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class="vector-toc-numb">4.1.3</span> <span>Occupation and downregulation of carrier proteins</span> </div> </a> <ul id="toc-Occupation_and_downregulation_of_carrier_proteins-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Antigonadotropic_activity" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Antigonadotropic_activity"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1.4</span> <span>Antigonadotropic activity</span> </div> </a> <ul id="toc-Antigonadotropic_activity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Mechanism_of_action_in_endometriosis" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Mechanism_of_action_in_endometriosis"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1.5</span> <span>Mechanism of action in endometriosis</span> </div> </a> <ul id="toc-Mechanism_of_action_in_endometriosis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Effects_in_men" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Effects_in_men"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1.6</span> <span>Effects in men</span> </div> </a> <ul id="toc-Effects_in_men-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Pharmacokinetics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmacokinetics"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Pharmacokinetics</span> </div> </a> <ul id="toc-Pharmacokinetics-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Chemistry" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Chemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Chemistry</span> </div> </a> <ul id="toc-Chemistry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-History" 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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Danazol</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 19 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-19" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">19 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%AF%D8%A7%D9%86%D8%A7%D8%B2%D9%88%D9%84" title="دانازول – Arabic" lang="ar" hreflang="ar" data-title="دانازول" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%AF%D8%A7%D9%86%D8%A7%D8%B2%D9%88%D9%84" title="دانازول – South Azerbaijani" lang="azb" hreflang="azb" data-title="دانازول" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Danasol" title="Danasol – Welsh" lang="cy" hreflang="cy" data-title="Danasol" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Danazol" title="Danazol – German" lang="de" hreflang="de" data-title="Danazol" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Danazol" title="Danazol – Spanish" lang="es" hreflang="es" data-title="Danazol" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%AF%D8%A7%D9%86%D8%A7%D8%B2%D9%88%D9%84" title="دانازول – Persian" lang="fa" hreflang="fa" data-title="دانازول" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Danazol" title="Danazol – French" lang="fr" hreflang="fr" data-title="Danazol" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Danazolo" title="Danazolo – Italian" lang="it" hreflang="it" data-title="Danazolo" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Danazol" title="Danazol – Dutch" lang="nl" hreflang="nl" data-title="Danazol" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%80%E3%83%8A%E3%82%BE%E3%83%BC%E3%83%AB" title="ダナゾール – Japanese" lang="ja" hreflang="ja" data-title="ダナゾール" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-or mw-list-item"><a href="https://or.wikipedia.org/wiki/%E0%AC%A1%E0%AC%BE%E0%AC%A8%E0%AC%BE%E0%AC%9C%E0%AD%8B%E0%AC%B2" title="ଡାନାଜୋଲ – Odia" lang="or" hreflang="or" data-title="ଡାନାଜୋଲ" data-language-autonym="ଓଡ଼ିଆ" data-language-local-name="Odia" class="interlanguage-link-target"><span>ଓଡ଼ିଆ</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Danazol" title="Danazol – Polish" lang="pl" hreflang="pl" data-title="Danazol" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Danazol" title="Danazol – Portuguese" lang="pt" hreflang="pt" data-title="Danazol" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%94%D0%B0%D0%BD%D0%B0%D0%B7%D0%BE%D0%BB" title="Даназол – Russian" lang="ru" hreflang="ru" data-title="Даназол" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Danazol" title="Danazol – Serbian" lang="sr" hreflang="sr" data-title="Danazol" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Danazol" title="Danazol – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Danazol" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Danazol" title="Danazol – Swedish" lang="sv" hreflang="sv" data-title="Danazol" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Danazol" title="Danazol – Turkish" lang="tr" hreflang="tr" data-title="Danazol" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E9%81%94%E9%82%A3%E5%94%91" title="達那唑 – Chinese" lang="zh" hreflang="zh" data-title="達那唑" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a 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.hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Danabol" class="mw-redirect" title="Danabol">Danabol</a>.</div> <div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Pharmaceutical compound</div> <style data-mw-deduplicate="TemplateStyles:r1269284339">@media screen{html.skin-theme-clientpref-night .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}</style> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Danazol">Danazol</span></caption><tbody><tr><td colspan="2" class="infobox-image"><span class="dark_mode_safe" typeof="mw:File"><a href="/wiki/File:Danazol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/30/Danazol.svg/225px-Danazol.svg.png" decoding="async" width="225" height="147" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/30/Danazol.svg/338px-Danazol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/30/Danazol.svg/450px-Danazol.svg.png 2x" data-file-width="512" data-file-height="335" /></a></span></td></tr><tr><td colspan="2" class="infobox-image"><span class="dark_mode_safe" typeof="mw:File"><a href="/wiki/File:Danazol_molecule_ball.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Danazol_molecule_ball.png/235px-Danazol_molecule_ball.png" decoding="async" width="235" height="181" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Danazol_molecule_ball.png/353px-Danazol_molecule_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/99/Danazol_molecule_ball.png/470px-Danazol_molecule_ball.png 2x" data-file-width="2560" data-file-height="1972" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Danatrol, Danocrine, Danol, Danoval, others</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">WIN-17757; 2,3-Isoxazolethisterone; 2,3-Isoxazol-17α-ethynyltestosterone; 17α-Ethynyl-17β-hydroxyandrost-4-en-[2,3-d]isoxazole</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/American_Society_of_Health-System_Pharmacists" title="American Society of Health-System Pharmacists">AHFS</a>/<a href="/wiki/Drugs.com" title="Drugs.com">Drugs.com</a></th><td class="infobox-data"><span title="www.drugs.com"><a rel="nofollow" class="external text" href="https://www.drugs.com/monograph/danazol.html">Monograph</a></span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/MedlinePlus" title="MedlinePlus">MedlinePlus</a></th><td class="infobox-data"><span title="medlineplus.gov"><a rel="nofollow" class="external text" href="https://medlineplus.gov/druginfo/meds/a682599.html">a682599</a></span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Pregnancy_category" title="Pregnancy category">Pregnancy<br />category</a></th><td class="infobox-data"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"> <ul><li><small><abbr class="country-name" title="Australia">AU</abbr>:</small> D</li> <li class="mw-empty-elt"></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of<br />administration</a></th><td class="infobox-data"><a href="/wiki/Oral_administration" title="Oral administration">By mouth</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_class" title="Drug class">Drug class</a></th><td class="infobox-data"><a href="/wiki/Androgen" title="Androgen">Androgen</a>; <a href="/wiki/Anabolic_steroid" title="Anabolic steroid">Anabolic steroid</a>; <a href="/wiki/Progestogen_(medication)" title="Progestogen (medication)">Progestogen</a>; <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">Progestin</a>; <a href="/wiki/Antigonadotropin" title="Antigonadotropin">Antigonadotropin</a>; <a href="/wiki/Steroidogenesis_inhibitor" title="Steroidogenesis inhibitor">Steroidogenesis inhibitor</a>; <a href="/wiki/Antiestrogen" title="Antiestrogen">Antiestrogen</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a href="/wiki/ATC_code_G03" title="ATC code G03">G03XA01</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=G03XA01">WHO</a></span>) </li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"> <ul><li><small><abbr class="country-name" title="Australia">AU</abbr>:</small> <a href="/wiki/Standard_for_the_Uniform_Scheduling_of_Medicines_and_Poisons#Schedule_4" title="Standard for the Uniform Scheduling of Medicines and Poisons">S4</a> (Prescription only)</li> <li><small><abbr class="country-name" title="Canada">CA</abbr></small>: <a href="/wiki/Prescription_drug" title="Prescription drug"> ℞-only</a></li> <li><small><abbr class="country-name" title="United Kingdom">UK</abbr>:</small> <a href="/wiki/Prescription_drug" title="Prescription drug">POM</a> (Prescription only)</li> <li><small><abbr class="country-name" title="United States">US</abbr>:</small> <a href="/wiki/Boxed_warning" title="Boxed warning"><span style="border:thin solid black;">WARNING</span></a><sup id="cite_ref-FDA-AllBoxedWarnings_1-0" class="reference"><a href="#cite_note-FDA-AllBoxedWarnings-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>Rx-only</li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a></th><td class="infobox-data">Saturable with dosage, higher with food intake<sup id="cite_ref-DanocrineLabel_2-0" class="reference"><a href="#cite_note-DanocrineLabel-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">Protein binding</a></th><td class="infobox-data">To <a href="/wiki/Human_serum_albumin" title="Human serum albumin">albumin</a>, <a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin"><abbr title="sex hormone-binding globulin">SHBG</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip sex hormone-binding globulin</span>, <a href="/wiki/Corticosteroid-binding_globulin" class="mw-redirect" title="Corticosteroid-binding globulin"><abbr title="corticosteroid-binding globulin">CBG</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip corticosteroid-binding globulin</span><sup id="cite_ref-GriffinD'Arcy1997_3-0" class="reference"><a href="#cite_note-GriffinD'Arcy1997-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-NieschlagBehre2010_4-0" class="reference"><a href="#cite_note-NieschlagBehre2010-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ThomasRock2012_5-0" class="reference"><a href="#cite_note-ThomasRock2012-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_metabolism" title="Drug metabolism">Metabolism</a></th><td class="infobox-data"><a href="/wiki/Liver" title="Liver">Liver</a> (<a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a>)<sup id="cite_ref-Martindale2013_9-3" class="reference"><a href="#cite_note-Martindale2013-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-LemkeWilliams2012_6-1" class="reference"><a href="#cite_note-LemkeWilliams2012-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Metabolite" title="Metabolite">Metabolites</a></th><td class="infobox-data">• <abbr title="2-Hydroxymethylethisterone">2-OHM-Ethisterone</abbr><sup id="cite_ref-LemkeWilliams2012_6-0" class="reference"><a href="#cite_note-LemkeWilliams2012-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><br />• <a href="/wiki/Ethisterone" title="Ethisterone">Ethisterone</a><sup id="cite_ref-Dörwald2013_7-0" class="reference"><a href="#cite_note-Dörwald2013-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Kurman2013_8-0" class="reference"><a href="#cite_note-Kurman2013-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Biological_half-life" title="Biological half-life">Elimination <span class="nowrap">half-life</span></a></th><td class="infobox-data">Acute: 3–10 hours<sup id="cite_ref-Martindale2013_9-0" class="reference"><a href="#cite_note-Martindale2013-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-DanocrineLabel_2-1" class="reference"><a href="#cite_note-DanocrineLabel-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><br />Chronic: 24–26 hours<sup id="cite_ref-Martindale2013_9-1" class="reference"><a href="#cite_note-Martindale2013-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Excretion" title="Excretion">Excretion</a></th><td class="infobox-data"><a href="/wiki/Urine" title="Urine">Urine</a>, <a href="/wiki/Feces" title="Feces">feces</a><sup id="cite_ref-Martindale2013_9-2" class="reference"><a href="#cite_note-Martindale2013-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-DanocrineLabel_2-2" class="reference"><a href="#cite_note-DanocrineLabel-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">(1<i>S</i>,2<i>R</i>,13<i>R</i>,14<i>S</i>,17<i>R</i>,18<i>S</i>)-17-ethynyl-2,18-dimethyl-7-oxa-6-azapentacyclo[11.7.0.0<sup>2,10</sup>.0<sup>4,8</sup>.0<sup>14,18</sup>]icosa-4(8),5,9-trien-17-ol</div></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=17230-88-5">17230-88-5</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <span style="font-weight:normal"><abbr title="Compound ID">CID</abbr></span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/28417">28417</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Guide_to_Pharmacology" title="Guide to Pharmacology">IUPHAR/BPS</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=6942">6942</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB01406">DB01406</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.26436.html">26436</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/N29QWW3BUO">N29QWW3BUO</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/KEGG" title="KEGG">KEGG</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D00289">D00289</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4315">CHEBI:4315</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL1479">ChEMBL1479</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID2022880">DTXSID2022880</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q419652#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.037.503">100.037.503</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q419652#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data"><span title="Carbon">C</span><sub>22</sub><span title="Hydrogen">H</span><sub>27</sub><span title="Nitrogen">N</span><span title="Oxygen">O</span><sub>2</sub></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data"><span class="nowrap"><span data-sort-value="7002337463000000000♠"></span>337.463</span> g·mol<sup>−1</sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=C%23C%5BC%40%5D1%28O%29CC%5BC%40H%5D2%5BC%40%40H%5D3CCC4%3DCc5oncc5C%5BC%40%5D4%28C%29%5BC%40H%5D3CC%5BC%40%40%5D21C">Interactive image</a></span></li></ul></div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=Cc5oncc5C[C@]4(C)[C@H]3CC[C@@]21C</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">InChI=1S/C22H27NO2/c1-4-22(24)10-8-18-16-6-5-15-11-19-14(13-23-25-19)12-20(15,2)17(16)7-9-21(18,22)3/h1,11,13,16-18,24H,5-10,12H2,2-3H3/t16-,17+,18+,20+,21+,22+/m1/s1<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:POZRVZJJTULAOH-LHZXLZLDSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-below"><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style><span class="nobold">  <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=464367029&page2=Danazol">(verify)</a></span></span></td></tr></tbody></table> <p><b>Danazol</b>, sold as <b>Danocrine</b> and other brand names, is a medication used in the treatment of <a href="/wiki/Endometriosis" title="Endometriosis">endometriosis</a>, <a href="/wiki/Fibrocystic_breast_disease" class="mw-redirect" title="Fibrocystic breast disease">fibrocystic breast disease</a>, <a href="/wiki/Hereditary_angioedema" title="Hereditary angioedema">hereditary angioedema</a> and other conditions.<sup id="cite_ref-Martindale2013_9-4" class="reference"><a href="#cite_note-Martindale2013-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-DanocrineLabel_2-3" class="reference"><a href="#cite_note-DanocrineLabel-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Elks2014_10-0" class="reference"><a href="#cite_note-Elks2014-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-IndexNominum2000_11-0" class="reference"><a href="#cite_note-IndexNominum2000-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MortonHall2012_12-0" class="reference"><a href="#cite_note-MortonHall2012-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> It is taken <a href="/wiki/Oral_administration" title="Oral administration">by mouth</a>.<sup id="cite_ref-DanocrineLabel_2-4" class="reference"><a href="#cite_note-DanocrineLabel-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>The use of danazol is limited by <a href="/wiki/Virilization" title="Virilization">masculinizing</a> <a href="/wiki/Side_effect" title="Side effect">side effects</a> such as <a href="/wiki/Acne" title="Acne">acne</a>, <a href="/wiki/Hirsutism" title="Hirsutism">excessive hair growth</a>, and <a href="/wiki/Voice_deepening" class="mw-redirect" title="Voice deepening">voice deepening</a>.<sup id="cite_ref-DanocrineLabel_2-5" class="reference"><a href="#cite_note-DanocrineLabel-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Farquhar2007_13-0" class="reference"><a href="#cite_note-Farquhar2007-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Danazol has a complex <a href="/wiki/Mechanism_of_action" title="Mechanism of action">mechanism of action</a>, and is characterized as a weak <a href="/wiki/Androgen" title="Androgen">androgen</a> and <a href="/wiki/Anabolic_steroid" title="Anabolic steroid">anabolic steroid</a>, a weak <a href="/wiki/Progestogen_(medication)" title="Progestogen (medication)">progestogen</a>, a weak <a href="/wiki/Antigonadotropin" title="Antigonadotropin">antigonadotropin</a>, a weak <a href="/wiki/Steroidogenesis_inhibitor" title="Steroidogenesis inhibitor">steroidogenesis inhibitor</a>, and a functional <a href="/wiki/Antiestrogen" title="Antiestrogen">antiestrogen</a>.<sup id="cite_ref-ThomasRock2012_5-1" class="reference"><a href="#cite_note-ThomasRock2012-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-JonesRock2015_14-0" class="reference"><a href="#cite_note-JonesRock2015-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Lupulescu1990_15-0" class="reference"><a href="#cite_note-Lupulescu1990-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-AltchekDeligdisch2003_16-0" class="reference"><a href="#cite_note-AltchekDeligdisch2003-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>Danazol was discovered in 1963 and was introduced for medical use in 1971.<sup id="cite_ref-JonesRock2015_14-1" class="reference"><a href="#cite_note-JonesRock2015-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-NeumannPotts1979_17-0" class="reference"><a href="#cite_note-NeumannPotts1979-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-EliasGwinup1983_18-0" class="reference"><a href="#cite_note-EliasGwinup1983-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Dmowski1971_19-0" class="reference"><a href="#cite_note-Dmowski1971-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> Due to their improved side-effect profiles, particularly their lack of masculinizing side effects, danazol has largely been replaced by <a href="/wiki/Gonadotropin-releasing_hormone_analogue" class="mw-redirect" title="Gonadotropin-releasing hormone analogue">gonadotropin-releasing hormone analogues</a> (GnRH analogues) in the treatment of endometriosis.<sup id="cite_ref-NieschlagBehre2010_4-1" class="reference"><a href="#cite_note-NieschlagBehre2010-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <style data-mw-deduplicate="TemplateStyles:r886046785">.mw-parser-output .toclimit-2 .toclevel-1 ul,.mw-parser-output .toclimit-3 .toclevel-2 ul,.mw-parser-output .toclimit-4 .toclevel-3 ul,.mw-parser-output .toclimit-5 .toclevel-4 ul,.mw-parser-output .toclimit-6 .toclevel-5 ul,.mw-parser-output .toclimit-7 .toclevel-6 ul{display:none}</style><div class="toclimit-3"><meta property="mw:PageProp/toc" /></div> <div class="mw-heading mw-heading2"><h2 id="Medical_uses">Medical uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Danazol&action=edit&section=1" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Danazol is used primarily in the treatment of <a href="/wiki/Endometriosis" title="Endometriosis">endometriosis</a>. It has also been used – mostly <a href="/wiki/Off-label" class="mw-redirect" title="Off-label">off-label</a> – for other indications, namely in the management of <a href="/wiki/Menorrhagia" class="mw-redirect" title="Menorrhagia">menorrhagia</a>, <a href="/wiki/Fibrocystic_breast_disease" class="mw-redirect" title="Fibrocystic breast disease">fibrocystic breast disease</a>, <a href="/wiki/Immune_thrombocytopenic_purpura" title="Immune thrombocytopenic purpura">immune thrombocytopenic purpura</a>, <a href="/wiki/Premenstrual_syndrome" title="Premenstrual syndrome">premenstrual syndrome</a>, <a href="/wiki/Mastodynia" class="mw-redirect" title="Mastodynia">breast pain</a>, and <a href="/wiki/Hereditary_angioedema" title="Hereditary angioedema">hereditary angioedema</a>.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> Although not currently a standard treatment for <a href="/wiki/Menorrhagia" class="mw-redirect" title="Menorrhagia">menorrhagia</a>, danazol demonstrated significant relief in young women with menorrhagia in a study, and, because of a lack of a significant adverse effects, it was proposed as an alternative treatment.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> Danazol appears to be useful in the treatment of <a href="/wiki/Systemic_lupus_erythematosus" class="mw-redirect" title="Systemic lupus erythematosus">systemic lupus erythematosus</a>.<sup id="cite_ref-pmid20541792_22-0" class="reference"><a href="#cite_note-pmid20541792-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Available_forms">Available forms</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Danazol&action=edit&section=2" title="Edit section: Available forms"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Danazol comes in the form of 50, 100, and 200 mg <a href="/wiki/Oral_administration" title="Oral administration">oral</a> <a href="/wiki/Capsule_(pharmacy)" title="Capsule (pharmacy)">capsules</a>.<sup id="cite_ref-DanocrineLabel_2-6" class="reference"><a href="#cite_note-DanocrineLabel-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> It is taken at a dose of 50 to 400 mg two or three times per day, for a total of 100 to 800 mg per day depending on the indication.<sup id="cite_ref-DanocrineLabel_2-7" class="reference"><a href="#cite_note-DanocrineLabel-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Contraindications">Contraindications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Danazol&action=edit&section=3" title="Edit section: Contraindications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Danazol is <a href="/wiki/Contraindication" title="Contraindication">contraindicated</a> during <a href="/wiki/Pregnancy" title="Pregnancy">pregnancy</a> because it has the potential to <a href="/wiki/Virilization" title="Virilization">virilize</a> female <a href="/wiki/Fetus" title="Fetus">fetuses</a>. Women taking danazol should practice effective <a href="/wiki/Contraception" class="mw-redirect" title="Contraception">contraception</a> to prevent pregnancy if <a href="/wiki/Human_sexual_activity" title="Human sexual activity">sexually active</a>.<sup id="cite_ref-Hoffman_23-0" class="reference"><a href="#cite_note-Hoffman-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p><p>Since danazol is <a href="/wiki/Metabolism" title="Metabolism">metabolized</a> by the <a href="/wiki/Liver" title="Liver">liver</a>, it cannot be used by patients with <a href="/wiki/Liver_disease" title="Liver disease">liver disease</a>, and in patients receiving long-term therapy, liver function must be monitored on a periodic basis.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Side_effects">Side effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Danazol&action=edit&section=4" title="Edit section: Side effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Anabolic_steroid#Adverse_effects" title="Anabolic steroid">Anabolic steroid § Adverse effects</a></div> <p>Androgenic side effects are of concern, as some women taking danazol may experience unwanted hair growth (<a href="/wiki/Hirsutism" title="Hirsutism">hirsutism</a>), <a href="/wiki/Acne_vulgaris" class="mw-redirect" title="Acne vulgaris">acne</a>, irreversible <a href="/wiki/Voice_change" title="Voice change">deepening of the voice</a>,<sup id="cite_ref-NieschlagBehre2010_4-2" class="reference"><a href="#cite_note-NieschlagBehre2010-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> or adverse <a href="/wiki/Lipid_profile" title="Lipid profile">blood lipid profiles</a>.<sup id="cite_ref-Hoffman_23-1" class="reference"><a href="#cite_note-Hoffman-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> In addition, <a href="/wiki/Breast_atrophy" title="Breast atrophy">breast atrophy</a> and decreased breast size may occur.<sup id="cite_ref-NieschlagBehre2010_4-3" class="reference"><a href="#cite_note-NieschlagBehre2010-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> The drug may also cause <a href="/wiki/Hot_flash" title="Hot flash">hot flashes</a>, <a href="/wiki/Elevated_transaminases" title="Elevated transaminases">elevation of liver enzymes</a>, and <a href="/wiki/Mood_disorder" title="Mood disorder">mood changes</a>.<sup id="cite_ref-Hoffman_23-2" class="reference"><a href="#cite_note-Hoffman-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p><p>The use of danazol for endometriosis has been linked to an increased risk of <a href="/wiki/Ovarian_cancer" title="Ovarian cancer">ovarian cancer</a>.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> Patients with endometriosis have specific risk factors for ovarian cancer, so this may not apply for other uses. Danazol, like most other anabolic steroids, has been linked with an increased risk of <a href="/wiki/Liver_tumors" class="mw-redirect" title="Liver tumors">liver tumors</a>. These are generally <a href="/wiki/Benign_tumor" title="Benign tumor">benign</a>.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Danazol&action=edit&section=5" title="Edit section: Pharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Pharmacodynamics">Pharmacodynamics</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Danazol&action=edit&section=6" title="Edit section: Pharmacodynamics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Danazol possesses a complex <a href="/wiki/Pharmacology" title="Pharmacology">pharmacology</a>, with multiple <a href="/wiki/Mechanisms_of_action" class="mw-redirect" title="Mechanisms of action">mechanisms of action</a>.<sup id="cite_ref-ThomasRock2012_5-2" class="reference"><a href="#cite_note-ThomasRock2012-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-JonesRock2015_14-2" class="reference"><a href="#cite_note-JonesRock2015-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Lupulescu1990_15-1" class="reference"><a href="#cite_note-Lupulescu1990-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> These include direct binding to and activation of <a href="/wiki/Sex_hormone_receptor" title="Sex hormone receptor">sex hormone receptors</a>, direct <a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibition</a> of <a href="/wiki/Enzyme" title="Enzyme">enzymes</a> involved in <a href="/wiki/Steroidogenesis" class="mw-redirect" title="Steroidogenesis">steroidogenesis</a>, and direct binding to and occupation of <a href="/wiki/Steroid_hormone" title="Steroid hormone">steroid hormone</a> <a href="/wiki/Carrier_protein" class="mw-redirect" title="Carrier protein">carrier proteins</a> and consequent displacement of steroid hormones from these proteins.<sup id="cite_ref-NieschlagBehre2010_4-4" class="reference"><a href="#cite_note-NieschlagBehre2010-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ThomasRock2012_5-3" class="reference"><a href="#cite_note-ThomasRock2012-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-JonesRock2015_14-3" class="reference"><a href="#cite_note-JonesRock2015-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Lupulescu1990_15-2" class="reference"><a href="#cite_note-Lupulescu1990-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> The drug is characterized as a weak <a href="/wiki/Androgen" title="Androgen">androgen</a> and <a href="/wiki/Anabolic_steroid" title="Anabolic steroid">anabolic</a>, a weak <a href="/wiki/Progestogen_(medication)" title="Progestogen (medication)">progestogen</a>, a weak <a href="/wiki/Antigonadotropin" title="Antigonadotropin">antigonadotropin</a>, a weak <a href="/wiki/Steroidogenesis_inhibitor" title="Steroidogenesis inhibitor">steroidogenesis inhibitor</a>, and a functional <a href="/wiki/Antiestrogen" title="Antiestrogen">antiestrogen</a>.<sup id="cite_ref-JonesRock2015_14-4" class="reference"><a href="#cite_note-JonesRock2015-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-AltchekDeligdisch2003_16-1" class="reference"><a href="#cite_note-AltchekDeligdisch2003-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Modulation_of_steroid_hormone_receptors">Modulation of steroid hormone receptors</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Danazol&action=edit&section=7" title="Edit section: Modulation of steroid hormone receptors"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Danazol is described as a possessing high affinity for the <a href="/wiki/Androgen_receptor" title="Androgen receptor">androgen receptor</a> (AR), moderate affinity for the <a href="/wiki/Progesterone_receptor" title="Progesterone receptor">progesterone receptor</a> (PR) and <a href="/wiki/Glucocorticoid_receptor" title="Glucocorticoid receptor">glucocorticoid receptor</a> (GR), and poor affinity for the <a href="/wiki/Estrogen_receptor" title="Estrogen receptor">estrogen receptor</a> (ER).<sup id="cite_ref-NieschlagBehre2010_4-5" class="reference"><a href="#cite_note-NieschlagBehre2010-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ThomasRock2012_5-4" class="reference"><a href="#cite_note-ThomasRock2012-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> As an androgen, danazol is described as weak, being about 200-fold less potent than testosterone in <a href="/wiki/Bioassay" title="Bioassay">bioassays</a>.<sup id="cite_ref-AltchekDeligdisch2003_16-2" class="reference"><a href="#cite_note-AltchekDeligdisch2003-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> The drug can act as both an agonist and <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonist</a> of the PR depending on the bioassay, indicating that it could be regarded as a <a href="/wiki/Selective_progesterone_receptor_modulator" title="Selective progesterone receptor modulator">selective progesterone receptor modulator</a> (SPRM).<sup id="cite_ref-ThomasRock2012_5-5" class="reference"><a href="#cite_note-ThomasRock2012-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Although the <a href="/wiki/Affinity_(pharmacology)" class="mw-redirect" title="Affinity (pharmacology)">affinity</a> and <a href="/wiki/Intrinsic_activity" title="Intrinsic activity">efficacy</a> of danazol itself at the PR are relatively low, ethisterone, one of the major metabolites of danazol, is described as a weak progestogen (and has been employed clinically as a progestogen), and this presumably serves to increase the <i><a href="/wiki/In_vivo" title="In vivo">in vivo</a></i> progestogenic activity of danazol.<sup id="cite_ref-Kurman2013_8-1" class="reference"><a href="#cite_note-Kurman2013-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> The activity of danazol at the ER is considered to be minimal, although at very high concentrations the drug can act significantly as an ER agonist.<sup id="cite_ref-ThomasRock2012_5-6" class="reference"><a href="#cite_note-ThomasRock2012-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Danazol is considered to act significantly as an agonist of the GR, and, thus, as a <a href="/wiki/Glucocorticoid" title="Glucocorticoid">glucocorticoid</a>.<sup id="cite_ref-ThomasRock2012_5-7" class="reference"><a href="#cite_note-ThomasRock2012-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> In accordance, it can <a href="/wiki/Immunosuppression" title="Immunosuppression">suppress the immune system</a> at sufficient dosages.<sup id="cite_ref-ThomasRock2012_5-8" class="reference"><a href="#cite_note-ThomasRock2012-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-JonesRock2015_14-5" class="reference"><a href="#cite_note-JonesRock2015-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-AltchekDeligdisch2003_16-3" class="reference"><a href="#cite_note-AltchekDeligdisch2003-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable sortable mw-collapsible mw-collapsed" style="text-align:left; margin-left:auto; margin-right:auto; border:none;"> <caption class="nowrap">Relative affinities (%) of danazol and metabolites </caption> <tbody><tr> <th>Steroid</th> <th><a href="/wiki/Progesterone_receptor" title="Progesterone receptor"><abbr title="Progesterone receptor">PR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Progesterone receptor</span></th> <th><a href="/wiki/Androgen_receptor" title="Androgen receptor"><abbr title="Androgen receptor">AR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Androgen receptor</span></th> <th><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor</span></th> <th><a href="/wiki/Glucocorticoid_receptor" title="Glucocorticoid receptor"><abbr title="Glucocorticoid receptor">GR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Glucocorticoid receptor</span></th> <th><a href="/wiki/Mineralocorticoid_receptor" title="Mineralocorticoid receptor"><abbr title="Mineralocorticoid receptor">MR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Mineralocorticoid receptor</span></th> <th><a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin"><abbr title="Sex hormone-binding globulin">SHBG</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Sex hormone-binding globulin</span></th> <th><a href="/wiki/Corticosteroid_binding_globulin" class="mw-redirect" title="Corticosteroid binding globulin"><abbr title="Corticosteroid binding globulin">CBG</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Corticosteroid binding globulin</span> </th></tr> <tr> <td>Danazol</td> <td>9</td> <td>8</td> <td>?</td> <td><0.2<sup>a</sup></td> <td>?</td> <td>40</td> <td>10 </td></tr> <tr> <td><a href="/wiki/Ethisterone" title="Ethisterone">Ethisterone</a></td> <td>35</td> <td><1</td> <td><1</td> <td><1<sup>b</sup></td> <td><1</td> <td>92–121</td> <td>0.33 </td></tr> <tr> <td><a href="/wiki/5%CE%B1-Dihydroethisterone" title="5α-Dihydroethisterone">5α-Dihydroethisterone</a></td> <td>12</td> <td>38–100<sup>c</sup></td> <td>4</td> <td>120<sup>b</sup></td> <td>?</td> <td>100</td> <td>? </td></tr> <tr class="sortbottom"> <td colspan="8" style="width: 1px; background-color:#eaecf0; text-align: center;"><b>Notes:</b> Values are percentages (%). Reference ligands (100%) were <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a> for the <a href="/wiki/Progesterone_receptor" title="Progesterone receptor"><abbr title="progesterone receptor">PR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip progesterone receptor</span>, <a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">testosterone</a> (<sup>c</sup> = <a href="/wiki/Androstanolone" title="Androstanolone"><abbr title="dihydrotestosterone">DHT</abbr></a>) for the <a href="/wiki/Androgen_receptor" title="Androgen receptor"><abbr title="androgen receptor">AR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip androgen receptor</span>, <a href="/wiki/Hydrocortisone" title="Hydrocortisone">cortisol</a> for the <a href="/wiki/Glucocorticoid_receptor" title="Glucocorticoid receptor"><abbr title="glucocorticoid receptor">GR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip glucocorticoid receptor</span> (<sup>b</sup> = <a href="/wiki/Dexamethasone" title="Dexamethasone">dexamethasone</a>), <a href="/wiki/Aldosterone" title="Aldosterone">aldosterone</a> for the <a href="/wiki/Mineralocorticoid_receptor" title="Mineralocorticoid receptor"><abbr title="mineralocorticoid receptor">MR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip mineralocorticoid receptor</span>, <a href="/wiki/Androstanolone" title="Androstanolone"><abbr title="dihydrotestosterone">DHT</abbr></a> for <a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin"><abbr title="sex hormone-binding globulin">SHBG</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip sex hormone-binding globulin</span>, and cortisol for <a href="/wiki/Corticosteroid-binding_globulin" class="mw-redirect" title="Corticosteroid-binding globulin"><abbr title="corticosteroid-binding globulin">CBG</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip corticosteroid-binding globulin</span>. <sup>a</sup> = 1-hour incubation time (4 hours is standard for this assay; may affect affinity value). <b>Sources:</b> <sup id="cite_ref-pmid8136304_27-0" class="reference"><a href="#cite_note-pmid8136304-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid359134_28-0" class="reference"><a href="#cite_note-pmid359134-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid7382482_29-0" class="reference"><a href="#cite_note-pmid7382482-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid7195405_30-0" class="reference"><a href="#cite_note-pmid7195405-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid7197818_31-0" class="reference"><a href="#cite_note-pmid7197818-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid20814732_32-0" class="reference"><a href="#cite_note-pmid20814732-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> </td></tr></tbody></table> <table class="wikitable mw-collapsible mw-collapsed" style="text-align:left; margin-left:auto; margin-right:auto; border:none;"> <caption class="nowrap">Absolute affinities (nM) of danazol </caption> <tbody><tr> <th><a href="/wiki/Receptor_(biochemistry)" title="Receptor (biochemistry)">Receptor</a></th> <th><a href="/wiki/Affinity_(pharmacology)" class="mw-redirect" title="Affinity (pharmacology)">Affinity</a></th> <th><a href="/wiki/Intrinsic_activity" title="Intrinsic activity">Action</a> </th></tr> <tr> <td><a href="/wiki/Androgen_receptor" title="Androgen receptor">Androgen receptor</a></td> <td>90</td> <td><a href="/wiki/Agonist" title="Agonist">Agonist</a> </td></tr> <tr> <td><a href="/wiki/Progesterone_receptor" title="Progesterone receptor">Progesterone receptor</a></td> <td>6,000</td> <td><a href="/wiki/Agonist%E2%80%93antagonist" class="mw-redirect" title="Agonist–antagonist">Agonist–antagonist</a> </td></tr> <tr> <td><a href="/wiki/Glucocorticoid_receptor" title="Glucocorticoid receptor">Glucocorticoid receptor</a></td> <td>5,000</td> <td>Agonist </td></tr> <tr> <td><a href="/wiki/Estrogen_receptor" title="Estrogen receptor">Estrogen receptor</a></td> <td>80,000</td> <td>Agonist </td></tr> <tr class="sortbottom"> <td colspan="3" style="width: 1px; background-color:#eaecf0; text-align: center;"><b>Sources:</b> <sup id="cite_ref-NieschlagBehre2010_4-6" class="reference"><a href="#cite_note-NieschlagBehre2010-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ThomasRock2012_5-9" class="reference"><a href="#cite_note-ThomasRock2012-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </td></tr></tbody></table> <div class="mw-heading mw-heading4"><h4 id="Inhibition_of_steroidogenesis_enzymes">Inhibition of steroidogenesis enzymes</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Danazol&action=edit&section=8" title="Edit section: Inhibition of steroidogenesis enzymes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Danazol has been found to act as an <a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibitor</a>, to varying extents, of a variety of <a href="/wiki/Steroidogenic_enzyme" title="Steroidogenic enzyme">steroidogenic enzymes</a>, including <a href="/wiki/Cholesterol_side-chain_cleavage_enzyme" title="Cholesterol side-chain cleavage enzyme">cholesterol side-chain cleavage enzyme</a>, <a href="/wiki/3%CE%B2-hydroxysteroid_dehydrogenase" class="mw-redirect" title="3β-hydroxysteroid dehydrogenase">3β-hydroxysteroid dehydrogenase/Δ<sup>5-4</sup> isomerase</a>, <a href="/wiki/17%CE%B1-hydroxylase" class="mw-redirect" title="17α-hydroxylase">17α-hydroxylase</a>, <a href="/wiki/17,20-lyase" class="mw-redirect" title="17,20-lyase">17,20-lyase</a>, <a href="/wiki/17%CE%B2-hydroxysteroid_dehydrogenase" class="mw-redirect" title="17β-hydroxysteroid dehydrogenase">17β-hydroxysteroid dehydrogenase</a>, <a href="/wiki/21-hydroxylase" class="mw-redirect" title="21-hydroxylase">21-hydroxylase</a>, and <a href="/wiki/11%CE%B2-hydroxylase" class="mw-redirect" title="11β-hydroxylase">11β-hydroxylase</a>.<sup id="cite_ref-ThomasRock2012_5-10" class="reference"><a href="#cite_note-ThomasRock2012-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> It has also been found to be a weak inhibitor of <a href="/wiki/Steroid_sulfatase" title="Steroid sulfatase">steroid sulfatase</a> (K<sub>i</sub> = 2.3–8.2 μM), the enzyme that converts <a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate"><abbr title="dehydroepiandrosterone sulfate">DHEA-S</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 dehydroepiandrosterone sulfate</span> into <a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone"><abbr title="dehydroepiandrosterone">DHEA</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 dehydroepiandrosterone</span> and <a href="/wiki/Estrone_sulfate" title="Estrone sulfate">estrone sulfate</a> into <a href="/wiki/Estrone" title="Estrone">estrone</a> (which can then respectively be transformed into estrone (with <a href="/wiki/Androstenedione" title="Androstenedione">androstenedione</a> as an intermediate) and <a href="/wiki/Estradiol" title="Estradiol">estradiol</a>),<sup id="cite_ref-Shields-BotellaChetrite2005_33-0" class="reference"><a href="#cite_note-Shields-BotellaChetrite2005-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> though another study reported its inhibition to be potent and potentially clinically relevant.<sup id="cite_ref-pmid6238495_34-0" class="reference"><a href="#cite_note-pmid6238495-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> Although in contradiction with the above data, another study found that danazol weakly inhibited aromatase as well, with 44% inhibition at a concentration of 10 μM.<sup id="cite_ref-Shields-BotellaChetrite2005_33-1" class="reference"><a href="#cite_note-Shields-BotellaChetrite2005-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p><p>In accordance with its <a href="/wiki/Steroidogenesis_inhibitor" title="Steroidogenesis inhibitor">steroidogenesis inhibition</a>, clinical studies have demonstrated that danazol directly and markedly inhibits <a href="/wiki/Adrenal_gland" title="Adrenal gland">adrenal</a>, <a href="/wiki/Ovary" title="Ovary">ovarian</a>, and <a href="/wiki/Testicle" title="Testicle">testicular</a> steroidogenesis <i><a href="/wiki/In_vivo" title="In vivo">in vivo</a></i>.<sup id="cite_ref-ThomasRock2012_5-11" class="reference"><a href="#cite_note-ThomasRock2012-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> The enzymatic production of <a href="/wiki/Estradiol" title="Estradiol">estradiol</a>, <a href="/wiki/Progesterone" title="Progesterone">progesterone</a>, and <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> have all specifically been found to be inhibited.<sup id="cite_ref-ThomasRock2012_5-12" class="reference"><a href="#cite_note-ThomasRock2012-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable mw-collapsible mw-collapsed" style="text-align:left; margin-left:auto; margin-right:auto; border:none;"> <caption class="nowrap">Danazol at steroiodgenic enzymes </caption> <tbody><tr> <th>Enzyme</th> <th>Affinity (K<sub>i</sub>)</th> <th>Inhibition type</th> <th>Estimated inhibition at 2 μM </th></tr> <tr> <td><a href="/wiki/Cholesterol_side-chain_cleavage_enzyme" title="Cholesterol side-chain cleavage enzyme">Cholesterol side-chain cleavage enzyme</a></td> <td>20 μM</td> <td>Competitive</td> <td>? </td></tr> <tr> <td><a href="/wiki/3%CE%B2-Hydroxysteroid_dehydrogenase" title="3β-Hydroxysteroid dehydrogenase">3β-Hydroxysteroid dehydrogenase/Δ<sup>5-4</sup> isomerase</a></td> <td>5.8 μM</td> <td>Competitive</td> <td>4.3% </td></tr> <tr> <td><a href="/wiki/17%CE%B1-Hydroxylase" class="mw-redirect" title="17α-Hydroxylase">17α-Hydroxylase</a></td> <td>2.4 μM</td> <td>Competitive</td> <td>2.9% </td></tr> <tr> <td><a href="/wiki/17,20-Lyase" class="mw-redirect" title="17,20-Lyase">17,20-Lyase</a></td> <td>1.9 μM</td> <td>Competitive</td> <td>3.9% </td></tr> <tr> <td><a href="/wiki/17%CE%B2-Hydroxysteroid_dehydrogenase" title="17β-Hydroxysteroid dehydrogenase">17β-Hydroxysteroid dehydrogenase</a></td> <td>4.4 μM</td> <td>Competitive</td> <td>15% </td></tr> <tr> <td><a href="/wiki/21-Hydroxylase" title="21-Hydroxylase">21-Hydroxylase</a></td> <td>0.8 μM</td> <td>Competitive</td> <td>37% </td></tr> <tr> <td><a href="/wiki/11%CE%B2-Hydroxylase" class="mw-redirect" title="11β-Hydroxylase">11β-Hydroxylase</a></td> <td>1 μM</td> <td>Competitive</td> <td>21% </td></tr> <tr> <td><a href="/wiki/Aromatase" title="Aromatase">Aromatase</a></td> <td>>100 μM</td> <td>–</td> <td>0% </td></tr> <tr class="sortbottom"> <td colspan="4" style="width: 1px; background-color:#eaecf0; text-align: center;"><b>Sources:</b> <sup id="cite_ref-ThomasRock2012_5-13" class="reference"><a href="#cite_note-ThomasRock2012-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </td></tr></tbody></table> <p>For reference, circulating concentrations of danazol are in the range of 2 μM at a dosage of 600 mg/day in women.<sup id="cite_ref-ThomasRock2012_5-14" class="reference"><a href="#cite_note-ThomasRock2012-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Occupation_and_downregulation_of_carrier_proteins">Occupation and downregulation of carrier proteins</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Danazol&action=edit&section=9" title="Edit section: Occupation and downregulation of carrier proteins"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table class="wikitable floatright"> <caption class="nowrap">Protein binding of testosterone in women </caption> <tbody><tr> <th>Group</th> <th>Free</th> <th>Albumin</th> <th>SHBG </th></tr> <tr> <td><b>Normal (no danazol)</b></td> <td>1%</td> <td>39%</td> <td>60% </td></tr> <tr> <td><b>Danazol treatment</b></td> <td>3%</td> <td>79%</td> <td>18% </td></tr> <tr class="sortbottom"> <td colspan="4" style="width: 1px; background-color:#eaecf0; text-align: center;"><b>Sources:</b> <sup id="cite_ref-ThomasRock2012_5-15" class="reference"><a href="#cite_note-ThomasRock2012-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </td></tr></tbody></table> <p>Danazol is known to bind to two steroid hormone carrier proteins: <a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin">sex hormone-binding globulin</a> (SHBG), which binds <a href="/wiki/Androgen" title="Androgen">androgens</a> and <a href="/wiki/Estrogen" title="Estrogen">estrogens</a>; and <a href="/wiki/Corticosteroid-binding_globulin" class="mw-redirect" title="Corticosteroid-binding globulin">corticosteroid-binding globulin</a> (CBG), which binds progesterone and <a href="/wiki/Cortisol" title="Cortisol">cortisol</a>.<sup id="cite_ref-NieschlagBehre2010_4-7" class="reference"><a href="#cite_note-NieschlagBehre2010-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ThomasRock2012_5-16" class="reference"><a href="#cite_note-ThomasRock2012-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Binding of danazol to SHBG is considered to be more important clinically.<sup id="cite_ref-ThomasRock2012_5-17" class="reference"><a href="#cite_note-ThomasRock2012-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> By occupying SHBG and CBG, danazol increases the ratio of free to <a href="/wiki/Plasma_protein" title="Plasma protein">plasma protein</a>-bound testosterone, estradiol, progesterone, and cortisol.<sup id="cite_ref-NieschlagBehre2010_4-8" class="reference"><a href="#cite_note-NieschlagBehre2010-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ThomasRock2012_5-18" class="reference"><a href="#cite_note-ThomasRock2012-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> The table to the right shows the difference in testosterone levels in premenopausal women treated with danazol.<sup id="cite_ref-ThomasRock2012_5-19" class="reference"><a href="#cite_note-ThomasRock2012-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>As can be seen, the percentage of free testosterone is tripled in women being treated with danazol.<sup id="cite_ref-ThomasRock2012_5-20" class="reference"><a href="#cite_note-ThomasRock2012-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HelmsQuan2006_35-0" class="reference"><a href="#cite_note-HelmsQuan2006-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> The ability of danazol to increase free testosterone levels suggests that a portion of its weak androgenic effects are mediated indirectly by facilitating the activity of testosterone and <a href="/wiki/Dihydrotestosterone" title="Dihydrotestosterone">dihydrotestosterone</a> through the displacement of them from SHBG.<sup id="cite_ref-ThomasRock2012_5-21" class="reference"><a href="#cite_note-ThomasRock2012-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HelmsQuan2006_35-1" class="reference"><a href="#cite_note-HelmsQuan2006-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> In addition to binding to and occupying SHBG however, danazol also decreases the hepatic production of SHBG and therefore SHBG levels, and so downregulation of SHBG may be involved as well.<sup id="cite_ref-NieschlagBehre2010_4-9" class="reference"><a href="#cite_note-NieschlagBehre2010-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ThomasRock2012_5-22" class="reference"><a href="#cite_note-ThomasRock2012-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Danazol likely decreases hepatic production of SHBG by reducing estrogenic and increasing androgenic activity in the liver (as androgens and estrogens decrease and increase, respectively, hepatic SHBG synthesis).<sup id="cite_ref-WakelinMaibach2015_36-0" class="reference"><a href="#cite_note-WakelinMaibach2015-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> In accordance with the notion that suppression of SHBG is involved in the androgenic effects of danazol, the drug has synergistic rather than additive androgenic effects in combination with testosterone in bioassays (which is most likely secondary to the increased free testosterone levels).<sup id="cite_ref-AltchekDeligdisch2003_16-4" class="reference"><a href="#cite_note-AltchekDeligdisch2003-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>It is noteworthy that 2-hydroxymethylethisterone, a major metabolite of danazol, circulates at concentrations 5–10 times greater than those of danazol and is twice as potent as danazol in displacing testosterone from SHBG.<sup id="cite_ref-Westphal2012_37-0" class="reference"><a href="#cite_note-Westphal2012-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> As such, most of the occupation of SHBG by danazol may actually be due to this metabolite.<sup id="cite_ref-Westphal2012_37-1" class="reference"><a href="#cite_note-Westphal2012-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Antigonadotropic_activity">Antigonadotropic activity</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Danazol&action=edit&section=10" title="Edit section: Antigonadotropic activity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Via its weak progestogenic and androgenic activity, through activation of the PR and AR in the <a href="/wiki/Pituitary_gland" title="Pituitary gland">pituitary gland</a>, danazol produces <a href="/wiki/Antigonadotropic" class="mw-redirect" title="Antigonadotropic">antigonadotropic</a> effects.<sup id="cite_ref-ThomasRock2012_5-23" class="reference"><a href="#cite_note-ThomasRock2012-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Although its does not significantly affect basal <a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone">luteinizing hormone</a> (LH) and <a href="/wiki/Follicle-stimulating_hormone" title="Follicle-stimulating hormone">follicle-stimulating hormone</a> (FSH) levels in premenopausal women (and hence does not profoundly suppress <a href="/wiki/Gonadotropin" title="Gonadotropin">gonadotropin</a> or sex hormone levels like other, stronger antigonadotropins do),<sup id="cite_ref-TollisonSatterthwaite2002_38-0" class="reference"><a href="#cite_note-TollisonSatterthwaite2002-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> the drug prevents the mid-cycle surge in the levels of these hormones during the <a href="/wiki/Menstrual_cycle" title="Menstrual cycle">menstrual cycle</a>.<sup id="cite_ref-NieschlagBehre2010_4-10" class="reference"><a href="#cite_note-NieschlagBehre2010-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-AltchekDeligdisch2003_16-5" class="reference"><a href="#cite_note-AltchekDeligdisch2003-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Hoffman_23-3" class="reference"><a href="#cite_note-Hoffman-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Floyd1980_39-0" class="reference"><a href="#cite_note-Floyd1980-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Katzung2012_40-0" class="reference"><a href="#cite_note-Katzung2012-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> By doing this, it suppresses increases in estrogen and progesterone levels at this time and prevents <a href="/wiki/Ovulation" title="Ovulation">ovulation</a>.<sup id="cite_ref-AltchekDeligdisch2003_16-6" class="reference"><a href="#cite_note-AltchekDeligdisch2003-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Hoffman_23-4" class="reference"><a href="#cite_note-Hoffman-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Floyd1980_39-1" class="reference"><a href="#cite_note-Floyd1980-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Katzung2012_40-1" class="reference"><a href="#cite_note-Katzung2012-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Mechanism_of_action_in_endometriosis">Mechanism of action in endometriosis</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Danazol&action=edit&section=11" title="Edit section: Mechanism of action in endometriosis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Because danazol reduces estrogen production and levels,<sup id="cite_ref-TollisonSatterthwaite2002_38-1" class="reference"><a href="#cite_note-TollisonSatterthwaite2002-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> it has functional <a href="/wiki/Antiestrogen" title="Antiestrogen">antiestrogenic</a> properties.<sup id="cite_ref-Taylor1998_41-0" class="reference"><a href="#cite_note-Taylor1998-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> The combination of its antiestrogenic, androgenic, and progestogenic or <a href="/wiki/Antiprogestogen" title="Antiprogestogen">antiprogestogenic</a> actions cause <a href="/wiki/Atrophy" title="Atrophy">atrophy</a> of the <a href="/wiki/Endometrium" title="Endometrium">endometrium</a>, which alleviates the symptoms of endometriosis.<sup id="cite_ref-NieschlagBehre2010_4-11" class="reference"><a href="#cite_note-NieschlagBehre2010-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ThomasRock2012_5-24" class="reference"><a href="#cite_note-ThomasRock2012-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-AltchekDeligdisch2003_16-7" class="reference"><a href="#cite_note-AltchekDeligdisch2003-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-TollisonSatterthwaite2002_38-2" class="reference"><a href="#cite_note-TollisonSatterthwaite2002-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Fedele1990_42-0" class="reference"><a href="#cite_note-Fedele1990-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Effects_in_men">Effects in men</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Danazol&action=edit&section=12" title="Edit section: Effects in men"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In men, danazol has been found to inhibit gonadotropin secretion and markedly decrease testosterone levels, likely due to its actions as a steroidogenesis inhibitor and antigonadotropin.<sup id="cite_ref-pmid4422449_43-0" class="reference"><a href="#cite_note-pmid4422449-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> However, even at the highest dosage assessed (800 mg/day), <a href="/wiki/Spermatogenesis" title="Spermatogenesis">spermatogenesis</a> remained unaffected.<sup id="cite_ref-pmid4422449_43-1" class="reference"><a href="#cite_note-pmid4422449-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Pharmacokinetics">Pharmacokinetics</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Danazol&action=edit&section=13" title="Edit section: Pharmacokinetics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> of danazol is low.<sup id="cite_ref-Dörwald2013_7-1" class="reference"><a href="#cite_note-Dörwald2013-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> In addition, circulating levels of danazol do not increase proportionally with increasing doses, indicating that there is a saturation of bioavailability.<sup id="cite_ref-DanocrineLabel_2-8" class="reference"><a href="#cite_note-DanocrineLabel-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> With single-dose administration, it has been found that a 4-fold increase in dosage of danazol increased <a href="/wiki/Tmax_(pharmacology)" class="mw-redirect" title="Tmax (pharmacology)">peak levels</a> only by 1.3- and 2.2-fold and <a href="/wiki/Area-under-curve_(pharmacokinetics)" class="mw-redirect" title="Area-under-curve (pharmacokinetics)">area-under-the-curve levels</a> by 1.6- and 2.5-fold in the fasted and fed states, respectively.<sup id="cite_ref-DanocrineLabel_2-9" class="reference"><a href="#cite_note-DanocrineLabel-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Similar findings were observed for chronic administration.<sup id="cite_ref-DanocrineLabel_2-10" class="reference"><a href="#cite_note-DanocrineLabel-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Intake of danazol with food (>30 grams of fat) has been found to increase the bioavailability and peak levels of danazol by 3- to 4-fold with a single dose and by 2- to 2.5-fold with chronic administration.<sup id="cite_ref-DanocrineLabel_2-11" class="reference"><a href="#cite_note-DanocrineLabel-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Following administration of danazol, peak concentrations occur after 2 to 8 hours, with a median of 4 hours.<sup id="cite_ref-DanocrineLabel_2-12" class="reference"><a href="#cite_note-DanocrineLabel-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Steady_state_(pharmacokinetics)" class="mw-redirect" title="Steady state (pharmacokinetics)">Steady-state levels</a> of danazol are achieved after 6 days of twice-daily administration.<sup id="cite_ref-DanocrineLabel_2-13" class="reference"><a href="#cite_note-DanocrineLabel-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Danazol is <a href="/wiki/Lipophilic" class="mw-redirect" title="Lipophilic">lipophilic</a> and can partition into <a href="/wiki/Cell_membrane" title="Cell membrane">cell membranes</a>, which indicates that it is likely to <a href="/wiki/Distribution_(pharmacology)" title="Distribution (pharmacology)">distribute</a> deeply into <a href="/wiki/Tissue_(biology)" title="Tissue (biology)">tissue</a> compartments.<sup id="cite_ref-DanocrineLabel_2-14" class="reference"><a href="#cite_note-DanocrineLabel-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Volume_of_distribution" title="Volume of distribution">volume of distribution</a> of danazol is 3.4 L.<sup id="cite_ref-Dörwald2013_7-2" class="reference"><a href="#cite_note-Dörwald2013-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Danazol is known to be <a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">plasma protein bound</a> to <a href="/wiki/Human_serum_albumin" title="Human serum albumin">albumin</a>, SHBG, and CBG.<sup id="cite_ref-GriffinD'Arcy1997_3-1" class="reference"><a href="#cite_note-GriffinD'Arcy1997-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-NieschlagBehre2010_4-12" class="reference"><a href="#cite_note-NieschlagBehre2010-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ThomasRock2012_5-25" class="reference"><a href="#cite_note-ThomasRock2012-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>Danazol is <a href="/wiki/Metabolism" title="Metabolism">metabolized</a> in the <a href="/wiki/Liver" title="Liver">liver</a> by <a href="/wiki/Enzyme" title="Enzyme">enzymes</a> such as <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a>.<sup id="cite_ref-Martindale2013_9-5" class="reference"><a href="#cite_note-Martindale2013-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-LemkeWilliams2012_6-2" class="reference"><a href="#cite_note-LemkeWilliams2012-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Its <a href="/wiki/Elimination_half-life" class="mw-redirect" title="Elimination half-life">elimination half-life</a> has varied across studies, but has been found to be 3 to 10 hours after a single dose and 24 to 26 hours with repeated administration.<sup id="cite_ref-Martindale2013_9-6" class="reference"><a href="#cite_note-Martindale2013-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-DanocrineLabel_2-15" class="reference"><a href="#cite_note-DanocrineLabel-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> The major <a href="/wiki/Metabolite" title="Metabolite">metabolites</a> of danazol are 2-hydroxymethylethisterone (also known as 2-hydroxymethyldanazol; formed by CYP3A4 and described as inactive) and <a href="/wiki/Ethisterone" title="Ethisterone">ethisterone</a> (a progestogen and androgen),<sup id="cite_ref-LemkeWilliams2012_6-3" class="reference"><a href="#cite_note-LemkeWilliams2012-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-DanocrineLabel_2-16" class="reference"><a href="#cite_note-DanocrineLabel-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Dörwald2013_7-3" class="reference"><a href="#cite_note-Dörwald2013-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MozayaniRaymon2011_44-0" class="reference"><a href="#cite_note-MozayaniRaymon2011-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> and other, minor metabolites include δ<sup>2</sup>-hydroxymethylethisterone, 6β-hydroxy-2-hydroxymethylethisterone, and δ<sup>1</sup>-6β-hydroxy-2-hydroxymethylethisterone.<sup id="cite_ref-AzolLabel_45-0" class="reference"><a href="#cite_note-AzolLabel-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> At least 10 different metabolites have been identified.<sup id="cite_ref-DanocrineLabel_2-17" class="reference"><a href="#cite_note-DanocrineLabel-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Danazol is <a href="/wiki/Elimination_(pharmacology)" title="Elimination (pharmacology)">eliminated</a> in <a href="/wiki/Urine" title="Urine">urine</a> and <a href="/wiki/Feces" title="Feces">feces</a>, with the two primary metabolites in urine being 2-hydroxymethylethisterone and ethisterone.<sup id="cite_ref-DanocrineLabel_2-18" class="reference"><a href="#cite_note-DanocrineLabel-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Danazol&action=edit&section=14" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/List_of_androgens/anabolic_steroids" class="mw-redirect" title="List of androgens/anabolic steroids">List of androgens/anabolic steroids</a> and <a href="/wiki/List_of_progestogens" title="List of progestogens">List of progestogens</a></div> <p>Danazol, also known as 2,3-isoxazol-17α-ethynyltestosterone or as 17α-ethynyl-17β-hydroxyandrost-4-en-[2,3-d]isoxazole, is a <a href="/wiki/Synthetic_compound" class="mw-redirect" title="Synthetic compound">synthetic</a> <a href="/wiki/Androstane" title="Androstane">androstane</a> <a href="/wiki/Steroid" title="Steroid">steroid</a> and a <a href="/wiki/Chemical_derivative" class="mw-redirect" title="Chemical derivative">derivative</a> of <a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">testosterone</a> and <a href="/wiki/Ethisterone" title="Ethisterone">ethisterone</a> (17α-ethynyltestosterone).<sup id="cite_ref-Elks2014_10-1" class="reference"><a href="#cite_note-Elks2014-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-IndexNominum2000_11-1" class="reference"><a href="#cite_note-IndexNominum2000-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid4422449_43-2" class="reference"><a href="#cite_note-pmid4422449-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> It is specifically the derivative of ethisterone where the C3 <a href="/wiki/Ketone" title="Ketone">ketone</a> is replaced with a 2,3-<a href="/wiki/Isoxazole" title="Isoxazole">isoxazole</a> <a href="/wiki/Moiety_(chemistry)" title="Moiety (chemistry)">moiety</a> (i.e., an isoxazole ring is fused to the A ring at the C2 and C3 positions).<sup id="cite_ref-LemkeWilliams2012_6-4" class="reference"><a href="#cite_note-LemkeWilliams2012-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-JonesRock2015_14-6" class="reference"><a href="#cite_note-JonesRock2015-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Ethisterone is a weak <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestin</a> with weak androgenic activity.<sup id="cite_ref-Kadam2007_46-0" class="reference"><a href="#cite_note-Kadam2007-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Danazol&action=edit&section=15" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Danazol was <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">synthesized</a> in 1963 by a team of scientists at <a href="/wiki/Sterling_Drug" title="Sterling Drug">Sterling Winthrop</a> in <a href="/wiki/Rensselaer,_New_York" title="Rensselaer, New York">Rensselaer, New York</a> by a team that included Helmutt Neumann, Gordon Potts, W.T. Ryan, and Frederik W. Stonner.<sup id="cite_ref-NeumannPotts1979_17-1" class="reference"><a href="#cite_note-NeumannPotts1979-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-EliasGwinup1983_18-1" class="reference"><a href="#cite_note-EliasGwinup1983-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> It was approved by the <a href="/wiki/United_States" title="United States"><abbr title="United States">U.S.</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip United States</span> <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> in 1971 as the first drug in the country to specifically treat endometriosis.<sup id="cite_ref-JonesRock2015_14-7" class="reference"><a href="#cite_note-JonesRock2015-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Dmowski1971_19-1" class="reference"><a href="#cite_note-Dmowski1971-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Danazol&action=edit&section=16" title="Edit section: Society and culture"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Generic_names">Generic names</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Danazol&action=edit&section=17" title="Edit section: Generic names"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><i>Danazol</i> is the <a href="/wiki/Generic_term" class="mw-redirect" title="Generic term">generic name</a> of the drug and its <a href="/wiki/International_Nonproprietary_Name" class="mw-redirect" title="International Nonproprietary Name"><abbr title="International Nonproprietary Name">INN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip International Nonproprietary Name</span>, <a href="/wiki/United_States_Adopted_Name" title="United States Adopted Name"><abbr title="United States Adopted Name">USAN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip United States Adopted Name</span>, <a href="/wiki/United_States_Pharmacopeia" title="United States Pharmacopeia"><abbr title="United States Pharmacopeia">USP</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip United States Pharmacopeia</span>, <a href="/wiki/British_Approved_Name" title="British Approved Name"><abbr title="British Approved Name">BAN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip British Approved Name</span>, <a href="/wiki/D%C3%A9nomination_Commune_Fran%C3%A7aise" title="Dénomination Commune Française"><abbr title="Dénomination Commune Française">DCF</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Dénomination Commune Française</span>, <a href="/wiki/Denominazione_Comune_Italiana" title="Denominazione Comune Italiana"><abbr title="Denominazione Comune Italiana">DCIT</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Denominazione Comune Italiana</span>, and <a href="/wiki/Japanese_Accepted_Name" title="Japanese Accepted Name"><abbr title="Japanese Accepted Name">JAN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Japanese Accepted Name</span>.<sup id="cite_ref-Martindale2013_9-7" class="reference"><a href="#cite_note-Martindale2013-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Elks2014_10-2" class="reference"><a href="#cite_note-Elks2014-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-IndexNominum2000_11-2" class="reference"><a href="#cite_note-IndexNominum2000-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MortonHall2012_12-1" class="reference"><a href="#cite_note-MortonHall2012-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Drugs.com_47-0" class="reference"><a href="#cite_note-Drugs.com-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> It is also known by its developmental code name <i>WIN-17757</i>.<sup id="cite_ref-Martindale2013_9-8" class="reference"><a href="#cite_note-Martindale2013-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Elks2014_10-3" class="reference"><a href="#cite_note-Elks2014-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-IndexNominum2000_11-3" class="reference"><a href="#cite_note-IndexNominum2000-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MortonHall2012_12-2" class="reference"><a href="#cite_note-MortonHall2012-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Drugs.com_47-1" class="reference"><a href="#cite_note-Drugs.com-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Brand_names">Brand names</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Danazol&action=edit&section=18" title="Edit section: Brand names"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Danazol is or has been marketed under many brand names throughout the world including Anargil, Azol, Benzol, Bonzol, Cyclolady, Cyclomen, Danal, Danalol, Danamet, Danamin, Danasin, Danatrol, Danazant, Danazol, Danocrine, Danodiol, Danogen, Danokrin, Danol, Danonice, Danoval, Danzol, Dogalact (<a href="/wiki/Veterinary_drug" class="mw-redirect" title="Veterinary drug">veterinary</a>), Dorink, Dzol, Ectopal, Elle, Gonablok, Gong Fu Yi Kang, Gynadom, Kodazol, Kupdina, Ladogal, Lozana, Mastodanatrol, Nazol, Norciden, Vabon, and Winobanin.<sup id="cite_ref-Martindale2013_9-9" class="reference"><a href="#cite_note-Martindale2013-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Elks2014_10-4" class="reference"><a href="#cite_note-Elks2014-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-IndexNominum2000_11-4" class="reference"><a href="#cite_note-IndexNominum2000-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MortonHall2012_12-3" class="reference"><a href="#cite_note-MortonHall2012-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Drugs.com_47-2" class="reference"><a href="#cite_note-Drugs.com-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Availability">Availability</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Danazol&action=edit&section=19" title="Edit section: Availability"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Danazol is available in the <a href="/wiki/United_States" title="United States">United States</a>, <a href="/wiki/Europe" title="Europe">Europe</a>, and widely elsewhere throughout the world.<sup id="cite_ref-Martindale2013_9-10" class="reference"><a href="#cite_note-Martindale2013-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-IndexNominum2000_11-5" class="reference"><a href="#cite_note-IndexNominum2000-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Drugs.com_47-3" class="reference"><a href="#cite_note-Drugs.com-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Danazol&action=edit&section=20" title="Edit section: Research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Danazol has been studied in the treatment of <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a> in women, but produced relatively low <a href="/wiki/Response_rate_(medicine)" class="mw-redirect" title="Response rate (medicine)">response rates</a> of about 15 to 20%.<sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-PistersBrennan2013_49-0" class="reference"><a href="#cite_note-PistersBrennan2013-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> </p><p>Low-dose danazol has been investigated in the treatment of <a href="/wiki/Diabetic_macular_edema" class="mw-redirect" title="Diabetic macular edema">diabetic macular edema</a> in a <a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">phase III</a> <a href="/wiki/Clinical_trial" title="Clinical trial">clinical trial</a>.<sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> </p><p>A 2016 phase I/II prospective study orally administered 800 mg per day to 27 patients with <a href="/wiki/Telomere" title="Telomere">telomere</a> diseases. The primary efficacy endpoint was a 20% reduction in the annual rate of telomere attrition measured. Toxic effects formed the primary safety endpoint. The study was halted early, after telomere attrition was reduced in all 12 patients who could be evaluated. 12 of 27 patients achieved the primary efficacy end point, 11 of whom increased telomere length at 24 months. <a href="/wiki/Hematology" title="Hematology">Hematologic</a> responses (secondary efficacy endpoint) occurred in 10 of 12 patients who could be evaluated at 24 months. Elevated liver-enzyme levels and muscle cramps (known adverse effects) of grade 2 or less occurred in 41% and 33% of the patients, respectively.<sup id="cite_ref-pmid27192671_52-0" class="reference"><a href="#cite_note-pmid27192671-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Danazol&action=edit&section=21" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-FDA-AllBoxedWarnings-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-FDA-AllBoxedWarnings_1-0">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://nctr-crs.fda.gov/fdalabel/ui/spl-summaries/criteria/343802">"FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)"</a>. <i>nctr-crs.fda.gov</i>. <a href="/wiki/FDA" class="mw-redirect" title="FDA">FDA</a><span class="reference-accessdate">. Retrieved <span class="nowrap">22 Oct</span> 2023</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=nctr-crs.fda.gov&rft.atitle=FDA-sourced+list+of+all+drugs+with+black+box+warnings+%28Use+Download+Full+Results+and+View+Query+links.%29&rft_id=https%3A%2F%2Fnctr-crs.fda.gov%2Ffdalabel%2Fui%2Fspl-summaries%2Fcriteria%2F343802&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADanazol" class="Z3988"></span></span> </li> <li id="cite_note-DanocrineLabel-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-DanocrineLabel_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-DanocrineLabel_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-DanocrineLabel_2-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-DanocrineLabel_2-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-DanocrineLabel_2-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-DanocrineLabel_2-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-DanocrineLabel_2-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-DanocrineLabel_2-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-DanocrineLabel_2-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-DanocrineLabel_2-9"><sup><i><b>j</b></i></sup></a> <a href="#cite_ref-DanocrineLabel_2-10"><sup><i><b>k</b></i></sup></a> <a href="#cite_ref-DanocrineLabel_2-11"><sup><i><b>l</b></i></sup></a> <a href="#cite_ref-DanocrineLabel_2-12"><sup><i><b>m</b></i></sup></a> <a href="#cite_ref-DanocrineLabel_2-13"><sup><i><b>n</b></i></sup></a> <a href="#cite_ref-DanocrineLabel_2-14"><sup><i><b>o</b></i></sup></a> <a href="#cite_ref-DanocrineLabel_2-15"><sup><i><b>p</b></i></sup></a> <a href="#cite_ref-DanocrineLabel_2-16"><sup><i><b>q</b></i></sup></a> <a href="#cite_ref-DanocrineLabel_2-17"><sup><i><b>r</b></i></sup></a> <a href="#cite_ref-DanocrineLabel_2-18"><sup><i><b>s</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/017557s033s039s040s041s042lbl.pdf">"Danocrine Brand of Danazol Capsules, USP"</a> <span class="cs1-format">(PDF)</span>. <i>Sanofi-Aventis U.S. LLC</i>. U.S. Food and Drug Administration.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Sanofi-Aventis+U.S.+LLC&rft.atitle=Danocrine+Brand+of+Danazol+Capsules%2C+USP&rft_id=https%3A%2F%2Fwww.accessdata.fda.gov%2Fdrugsatfda_docs%2Flabel%2F2011%2F017557s033s039s040s041s042lbl.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADanazol" class="Z3988"></span></span> </li> <li id="cite_note-GriffinD'Arcy1997-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-GriffinD'Arcy1997_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-GriffinD'Arcy1997_3-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFGriffinD'Arcy1997" class="citation book cs1">Griffin JP, D'Arcy PF (17 November 1997). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=rmx2fLEdZvwC&pg=PA194"><i>A Manual of Adverse Drug Interactions</i></a>. Elsevier. pp. 194–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-08-052583-9" title="Special:BookSources/978-0-08-052583-9"><bdi>978-0-08-052583-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=A+Manual+of+Adverse+Drug+Interactions&rft.pages=194-&rft.pub=Elsevier&rft.date=1997-11-17&rft.isbn=978-0-08-052583-9&rft.aulast=Griffin&rft.aufirst=JP&rft.au=D%27Arcy%2C+PF&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Drmx2fLEdZvwC%26pg%3DPA194&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADanazol" class="Z3988"></span></span> </li> <li id="cite_note-NieschlagBehre2010-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-NieschlagBehre2010_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-NieschlagBehre2010_4-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-NieschlagBehre2010_4-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-NieschlagBehre2010_4-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-NieschlagBehre2010_4-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-NieschlagBehre2010_4-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-NieschlagBehre2010_4-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-NieschlagBehre2010_4-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-NieschlagBehre2010_4-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-NieschlagBehre2010_4-9"><sup><i><b>j</b></i></sup></a> <a href="#cite_ref-NieschlagBehre2010_4-10"><sup><i><b>k</b></i></sup></a> <a href="#cite_ref-NieschlagBehre2010_4-11"><sup><i><b>l</b></i></sup></a> <a href="#cite_ref-NieschlagBehre2010_4-12"><sup><i><b>m</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFNieschlagBehreNieschlag2010" class="citation book cs1">Nieschlag E, Behre HM, Nieschlag S (13 January 2010). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=mEgckDNkonUC&pg=PA426"><i>Andrology: Male Reproductive Health and Dysfunction</i></a>. Springer Science & Business Media. pp. <span class="nowrap">426–</span>428. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-540-78355-8" title="Special:BookSources/978-3-540-78355-8"><bdi>978-3-540-78355-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Andrology%3A+Male+Reproductive+Health+and+Dysfunction&rft.pages=%3Cspan+class%3D%22nowrap%22%3E426-%3C%2Fspan%3E428&rft.pub=Springer+Science+%26+Business+Media&rft.date=2010-01-13&rft.isbn=978-3-540-78355-8&rft.aulast=Nieschlag&rft.aufirst=E&rft.au=Behre%2C+HM&rft.au=Nieschlag%2C+S&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DmEgckDNkonUC%26pg%3DPA426&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADanazol" class="Z3988"></span></span> </li> <li id="cite_note-ThomasRock2012-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-ThomasRock2012_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-ThomasRock2012_5-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-ThomasRock2012_5-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-ThomasRock2012_5-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-ThomasRock2012_5-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-ThomasRock2012_5-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-ThomasRock2012_5-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-ThomasRock2012_5-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-ThomasRock2012_5-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-ThomasRock2012_5-9"><sup><i><b>j</b></i></sup></a> <a href="#cite_ref-ThomasRock2012_5-10"><sup><i><b>k</b></i></sup></a> <a href="#cite_ref-ThomasRock2012_5-11"><sup><i><b>l</b></i></sup></a> <a href="#cite_ref-ThomasRock2012_5-12"><sup><i><b>m</b></i></sup></a> <a href="#cite_ref-ThomasRock2012_5-13"><sup><i><b>n</b></i></sup></a> <a href="#cite_ref-ThomasRock2012_5-14"><sup><i><b>o</b></i></sup></a> <a href="#cite_ref-ThomasRock2012_5-15"><sup><i><b>p</b></i></sup></a> <a href="#cite_ref-ThomasRock2012_5-16"><sup><i><b>q</b></i></sup></a> <a href="#cite_ref-ThomasRock2012_5-17"><sup><i><b>r</b></i></sup></a> <a href="#cite_ref-ThomasRock2012_5-18"><sup><i><b>s</b></i></sup></a> <a href="#cite_ref-ThomasRock2012_5-19"><sup><i><b>t</b></i></sup></a> <a href="#cite_ref-ThomasRock2012_5-20"><sup><i><b>u</b></i></sup></a> <a href="#cite_ref-ThomasRock2012_5-21"><sup><i><b>v</b></i></sup></a> <a href="#cite_ref-ThomasRock2012_5-22"><sup><i><b>w</b></i></sup></a> <a href="#cite_ref-ThomasRock2012_5-23"><sup><i><b>x</b></i></sup></a> <a href="#cite_ref-ThomasRock2012_5-24"><sup><i><b>y</b></i></sup></a> <a href="#cite_ref-ThomasRock2012_5-25"><sup><i><b>z</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFThomasRock2012" class="citation book cs1">Thomas EJ, Rock J (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=AFP1CAAAQBAJ&pg=PA241"><i>Modern Approaches to Endometriosis</i></a>. Springer Science & Business Media. pp. <span class="nowrap">239–</span>256. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-94-011-3864-2" title="Special:BookSources/978-94-011-3864-2"><bdi>978-94-011-3864-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Modern+Approaches+to+Endometriosis&rft.pages=%3Cspan+class%3D%22nowrap%22%3E239-%3C%2Fspan%3E256&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-94-011-3864-2&rft.aulast=Thomas&rft.aufirst=EJ&rft.au=Rock%2C+J&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DAFP1CAAAQBAJ%26pg%3DPA241&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADanazol" class="Z3988"></span></span> </li> <li id="cite_note-LemkeWilliams2012-6"><span class="mw-cite-backlink">^ <a href="#cite_ref-LemkeWilliams2012_6-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-LemkeWilliams2012_6-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-LemkeWilliams2012_6-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-LemkeWilliams2012_6-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-LemkeWilliams2012_6-4"><sup><i><b>e</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLemkeWilliams2012" class="citation book cs1">Lemke TL, Williams DA (24 January 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=Sd6ot9ul-bUC&pg=PA1361"><i>Foye's Principles of Medicinal Chemistry</i></a>. Lippincott Williams & Wilkins. pp. 1361–. <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=book&rft.btitle=Foye%27s+Principles+of+Medicinal+Chemistry&rft.pages=1361-&rft.pub=Lippincott+Williams+%26+Wilkins&rft.date=2012-01-24&rft.isbn=978-1-60913-345-0&rft.aulast=Lemke&rft.aufirst=TL&rft.au=Williams%2C+DA&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DSd6ot9ul-bUC%26pg%3DPA1361&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADanazol" class="Z3988"></span></span> </li> <li id="cite_note-Dörwald2013-7"><span class="mw-cite-backlink">^ <a href="#cite_ref-Dörwald2013_7-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Dörwald2013_7-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Dörwald2013_7-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Dörwald2013_7-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDörwald2013" class="citation book cs1">Dörwald FZ (4 February 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=YTeY9ZEfNccC&pg=PA485"><i>Lead Optimization for Medicinal Chemists: Pharmacokinetic Properties of Functional Groups and Organic Compounds</i></a>. 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Springer Science & Business Media. pp. 390–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4757-3889-6" title="Special:BookSources/978-1-4757-3889-6"><bdi>978-1-4757-3889-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Blaustein%27s+Pathology+of+the+Female+Genital+Tract&rft.pages=390-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2013-04-17&rft.isbn=978-1-4757-3889-6&rft.aulast=Kurman&rft.aufirst=RJ&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DsM3eBwAAQBAJ%26pg%3DPA390&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADanazol" class="Z3988"></span></span> </li> <li id="cite_note-Martindale2013-9"><span class="mw-cite-backlink">^ <a href="#cite_ref-Martindale2013_9-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Martindale2013_9-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Martindale2013_9-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Martindale2013_9-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Martindale2013_9-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-Martindale2013_9-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-Martindale2013_9-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-Martindale2013_9-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-Martindale2013_9-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-Martindale2013_9-9"><sup><i><b>j</b></i></sup></a> <a href="#cite_ref-Martindale2013_9-10"><sup><i><b>k</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBrayfield2013" class="citation web cs1">Brayfield A, ed. 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January 2000. pp. 293–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-88763-075-1" title="Special:BookSources/978-3-88763-075-1"><bdi>978-3-88763-075-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Index+Nominum+2000%3A+International+Drug+Directory&rft.pages=293-&rft.pub=Taylor+%26+Francis&rft.date=2000-01&rft.isbn=978-3-88763-075-1&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D5GpcTQD_L2oC%26pg%3DPA293&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADanazol" class="Z3988"></span></span> </li> <li id="cite_note-MortonHall2012-12"><span class="mw-cite-backlink">^ <a href="#cite_ref-MortonHall2012_12-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-MortonHall2012_12-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-MortonHall2012_12-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-MortonHall2012_12-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMortonHall2012" class="citation book cs1">Morton IK, Hall JM (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA91"><i>Concise Dictionary of Pharmacological Agents: Properties and Synonyms</i></a>. Springer Science & Business Media. pp. 91–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-94-011-4439-1" title="Special:BookSources/978-94-011-4439-1"><bdi>978-94-011-4439-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Concise+Dictionary+of+Pharmacological+Agents%3A+Properties+and+Synonyms&rft.pages=91-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-94-011-4439-1&rft.aulast=Morton&rft.aufirst=IK&rft.au=Hall%2C+JM&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DtsjrCAAAQBAJ%26pg%3DPA91&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADanazol" class="Z3988"></span></span> </li> <li id="cite_note-Farquhar2007-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-Farquhar2007_13-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSelakFarquharPrenticeSingla2007" class="citation journal cs1">Selak V, Farquhar C, Prentice A, Singla A (October 2007). 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"Danazol for pelvic pain associated with endometriosis". <i>The Cochrane Database of Systematic Reviews</i> (4): CD000068. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14651858.CD000068.pub2">10.1002/14651858.CD000068.pub2</a>. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://hdl.handle.net/2292%2F28213">2292/28213</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/17943735">17943735</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Cochrane+Database+of+Systematic+Reviews&rft.atitle=Danazol+for+pelvic+pain+associated+with+endometriosis&rft.issue=4&rft.pages=CD000068&rft.date=2007-10&rft_id=info%3Ahdl%2F2292%2F28213&rft_id=info%3Apmid%2F17943735&rft_id=info%3Adoi%2F10.1002%2F14651858.CD000068.pub2&rft.aulast=Selak&rft.aufirst=V&rft.au=Farquhar%2C+C&rft.au=Prentice%2C+A&rft.au=Singla%2C+A&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADanazol" class="Z3988"></span></span> </li> <li id="cite_note-JonesRock2015-14"><span class="mw-cite-backlink">^ <a href="#cite_ref-JonesRock2015_14-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-JonesRock2015_14-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-JonesRock2015_14-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-JonesRock2015_14-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-JonesRock2015_14-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-JonesRock2015_14-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-JonesRock2015_14-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-JonesRock2015_14-7"><sup><i><b>h</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFJonesRock2015" class="citation book cs1">Jones HW, Rock JA (10 July 2015). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=iK4kCgAAQBAJ&pg=PT1327"><i>Te Linde's Operative Gynecology</i></a>. 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Retrieved <span class="nowrap">27 June</span> 2015</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Ampio+Pharmaceuticals+Announces+Additional+Statistically+Significant+Study+Results+for+Optina%E2%84%A2+in+the+Treatment+of+Diabetic+Macular+Edema+%28DME%29&rft_id=http%3A%2F%2Fampiopharma.com%2Fnews%2Fampio-pharmaceuticals-announces-additional-statistically-significant-study-results-for-optina-in-the-treatment-of-diabetic-macular-edema-dme%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADanazol" class="Z3988"></span></span> </li> <li id="cite_note-pmid27192671-52"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid27192671_52-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFTownsleyDumitriuLiuBiancotto2016" class="citation journal cs1">Townsley DM, Dumitriu B, Liu D, Biancotto A, Weinstein B, Chen C, et al. 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"Endocrine properties and clinical application of danazol". <i>Fertility and Sterility</i>. <b>31</b> (3): <span class="nowrap">237–</span>251. <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%2943869-0">10.1016/S0015-0282(16)43869-0</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/374128">374128</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=Endocrine+properties+and+clinical+application+of+danazol&rft.volume=31&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E237-%3C%2Fspan%3E251&rft.date=1979-03&rft_id=info%3Adoi%2F10.1016%2FS0015-0282%2816%2943869-0&rft_id=info%3Apmid%2F374128&rft.aulast=Dmowski&rft.aufirst=WP&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADanazol" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFraser1979" class="citation journal cs1">Fraser IS (April 1979). 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ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Androgens_and_antiandrogens" title="Template:Androgens and antiandrogens"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Androgens_and_antiandrogens" title="Template talk:Androgens and antiandrogens"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Androgens_and_antiandrogens" title="Special:EditPage/Template:Androgens and antiandrogens"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Androgens_and_antiandrogens491" style="font-size:114%;margin:0 4em"><a href="/wiki/Androgen" title="Androgen">Androgens</a> and <a href="/wiki/Antiandrogen" title="Antiandrogen">antiandrogens</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Androgen" title="Androgen">Androgens</a><br />(incl. <a href="/wiki/Anabolic%E2%80%93androgenic_steroid" class="mw-redirect" title="Anabolic–androgenic steroid"><abbr title="anabolic–androgenic steroid">AAS</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 anabolic–androgenic steroid</span>)</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:9em;;text-align:center;"><a href="/wiki/Androgen_receptor" title="Androgen receptor"><abbr title="Androgen receptor">AR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Androgen receptor</span> <a href="/wiki/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><i>Testosterone derivatives:</i> <a href="/wiki/Androstenediol_dipropionate" title="Androstenediol dipropionate">Androstenediol dipropionate</a></li> <li><a href="/wiki/Boldenone_undecylenate" title="Boldenone undecylenate">Boldenone undecylenate</a></li> <li><a href="/wiki/Clostebol" title="Clostebol">Clostebol</a></li> <li><a href="/wiki/Clostebol_acetate" title="Clostebol acetate">Clostebol acetate</a></li> <li><a href="/wiki/Clostebol_caproate" title="Clostebol caproate">Clostebol caproate</a></li> <li><a href="/wiki/Clostebol_propionate" title="Clostebol propionate">Clostebol propionate</a></li> <li><a href="/wiki/Cloxotestosterone_acetate" title="Cloxotestosterone acetate">Cloxotestosterone acetate</a></li> <li><a href="/wiki/Prasterone" title="Prasterone">Prasterone (dehydroepiandrosterone, DHEA)</a></li> <li><a href="/wiki/Prasterone_enanthate" title="Prasterone enanthate">Prasterone enanthate (DHEA enanthate)</a></li> <li><a href="/wiki/Prasterone_sulfate" title="Prasterone sulfate">Prasterone sulfate (DHEA sulfate)</a></li> <li><a href="/wiki/Quinbolone" title="Quinbolone">Quinbolone</a></li> <li><a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">Testosterone</a><sup>#</sup></li> <li><a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">Testosterone esters</a> (e.g., <a href="/wiki/Testosterone_cypionate" title="Testosterone cypionate">testosterone cypionate</a>, <a href="/wiki/Testosterone_enanthate" title="Testosterone enanthate">testosterone enanthate</a>, <a href="/wiki/Testosterone_propionate" title="Testosterone propionate">testosterone propionate</a>, <a href="/wiki/Testosterone_undecanoate" title="Testosterone undecanoate">testosterone undecanoate</a>, <a href="/wiki/Testosterone_ester_mixture" class="mw-redirect" title="Testosterone ester mixture">testosterone ester mixtures</a> (<a href="/wiki/Deposterona" class="mw-redirect" title="Deposterona">Deposterona</a>, <a href="/wiki/Omnadren" class="mw-redirect" title="Omnadren">Omnadren</a>, <a href="/wiki/Testosterone_propionate/testosterone_phenylpropionate/testosterone_isocaproate/testosterone_decanoate" title="Testosterone propionate/testosterone phenylpropionate/testosterone isocaproate/testosterone decanoate">Sustanon</a>, <a href="/wiki/Testoviron_depot" class="mw-redirect" title="Testoviron depot">Testoviron Depot</a>))</li></ul> <ul><li><i>Dihydrotestosterone derivatives:</i> <a href="/wiki/Androstanolone" title="Androstanolone">Androstanolone (stanolone, dihydrotestosterone, DHT)</a></li> <li><a href="/wiki/List_of_androgen_esters#Dihydrotestosterone_esters" title="List of androgen esters">Androstanolone esters</a></li> <li><a href="/wiki/Bolazine_capronate" title="Bolazine capronate">Bolazine capronate</a></li> <li><a href="/wiki/Drostanolone_propionate" title="Drostanolone propionate">Drostanolone propionate (dromostanolone propionate)</a></li> <li><a href="/wiki/Epitiostanol" title="Epitiostanol">Epitiostanol</a></li> <li><a href="/wiki/Mepitiostane" title="Mepitiostane">Mepitiostane</a></li> <li><a href="/wiki/Mesterolone" title="Mesterolone">Mesterolone</a></li> <li><a href="/wiki/Metenolone_acetate" title="Metenolone acetate">Metenolone acetate (methenolone acetate)</a></li> <li><a href="/wiki/Metenolone_enanthate" title="Metenolone enanthate">Metenolone enanthate (methenolone enanthate)</a></li> <li><a href="/wiki/Stenbolone_acetate" title="Stenbolone acetate">Stenbolone acetate</a></li></ul> <ul><li><i>19-Nortestosterone derivatives:</i> <a href="/wiki/Bolandiol_dipropionate" title="Bolandiol dipropionate">Bolandiol dipropionate</a></li> <li><a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">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/Norclostebol" title="Norclostebol">Norclostebol</a></li> <li><a href="/wiki/Norclostebol_acetate" title="Norclostebol acetate">Norclostebol acetate</a></li> <li><a href="/wiki/Oxabolone_cipionate" title="Oxabolone cipionate">Oxabolone cipionate (oxabolone cypionate)</a></li> <li><a href="/wiki/Trenbolone_acetate" title="Trenbolone acetate">Trenbolone acetate</a></li> <li><a href="/wiki/Trenbolone_hexahydrobenzylcarbonate" title="Trenbolone hexahydrobenzylcarbonate">Trenbolone hexahydrobenzylcarbonate (trenbolone cyclohexylmethylcarbonate)</a></li></ul> <ul><li><i>17α-Alkylated testosterone derivatives:</i> <a href="/wiki/Bolasterone" title="Bolasterone">Bolasterone</a></li> <li><a href="/wiki/Calusterone" title="Calusterone">Calusterone</a></li> <li><a href="/wiki/Chlorodehydromethyltestosterone" title="Chlorodehydromethyltestosterone">Chlorodehydromethyltestosterone (CDMT)</a></li> <li><a href="/wiki/Fluoxymesterone" title="Fluoxymesterone">Fluoxymesterone</a></li> <li><a href="/wiki/Formebolone" title="Formebolone">Formebolone</a></li> <li><a href="/wiki/Metandienone" title="Metandienone">Metandienone (methandienone, methandrostenolone)</a></li> <li><a href="/wiki/Methandriol" title="Methandriol">Methandriol (methylandrostenediol)</a></li> <li><a href="/wiki/Methandriol_bisenanthoyl_acetate" title="Methandriol bisenanthoyl acetate">Methandriol bisenanthoyl acetate</a></li> <li><a href="/wiki/Methandriol_dipropionate" title="Methandriol dipropionate">Methandriol dipropionate</a></li> <li><a href="/wiki/Methandriol_propionate" title="Methandriol propionate">Methandriol propionate</a></li> <li><a href="/wiki/Methyltestosterone" title="Methyltestosterone">Methyltestosterone</a></li> <li><a href="/wiki/Methyltestosterone_3-hexyl_ether" title="Methyltestosterone 3-hexyl ether">Methyltestosterone 3-hexyl ether</a></li> <li><a href="/wiki/Oxymesterone" title="Oxymesterone">Oxymesterone</a></li> <li><a href="/wiki/Penmesterol" title="Penmesterol">Penmesterol</a></li> <li><a href="/wiki/Tiomesterone" title="Tiomesterone">Tiomesterone (thiomesterone)</a></li></ul> <ul><li><i>17α-Alkylated dihydrotestosterone derivatives:</i> <a href="/wiki/Androisoxazole" title="Androisoxazole">Androisoxazole</a></li> <li><a href="/wiki/Furazabol" title="Furazabol">Furazabol</a></li> <li><a href="/wiki/Mebolazine" title="Mebolazine">Mebolazine (dimethazine)</a></li> <li><a href="/wiki/Mestanolone" title="Mestanolone">Mestanolone</a></li> <li><a href="/wiki/Oxandrolone" title="Oxandrolone">Oxandrolone</a></li> <li><a href="/wiki/Oxymetholone" title="Oxymetholone">Oxymetholone</a></li> <li><a href="/wiki/Stanozolol" title="Stanozolol">Stanozolol</a></li></ul> <ul><li><i>17α-Alkylated 19-nortestosterone derivatives:</i> <a href="/wiki/Ethylestrenol" title="Ethylestrenol">Ethylestrenol</a></li> <li><a href="/wiki/Mibolerone" title="Mibolerone">Mibolerone</a></li> <li><a href="/wiki/Norethandrolone" title="Norethandrolone">Norethandrolone</a></li> <li><a href="/wiki/Normethandrone" title="Normethandrone">Normethandrone (methylestrenolone, normethisterone)</a></li> <li><a href="/wiki/Propetandrol" title="Propetandrol">Propetandrol (propethandrol)</a></li></ul> <ul><li><i>17α-Vinyltestosterone derivatives:</i> <a href="/wiki/Norvinisterone" title="Norvinisterone">Norvinisterone (vinylnortestosterone)</a></li></ul> <ul><li><i>17α-Ethynyltestosterone derivatives:</i> <a class="mw-selflink selflink">Danazol</a></li> <li><a href="/wiki/Gestrinone" title="Gestrinone">Gestrinone</a></li> <li><a href="/wiki/Progestin" class="mw-redirect" title="Progestin">Progestins</a> (e.g., <a href="/wiki/Ethisterone" title="Ethisterone">ethisterone (ethynyltestosterone)</a>, <a href="/wiki/Levonorgestrel" title="Levonorgestrel">levonorgestrel</a>, <a href="/wiki/Norgestrel" title="Norgestrel">norgestrel</a>, <a href="/wiki/Norethisterone" title="Norethisterone">norethisterone (norethindrone)</a>, <a href="/wiki/Lynestrenol" title="Lynestrenol">lynestrenol</a>, <a href="/wiki/Norgestrienone" title="Norgestrienone">norgestrienone</a>)</li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li></ul> <ul><li><i>Progesterone derivatives:</i> <a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">Medroxyprogesterone acetate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:9em;;text-align:center;"><a href="/wiki/Progonadotropin" title="Progonadotropin">Progonadotropins</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Antiestrogen" title="Antiestrogen">Antiestrogens</a> (e.g., <a href="/wiki/Tamoxifen" title="Tamoxifen">tamoxifen</a>, <a href="/wiki/Clomifene" title="Clomifene">clomifene</a>)</li> <li><a href="/wiki/GnRH_agonist" class="mw-redirect" title="GnRH agonist">GnRH agonists</a> (e.g., <a href="/wiki/Gonadotropin-releasing_hormone" title="Gonadotropin-releasing hormone">GnRH (gonadorelin)</a>, <a href="/wiki/Leuprorelin" title="Leuprorelin">leuprorelin</a>)</li> <li><a href="/wiki/Gonadotropin" title="Gonadotropin">Gonadotropins</a> (e.g., <a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone"><abbr title="luteinizing hormone">LH</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip luteinizing hormone</span>, <a href="/wiki/Human_chorionic_gonadotropin" title="Human chorionic gonadotropin"><abbr title="human chorionic gonadotropin">hCG</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 human chorionic gonadotropin</span>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Antiandrogen" title="Antiandrogen">Antiandrogens</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:9em;;text-align:center;"><a href="/wiki/Androgen_receptor" title="Androgen receptor"><abbr title="Androgen receptor">AR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Androgen receptor</span> <a href="/wiki/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><i>Steroidal:</i> <a href="/wiki/Abiraterone_acetate" title="Abiraterone acetate">Abiraterone acetate</a> <a href="/wiki/Niraparib/abiraterone_acetate" title="Niraparib/abiraterone acetate">+niraparib</a></li> <li><a href="/wiki/Canrenone" title="Canrenone">Canrenone</a></li> <li><a href="/wiki/Chlormadinone_acetate" title="Chlormadinone acetate">Chlormadinone 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/Dienogest" title="Dienogest">Dienogest</a></li> <li><a href="/wiki/Drospirenone" title="Drospirenone">Drospirenone</a></li> <li><a href="/wiki/Medrogestone" title="Medrogestone">Medrogestone</a></li> <li><a href="/wiki/Megestrol_acetate" title="Megestrol acetate">Megestrol acetate</a></li> <li><a href="/wiki/Nomegestrol_acetate" title="Nomegestrol acetate">Nomegestrol acetate</a></li> <li><a href="/wiki/Osaterone_acetate" title="Osaterone acetate">Osaterone acetate</a></li> <li><a href="/wiki/Oxendolone" title="Oxendolone">Oxendolone</a></li> <li><a href="/wiki/Potassium_canrenoate" title="Potassium canrenoate">Potassium canrenoate</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li></ul> <ul><li><i>Nonsteroidal:</i> <a href="/wiki/Apalutamide" title="Apalutamide">Apalutamide</a></li> <li><a href="/wiki/Bicalutamide" title="Bicalutamide">Bicalutamide</a></li> <li><a href="/wiki/Cimetidine" title="Cimetidine">Cimetidine</a></li> <li><a href="/wiki/Darolutamide" title="Darolutamide">Darolutamide</a></li> <li><a href="/wiki/Enzalutamide" title="Enzalutamide">Enzalutamide</a></li> <li><a href="/wiki/Flutamide" title="Flutamide">Flutamide</a></li> <li><a href="/wiki/Ketoconazole" title="Ketoconazole">Ketoconazole</a></li> <li><a href="/wiki/Nilutamide" title="Nilutamide">Nilutamide</a></li> <li><a href="/wiki/Seviteronel" title="Seviteronel">Seviteronel</a><sup>†</sup></li> <li><a href="/wiki/Topilutamide" title="Topilutamide">Topilutamide (fluridil)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:9em;;text-align:center;"><a href="/wiki/Steroidogenesis_inhibitor" title="Steroidogenesis inhibitor">Steroidogenesis<br />inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="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/5%CE%B1-Reductase_inhibitor" title="5α-Reductase inhibitor">5α-Reductase</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/Alfatradiol" title="Alfatradiol">Alfatradiol</a></li> <li><a href="/wiki/Dutasteride" title="Dutasteride">Dutasteride</a></li> <li><a href="/wiki/Epristeride" title="Epristeride">Epristeride</a></li> <li><a href="/wiki/Finasteride" title="Finasteride">Finasteride</a></li> <li><a href="/wiki/Saw_palmetto_extract" title="Saw palmetto extract">Saw palmetto extract</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Others</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/Abiraterone_acetate" title="Abiraterone acetate">Abiraterone acetate</a> <a href="/wiki/Niraparib/abiraterone_acetate" title="Niraparib/abiraterone acetate">+niraparib</a></li> <li><a href="/wiki/Aminoglutethimide" title="Aminoglutethimide">Aminoglutethimide</a></li> <li><a href="/wiki/Bifluranol" title="Bifluranol">Bifluranol</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Flutamide" title="Flutamide">Flutamide</a></li> <li><a href="/wiki/Ketoconazole" title="Ketoconazole">Ketoconazole</a></li> <li><a href="/wiki/Nilutamide" title="Nilutamide">Nilutamide</a></li> <li><a href="/wiki/Seviteronel" title="Seviteronel">Seviteronel</a><sup>†</sup></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:9em;;text-align:center;"><a href="/wiki/Antigonadotropin" title="Antigonadotropin">Antigonadotropins</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/D2_receptor" class="mw-redirect" title="D2 receptor">D<sub>2</sub> receptor</a> <a href="/wiki/Dopamine_antagonist" title="Dopamine antagonist">antagonists</a> (<a href="/wiki/Prolactin_releaser" class="mw-redirect" title="Prolactin releaser">prolactin releasers</a>) (e.g., <a href="/wiki/Domperidone" title="Domperidone">domperidone</a>, <a href="/wiki/Metoclopramide" title="Metoclopramide">metoclopramide</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>, <a href="/wiki/Haloperidol" title="Haloperidol">haloperidol</a>, <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>, <a href="/wiki/Sulpiride" title="Sulpiride">sulpiride</a>)</li> <li><a href="/wiki/Estrogen" title="Estrogen">Estrogens</a> (e.g., <a href="/wiki/Bifluranol" title="Bifluranol">bifluranol</a>, <a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">diethylstilbestrol</a>, <a href="/wiki/Estradiol" title="Estradiol">estradiol</a>, <a href="/wiki/List_of_estrogen_esters#Estradiol_esters" title="List of estrogen esters">estradiol esters</a>, <a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">ethinylestradiol</a>, <a href="/wiki/Ethinylestradiol_sulfonate" title="Ethinylestradiol sulfonate">ethinylestradiol sulfonate</a>, <a href="/wiki/Paroxypropione" title="Paroxypropione">paroxypropione</a>)</li> <li><a href="/wiki/GnRH_agonist" class="mw-redirect" title="GnRH agonist">GnRH agonists</a> (e.g., <a href="/wiki/Leuprorelin" title="Leuprorelin">leuprorelin</a>)</li> <li><a href="/wiki/GnRH_antagonist" class="mw-redirect" title="GnRH antagonist">GnRH antagonists</a> (e.g., <a href="/wiki/Cetrorelix" title="Cetrorelix">cetrorelix</a>)</li> <li><a href="/wiki/Progestogen" title="Progestogen">Progestogens</a> (incl., <a href="/wiki/Chlormadinone_acetate" title="Chlormadinone acetate">chlormadinone acetate</a>, <a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">cyproterone acetate</a>, <a href="/wiki/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">hydroxyprogesterone caproate</a>, <a href="/wiki/Gestonorone_caproate" title="Gestonorone caproate">gestonorone caproate</a>, <a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">medroxyprogesterone acetate</a>, <a href="/wiki/Megestrol_acetate" title="Megestrol acetate">megestrol acetate</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:9em;;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Androstenedione immunogens:</i> <a href="/wiki/Androvax" title="Androvax">Androvax (androstenedione albumin)</a></li> <li><a href="/wiki/Ovandrotone_albumin" title="Ovandrotone albumin">Ovandrotone albumin (Fecundin)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td colspan="2" class="navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Androgen_receptor_modulators" title="Template:Androgen receptor modulators">Androgen receptor modulators</a></dd> <dd><a href="/wiki/Template:Estrogens_and_antiestrogens" title="Template:Estrogens and antiestrogens">Estrogens and antiestrogens</a></dd> <dd><a href="/wiki/Template:Progestogens_and_antiprogestogens" title="Template:Progestogens and antiprogestogens">Progestogens and antiprogestogens</a></dd> <dd><a href="/wiki/List_of_androgens/anabolic_steroids" class="mw-redirect" title="List of androgens/anabolic steroids">List of androgens/anabolic steroids</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="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><br />(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</span> <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><i>Progesterone derivatives:</i> <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">Progesterone</a></li> <li><a href="/wiki/Quingestrone" title="Quingestrone">Quingestrone</a></li></ul> <ul><li><i>Retroprogesterone derivatives:</i> <a href="/wiki/Dydrogesterone" title="Dydrogesterone">Dydrogesterone</a></li> <li><a href="/wiki/Trengestone" title="Trengestone">Trengestone</a></li></ul> <ul><li><i>17α-Hydroxyprogesterone (and closely related) derivatives:</i> <i>17α-Hydroxylated:</i> <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><sup>#</sup></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>; <i>17α-Methylated:</i> <a href="/wiki/Medrogestone" title="Medrogestone">Medrogestone</a>; <i>Others:</i> <a href="/wiki/Haloprogesterone" title="Haloprogesterone">Haloprogesterone</a></li></ul> <ul><li><i>19-Norprogesterone derivatives:</i> <i>17α-Hydroxylated:</i> <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>; <i>17α-Methylated:</i> <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><i>Testosterone derivatives:</i> <i>Estranes:</i> <a class="mw-selflink selflink">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><i>19-Nortestosterone derivatives:</i> <i>Estranes:</i> <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><sup>#</sup></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>; <i>Gonanes:</i> <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><sup>#</sup></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><i>Spirolactone derivatives:</i> <a href="/wiki/Drospirenone" title="Drospirenone">Drospirenone</a></li></ul> <ul><li><i>Others:</i> <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</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Telapristone" title="Telapristone">Telapristone</a><sup>§</sup></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</span> <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><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div> <dl><dt>See also</dt> <dd><a href="/wiki/Template: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:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Pharmacodynamics105" 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="Pharmacodynamics105" style="font-size:114%;margin:0 4em"><a href="/wiki/Pharmacodynamics" title="Pharmacodynamics">Pharmacodynamics</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="Androgen_receptor_modulators801" 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:Androgen_receptor_modulators" title="Template:Androgen receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Androgen_receptor_modulators" title="Template talk:Androgen receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Androgen_receptor_modulators" title="Special:EditPage/Template:Androgen receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Androgen_receptor_modulators801" style="font-size:114%;margin:0 4em"><a href="/wiki/Androgen_receptor" title="Androgen receptor">Androgen 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/Androgen_receptor" title="Androgen receptor"><abbr title="Androgen receptor">AR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Androgen receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Testosterone derivatives:</i> <a href="/wiki/4-Androstenediol" title="4-Androstenediol">4-Androstenediol</a></li> <li><a href="/wiki/4-Dehydroepiandrosterone" title="4-Dehydroepiandrosterone">4-Dehydroepiandrosterone (4-DHEA)</a></li> <li><a href="/wiki/4-Hydroxytestosterone" title="4-Hydroxytestosterone">4-Hydroxytestosterone</a></li> <li><a href="/w/index.php?title=4,17%CE%B1-Dimethyltestosterone&action=edit&redlink=1" class="new" title="4,17α-Dimethyltestosterone (page does not exist)">4,17α-Dimethyltestosterone</a></li> <li><a href="/wiki/5-Androstenedione" title="5-Androstenedione">5-Androstenedione</a></li> <li><a href="/wiki/11-Ketotestosterone" title="11-Ketotestosterone">11-Ketotestosterone</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, 11-oxoandrostenedione)</a></li> <li><a href="/wiki/5-Androstenediol" class="mw-redirect" title="5-Androstenediol">Androstenediol (5-androstenediol)</a> <ul><li><a href="/wiki/Androstenediol_3%CE%B2-acetate" title="Androstenediol 3β-acetate">Androstenediol 3β-acetate</a></li> <li><a href="/wiki/Androstenediol_17%CE%B2-acetate" title="Androstenediol 17β-acetate">Androstenediol 17β-acetate</a></li> <li><a href="/wiki/Androstenediol_diacetate" title="Androstenediol diacetate">Androstenediol diacetate</a></li> <li><a href="/wiki/Androstenediol_dipropionate" title="Androstenediol dipropionate">Androstenediol dipropionate</a></li></ul></li> <li><a href="/wiki/4-Androstenedione" class="mw-redirect" title="4-Androstenedione">Androstenedione (4-androstenedione)</a></li> <li><a href="/wiki/Atamestane" title="Atamestane">Atamestane</a></li> <li><a href="/wiki/Boldenone" title="Boldenone">Boldenone</a> <ul><li><a href="/wiki/Boldenone_undecylenate" title="Boldenone undecylenate">Boldenone undecylenate</a></li></ul></li> <li><a href="/wiki/Boldione" title="Boldione">Boldione (1,4-androstadienedione)</a></li> <li><a href="/wiki/Clostebol" title="Clostebol">Clostebol</a> <ul><li><a href="/wiki/Clostebol_acetate" title="Clostebol acetate">Clostebol acetate</a></li> <li><a href="/wiki/Clostebol_caproate" title="Clostebol caproate">Clostebol caproate</a></li> <li><a href="/wiki/Clostebol_propionate" title="Clostebol propionate">Clostebol propionate</a></li></ul></li> <li><a href="/wiki/Cloxotestosterone" title="Cloxotestosterone">Cloxotestosterone</a> <ul><li><a href="/wiki/Cloxotestosterone_acetate" title="Cloxotestosterone acetate">Cloxotestosterone acetate</a></li></ul></li> <li><a href="/wiki/Dehydroandrosterone" title="Dehydroandrosterone">Dehydroandrosterone</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA (androstenolone, prasterone; 5-DHEA)</a> <ul><li><a href="/wiki/Prasterone_enanthate" title="Prasterone enanthate">DHEA enanthate (prasterone enanthate)</a></li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA sulfate</a></li></ul></li> <li><a href="/wiki/Exemestane" title="Exemestane">Exemestane</a></li> <li><a href="/wiki/Formestane" title="Formestane">Formestane</a></li> <li><a href="/wiki/Plomestane" title="Plomestane">Plomestane</a></li> <li><a href="/wiki/Quinbolone" title="Quinbolone">Quinbolone</a></li> <li><a href="/wiki/Silandrone" title="Silandrone">Silandrone</a></li> <li><a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">Testosterone</a><sup>#</sup> (<a href="/wiki/Testosterone/dutasteride" title="Testosterone/dutasteride">+dutasteride</a>) <ul><li><a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">Testosterone esters</a></li> <li><a href="/wiki/Polytestosterone_phloretin_phosphate" title="Polytestosterone phloretin phosphate">Polytestosterone phloretin phosphate</a></li></ul></li></ul> <ul><li><i>5α-Dihydrotestosterone derivatives:</i> <a href="/wiki/1-Androstenediol" title="1-Androstenediol">1-Androstenediol</a></li> <li><a href="/wiki/1-Androstenedione" title="1-Androstenedione">1-Androstenedione</a></li> <li><a href="/wiki/1-Androsterone" title="1-Androsterone">1-Androsterone (1-andro, 1-DHEA)</a></li> <li><a href="/wiki/1-Testosterone" title="1-Testosterone">1-Testosterone</a></li> <li><a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/wiki/5%CE%B1-Androst-2-en-17-one" class="mw-redirect" title="5α-Androst-2-en-17-one">5α-Androst-2-en-17-one</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/11-Ketodihydrotestosterone" title="11-Ketodihydrotestosterone">11-Ketodihydrotestosterone</a></li> <li><a href="/wiki/Androsterone" title="Androsterone">Androsterone</a></li> <li><a href="/wiki/Bolazine" title="Bolazine">Bolazine</a> <ul><li><a href="/wiki/Bolazine_capronate" title="Bolazine capronate">Bolazine capronate</a></li></ul></li> <li><a href="/w/index.php?title=Dihydroethyltestosterone&action=edit&redlink=1" class="new" title="Dihydroethyltestosterone (page does not exist)">Dihydroethyltestosterone</a></li> <li><a href="/wiki/Dihydrofluoxymesterone" title="Dihydrofluoxymesterone">Dihydrofluoxymesterone</a></li> <li><a href="/w/index.php?title=Dihydromethylandrostenediol&action=edit&redlink=1" class="new" title="Dihydromethylandrostenediol (page does not exist)">Dihydromethylandrostenediol</a></li> <li><a href="/wiki/Dihydrotestosterone" title="Dihydrotestosterone">Dihydrotestosterone (DHT)</a> (<a href="/wiki/Androstanolone" title="Androstanolone">androstanolone, stanolone</a>) <ul><li><a href="/wiki/List_of_androgen_esters#Dihydrotestosterone_esters" title="List of androgen esters">Dihydrotestosterone esters</a></li></ul></li> <li><a href="/wiki/Drostanolone" title="Drostanolone">Drostanolone</a> <ul><li><a href="/wiki/Drostanolone_propionate" title="Drostanolone propionate">Drostanolone propionate</a></li></ul></li> <li><a href="/wiki/Epiandrosterone" title="Epiandrosterone">Epiandrosterone</a></li> <li><a href="/wiki/Epitiostanol" title="Epitiostanol">Epitiostanol</a></li> <li><a href="/wiki/Mepitiostane" title="Mepitiostane">Mepitiostane</a></li> <li><a href="/wiki/Mesabolone" title="Mesabolone">Mesabolone</a></li> <li><a href="/wiki/Mesterolone" title="Mesterolone">Mesterolone</a> <ul><li><a href="/wiki/Mesterolone_cipionate" title="Mesterolone cipionate">Mesterolone cipionate</a></li></ul></li> <li><a href="/wiki/Methyldiazinol" title="Methyldiazinol">Methyldiazinol</a></li> <li><a href="/wiki/Nisterime" title="Nisterime">Nisterime</a> <ul><li><a href="/wiki/Nisterime_acetate" title="Nisterime acetate">Nisterime acetate</a></li></ul></li> <li><a href="/wiki/Prostanozol" title="Prostanozol">Prostanozol</a></li> <li><a href="/wiki/Stenbolone" title="Stenbolone">Stenbolone</a> <ul><li><a href="/wiki/Stenbolone_acetate" title="Stenbolone acetate">Stenbolone acetate</a></li></ul></li> <li><a href="/wiki/Testifenon" title="Testifenon">Testifenon (testiphenon, testiphenone)</a></li></ul> <ul><li><i>19-Nortestosterone derivatives:</i> <a href="/wiki/7%CE%B1-Methyl-19-norandrostenedione" title="7α-Methyl-19-norandrostenedione">7α-Methyl-19-norandrostenedione (MENT dione, trestione)</a></li> <li><a href="/wiki/11%CE%B2-Methyl-19-nortestosterone" title="11β-Methyl-19-nortestosterone">11β-Methyl-19-nortestosterone</a> <ul><li><a href="/wiki/11%CE%B2-Methyl-19-nortestosterone_dodecylcarbonate" title="11β-Methyl-19-nortestosterone dodecylcarbonate">11β-Methyl-19-nortestosterone dodecylcarbonate</a></li></ul></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> <ul><li><a href="/wiki/Bolandiol_dipropionate" title="Bolandiol dipropionate">Bolandiol dipropionate</a></li></ul></li> <li><a href="/wiki/Bolandione" title="Bolandione">Bolandione (19-nor-4-androstenedione)</a></li> <li><a href="/wiki/Bolmantalate" title="Bolmantalate">Bolmantalate (nandrolone adamantoate)</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> <ul><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></ul></li> <li><a href="/wiki/LS-1727" title="LS-1727">LS-1727 (nandrolone 17β-<i>N</i>-(2-chloroethyl)-<i>N</i>-nitrosocarbamate)</a></li> <li><a href="/wiki/Methoxydienone" title="Methoxydienone">Methoxydienone (methoxygonadiene)</a></li> <li><a href="/wiki/Nandrolone" title="Nandrolone">Nandrolone</a> <ul><li><a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">Nandrolone esters</a></li></ul></li> <li><a href="/wiki/Norclostebol" title="Norclostebol">Norclostebol</a> <ul><li><a href="/wiki/Norclostebol_acetate" title="Norclostebol acetate">Norclostebol acetate</a></li></ul></li> <li><a href="/wiki/Normethandrone" title="Normethandrone">Normethandrone (methylestrenolone, normethisterone)</a></li> <li><a href="/wiki/Oxabolone" title="Oxabolone">Oxabolone</a> <ul><li><a href="/wiki/Oxabolone_cipionate" title="Oxabolone cipionate">Oxabolone cipionate (oxabolone cypionate)</a></li></ul></li> <li><a href="/wiki/Trenbolone" title="Trenbolone">Trenbolone</a> <ul><li><a href="/wiki/Trenbolone_acetate" title="Trenbolone acetate">Trenbolone acetate</a></li> <li><a href="/wiki/Trenbolone_enanthate" title="Trenbolone enanthate">Trenbolone enanthate</a></li> <li><a href="/wiki/Trenbolone_hexahydrobenzylcarbonate" title="Trenbolone hexahydrobenzylcarbonate">Trenbolone hexahydrobenzylcarbonate</a></li> <li><a href="/wiki/Trenbolone_undecanoate" title="Trenbolone undecanoate">Trenbolone undecanoate</a></li></ul></li> <li><a href="/wiki/Trendione" title="Trendione">Trendione</a></li> <li><a href="/wiki/Trestolone" title="Trestolone">Trestolone (MENT)</a> <ul><li><a href="/wiki/Trestolone_acetate" title="Trestolone acetate">Trestolone acetate</a></li> <li><a href="/wiki/Trestolone_enanthate" title="Trestolone enanthate">Trestolone enanthate</a></li></ul></li></ul> <ul><li><i>5α-Dihydro-19-nortestosterone derivatives:</i> <a href="/wiki/5%CE%B1-Dihydronandrolone" title="5α-Dihydronandrolone">5α-Dihydronandrolone</a></li> <li><a href="/w/index.php?title=5%CE%B1-Dihydrotrestolone&action=edit&redlink=1" class="new" title="5α-Dihydrotrestolone (page does not exist)">5α-Dihydrotrestolone</a></li> <li><a href="/wiki/19-Norandrosterone" title="19-Norandrosterone">19-Norandrosterone</a></li></ul> <ul><li><i>17α-Alkylated testosterone derivatives:</i> <a href="/wiki/Bolasterone" title="Bolasterone">Bolasterone</a></li> <li><a href="/wiki/Calusterone" title="Calusterone">Calusterone</a></li> <li><a href="/wiki/Chlorodehydromethylandrostenediol" title="Chlorodehydromethylandrostenediol">Chlorodehydromethylandrostenediol (CDMA)</a></li> <li><a href="/wiki/Chlorodehydromethyltestosterone" title="Chlorodehydromethyltestosterone">Chlorodehydromethyltestosterone (CDMT)</a></li> <li><a href="/wiki/Chloromethylandrostenediol" title="Chloromethylandrostenediol">Chloromethylandrostenediol (CMA)</a></li> <li><a href="/wiki/Enestebol" title="Enestebol">Enestebol</a></li> <li><a href="/wiki/Ethyltestosterone" title="Ethyltestosterone">Ethyltestosterone</a></li> <li><a href="/wiki/Fluoxymesterone" title="Fluoxymesterone">Fluoxymesterone</a></li> <li><a href="/wiki/Formebolone" title="Formebolone">Formebolone</a></li> <li><a href="/wiki/Hydroxystenozole" title="Hydroxystenozole">Hydroxystenozole</a></li> <li><a href="/wiki/Metandienone" title="Metandienone">Metandienone (methandrostenolone)</a></li> <li><a href="/wiki/Methandriol" title="Methandriol">Methandriol (methylandrostenediol)</a> <ul><li><a href="/wiki/Methandriol_bisenanthoyl_acetate" title="Methandriol bisenanthoyl acetate">Methandriol bisenanthoyl acetate</a></li> <li><a href="/wiki/Methandriol_diacetate" title="Methandriol diacetate">Methandriol diacetate</a></li> <li><a href="/wiki/Methandriol_dipropionate" title="Methandriol dipropionate">Methandriol dipropionate</a></li> <li><a href="/wiki/Methandriol_propionate" title="Methandriol propionate">Methandriol propionate</a></li></ul></li> <li><a href="/wiki/Methylclostebol" title="Methylclostebol">Methylclostebol (chloromethyltestosterone)</a></li> <li><a href="/wiki/Methyltestosterone" title="Methyltestosterone">Methyltestosterone</a> (<a href="/wiki/Esterified_estrogens/methyltestosterone" title="Esterified estrogens/methyltestosterone">+esterified estrogens</a>) <ul><li><a href="/wiki/Methyltestosterone_3-hexyl_ether" title="Methyltestosterone 3-hexyl ether">Methyltestosterone 3-hexyl ether</a></li></ul></li> <li><a href="/wiki/Oxymesterone" title="Oxymesterone">Oxymesterone</a></li> <li><a href="/wiki/Penmesterol" title="Penmesterol">Penmesterol</a></li> <li><a href="/wiki/Tiomesterone" title="Tiomesterone">Tiomesterone</a></li></ul> <ul><li><i>17α-Alkylated 5α-dihydrotestosterone derivatives:</i> <a href="/wiki/Androisoxazole" title="Androisoxazole">Androisoxazole</a></li> <li><a href="/wiki/Desoxymethyltestosterone" title="Desoxymethyltestosterone">Desoxymethyltestosterone</a></li> <li><a href="/wiki/Furazabol" title="Furazabol">Furazabol</a></li> <li><a href="/wiki/Mebolazine" title="Mebolazine">Mebolazine (dimethazine)</a></li> <li><a href="/wiki/Mestanolone" title="Mestanolone">Mestanolone</a></li> <li><a href="/wiki/Metenolone" title="Metenolone">Metenolone</a> <ul><li><a href="/wiki/Metenolone_acetate" title="Metenolone acetate">Metenolone acetate</a></li> <li><a href="/wiki/Metenolone_enanthate" title="Metenolone enanthate">Metenolone enanthate</a></li></ul></li> <li><a href="/wiki/Methasterone" title="Methasterone">Methasterone</a></li> <li><a href="/wiki/Methyl-1-testosterone" title="Methyl-1-testosterone">Methyl-1-testosterone</a></li> <li><a href="/wiki/Methylepitiostanol" title="Methylepitiostanol">Methylepitiostanol</a></li> <li><a href="/wiki/Methylstenbolone" title="Methylstenbolone">Methylstenbolone</a></li> <li><a href="/wiki/Oxandrolone" title="Oxandrolone">Oxandrolone</a></li> <li><a href="/wiki/Oxymetholone" title="Oxymetholone">Oxymetholone</a></li> <li><a href="/wiki/Stanozolol" title="Stanozolol">Stanozolol</a></li></ul> <ul><li><i>17α-Alkylated 19-nortestosterone derivatives:</i> <a href="/wiki/Bolenol" title="Bolenol">Bolenol</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</a></li> <li><a href="/wiki/Methyldienolone" title="Methyldienolone">Methyldienolone</a></li> <li><a href="/wiki/Methylhydroxynandrolone" title="Methylhydroxynandrolone">Methylhydroxynandrolone (MOHN, MHN)</a></li> <li><a href="/wiki/Metribolone" title="Metribolone">Metribolone</a></li> <li><a href="/wiki/Mibolerone" title="Mibolerone">Mibolerone</a></li> <li><a href="/wiki/Norboletone" title="Norboletone">Norboletone</a></li> <li><a href="/wiki/Norethandrolone" title="Norethandrolone">Norethandrolone</a></li> <li><a href="/wiki/Propetandrol" title="Propetandrol">Propetandrol</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></ul> <ul><li><i>17α-Alkylated 5α-dihydro-19-nortestosterone derivatives:</i> <a href="/wiki/5%CE%B1-Dihydronorethandrolone" title="5α-Dihydronorethandrolone">5α-Dihydronorethandrolone</a></li> <li><a href="/wiki/5%CE%B1-Dihydronormethandrone" title="5α-Dihydronormethandrone">5α-Dihydronormethandrone</a></li></ul> <ul><li><i>17α-Vinyltestosterone derivatives:</i> <a href="/wiki/Norvinisterone" title="Norvinisterone">Norvinisterone (vinylnortestosterone)</a></li></ul> <ul><li><i>17α-Vinyl-19-nortestosterone derivatives:</i> <a href="/wiki/Vinyltestosterone" title="Vinyltestosterone">Vinyltestosterone</a></li></ul> <ul><li><i>17α-Ethynyltestosterone derivatives:</i> <a class="mw-selflink selflink">Danazol</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 (ethynyltestosterone)</a></li></ul> <ul><li><i>5α-Dihydro-17α-ethynyltestosterone derivatives:</i> <a href="/wiki/17%CE%B1-Ethynyl-3%CE%B1-androstanediol" title="17α-Ethynyl-3α-androstanediol">17α-Ethynyl-3α-androstanediol</a></li> <li><a href="/wiki/17%CE%B1-Ethynyl-3%CE%B2-androstanediol" title="17α-Ethynyl-3β-androstanediol">17α-Ethynyl-3β-androstanediol</a></li> <li><a href="/wiki/Dihydroethisterone" class="mw-redirect" title="Dihydroethisterone">Dihydroethisterone</a></li></ul> <ul><li><i>17α-Ethynyl-19-nortestosterone derivatives:</i> <a href="/wiki/%CE%944-Tibolone" title="Δ4-Tibolone">Δ<sup>4</sup>-Tibolone</a></li> <li><a href="/wiki/Desogestrel" title="Desogestrel">Desogestrel</a></li> <li><a href="/wiki/Etonogestrel" title="Etonogestrel">Etonogestrel</a></li> <li><a href="/wiki/Etynodiol" title="Etynodiol">Etynodiol</a> <ul><li><a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">Etynodiol diacetate</a></li></ul></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> <ul><li><a href="/wiki/Lynestrenol_phenylpropionate" title="Lynestrenol phenylpropionate">Lynestrenol phenylpropionate</a></li></ul></li> <li><a href="/wiki/Norethisterone" title="Norethisterone">Norethisterone</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/Norgestrel" title="Norgestrel">Norgestrel</a></li> <li><a href="/wiki/Norgestrienone" title="Norgestrienone">Norgestrienone</a></li> <li><a href="/wiki/Quingestanol" title="Quingestanol">Quingestanol</a> <ul><li><a href="/wiki/Quingestanol_acetate" title="Quingestanol acetate">Quingestanol acetate</a></li></ul></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li></ul> <ul><li><i>5α-Dihydro-17α-ethynyl-19-nortestosterone derivatives:</i> <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></ul> <ul><li><i>Progesterone derivatives:</i> <a href="/wiki/6%CE%B1-Methylprogesterone" title="6α-Methylprogesterone">6α-Methylprogesterone</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></ul> <ul><li><i>Others/unsorted:</i> <a href="/wiki/3-Keto-5%CE%B1-abiraterone" title="3-Keto-5α-abiraterone">3-Keto-5α-abiraterone</a></li> <li><a href="/wiki/5%CE%B1-Androstane" class="mw-redirect" title="5α-Androstane">5α-Androstane</a></li> <li><a href="/wiki/Alternariol" title="Alternariol">Alternariol</a></li> <li><a href="/wiki/Cl-4AS-1" title="Cl-4AS-1">Cl-4AS-1</a></li> <li><a href="/wiki/Drupanol" title="Drupanol">Drupanol</a></li> <li><a href="/wiki/Trilostane" title="Trilostane">Trilostane</a></li> <li><a href="/wiki/ZM-182345" title="ZM-182345">ZM-182345</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center"><a href="/wiki/Selective_androgen_receptor_modulator" title="Selective androgen receptor modulator"><abbr title="Selective androgen receptor modulator">SARMs</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 androgen receptor modulator</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Nonsteroidal:</i> <a href="/w/index.php?title=198RL26&action=edit&redlink=1" class="new" title="198RL26 (page does not exist)">198RL26</a></li> <li><a href="/wiki/ACP-105" title="ACP-105">ACP-105</a></li> <li><a href="/wiki/AC-262,536" title="AC-262,536">AC-262,536</a></li> <li><a href="/wiki/Acetothiolutamide" title="Acetothiolutamide">Acetothiolutamide</a></li> <li><a href="/wiki/Acetoxolutamide" title="Acetoxolutamide">Acetoxolutamide</a></li> <li><a href="/wiki/Andarine" title="Andarine">Andarine (acetamidoxolutamide, androxolutamide, GTx-007, S-4)</a></li> <li><a href="/wiki/BMS-564,929" title="BMS-564,929">BMS-564,929</a></li> <li><a href="/w/index.php?title=DTIB&action=edit&redlink=1" class="new" title="DTIB (page does not exist)">DTIB</a></li> <li><a href="/wiki/Enobosarm" title="Enobosarm">Enobosarm (ostarine, MK-2866, GTx-024, S-22)</a></li> <li><a href="/w/index.php?title=FTBU-1&action=edit&redlink=1" class="new" title="FTBU-1 (page does not exist)">FTBU-1</a></li> <li><a href="/wiki/GLPG-0492" title="GLPG-0492">GLPG-0492</a></li> <li><a href="/wiki/GSK2881078" title="GSK2881078">GSK2881078</a></li> <li><a href="/wiki/GSK-4336A" title="GSK-4336A">GSK-4336A</a></li> <li><a href="/w/index.php?title=GSK-8698&action=edit&redlink=1" class="new" title="GSK-8698 (page does not exist)">GSK-8698</a></li> <li><a href="/wiki/LG121071" title="LG121071">LG121071 (LGD-121071)</a></li> <li><a href="/wiki/LGD-2226" title="LGD-2226">LGD-2226</a></li> <li><a href="/wiki/LGD-2941" title="LGD-2941">LGD-2941 (LGD-122941)</a></li> <li><a href="/wiki/LGD-3303" title="LGD-3303">LGD-3303</a></li> <li><a href="/wiki/LGD-4033" class="mw-redirect" title="LGD-4033">LGD-4033</a></li> <li><a href="/wiki/LY305" title="LY305">LY305</a></li> <li><a href="/wiki/JNJ-26146900" title="JNJ-26146900">JNJ-26146900</a></li> <li><a href="/wiki/JNJ-28330835" title="JNJ-28330835">JNJ-28330835</a></li> <li><a href="/wiki/JNJ-37654032" title="JNJ-37654032">JNJ-37654032</a></li> <li><a href="/wiki/OPK-88004" title="OPK-88004">OPK-88004 (LY-2452473, TT-701)</a></li> <li><a href="/w/index.php?title=ORM-11984&action=edit&redlink=1" class="new" title="ORM-11984 (page does not exist)">ORM-11984</a></li> <li><a href="/wiki/PF-06260414" title="PF-06260414">PF-06260414</a></li> <li><a href="/w/index.php?title=R-1_(drug)&action=edit&redlink=1" class="new" title="R-1 (drug) (page does not exist)">R-1</a></li> <li><a href="/wiki/RU-59063" title="RU-59063">RU-59063</a></li> <li><a href="/w/index.php?title=S-1_(drug)&action=edit&redlink=1" class="new" title="S-1 (drug) (page does not exist)">S-1</a></li> <li><a href="/wiki/S-23_(drug)" title="S-23 (drug)">S-23</a></li> <li><a href="/wiki/S-40503" title="S-40503">S-40503</a></li> <li><a href="/w/index.php?title=S-101479&action=edit&redlink=1" class="new" title="S-101479 (page does not exist)">S-101479</a></li> <li><a href="/wiki/Vosilasarm" title="Vosilasarm">Vosilasarm</a></li></ul> <ul><li><i>Steroidal:</i> <a href="/w/index.php?title=EM-9017&action=edit&redlink=1" class="new" title="EM-9017 (page does not exist)">EM-9017</a></li> <li><a href="/wiki/MK-0773" title="MK-0773">MK-0773</a></li> <li><a href="/wiki/TFM-4AS-1" title="TFM-4AS-1">TFM-4AS-1</a></li> <li><a href="/wiki/YK-11" title="YK-11">YK-11</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><i>Steroidal:</i> <a href="/wiki/7%CE%B1-Thioprogesterone" title="7α-Thioprogesterone">7α-Thioprogesterone</a></li> <li><a href="/wiki/7%CE%B1-Thiospironolactone" title="7α-Thiospironolactone">7α-Thiospironolactone</a></li> <li><a href="/wiki/7%CE%B1-Thiomethylspironolactone" title="7α-Thiomethylspironolactone">7α-Thiomethylspironolactone</a></li> <li><a href="/wiki/11%CE%B1-Hydroxyprogesterone" title="11α-Hydroxyprogesterone">11α-Hydroxyprogesterone</a></li> <li><a href="/wiki/15%CE%B2-Hydroxycyproterone_acetate" title="15β-Hydroxycyproterone acetate">15β-Hydroxycyproterone acetate</a></li> <li><a href="/wiki/Abiraterone" class="mw-redirect" title="Abiraterone">Abiraterone</a></li> <li><a href="/wiki/Abiraterone_acetate" title="Abiraterone acetate">Abiraterone acetate</a></li> <li><a href="/wiki/Allyltestosterone" title="Allyltestosterone">Allyltestosterone</a></li> <li><a href="/wiki/Benorterone" title="Benorterone">Benorterone</a></li> <li><a href="/wiki/BOMT" title="BOMT">BOMT</a></li> <li><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/Chlormadinone_acetate" title="Chlormadinone acetate">Chlormadinone acetate</a></li> <li><a href="/wiki/Clascoterone" title="Clascoterone">Clascoterone</a></li> <li><a href="/wiki/Clometerone" title="Clometerone">Clometerone</a></li> <li><a href="/wiki/Cyproheptadine" title="Cyproheptadine">Cyproheptadine</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/Delanterone" title="Delanterone">Delanterone</a></li> <li><a href="/wiki/Delmadinone_acetate" title="Delmadinone acetate">Delmadinone acetate</a></li> <li><a href="/wiki/Dicirenone" title="Dicirenone">Dicirenone</a></li> <li><a href="/wiki/Dienogest" title="Dienogest">Dienogest</a></li> <li><a href="/wiki/Drospirenone" title="Drospirenone">Drospirenone</a></li> <li><a href="/wiki/DU-41165" title="DU-41165">DU-41165</a></li> <li><a href="/wiki/Edogestrone" title="Edogestrone">Edogestrone</a></li> <li><a href="/w/index.php?title=EM-4350&action=edit&redlink=1" class="new" title="EM-4350 (page does not exist)">EM-4350</a></li> <li><a href="/wiki/EM-5854" title="EM-5854">EM-5854</a></li> <li><a href="/w/index.php?title=EM-5855&action=edit&redlink=1" class="new" title="EM-5855 (page does not exist)">EM-5855</a></li> <li><a href="/w/index.php?title=EM-6537&action=edit&redlink=1" class="new" title="EM-6537 (page does not exist)">EM-6537</a></li> <li><a href="/wiki/Epitestosterone" title="Epitestosterone">Epitestosterone</a></li> <li><a href="/wiki/Galeterone" title="Galeterone">Galeterone</a></li> <li><a href="/wiki/Guggulsterone" title="Guggulsterone">Guggulsterone</a></li> <li><a href="/w/index.php?title=Ludaterone&action=edit&redlink=1" class="new" title="Ludaterone (page does not exist)">Ludaterone</a></li> <li><a href="/wiki/Medrogestone" title="Medrogestone">Medrogestone</a></li> <li><a href="/wiki/Megestrol_acetate" title="Megestrol acetate">Megestrol acetate</a></li> <li><a href="/wiki/Mespirenone" title="Mespirenone">Mespirenone</a></li> <li><a href="/wiki/Metogest" title="Metogest">Metogest</a></li> <li><a href="/wiki/Mexrenone" title="Mexrenone">Mexrenone</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li> <li><a href="/wiki/Nomegestrol_acetate" title="Nomegestrol acetate">Nomegestrol acetate</a></li> <li><a href="/wiki/Nordinone" title="Nordinone">Nordinone</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/Oxendolone" title="Oxendolone">Oxendolone</a></li> <li><a href="/wiki/Potassium_canrenoate" title="Potassium canrenoate">Potassium canrenoate</a></li> <li><a href="/wiki/Promegestone" title="Promegestone">Promegestone</a></li> <li><a href="/wiki/Prorenone" title="Prorenone">Prorenone</a></li> <li><a href="/wiki/Rosterolone" title="Rosterolone">Rosterolone</a></li> <li><a href="/w/index.php?title=RU-15328&action=edit&redlink=1" class="new" title="RU-15328 (page does not exist)">RU-15328</a></li> <li><a href="/wiki/SC-5233" title="SC-5233">SC-5233 (spirolactone)</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/wiki/Spirorenone" title="Spirorenone">Spirorenone</a></li> <li><a href="/wiki/Spiroxasone" title="Spiroxasone">Spiroxasone</a></li> <li><a href="/wiki/Topterone" title="Topterone">Topterone</a></li> <li><a href="/wiki/Trimegestone" title="Trimegestone">Trimegestone</a></li> <li><a href="/wiki/Trimethyltrienolone" title="Trimethyltrienolone">Trimethyltrienolone (R-2956)</a></li> <li><a href="/wiki/Zanoterone" title="Zanoterone">Zanoterone</a></li></ul> <ul><li><i>Nonsteroidal:</i> <a href="/wiki/5N-Bicalutamide" title="5N-Bicalutamide">5<i>N</i>-Bicalutamide</a></li> <li><a href="/wiki/AA560" title="AA560">AA560</a></li> <li><a href="/w/index.php?title=Antarlide&action=edit&redlink=1" class="new" title="Antarlide (page does not exist)">Antarlides</a></li> <li><a href="/w/index.php?title=Arabilin&action=edit&redlink=1" class="new" title="Arabilin (page does not exist)">Arabilin</a></li> <li><a href="/wiki/Apalutamide" title="Apalutamide">Apalutamide</a></li> <li><a href="/wiki/Atraric_acid" title="Atraric acid">Atraric acid</a></li> <li><a href="/w/index.php?title=AZD-3514&action=edit&redlink=1" class="new" title="AZD-3514 (page does not exist)">AZD-3514</a></li> <li><a href="/wiki/Bakuchiol" title="Bakuchiol">Bakuchiol</a></li> <li><a href="/wiki/Bavdegalutamide" title="Bavdegalutamide">Bavdegalutamide</a></li> <li><a href="/w/index.php?title=BAY-1024767&action=edit&redlink=1" class="new" title="BAY-1024767 (page does not exist)">BAY-1024767</a></li> <li><a href="/wiki/Bicalutamide" title="Bicalutamide">Bicalutamide</a></li> <li><a href="/wiki/Bisphenol" title="Bisphenol">Bisphenols</a> (e.g., <a href="/wiki/Bisphenol_A_diglycidyl_ether" title="Bisphenol A diglycidyl ether">BADGE</a>, <a href="/w/index.php?title=Bisphenol_F_diglycidyl_ether&action=edit&redlink=1" class="new" title="Bisphenol F diglycidyl ether (page does not exist)">BFDGE</a>, <a href="/wiki/Bisphenol_A" title="Bisphenol A">bisphenol A</a>, <a href="/wiki/Bisphenol_F" title="Bisphenol F">bisphenol F</a>, <a href="/wiki/Bisphenol_S" title="Bisphenol S">bisphenol S</a>)</li> <li><a href="/w/index.php?title=BMS-501949&action=edit&redlink=1" class="new" title="BMS-501949 (page does not exist)">BMS-501949</a></li> <li><a href="/w/index.php?title=BMS-570511&action=edit&redlink=1" class="new" title="BMS-570511 (page does not exist)">BMS-570511</a></li> <li><a href="/wiki/BMS-641988" title="BMS-641988">BMS-641988</a></li> <li><a href="/w/index.php?title=CH5137291&action=edit&redlink=1" class="new" title="CH5137291 (page does not exist)">CH5137291</a></li> <li><a href="/wiki/Cimetidine" title="Cimetidine">Cimetidine</a></li> <li><a href="/wiki/Cioteronel" title="Cioteronel">Cioteronel</a></li> <li><a href="/wiki/Cyanonilutamide" title="Cyanonilutamide">Cyanonilutamide</a></li> <li><a href="/wiki/Darolutamide" title="Darolutamide">Darolutamide</a></li> <li><a href="/wiki/DDT" title="DDT">DDT</a> (via metabolite <a href="/wiki/Dichlorodiphenyldichloroethylene" title="Dichlorodiphenyldichloroethylene">p,p’-DDE</a>)</li> <li><a href="/wiki/Dieldrin" title="Dieldrin">Dieldrin</a></li> <li><a href="/wiki/DIMP_(antiandrogen)" title="DIMP (antiandrogen)">DIMP</a></li> <li><a href="/wiki/Endosulfan" title="Endosulfan">Endosulfan</a></li> <li><a href="/wiki/Enzalutamide" title="Enzalutamide">Enzalutamide</a></li> <li><a href="/wiki/EPI-001" title="EPI-001">EPI-001</a></li> <li><a href="/wiki/Fenarimol" title="Fenarimol">Fenarimol</a></li> <li><a href="/wiki/Flutamide" title="Flutamide">Flutamide</a></li> <li><a href="/wiki/Hydroxyflutamide" title="Hydroxyflutamide">Hydroxyflutamide</a></li> <li><a href="/wiki/Inocoterone" title="Inocoterone">Inocoterone</a></li> <li><a href="/wiki/Inocoterone_acetate" title="Inocoterone acetate">Inocoterone acetate</a></li> <li><a href="/wiki/Ketoconazole" title="Ketoconazole">Ketoconazole</a></li> <li><a href="/wiki/Ketodarolutamide" title="Ketodarolutamide">Ketodarolutamide</a></li> <li><a href="/wiki/Lavender_oil" title="Lavender oil">Lavender oil</a></li> <li><a href="/w/index.php?title=LG-105&action=edit&redlink=1" class="new" title="LG-105 (page does not exist)">LG-105</a></li> <li><a href="/wiki/LG-120907" title="LG-120907">LG-120907</a></li> <li><a href="/w/index.php?title=LGD-1331&action=edit&redlink=1" class="new" title="LGD-1331 (page does not exist)">LGD-1331</a></li> <li><a href="/wiki/Linuron" title="Linuron">Linuron</a></li> <li><a href="/wiki/Masofaniten" title="Masofaniten">Masofaniten</a></li> <li><a href="/wiki/Methiocarb" title="Methiocarb">Methiocarb</a></li> <li><a href="/w/index.php?title=N-Butylbenzenesulfonamide&action=edit&redlink=1" class="new" title="N-Butylbenzenesulfonamide (page does not exist)"><i>N</i>-Butylbenzenesulfonamide</a></li> <li><a href="/wiki/N-Desmethylapalutamide" title="N-Desmethylapalutamide"><i>N</i>-Desmethylapalutamide</a></li> <li><a href="/wiki/N-Desmethylenzalutamide" title="N-Desmethylenzalutamide"><i>N</i>-Desmethylenzalutamide</a></li> <li><a href="/wiki/Nilutamide" title="Nilutamide">Nilutamide</a></li> <li><a href="/w/index.php?title=ONC1-13B&action=edit&redlink=1" class="new" title="ONC1-13B (page does not exist)">ONC1-13B</a></li> <li><a href="/wiki/Pentomone" title="Pentomone">Pentomone</a></li> <li><a href="/w/index.php?title=PF-998425&action=edit&redlink=1" class="new" title="PF-998425 (page does not exist)">PF-998425</a></li> <li><a href="/wiki/Phenothrin" title="Phenothrin">Phenothrin</a></li> <li><a href="/wiki/Prochloraz" title="Prochloraz">Prochloraz</a></li> <li><a href="/wiki/Procymidone" title="Procymidone">Procymidone</a></li> <li><a href="/wiki/Proxalutamide" title="Proxalutamide">Proxalutamide</a></li> <li><a href="/wiki/Pyrilutamide" title="Pyrilutamide">Pyrilutamide</a></li> <li><a href="/wiki/Ralaniten" title="Ralaniten">Ralaniten (EPI-002)</a></li> <li><a href="/wiki/Ralaniten_acetate" title="Ralaniten acetate">Ralaniten acetate (EPI-506)</a></li> <li><a href="/wiki/RD-162" title="RD-162">RD-162</a></li> <li><a href="/wiki/Rezvilutamide" title="Rezvilutamide">Rezvilutamide</a></li> <li><a href="/w/index.php?title=Ro_2-7239&action=edit&redlink=1" class="new" title="Ro 2-7239 (page does not exist)">Ro 2-7239</a></li> <li><a href="/w/index.php?title=Ro_5-2537&action=edit&redlink=1" class="new" title="Ro 5-2537 (page does not exist)">Ro 5-2537</a></li> <li><a href="/wiki/RU-22930" title="RU-22930">RU-22930</a></li> <li><a href="/wiki/RU-56187" title="RU-56187">RU-56187</a></li> <li><a href="/wiki/RU-57073" title="RU-57073">RU-57073</a></li> <li><a href="/wiki/RU-58642" title="RU-58642">RU-58642</a></li> <li><a href="/wiki/RU-58841" title="RU-58841">RU-58841</a></li> <li><a href="/wiki/Seviteronel" title="Seviteronel">Seviteronel</a></li> <li><a href="/wiki/Thalidomide" title="Thalidomide">Thalidomide</a></li> <li><a href="/wiki/Topilutamide" title="Topilutamide">Topilutamide (fluridil)</a></li> <li><a href="/wiki/Valproic_acid" class="mw-redirect" title="Valproic acid">Valproic acid</a></li> <li><a href="/wiki/Vinclozolin" title="Vinclozolin">Vinclozolin</a></li> <li><a href="/w/index.php?title=YM-580&action=edit&redlink=1" class="new" title="YM-580 (page does not exist)">YM-580</a></li> <li><a href="/w/index.php?title=YM-92088&action=edit&redlink=1" class="new" title="YM-92088 (page does not exist)">YM-92088</a></li> <li><a href="/w/index.php?title=YM-175735&action=edit&redlink=1" class="new" title="YM-175735 (page does not exist)">YM-175735</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/GPRC6A" title="GPRC6A">GPRC6A</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: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/Cation" class="mw-redirect" title="Cation">Cations</a> (incl. <a href="/wiki/Aluminium" title="Aluminium">aluminium</a>, <a href="/wiki/Calcium" title="Calcium">calcium</a>, <a href="/wiki/Gadolinium" title="Gadolinium">gadolinium</a>, <a href="/wiki/Magnesium" title="Magnesium">magnesium</a>, <a href="/wiki/Strontium" title="Strontium">strontium</a>, <a href="/wiki/Zinc" title="Zinc">zinc</a>)</li> <li><a href="/wiki/Dehydroandrosterone" title="Dehydroandrosterone">Dehydroandrosterone</a></li> <li><a href="/wiki/Dihydrotestosterone" title="Dihydrotestosterone">Dihydrotestosterone</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/wiki/Amino_acid" title="Amino acid"><small>L</small>-α-Amino acids</a> (incl. <a href="/wiki/Arginine" title="Arginine"><small>L</small>-arginine</a>, <a href="/wiki/Lysine" title="Lysine"><small>L</small>-lysine</a>, <a href="/wiki/Ornithine" title="Ornithine"><small>L</small>-ornithine</a>)</li> <li><a href="/wiki/Osteocalcin" title="Osteocalcin">Osteocalcin</a></li> <li><a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin"><abbr title="Sex hormone-binding globulin">SHBG</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Sex hormone-binding globulin</span></li> <li><a href="/wiki/Testosterone" title="Testosterone">Testosterone</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:Androgens_and_antiandrogens" title="Template:Androgens and antiandrogens">Androgens and antiandrogens</a></dd> <dd><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators">Estrogen receptor modulators</a></dd> <dd><a href="/wiki/Template:Progesterone_receptor_modulators" title="Template:Progesterone receptor modulators">Progesterone receptor modulators</a></dd> <dd><a href="/wiki/List_of_androgens_and_anabolic_steroids" title="List of androgens and anabolic steroids">List of androgens and anabolic steroids</a></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Estrogen_receptor_modulators1222" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Estrogen_receptor_modulators" title="Template talk:Estrogen receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Estrogen_receptor_modulators" title="Special:EditPage/Template:Estrogen receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Estrogen_receptor_modulators1222" style="font-size:114%;margin:0 4em"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor">Estrogen receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Steroidal:</i> <a href="/wiki/2-Hydroxyestradiol" title="2-Hydroxyestradiol">2-Hydroxyestradiol</a></li> <li><a href="/wiki/2-Hydroxyestrone" title="2-Hydroxyestrone">2-Hydroxyestrone</a></li> <li><a href="/wiki/3-Methyl-19-methyleneandrosta-3,5-dien-17%CE%B2-ol" title="3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol">3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol</a></li> <li><a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/w/index.php?title=3%CE%B1,5%CE%B1-Dihydrolevonorgestrel&action=edit&redlink=1" class="new" title="3α,5α-Dihydrolevonorgestrel (page does not exist)">3α,5α-Dihydrolevonorgestrel</a></li> <li><a href="/w/index.php?title=3%CE%B2,5%CE%B1-Dihydrolevonorgestrel&action=edit&redlink=1" class="new" title="3β,5α-Dihydrolevonorgestrel (page does not exist)">3β,5α-Dihydrolevonorgestrel</a></li> <li><a href="/wiki/3%CE%B1-Hydroxytibolone" title="3α-Hydroxytibolone">3α-Hydroxytibolone</a></li> <li><a href="/wiki/3%CE%B2-Hydroxytibolone" title="3β-Hydroxytibolone">3β-Hydroxytibolone</a></li> <li><a href="/wiki/3%CE%B2-Androstanediol" title="3β-Androstanediol">3β-Androstanediol</a></li> <li><a href="/wiki/4-Androstenediol" title="4-Androstenediol">4-Androstenediol</a></li> <li><a href="/wiki/4-Androstenedione" class="mw-redirect" title="4-Androstenedione">4-Androstenedione</a></li> <li><a href="/wiki/4-Fluoroestradiol" title="4-Fluoroestradiol">4-Fluoroestradiol</a></li> <li><a href="/wiki/4-Hydroxyestradiol" title="4-Hydroxyestradiol">4-Hydroxyestradiol</a></li> <li><a href="/wiki/4-Hydroxyestrone" title="4-Hydroxyestrone">4-Hydroxyestrone</a></li> <li><a href="/wiki/4-Methoxyestradiol" title="4-Methoxyestradiol">4-Methoxyestradiol</a></li> <li><a href="/wiki/4-Methoxyestrone" title="4-Methoxyestrone">4-Methoxyestrone</a></li> <li><a href="/wiki/5-Androstenediol" class="mw-redirect" title="5-Androstenediol">5-Androstenediol</a></li> <li><a href="/wiki/7-Keto-DHEA" title="7-Keto-DHEA">7-Oxo-DHEA</a></li> <li><a href="/wiki/7%CE%B1-Hydroxy-DHEA" title="7α-Hydroxy-DHEA">7α-Hydroxy-DHEA</a></li> <li><a href="/wiki/7%CE%B1-Methylestradiol" title="7α-Methylestradiol">7α-Methylestradiol</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/8,9-Dehydroestradiol" title="8,9-Dehydroestradiol">8,9-Dehydroestradiol</a></li> <li><a href="/wiki/8,9-Dehydroestrone" title="8,9-Dehydroestrone">8,9-Dehydroestrone</a></li> <li><a href="/wiki/8%CE%B2-VE2" title="8β-VE2">8β-VE2</a></li> <li><a href="/wiki/10%CE%B2,17%CE%B2-Dihydroxyestra-1,4-dien-3-one" title="10β,17β-Dihydroxyestra-1,4-dien-3-one">10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)</a></li> <li><a href="/wiki/11%CE%B2-Chloromethylestradiol" title="11β-Chloromethylestradiol">11β-Chloromethylestradiol</a></li> <li><a href="/wiki/11%CE%B2-Methoxyestradiol" title="11β-Methoxyestradiol">11β-Methoxyestradiol</a></li> <li><a href="/wiki/15%CE%B1-Hydroxyestradiol" title="15α-Hydroxyestradiol">15α-Hydroxyestradiol</a></li> <li><a href="/wiki/16-Ketoestradiol" title="16-Ketoestradiol">16-Ketoestradiol</a></li> <li><a href="/wiki/16-Ketoestrone" title="16-Ketoestrone">16-Ketoestrone</a></li> <li><a href="/wiki/16%CE%B1-Fluoroestradiol" class="mw-redirect" title="16α-Fluoroestradiol">16α-Fluoroestradiol</a></li> <li><a href="/wiki/16%CE%B1-Hydroxy-DHEA" title="16α-Hydroxy-DHEA">16α-Hydroxy-DHEA</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyestrone" title="16α-Hydroxyestrone">16α-Hydroxyestrone</a></li> <li><a href="/wiki/16%CE%B1-Iodoestradiol" class="mw-redirect" title="16α-Iodoestradiol">16α-Iodoestradiol</a></li> <li><a href="/wiki/16%CE%B1-LE2" title="16α-LE2">16α-LE2</a></li> <li><a href="/wiki/16%CE%B2-Hydroxyestrone" title="16β-Hydroxyestrone">16β-Hydroxyestrone</a></li> <li><a href="/wiki/16%CE%B2,17%CE%B1-Epiestriol" title="16β,17α-Epiestriol">16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)</a></li> <li><a href="/wiki/17%CE%B1-Estradiol" title="17α-Estradiol">17α-Estradiol</a> (<a href="/wiki/Alfatradiol" title="Alfatradiol">alfatradiol</a>)</li> <li><a href="/wiki/17%CE%B1-Dihydroequilenin" title="17α-Dihydroequilenin">17α-Dihydroequilenin</a></li> <li><a href="/wiki/17%CE%B1-Dihydroequilin" title="17α-Dihydroequilin">17α-Dihydroequilin</a></li> <li><a href="/wiki/17%CE%B1-Epiestriol" title="17α-Epiestriol">17α-Epiestriol (16α-hydroxy-17α-estradiol)</a></li> <li><a href="/wiki/17%CE%B1-Ethynyl-3%CE%B1-androstanediol" title="17α-Ethynyl-3α-androstanediol">17α-Ethynyl-3α-androstanediol</a></li> <li><a href="/wiki/17%CE%B1-Ethynyl-3%CE%B2-androstanediol" title="17α-Ethynyl-3β-androstanediol">17α-Ethynyl-3β-androstanediol</a></li> <li><a href="/wiki/17%CE%B2-Dihydroequilenin" title="17β-Dihydroequilenin">17β-Dihydroequilenin</a></li> <li><a href="/wiki/17%CE%B2-Dihydroequilin" title="17β-Dihydroequilin">17β-Dihydroequilin</a></li> <li><a href="/wiki/17%CE%B2-Methyl-17%CE%B1-dihydroequilenin" title="17β-Methyl-17α-dihydroequilenin">17β-Methyl-17α-dihydroequilenin</a></li> <li><a href="/wiki/Abiraterone" class="mw-redirect" title="Abiraterone">Abiraterone</a></li> <li><a href="/wiki/Abiraterone_acetate" title="Abiraterone acetate">Abiraterone acetate</a></li> <li><a href="/wiki/Alestramustine" title="Alestramustine">Alestramustine</a></li> <li><a href="/wiki/Almestrone" title="Almestrone">Almestrone</a></li> <li><a href="/wiki/Anabolic_steroid" title="Anabolic steroid">Anabolic steroids</a> (e.g., <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> and <a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">esters</a>, <a href="/wiki/Methyltestosterone" title="Methyltestosterone">methyltestosterone</a>, <a href="/wiki/Metandienone" title="Metandienone">metandienone (methandrostenolone)</a>, <a href="/wiki/Nandrolone" title="Nandrolone">nandrolone</a> and <a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">esters</a>, many others; via estrogenic metabolites)</li> <li><a href="/wiki/Atrimustine" title="Atrimustine">Atrimustine</a></li> <li><a href="/wiki/Bolandiol" title="Bolandiol">Bolandiol</a></li> <li><a href="/wiki/Bolandiol_dipropionate" title="Bolandiol dipropionate">Bolandiol dipropionate</a></li> <li><a href="/wiki/Butolame" title="Butolame">Butolame</a></li> <li><a href="/wiki/Clomestrone" title="Clomestrone">Clomestrone</a></li> <li><a href="/wiki/Cloxestradiol" title="Cloxestradiol">Cloxestradiol</a> <ul><li><a href="/wiki/Cloxestradiol_acetate" title="Cloxestradiol acetate">Cloxestradiol acetate</a></li></ul></li> <li><a href="/wiki/Conjugated_estriol" title="Conjugated estriol">Conjugated estriol</a></li> <li><a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a></li> <li><a href="/wiki/Cyclodiol" title="Cyclodiol">Cyclodiol</a></li> <li><a href="/wiki/Cyclotriol" title="Cyclotriol">Cyclotriol</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA-S</a></li> <li><a href="/wiki/Ent-Estradiol" title="Ent-Estradiol"><i>ent</i>-Estradiol</a></li> <li><a href="/wiki/Epiestriol" title="Epiestriol">Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)</a></li> <li><a href="/wiki/Epimestrol" title="Epimestrol">Epimestrol</a></li> <li><a href="/wiki/Equilenin" title="Equilenin">Equilenin</a></li> <li><a href="/wiki/Equilin" title="Equilin">Equilin</a></li> <li><a href="/wiki/ERA-63" title="ERA-63">ERA-63 (ORG-37663)</a></li> <li><a href="/wiki/Esterified_estrogens" title="Esterified estrogens">Esterified estrogens</a></li> <li><a href="/wiki/Estetrol" title="Estetrol">Estetrol</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estradiol_esters" title="List of estrogen esters">Estradiol esters</a></li> <li><a href="/wiki/Lipoidal_estradiol" title="Lipoidal estradiol">Lipoidal estradiol</a></li> <li><a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">Polyestradiol phosphate</a></li></ul></li> <li><a href="/wiki/Estramustine" title="Estramustine">Estramustine</a></li> <li><a href="/wiki/Estramustine_phosphate" title="Estramustine phosphate">Estramustine phosphate</a></li> <li><a href="/wiki/Estrapronicate" title="Estrapronicate">Estrapronicate</a></li> <li><a href="/wiki/Estrazinol" title="Estrazinol">Estrazinol</a></li> <li><a href="/wiki/Estriol" title="Estriol">Estriol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estriol_esters" title="List of estrogen esters">Estriol esters</a></li> <li><a href="/wiki/Polyestriol_phosphate" title="Polyestriol phosphate">Polyestriol phosphate</a></li></ul></li> <li><a href="/wiki/Estrofurate" title="Estrofurate">Estrofurate</a></li> <li><a href="/wiki/Estrogenic_substances" title="Estrogenic substances">Estrogenic substances</a></li> <li><a href="/wiki/Estromustine" title="Estromustine">Estromustine</a></li> <li><a href="/wiki/Estrone" title="Estrone">Estrone</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estrone_esters" title="List of estrogen esters">Estrone esters</a></li> <li><a href="/wiki/Estrone_methyl_ether" title="Estrone methyl ether">Estrone methyl ether</a></li> <li><a href="/wiki/Estropipate" title="Estropipate">Estropipate</a></li></ul></li> <li><a href="/wiki/Etamestrol" title="Etamestrol">Etamestrol (eptamestrol)</a></li> <li><a href="/wiki/Ethinylandrostenediol" title="Ethinylandrostenediol">Ethinylandrostenediol</a> <ul><li><a href="/wiki/Ethandrostate" title="Ethandrostate">Ethandrostate</a></li></ul></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a> <ul><li><a href="/wiki/Ethinylestradiol_3-benzoate" class="mw-redirect" title="Ethinylestradiol 3-benzoate">Ethinylestradiol 3-benzoate</a></li> <li><a href="/wiki/Ethinylestradiol_sulfonate" title="Ethinylestradiol sulfonate">Ethinylestradiol sulfonate</a></li></ul></li> <li><a href="/wiki/Ethinylestriol" title="Ethinylestriol">Ethinylestriol</a></li> <li><a href="/wiki/Ethylestradiol" title="Ethylestradiol">Ethylestradiol</a></li> <li><a href="/wiki/Etynodiol" title="Etynodiol">Etynodiol</a></li> <li><a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">Etynodiol diacetate</a></li> <li><a href="/wiki/Hexolame" title="Hexolame">Hexolame</a></li> <li><a href="/wiki/Hippulin" title="Hippulin">Hippulin</a></li> <li><a href="/wiki/Hydroxyestrone_diacetate" title="Hydroxyestrone diacetate">Hydroxyestrone diacetate</a></li> <li><a href="/wiki/Lynestrenol" title="Lynestrenol">Lynestrenol</a></li> <li><a href="/wiki/Lynestrenol_phenylpropionate" title="Lynestrenol phenylpropionate">Lynestrenol phenylpropionate</a></li> <li><a href="/wiki/Mestranol" title="Mestranol">Mestranol</a></li> <li><a href="/wiki/Methylestradiol" title="Methylestradiol">Methylestradiol</a></li> <li><a href="/wiki/Moxestrol" title="Moxestrol">Moxestrol</a></li> <li><a href="/wiki/Mytatrienediol" title="Mytatrienediol">Mytatrienediol</a></li> <li><a href="/wiki/Nilestriol" title="Nilestriol">Nilestriol</a></li> <li><a href="/wiki/Norethisterone" title="Norethisterone">Norethisterone</a></li> <li><a href="/wiki/Noretynodrel" title="Noretynodrel">Noretynodrel</a></li> <li><a href="/wiki/Orestrate" title="Orestrate">Orestrate</a></li> <li><a href="/wiki/Pentolame" title="Pentolame">Pentolame</a></li> <li><a href="/wiki/Prodiame" title="Prodiame">Prodiame</a></li> <li><a href="/wiki/Prolame" title="Prolame">Prolame</a></li> <li><a href="/wiki/Promestriene" title="Promestriene">Promestriene</a></li> <li><a href="/wiki/RU-16117" title="RU-16117">RU-16117</a></li> <li><a href="/wiki/Quinestradol" title="Quinestradol">Quinestradol</a></li> <li><a href="/wiki/Quinestrol" title="Quinestrol">Quinestrol</a></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li></ul> <ul><li><i>Nonsteroidal:</i> <a href="/wiki/(R,R)-Tetrahydrochrysene" title="(R,R)-Tetrahydrochrysene">(R,R)-THC</a></li> <li><a href="/wiki/(S,S)-Tetrahydrochrysene" title="(S,S)-Tetrahydrochrysene">(S,S)-THC</a></li> <li><a href="/wiki/2,8-Dihydroxyhexahydrochrysene" title="2,8-Dihydroxyhexahydrochrysene">2,8-DHHHC</a></li> <li><a href="/w/index.php?title=%CE%92-LGND1&action=edit&redlink=1" class="new" title="Β-LGND1 (page does not exist)">β-LGND1</a></li> <li><a href="/wiki/%CE%92-LGND2" title="Β-LGND2">β-LGND2 (GTx-878)</a></li> <li><a href="/w/index.php?title=AC-186&action=edit&redlink=1" class="new" title="AC-186 (page does not exist)">AC-186</a></li> <li><a href="/wiki/Allenestrol" title="Allenestrol">Allenestrol</a></li> <li><a href="/wiki/Allenolic_acid" title="Allenolic acid">Allenolic acid</a></li> <li><a href="/wiki/Benzestrol" title="Benzestrol">Benzestrol</a></li> <li><a href="/wiki/Bifluranol" title="Bifluranol">Bifluranol</a></li> <li><a href="/wiki/Bisdehydrodoisynolic_acid" title="Bisdehydrodoisynolic acid">Bisdehydrodoisynolic acid</a></li> <li><a href="/wiki/Butestrol" title="Butestrol">Butestrol</a></li> <li><a href="/wiki/Carbestrol" title="Carbestrol">Carbestrol</a></li> <li><a href="/wiki/D-15414" title="D-15414">D-15414</a></li> <li><a href="/wiki/DCW234" title="DCW234">DCW234</a></li> <li><a href="/wiki/Diarylpropionitrile" title="Diarylpropionitrile">Diarylpropionitrile</a></li> <li><a href="/wiki/Dienestrol" title="Dienestrol">Dienestrol</a> <ul><li><a href="/wiki/Dienestrol_diacetate" title="Dienestrol diacetate">Dienestrol diacetate</a></li></ul></li> <li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Diethylstilbestrol_esters" title="List of estrogen esters">Diethylstilbestrol esters</a></li></ul></li> <li><a href="/wiki/Dimestrol" title="Dimestrol">Dimestrol (dianisylhexene)</a></li> <li><a href="/wiki/Dimethylstilbestrol" title="Dimethylstilbestrol">Dimethylstilbestrol</a></li> <li><a href="/wiki/Doisynoestrol" title="Doisynoestrol">Doisynoestrol (fenocycline)</a></li> <li><a href="/wiki/Doisynolic_acid" title="Doisynolic acid">Doisynolic acid</a></li> <li><a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Elacestrant" title="Elacestrant">Elacestrant</a></li> <li><a href="/wiki/ERB-196" title="ERB-196">ERB-196 (WAY-202196)</a></li> <li><a href="/wiki/Erteberel" title="Erteberel">Erteberel (SERBA-1, LY-500307)</a></li> <li><a href="/wiki/Estrobin" title="Estrobin">Estrobin (DBE)</a></li> <li><a href="/wiki/Fenestrel" title="Fenestrel">Fenestrel</a></li> <li><a href="/wiki/FERb_033" title="FERb 033">FERb 033</a></li> <li><a href="/wiki/Fosfestrol" title="Fosfestrol">Fosfestrol (diethylstilbestrol diphosphate)</a></li> <li><a href="/wiki/Furostilbestrol" title="Furostilbestrol">Furostilbestrol (diethylstilbestrol difuroate)</a></li> <li><a href="/wiki/GTx-758" title="GTx-758">GTx-758</a></li> <li><a href="/wiki/Hexestrol" title="Hexestrol">Hexestrol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Hexestrol_esters" title="List of estrogen esters">Hexestrol esters</a></li></ul></li> <li><a href="/wiki/ICI-85966" title="ICI-85966">ICI-85966 (Stilbostat)</a></li> <li><a href="/wiki/M2613" title="M2613">M2613</a></li> <li><a href="/wiki/Meso-Butestrol" title="Meso-Butestrol"><i>meso</i>-Butestrol</a></li> <li><a href="/wiki/Meso-Hexestrol" class="mw-redirect" title="Meso-Hexestrol"><i>meso</i>-Hexestrol</a></li> <li><a href="/wiki/Mestilbol" title="Mestilbol">Mestilbol</a></li> <li><a href="/wiki/Methallenestril" title="Methallenestril">Methallenestril</a></li> <li><a href="/wiki/Methestrol" title="Methestrol">Methestrol</a></li> <li><a href="/wiki/Methestrol_dipropionate" title="Methestrol dipropionate">Methestrol dipropionate</a></li> <li><a href="/wiki/Paroxypropione" title="Paroxypropione">Paroxypropione</a></li> <li><a href="/wiki/Pentafluranol" title="Pentafluranol">Pentafluranol</a></li> <li><a href="/wiki/Phenestrol" title="Phenestrol">Phenestrol</a></li> <li><a href="/wiki/Prinaberel" title="Prinaberel">Prinaberel (ERB-041, WAY-202041)</a></li> <li><a href="/wiki/Propylpyrazoletriol" title="Propylpyrazoletriol">Propylpyrazoletriol</a></li> <li><a href="/wiki/Quadrosilan" title="Quadrosilan">Quadrosilan</a></li> <li><a href="/w/index.php?title=SC-3296&action=edit&redlink=1" class="new" title="SC-3296 (page does not exist)">SC-3296</a></li> <li><a href="/wiki/SC-4289" title="SC-4289">SC-4289</a></li> <li><a href="/wiki/SERBA-2" title="SERBA-2">SERBA-2</a></li> <li><a href="/wiki/SKF-82,958" title="SKF-82,958">SKF-82,958</a></li> <li><a href="/wiki/Terfluranol" title="Terfluranol">Terfluranol</a></li> <li><a href="/wiki/Triphenylbromoethylene" title="Triphenylbromoethylene">Triphenylbromoethylene</a></li> <li><a href="/wiki/Triphenylchloroethylene" title="Triphenylchloroethylene">Triphenylchloroethylene</a></li> <li><a href="/wiki/Triphenyliodoethylene" title="Triphenyliodoethylene">Triphenyliodoethylene</a></li> <li><a href="/wiki/Triphenylmethylethylene" title="Triphenylmethylethylene">Triphenylmethylethylene (triphenylpropene)</a></li> <li><a href="/wiki/WAY-166818" title="WAY-166818">WAY-166818</a></li> <li><a href="/w/index.php?title=WAY-169916&action=edit&redlink=1" class="new" title="WAY-169916 (page does not exist)">WAY-169916</a></li> <li><a href="/wiki/WAY-200070" title="WAY-200070">WAY-200070</a></li> <li><a href="/wiki/WAY-204688" title="WAY-204688">WAY-204688 (SIM-688)</a></li> <li><a href="/wiki/WAY-214156" title="WAY-214156">WAY-214156</a></li></ul> <ul><li><i>Unknown/unsorted:</i> <a href="/wiki/ERB-26" title="ERB-26">ERB-26</a></li> <li><a href="/wiki/ERA-45" title="ERA-45">ERA-45</a></li> <li><a href="/wiki/ERB-79" title="ERB-79">ERB-79</a></li> <li><a href="/wiki/ZK-283197" title="ZK-283197">ZK-283197</a></li></ul> <ul><li><i>Xenoestrogens:</i> <a href="/wiki/Anise" title="Anise">Anise</a>-related (e.g., <a href="/wiki/Anethole" title="Anethole">anethole</a>, <a href="/wiki/Anol" title="Anol">anol</a>, <a href="/wiki/Dianethole" title="Dianethole">dianethole</a>, <a href="/wiki/Dianol" title="Dianol">dianol</a>, <a href="/wiki/Photoanethole" title="Photoanethole">photoanethole</a>)</li> <li><a href="/wiki/Chalconoid" title="Chalconoid">Chalconoids</a> (e.g., <a href="/wiki/Isoliquiritigenin" title="Isoliquiritigenin">isoliquiritigenin</a>, <a href="/wiki/Phloretin" title="Phloretin">phloretin</a>, <a href="/wiki/Phlorizin" title="Phlorizin">phlorizin (phloridzin)</a>, <a href="/wiki/Wedelolactone" title="Wedelolactone">wedelolactone</a>)</li> <li><a href="/wiki/Coumestan" title="Coumestan">Coumestans</a> (e.g., <a href="/wiki/Coumestrol" title="Coumestrol">coumestrol</a>, <a href="/wiki/Psoralidin" title="Psoralidin">psoralidin</a>)</li> <li><a href="/wiki/Flavonoid" title="Flavonoid">Flavonoids</a> (incl. <a href="/wiki/7,8-Dihydroxyflavone" class="mw-redirect" title="7,8-Dihydroxyflavone">7,8-DHF</a>, <a href="/wiki/8-Prenylnaringenin" title="8-Prenylnaringenin">8-prenylnaringenin</a>, <a href="/wiki/Apigenin" title="Apigenin">apigenin</a>, <a href="/wiki/Baicalein" title="Baicalein">baicalein</a>, <a href="/wiki/Baicalin" title="Baicalin">baicalin</a>, <a href="/wiki/Biochanin_A" title="Biochanin A">biochanin A</a>, <a href="/wiki/Calycosin" title="Calycosin">calycosin</a>, <a href="/wiki/Catechin" title="Catechin">catechin</a>, <a href="/wiki/Daidzein" title="Daidzein">daidzein</a>, <a href="/wiki/Daidzin" title="Daidzin">daidzin</a>, <a href="/wiki/Epicatechin_gallate" title="Epicatechin gallate">ECG</a>, <a href="/wiki/Epigallocatechin_gallate" title="Epigallocatechin gallate">EGCG</a>, <a href="/wiki/Epicatechin" class="mw-redirect" title="Epicatechin">epicatechin</a>, <a href="/wiki/Equol" title="Equol">equol</a>, <a href="/wiki/Formononetin" title="Formononetin">formononetin</a>, <a href="/wiki/Glabrene" title="Glabrene">glabrene</a>, <a href="/wiki/Glabridin" title="Glabridin">glabridin</a>, <a href="/wiki/Genistein" title="Genistein">genistein</a>, <a href="/wiki/Genistin" title="Genistin">genistin</a>, <a href="/wiki/Glycitein" title="Glycitein">glycitein</a>, <a href="/wiki/Kaempferol" title="Kaempferol">kaempferol</a>, <a href="/wiki/Liquiritigenin" title="Liquiritigenin">liquiritigenin</a>, <a href="/wiki/Mirificin" title="Mirificin">mirificin</a>, <a href="/wiki/Myricetin" title="Myricetin">myricetin</a>, <a href="/wiki/Naringenin" title="Naringenin">naringenin</a>, <a href="/w/index.php?title=Penduletin&action=edit&redlink=1" class="new" title="Penduletin (page does not exist)">penduletin</a>, <a href="/wiki/Pinocembrin" title="Pinocembrin">pinocembrin</a>, <a href="/wiki/Prunetin" title="Prunetin">prunetin</a>, <a href="/wiki/Puerarin" title="Puerarin">puerarin</a>, <a href="/wiki/Quercetin" title="Quercetin">quercetin</a>, <a href="/wiki/Tectoridin" title="Tectoridin">tectoridin</a>, <a href="/wiki/Tectorigenin" title="Tectorigenin">tectorigenin</a>)</li> <li><a href="/wiki/Lavender_oil" title="Lavender oil">Lavender oil</a></li> <li><a href="/wiki/Lignan" title="Lignan">Lignans</a> (e.g., <a href="/wiki/Enterodiol" title="Enterodiol">enterodiol</a>, <a href="/wiki/Enterolactone" title="Enterolactone">enterolactone</a>, <a href="/wiki/Nyasol" title="Nyasol">nyasol (<i>cis</i>-hinokiresinol)</a>)</li> <li><a href="/wiki/Metalloestrogen" title="Metalloestrogen">Metalloestrogens</a> (e.g., <a href="/wiki/Cadmium" title="Cadmium">cadmium</a>)</li> <li><a href="/wiki/Pesticide" title="Pesticide">Pesticides</a> (e.g., <a href="/wiki/Alternariol" title="Alternariol">alternariol</a>, <a href="/wiki/Dieldrin" title="Dieldrin">dieldrin</a>, <a href="/wiki/Endosulfan" title="Endosulfan">endosulfan</a>, <a href="/wiki/Fenarimol" title="Fenarimol">fenarimol</a>, <a href="/wiki/HPTE" title="HPTE">HPTE</a>, <a href="/wiki/Methiocarb" title="Methiocarb">methiocarb</a>, <a href="/wiki/Methoxychlor" title="Methoxychlor">methoxychlor</a>, <a href="/wiki/Triclocarban" title="Triclocarban">triclocarban</a>, <a href="/wiki/Triclosan" title="Triclosan">triclosan</a>)</li> <li><a href="/wiki/Phytosteroid" title="Phytosteroid">Phytosteroids</a> (e.g., <a href="/wiki/Digitoxin" title="Digitoxin">digitoxin</a> (<a href="/wiki/Digitalis" title="Digitalis">digitalis</a>), <a href="/wiki/Diosgenin" title="Diosgenin">diosgenin</a>, <a href="/wiki/Guggulsterone" title="Guggulsterone">guggulsterone</a>)</li> <li><a href="/wiki/Phytosterol" title="Phytosterol">Phytosterols</a> (e.g., <a href="/wiki/%CE%92-sitosterol" class="mw-redirect" title="Β-sitosterol">β-sitosterol</a>, <a href="/wiki/Campesterol" title="Campesterol">campesterol</a>, <a href="/wiki/Stigmasterol" title="Stigmasterol">stigmasterol</a>)</li> <li><a href="/wiki/Resorcylic_acid_lactone" title="Resorcylic acid lactone">Resorcylic acid lactones</a> (e.g., <a href="/wiki/Zearalanone" title="Zearalanone">zearalanone</a>, <a href="/wiki/%CE%91-zearalenol" class="mw-redirect" title="Α-zearalenol">α-zearalenol</a>, <a href="/wiki/%CE%92-zearalenol" class="mw-redirect" title="Β-zearalenol">β-zearalenol</a>, <a href="/wiki/Zearalenone" title="Zearalenone">zearalenone</a>, <a href="/wiki/Zeranol" title="Zeranol">zeranol (α-zearalanol)</a>, <a href="/wiki/Taleranol" title="Taleranol">taleranol (teranol, β-zearalanol)</a>)</li> <li><a href="/wiki/Steroid" title="Steroid">Steroid</a>-like (e.g., <a href="/wiki/Deoxymiroestrol" class="mw-redirect" title="Deoxymiroestrol">deoxymiroestrol</a>, <a href="/wiki/Miroestrol" title="Miroestrol">miroestrol</a>)</li> <li><a href="/wiki/Stilbenoid" title="Stilbenoid">Stilbenoids</a> (e.g., <a href="/wiki/Resveratrol" title="Resveratrol">resveratrol</a>, <a href="/wiki/Rhaponticin" title="Rhaponticin">rhaponticin</a>)</li> <li><a href="/wiki/Synthetic_xenoestrogen" class="mw-redirect" title="Synthetic xenoestrogen">Synthetic xenoestrogens</a> (e.g., <a href="/wiki/Alkylphenol" title="Alkylphenol">alkylphenols</a>, <a href="/wiki/Bisphenol" title="Bisphenol">bisphenols</a> (e.g., <a href="/wiki/Bisphenol_A" title="Bisphenol A">BPA</a>, <a href="/wiki/Bisphenol_F" title="Bisphenol F">BPF</a>, <a href="/wiki/Bisphenol_S" title="Bisphenol S">BPS</a>), <a href="/wiki/Dichlorodiphenyltrichloroethane" class="mw-redirect" title="Dichlorodiphenyltrichloroethane">DDT</a>, <a href="/wiki/Paraben" title="Paraben">parabens</a>, <a href="/wiki/Polybrominated_biphenyl" title="Polybrominated biphenyl">PBBs</a>, <a href="/wiki/4-hydroxybenzoic_acid" class="mw-redirect" title="4-hydroxybenzoic acid">PHBA</a>, <a href="/wiki/Phthalate" class="mw-redirect" title="Phthalate">phthalates</a>, <a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">PCBs</a>)</li> <li>Others (e.g., <a href="/wiki/Agnuside" title="Agnuside">agnuside</a>, <a href="/w/index.php?title=Rotundifuran&action=edit&redlink=1" class="new" title="Rotundifuran (page does not exist)">rotundifuran</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Mixed<br />(<a href="/wiki/Selective_estrogen_receptor_modulators" class="mw-redirect" title="Selective estrogen receptor modulators"><abbr title="Selective estrogen receptor modulators">SERMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Selective estrogen receptor modulators</span>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Phenylbenzofuran" title="2-Phenylbenzofuran">2-Phenylbenzofuran</a></li> <li><a href="/w/index.php?title=2-Phenylbenzothiophene&action=edit&redlink=1" class="new" title="2-Phenylbenzothiophene (page does not exist)">2-Phenylbenzothiophene</a></li> <li><a href="/wiki/4%27-Hydroxynorendoxifen" title="4'-Hydroxynorendoxifen">4'-Hydroxynorendoxifen</a></li> <li><a href="/wiki/27-Hydroxycholesterol" title="27-Hydroxycholesterol">27-Hydroxycholesterol</a></li> <li><a href="/wiki/Acefluranol" title="Acefluranol">Acefluranol</a></li> <li><a href="/wiki/Acolbifene" title="Acolbifene">Acolbifene</a></li> <li><a href="/wiki/Afimoxifene" title="Afimoxifene">Afimoxifene</a></li> <li><a href="/wiki/Anordiol" title="Anordiol">Anordiol</a></li> <li><a href="/wiki/Anordrin" title="Anordrin">Anordrin</a></li> <li><a href="/wiki/Arzoxifene" title="Arzoxifene">Arzoxifene</a></li> <li><a href="/wiki/Bazedoxifene" title="Bazedoxifene">Bazedoxifene</a></li> <li><a href="/wiki/Brilanestrant" title="Brilanestrant">Brilanestrant</a></li> <li><a href="/wiki/Broparestrol" title="Broparestrol">Broparestrol</a></li> <li><a href="/wiki/Camizestrant" title="Camizestrant">Camizestrant</a></li> <li><a href="/wiki/Chlorotrianisene" title="Chlorotrianisene">Chlorotrianisene</a></li> <li><a href="/wiki/Clomifene" title="Clomifene">Clomifene</a></li> <li><a href="/wiki/Clomifenoxide" title="Clomifenoxide">Clomifenoxide</a></li> <li><a href="/w/index.php?title=CN-55945-27&action=edit&redlink=1" class="new" title="CN-55945-27 (page does not exist)">CN-55945-27</a></li> <li><a href="/wiki/Cyclofenil" title="Cyclofenil">Cyclofenil</a></li> <li><a href="/w/index.php?title=D-15413&action=edit&redlink=1" class="new" title="D-15413 (page does not exist)">D-15413</a></li> <li><a href="/wiki/Desmethylchlorotrianisene" title="Desmethylchlorotrianisene">Desmethylchlorotrianisene</a></li> <li><a href="/wiki/Droloxifene" title="Droloxifene">Droloxifene</a></li> <li><a href="/wiki/Enclomifene" title="Enclomifene">Enclomifene</a></li> <li><a href="/wiki/Endoxifen" title="Endoxifen">Endoxifen</a></li> <li><a href="/wiki/Etacstil" title="Etacstil">Etacstil (GW-5638, DPC-974)</a></li> <li><a href="/wiki/Ethamoxytriphetol" title="Ethamoxytriphetol">Ethamoxytriphetol (MER-25)</a></li> <li><a href="/wiki/Femarelle" title="Femarelle">Femarelle</a></li> <li><a href="/wiki/Fispemifene" title="Fispemifene">Fispemifene</a></li> <li><a href="/w/index.php?title=GW-7604&action=edit&redlink=1" class="new" title="GW-7604 (page does not exist)">GW-7604</a></li> <li><a href="/wiki/ICI-55548" class="mw-redirect" title="ICI-55548">ICI-55548</a></li> <li><a href="/wiki/Idoxifene" title="Idoxifene">Idoxifene</a></li> <li><a href="/wiki/Lasofoxifene" title="Lasofoxifene">Lasofoxifene</a></li> <li><a href="/wiki/Levormeloxifene" title="Levormeloxifene">Levormeloxifene</a></li> <li><a href="/wiki/LN-1643" class="mw-redirect" title="LN-1643">LN-1643</a></li> <li><a href="/wiki/LN-2299" class="mw-redirect" title="LN-2299">LN-2299</a></li> <li><a href="/w/index.php?title=LY-117018&action=edit&redlink=1" class="new" title="LY-117018 (page does not exist)">LY-117018</a></li> <li><a href="/wiki/Menerba" title="Menerba">Menerba</a></li> <li><a href="/wiki/Miproxifene" title="Miproxifene">Miproxifene</a></li> <li><a href="/wiki/Miproxifene_phosphate" title="Miproxifene phosphate">Miproxifene phosphate</a></li> <li><a href="/w/index.php?title=MRL-37&action=edit&redlink=1" class="new" title="MRL-37 (page does not exist)">MRL-37</a></li> <li><a href="/wiki/Nafoxidine" title="Nafoxidine">Nafoxidine</a></li> <li><a href="/wiki/Nitromifene" title="Nitromifene">Nitromifene</a></li> <li><a href="/wiki/NNC_45-0095" title="NNC 45-0095">NNC 45-0095</a></li> <li><a href="/w/index.php?title=NNC_45-0320&action=edit&redlink=1" class="new" title="NNC 45-0320 (page does not exist)">NNC 45-0320</a></li> <li><a href="/w/index.php?title=NNC_45-0781&action=edit&redlink=1" class="new" title="NNC 45-0781 (page does not exist)">NNC 45-0781</a></li> <li><a href="/w/index.php?title=NNC_45-1506&action=edit&redlink=1" class="new" title="NNC 45-1506 (page does not exist)">NNC 45-1506</a></li> <li><a href="/wiki/Ormeloxifene" title="Ormeloxifene">Ormeloxifene</a></li> <li><a href="/wiki/Ospemifene" title="Ospemifene">Ospemifene</a></li> <li><a href="/wiki/Panomifene" title="Panomifene">Panomifene</a></li> <li><a href="/wiki/Pipendoxifene" title="Pipendoxifene">Pipendoxifene</a></li> <li><a href="/w/index.php?title=Promensil&action=edit&redlink=1" class="new" title="Promensil (page does not exist)">Promensil</a></li> <li><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></li> <li><a href="/wiki/Rimostil" title="Rimostil">Rimostil (P-081)</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/w/index.php?title=SS1010&action=edit&redlink=1" class="new" title="SS1010 (page does not exist)">SS1010</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a></li> <li><a href="/wiki/TAS-108" title="TAS-108">TAS-108 (SR-16234)</a></li> <li><a href="/wiki/Toremifene" title="Toremifene">Toremifene</a></li> <li><a href="/wiki/Trioxifene" title="Trioxifene">Trioxifene</a></li> <li><a href="/w/index.php?title=TZE-5323&action=edit&redlink=1" class="new" title="TZE-5323 (page does not exist)">TZE-5323</a></li> <li><a href="/w/index.php?title=U-11555A&action=edit&redlink=1" class="new" title="U-11555A (page does not exist)">U-11555A</a></li> <li><a href="/w/index.php?title=U-11634&action=edit&redlink=1" class="new" title="U-11634 (page does not exist)">U-11634</a></li> <li><a href="/w/index.php?title=Y-134&action=edit&redlink=1" class="new" title="Y-134 (page does not exist)">Y-134</a></li> <li><a href="/wiki/Zindoxifene" title="Zindoxifene">Zindoxifene</a></li> <li><a href="/wiki/Zuclomifene" title="Zuclomifene">Zuclomifene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/(R,R)-Tetrahydrochrysene" title="(R,R)-Tetrahydrochrysene">(R,R)-THC</a></li> <li><a href="/wiki/7%CE%B2-Hydroxy-DHEA" title="7β-Hydroxy-DHEA">7β-Hydroxy-DHEA</a></li> <li><a href="/w/index.php?title=Chloroindazole&action=edit&redlink=1" class="new" title="Chloroindazole (page does not exist)">Chloroindazole</a></li> <li><a href="/wiki/Cytestrol_acetate" title="Cytestrol acetate">Cytestrol acetate</a></li> <li><a href="/w/index.php?title=EM-800&action=edit&redlink=1" class="new" title="EM-800 (page does not exist)">EM-800 (SCH-57050)</a></li> <li><a href="/wiki/Epitiostanol" title="Epitiostanol">Epitiostanol</a></li> <li><a href="/w/index.php?title=ERA-90&action=edit&redlink=1" class="new" title="ERA-90 (page does not exist)">ERA-90</a></li> <li><a href="/w/index.php?title=ERB-88&action=edit&redlink=1" class="new" title="ERB-88 (page does not exist)">ERB-88</a></li> <li><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant (ICI-182780)</a></li> <li><a href="/wiki/Glyceollin" title="Glyceollin">Glyceollins</a> (<a href="/wiki/Glyceollin_I" title="Glyceollin I">I</a>, <a href="/w/index.php?title=Glyceollin_II&action=edit&redlink=1" class="new" title="Glyceollin II (page does not exist)">II</a>, <a href="/wiki/Glyceollin_III" title="Glyceollin III">III</a>, <a href="/w/index.php?title=Glyceollin_IV&action=edit&redlink=1" class="new" title="Glyceollin IV (page does not exist)">IV</a>)</li> <li><a href="/wiki/ICI-164384" title="ICI-164384">ICI-164384</a></li> <li><a href="/w/index.php?title=MDL-101906&action=edit&redlink=1" class="new" title="MDL-101906 (page does not exist)">MDL-101906</a></li> <li><a href="/wiki/Mepitiostane" title="Mepitiostane">Mepitiostane</a></li> <li><a href="/wiki/Methylepitiostanol" title="Methylepitiostanol">Methylepitiostanol</a></li> <li><a href="/wiki/Methylpiperidinopyrazole" title="Methylpiperidinopyrazole">Methylpiperidinopyrazole</a></li> <li><a href="/wiki/MIBE" title="MIBE">MIBE</a></li> <li><a href="/w/index.php?title=Oxabicycloheptene_sulfonate&action=edit&redlink=1" class="new" title="Oxabicycloheptene sulfonate (page does not exist)">Oxabicycloheptene sulfonate</a></li> <li><a href="/wiki/Phenytoin" title="Phenytoin">Phenytoin</a></li> <li><a href="/wiki/PHTPP" title="PHTPP">PHTPP</a></li> <li><a href="/wiki/Prochloraz" title="Prochloraz">Prochloraz</a></li> <li><a href="/w/index.php?title=RU-39411&action=edit&redlink=1" class="new" title="RU-39411 (page does not exist)">RU-39411</a></li> <li><a href="/w/index.php?title=RU-58668&action=edit&redlink=1" class="new" title="RU-58668 (page does not exist)">RU-58668</a></li> <li><a href="/w/index.php?title=SS1020&action=edit&redlink=1" class="new" title="SS1020 (page does not exist)">SS1020</a></li> <li><a href="/wiki/TAS-108" title="TAS-108">TAS-108 (SR-16234)</a></li> <li><a href="/wiki/ZB716" title="ZB716">ZB716</a></li> <li><a href="/w/index.php?title=ZK-164015&action=edit&redlink=1" class="new" title="ZK-164015 (page does not exist)">ZK-164015</a></li> <li><a href="/w/index.php?title=ZK-191703&action=edit&redlink=1" class="new" title="ZK-191703 (page does not exist)">ZK-191703</a></li></ul> <ul><li><i>Coregulator-binding modulators:</i> <a href="/wiki/ERX-11" title="ERX-11">ERX-11</a></li></ul> <ul><li><i>Noncompetitive inhibitors:</i> <a href="/wiki/Trilostane" title="Trilostane">Trilostane</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/G_protein-coupled_estrogen_receptor" class="mw-redirect" title="G protein-coupled estrogen receptor"><abbr title="G protein-coupled estrogen receptor">GPER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip G protein-coupled estrogen receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Methoxyestradiol" title="2-Methoxyestradiol">2-Methoxyestradiol</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/Afimoxifene" title="Afimoxifene">Afimoxifene (4-hydroxytamoxifen)</a></li> <li><a href="/wiki/Aldosterone" title="Aldosterone">Aldosterone</a></li> <li><a href="/wiki/Atrazine" title="Atrazine">Atrazine</a></li> <li><a href="/wiki/Bisphenol_A" title="Bisphenol A">Bisphenol A</a></li> <li><a href="/wiki/Daidzein" title="Daidzein">Daidzein</a></li> <li><a href="/wiki/DDT" title="DDT">DDT</a> (<a href="/wiki/P,p%27-DDT" class="mw-redirect" title="P,p'-DDT">p,p'-DDT</a>, <a href="/w/index.php?title=O%27,p%27-DDE&action=edit&redlink=1" class="new" title="O',p'-DDE (page does not exist)">o',p'-DDE</a>)</li> <li><a href="/wiki/Diarylpropionitrile" title="Diarylpropionitrile">Diarylpropionitrile</a></li> <li><a href="/wiki/Equol" title="Equol">Equol</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a></li> <li><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant (ICI-182780)</a></li> <li><a href="/wiki/G-1_(drug)" class="mw-redirect" title="G-1 (drug)">G-1</a></li> <li><a href="/wiki/Genistein" title="Genistein">Genistein</a></li> <li><a href="/w/index.php?title=GPER-L1&action=edit&redlink=1" class="new" title="GPER-L1 (page does not exist)">GPER-L1</a></li> <li><a href="/w/index.php?title=GPER-L2&action=edit&redlink=1" class="new" title="GPER-L2 (page does not exist)">GPER-L2</a></li> <li><a href="/wiki/Hydroxytyrosol" title="Hydroxytyrosol">Hydroxytyrosol</a></li> <li><a href="/wiki/Kepone" class="mw-redirect" title="Kepone">Kepone</a></li> <li><a href="/wiki/Nicotinic_acid" title="Nicotinic acid">Nicotinic acid</a></li> <li><a href="/wiki/Nicotinamide" title="Nicotinamide">Nicotinamide</a></li> <li><a href="/wiki/Nonylphenol" title="Nonylphenol">Nonylphenol</a></li> <li><a href="/wiki/Oleuropein" title="Oleuropein">Oleuropein</a></li> <li><a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">PCBs</a> (<a href="/w/index.php?title=2,2%27,5%27-PCB-4-OH&action=edit&redlink=1" class="new" title="2,2',5'-PCB-4-OH (page does not exist)">2,2',5'-PCB-4-OH</a>)</li> <li><a href="/wiki/Propylpyrazoletriol" title="Propylpyrazoletriol">Propylpyrazoletriol</a></li> <li><a href="/wiki/Quercetin" title="Quercetin">Quercetin</a></li> <li><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></li> <li><a href="/wiki/Resveratrol" title="Resveratrol">Resveratrol</a></li> <li><a href="/w/index.php?title=STX_(drug)&action=edit&redlink=1" class="new" title="STX (drug) (page does not exist)">STX</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a></li> <li><a href="/wiki/Tectoridin" title="Tectoridin">Tectoridin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/CCL18" title="CCL18">CCL18</a></li> <li><a href="/wiki/Estriol" title="Estriol">Estriol</a></li> <li><a href="/w/index.php?title=G-15_(drug)&action=edit&redlink=1" class="new" title="G-15 (drug) (page does not exist)">G-15</a></li> <li><a href="/w/index.php?title=G-36_(drug)&action=edit&redlink=1" class="new" title="G-36 (drug) (page does not exist)">G-36</a></li> <li><a href="/wiki/MIBE" title="MIBE">MIBE</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Unknown</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a></li> <li><a href="/wiki/Zearalenone" title="Zearalenone">Zearalenone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Estrogens_and_antiestrogens" title="Template:Estrogens and antiestrogens">Estrogens and antiestrogens</a></dd> <dd><a href="/wiki/Template:Androgen_receptor_modulators" title="Template:Androgen receptor modulators">Androgen receptor modulators</a></dd> <dd><a href="/wiki/Template:Progesterone_receptor_modulators" title="Template:Progesterone receptor modulators">Progesterone receptor modulators</a></dd> <dd><a href="/wiki/List_of_steroidal_estrogens" class="mw-redirect" title="List of steroidal estrogens">List of estrogens</a></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="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</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center"><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><i>Cortisol-like and related (16-unsubstituted):</i> <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">Δ<sup>7</sup>-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)">Δ<sup>7</sup>-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><i>Methasones and related (16-substituted):</i> <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><i>Cyclic ketals (16,17-cyclized):</i> <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><i>Others/atypical (other expanded steroid ring systems, homosteroids, and non-pregnane steroids):</i> <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><i>Non-corticosteroids with some glucocorticoid activity:</i> <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 class="mw-selflink selflink">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 href="/wiki/Progesterone" title="Progesterone">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><i>Nonsteroidal glucocorticoids:</i> <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<br />(<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</span>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/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><i>Antisense oligonucleotides:</i> <a href="/wiki/IONIS-GCCRRx" title="IONIS-GCCRRx">IONIS-GCCR<sub>Rx</sub> (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="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</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Progesterone derivatives:</i> <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 href="/wiki/Progesterone" title="Progesterone">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><i>Retroprogesterone derivatives:</i> <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><i>17α-Substituted progesterone derivatives:</i> <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><i>19-Norprogesterone derivatives:</i> <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><i>Testosterone derivatives:</i> 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 class="mw-selflink selflink">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><i>Spirolactone derivatives:</i> <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><i>Nonsteroidal:</i> <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><i>Unknown:</i> <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<br />(<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</span>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Steroidal:</i> <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><i>Nonsteroidal:</i> <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><i>Steroidal:</i> <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><i>Nonsteroidal:</i> <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</span><br />(<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</span>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/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 href="/wiki/Progesterone" title="Progesterone">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="Other_sex_hormones_and_modulators_of_the_genital_system_(G03X)248" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Other_sex_hormones_and_modulators_of_the_genital_system" title="Template:Other sex hormones and modulators of the genital system"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Other_sex_hormones_and_modulators_of_the_genital_system" title="Template talk:Other sex hormones and modulators of the genital system"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a 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gonadotropin">Pmsg</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antiprogestogen" title="Antiprogestogen">Antiprogestogens</a> (G03XB)</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/Mifepristone" title="Mifepristone">Mifepristone</a></li> <li><a href="/wiki/Ulipristal_acetate" title="Ulipristal acetate">Ulipristal</a></li> <li><a href="/wiki/Aglepristone" title="Aglepristone">Aglepristone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Selective_estrogen_receptor_modulator" title="Selective estrogen receptor modulator">Selective estrogen<br />receptor modulators</a> (G03XC)</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/Raloxifene" title="Raloxifene">Raloxifene</a></li> 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