">Altrenogest</a></li> <li><a href="/wiki/Chloroethynylnorgestrel" title="Chloroethynylnorgestrel">Chloroethynylnorgestrel</a></li> <li><a href="/wiki/Cingestol" title="Cingestol">Cingestol</a></li> <li><a href="/wiki/Danazol" title="Danazol">Danazol</a></li> <li><a href="/wiki/Desogestrel" title="Desogestrel">Desogestrel</a></li> <li><a href="/wiki/Dienogest" title="Dienogest">Dienogest</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/Ethisterone" title="Ethisterone">Ethisterone</a></li> <li><a href="/wiki/Ethynerone" title="Ethynerone">Ethynerone</a></li> <li><a href="/wiki/Etonogestrel" title="Etonogestrel">Etonogestrel</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/Gestodene" title="Gestodene">Gestodene</a></li> <li><a href="/wiki/Gestrinone" title="Gestrinone">Gestrinone</a></li> <li><a href="/wiki/Levonorgestrel" title="Levonorgestrel">Levonorgestrel</a></li> <li><a href="/wiki/Levonorgestrel_ester" class="mw-redirect" title="Levonorgestrel ester">Levonorgestrel esters</a> (e.g., <a href="/wiki/Levonorgestrel_butanoate" title="Levonorgestrel butanoate">levonorgestrel butanoate</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/Metynodiol" title="Metynodiol">Metynodiol</a></li> <li><a href="/wiki/Metynodiol_diacetate" title="Metynodiol diacetate">Metynodiol diacetate</a></li> <li><a href="/wiki/Norelgestromin" title="Norelgestromin">Norelgestromin</a></li> <li><a href="/wiki/Norethisterone" title="Norethisterone">Norethisterone (norethindrone)</a></li> <li><a href="/wiki/Norethisterone_ester" class="mw-redirect" title="Norethisterone ester">Norethisterone esters</a> (e.g., <a href="/wiki/Norethisterone_acetate" title="Norethisterone acetate">norethisterone acetate</a>, <a href="/wiki/Norethisterone_enanthate" title="Norethisterone enanthate">norethisterone enanthate</a>)</li> <li><a href="/wiki/Noretynodrel" title="Noretynodrel">Noretynodrel</a></li> <li><a href="/wiki/Norgesterone" title="Norgesterone">Norgesterone</a></li> <li><a href="/wiki/Norgestimate" title="Norgestimate">Norgestimate</a></li> <li><a href="/wiki/Norgestrel" title="Norgestrel">Norgestrel</a></li> <li><a href="/wiki/Norgestrienone" title="Norgestrienone">Norgestrienone</a></li> <li><a href="/wiki/Norvinisterone" title="Norvinisterone">Norvinisterone</a></li> <li><a href="/wiki/Oxendolone" title="Oxendolone">Oxendolone</a></li> <li><a href="/wiki/Quingestanol" title="Quingestanol">Quingestanol</a></li> <li><a href="/wiki/Quingestanol_acetate" title="Quingestanol acetate">Quingestanol acetate</a></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li> <li><a href="/wiki/Tigestol" title="Tigestol">Tigestol</a></li> <li><a href="/wiki/Tosagestin" title="Tosagestin">Tosagestin</a>; Anabolic–androgenic steroids: <a href="/wiki/11%CE%B2-Methyl-19-nortestosterone" title="11β-Methyl-19-nortestosterone">11β-Methyl-19-nortestosterone</a></li> <li><a href="/wiki/11%CE%B2-Methyl-19-nortestosterone_dodecylcarbonate" title="11β-Methyl-19-nortestosterone dodecylcarbonate">11β-Methyl-19-nortestosterone dodecylcarbonate</a></li> <li><a href="/wiki/19-Nor-5-androstenediol" title="19-Nor-5-androstenediol">19-Nor-5-androstenediol</a></li> <li><a href="/wiki/19-Nor-5-androstenedione" title="19-Nor-5-androstenedione">19-Nor-5-androstenedione</a></li> <li><a href="/wiki/19-Nordehydroepiandrosterone" title="19-Nordehydroepiandrosterone">19-Nordehydroepiandrosterone</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/Bolandione" title="Bolandione">Bolandione</a></li> <li><a href="/wiki/Dimethisterone" title="Dimethisterone">Dimethisterone</a></li> <li><a href="/wiki/Dienedione" title="Dienedione">Dienedione</a></li> <li><a href="/wiki/Dienolone" title="Dienolone">Dienolone</a></li> <li><a href="/wiki/Dimethandrolone" title="Dimethandrolone">Dimethandrolone</a></li> <li><a href="/wiki/Dimethandrolone_buciclate" title="Dimethandrolone buciclate">Dimethandrolone buciclate</a></li> <li><a href="/wiki/Dimethandrolone_dodecylcarbonate" title="Dimethandrolone dodecylcarbonate">Dimethandrolone dodecylcarbonate</a></li> <li><a href="/wiki/Dimethandrolone_undecanoate" title="Dimethandrolone undecanoate">Dimethandrolone undecanoate</a></li> <li><a href="/wiki/Dimethyldienolone" title="Dimethyldienolone">Dimethyldienolone</a></li> <li><a href="/wiki/Dimethyltrienolone" title="Dimethyltrienolone">Dimethyltrienolone</a></li> <li><a href="/wiki/Ethyldienolone" title="Ethyldienolone">Ethyldienolone</a></li> <li><a href="/wiki/Ethylestrenol" title="Ethylestrenol">Ethylestrenol (ethylnandrol)</a></li> <li><a href="/wiki/Methyldienolone" title="Methyldienolone">Methyldienolone</a></li> <li><a href="/wiki/Metribolone" title="Metribolone">Metribolone (R-1881)</a></li> <li><a href="/wiki/Methoxydienone" title="Methoxydienone">Methoxydienone (methoxygonadiene)</a></li> <li><a href="/wiki/Mibolerone" title="Mibolerone">Mibolerone</a></li> <li><a href="/wiki/Nandrolone" title="Nandrolone">Nandrolone</a></li> <li><a href="/wiki/Nandrolone_ester" class="mw-redirect" title="Nandrolone ester">Nandrolone esters</a> (e.g., <a href="/wiki/Nandrolone_decanoate" title="Nandrolone decanoate">nandrolone decanoate</a>, <a href="/wiki/Nandrolone_phenylpropionate" title="Nandrolone phenylpropionate">nandrolone phenylpropionate</a>)</li> <li><a href="/wiki/Norethandrolone" title="Norethandrolone">Norethandrolone</a></li> <li><a href="/wiki/Normethandrone" title="Normethandrone">Normethandrone (methylestrenolone, normethandrolone, normethisterone)</a></li> <li><a href="/wiki/RU-2309" title="RU-2309">RU-2309</a></li> <li><a href="/wiki/Tetrahydrogestrinone" title="Tetrahydrogestrinone">Tetrahydrogestrinone</a></li> <li><a href="/wiki/Trenbolone" title="Trenbolone">Trenbolone (trienolone)</a></li> <li><a href="/wiki/Trenbolone_ester" class="mw-redirect" title="Trenbolone ester">Trenbolone esters</a> (e.g., <a href="/wiki/Trenbolone_acetate" title="Trenbolone acetate">trenbolone acetate</a>, <a href="/wiki/Trenbolone_enanthate" title="Trenbolone enanthate">trenbolone enanthate</a>)</li> <li><a href="/wiki/Trendione" title="Trendione">Trendione</a></li> <li><a href="/wiki/Trestolone" title="Trestolone">Trestolone</a></li> <li><a href="/wiki/Trestolone_acetate" title="Trestolone acetate">Trestolone acetate</a></li></ul> <ul><li>Spirolactone derivatives: <a href="/wiki/Canrenoic_acid" title="Canrenoic acid">Canrenoic acid</a></li> <li><a href="/wiki/Canrenone" title="Canrenone">Canrenone</a></li> <li><a href="/wiki/Drospirenone" title="Drospirenone">Drospirenone</a></li> <li><a href="/wiki/Mespirenone" title="Mespirenone">Mespirenone</a></li> <li><a href="/wiki/Potassium_canrenoate" title="Potassium canrenoate">Potassium canrenoate</a></li> <li><a href="/wiki/Prorenone" title="Prorenone">Prorenone</a></li> <li><a href="/wiki/SC-5233" title="SC-5233">SC-5233 (spirolactone)</a></li> <li><a href="/wiki/SC-8109" title="SC-8109">SC-8109</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/wiki/Spirorenone" title="Spirorenone">Spirorenone</a></li></ul> <ul><li>Nonsteroidal: <a href="/wiki/3,8-Dihydrodiligustilide" title="3,8-Dihydrodiligustilide">3,8-Dihydrodiligustilide</a></li> <li><a href="/wiki/LG-2527" title="LG-2527">LG-2527</a></li> <li><a href="/w/index.php?title=LG-100128&action=edit&redlink=1" class="new" title="LG-100128 (page does not exist)">LG-100128</a></li> <li><a href="/wiki/Riligustilide" title="Riligustilide">Riligustilide</a></li> <li><a href="/w/index.php?title=RWJ-26819&action=edit&redlink=1" class="new" title="RWJ-26819 (page does not exist)">RWJ-26819</a></li> <li><a href="/w/index.php?title=RWJ-49853&action=edit&redlink=1" class="new" title="RWJ-49853 (page does not exist)">RWJ-49853</a></li> <li><a href="/w/index.php?title=RWJ-60130&action=edit&redlink=1" class="new" title="RWJ-60130 (page does not exist)">RWJ-60130</a></li> <li><a href="/wiki/Tanaproget" title="Tanaproget">Tanaproget</a></li> <li><a href="/wiki/ZM-182345" title="ZM-182345">ZM-182345</a></li></ul> <ul><li>Unknown: <a href="/wiki/ORG-47241" title="ORG-47241">ORG-47241</a></li> <li><a href="/wiki/ORG-201745" title="ORG-201745">ORG-201745</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Mixed (<a href="/wiki/Selective_progesterone_receptor_modulators" class="mw-redirect" title="Selective progesterone receptor modulators"><abbr title="Selective progesterone receptor modulators">SPRMs</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 progesterone receptor modulators)</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Steroidal: <a href="/wiki/Dihydroethisterone" class="mw-redirect" title="Dihydroethisterone">Dihydroethisterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydrolevonorgestrel" title="5α-Dihydrolevonorgestrel">5α-Dihydrolevonorgestrel</a></li> <li><a href="/wiki/5%CE%B1-Dihydronorethisterone" title="5α-Dihydronorethisterone">5α-Dihydronorethisterone</a></li> <li><a href="/wiki/Asoprisnil" title="Asoprisnil">Asoprisnil</a></li> <li><a href="/wiki/Asoprisnil_ecamate" title="Asoprisnil ecamate">Asoprisnil ecamate</a></li> <li><a href="/wiki/Guggulsterone" title="Guggulsterone">Guggulsterone</a></li> <li><a href="/w/index.php?title=J1042&action=edit&redlink=1" class="new" title="J1042 (page does not exist)">J1042</a></li> <li><a href="/w/index.php?title=LG-120838&action=edit&redlink=1" class="new" title="LG-120838 (page does not exist)">LG-120838</a></li> <li><a href="/wiki/Metapristone" title="Metapristone">Metapristone (RU-42633)</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone (RU-486)</a></li> <li><a href="/w/index.php?title=ORF-9371&action=edit&redlink=1" class="new" title="ORF-9371 (page does not exist)">ORF-9371</a></li> <li><a href="/wiki/ORF-9326" class="mw-redirect" title="ORF-9326">ORF-9326</a></li> <li><a href="/w/index.php?title=ORG-31710&action=edit&redlink=1" class="new" title="ORG-31710 (page does not exist)">ORG-31710</a></li> <li><a href="/w/index.php?title=ORG-33628&action=edit&redlink=1" class="new" title="ORG-33628 (page does not exist)">ORG-33628</a></li> <li><a href="/w/index.php?title=RMI-12936&action=edit&redlink=1" class="new" title="RMI-12936 (page does not exist)">RMI-12936</a></li> <li><a href="/wiki/Telapristone" title="Telapristone">Telapristone</a></li> <li><a href="/wiki/Ulipristal_acetate" title="Ulipristal acetate">Ulipristal acetate</a></li> <li><a href="/wiki/Vilaprisan" title="Vilaprisan">Vilaprisan</a></li> <li><a href="/w/index.php?title=ZK-137316&action=edit&redlink=1" class="new" title="ZK-137316 (page does not exist)">ZK-137316</a></li></ul> <ul><li>Nonsteroidal: <a href="/wiki/Apigenin" title="Apigenin">Apigenin</a></li> <li><a href="/wiki/Kaempferol" title="Kaempferol">Kaempferol</a></li> <li><a href="/w/index.php?title=LG-120920&action=edit&redlink=1" class="new" title="LG-120920 (page does not exist)">LG-120920</a></li> <li><a href="/wiki/Naringenin" title="Naringenin">Naringenin</a></li> <li><a href="/w/index.php?title=PRA-910&action=edit&redlink=1" class="new" title="PRA-910 (page does not exist)">PRA-910</a></li> <li><a href="/wiki/Syringic_acid" title="Syringic acid">Syringic acid</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>Steroidal: <a href="/wiki/Aglepristone" title="Aglepristone">Aglepristone</a></li> <li><a href="/wiki/Lilopristone" title="Lilopristone">Lilopristone</a></li> <li><a href="/wiki/Lonaprisan" title="Lonaprisan">Lonaprisan</a></li> <li><a href="/wiki/Onapristone" title="Onapristone">Onapristone</a></li> <li><a href="/w/index.php?title=ORG-31710&action=edit&redlink=1" class="new" title="ORG-31710 (page does not exist)">ORG-31710</a></li> <li><a href="/w/index.php?title=ORG-31806&action=edit&redlink=1" class="new" title="ORG-31806 (page does not exist)">ORG-31806</a></li> <li><a href="/w/index.php?title=ORG-33628&action=edit&redlink=1" class="new" title="ORG-33628 (page does not exist)">ORG-33628</a></li> <li><a href="/w/index.php?title=RTI_3021%E2%80%93022&action=edit&redlink=1" class="new" title="RTI 3021–022 (page does not exist)">RTI 3021–022</a></li> <li><a href="/wiki/Toripristone" title="Toripristone">Toripristone</a></li> <li><a href="/wiki/Zanoterone" title="Zanoterone">Zanoterone</a></li></ul> <ul><li>Nonsteroidal: <a href="/wiki/Darolutamide" title="Darolutamide">Darolutamide</a></li> <li><a href="/w/index.php?title=LG-001447&action=edit&redlink=1" class="new" title="LG-001447 (page does not exist)">LG-001447</a></li> <li><a href="/w/index.php?title=LG-100127&action=edit&redlink=1" class="new" title="LG-100127 (page does not exist)">LG-100127</a></li> <li><a href="/w/index.php?title=LG-100128&action=edit&redlink=1" class="new" title="LG-100128 (page does not exist)">LG-100128</a></li> <li><a href="/w/index.php?title=LG-120830&action=edit&redlink=1" class="new" title="LG-120830 (page does not exist)">LG-120830</a></li> <li><a href="/w/index.php?title=LG-121046&action=edit&redlink=1" class="new" title="LG-121046 (page does not exist)">LG-121046</a></li> <li><a href="/wiki/Valproic_acid" class="mw-redirect" title="Valproic acid">Valproic acid</a></li> <li><a href="/w/index.php?title=ZM-150271&action=edit&redlink=1" class="new" title="ZM-150271 (page does not exist)">ZM-150271</a></li> <li><a href="/w/index.php?title=ZM-172406&action=edit&redlink=1" class="new" title="ZM-172406 (page does not exist)">ZM-172406</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/Membrane_progesterone_receptor" title="Membrane progesterone receptor"><abbr title="Membrane progesterone receptor">mPR</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 Membrane progesterone receptor (<a href="/wiki/Progestin_and_adipoQ_receptor" title="Progestin and adipoQ receptor"><abbr title="Progestin and adipoQ receptor">PAQR</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 Progestin and adipoQ receptor)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/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/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycortisone (21-hydroxyprogesterone)</a></li> <li><a href="/wiki/11-Deoxycortisol" title="11-Deoxycortisol">11-Deoxycortisol (17α,21-dihydroxyprogesterone)</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone</a></li> <li><a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a></li> <li><a class="mw-selflink selflink">Progesterone</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/Mifepristone" title="Mifepristone">Mifepristone</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:Progestogens_and_antiprogestogens" title="Template:Progestogens and antiprogestogens">Progestogens and antiprogestogens</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:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators">Estrogen receptor modulators</a></dd> <dd><a href="/wiki/List_of_steroidal_progestogens" class="mw-redirect" title="List of steroidal progestogens">List of progestogens</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="Sigma_receptor_modulators212" 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:Sigma_receptor_modulators" title="Template:Sigma receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Sigma_receptor_modulators" title="Template talk:Sigma receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Sigma_receptor_modulators" title="Special:EditPage/Template:Sigma receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Sigma_receptor_modulators212" style="font-size:114%;margin:0 4em"><a href="/wiki/Sigma_receptor" title="Sigma receptor">Sigma 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/Sigma-1_receptor" title="Sigma-1 receptor">σ1</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>Agonists: <a href="/wiki/3-PPP" title="3-PPP">3-PPP</a></li> <li><a href="/wiki/4-PPBP" title="4-PPBP">4-PPBP</a></li> <li><a href="/wiki/5-MeO-DMT" title="5-MeO-DMT">5-MeO-DMT</a></li> <li><a href="/wiki/Alazocine" title="Alazocine">Alazocine (SKF-10047)</a></li> <li><a href="/wiki/Amantadine" title="Amantadine">Amantadine</a></li> <li><a href="/wiki/Arketamine" title="Arketamine">Arketamine</a></li> <li><a href="/w/index.php?title=BD-737&action=edit&redlink=1" class="new" title="BD-737 (page does not exist)">BD-737</a></li> <li><a href="/wiki/BD-1052" class="mw-redirect" title="BD-1052">BD-1052</a></li> <li><a href="/wiki/Blarcamesine" title="Blarcamesine">Blarcamesine</a></li> <li><a href="/wiki/Captodiame" title="Captodiame">Captodiame</a></li> <li><a href="/wiki/Citalopram" title="Citalopram">Citalopram</a></li> <li><a href="/wiki/Calcitonin_gene-related_peptide" title="Calcitonin gene-related peptide"><abbr title="Calcitonin gene-related peptide">CGRP</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 Calcitonin gene-related peptide</li> <li><a href="/wiki/Cloperastine" title="Cloperastine">Cloperastine</a></li> <li><a href="/wiki/Cocaine" title="Cocaine">Cocaine</a></li> <li><a href="/wiki/Cutamesine" title="Cutamesine">Cutamesine (SA-4503)</a></li> <li><a href="/wiki/Cyclazocine" title="Cyclazocine">Cyclazocine</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">Dehydroepiandrosterone (DHEA)</a> (<a href="/wiki/Prasterone" title="Prasterone">prasterone</a>)</li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">Dehydroepiandrosterone sulfate (DHEA-S)</a> (<a href="/wiki/Prasterone_sulfate" title="Prasterone sulfate">prasterone sulfate</a>)</li> <li><a href="/wiki/Dextrallorphan" title="Dextrallorphan">Dextrallorphan</a></li> <li><a href="/wiki/Dextromethorphan" title="Dextromethorphan">Dextromethorphan (DXM)</a></li> <li><a href="/wiki/Dextrorphan" title="Dextrorphan">Dextrorphan (DXO)</a></li> <li><a href="/wiki/Dimemorfan" title="Dimemorfan">Dimemorfan</a></li> <li><a href="/wiki/Dimethyltryptamine" class="mw-redirect" title="Dimethyltryptamine">Dimethyltryptamine (DMT)</a></li> <li><a href="/wiki/Ditolylguanidine" title="Ditolylguanidine">Ditolylguanidine (DTG)</a></li> <li><a href="/wiki/Donepezil" title="Donepezil">Donepezil</a></li> <li><a href="/wiki/Eliprodil" title="Eliprodil">Eliprodil</a></li> <li><a href="/wiki/Escitalopram" title="Escitalopram">Escitalopram</a></li> <li><a href="/wiki/Fabomotizole" title="Fabomotizole">Fabomotizole (afobazole)</a></li> <li><a href="/wiki/Fluoxetine" title="Fluoxetine">Fluoxetine</a></li> <li><a href="/wiki/Fluvoxamine" title="Fluvoxamine">Fluvoxamine</a></li> <li><a href="/wiki/Ifenprodil" title="Ifenprodil">Ifenprodil</a></li> <li><a href="/wiki/Igmesine" title="Igmesine">Igmesine (JO-1784)</a></li> <li><a href="/w/index.php?title=IPAB_(drug)&action=edit&redlink=1" class="new" title="IPAB (drug) (page does not exist)">IPAB</a></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/L-687384" class="mw-redirect" title="L-687384">L-687384</a></li> <li><a href="/wiki/MDMA" title="MDMA"><abbr title="Methylenedioxymethamphetamine">MDMA</abbr> (midomafetamine)</a></li> <li><a href="/wiki/Memantine" title="Memantine">Memantine</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a></li> <li><a href="/wiki/Methoxetamine" title="Methoxetamine">Methoxetamine</a></li> <li><a href="/wiki/Methylphenidate" title="Methylphenidate">Methylphenidate</a></li> <li><a href="/wiki/Nepinalone" title="Nepinalone">Nepinalone</a></li> <li><a href="/wiki/Neuropeptide_Y" title="Neuropeptide Y">Neuropeptide Y</a></li> <li><a href="/wiki/Noscapine" title="Noscapine">Noscapine</a></li> <li><a href="/w/index.php?title=OPC-14523&action=edit&redlink=1" class="new" title="OPC-14523 (page does not exist)">OPC-14523</a></li> <li><a href="/wiki/Opipramol" title="Opipramol">Opipramol</a></li> <li><a href="/wiki/Pentazocine" title="Pentazocine">Pentazocine</a></li> <li><a href="/wiki/Pentoxyverine" title="Pentoxyverine">Pentoxyverine (carbetapentane)</a></li> <li><a href="/wiki/PRE-084" title="PRE-084">PRE-084</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/Pridopidine" title="Pridopidine">Pridopidine</a></li> <li><a href="/wiki/Racemethorphan" class="mw-redirect" title="Racemethorphan">Racemethorphan (methorphan)</a></li> <li><a href="/wiki/Racemorphan" title="Racemorphan">Racemorphan (morphanol)</a></li> <li><a href="/w/index.php?title=UMB-23&action=edit&redlink=1" class="new" title="UMB-23 (page does not exist)">UMB-23</a></li> <li><a href="/w/index.php?title=UMB-82&action=edit&redlink=1" class="new" title="UMB-82 (page does not exist)">UMB-82</a></li></ul> <ul><li>Antagonists: <a href="/wiki/3-PPP" title="3-PPP">3-PPP</a></li> <li><a href="/wiki/AC-927" class="mw-redirect" title="AC-927">AC-927</a></li> <li><a href="/wiki/BD-1008" class="mw-redirect" title="BD-1008">BD-1008</a></li> <li><a href="/wiki/BD-1031" class="mw-redirect" title="BD-1031">BD-1031</a></li> <li><a href="/wiki/BD-1047" title="BD-1047">BD-1047</a></li> <li><a href="/wiki/BD-1060" class="mw-redirect" title="BD-1060">BD-1060</a></li> <li><a href="/wiki/BD-1063" class="mw-redirect" title="BD-1063">BD-1063</a></li> <li><a href="/wiki/BD-1067" class="mw-redirect" title="BD-1067">BD-1067</a></li> <li><a href="/wiki/BMY-14802" title="BMY-14802">BMY-14802 (BMS-181100)</a></li> <li><a href="/wiki/CM-156" class="mw-redirect" title="CM-156">CM-156</a></li> <li><a href="/w/index.php?title=Dup-734&action=edit&redlink=1" class="new" title="Dup-734 (page does not exist)">Dup-734</a></li> <li><a href="/w/index.php?title=E-5842&action=edit&redlink=1" class="new" title="E-5842 (page does not exist)">E-5842</a></li> <li><a href="/wiki/E-52862" title="E-52862">E-52862 (S1RA)</a></li> <li><a href="/wiki/Haloperidol" title="Haloperidol">Haloperidol</a></li> <li><a href="/w/index.php?title=LR-132&action=edit&redlink=1" class="new" title="LR-132 (page does not exist)">LR-132</a></li> <li><a href="/w/index.php?title=LR-172&action=edit&redlink=1" class="new" title="LR-172 (page does not exist)">LR-172</a></li> <li><a href="/wiki/MS-377" title="MS-377">MS-377</a></li> <li><a href="/wiki/NE-100" title="NE-100">NE-100</a></li> <li><a href="/w/index.php?title=NPC-16377&action=edit&redlink=1" class="new" title="NPC-16377 (page does not exist)">NPC-16377</a></li> <li><a href="/wiki/Panamesine" title="Panamesine">Panamesine (EMD-57455)</a></li> <li><a href="/w/index.php?title=PD-144418&action=edit&redlink=1" class="new" title="PD-144418 (page does not exist)">PD-144418</a></li> <li><a href="/wiki/Pentazocine" title="Pentazocine">Pentazocine</a></li> <li><a class="mw-selflink selflink">Progesterone</a></li> <li><a href="/wiki/Rimcazole" title="Rimcazole">Rimcazole (BW-234U)</a></li> <li><a href="/wiki/Sertraline" title="Sertraline">Sertraline</a></li> <li><a href="/w/index.php?title=SR-31742A&action=edit&redlink=1" class="new" title="SR-31742A (page does not exist)">SR-31742A</a></li></ul> <ul><li>Allosteric modulators: <a href="/wiki/Phenytoin" title="Phenytoin">Phenytoin</a>; Positive: <a href="/wiki/Methylphenylpiracetam" title="Methylphenylpiracetam">Methylphenylpiracetam</a></li> <li><a href="/w/index.php?title=SOMCL-668&action=edit&redlink=1" class="new" title="SOMCL-668 (page does not exist)">SOMCL-668</a></li></ul> <ul><li>Unknown/unsorted: <a href="/w/index.php?title=3-Methoxydextrallorphan&action=edit&redlink=1" class="new" title="3-Methoxydextrallorphan (page does not exist)">3-Methoxydextrallorphan</a></li> <li><a href="/wiki/3-MeO-PCP" title="3-MeO-PCP">3-MeO-PCP</a></li> <li><a href="/wiki/4C-T-2" title="4C-T-2">4C-T-2</a></li> <li><a href="/w/index.php?title=4-IBP&action=edit&redlink=1" class="new" title="4-IBP (page does not exist)">4-IBP</a></li> <li><a href="/w/index.php?title=4-IPBS&action=edit&redlink=1" class="new" title="4-IPBS (page does not exist)">4-IPBS</a></li> <li><a href="/wiki/4-MeO-PCP" title="4-MeO-PCP">4-MeO-PCP</a></li> <li><a href="/wiki/5-MeO-DALT" title="5-MeO-DALT">5-MeO-DALT</a></li> <li><a href="/wiki/5-MeO-DiPT" title="5-MeO-DiPT">5-MeO-DiPT</a></li> <li><a href="/wiki/Amitriptyline" title="Amitriptyline">Amitriptyline</a></li> <li><a href="/w/index.php?title=Azidopamil&action=edit&redlink=1" class="new" title="Azidopamil (page does not exist)">Azidopamil</a></li> <li><a href="/wiki/Chlorpromazine" title="Chlorpromazine">Chlorpromazine</a></li> <li><a href="/wiki/Clemastine" title="Clemastine">Clemastine</a></li> <li><a href="/wiki/Clomipramine" title="Clomipramine">Clomipramine</a></li> <li><a href="/wiki/Clorgiline" title="Clorgiline">Clorgiline</a></li> <li><a href="/wiki/D-Deprenyl" title="D-Deprenyl">D-Deprenyl</a></li> <li><a href="/wiki/N,N-Diisopropyltryptamine" class="mw-redirect" title="N,N-Diisopropyltryptamine"><abbr title="N,N-Diisopropyltryptamine">DiPT</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 N,N-Diisopropyltryptamine</li> <li><a href="/wiki/N,N-Dipropyltryptamine" class="mw-redirect" title="N,N-Dipropyltryptamine"><abbr title="N,N-Dipropyltryptamine">DPT</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 N,N-Dipropyltryptamine</li> <li><a href="/wiki/Ibogaine" title="Ibogaine">Ibogaine</a></li> <li><a href="/wiki/Imipramine" title="Imipramine">Imipramine</a></li> <li><a href="/w/index.php?title=KCR-12-83.1&action=edit&redlink=1" class="new" title="KCR-12-83.1 (page does not exist)">KCR-12-83.1</a></li> <li><a href="/wiki/Nemonapride" title="Nemonapride">Nemonapride</a></li> <li><a href="/wiki/Noribogaine" title="Noribogaine">Noribogaine</a></li> <li><a href="/w/index.php?title=RHL-033&action=edit&redlink=1" class="new" title="RHL-033 (page does not exist)">RHL-033</a></li> <li><a href="/wiki/RS-67,333" title="RS-67,333">RS-67,333</a></li> <li><a href="/wiki/RTI-55" title="RTI-55">RTI-55</a></li> <li><a href="/wiki/Saffron" title="Saffron">Saffron</a></li> <li><a href="/wiki/Safinamide" title="Safinamide">Safinamide</a></li> <li><a href="/wiki/Selegiline" title="Selegiline">Selegiline</a></li> <li><a href="/w/index.php?title=Spipethiane&action=edit&redlink=1" class="new" title="Spipethiane (page does not exist)">Spipethiane</a></li> <li><a href="/wiki/Trifluoperazine" title="Trifluoperazine">Trifluoperazine</a></li> <li><a href="/wiki/W-18_(drug)" title="W-18 (drug)">W-18</a></li> <li><a href="/wiki/YKP10A" class="mw-redirect" title="YKP10A">YKP10A</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Sigma-2_receptor" title="Sigma-2 receptor">σ2</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>Agonists: <a href="/wiki/3-PPP" title="3-PPP">3-PPP</a></li> <li><a href="/wiki/Arketamine" title="Arketamine">Arketamine</a></li> <li><a href="/wiki/BD-1047" title="BD-1047">BD-1047</a></li> <li><a href="/wiki/BD1063" title="BD1063">BD1063</a></li> <li><a href="/wiki/Ditolylguanidine" title="Ditolylguanidine">Ditolylguanidine (DTG)</a></li> <li><a href="/w/index.php?title=DKR-1005&action=edit&redlink=1" class="new" title="DKR-1005 (page does not exist)">DKR-1005</a></li> <li><a href="/w/index.php?title=DKR-1051&action=edit&redlink=1" class="new" title="DKR-1051 (page does not exist)">DKR-1051</a></li> <li><a href="/wiki/Haloperidol" title="Haloperidol">Haloperidol</a></li> <li><a href="/wiki/Ifenprodil" title="Ifenprodil">Ifenprodil</a></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/MDMA" title="MDMA"><abbr title="Methylenedioxymethamphetamine">MDMA</abbr> (midomafetamine)</a></li> <li><a href="/wiki/Methamphetamine" title="Methamphetamine">Methamphetamine</a></li> <li><a href="/w/index.php?title=OPC-14523&action=edit&redlink=1" class="new" title="OPC-14523 (page does not exist)">OPC-14523</a></li> <li><a href="/wiki/Opipramol" title="Opipramol">Opipramol</a></li> <li><a href="/wiki/PB-28" title="PB-28">PB-28</a></li> <li><a href="/wiki/Phencyclidine" title="Phencyclidine">Phencyclidine</a></li> <li><a href="/wiki/Siramesine" title="Siramesine">Siramesine (Lu 28-179)</a></li> <li><a href="/w/index.php?title=UKH-1114&action=edit&redlink=1" class="new" title="UKH-1114 (page does not exist)">UKH-1114</a></li></ul> <ul><li>Antagonists: <a href="/wiki/AC-927" class="mw-redirect" title="AC-927">AC-927</a></li> <li><a href="/wiki/BD-1008" class="mw-redirect" title="BD-1008">BD-1008</a></li> <li><a href="/wiki/BD-1067" class="mw-redirect" title="BD-1067">BD-1067</a></li> <li><a href="/wiki/CM-156" class="mw-redirect" title="CM-156">CM-156</a></li> <li><a href="/w/index.php?title=CT-1812&action=edit&redlink=1" class="new" title="CT-1812 (page does not exist)">CT-1812</a></li> <li><a href="/w/index.php?title=LR-172&action=edit&redlink=1" class="new" title="LR-172 (page does not exist)">LR-172</a></li> <li><a href="/wiki/MIN-101" class="mw-redirect" title="MIN-101">MIN-101</a></li> <li><a href="/wiki/Panamesine" title="Panamesine">Panamesine (EMD-57455)</a></li> <li><a href="/w/index.php?title=SAS-0132&action=edit&redlink=1" class="new" title="SAS-0132 (page does not exist)">SAS-0132</a></li></ul> <ul><li>Unknown/unsorted: <a href="/w/index.php?title=3-Methoxydextrallorphan&action=edit&redlink=1" class="new" title="3-Methoxydextrallorphan (page does not exist)">3-Methoxydextrallorphan</a></li> <li><a href="/wiki/3-MeO-PCE" title="3-MeO-PCE">3-MeO-PCE</a></li> <li><a href="/wiki/4-MeO-PCP" title="4-MeO-PCP">4-MeO-PCP</a></li> <li><a href="/wiki/5-MeO-DALT" title="5-MeO-DALT">5-MeO-DALT</a></li> <li><a href="/wiki/5-MeO-DiPT" title="5-MeO-DiPT">5-MeO-DiPT</a></li> <li><a href="/wiki/Clemastine" title="Clemastine">Clemastine</a></li> <li><a href="/wiki/N,N-Diisopropyltryptamine" class="mw-redirect" title="N,N-Diisopropyltryptamine"><abbr title="N,N-Diisopropyltryptamine">DiPT</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 N,N-Diisopropyltryptamine</li> <li><a href="/wiki/N,N-Dipropyltryptamine" class="mw-redirect" title="N,N-Dipropyltryptamine"><abbr title="N,N-Dipropyltryptamine">DPT</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 N,N-Dipropyltryptamine</li> <li><a href="/wiki/Ibogaine" title="Ibogaine">Ibogaine</a></li> <li><a href="/wiki/Lu_29-252" title="Lu 29-252">Lu 29-252</a></li> <li><a href="/wiki/Nemonapride" title="Nemonapride">Nemonapride</a></li> <li><a href="/wiki/Nepinalone" title="Nepinalone">Nepinalone</a></li> <li><a href="/wiki/Noribogaine" title="Noribogaine">Noribogaine</a></li> <li><a href="/wiki/Pentazocine" title="Pentazocine">Pentazocine</a></li> <li><a href="/wiki/RS-67,333" title="RS-67,333">RS-67,333</a></li> <li><a href="/wiki/Safinamide" title="Safinamide">Safinamide</a></li> <li><a href="/wiki/3,4,5-Trimethoxyamphetamine" title="3,4,5-Trimethoxyamphetamine"><abbr title="3,4,5-Trimethoxyamphetamine">TMA</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 3,4,5-Trimethoxyamphetamine</li> <li><a href="/w/index.php?title=UMB-23&action=edit&redlink=1" class="new" title="UMB-23 (page does not exist)">UMB-23</a></li> <li><a href="/w/index.php?title=UMB-82&action=edit&redlink=1" class="new" title="UMB-82 (page does not exist)">UMB-82</a></li> <li><a href="/wiki/W-18_(drug)" title="W-18 (drug)">W-18</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Unsorted</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>Agonists: <a href="/wiki/Berberine" title="Berberine">Berberine</a></li> <li><a href="/wiki/Ethylketazocine" title="Ethylketazocine">Ethylketazocine</a></li> <li><a href="/wiki/Fourphit" title="Fourphit">Fourphit</a></li> <li><a href="/wiki/Metaphit" title="Metaphit">Metaphit</a></li> <li><a href="/wiki/Naluzotan" title="Naluzotan">Naluzotan</a></li> <li><a href="/wiki/Tapentadol" title="Tapentadol">Tapentadol</a></li> <li><a href="/wiki/Tenocyclidine" title="Tenocyclidine">Tenocyclidine</a></li></ul> <ul><li>Antagonists: <a href="/w/index.php?title=AHD1&action=edit&redlink=1" class="new" title="AHD1 (page does not exist)">AHD1</a></li> <li><a href="/w/index.php?title=AZ66&action=edit&redlink=1" class="new" title="AZ66 (page does not exist)">AZ66</a></li> <li><a href="/wiki/Lamotrigine" title="Lamotrigine">Lamotrigine</a></li> <li><a href="/wiki/Naloxone" title="Naloxone">Naloxone</a></li> <li><a href="/w/index.php?title=SM-21&action=edit&redlink=1" class="new" title="SM-21 (page does not exist)">SM-21</a></li> <li><a href="/w/index.php?title=UMB-100&action=edit&redlink=1" class="new" title="UMB-100 (page does not exist)">UMB-100</a></li> <li><a href="/w/index.php?title=UMB-101&action=edit&redlink=1" class="new" title="UMB-101 (page does not exist)">UMB-101</a></li> <li><a href="/w/index.php?title=UMB-103&action=edit&redlink=1" class="new" title="UMB-103 (page does not exist)">UMB-103</a></li> <li><a href="/w/index.php?title=UMB-116&action=edit&redlink=1" class="new" title="UMB-116 (page does not exist)">UMB-116</a></li> <li><a href="/w/index.php?title=YZ-011&action=edit&redlink=1" class="new" title="YZ-011 (page does not exist)">YZ-011</a></li> <li><a href="/w/index.php?title=YZ-069&action=edit&redlink=1" class="new" title="YZ-069 (page does not exist)">YZ-069</a></li> <li><a href="/w/index.php?title=YZ-185&action=edit&redlink=1" class="new" title="YZ-185 (page does not exist)">YZ-185</a></li></ul> <ul><li>Allosteric modulators: <a href="/wiki/SKF-83959" class="mw-redirect" title="SKF-83959">SKF-83959</a></li></ul> <ul><li>Unknown/unsorted: <a href="/wiki/18-Methoxycoronaridine" title="18-Methoxycoronaridine">18-Methoxycoronaridine</a></li> <li><a href="/w/index.php?title=BMY-13980&action=edit&redlink=1" class="new" title="BMY-13980 (page does not exist)">BMY-13980</a></li> <li><a href="/wiki/Butaclamol" title="Butaclamol">Butaclamol</a></li> <li><a href="/wiki/Caramiphen" title="Caramiphen">Caramiphen</a></li> <li><a href="/w/index.php?title=Carvotroline&action=edit&redlink=1" class="new" title="Carvotroline (page does not exist)">Carvotroline</a></li> <li><a href="/wiki/Chlorphenamine" title="Chlorphenamine">Chlorphenamine (chlorpheniramine)</a></li> <li><a href="/wiki/Chlorpromazine" title="Chlorpromazine">Chlorpromazine</a></li> <li><a href="/wiki/Cinnarizine" title="Cinnarizine">Cinnarizine</a></li> <li><a href="/w/index.php?title=Cinuperone&action=edit&redlink=1" class="new" title="Cinuperone (page does not exist)">Cinuperone</a></li> <li><a href="/wiki/Clocapramine" title="Clocapramine">Clocapramine</a></li> <li><a href="/wiki/Dezocine" title="Dezocine">Dezocine</a></li> <li><a href="/w/index.php?title=EMD-59983&action=edit&redlink=1" class="new" title="EMD-59983 (page does not exist)">EMD-59983</a></li> <li><a href="/wiki/Hypericin" title="Hypericin">Hypericin</a> (<a href="/wiki/St._John%27s_wort" class="mw-redirect" title="St. John's wort">St. John's wort</a>)</li> <li><a href="/wiki/Fluphenazine" title="Fluphenazine">Fluphenazine</a></li> <li><a href="/wiki/Gevotroline" title="Gevotroline">Gevotroline (WY-47384)</a></li> <li><a href="/wiki/Mepyramine" title="Mepyramine">Mepyramine (pyrilamine)</a></li> <li><a href="/wiki/Molindone" title="Molindone">Molindone</a></li> <li><a href="/wiki/Perphenazine" title="Perphenazine">Perphenazine</a></li> <li><a href="/wiki/Pimozide" title="Pimozide">Pimozide</a></li> <li><a href="/wiki/Proadifen" title="Proadifen">Proadifen</a></li> <li><a href="/wiki/Promethazine" title="Promethazine">Promethazine</a></li> <li><a href="/wiki/Propranolol" title="Propranolol">Propranolol</a></li> <li><a href="/wiki/Quinidine" title="Quinidine">Quinidine</a></li> <li><a href="/wiki/Remoxipride" title="Remoxipride">Remoxipride</a></li> <li><a href="/w/index.php?title=SL_82.0715&action=edit&redlink=1" class="new" title="SL 82.0715 (page does not exist)">SL 82.0715</a></li> <li><a href="/w/index.php?title=SR-31747A&action=edit&redlink=1" class="new" title="SR-31747A (page does not exist)">SR-31747A</a></li> <li><a href="/wiki/Tiospirone" title="Tiospirone">Tiospirone (BMY-13859)</a></li> <li><a href="/wiki/Venlafaxine" title="Venlafaxine">Venlafaxine</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div>See also: <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Xenobiotic-sensing_receptor_modulators953" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Xenobiotic-sensing_receptor_modulators" title="Template:Xenobiotic-sensing receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Xenobiotic-sensing_receptor_modulators" title="Template talk:Xenobiotic-sensing receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Xenobiotic-sensing_receptor_modulators" title="Special:EditPage/Template:Xenobiotic-sensing receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Xenobiotic-sensing_receptor_modulators953" style="font-size:114%;margin:0 4em"><a href="/wiki/Xenobiotic-sensing_receptor" title="Xenobiotic-sensing receptor">Xenobiotic-sensing receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Constitutive_androstane_receptor" title="Constitutive androstane receptor"><abbr title="Constitutive androstane receptor">CAR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Constitutive androstane receptor</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/w/index.php?title=6,7-Dimethylesculetin&action=edit&redlink=1" class="new" title="6,7-Dimethylesculetin (page does not exist)">6,7-Dimethylesculetin</a></li> <li><a href="/wiki/Amiodarone" title="Amiodarone">Amiodarone</a></li> <li><a href="/wiki/Artemisinin" title="Artemisinin">Artemisinin</a></li> <li><a href="/w/index.php?title=Benfuracarb&action=edit&redlink=1" class="new" title="Benfuracarb (page does not exist)">Benfuracarb</a></li> <li><a href="/wiki/Carbamazepine" title="Carbamazepine">Carbamazepine</a></li> <li><a href="/wiki/Carvedilol" title="Carvedilol">Carvedilol</a></li> <li><a href="/wiki/Chlorpromazine" title="Chlorpromazine">Chlorpromazine</a></li> <li><a href="/wiki/Chrysin" title="Chrysin">Chrysin</a></li> <li><a href="/w/index.php?title=CITCO_(drug)&action=edit&redlink=1" class="new" title="CITCO (drug) (page does not exist)">CITCO</a></li> <li><a href="/wiki/Clotrimazole" title="Clotrimazole">Clotrimazole</a></li> <li><a href="/wiki/Cyclophosphamide" title="Cyclophosphamide">Cyclophosphamide</a></li> <li><a href="/wiki/Cypermethrin" title="Cypermethrin">Cypermethrin</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a> (<a href="/wiki/Prasterone" title="Prasterone">prasterone</a>)</li> <li><a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Ellagic_acid" title="Ellagic acid">Ellagic acid</a></li> <li><a href="/wiki/Griseofulvin" title="Griseofulvin">Griseofulvin</a></li> <li><a href="/wiki/Methoxychlor" title="Methoxychlor">Methoxychlor</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li> <li><a href="/wiki/Nefazodone" title="Nefazodone">Nefazodone</a></li> <li><a href="/wiki/Nevirapine" title="Nevirapine">Nevirapine</a></li> <li><a href="/wiki/Nicardipine" title="Nicardipine">Nicardipine</a></li> <li><a href="/w/index.php?title=Octicizer&action=edit&redlink=1" class="new" title="Octicizer (page does not exist)">Octicizer</a></li> <li><a href="/wiki/Permethrin" title="Permethrin">Permethrin</a></li> <li><a href="/wiki/Phenobarbital" title="Phenobarbital">Phenobarbital</a></li> <li><a href="/wiki/Phenytoin" title="Phenytoin">Phenytoin</a></li> <li><a href="/wiki/5%CE%B2-Dihydroprogesterone" title="5β-Dihydroprogesterone">Pregnanedione (5β-dihydroprogesterone)</a></li> <li><a href="/wiki/Reserpine" title="Reserpine">Reserpine</a></li> <li><a href="/w/index.php?title=TCPOBOP&action=edit&redlink=1" class="new" title="TCPOBOP (page does not exist)">TCPOBOP</a></li> <li><a href="/wiki/Telmisartan" title="Telmisartan">Telmisartan</a></li> <li><a href="/wiki/Tolnaftate" title="Tolnaftate">Tolnaftate</a></li> <li><a href="/wiki/Troglitazone" title="Troglitazone">Troglitazone</a></li> <li><a href="/wiki/Valproic_acid" class="mw-redirect" title="Valproic acid">Valproic acid</a></li></ul> <ul><li>Antagonists: <a href="/w/index.php?title=3,17%CE%B2-Estradiol&action=edit&redlink=1" class="new" title="3,17β-Estradiol (page does not exist)">3,17β-Estradiol</a></li> <li><a href="/w/index.php?title=5%CE%B1-Androstan-3%CE%B1-ol&action=edit&redlink=1" class="new" title="5α-Androstan-3α-ol (page does not exist)">3α-Androstanol</a></li> <li><a href="/wiki/5%CE%B1-Androst-16-en-3%CE%B1-ol" class="mw-redirect" title="5α-Androst-16-en-3α-ol">3α-Androstenol</a></li> <li><a href="/w/index.php?title=5%CE%B1-Androstan-3%CE%B2-ol&action=edit&redlink=1" class="new" title="5α-Androstan-3β-ol (page does not exist)">3β-Androstanol</a></li> <li><a href="/w/index.php?title=5%CE%B1-Androstan-17-ol&action=edit&redlink=1" class="new" title="5α-Androstan-17-ol (page does not exist)">17-Androstanol</a></li> <li><a href="/wiki/Allyl_isothiocyanate" title="Allyl isothiocyanate">AITC</a></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a></li> <li><a href="/wiki/Meclizine" title="Meclizine">Meclizine</a></li> <li><a href="/w/index.php?title=Nigramide_J&action=edit&redlink=1" class="new" title="Nigramide J (page does not exist)">Nigramide J</a></li> <li><a href="/wiki/Okadaic_acid" title="Okadaic acid">Okadaic acid</a></li> <li><a href="/wiki/PK-11195" class="mw-redirect" title="PK-11195">PK-11195</a></li> <li><a href="/w/index.php?title=S-07662&action=edit&redlink=1" class="new" title="S-07662 (page does not exist)">S-07662</a></li> <li><a href="/w/index.php?title=T-0901317&action=edit&redlink=1" class="new" title="T-0901317 (page does not exist)">T-0901317</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Pregnane_X_receptor" title="Pregnane X receptor"><abbr title="Pregnane X receptor">PXR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Pregnane X receptor</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/17%CE%B1-Hydroxypregnenolone" title="17α-Hydroxypregnenolone">17α-Hydroxypregnenolone</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone</a></li> <li><a href="/wiki/%CE%944-Androstenedione" class="mw-redirect" title="Δ4-Androstenedione">Δ4-Androstenedione</a></li> <li><a href="/wiki/%CE%945-Androstenediol" class="mw-redirect" title="Δ5-Androstenediol">Δ5-Androstenediol</a></li> <li><a href="/wiki/%CE%945-Androstenedione" class="mw-redirect" title="Δ5-Androstenedione">Δ5-Androstenedione</a></li> <li><a href="/w/index.php?title=AA-861&action=edit&redlink=1" class="new" title="AA-861 (page does not exist)">AA-861</a></li> <li><a href="/wiki/Allopregnanediol" title="Allopregnanediol">Allopregnanediol</a></li> <li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">Allopregnanedione (5α-dihydroprogesterone)</a></li> <li><a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone (brexanolone)</a></li> <li><a href="/wiki/Alpha-Lipoic_acid" class="mw-redirect" title="Alpha-Lipoic acid">Alpha-Lipoic acid</a></li> <li><a href="/wiki/Ambrisentan" title="Ambrisentan">Ambrisentan</a></li> <li><a href="/wiki/AMI-193" class="mw-redirect" title="AMI-193">AMI-193</a></li> <li><a href="/wiki/Amlodipine_besylate" class="mw-redirect" title="Amlodipine besylate">Amlodipine besylate</a></li> <li><a href="/wiki/Antimycotic" class="mw-redirect" title="Antimycotic">Antimycotics</a></li> <li><a href="/wiki/Artemisinin" title="Artemisinin">Artemisinin</a></li> <li><a href="/wiki/Aurothioglucose" title="Aurothioglucose">Aurothioglucose</a></li> <li><a href="/wiki/Bile_acid" title="Bile acid">Bile acids</a></li> <li><a href="/wiki/Bithionol" title="Bithionol">Bithionol</a></li> <li><a href="/wiki/Bosentan" title="Bosentan">Bosentan</a></li> <li><a href="/w/index.php?title=Bumecaine&action=edit&redlink=1" class="new" title="Bumecaine (page does not exist)">Bumecaine</a></li> <li><a href="/wiki/Cafestol" title="Cafestol">Cafestol</a></li> <li><a href="/wiki/Cephaloridine" title="Cephaloridine">Cephaloridine</a></li> <li><a href="/wiki/Cephradine" class="mw-redirect" title="Cephradine">Cephradine</a></li> <li><a href="/wiki/Chlorpromazine" title="Chlorpromazine">Chlorpromazine</a></li> <li><a href="/wiki/Ciglitazone" title="Ciglitazone">Ciglitazone</a></li> <li><a href="/wiki/Clindamycin" title="Clindamycin">Clindamycin</a></li> <li><a href="/wiki/Clofenvinfos" class="mw-redirect" title="Clofenvinfos">Clofenvinfos</a></li> <li><a href="/wiki/Chloroxine" title="Chloroxine">Chloroxine</a></li> <li><a href="/wiki/Clotrimazole" title="Clotrimazole">Clotrimazole</a></li> <li><a href="/wiki/Colforsin" class="mw-redirect" title="Colforsin">Colforsin</a></li> <li><a href="/wiki/Corticosterone" title="Corticosterone">Corticosterone</a></li> <li><a href="/wiki/Cyclophosphamide" title="Cyclophosphamide">Cyclophosphamide</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Demecolcine" title="Demecolcine">Demecolcine</a></li> <li><a href="/wiki/Dexamethasone" title="Dexamethasone">Dexamethasone</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a> (<a href="/wiki/Prasterone" title="Prasterone">prasterone</a>)</li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA-S</a> (<a href="/wiki/Prasterone_sulfate" title="Prasterone sulfate">prasterone sulfate</a>)</li> <li><a href="/wiki/Dibunate_sodium" class="mw-redirect" title="Dibunate sodium">Dibunate sodium</a></li> <li><a href="/wiki/Diclazuril" title="Diclazuril">Diclazuril</a></li> <li><a href="/wiki/Dicloxacillin" title="Dicloxacillin">Dicloxacillin</a></li> <li><a href="/wiki/Dimercaprol" title="Dimercaprol">Dimercaprol</a></li> <li><a href="/w/index.php?title=Dinaline&action=edit&redlink=1" class="new" title="Dinaline (page does not exist)">Dinaline</a></li> <li><a href="/wiki/Docetaxel" title="Docetaxel">Docetaxel</a></li> <li><a href="/wiki/Docusate_calcium" class="mw-redirect" title="Docusate calcium">Docusate calcium</a></li> <li><a href="/wiki/Dodecylbenzenesulfonic_acid" class="mw-redirect" title="Dodecylbenzenesulfonic acid">Dodecylbenzenesulfonic acid</a></li> <li><a href="/wiki/Dronabinol" title="Dronabinol">Dronabinol</a></li> <li><a href="/wiki/Droxidopa" title="Droxidopa">Droxidopa</a></li> <li><a href="/wiki/Eburnamonine" class="mw-redirect" title="Eburnamonine">Eburnamonine</a></li> <li><a href="/wiki/Ecopipam" title="Ecopipam">Ecopipam</a></li> <li><a href="/wiki/Enzacamene" title="Enzacamene">Enzacamene</a></li> <li><a href="/wiki/Epothilone_B" class="mw-redirect" title="Epothilone B">Epothilone B</a></li> <li><a href="/wiki/Erythromycin" title="Erythromycin">Erythromycin</a></li> <li><a href="/wiki/Famprofazone" title="Famprofazone">Famprofazone</a></li> <li><a href="/w/index.php?title=Febantel&action=edit&redlink=1" class="new" title="Febantel (page does not exist)">Febantel</a></li> <li><a href="/wiki/Felodipine" title="Felodipine">Felodipine</a></li> <li><a href="/wiki/Fenbendazole" title="Fenbendazole">Fenbendazole</a></li> <li><a href="/wiki/Fentanyl" title="Fentanyl">Fentanyl</a></li> <li><a href="/wiki/Flucloxacillin" title="Flucloxacillin">Flucloxacillin</a></li> <li><a href="/wiki/Fluorometholone" title="Fluorometholone">Fluorometholone</a></li> <li><a href="/wiki/Griseofulvin" title="Griseofulvin">Griseofulvin</a></li> <li><a href="/wiki/Guggulsterone" title="Guggulsterone">Guggulsterone</a></li> <li><a href="/wiki/Haloprogin" title="Haloprogin">Haloprogin</a></li> <li><a href="/wiki/Hetacillin_potassium" class="mw-redirect" title="Hetacillin potassium">Hetacillin potassium</a></li> <li><a href="/wiki/Hyperforin" title="Hyperforin">Hyperforin</a></li> <li><a href="/wiki/Hypericum_perforatum" title="Hypericum perforatum">Hypericum perforatum (St John's wort)</a></li> <li><a href="/wiki/Indinavir_sulfate" class="mw-redirect" title="Indinavir sulfate">Indinavir sulfate</a></li> <li><a href="/wiki/Lasalocid_sodium" class="mw-redirect" title="Lasalocid sodium">Lasalocid sodium</a></li> <li><a href="/wiki/Levothyroxine" title="Levothyroxine">Levothyroxine</a></li> <li>Linolenic acid: <a href="/wiki/%CE%91-Linolenic_acid" title="Α-Linolenic acid">α-Linolenic acid</a> and <a href="/wiki/%CE%93-Linolenic_acid" title="Γ-Linolenic acid">γ-Linolenic acid</a></li> <li><a href="/w/index.php?title=LOE-908&action=edit&redlink=1" class="new" title="LOE-908 (page does not exist)">LOE-908</a></li> <li><a href="/wiki/Loratadine" title="Loratadine">Loratadine</a></li> <li><a href="/wiki/Lovastatin" title="Lovastatin">Lovastatin</a></li> <li><a href="/wiki/Meclizine" title="Meclizine">Meclizine</a></li> <li><a href="/wiki/Metacycline" title="Metacycline">Metacycline</a></li> <li><a href="/wiki/Methylprednisolone" title="Methylprednisolone">Methylprednisolone</a></li> <li><a href="/wiki/Metyrapone" title="Metyrapone">Metyrapone</a></li> <li><a href="/wiki/Mevastatin" title="Mevastatin">Mevastatin</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li> <li><a href="/wiki/Nafcillin" title="Nafcillin">Nafcillin</a></li> <li><a href="/wiki/Nicardipine" title="Nicardipine">Nicardipine</a></li> <li><a href="/wiki/Nicotine" title="Nicotine">Nicotine</a></li> <li><a href="/wiki/Nifedipine" title="Nifedipine">Nifedipine</a></li> <li><a href="/wiki/Nilvadipine" title="Nilvadipine">Nilvadipine</a></li> <li><a href="/wiki/Nisoldipine" title="Nisoldipine">Nisoldipine</a></li> <li><a href="/wiki/Norelgestromin" title="Norelgestromin">Norelgestromin</a></li> <li><a href="/wiki/Omeprazole" title="Omeprazole">Omeprazole</a></li> <li><a href="/wiki/Orlistat" title="Orlistat">Orlistat</a></li> <li><a href="/wiki/Oxatomide" title="Oxatomide">Oxatomide</a></li> <li><a href="/wiki/Paclitaxel" title="Paclitaxel">Paclitaxel</a></li> <li><a href="/wiki/Phenobarbital" title="Phenobarbital">Phenobarbital</a></li> <li><a href="/wiki/Piperine" title="Piperine">Piperine</a></li> <li><a href="/wiki/Plicamycin" title="Plicamycin">Plicamycin</a></li> <li><a href="/wiki/Prednisolone" title="Prednisolone">Prednisolone</a></li> <li><a href="/wiki/Pregnanediol" title="Pregnanediol">Pregnanediol</a></li> <li><a href="/wiki/5%CE%B2-Dihydroprogesterone" title="5β-Dihydroprogesterone">Pregnanedione (5β-dihydroprogesterone)</a></li> <li><a href="/wiki/Pregnanolone" title="Pregnanolone">Pregnanolone</a></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a></li> <li><a href="/wiki/Pregnenolone_16%CE%B1-carbonitrile" title="Pregnenolone 16α-carbonitrile">Pregnenolone 16α-carbonitrile</a></li> <li><a href="/wiki/Proadifen" title="Proadifen">Proadifen</a></li> <li><a class="mw-selflink selflink">Progesterone</a></li> <li><a href="/wiki/Quingestrone" title="Quingestrone">Quingestrone</a></li> <li><a href="/wiki/Reserpine" title="Reserpine">Reserpine</a></li> <li><a href="/wiki/Reverse_triiodothyronine" title="Reverse triiodothyronine">Reverse triiodothyronine</a></li> <li><a href="/wiki/Rifampicin" title="Rifampicin">Rifampicin</a></li> <li><a href="/wiki/Rifaximin" title="Rifaximin">Rifaximin</a></li> <li><a href="/wiki/Rimexolone" title="Rimexolone">Rimexolone</a></li> <li><a href="/wiki/Riodipine" title="Riodipine">Riodipine</a></li> <li><a href="/wiki/Ritonavir" title="Ritonavir">Ritonavir</a></li> <li><a href="/wiki/Simvastatin" title="Simvastatin">Simvastatin</a></li> <li><a href="/wiki/Sirolimus" title="Sirolimus">Sirolimus</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/wiki/Spiroxatrine" title="Spiroxatrine">Spiroxatrine</a></li> <li><a href="/w/index.php?title=SR-12813&action=edit&redlink=1" class="new" title="SR-12813 (page does not exist)">SR-12813</a></li> <li><a href="/w/index.php?title=Suberoylanilide&action=edit&redlink=1" class="new" title="Suberoylanilide (page does not exist)">Suberoylanilide</a></li> <li><a href="/wiki/Sulfisoxazole" class="mw-redirect" title="Sulfisoxazole">Sulfisoxazole</a></li> <li><a href="/wiki/Suramin" title="Suramin">Suramin</a></li> <li><a href="/wiki/Tacrolimus" title="Tacrolimus">Tacrolimus</a></li> <li><a href="/w/index.php?title=Tenylidone&action=edit&redlink=1" class="new" title="Tenylidone (page does not exist)">Tenylidone</a></li> <li><a href="/wiki/Terconazole" title="Terconazole">Terconazole</a></li> <li><a href="/wiki/Testosterone_isocaproate" title="Testosterone isocaproate">Testosterone isocaproate</a></li> <li><a href="/wiki/Tetracycline" title="Tetracycline">Tetracycline</a></li> <li><a href="/wiki/Thiamylal_sodium" class="mw-redirect" title="Thiamylal sodium">Thiamylal sodium</a></li> <li><a href="/wiki/Thiothixene" class="mw-redirect" title="Thiothixene">Thiothixene</a></li> <li><a href="/wiki/Thonzonium_bromide" title="Thonzonium bromide">Thonzonium bromide</a></li> <li><a href="/wiki/Tianeptine" title="Tianeptine">Tianeptine</a></li> <li><a href="/wiki/Troglitazone" title="Troglitazone">Troglitazone</a></li> <li><a href="/wiki/Troleandomycin" title="Troleandomycin">Troleandomycin</a></li> <li><a href="/w/index.php?title=Tropanyl_3,5-dimethulbenzoate&action=edit&redlink=1" class="new" title="Tropanyl 3,5-dimethulbenzoate (page does not exist)">Tropanyl 3,5-dimethulbenzoate</a></li> <li><a href="/wiki/Zafirlukast" title="Zafirlukast">Zafirlukast</a></li> <li><a href="/wiki/Zeranol" title="Zeranol">Zeranol</a></li></ul> <ul><li>Antagonists: <a href="/wiki/Ketoconazole" title="Ketoconazole">Ketoconazole</a></li> <li><a href="/wiki/Sesamin" title="Sesamin">Sesamin</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd></dl> </div></td></tr></tbody></table></div></div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Progesterone&oldid=1274265436">https://en.wikipedia.org/w/index.php?title=Progesterone&oldid=1274265436</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Progesterone" title="Category:Progesterone">Progesterone</a></li><li><a href="/wiki/Category:5%CE%B1-Reductase_inhibitors" title="Category:5α-Reductase inhibitors">5α-Reductase inhibitors</a></li><li><a href="/wiki/Category:11%CE%B2-Hydroxysteroid_dehydrogenase_inhibitors" title="Category:11β-Hydroxysteroid dehydrogenase inhibitors">11β-Hydroxysteroid dehydrogenase inhibitors</a></li><li><a href="/wiki/Category:Alkene_derivatives" title="Category:Alkene derivatives">Alkene derivatives</a></li><li><a href="/wiki/Category:Antimineralocorticoids" title="Category:Antimineralocorticoids">Antimineralocorticoids</a></li><li><a href="/wiki/Category:Diketones" title="Category:Diketones">Diketones</a></li><li><a href="/wiki/Category:GABAA_receptor_positive_allosteric_modulators" title="Category:GABAA receptor positive allosteric modulators">GABAA receptor positive allosteric modulators</a></li><li><a href="/wiki/Category:Glucocorticoids" title="Category:Glucocorticoids">Glucocorticoids</a></li><li><a href="/wiki/Category:Glycine_receptor_antagonists" title="Category:Glycine receptor antagonists">Glycine receptor antagonists</a></li><li><a href="/wiki/Category:Neurosteroids" title="Category:Neurosteroids">Neurosteroids</a></li><li><a href="/wiki/Category:Hepatotoxins" title="Category:Hepatotoxins">Hepatotoxins</a></li><li><a href="/wiki/Category:Hormones_of_the_hypothalamus-pituitary-adrenal_axis" title="Category:Hormones of the hypothalamus-pituitary-adrenal axis">Hormones of the hypothalamus-pituitary-adrenal axis</a></li><li><a href="/wiki/Category:Hormones_of_the_hypothalamus-pituitary-gonad_axis" title="Category:Hormones of the hypothalamus-pituitary-gonad axis">Hormones of the hypothalamus-pituitary-gonad axis</a></li><li><a href="/wiki/Category:Hormones_of_the_hypothalamic-pituitary-prolactin_axis" title="Category:Hormones of the hypothalamic-pituitary-prolactin axis">Hormones of the hypothalamic-pituitary-prolactin axis</a></li><li><a href="/wiki/Category:Hormones_of_the_ovary" title="Category:Hormones of the ovary">Hormones of the ovary</a></li><li><a href="/wiki/Category:Hormones_of_the_placenta" title="Category:Hormones of the placenta">Hormones of the placenta</a></li><li><a href="/wiki/Category:Hormones_of_the_suprarenal_cortex" title="Category:Hormones of the suprarenal cortex">Hormones of 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