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</li> <li id="toc-High_blood_pressure" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#High_blood_pressure"> <div class="vector-toc-text"> 1.2 High blood pressure </div> </a> <ul id="toc-High_blood_pressure-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-High_aldosterone_levels" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#High_aldosterone_levels"> <div class="vector-toc-text"> 1.3 High aldosterone levels </div> </a> <ul id="toc-High_aldosterone_levels-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Skin_and_hair_conditions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Skin_and_hair_conditions"> <div class="vector-toc-text"> 1.4 Skin and hair conditions </div> </a> <ul id="toc-Skin_and_hair_conditions-sublist" class="vector-toc-list"> <li id="toc-Comparison" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Comparison"> <div class="vector-toc-text"> 1.4.1 Comparison </div> </a> <ul id="toc-Comparison-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Transgender_hormone_therapy" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Transgender_hormone_therapy"> <div class="vector-toc-text"> 1.5 Transgender hormone therapy </div> </a> <ul id="toc-Transgender_hormone_therapy-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Forms" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Forms"> <div class="vector-toc-text"> 1.6 Forms </div> </a> <ul id="toc-Forms-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Contraindications" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Contraindications"> <div class="vector-toc-text"> 2 Contraindications </div> </a> <ul id="toc-Contraindications-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Side_effects" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Side_effects"> <div class="vector-toc-text"> 3 Side effects </div> </a> <button aria-controls="toc-Side_effects-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Side effects subsection </button> <ul id="toc-Side_effects-sublist" class="vector-toc-list"> <li id="toc-High_potassium_levels" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#High_potassium_levels"> <div class="vector-toc-text"> 3.1 High potassium levels </div> </a> <ul id="toc-High_potassium_levels-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Breast_changes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Breast_changes"> <div class="vector-toc-text"> 3.2 Breast changes </div> </a> <ul id="toc-Breast_changes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Menstrual_disturbances" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Menstrual_disturbances"> <div class="vector-toc-text"> 3.3 Menstrual disturbances </div> </a> <ul id="toc-Menstrual_disturbances-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Mood_changes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Mood_changes"> <div class="vector-toc-text"> 3.4 Mood changes </div> </a> <ul id="toc-Mood_changes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Lipid_changes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Lipid_changes"> <div class="vector-toc-text"> 3.5 Lipid changes </div> </a> <ul id="toc-Lipid_changes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Rare_reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Rare_reactions"> <div class="vector-toc-text"> 3.6 Rare reactions </div> </a> <ul id="toc-Rare_reactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Spironolactone_bodies" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Spironolactone_bodies"> <div class="vector-toc-text"> 3.7 Spironolactone bodies </div> </a> <ul id="toc-Spironolactone_bodies-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pregnancy_and_breastfeeding" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pregnancy_and_breastfeeding"> <div class="vector-toc-text"> 3.8 Pregnancy and breastfeeding </div> </a> <ul id="toc-Pregnancy_and_breastfeeding-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Overdose" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Overdose"> <div class="vector-toc-text"> 4 Overdose </div> </a> <ul id="toc-Overdose-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Interactions" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Interactions"> <div class="vector-toc-text"> 5 Interactions </div> </a> <ul id="toc-Interactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pharmacology" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Pharmacology"> <div class="vector-toc-text"> 6 Pharmacology </div> </a> <button aria-controls="toc-Pharmacology-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Pharmacology subsection </button> <ul id="toc-Pharmacology-sublist" class="vector-toc-list"> <li id="toc-Pharmacodynamics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmacodynamics"> <div class="vector-toc-text"> 6.1 Pharmacodynamics </div> </a> <ul id="toc-Pharmacodynamics-sublist" class="vector-toc-list"> </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"> 6.2 Pharmacokinetics </div> </a> <ul id="toc-Pharmacokinetics-sublist" class="vector-toc-list"> <li id="toc-Absorption" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Absorption"> <div class="vector-toc-text"> 6.2.1 Absorption </div> </a> <ul id="toc-Absorption-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Distribution" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Distribution"> <div class="vector-toc-text"> 6.2.2 Distribution </div> </a> <ul id="toc-Distribution-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metabolism" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Metabolism"> <div class="vector-toc-text"> 6.2.3 Metabolism </div> </a> <ul id="toc-Metabolism-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Elimination" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Elimination"> <div class="vector-toc-text"> 6.2.4 Elimination </div> </a> <ul id="toc-Elimination-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Chemistry" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Chemistry"> <div class="vector-toc-text"> 7 Chemistry </div> </a> <button aria-controls="toc-Chemistry-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Chemistry subsection </button> <ul id="toc-Chemistry-sublist" class="vector-toc-list"> <li id="toc-Names" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Names"> <div class="vector-toc-text"> 7.1 Names </div> </a> <ul id="toc-Names-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Analogues" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Analogues"> <div class="vector-toc-text"> 7.2 Analogues </div> </a> <ul id="toc-Analogues-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Synthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Synthesis"> <div class="vector-toc-text"> 7.3 Synthesis </div> </a> <ul id="toc-Synthesis-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> 8 History </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Society_and_culture" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Society_and_culture"> <div class="vector-toc-text"> 9 Society and culture </div> </a> <button aria-controls="toc-Society_and_culture-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Society and culture subsection </button> <ul id="toc-Society_and_culture-sublist" class="vector-toc-list"> <li id="toc-Generic_names" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Generic_names"> <div class="vector-toc-text"> 9.1 Generic names </div> </a> <ul id="toc-Generic_names-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Brand_names" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Brand_names"> <div class="vector-toc-text"> 9.2 Brand names </div> </a> <ul id="toc-Brand_names-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Availability" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Availability"> <div class="vector-toc-text"> 9.3 Availability </div> </a> <ul id="toc-Availability-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Research" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Research"> <div class="vector-toc-text"> 10 Research </div> </a> <button aria-controls="toc-Research-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Research subsection </button> <ul id="toc-Research-sublist" class="vector-toc-list"> <li id="toc-Prostate_conditions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Prostate_conditions"> <div class="vector-toc-text"> 10.1 Prostate conditions </div> </a> <ul id="toc-Prostate_conditions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Epstein–Barr_virus" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Epstein–Barr_virus"> <div class="vector-toc-text"> 10.2 Epstein–Barr virus </div> </a> <ul id="toc-Epstein–Barr_virus-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_conditions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other_conditions"> <div class="vector-toc-text"> 10.3 Other conditions </div> </a> <ul id="toc-Other_conditions-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> 11 References </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" > Toggle the table of contents </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading">Spironolactone</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 34 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-34" aria-hidden="true" > 34 languages </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%B3%D8%A8%D9%8A%D8%B1%D9%88%D9%86%D9%88%D9%84%D8%A7%D9%83%D8%AA%D9%88%D9%86" title="سبيرونولاكتون – Arabic" lang="ar" hreflang="ar" data-title="سبيرونولاكتون" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target">العربية</a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A7%D8%B3%D9%BE%DB%8C%D8%B1%D9%88%D9%86%D9%88%D9%84%D8%A7%DA%A9%D8%AA%D9%88%D9%86" title="اسپیرونولاکتون – South Azerbaijani" lang="azb" hreflang="azb" data-title="اسپیرونولاکتون" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target">تۆرکجه</a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Espironolactona" title="Espironolactona – Catalan" lang="ca" hreflang="ca" data-title="Espironolactona" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target">Català</a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Spironolacton" title="Spironolacton – Welsh" lang="cy" hreflang="cy" data-title="Spironolacton" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target">Cymraeg</a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Spironolacton" title="Spironolacton – German" lang="de" hreflang="de" data-title="Spironolacton" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target">Deutsch</a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A3%CF%80%CE%B5%CE%B9%CF%81%CE%BF%CE%BD%CE%BF%CE%BB%CE%B1%CE%BA%CF%84%CF%8C%CE%BD%CE%B7" title="Σπειρονολακτόνη – Greek" lang="el" hreflang="el" data-title="Σπειρονολακτόνη" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target">Ελληνικά</a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Espironolactona" title="Espironolactona – Spanish" lang="es" hreflang="es" data-title="Espironolactona" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target">Español</a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Spironolaktono" title="Spironolaktono – Esperanto" lang="eo" hreflang="eo" data-title="Spironolaktono" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target">Esperanto</a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Espironolaktona" title="Espironolaktona – Basque" lang="eu" hreflang="eu" data-title="Espironolaktona" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target">Euskara</a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%D8%B3%D9%BE%DB%8C%D8%B1%D9%88%D9%86%D9%88%D9%84%D8%A7%DA%A9%D8%AA%D9%88%D9%86" title="اسپیرونولاکتون – Persian" lang="fa" hreflang="fa" data-title="اسپیرونولاکتون" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target">فارسی</a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Spironolactone" title="Spironolactone – French" lang="fr" hreflang="fr" data-title="Spironolactone" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target">Français</a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%8A%A4%ED%94%BC%EB%A1%9C%EB%86%80%EB%9D%BD%ED%86%A4" title="스피로놀락톤 – Korean" lang="ko" hreflang="ko" data-title="스피로놀락톤" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target">한국어</a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%8D%D5%BA%D5%AB%D6%80%D5%B8%D5%B6%D5%B8%D5%AC%D5%A1%D5%AF%D5%BF%D5%B8%D5%B6" title="Սպիրոնոլակտոն – Armenian" lang="hy" hreflang="hy" data-title="Սպիրոնոլակտոն" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target">Հայերեն</a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Spironolakton" title="Spironolakton – Croatian" lang="hr" hreflang="hr" data-title="Spironolakton" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target">Hrvatski</a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Spironolakton" title="Spironolakton – Indonesian" lang="id" hreflang="id" data-title="Spironolakton" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target">Bahasa Indonesia</a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Spironolattone" title="Spironolattone – Italian" lang="it" hreflang="it" data-title="Spironolattone" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target">Italiano</a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Spironolaktons" title="Spironolaktons – Latvian" lang="lv" hreflang="lv" data-title="Spironolaktons" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target">Latviešu</a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Spironolakton" title="Spironolakton – Hungarian" lang="hu" hreflang="hu" data-title="Spironolakton" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target">Magyar</a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Spironolacton" title="Spironolacton – Dutch" lang="nl" hreflang="nl" data-title="Spironolacton" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target">Nederlands</a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%B9%E3%83%94%E3%83%AD%E3%83%8E%E3%83%A9%E3%82%AF%E3%83%88%E3%83%B3" title="スピロノラクトン – Japanese" lang="ja" hreflang="ja" data-title="スピロノラクトン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target">日本語</a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Spironolakton" title="Spironolakton – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Spironolakton" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target">Norsk bokmål</a></li><li class="interlanguage-link interwiki-or mw-list-item"><a href="https://or.wikipedia.org/wiki/%E0%AC%B8%E0%AD%8D%E0%AC%AA%E0%AC%BE%E0%AC%87%E0%AC%B0%E0%AD%8B%E0%AC%A8%E0%AD%8B%E0%AC%B2%E0%AC%BE%E0%AC%95%E0%AD%8D%E0%AC%9F%E0%AD%8B%E0%AC%A8" title="ସ୍ପାଇରୋନୋଲାକ୍ଟୋନ – Odia" lang="or" hreflang="or" data-title="ସ୍ପାଇରୋନୋଲାକ୍ଟୋନ" data-language-autonym="ଓଡ଼ିଆ" data-language-local-name="Odia" class="interlanguage-link-target">ଓଡ଼ିଆ</a></li><li class="interlanguage-link interwiki-ps mw-list-item"><a href="https://ps.wikipedia.org/wiki/%D8%B3%D9%BE%D9%8A%D8%B1%D9%88%D9%86%D9%88%D9%84%DA%A9%D9%BC%D9%88%D9%86" title="سپيرونولکټون – Pashto" lang="ps" hreflang="ps" data-title="سپيرونولکټون" data-language-autonym="پښتو" data-language-local-name="Pashto" class="interlanguage-link-target">پښتو</a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Spironolakton" title="Spironolakton – Polish" lang="pl" hreflang="pl" data-title="Spironolakton" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target">Polski</a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Espironolactona" title="Espironolactona – Portuguese" lang="pt" hreflang="pt" data-title="Espironolactona" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target">Português</a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Spironolacton%C4%83" title="Spironolactonă – Romanian" lang="ro" hreflang="ro" data-title="Spironolactonă" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target">Română</a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A1%D0%BF%D0%B8%D1%80%D0%BE%D0%BD%D0%BE%D0%BB%D0%B0%D0%BA%D1%82%D0%BE%D0%BD" title="Спиронолактон – Russian" lang="ru" hreflang="ru" data-title="Спиронолактон" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target">Русский</a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Spironolakton" title="Spironolakton – Serbian" lang="sr" hreflang="sr" data-title="Spironolakton" 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<button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Steroidal antiandrogen and antimineralocorticoid</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Spirolactone" title="Spirolactone">Spirolactone</a>.</div> <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">Spironolactone</caption><tbody><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><a href="/wiki/File:Spironolactone.svg" class="mw-file-description"><img alt="Skeletal formula of spironolactone" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/98/Spironolactone.svg/235px-Spironolactone.svg.png" decoding="async" width="235" height="199" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/98/Spironolactone.svg/353px-Spironolactone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/98/Spironolactone.svg/470px-Spironolactone.svg.png 2x" data-file-width="1290" data-file-height="1090" /></a></td></tr><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><a href="/wiki/File:Spironolactone_3D_ball.png" class="mw-file-description"><img alt="Ball-and-stick model of the spironolactone molecule" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Spironolactone_3D_ball.png/225px-Spironolactone_3D_ball.png" decoding="async" width="225" height="167" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Spironolactone_3D_ball.png/338px-Spironolactone_3D_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Spironolactone_3D_ball.png/450px-Spironolactone_3D_ball.png 2x" data-file-width="2000" data-file-height="1481" /></a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Pronunciation</th><td class="infobox-data"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/ˌspaɪroʊnoʊˈlæktoʊn/</a> <a href="/wiki/Help:Pronunciation_respelling_key" title="Help:Pronunciation respelling key">SPY-roh-noh-LAK-tone</a>,<a href="#cite_note-LoughlinGenerali2006-1">[1]</a> <a href="/wiki/Help:IPA/English" title="Help:IPA/English">/ˌspɪəroʊnoʊˈlæktoʊn/</a> <a href="/wiki/Help:Pronunciation_respelling_key" title="Help:Pronunciation respelling key">SPEER-oh-noh-LAK-tone</a><a href="#cite_note-ClarkHarvey2011-2">[2]</a> </td></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">Aldactone, others</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">SC-9420; NSC-150339; 7α-Acetylthiospirolactone; 7α-Acetylthio-17α-hydroxy-3-oxopregn-4-ene-21-carboxylic acid γ-lactone</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"><a rel="nofollow" class="external text" href="https://www.drugs.com/monograph/spironolactone.html">Monograph</a></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"><a rel="nofollow" class="external text" href="https://medlineplus.gov/druginfo/meds/a682627.html">a682627</a></td></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">License data</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><abbr class="country-name" title="United States">US</abbr> <a href="/wiki/DailyMed" title="DailyMed">DailyMed</a>: <a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=all&query=Spironolactone">Spironolactone</a></li></ul></div> </td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Pregnancy_category" title="Pregnancy category">Pregnancy category</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li><abbr class="country-name" title="Australia">AU</abbr>: B3<a href="#cite_note-Drugs.com_pregnancy-3">[3]</a></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 administration</a></th><td class="infobox-data"><a href="/wiki/Oral_administration" title="Oral administration">By mouth</a>,<a href="#cite_note-AHFS2015-4">[4]</a> <a href="/wiki/Topical_administration" class="mw-redirect" title="Topical administration">topical</a><a href="#cite_note-FARIDDiamanti-Kandarakis2009-5">[5]</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/Antimineralocorticoid" class="mw-redirect" title="Antimineralocorticoid">Antimineralocorticoid</a>; <a href="/wiki/Steroidal_antiandrogen" title="Steroidal antiandrogen">Steroidal antiandrogen</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_C03" title="ATC code C03">C03DA01</a> (<a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=C03DA01">WHO</a>) </li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li><abbr class="country-name" title="United Kingdom">UK</abbr>: <a href="/wiki/Prescription_drug" title="Prescription drug">POM</a> (Prescription only)<a href="#cite_note-7">[7]</a></li> <li><abbr class="country-name" title="United States">US</abbr>: <a href="/wiki/Boxed_warning" title="Boxed warning">WARNING</a><a href="#cite_note-FDA-AllBoxedWarnings-6">[6]</a>Rx-only<a href="#cite_note-Aldactone_label-8">[8]</a></li> <li><abbr class="country-name" title="European Union">EU</abbr>: Rx-only<a href="#cite_note-Qaialdo_EPAR-9">[9]</a><a href="#cite_note-10">[10]</a></li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a></th><td class="infobox-data">60–90%<a href="#cite_note-pmid15947888-11">[11]</a><a href="#cite_note-pmid18729003-12">[12]</a><a href="#cite_note-CaroneOxberry2017-13">[13]</a></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">Spironolactone: 88% (to <a href="/wiki/Human_serum_albumin" title="Human serum albumin">albumin</a> and <a href="/wiki/Alpha-1-acid_glycoprotein" class="mw-redirect" title="Alpha-1-acid glycoprotein"><abbr title="alpha-1-acid glycoprotein">AGP</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 alpha-1-acid glycoprotein)<a href="#cite_note-TakamuraMaruyama1997-14">[14]</a> Canrenone: 99.2% (to albumin)<a href="#cite_note-TakamuraMaruyama1997-14">[14]</a></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>, others: • <a href="/wiki/Deacetylation" class="mw-redirect" title="Deacetylation">Deacetylation</a> via <a href="/wiki/Carboxylesterase" title="Carboxylesterase"><abbr title="carboxylesterase">CES</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 carboxylesterase • S-<a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">Oxygenation</a> via <a href="/wiki/Flavin-containing_monooxygenase" title="Flavin-containing monooxygenase"><abbr title="flavin-containing monooxygenase">FOM</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 flavin-containing monooxygenase • S-<a href="/wiki/Methylation" title="Methylation">Methylation</a> via <a href="/wiki/Thiol_S-methyltransferase" title="Thiol S-methyltransferase"><abbr title="thiol S-methyltransferase">TMT</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 thiol S-methyltransferase • <a href="/wiki/Dethioacetylation" class="mw-redirect" title="Dethioacetylation">Dethioacetylation</a> • <a href="/wiki/Hydroxylation" title="Hydroxylation">Hydroxylation</a> via <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a> • <a href="/wiki/Lactone" title="Lactone">Lactone</a> <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a> via <a href="/wiki/PON3" title="PON3">PON3</a><a href="#cite_note-pmid15947888-11">[11]</a><a href="#cite_note-pmid18729003-12">[12]</a><a href="#cite_note-Parkinson2001-17">[17]</a><a href="#cite_note-Klaassen2007-18">[18]</a><a href="#cite_note-pmid7895608-19">[19]</a><a href="#cite_note-BlackElliott2006-20">[20]</a><a href="#cite_note-pmid14579013-21">[21]</a></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"><a href="/wiki/7%CE%B1-Thiospironolactone" title="7α-Thiospironolactone"><abbr title="7α-Thiospironolactone">7α-TS</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 7α-Thiospironolactone, <a href="/wiki/7%CE%B1-thiomethylspironolactone" class="mw-redirect" title="7α-thiomethylspironolactone"><abbr title="7α-thiomethylspironolactone">7α-TMS</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 7α-thiomethylspironolactone, <a href="/wiki/6%CE%B2-hydroxy-7%CE%B1-thiomethylspironolactone" class="mw-redirect" title="6β-hydroxy-7α-thiomethylspironolactone"><abbr title="6β-hydroxy-7α-thiomethylspironolactone">6β-OH-7α-TMS</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 6β-hydroxy-7α-thiomethylspironolactone, <a href="/wiki/Canrenone" title="Canrenone">canrenone</a>, others<a href="#cite_note-pmid15947888-11">[11]</a><a href="#cite_note-pmid18729003-12">[12]</a><a href="#cite_note-SzaszBudvari-Barany1990-15">[15]</a> (All three active)<a href="#cite_note-McDonaghGardner2011-16">[16]</a></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 half-life</a></th><td class="infobox-data">Spironolactone: 1.4 hrs<a href="#cite_note-pmid15947888-11">[11]</a> <a href="/wiki/7%CE%B1-thiomethylspironolactone" class="mw-redirect" title="7α-thiomethylspironolactone"><abbr title="7α-thiomethylspironolactone">7α-TMS</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 7α-thiomethylspironolactone: 13.8 hours<a href="#cite_note-pmid15947888-11">[11]</a> <a href="/wiki/6%CE%B2-hydroxy-7%CE%B1-thiomethylspironolactone" class="mw-redirect" title="6β-hydroxy-7α-thiomethylspironolactone"><abbr title="6β-hydroxy-7α-thiomethylspironolactone">6β-OH-7α-TMS</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 6β-hydroxy-7α-thiomethylspironolactone: 15.0 hrs<a href="#cite_note-pmid15947888-11">[11]</a> <a href="/wiki/Canrenone" title="Canrenone">Canrenone</a>: 16.5 hours<a href="#cite_note-pmid15947888-11">[11]</a></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/Bile" title="Bile">bile</a><a href="#cite_note-pmid18729003-12">[12]</a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">S-[(7R,8R,9S,10R,13S,14S,17R)-10,13-Dimethyl-3,5'-dioxospiro[2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17,2'-oxolane]-7-yl] ethanethioate</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><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=52-01-7">52-01-7</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/5833">5833</a></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><a rel="nofollow" class="external text" href="https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=2875">2875</a></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><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB00421">DB00421</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><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><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.5628.html">5628</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><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><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/27O7W4T232">27O7W4T232</a></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><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D00443">D00443</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><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><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9241">CHEBI:9241</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><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><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL1393">ChEMBL1393</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> (<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID6034186">DTXSID6034186</a> <a href="https://www.wikidata.org/wiki/Q422188#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard">ECHA InfoCard</a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.122">100.000.122</a> <a href="https://www.wikidata.org/wiki/Q422188#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data">C24H32O4S</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">416.58 g·mol−1</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><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC5O%5BC%40%40%5D4%28%5BC%40%40%5D3%28%5BC%40H%5D%28%5BC%40%40H%5D2%5BC%40H%5D%28SC%28%3DO%29C%29C%2FC1%3DC%2FC%28%3DO%29CC%5BC%40%5D1%28C%29%5BC%40H%5D2CC3%29CC4%29C%29CC5">Interactive image</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Melting_point" title="Melting point">Melting point</a></th><td class="infobox-data">134 to 135 °C (273 to 275 °F)</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%;">O=C5O[C@@]4([C@@]3([C@H]([C@@H]2[C@H](SC(=O)C)C/C1=C/C(=O)CC[C@]1(C)[C@H]2CC3)CC4)C)CC5</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/C24H32O4S/c1-14(25)29-19-13-15-12-16(26)4-8-22(15,2)17-5-9-23(3)18(21(17)19)6-10-24(23)11-7-20(27)28-24/h12,17-19,21H,4-11,13H2,1-3H3/t17-,18-,19+,21+,22-,23-,24+/m0/s1 <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</div></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:LXMSZDCAJNLERA-ZHYRCANASA-N <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</div></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>  <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=470470172&page2=Spironolactone">(verify)</a></td></tr></tbody></table> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Spironolacton_-_25_mg_%C3%BCberzogene_Tabletten_-_Verpackung_f%C3%BCr_Deutschland_-_Tabletten_mit_Verpackung.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5b/Spironolacton_-_25_mg_%C3%BCberzogene_Tabletten_-_Verpackung_f%C3%BCr_Deutschland_-_Tabletten_mit_Verpackung.jpg/220px-Spironolacton_-_25_mg_%C3%BCberzogene_Tabletten_-_Verpackung_f%C3%BCr_Deutschland_-_Tabletten_mit_Verpackung.jpg" decoding="async" width="220" height="111" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5b/Spironolacton_-_25_mg_%C3%BCberzogene_Tabletten_-_Verpackung_f%C3%BCr_Deutschland_-_Tabletten_mit_Verpackung.jpg/330px-Spironolacton_-_25_mg_%C3%BCberzogene_Tabletten_-_Verpackung_f%C3%BCr_Deutschland_-_Tabletten_mit_Verpackung.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5b/Spironolacton_-_25_mg_%C3%BCberzogene_Tabletten_-_Verpackung_f%C3%BCr_Deutschland_-_Tabletten_mit_Verpackung.jpg/440px-Spironolacton_-_25_mg_%C3%BCberzogene_Tabletten_-_Verpackung_f%C3%BCr_Deutschland_-_Tabletten_mit_Verpackung.jpg 2x" data-file-width="11776" data-file-height="5928" /></a><figcaption>Spironolactone 25 mg</figcaption></figure> Spironolactone, sold under the brand name Aldactone among others, is a <a href="/wiki/Diuretic" title="Diuretic">diuretic</a> <a href="/wiki/Medication" title="Medication">medication</a> primarily used to treat <a href="/wiki/Edema" title="Edema">fluid build-up</a> due to <a href="/wiki/Heart_failure" title="Heart failure">heart failure</a>, <a href="/wiki/Hepatic_cirrhosis" class="mw-redirect" title="Hepatic cirrhosis">liver scarring</a>, or <a href="/wiki/Kidney_disease" title="Kidney disease">kidney disease</a>.<a href="#cite_note-AHFS2015-4">[4]</a> It is also used in the treatment of <a href="/wiki/Hypertension" title="Hypertension">high blood pressure</a>, and <a href="/wiki/Hypokalemia" title="Hypokalemia">low blood potassium</a> that does not improve with <a href="/wiki/Potassium#Supplementation" title="Potassium">supplementation</a>, <a href="/wiki/Precocious_puberty" title="Precocious puberty">early puberty</a> in boys, <a href="/wiki/Acne" title="Acne">acne</a> and <a href="/wiki/Hirsutism" title="Hirsutism">excessive hair growth</a> in women.<a href="#cite_note-AHFS2015-4">[4]</a><a href="#cite_note-22">[22]</a><a href="#cite_note-23">[23]</a> Spironolactone is taken <a href="/wiki/Oral_administration" title="Oral administration">by mouth</a>.<a href="#cite_note-AHFS2015-4">[4]</a> Common <a href="/wiki/Side_effect" title="Side effect">side effects</a> include <a href="/wiki/Electrolyte_abnormalities" class="mw-redirect" title="Electrolyte abnormalities">electrolyte abnormalities</a>, particularly <a href="/wiki/Hyperkalemia" title="Hyperkalemia">high blood potassium</a>, nausea, vomiting, headache, rashes, and a decreased desire for sex.<a href="#cite_note-AHFS2015-4">[4]</a> In those with liver or kidney problems, extra care should be taken.<a href="#cite_note-AHFS2015-4">[4]</a> Spironolactone has not been well studied in pregnancy and should not be used to treat <a href="/wiki/High_blood_pressure_of_pregnancy" class="mw-redirect" title="High blood pressure of pregnancy">high blood pressure of pregnancy</a>.<a href="#cite_note-Drugs.com_pregnancy-3">[3]</a> It is also a <a href="/wiki/Steroid" title="Steroid">steroid</a> that <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">blocks</a> the effects of the <a href="/wiki/Hormone" title="Hormone">hormones</a> <a href="/wiki/Aldosterone" title="Aldosterone">aldosterone</a> and, to a lesser degree, <a href="/wiki/Testosterone" title="Testosterone">testosterone</a>, causing some <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogen</a>-like effects.<a href="#cite_note-Burinkul_2021-24">[24]</a>[<a href="/wiki/Wikipedia:Reliable_sources" title="Wikipedia:Reliable sources">unreliable source?</a>]<a href="#cite_note-Sehgal_2023-25">[25]</a><a href="#cite_note-ineffectiveness_in_HRT-26">[26]</a>[<a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)">unreliable medical source?</a>]<a href="#cite_note-AHFS2015-4">[4]</a><a href="#cite_note-Deedwania2014-27">[27]</a> Spironolactone belongs to a class of medications known as <a href="/wiki/Potassium-sparing_diuretic" title="Potassium-sparing diuretic">potassium-sparing diuretics</a>.<a href="#cite_note-AHFS2015-4">[4]</a> Spironolactone was discovered in 1957, and was introduced in 1959.<a href="#cite_note-OttowWeinmann2008-28">[28]</a><a href="#cite_note-Wermuth2008-29">[29]</a><a href="#cite_note-Sittig1988-30">[30]</a> It is on the <a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">World Health Organization's List of Essential Medicines</a>.<a href="#cite_note-WHO23rd-31">[31]</a> It is available as a <a href="/wiki/Generic_medication" class="mw-redirect" title="Generic medication">generic medication</a>.<a href="#cite_note-AHFS2015-4">[4]</a> In 2022, it was the 52nd most commonly prescribed medication in the United States, with more than 12 million prescriptions.<a href="#cite_note-32">[32]</a><a href="#cite_note-33">[33]</a> Spironolactone has a history of use in the trans community.<a href="#cite_note-34">[34]</a> Its use continues despite the rise of various accessible alternatives such as <a href="/wiki/Bicalutamide" title="Bicalutamide">bicalutamide</a> and <a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">cyproterone acetate</a> with more precise action and less side effects.<a href="#cite_note-Burinkul_2021-24">[24]</a><a href="#cite_note-Sehgal_2023-25">[25]</a> <style data-mw-deduplicate="TemplateStyles:r886046785">.mw-parser-output .toclimit-2 .toclevel-1 ul,.mw-parser-output .toclimit-3 .toclevel-2 ul,.mw-parser-output .toclimit-4 .toclevel-3 ul,.mw-parser-output .toclimit-5 .toclevel-4 ul,.mw-parser-output .toclimit-6 .toclevel-5 ul,.mw-parser-output .toclimit-7 .toclevel-6 ul{display:none}</style><div class="toclimit-3"><meta property="mw:PageProp/toc" /></div> <div class="mw-heading mw-heading2"><h2 id="Medical_uses">Medical uses</h2>[<a href="/w/index.php?title=Spironolactone&action=edit&section=1" title="Edit section: Medical uses">edit</a>]</div> Spironolactone is used primarily to treat <a href="/wiki/Heart_failure" title="Heart failure">heart failure</a>, <a href="/wiki/Edema" title="Edema">edematous</a> conditions such as <a href="/wiki/Nephrotic_syndrome" title="Nephrotic syndrome">nephrotic syndrome</a> or <a href="/wiki/Ascites" title="Ascites">ascites</a> in people with <a href="/wiki/Liver_disease" title="Liver disease">liver disease</a>, essential <a href="/wiki/Hypertension" title="Hypertension">hypertension</a>, <a href="/wiki/Hypokalemia" title="Hypokalemia">low blood levels of potassium</a>, <a href="/wiki/Secondary_hyperaldosteronism" class="mw-redirect" title="Secondary hyperaldosteronism">secondary hyperaldosteronism</a> (such as occurs with <a href="/wiki/Liver_cirrhosis" class="mw-redirect" title="Liver cirrhosis">liver cirrhosis</a>), and <a href="/wiki/Conn%27s_syndrome" class="mw-redirect" title="Conn's syndrome">Conn's syndrome</a> (primary hyperaldosteronism).[<a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)">medical citation needed</a>] The most common use of spironolactone is in the treatment of heart failure.<a href="#cite_note-RoncoBellomo2017-35">[35]</a> On its own, spironolactone is only a weak <a href="/wiki/Diuretic" title="Diuretic">diuretic</a> because it primarily targets the <a href="/wiki/Distal_nephron" class="mw-redirect" title="Distal nephron">distal nephron</a> (<a href="/wiki/Collecting_duct_system" title="Collecting duct system">collecting tubule</a>), where only small amounts of <a href="/wiki/Sodium" title="Sodium">sodium</a> are reabsorbed, but it can be combined with other diuretics to increase efficacy.[<a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)">medical citation needed</a>] The classification of spironolactone as a "potassium-sparing diuretic" has been described as obsolete.<a href="#cite_note-pmid10760075-36">[36]</a> Spironolactone is also used to treat <a href="/wiki/Bartter%27s_syndrome" class="mw-redirect" title="Bartter's syndrome">Bartter's syndrome</a> due to its ability to raise potassium levels.<a href="#cite_note-EndouHosoyamada1995-37">[37]</a> Spironolactone has antiandrogenic activity. For this reason, it is used to treat a variety of <a href="/wiki/Dermatological_condition" class="mw-redirect" title="Dermatological condition">dermatological conditions</a> in which androgens play a role. Some of these uses include <a href="/wiki/Acne" title="Acne">acne</a>, <a href="/wiki/Seborrhea" class="mw-redirect" title="Seborrhea">seborrhea</a>, <a href="/wiki/Hirsutism" title="Hirsutism">hirsutism</a>, and <a href="/wiki/Pattern_hair_loss" title="Pattern hair loss">pattern hair loss</a> in women.<a href="#cite_note-pmid2969259-38">[38]</a> Spironolactone is used for the treatment of hirsutism in the United States.<a href="#cite_note-Preedy2012-39">[39]</a> High doses of spironolactone, which are needed for considerable antiandrogenic effects, are not recommended for men due to the high risk of <a href="/wiki/Feminization_(biology)" title="Feminization (biology)">feminization</a> and other side effects. Spironolactone can be used to treat <a href="/wiki/Symptom" class="mw-redirect" title="Symptom">symptoms</a> of <a href="/wiki/Hyperandrogenism" title="Hyperandrogenism">hyperandrogenism</a>, such as due to <a href="/wiki/Polycystic_ovary_syndrome" title="Polycystic ovary syndrome">polycystic ovary syndrome</a>.<a href="#cite_note-pmid3143568-40">[40]</a> <div class="mw-heading mw-heading3"><h3 id="Heart_failure">Heart failure</h3>[<a href="/w/index.php?title=Spironolactone&action=edit&section=2" title="Edit section: Heart failure">edit</a>]</div> While <a href="/wiki/Loop_diuretics" class="mw-redirect" title="Loop diuretics">loop diuretics</a> remain first-line for most people with <a href="/wiki/Heart_failure" title="Heart failure">heart failure</a>, spironolactone has shown to reduce both morbidity and mortality in numerous studies and remains an important agent for treating fluid retention, edema, and symptoms of heart failure. Current recommendations from the <a href="/wiki/American_Heart_Association" title="American Heart Association">American Heart Association</a> are to use spironolactone in patients with NYHA Class II-IV heart failure who have a left ventricular <a href="/wiki/Ejection_fraction" title="Ejection fraction">ejection fraction</a> of less than 35%.<a href="#cite_note-Yancy_e147-239-41">[41]</a> Spironolactone improves left ventricular <a href="/wiki/Diastolic_function" title="Diastolic function">diastolic function</a> in patients with <a href="/wiki/Heart_failure_with_preserved_ejection_fraction" title="Heart failure with preserved ejection fraction">heart failure with preserved ejection fraction</a>, however it has no effect on mortality and hospitalization.<a href="#cite_note-Li_2018-42">[42]</a><a href="#cite_note-Kosmas_2018-43">[43]</a> Due to its antiandrogenic properties, spironolactone can cause effects associated with low androgen levels and <a href="/wiki/Hypogonadism" title="Hypogonadism">hypogonadism</a> in males. For this reason, men are typically not prescribed spironolactone for any longer than a short period of time, e.g., for an acute exacerbation of heart failure. A newer medication, <a href="/wiki/Eplerenone" title="Eplerenone">eplerenone</a>, has been approved by the US <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> (FDA) for the treatment of heart failure, and lacks the antiandrogenic effects of spironolactone. As such, it is far more suitable for men for whom long-term medication is being chosen. However, eplerenone may not be as effective as spironolactone or the related medication <a href="/wiki/Canrenone" title="Canrenone">canrenone</a> in reducing mortality from heart failure.<a href="#cite_note-pmid22840667-44">[44]</a> <div class="mw-heading mw-heading3"><h3 id="High_blood_pressure">High blood pressure</h3>[<a href="/w/index.php?title=Spironolactone&action=edit&section=3" title="Edit section: High blood pressure">edit</a>]</div> About 1 in 100 people with hypertension have elevated levels of aldosterone; in these people, the antihypertensive effect of spironolactone may exceed that of complex combined regimens of other antihypertensives since it targets the primary cause of the elevated blood pressure. However, a <a href="/wiki/Cochrane_review" class="mw-redirect" title="Cochrane review">Cochrane review</a> found adverse effects at high doses and little effect on blood pressure at low doses in the majority of people with high blood pressure.<a href="#cite_note-Bat2010-45">[45]</a> There is no evidence of person-oriented outcome at any dose in this group.<a href="#cite_note-Bat2010-45">[45]</a> <div class="mw-heading mw-heading3"><h3 id="High_aldosterone_levels">High aldosterone levels</h3>[<a href="/w/index.php?title=Spironolactone&action=edit&section=4" title="Edit section: High aldosterone levels">edit</a>]</div> Spironolactone is used in the treatment of <a href="/wiki/Hyperaldosteronism" title="Hyperaldosteronism">hyperaldosteronism</a> (high aldosterone levels or mineralocorticoid excess), for instance <a href="/wiki/Primary_aldosteronism" title="Primary aldosteronism">primary aldosteronism</a> (Conn's syndrome).<a href="#cite_note-pmid30854950-46">[46]</a> Antimineralocorticoids like spironolactone and <a href="/wiki/Eplerenone" title="Eplerenone">eplerenone</a> are <a href="/wiki/First-line_treatment" class="mw-redirect" title="First-line treatment">first-line treatments</a> for hyperaldosteronism.<a href="#cite_note-pmid30854950-46">[46]</a> They improve blood pressure and potassium levels, as well as <a href="/wiki/Left_ventricular_hypertrophy" title="Left ventricular hypertrophy">left ventricular hypertrophy</a>, <a href="/wiki/Albuminuria" title="Albuminuria">albuminuria</a>, and <a href="/wiki/Carotid_intima-media_thickness" class="mw-redirect" title="Carotid intima-media thickness">carotid intima-media thickness</a>, in people with primary aldosteronism.<a href="#cite_note-pmid30854950-46">[46]</a> In people with hyperaldosteronism due to unilateral aldosterone-producing <a href="/wiki/Adrenocortical_adenoma" title="Adrenocortical adenoma">adrenocortical adenoma</a>, <a href="/wiki/Adrenalectomy" title="Adrenalectomy">adrenalectomy</a> should be preferred instead of antimineralocorticoids.<a href="#cite_note-pmid30854950-46">[46]</a> Spironolactone should not be used to treat primary aldosteronism in pregnancy due to its antiandrogen-related risk of <a href="/wiki/Teratogen" class="mw-redirect" title="Teratogen">teratogenicity</a> in male fetuses.<a href="#cite_note-pmid35536535-47">[47]</a><a href="#cite_note-pmid27156905-48">[48]</a><a href="#cite_note-pmid25163723-49">[49]</a><a href="#cite_note-pmid32586668-50">[50]</a> <div class="mw-heading mw-heading3"><h3 id="Skin_and_hair_conditions">Skin and hair conditions</h3>[<a href="/w/index.php?title=Spironolactone&action=edit&section=5" title="Edit section: Skin and hair conditions">edit</a>]</div> Androgens like testosterone and DHT play a critical role in the <a href="/wiki/Pathogenesis" title="Pathogenesis">pathogenesis</a> of a number of <a href="/wiki/Cutaneous_condition" class="mw-redirect" title="Cutaneous condition">dermatological conditions</a> including <a href="/wiki/Oily_skin" class="mw-redirect" title="Oily skin">oily skin</a>, <a href="/wiki/Acne" title="Acne">acne</a>, <a href="/wiki/Seborrhea" class="mw-redirect" title="Seborrhea">seborrhea</a>, <a href="/wiki/Hirsutism" title="Hirsutism">hirsutism</a> (excessive facial/body hair growth in women), and <a href="/wiki/Male_pattern_hair_loss" class="mw-redirect" title="Male pattern hair loss">male pattern hair loss</a> (androgenic alopecia).<a href="#cite_note-pmid15507105-51">[51]</a><a href="#cite_note-pmid28979664-52">[52]</a> In demonstration of this, women with <a href="/wiki/Complete_androgen_insensitivity_syndrome" title="Complete androgen insensitivity syndrome">complete androgen insensitivity syndrome</a> (CAIS) do not produce <a href="/wiki/Sebum" class="mw-redirect" title="Sebum">sebum</a> or develop acne and have little to no <a href="/wiki/Body_hair" title="Body hair">body</a>, <a href="/wiki/Pubic_hair" title="Pubic hair">pubic</a>, or <a href="/wiki/Axillary_hair" class="mw-redirect" title="Axillary hair">axillary hair</a>.<a href="#cite_note-ShalitaRosso2011-53">[53]</a><a href="#cite_note-ZouboulisKatsambas2014-54">[54]</a> Moreover, men with <a href="/wiki/Congenital_disorder" class="mw-redirect" title="Congenital disorder">congenital</a> <a href="/wiki/5%CE%B1-reductase_deficiency" class="mw-redirect" title="5α-reductase deficiency">5α-reductase type II deficiency</a>, <a href="/wiki/5%CE%B1-reductase" class="mw-redirect" title="5α-reductase">5α-reductase</a> being an <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> that greatly potentiates the androgenic effects of testosterone in the skin, have little to no acne, scanty <a href="/wiki/Facial_hair" title="Facial hair">facial hair</a>, reduced body hair, and reportedly no incidence of male-pattern hair loss.<a href="#cite_note-pmid16985920-55">[55]</a><a href="#cite_note-Sloane2002-56">[56]</a><a href="#cite_note-HannoGuzzo2014-57">[57]</a><a href="#cite_note-Harper2007-58">[58]</a><a href="#cite_note-Blume-PeytaviWhiting2008-59">[59]</a> Conversely, <a href="/wiki/Hyperandrogenism" title="Hyperandrogenism">hyperandrogenism</a> in women, for instance due to <a href="/wiki/Polycystic_ovary_syndrome" title="Polycystic ovary syndrome">polycystic ovary syndrome</a> (PCOS) or <a href="/wiki/Congenital_adrenal_hyperplasia" title="Congenital adrenal hyperplasia">congenital adrenal hyperplasia</a> (CAH), is commonly associated with acne and hirsutism as well as <a href="/wiki/Virilization" title="Virilization">virilization</a> (masculinization) in general.<a href="#cite_note-pmid15507105-51">[51]</a> In accordance with the preceding, <a href="/wiki/Antiandrogen" title="Antiandrogen">antiandrogens</a> are highly effective in the treatment of the aforementioned <a href="/wiki/Androgen-dependent_condition" title="Androgen-dependent condition">androgen-dependent</a> skin and hair conditions.<a href="#cite_note-pmid9420861-60">[60]</a><a href="#cite_note-pmid20082945-61">[61]</a> Because of the antiandrogenic activity of spironolactone, it can be quite effective in treating acne in women.<a href="#cite_note-pmid22468178-62">[62]</a><a href="#cite_note-pmid28155090-63">[63]</a><a href="#cite_note-64">[64]</a> In addition, spironolactone reduces oil that is naturally produced in the skin and can be used to treat oily skin.<a href="#cite_note-pmid28155090-63">[63]</a><a href="#cite_note-pmid26897386-65">[65]</a><a href="#cite_note-pmid28979664-52">[52]</a> Though not the primary intended purpose of the medication, the ability of spironolactone to be helpful with problematic skin and acne conditions was discovered to be one of the beneficial side effects and has been quite successful.<a href="#cite_note-pmid28155090-63">[63]</a><a href="#cite_note-pmid26897386-65">[65]</a> Oftentimes, for women treating acne, spironolactone is prescribed and paired with a <a href="/wiki/Combined_oral_contraceptive_pill" title="Combined oral contraceptive pill">birth control pill</a>.<a href="#cite_note-pmid28155090-63">[63]</a><a href="#cite_note-pmid26897386-65">[65]</a> Positive results in the pairing of these two medications have been observed, although these results may not be seen for up to three months.<a href="#cite_note-pmid28155090-63">[63]</a><a href="#cite_note-pmid26897386-65">[65]</a> Spironolactone has been reported to produce a 50 to 100% improvement in acne at sufficiently high doses.<a href="#cite_note-pmid9238337-66">[66]</a> Response to treatment generally requires 1 to 3 months in the case of acne and up to 6 months in the case of hirsutism.<a href="#cite_note-pmid9238337-66">[66]</a> Ongoing therapy is generally required to avoid relapse of symptoms.<a href="#cite_note-pmid9238337-66">[66]</a> Spironolactone is commonly used in the treatment of hirsutism in women, and is considered to be a first-line antiandrogen for this indication.<a href="#cite_note-pmid24889738-67">[67]</a> Spironolactone can be used in the treatment of <a href="/wiki/Female-pattern_hair_loss" class="mw-redirect" title="Female-pattern hair loss">female-pattern hair loss</a> (pattern scalp hair loss in women).<a href="#cite_note-pmid21413648-68">[68]</a> There is tentative low quality evidence supporting its use for this indication.<a href="#cite_note-69">[69]</a> Although apparently effective, not all cases of female-pattern hair loss are dependent on androgens.<a href="#cite_note-pmid20128792-70">[70]</a> Antiandrogens like spironolactone are male-specific <a href="/wiki/Teratogen" class="mw-redirect" title="Teratogen">teratogens</a> which can feminize male <a href="/wiki/Fetus" title="Fetus">fetuses</a> due to their antiandrogenic effects.<a href="#cite_note-pmid9420861-60">[60]</a><a href="#cite_note-IswaranImai1997-71">[71]</a><a href="#cite_note-Smith2013-72">[72]</a> For this reason, it is recommended that antiandrogens only be used to treat women who are of reproductive age in conjunction with adequate contraception.<a href="#cite_note-pmid9420861-60">[60]</a><a href="#cite_note-IswaranImai1997-71">[71]</a><a href="#cite_note-Smith2013-72">[72]</a> Oral contraceptives, which contain an <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogen</a> and a <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestin</a>, are typically used for this purpose.<a href="#cite_note-pmid9420861-60">[60]</a> Moreover, oral contraceptives themselves are functional antiandrogens and are independently effective in the treatment of androgen-dependent skin and hair conditions, and hence can significantly augment the effectiveness of antiandrogens in the treatment of such conditions.<a href="#cite_note-pmid9420861-60">[60]</a><a href="#cite_note-Ostrzenski2002-73">[73]</a> Spironolactone is not generally used in men for the treatment of androgen-dependent dermatological conditions because of its feminizing side effects, but it is effective for such indications in men similarly.<a href="#cite_note-pmid21413648-68">[68]</a> As an example, spironolactone has been reported to reduce symptoms of acne in males.<a href="#cite_note-pmid9557251-74">[74]</a> An additional example is the usefulness of spironolactone as an antiandrogen in transgender women.<a href="#cite_note-WPATH2011-75">[75]</a><a href="#cite_note-pmid19509099-76">[76]</a><a href="#cite_note-pmid2540730-77">[77]</a> <a href="/wiki/Topical_medication" title="Topical medication">Topical</a> spironolactone has been found to be effective in the treatment of acne as well.<a href="#cite_note-pmid1387779-78">[78]</a> As a result, topical pharmaceutical formulations containing 2% or 5% spironolactone cream became available in Italy for the treatment of acne and hirsutism in the early 1990s.<a href="#cite_note-pmid8112074-79">[79]</a><a href="#cite_note-Benvenga2009-80">[80]</a> The products were discontinued in 2006 when the creams were added to the list of doping substances with a decree of the <a href="/wiki/Ministry_of_Health_(Italy)" title="Ministry of Health (Italy)">Ministry of Health</a> that year.<a href="#cite_note-Benvenga2009-80">[80]</a> <div class="mw-heading mw-heading4"><h4 id="Comparison">Comparison</h4>[<a href="/w/index.php?title=Spironolactone&action=edit&section=6" title="Edit section: Comparison">edit</a>]</div> Spironolactone, the <a href="/wiki/5%CE%B1-reductase_inhibitor" class="mw-redirect" title="5α-reductase inhibitor">5α-reductase inhibitor</a> <a href="/wiki/Finasteride" title="Finasteride">finasteride</a>, and the <a href="/wiki/Nonsteroidal_antiandrogen" title="Nonsteroidal antiandrogen">nonsteroidal antiandrogen</a> <a href="/wiki/Flutamide" title="Flutamide">flutamide</a> all appear to have similar effectiveness in the treatment of hirsutism.<a href="#cite_note-pmid24889738-67">[67]</a><a href="#cite_note-pmid25918921-81">[81]</a><a href="#cite_note-pmid29522176-82">[82]</a> However, some clinical research has found that the effectiveness of spironolactone for hirsutism is greater than that of finasteride but is less than that of flutamide.<a href="#cite_note-pmid24889738-67">[67]</a> The combination of spironolactone with finasteride is more effective than either alone for hirsutism and the combination of spironolactone with a birth control pill is more effective than a birth control pill alone.<a href="#cite_note-pmid24889738-67">[67]</a> One study showed that spironolactone or the <a href="/wiki/Steroidal_antiandrogen" title="Steroidal antiandrogen">steroidal antiandrogen</a> <a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">cyproterone acetate</a> both in combination with a birth control pill had equivalent effectiveness for hirsutism.<a href="#cite_note-pmid24889738-67">[67]</a> Spironolactone is considered to be a first-line treatment for hirsutism, finasteride and the steroidal antiandrogen cyproterone acetate are considered to be second-line treatments, and flutamide is no longer recommended for hirsutism due to <a href="/wiki/Liver_toxicity" class="mw-redirect" title="Liver toxicity">liver toxicity</a> concerns.<a href="#cite_note-pmid24889738-67">[67]</a> The nonsteroidal antiandrogen <a href="/wiki/Bicalutamide" title="Bicalutamide">bicalutamide</a> is an alternative option to flutamide with improved <a href="/wiki/Drug_safety" class="mw-redirect" title="Drug safety">safety</a>.<a href="#cite_note-pmid24455796-83">[83]</a><a href="#cite_note-pmid29211888-84">[84]</a> The combination of spironolactone with a birth control pill in the treatment of acne appears to have similar effectiveness to a birth control pill alone and the combination of a birth control pill with cyproterone acetate, flutamide, or finasteride.<a href="#cite_note-pmid28155090-63">[63]</a> However, this was based on low- to very-low-quality evidence.<a href="#cite_note-pmid28155090-63">[63]</a> Spironolactone may be more effective than birth control pills in the treatment of acne, and the combination of spironolactone with a birth control pill may have greater effectiveness for acne than either alone.<a href="#cite_note-pmid22994662-85">[85]</a> In addition, some clinical research has found that flutamide is more effective than spironolactone in the treatment of acne.<a href="#cite_note-pmid28155090-63">[63]</a> In one study, flutamide decreased acne scores by 80% within 3 months, whereas spironolactone decreased symptoms by only 40% in the same time period.<a href="#cite_note-pmid10495361-86">[86]</a><a href="#cite_note-ShelleyShelley2001-87">[87]</a><a href="#cite_note-BalenFranks2010-88">[88]</a> However, the use of flutamide for acne is limited by its liver toxicity.<a href="#cite_note-pmid28379593-89">[89]</a><a href="#cite_note-pmid28492054-90">[90]</a><a href="#cite_note-YasaDural2016-91">[91]</a><a href="#cite_note-pmid28274354-92">[92]</a> Bicalutamide is a potential alternative to flutamide for acne as well.<a href="#cite_note-pmid27416311-93">[93]</a><a href="#cite_note-pmid30312645-94">[94]</a> Spironolactone can be considered as a first-line treatment for acne in those who have failed other standard treatments such as topical therapies and under certain other circumstances, although this is controversial due to the side effects of spironolactone and its <a href="/wiki/Teratogenicity" class="mw-redirect" title="Teratogenicity">teratogenicity</a>.<a href="#cite_note-pmid22994662-85">[85]</a><a href="#cite_note-pmid20082945-61">[61]</a> There is insufficient clinical evidence to compare the effectiveness of spironolactone with other antiandrogens for female-pattern hair loss.<a href="#cite_note-pmid27225981-95">[95]</a> The effectiveness of spironolactone in the treatment of both acne and hirsutism appears to be dose-dependent, with higher doses being more effective than lower doses.<a href="#cite_note-pmid22994662-85">[85]</a><a href="#cite_note-pmid19370553-96">[96]</a><a href="#cite_note-Hammerstein1990-97">[97]</a> However, higher doses also have greater side effects, such as <a href="/wiki/Menstrual_irregularities" class="mw-redirect" title="Menstrual irregularities">menstrual irregularities</a>.<a href="#cite_note-pmid28155090-63">[63]</a> <div class="mw-heading mw-heading3"><h3 id="Transgender_hormone_therapy">Transgender hormone therapy</h3>[<a href="/w/index.php?title=Spironolactone&action=edit&section=7" title="Edit section: Transgender hormone therapy">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Feminizing_hormone_therapy#Steroidal_antiandrogens" title="Feminizing hormone therapy">Feminizing hormone therapy § Steroidal antiandrogens</a></div> Despite <a href="/wiki/Paradoxical_reaction" title="Paradoxical reaction">paradoxical reactions</a>, spironolactone is used <a href="/wiki/Off-label_use" title="Off-label use">off-label</a> as a component of <a href="/wiki/Feminizing_hormone_therapy" title="Feminizing hormone therapy">feminizing hormone therapy</a> in <a href="/wiki/Transgender_women" class="mw-redirect" title="Transgender women">transgender women</a>, especially in the United States (where <a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">cyproterone acetate</a> is not available), usually in addition to an <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogen</a>.<a href="#cite_note-Paradoxical_reactions-98">[98]</a>[<a href="/wiki/Wikipedia:Reliable_sources" title="Wikipedia:Reliable sources">unreliable source?</a>]<a href="#cite_note-WPATH2011-75">[75]</a><a href="#cite_note-pmid19509099-76">[76]</a><a href="#cite_note-pmid2540730-77">[77]</a> Alternatives like <a href="/wiki/Bicalutamide" title="Bicalutamide">bicalutamide</a> do not have a similar level of popularity.<a href="#cite_note-99">[99]</a> As spironolactone's antiandrogenic effect appears only in high doses, it can have a wide array of side effects not found in antiandrogens working more exclusively on the androgen receptor.<a href="#cite_note-Burinkul_2021-24">[24]</a><a href="#cite_note-Sehgal_2023-25">[25]</a><a href="#cite_note-ineffectiveness_in_HRT-26">[26]</a>[<a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)">unreliable medical source?</a>] When coupled with estradiol, effects in transgender women include decreased <a href="/wiki/Hirsutism" title="Hirsutism">male pattern body hair</a>, induction of <a href="/wiki/Breast_development" title="Breast development">breast development</a> and of <a href="/wiki/Feminization_(biology)" title="Feminization (biology)">feminization</a> in general, and reduced <a href="/wiki/Spontaneous_erection" class="mw-redirect" title="Spontaneous erection">spontaneous erections</a>.<a href="#cite_note-pmid2540730-77">[77]</a> <div class="mw-heading mw-heading3"><h3 id="Forms">Forms</h3>[<a href="/w/index.php?title=Spironolactone&action=edit&section=8" title="Edit section: Forms">edit</a>]</div> Spironolactone is available in the form of <a href="/wiki/Tablet_(pharmacy)" title="Tablet (pharmacy)">tablets</a> (25 mg, 50 mg, 100 mg; brand name Aldactone, others) and <a href="/wiki/Suspension_(chemistry)" title="Suspension (chemistry)">suspensions</a> (25 mg/5 mL; brand name Carospir) for use <a href="/wiki/Oral_administration" title="Oral administration">by mouth</a>.<a href="#cite_note-Muller1998-100">[100]</a><a href="#cite_note-LeeDesai2007-101">[101]</a><a href="#cite_note-Niazi2016-102">[102]</a><a href="#cite_note-WakelinMaibach2002-103">[103]</a><a href="#cite_note-Drugs@FDA-104">[104]</a>[<a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">failed verification</a>] It has also been marketed in the form of 2% and 5% <a href="/wiki/Topical" class="mw-redirect" title="Topical">topical</a> <a href="/wiki/Cream" title="Cream">cream</a> in Italy for the treatment of <a href="/wiki/Acne" title="Acne">acne</a> and <a href="/wiki/Hirsutism" title="Hirsutism">hirsutism</a> under the brand name Spiroderm, but this product is no longer available.<a href="#cite_note-FARIDDiamanti-Kandarakis2009-5">[5]</a><a href="#cite_note-IndexNominum2000-105">[105]</a> The medication is also available in combination with other medications, such as <a href="/wiki/Hydrochlorothiazide" title="Hydrochlorothiazide">hydrochlorothiazide</a> (brand name Aldactazide, others).<a href="#cite_note-Drugs@FDA-104">[104]</a>[<a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">failed verification</a>]<a href="#cite_note-Drugs.com-106">[106]</a> Spironolactone has poor <a href="/wiki/Water_solubility" class="mw-redirect" title="Water solubility">water solubility</a>, and for this reason, only oral and topical formulations have been developed; other <a href="/wiki/Routes_of_administration" class="mw-redirect" title="Routes of administration">routes of administration</a> such as <a href="/wiki/Intravenous_administration" class="mw-redirect" title="Intravenous administration">intravenous injection</a> are not used.<a href="#cite_note-pmid15947888-11">[11]</a> The only antimineralocorticoid that is available as a <a href="/wiki/Solution_(chemistry)" title="Solution (chemistry)">solution</a> for <a href="/wiki/Parenteral" class="mw-redirect" title="Parenteral">parenteral</a> use is the related medication <a href="/wiki/Potassium_canrenoate" title="Potassium canrenoate">potassium canrenoate</a>.<a href="#cite_note-pmid28634268-107">[107]</a> <div class="mw-heading mw-heading2"><h2 id="Contraindications">Contraindications</h2>[<a href="/w/index.php?title=Spironolactone&action=edit&section=9" title="Edit section: Contraindications">edit</a>]</div> <a href="/wiki/Contraindication" title="Contraindication">Contraindications</a> of spironolactone include <a href="/wiki/Hyperkalemia" title="Hyperkalemia">hyperkalemia</a> (high potassium levels), <a href="/wiki/End-stage_kidney_disease" class="mw-redirect" title="End-stage kidney disease">severe and end-stage kidney disease</a> (due to high hyperkalemia risk, except possibly in those on <a href="/wiki/Kidney_dialysis" title="Kidney dialysis">dialysis</a>), <a href="/wiki/Addison%27s_disease" title="Addison's disease">Addison's disease</a> (adrenal insufficiency and low aldosterone levels), and concomitant use of <a href="/wiki/Eplerenone" title="Eplerenone">eplerenone</a>.<a href="#cite_note-Aldactone_label-8">[8]</a><a href="#cite_note-GoldsmithCovic2014-108">[108]</a> It should also be used with caution in people with certain <a href="/wiki/Neurological_disorder" title="Neurological disorder">neurological disorders</a>, as well as those who experience or have experienced <a href="/wiki/Anuria" title="Anuria">anuria</a> (lack of urine production), <a href="/wiki/Acute_kidney_injury" title="Acute kidney injury">acute kidney injury</a>, or <a href="/wiki/Kidney_failure" title="Kidney failure">significant impairment of kidney excretory function</a> with risk of hyperkalemia.<a href="#cite_note-Aldactone_label-8">[8]</a> <div class="mw-heading mw-heading2"><h2 id="Side_effects">Side effects</h2>[<a href="/w/index.php?title=Spironolactone&action=edit&section=10" title="Edit section: Side effects">edit</a>]</div> One of the most common side effects of spironolactone is <a href="/wiki/Frequent_urination" title="Frequent urination">frequent urination</a>. Other general side effects include <a href="/wiki/Dehydration" title="Dehydration">dehydration</a>, <a href="/wiki/Hyponatremia" title="Hyponatremia">hyponatremia</a> (low <a href="/wiki/Sodium" title="Sodium">sodium</a> levels), mild <a href="/wiki/Hypotension" title="Hypotension">hypotension</a> (low <a href="/wiki/Blood_pressure" title="Blood pressure">blood pressure</a>),<a href="#cite_note-pmid10495361-86">[86]</a> <a href="/wiki/Ataxia" title="Ataxia">ataxia</a> (muscle incoordination), <a href="/wiki/Drowsiness" class="mw-redirect" title="Drowsiness">drowsiness</a>, <a href="/wiki/Dizziness" title="Dizziness">dizziness</a>,<a href="#cite_note-pmid10495361-86">[86]</a> <a href="/wiki/Dry_skin" class="mw-redirect" title="Dry skin">dry skin</a>, and <a href="/wiki/Rash" title="Rash">rashes</a>. Because of its antiandrogenic activity, spironolactone can, in men, cause <a href="/wiki/Breast_tenderness" class="mw-redirect" title="Breast tenderness">breast tenderness</a>, <a href="/wiki/Gynecomastia" title="Gynecomastia">gynecomastia</a> (breast development), <a href="/wiki/Feminization_(biology)" title="Feminization (biology)">feminization</a> in general, and <a href="/wiki/Demasculinization" class="mw-redirect" title="Demasculinization">demasculinization</a>, as well as <a href="/wiki/Sexual_dysfunction" title="Sexual dysfunction">sexual dysfunction</a> including <a href="/wiki/Loss_of_libido" class="mw-redirect" title="Loss of libido">loss of libido</a> and <a href="/wiki/Erectile_dysfunction" title="Erectile dysfunction">erectile dysfunction</a>, although these side effects are usually confined to high doses of spironolactone.<a href="#cite_note-pmid984618-109">[109]</a> At very high doses (400 mg/day), spironolactone has also been associated with <a href="/wiki/Testicular_atrophy" title="Testicular atrophy">testicular atrophy</a> and reversibly <a href="/wiki/Infertility" title="Infertility">reduced fertility</a>, including <a href="/wiki/Semen_abnormalities" class="mw-redirect" title="Semen abnormalities">semen abnormalities</a> such as decreased <a href="/wiki/Sperm_count" class="mw-redirect" title="Sperm count">sperm count</a> and <a href="/wiki/Sperm_motility" title="Sperm motility">motility</a> in men.<a href="#cite_note-SeldinGiebisch1997-110">[110]</a><a href="#cite_note-Aronson2009-111">[111]</a> However, such doses of spironolactone are rarely used clinically.<a href="#cite_note-Aronson2009-111">[111]</a> In women, spironolactone can cause <a href="/wiki/Menstrual_irregularities" class="mw-redirect" title="Menstrual irregularities">menstrual irregularities</a>, <a href="/wiki/Breast_tenderness" class="mw-redirect" title="Breast tenderness">breast tenderness</a>, and <a href="/wiki/Mammoplasia" title="Mammoplasia">breast enlargement</a>.<a href="#cite_note-pmid2969259-38">[38]</a><a href="#cite_note-pmid28155090-63">[63]</a><a href="#cite_note-CarrellPeterson2010-112">[112]</a> Aside from these adverse effects, the side effects of spironolactone in women taking high doses are minimal, and it is well tolerated.<a href="#cite_note-pmid28155090-63">[63]</a><a href="#cite_note-pmid10495361-86">[86]</a><a href="#cite_note-PescovitzEugster2004-113">[113]</a> A potential side effect of spironolactone is <a href="/wiki/Hyperkalemia" title="Hyperkalemia">hyperkalemia</a> (high <a href="/wiki/Potassium" title="Potassium">potassium</a> levels), which, in severe cases, can be life-threatening.<a href="#cite_note-Aldactone_label-8">[8]</a> Hyperkalemia can present as a normal anion-gap metabolic acidosis.<a href="#cite_note-Aldactone_label-8">[8]</a> It has been reported that the addition of spironolactone to loop diuretics in people with heart failure was associated with a higher risk of hyperkalemia and <a href="/wiki/Acute_kidney_injury" title="Acute kidney injury">acute kidney injury</a>.<a href="#cite_note-114">[114]</a> Spironolactone may put people at a heightened risk for gastrointestinal issues like nausea, vomiting, diarrhea, cramping, and <a href="/wiki/Gastritis" title="Gastritis">gastritis</a>.<a href="#cite_note-Aldactone_label-8">[8]</a><a href="#cite_note-115">[115]</a> In addition, there has been some evidence suggesting an association between use of the medication and <a href="/wiki/Hemorrhage" class="mw-redirect" title="Hemorrhage">bleeding</a> from the <a href="/wiki/Stomach" title="Stomach">stomach</a> and <a href="/wiki/Duodenum" title="Duodenum">duodenum</a>,<a href="#cite_note-Aldactone_label-8">[8]</a> though a causal relationship between the two has not been established.<a href="#cite_note-116">[116]</a><a href="#cite_note-pmid18507655-117">[117]</a> Also, spironolactone is <a href="/wiki/Immunosuppression" title="Immunosuppression">immunosuppressive</a> in the treatment of <a href="/wiki/Sarcoidosis" title="Sarcoidosis">sarcoidosis</a>.<a href="#cite_note-118">[118]</a> Most of the side effects of spironolactone are dose-dependent.<a href="#cite_note-pmid22468178-62">[62]</a> Low-dose spironolactone is generally very well tolerated.<a href="#cite_note-pmid22468178-62">[62]</a> Even higher doses of spironolactone, such as 100 mg/day, are well tolerated in most individuals.<a href="#cite_note-pmid22468178-62">[62]</a> Dose-dependent side effects of spironolactone include menstrual irregularities, breast tenderness and enlargement, <a href="/wiki/Orthostatic_hypotension" title="Orthostatic hypotension">orthostatic hypotension</a>, and hyperkalemia.<a href="#cite_note-pmid22468178-62">[62]</a> The side effects of spironolactone are usually mild and rarely result in discontinuation.<a href="#cite_note-pmid22468178-62">[62]</a> <table class="wikitable sortable mw-collapsible mw-collapsed" width="750px" style="margin-left: auto; margin-right: auto; border: none;"> <caption class="nowrap"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul ul{display:inline}.mw-parser-output .hlist .mw-empty-li{display:none}.mw-parser-output .hlist dt::after{content:": "}.mw-parser-output .hlist dd::after,.mw-parser-output .hlist li::after{content:" · ";font-weight:bold}.mw-parser-output .hlist dd:last-child::after,.mw-parser-output .hlist dt:last-child::after,.mw-parser-output .hlist li:last-child::after{content:none}.mw-parser-output .hlist dd dd:first-child::before,.mw-parser-output .hlist dd dt:first-child::before,.mw-parser-output .hlist dd li:first-child::before,.mw-parser-output .hlist dt dd:first-child::before,.mw-parser-output .hlist dt dt:first-child::before,.mw-parser-output .hlist dt li:first-child::before,.mw-parser-output .hlist li dd:first-child::before,.mw-parser-output .hlist li dt:first-child::before,.mw-parser-output .hlist li li:first-child::before{content:" (";font-weight:normal}.mw-parser-output .hlist dd dd:last-child::after,.mw-parser-output .hlist dd dt:last-child::after,.mw-parser-output .hlist dd li:last-child::after,.mw-parser-output .hlist dt dd:last-child::after,.mw-parser-output .hlist dt dt:last-child::after,.mw-parser-output .hlist dt li:last-child::after,.mw-parser-output .hlist li dd:last-child::after,.mw-parser-output .hlist li dt:last-child::after,.mw-parser-output .hlist li li:last-child::after{content:")";font-weight:normal}.mw-parser-output .hlist ol{counter-reset:listitem}.mw-parser-output .hlist ol>li{counter-increment:listitem}.mw-parser-output .hlist ol>li::before{content:" "counter(listitem)"\a0 "}.mw-parser-output .hlist dd ol>li:first-child::before,.mw-parser-output .hlist dt ol>li:first-child::before,.mw-parser-output .hlist li ol>li:first-child::before{content:" ("counter(listitem)"\a0 "}</style><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Side_effects_of_spironolactone_in_women_in_clinical_studies_for_acne" title="Template:Side effects of spironolactone in women in clinical studies for acne"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Side_effects_of_spironolactone_in_women_in_clinical_studies_for_acne" title="Template talk:Side effects of spironolactone in women in clinical studies for acne"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Side_effects_of_spironolactone_in_women_in_clinical_studies_for_acne" title="Special:EditPage/Template:Side effects of spironolactone in women in clinical studies for acne"><abbr title="Edit this template">e</abbr></a></li></ul></div> Side effects of spironolactone in clinical studies for acne in women </caption> <tbody><tr> <th rowspan="2"><a href="/wiki/Side_effect" title="Side effect">Side effect</a></th> <th colspan="2"><a href="/wiki/Randomized_controlled_trials" class="mw-redirect" title="Randomized controlled trials"><abbr title="Randomized controlled trials">RCTs</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 Randomized controlled trials (n (<a href="/wiki/Intention-to-treat_analysis" title="Intention-to-treat analysis"><abbr title="Intention-to-treat analysis">ITT</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 Intention-to-treat analysis) = 326)</th> <th colspan="2"><a href="/wiki/Case_series" title="Case series">Case series</a> (n (<a href="/wiki/Intention-to-treat_analysis" title="Intention-to-treat analysis"><abbr title="Intention-to-treat analysis">ITT</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 Intention-to-treat analysis) = 663) </th></tr> <tr> <th>Number</th> <th>%</th> <th>Number</th> <th>% </th></tr> <tr> <td><a href="/wiki/Menstrual_irregularities" class="mw-redirect" title="Menstrual irregularities">Menstrual irregularities</a></td> <td>38</td> <td>13.4 (of 283)</td> <td>216</td> <td>33.4 (of 646) </td></tr> <tr> <td><a href="/wiki/Breast_tenderness" class="mw-redirect" title="Breast tenderness">Breast tenderness</a></td> <td>8</td> <td>2.5</td> <td>30</td> <td>4.5 </td></tr> <tr> <td><a href="/wiki/Breast_enlargement" title="Breast enlargement">Breast enlargement</a></td> <td>7</td> <td>2.1</td> <td>13</td> <td>2.0 </td></tr> <tr> <td><a href="/wiki/Dizziness" title="Dizziness">Dizziness</a>/<a href="/wiki/Vertigo" title="Vertigo">vertigo</a>/<a href="/wiki/Lightheadedness" title="Lightheadedness">lightheadedness</a></td> <td>11</td> <td>3.4</td> <td>≥19a</td> <td>≥2.9 </td></tr> <tr> <td><a href="/wiki/Headache" title="Headache">Headache</a></td> <td>5</td> <td>1.5</td> <td>≥10a</td> <td>≥1.5 </td></tr> <tr> <td><a href="/wiki/Nausea" title="Nausea">Nausea</a> and/or <a href="/wiki/Vomiting" title="Vomiting">vomiting</a></td> <td>6</td> <td>1.8</td> <td>24</td> <td>3.6 </td></tr> <tr> <td><a href="/wiki/Weight_gain" title="Weight gain">Weight gain</a>b</td> <td>5</td> <td>1.5</td> <td>1</td> <td>0.2 </td></tr> <tr> <td><a href="/wiki/Abdominal_pain" title="Abdominal pain">Abdominal pain</a></td> <td>0</td> <td>0</td> <td>≥11a</td> <td>≥1.7 </td></tr> <tr> <td><a href="/wiki/Polyuria" title="Polyuria">Polyuria</a></td> <td>2</td> <td>0.6</td> <td>8</td> <td>1.2 </td></tr> <tr> <td><a href="/wiki/Fatigue" title="Fatigue">Fatigue</a>/<a href="/wiki/Lethargy" title="Lethargy">lethargy</a></td> <td>1</td> <td>0.3</td> <td>≥12a</td> <td>≥1.8 </td></tr> <tr class="sortbottom"> <td colspan="5" style="width: 1px; font-size: small; background-color:#eaecf0; text-align: center;">Footnotes: a = Precise values unavailable due to inadequate reporting. b = Not monitored in most studies. Description: <a href="/wiki/Side_effect" title="Side effect">Side effects</a> of spironolactone (25–400 mg/day) with ≥1% incidence in a 2017 hybrid <a href="/wiki/Systematic_review" title="Systematic review">systematic review</a> of <a href="/wiki/Clinical_study" class="mw-redirect" title="Clinical study">clinical studies</a> of spironolactone for <a href="/wiki/Acne" title="Acne">acne</a> in women. Side effects with <1% incidence included <a href="/wiki/Postural_hypotension" class="mw-redirect" title="Postural hypotension">postural hypotension</a>, <a href="/wiki/Depression_(mood)" title="Depression (mood)">depression</a>, <a href="/wiki/Diarrhea" title="Diarrhea">diarrhea</a>, <a href="/wiki/Muscle_pain" class="mw-redirect" title="Muscle pain">muscle pain</a>, <a href="/wiki/Increased_appetite" class="mw-redirect" title="Increased appetite">increased appetite</a>, <a href="/wiki/Drowsiness" class="mw-redirect" title="Drowsiness">drowsiness</a>, <a href="/wiki/Rash" title="Rash">rashes</a>/<a href="/wiki/Drug_eruption" title="Drug eruption">drug eruptions</a>, <a href="/wiki/Chloasma" class="mw-redirect" title="Chloasma">chloasma</a>-like <a href="/wiki/Skin_pigmentation" class="mw-redirect" title="Skin pigmentation">skin pigmentation</a>, <a href="/wiki/Polydipsia" title="Polydipsia">polydipsia</a>, <a href="/wiki/Weakness" title="Weakness">weakness</a>, <a href="/wiki/Leg_edema" class="mw-redirect" title="Leg edema">leg edema</a>, <a href="/wiki/Change_in_libido" class="mw-redirect" title="Change in libido">libido changes</a>, and <a href="/wiki/Palpitation" class="mw-redirect" title="Palpitation">palpitations</a>. [...] Certain side effects, like <a href="/wiki/Breast_enlargement" title="Breast enlargement">breast enlargement</a>, reduced <a href="/wiki/Premenstrual_syndrome" title="Premenstrual syndrome">premenstrual symptoms</a>, and less <a href="/wiki/Greasy_skin" class="mw-redirect" title="Greasy skin">oily skin</a>/<a href="/wiki/Greasy_hair" title="Greasy hair">greasy hair</a>, could be beneficial. Side effects often could not be unambiguously attributed to spironolactone due concomitant use of other medications, particularly <a href="/wiki/Birth_control_pill" class="mw-redirect" title="Birth control pill">birth control pills</a>. <a href="/wiki/Hyperkalemia" title="Hyperkalemia">Hyperkalemia</a> was rare (14/469; 3.0%) and was "invariably mild and clinically insignificant". Risk of <a href="/wiki/Reporting_bias" title="Reporting bias">bias</a> was high and <a href="/wiki/Quality_of_evidence" class="mw-redirect" title="Quality of evidence">quality of evidence</a> was low to very low. Sources: See template. </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="High_potassium_levels">High potassium levels</h3>[<a href="/w/index.php?title=Spironolactone&action=edit&section=11" title="Edit section: High potassium levels">edit</a>]</div> Spironolactone can cause hyperkalemia, or high blood potassium levels.<a href="#cite_note-Aronson2009-111">[111]</a> Rarely, this can be fatal.<a href="#cite_note-Aronson2009-111">[111]</a> Of people with heart disease prescribed typical dosages of spironolactone, 10 to 15% develop some degree of hyperkalemia, and 6% develop severe hyperkalemia.<a href="#cite_note-Aronson2009-111">[111]</a> At a higher dosage, a rate of hyperkalemia of 24% has been observed.<a href="#cite_note-pmid26404748-119">[119]</a> An abrupt and major increase in the rate of hospitalization due to hyperkalemia from 0.2% to 11% and in the rate of death due to hyperkalemia from 0.3 per 1,000 to 2.0 per 1,000 between early 1994 and late 2001 has been attributed to a parallel rise in the number of prescriptions written for spironolactone upon the publication of the Randomized Aldactone Evaluation Study (RALES) in July 1999.<a href="#cite_note-Aronson2009-111">[111]</a><a href="#cite_note-pmid26404748-119">[119]</a><a href="#cite_note-pmid15295047-120">[120]</a><a href="#cite_note-RoncoBellomo2017-35">[35]</a> However, another population-based study in Scotland failed to replicate these findings.<a href="#cite_note-pmid22942339-121">[121]</a><a href="#cite_note-pmid20483947-122">[122]</a> The risk of hyperkalemia with spironolactone is greatest in the elderly, in people with <a href="/wiki/Renal_impairment" class="mw-redirect" title="Renal impairment">renal impairment</a> (e.g., due to <a href="/wiki/Chronic_kidney_disease" title="Chronic kidney disease">chronic kidney disease</a> or <a href="/wiki/Diabetic_nephropathy" title="Diabetic nephropathy">diabetic nephropathy</a>), in people taking certain other medications (including <a href="/wiki/ACE_inhibitor" title="ACE inhibitor"><abbr title="angiotensin-converting-enzyme">ACE</abbr> inhibitors</a>, <a href="/wiki/Angiotensin_II_receptor_blocker" title="Angiotensin II receptor blocker">angiotensin II receptor blockers</a>, <a href="/wiki/Nonsteroidal_anti-inflammatory_drug" title="Nonsteroidal anti-inflammatory drug">nonsteroidal anti-inflammatory drugs</a>, the <a href="/wiki/Antibiotic" title="Antibiotic">antibiotic</a> <a href="/wiki/Trimethoprim" title="Trimethoprim">trimethoprim</a>, and <a href="/wiki/Potassium" title="Potassium">potassium</a> <a href="/wiki/Dietary_supplement" title="Dietary supplement">supplements</a>), and at higher dosages of spironolactone.<a href="#cite_note-Aronson2009-111">[111]</a><a href="#cite_note-RoncoBellomo2017-35">[35]</a><a href="#cite_note-pmid21911446-123">[123]</a><a href="#cite_note-pmid25646289-124">[124]</a> Although spironolactone poses an important risk of hyperkalemia in the elderly, in those with kidney or cardiovascular disease, and/or in those taking medications or supplements which increase circulating potassium levels, a large retrospective study found that the rate of hyperkalemia in young women without such characteristics who had been treated with high doses of spironolactone for dermatological conditions did not differ from that of controls.<a href="#cite_note-pmid28155090-63">[63]</a><a href="#cite_note-pmid26897386-65">[65]</a><a href="#cite_note-pmid25796182-125">[125]</a> This was the conclusion of a 2017 hybrid systematic review of studies of spironolactone for acne in women as well, which found that hyperkalemia was rare and was invariably mild and clinically insignificant.<a href="#cite_note-pmid28155090-63">[63]</a> These findings suggest that hyperkalemia may not be a significant risk in such individuals, and that routine monitoring of circulating potassium levels may be unnecessary in this population.<a href="#cite_note-pmid28155090-63">[63]</a><a href="#cite_note-pmid26897386-65">[65]</a><a href="#cite_note-pmid25796182-125">[125]</a> However, other sources have claimed that hyperkalemia can nonetheless also occur in people with more normal renal function and presumably without such risk factors.<a href="#cite_note-RoncoBellomo2017-35">[35]</a> Occasional testing on a case-by-case basis in those with known risk factors may be justified.<a href="#cite_note-pmid28155090-63">[63]</a> Side effects of spironolactone which may be indicative of hyperkalemia and if persistent could justify serum potassium testing include nausea, fatigue, and particularly muscle weakness.<a href="#cite_note-pmid28155090-63">[63]</a> Notably, non-use of routine potassium monitoring with spironolactone in young women would reduce costs associated with its use.<a href="#cite_note-pmid28155090-63">[63]</a> Among young gender-diverse individuals taking spironolactone, hyperkalemia is rare and (if present) transient and asymptomatic. Larger doses do not appear to increase risks in this population.<a href="#cite_note-pmid31065620-126">[126]</a> A broader retrospective study found that the rate of hyperkalemia in gender-diverse individuals is correlated with age, with those above 45 years old being more at risk. The finding suggests that patients below or at 45 years old without other conditions that affect potassium handling can be spared from routine monitoring.<a href="#cite_note-pmid36267595-127">[127]</a> <div class="mw-heading mw-heading3"><h3 id="Breast_changes">Breast changes</h3>[<a href="/w/index.php?title=Spironolactone&action=edit&section=12" title="Edit section: Breast changes">edit</a>]</div> Spironolactone can cause <a href="/wiki/Mastodynia" class="mw-redirect" title="Mastodynia">breast pain</a> and <a href="/wiki/Mammoplasia" title="Mammoplasia">breast enlargement</a> in women.<a href="#cite_note-Becker2001-128">[128]</a><a href="#cite_note-TsioufisSchmieder2016-129">[129]</a> This is "probably because of estrogenic effects on target tissue."<a href="#cite_note-Aronson2009-111">[111]</a> At low doses, breast tenderness has been reported in only 5% of women, but at high doses, it has been reported in up to 40% of women.<a href="#cite_note-ConnJacobs1998-130">[130]</a><a href="#cite_note-pmid22468178-62">[62]</a> Breast enlargement and tenderness may occur in 26% of women at high doses.<a href="#cite_note-pmid10495361-86">[86]</a> Some women regard spironolactone-induced breast enlargement as a positive effect.<a href="#cite_note-pmid28155090-63">[63]</a> Spironolactone also commonly and dose-dependently produces <a href="/wiki/Gynecomastia" title="Gynecomastia">gynecomastia</a> (breast development) as a side effect in men.<a href="#cite_note-SeldinGiebisch1997-110">[110]</a><a href="#cite_note-TsioufisSchmieder2016-129">[129]</a><a href="#cite_note-Elsevier2014-131">[131]</a><a href="#cite_note-McInnes2008-132">[132]</a> At low doses, the rate is only 5 to 10%,<a href="#cite_note-McInnes2008-132">[132]</a> but at high doses, up to or exceeding 50% of men may develop gynecomastia.<a href="#cite_note-SeldinGiebisch1997-110">[110]</a><a href="#cite_note-TsioufisSchmieder2016-129">[129]</a><a href="#cite_note-Elsevier2014-131">[131]</a> In the RALES, 9.1% of men taking 25 mg/day spironolactone developed gynecomastia, compared to 1.3% of controls.<a href="#cite_note-pmid15134800-133">[133]</a> Conversely, in studies of healthy men given high-dose spironolactone, gynecomastia occurred in 3 of 10 (30%) at 100 mg/day, in 5 of 8 (62.5%) at 200 mg/day, and in 6 of 9 (66.7%) at 400 mg/day, relative to none of 12 controls.<a href="#cite_note-pmid8094898-134">[134]</a><a href="#cite_note-Wilcox2008-135">[135]</a> The severity of gynecomastia with spironolactone varies considerably, but is usually mild.<a href="#cite_note-SeldinGiebisch1997-110">[110]</a> As with breast enlargement caused by spironolactone in women, gynecomastia due to spironolactone in men is often although inconsistently accompanied by breast tenderness.<a href="#cite_note-SeldinGiebisch1997-110">[110]</a> In the RALES, only 1.7% of men developed breast pain, relative to 0.1% of controls.<a href="#cite_note-pmid15134800-133">[133]</a> The time to onset of spironolactone-induced gynecomastia has been found to be 27 ± 20 months at low doses and 9 ± 12 months at high doses.<a href="#cite_note-pmid15134800-133">[133]</a> Gynecomastia induced by spironolactone usually regresses after a few weeks following discontinuation of the medication.<a href="#cite_note-SeldinGiebisch1997-110">[110]</a> However, after a sufficient duration of gynecomastia being present (e.g., one year), <a href="/wiki/Hyalinization" class="mw-redirect" title="Hyalinization">hyalinization</a> and <a href="/wiki/Fibrosis" title="Fibrosis">fibrosis</a> of the tissue occurs and drug-induced gynecomastia may become irreversible.<a href="#cite_note-pmid18983216-136">[136]</a><a href="#cite_note-pmid11546925-137">[137]</a> <div class="mw-heading mw-heading3"><h3 id="Menstrual_disturbances">Menstrual disturbances</h3>[<a href="/w/index.php?title=Spironolactone&action=edit&section=13" title="Edit section: Menstrual disturbances">edit</a>]</div> Spironolactone at higher doses can cause <a href="/wiki/Menstrual_irregularities" class="mw-redirect" title="Menstrual irregularities">menstrual irregularities</a> as a side effect in women.<a href="#cite_note-pmid22468178-62">[62]</a> These irregularities include <a href="/wiki/Metrorrhagia" class="mw-redirect" title="Metrorrhagia">metrorrhagia</a> (intermenstrual bleeding), <a href="/wiki/Amenorrhea" title="Amenorrhea">amenorrhea</a> (absence of menstruation), and <a href="/wiki/Breakthrough_bleeding" class="mw-redirect" title="Breakthrough bleeding">breakthrough bleeding</a>.<a href="#cite_note-pmid22468178-62">[62]</a> They are common during spironolactone therapy, with 10 to 50% of women experiencing them at moderate doses and almost all experiencing them at a high doses.<a href="#cite_note-pmid10495361-86">[86]</a><a href="#cite_note-Aronson2009-111">[111]</a> For example, about 20% of women experienced menstrual irregularities with 50 to 100 mg/day spironolactone, whereas about 70% experienced menstrual irregularities at 200 mg/day.<a href="#cite_note-pmid22468178-62">[62]</a> Most women taking moderate doses of spironolactone develop amenorrhea, and normal <a href="/wiki/Menstruation" title="Menstruation">menstruation</a> usually returns within two months of discontinuation.<a href="#cite_note-Aronson2009-111">[111]</a> Spironolactone produces an <a href="/wiki/Irregular_menstruation" title="Irregular menstruation">irregular</a> and <a href="/wiki/Anovulation" title="Anovulation">anovulatory</a> pattern of <a href="/wiki/Menstrual_cycle" title="Menstrual cycle">menstrual cycles</a>.<a href="#cite_note-pmid10495361-86">[86]</a> It is also associated with metrorrhagia and <a href="/wiki/Menorrhagia" class="mw-redirect" title="Menorrhagia">menorrhagia</a> (heavy menstrual bleeding) in large percentages of women,<a href="#cite_note-Becker2001-128">[128]</a> as well as with <a href="/wiki/Polymenorrhea" title="Polymenorrhea">polymenorrhea</a> (short menstrual cycles).<a href="#cite_note-pmid16076921-138">[138]</a><a href="#cite_note-pmid10792338-139">[139]</a> The medication reportedly has no <a href="/wiki/Contraceptive" class="mw-redirect" title="Contraceptive">birth control</a> effect.<a href="#cite_note-RabeGrunwald2009-140">[140]</a> It has been suggested that the weak progestogenic activity of spironolactone is responsible for these effects, although this has not been established and spironolactone has been shown to possess insignificant progestogenic and antiprogestogenic activity even at high dosages in women.<a href="#cite_note-pmid10495361-86">[86]</a><a href="#cite_note-pmid8144871-141">[141]</a><a href="#cite_note-pmid2744183-142">[142]</a> An alternative proposed cause is inhibition of 17α-hydroxylase and hence <a href="/wiki/Sex_steroid" class="mw-redirect" title="Sex steroid">sex steroid</a> <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> by spironolactone and consequent changes in sex hormone levels.<a href="#cite_note-SeldinGiebisch1997-110">[110]</a> Indeed, <a href="/wiki/CYP17A1" title="CYP17A1">CYP17A1</a> <a href="/wiki/Genotype" title="Genotype">genotype</a> is associated with polymenorrhea.<a href="#cite_note-pmid32038990-143">[143]</a> Regardless of their mechanism, the menstrual disturbances associated with spironolactone can usually be controlled well by concomitant treatment with a <a href="/wiki/Birth_control_pill" class="mw-redirect" title="Birth control pill">birth control pill</a>, due to the <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestin</a> component.<a href="#cite_note-pmid10495361-86">[86]</a><a href="#cite_note-JemecRevuz2006-144">[144]</a> <div class="mw-heading mw-heading3"><h3 id="Mood_changes">Mood changes</h3>[<a href="/w/index.php?title=Spironolactone&action=edit&section=14" title="Edit section: Mood changes">edit</a>]</div> Research is mixed on whether antimineralocorticoids like spironolactone have positive or negative effects on <a href="/wiki/Mood_(psychology)" title="Mood (psychology)">mood</a>.<a href="#cite_note-pmid25459896-145">[145]</a><a href="#cite_note-Schultebraucks2016-146">[146]</a><a href="#cite_note-pmid10367986-147">[147]</a> In any case, it is possible that spironolactone might have the capacity to increase the risk of <a href="/wiki/Depression_(mood)" title="Depression (mood)">depressive</a> symptoms.<a href="#cite_note-pmid25459896-145">[145]</a><a href="#cite_note-Schultebraucks2016-146">[146]</a><a href="#cite_note-pmid10367986-147">[147]</a> However, a 2017 hybrid systematic review found that the incidence of depression in women treated with spironolactone for acne was less than 1%.<a href="#cite_note-pmid28155090-63">[63]</a> Likewise, a 10-year observational study found that the incidence of depression in 196 transgender women taking high-dose spironolactone in combination with an estrogen was less than 1%.<a href="#cite_note-BassonPrior1997-148">[148]</a> <div class="mw-heading mw-heading3"><h3 id="Lipid_changes">Lipid changes</h3>[<a href="/w/index.php?title=Spironolactone&action=edit&section=15" title="Edit section: Lipid changes">edit</a>]</div> Spironolactone has been found to increase <a href="/wiki/LDL_cholesterol" class="mw-redirect" title="LDL cholesterol">LDL ("bad") cholesterol</a> and decrease <a href="/wiki/HDL_cholesterol" class="mw-redirect" title="HDL cholesterol">HDL ("good") cholesterol</a> levels at the relatively high doses used in women with <a href="/wiki/Polycystic_ovary_syndrome" title="Polycystic ovary syndrome">polycystic ovary syndrome</a> (PCOS).<a href="#cite_note-pmid28944709-149">[149]</a><a href="#cite_note-pmid19843067-150">[150]</a> As such, it may have unfavorable effects on the <a href="/wiki/Blood_lipids" title="Blood lipids">blood</a> <a href="/wiki/Lipid_profile" title="Lipid profile">lipid profile</a> in this context.<a href="#cite_note-pmid28944709-149">[149]</a><a href="#cite_note-pmid19843067-150">[150]</a> Heightened LDL cholesterol levels are a potential <a href="/wiki/Risk_factor" title="Risk factor">risk factor</a> for <a href="/wiki/Cardiovascular_disease" title="Cardiovascular disease">cardiovascular disease</a> such as <a href="/wiki/Atherosclerosis" title="Atherosclerosis">atherosclerosis</a> or <a href="/wiki/Coronary_heart_disease" class="mw-redirect" title="Coronary heart disease">coronary heart disease</a>.<a href="#cite_note-pmid30586774-151">[151]</a> Consequently, it has been said that spironolactone should not be given to women with <a href="/wiki/Dyslipidemia" title="Dyslipidemia">dyslipidemia</a> (e.g., <a href="/wiki/Hypercholesterolemia" title="Hypercholesterolemia">high cholesterol</a>).<a href="#cite_note-pmid28944709-149">[149]</a><a href="#cite_note-pmid19843067-150">[150]</a> Unfavorable lipid changes have also been seen with other antiandrogens, like <a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">cyproterone acetate</a><a href="#cite_note-WPATH-SOC8-152">[152]</a><a href="#cite_note-pmid3318361-153">[153]</a> and <a href="/wiki/Bicalutamide" title="Bicalutamide">bicalutamide</a>.<a href="#cite_note-pmid33334002-154">[154]</a><a href="#cite_note-pmid29211888-84">[84]</a> <div class="mw-heading mw-heading3"><h3 id="Rare_reactions">Rare reactions</h3>[<a href="/w/index.php?title=Spironolactone&action=edit&section=16" title="Edit section: Rare reactions">edit</a>]</div> Aside from hyperkalemia, spironolactone may rarely cause adverse reactions such as <a href="/wiki/Anaphylaxis" title="Anaphylaxis">anaphylaxis</a>, <a href="/wiki/Kidney_failure" title="Kidney failure">kidney failure</a>,<a href="#cite_note-pmid19006114-155">[155]</a> <a href="/wiki/Hepatitis" title="Hepatitis">hepatitis</a> (two reported cases, neither serious),<a href="#cite_note-ThaiSinclair2001-156">[156]</a> <a href="/wiki/Agranulocytosis" title="Agranulocytosis">agranulocytosis</a>, <a href="/wiki/DRESS_syndrome" class="mw-redirect" title="DRESS syndrome">DRESS syndrome</a>, <a href="/wiki/Stevens%E2%80%93Johnson_syndrome" title="Stevens–Johnson syndrome">Stevens–Johnson syndrome</a> or <a href="/wiki/Toxic_epidermal_necrolysis" title="Toxic epidermal necrolysis">toxic epidermal necrolysis</a>.<a href="#cite_note-157">[157]</a><a href="#cite_note-158">[158]</a> Five cases of <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a> in patients who took spironolactone for prolonged periods of time have been reported.<a href="#cite_note-Aronson2009-111">[111]</a><a href="#cite_note-McInnes2008-132">[132]</a> <div class="mw-heading mw-heading3"><h3 id="Spironolactone_bodies">Spironolactone bodies</h3>[<a href="/w/index.php?title=Spironolactone&action=edit&section=17" title="Edit section: Spironolactone bodies">edit</a>]</div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Spironolactone_bodies.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Spironolactone_bodies.png/175px-Spironolactone_bodies.png" decoding="async" width="175" height="131" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Spironolactone_bodies.png/263px-Spironolactone_bodies.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Spironolactone_bodies.png/350px-Spironolactone_bodies.png 2x" data-file-width="862" data-file-height="643" /></a><figcaption><a href="/wiki/Micrograph" title="Micrograph">Micrograph</a> (<a href="/wiki/H%26E_stain" title="H&E stain">H&E stain</a>) of an <a href="/wiki/Adrenal_gland" title="Adrenal gland">adrenal gland</a> showing spironolactone bodies.</figcaption></figure> Long-term administration of spironolactone gives the <a href="/wiki/Histologic" class="mw-redirect" title="Histologic">histologic</a> characteristic of "spironolactone bodies" in the <a href="/wiki/Adrenal_cortex" title="Adrenal cortex">adrenal cortex</a>. Spironolactone bodies are <a href="/wiki/Eosinophilic" title="Eosinophilic">eosinophilic</a>, round, concentrically laminated <a href="/wiki/Cytoplasm" title="Cytoplasm">cytoplasmic</a> inclusions surrounded by clear halos in preparations stained with <a href="/wiki/Hematoxylin" class="mw-redirect" title="Hematoxylin">hematoxylin</a> and <a href="/wiki/Eosin" title="Eosin">eosin</a>.<a href="#cite_note-pmid7195152-159">[159]</a> <div class="mw-heading mw-heading3"><h3 id="Pregnancy_and_breastfeeding">Pregnancy and breastfeeding</h3>[<a href="/w/index.php?title=Spironolactone&action=edit&section=18" title="Edit section: Pregnancy and breastfeeding">edit</a>]</div> Spironolactone is able to cross the <a href="/wiki/Placenta" title="Placenta">placenta</a>.<a href="#cite_note-Becker2001-128">[128]</a> It has been found to be present in the breast milk of lactating mothers.<a href="#cite_note-Aldactone_label-8">[8]</a> However, only very small amounts of spironolactone and its metabolite canrenone enter <a href="/wiki/Breast_milk" title="Breast milk">breast milk</a>, and the amount received by an infant during breastfeeding (<0.5% of the mother's dose) is considered to be insignificant.<a href="#cite_note-Ainsworth2014-160">[160]</a> A study found that spironolactone was not associated with <a href="/wiki/Teratogen" class="mw-redirect" title="Teratogen">teratogenicity</a> in the offspring of rats.<a href="#cite_note-Little2006-161">[161]</a><a href="#cite_note-RubinRamsey2008-162">[162]</a><a href="#cite_note-BriggsFreeman2011-163">[163]</a> Because it is an antiandrogen, however, spironolactone could theoretically have the potential to cause feminization of male fetuses at sufficient doses.<a href="#cite_note-Little2006-161">[161]</a><a href="#cite_note-RubinRamsey2008-162">[162]</a> In accordance, a subsequent study found that partial feminization of the genitalia occurred in the male offspring of rats that received doses of spironolactone that were five times higher than those normally used in humans (200 mg/kg per day).<a href="#cite_note-Little2006-161">[161]</a><a href="#cite_note-BriggsFreeman2011-163">[163]</a> Another study found permanent, dose-related reproductive tract abnormalities rat offspring of both sexes at lower doses (50 to 100 mg/kg per day).<a href="#cite_note-BriggsFreeman2011-163">[163]</a> In practice however, although experience is limited, spironolactone has never been reported to cause observable feminization or any other congenital defects in humans.<a href="#cite_note-Little2006-161">[161]</a><a href="#cite_note-RubinRamsey2008-162">[162]</a><a href="#cite_note-ElkayamGleicher1998-164">[164]</a><a href="#cite_note-Schaefer2001-165">[165]</a> Among 31 human newborns exposed to spironolactone in the first trimester, there were no signs of any specific <a href="/wiki/Birth_defect" title="Birth defect">birth defects</a>.<a href="#cite_note-Schaefer2001-165">[165]</a> A case report described a woman who was prescribed spironolactone during pregnancy with triplets and delivered all three (one boy and two girls) healthy; there was no feminization in the boy.<a href="#cite_note-Schaefer2001-165">[165]</a> In addition, spironolactone has been used at high doses to treat pregnant women with <a href="/wiki/Bartter%27s_syndrome" class="mw-redirect" title="Bartter's syndrome">Bartter's syndrome</a>, and none of the infants (three boys, two girls) showed toxicity, including feminization in the male infants.<a href="#cite_note-Ainsworth2014-160">[160]</a><a href="#cite_note-Little2006-161">[161]</a> There are similar findings, albeit also limited, for another antiandrogen, cyproterone acetate (prominent genital defects in male rats, but no human abnormalities (including feminization of male fetuses) at both a low dose of 2 mg/day or high doses of 50 to 100 mg/day).<a href="#cite_note-Schaefer2001-165">[165]</a> In any case, spironolactone is nonetheless not recommended during pregnancy due to theoretical concerns relating to feminization of males and also to potential alteration of fetal potassium levels.<a href="#cite_note-Little2006-161">[161]</a><a href="#cite_note-Upfal2006-166">[166]</a> A 2019 systematic review found insufficient evidence that spironolactone causes birth defects in humans.<a href="#cite_note-pmid30352280-167">[167]</a> However, there was also insufficient evidence to be certain that it does not.<a href="#cite_note-pmid30352280-167">[167]</a> <div class="mw-heading mw-heading2"><h2 id="Overdose">Overdose</h2>[<a href="/w/index.php?title=Spironolactone&action=edit&section=19" title="Edit section: Overdose">edit</a>]</div> Spironolactone is relatively safe in acute <a href="/wiki/Overdose" class="mw-redirect" title="Overdose">overdose</a>.<a href="#cite_note-Aldactone_label-8">[8]</a> <a href="/wiki/Symptom" class="mw-redirect" title="Symptom">Symptoms</a> following an acute overdose of spironolactone may include <a href="/wiki/Drowsiness" class="mw-redirect" title="Drowsiness">drowsiness</a>, <a href="/wiki/Mental_confusion" class="mw-redirect" title="Mental confusion">confusion</a>, <a href="/wiki/Maculopapular_rash" title="Maculopapular rash">maculopapular</a> or <a href="/wiki/Erythematous_rash" class="mw-redirect" title="Erythematous rash">erythematous rash</a>, <a href="/wiki/Nausea" title="Nausea">nausea</a>, <a href="/wiki/Vomiting" title="Vomiting">vomiting</a>, <a href="/wiki/Dizziness" title="Dizziness">dizziness</a>, and <a href="/wiki/Diarrhea" title="Diarrhea">diarrhea</a>.<a href="#cite_note-Aldactone_label-8">[8]</a> In rare cases, <a href="/wiki/Hyponatremia" title="Hyponatremia">hyponatremia</a>, <a href="/wiki/Hyperkalemia" title="Hyperkalemia">hyperkalemia</a>, or <a href="/wiki/Hepatic_coma" class="mw-redirect" title="Hepatic coma">hepatic coma</a> may occur in individuals with <a href="/wiki/Severe_liver_disease" class="mw-redirect" title="Severe liver disease">severe liver disease</a>.<a href="#cite_note-Aldactone_label-8">[8]</a> However, these <a href="/wiki/Adverse_reaction" class="mw-redirect" title="Adverse reaction">adverse reactions</a> are unlikely in the event of an acute overdose.<a href="#cite_note-Aldactone_label-8">[8]</a> Hyperkalemia can occur following an overdose of spironolactone, and this is especially so in people with <a href="/wiki/Chronic_kidney_disease" title="Chronic kidney disease">decreased kidney function</a>.<a href="#cite_note-Aldactone_label-8">[8]</a> Spironolactone has been studied at extremely high oral doses of up to 2,400 mg per day in <a href="/wiki/Clinical_trial" title="Clinical trial">clinical trials</a>.<a href="#cite_note-pmid28634268-107">[107]</a><a href="#cite_note-pmid15134797-168">[168]</a> Its oral <a href="/wiki/Median_lethal_dose" title="Median lethal dose">median lethal dose</a> (LD50) is more than 1,000 mg/kg in mice, rats, and rabbits.<a href="#cite_note-Aldactone_label-8">[8]</a> There is no specific <a href="/wiki/Antidote" title="Antidote">antidote</a> for overdose of spironolactone.<a href="#cite_note-Aldactone_label-8">[8]</a> Treatment may consist of induction of <a href="/wiki/Vomiting" title="Vomiting">vomiting</a> or <a href="/wiki/Stomach" title="Stomach">stomach</a> evacuation by <a href="/wiki/Gastric_lavage" title="Gastric lavage">gastric lavage</a>.<a href="#cite_note-Aldactone_label-8">[8]</a> The treatment of spironolactone overdose is supportive, with the purpose of maintaining <a href="/wiki/Tissue_hydration" title="Tissue hydration">hydration</a>, <a href="/wiki/Electrolyte_balance" class="mw-redirect" title="Electrolyte balance">electrolyte balance</a>, and <a href="/wiki/Vital_function" class="mw-redirect" title="Vital function">vital functions</a>.<a href="#cite_note-Aldactone_label-8">[8]</a> Spironolactone should be discontinued in people with impaired kidney function or hyperkalemia.<a href="#cite_note-Aldactone_label-8">[8]</a> <div class="mw-heading mw-heading2"><h2 id="Interactions">Interactions</h2>[<a href="/w/index.php?title=Spironolactone&action=edit&section=20" title="Edit section: Interactions">edit</a>]</div> Spironolactone often increases serum <a href="/wiki/Potassium" title="Potassium">potassium</a> levels and can cause <a href="/wiki/Hyperkalemia" title="Hyperkalemia">hyperkalemia</a>, a very serious condition. Therefore, it is recommended that people using this medication avoid potassium supplements and salt substitutes containing potassium.<a href="#cite_note-169">[169]</a> Physicians must be careful to monitor potassium levels in both males and females who are taking spironolactone as a diuretic, especially during the first twelve months of use and whenever the dosage is increased. Doctors may also recommend that some patients may be advised to limit dietary consumption of potassium-rich foods. However, recent data suggests that both potassium monitoring and dietary restriction of potassium intake is unnecessary in healthy young women taking spironolactone for acne<a href="#cite_note-pmid25796182-125">[125]</a> and in healthy young gender-diverse individuals taking spironolactone for hormone therapy.<a href="#cite_note-pmid36267595-127">[127]</a> Spironolactone together with <a href="/wiki/Trimethoprim/sulfamethoxazole" title="Trimethoprim/sulfamethoxazole">trimethoprim/sulfamethoxazole</a> increases the likelihood of hyperkalemia, especially in the elderly. The trimethoprim portion acts to prevent potassium excretion in the distal tubule of the nephron.<a href="#cite_note-170">[170]</a> Spironolactone has been reported to induce the <a href="/wiki/Enzyme" title="Enzyme">enzymes</a> <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a> and certain <a href="/wiki/UDP-glucuronosyltransferase" class="mw-redirect" title="UDP-glucuronosyltransferase">UDP-glucuronosyltransferases</a> (UGTs), which can result in <a href="/wiki/Drug_interaction" title="Drug interaction">interactions</a> with various medications.<a href="#cite_note-Parkinson2001-17">[17]</a><a href="#cite_note-Davis2009-171">[171]</a><a href="#cite_note-pmid1826112-172">[172]</a> However, it has also been reported that metabolites of spironolactone <a href="/wiki/Irreversible_inhibition" class="mw-redirect" title="Irreversible inhibition">irreversibly inhibit</a> CYP3A4.<a href="#cite_note-Wolverton2007-173">[173]</a> In any case, spironolactone has been found to reduce the <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> of oral <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a>, which could be due to induction of estradiol metabolism via CYP3A4.<a href="#cite_note-pmid29756046-174">[174]</a> Spironolactone has also been found to <a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibit</a> <a href="/wiki/UGT2B7" title="UGT2B7">UGT2B7</a>.<a href="#cite_note-JhajraRamesh_Varkhede2012-175">[175]</a> Spironolactone can also have numerous other interactions, most commonly with other <a href="/wiki/Cardiac" class="mw-redirect" title="Cardiac">cardiac</a> and blood pressure medications, for instance <a href="/wiki/Digoxin" title="Digoxin">digoxin</a>.<a href="#cite_note-Aldactone_label-8">[8]</a> <a href="/wiki/Licorice" class="mw-redirect" title="Licorice">Licorice</a>, which has indirect mineralocorticoid activity by inhibiting mineralocorticoid metabolism, has been found to inhibit the antimineralocorticoid effects of spironolactone.<a href="#cite_note-pmid27450358-176">[176]</a><a href="#cite_note-pmid17113210-177">[177]</a><a href="#cite_note-pmid13991036-178">[178]</a> Moreover, the addition of licorice to spironolactone has been found to reduce the antimineralocorticoid side effects of spironolactone in women treated with it for hyperandrogenism, and licorice hence may be used to reduce these side effects in women treated with spironolactone as an antiandrogen who are bothered by them.<a href="#cite_note-pmid27450358-176">[176]</a><a href="#cite_note-pmid17113210-177">[177]</a> On the opposite end of the spectrum, spironolactone is useful in reversing licorice-induced <a href="/wiki/Hypokalemia" title="Hypokalemia">hypokalemia</a>.<a href="#cite_note-pmid23185686-179">[179]</a><a href="#cite_note-pmid12640291-180">[180]</a> <a href="/wiki/Aspirin" title="Aspirin">Aspirin</a> and other <a href="/wiki/Nonsteroidal_anti-inflammatory_drug" title="Nonsteroidal anti-inflammatory drug">nonsteroidal anti-inflammatory drugs</a> (NSAIDs) have been found to attenuate the <a href="/wiki/Diuresis" title="Diuresis">diuresis</a> and <a href="/wiki/Natriuresis" title="Natriuresis">natriuresis</a> induced by spironolactone, but, not to affect its antihypertensive effect.<a href="#cite_note-EndouHosoyamada1995-37">[37]</a><a href="#cite_note-pmid17362671-181">[181]</a> Some research has suggested that spironolactone might be able to interfere with the effectiveness of <a href="/wiki/Antidepressant" title="Antidepressant">antidepressant</a> treatment. As the medication acts as an antimineralocorticoid, it is thought that it might be able to reduce the effectiveness of certain antidepressants by interfering with normalization of the <a href="/wiki/Hypothalamic%E2%80%93pituitary%E2%80%93adrenal_axis" title="Hypothalamic–pituitary–adrenal axis">hypothalamic–pituitary–adrenal axis</a> and by increasing levels of <a href="/wiki/Glucocorticoid" title="Glucocorticoid">glucocorticoids</a> such as <a href="/wiki/Cortisol" title="Cortisol">cortisol</a>.<a href="#cite_note-182">[182]</a><a href="#cite_note-pmid19909979-183">[183]</a> However, other research contradicts this hypothesis and has suggested that spironolactone might actually produce antidepressant effects, for instance studies showing antidepressant-like effects of spironolactone in animals.<a href="#cite_note-pmid21515309-184">[184]</a> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2>[<a href="/w/index.php?title=Spironolactone&action=edit&section=21" title="Edit section: Pharmacology">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Pharmacodynamics">Pharmacodynamics</h3>[<a href="/w/index.php?title=Spironolactone&action=edit&section=22" title="Edit section: Pharmacodynamics">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Pharmacodynamics_of_spironolactone" title="Pharmacodynamics of spironolactone">Pharmacodynamics of spironolactone</a></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:7%CE%B1-Thiomethylspironolactone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e8/7%CE%B1-Thiomethylspironolactone.svg/220px-7%CE%B1-Thiomethylspironolactone.svg.png" decoding="async" width="220" height="151" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e8/7%CE%B1-Thiomethylspironolactone.svg/330px-7%CE%B1-Thiomethylspironolactone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e8/7%CE%B1-Thiomethylspironolactone.svg/440px-7%CE%B1-Thiomethylspironolactone.svg.png 2x" data-file-width="1290" data-file-height="885" /></a><figcaption><a href="/wiki/7%CE%B1-Thiomethylspironolactone" title="7α-Thiomethylspironolactone">7α-Thiomethylspironolactone</a>, the major <a href="/wiki/Active_metabolite" title="Active metabolite">active form</a> of spironolactone. It accounts for about 80% of the potassium-sparing effect of spironolactone.<a href="#cite_note-pmid15947888-11">[11]</a><a href="#cite_note-AgustiBourgeois2013-185">[185]</a><a href="#cite_note-CancerOrganization2001-186">[186]</a></figcaption></figure> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Canrenone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/db/Canrenone.svg/220px-Canrenone.svg.png" decoding="async" width="220" height="154" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/db/Canrenone.svg/330px-Canrenone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/db/Canrenone.svg/440px-Canrenone.svg.png 2x" data-file-width="512" data-file-height="359" /></a><figcaption><a href="/wiki/Canrenone" title="Canrenone">Canrenone</a>, the second major <a href="/wiki/Active_metabolite" title="Active metabolite">active form</a> of spironolactone. It accounts for around 10 to 25% of the potassium-sparing effect of spironolactone.<a href="#cite_note-GinésArroyo2008-187">[187]</a></figcaption></figure> The <a href="/wiki/Pharmacodynamics" title="Pharmacodynamics">pharmacodynamics</a> of spironolactone are characterized by high <a href="/wiki/Antimineralocorticoid" class="mw-redirect" title="Antimineralocorticoid">antimineralocorticoid</a> activity, moderate <a href="/wiki/Antiandrogen" title="Antiandrogen">antiandrogenic</a> activity, and weak <a href="/wiki/Steroidogenesis_inhibitor" title="Steroidogenesis inhibitor">steroidogenesis inhibition</a>, among other more minor activities.<a href="#cite_note-pmid28634268-107">[107]</a><a href="#cite_note-pmid984618-109">[109]</a><a href="#cite_note-pmid8094898-134">[134]</a> Spironolactone is a <a href="/wiki/Prodrug" title="Prodrug">prodrug</a>, so most of its actions are actually mediated by its various <a href="/wiki/Active_metabolite" title="Active metabolite">active metabolites</a>.<a href="#cite_note-pmid28634268-107">[107]</a> The major active forms of spironolactone are <a href="/wiki/7%CE%B1-thiomethylspironolactone" class="mw-redirect" title="7α-thiomethylspironolactone">7α-thiomethylspironolactone</a> (7α-TMS) and <a href="/wiki/Canrenone" title="Canrenone">canrenone</a> (7α-desthioacetyl-δ6-spironolactone).<a href="#cite_note-pmid15947888-11">[11]</a><a href="#cite_note-pmid28634268-107">[107]</a> Spironolactone is a <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potent</a> antimineralocorticoid.<a href="#cite_note-pmid15947888-11">[11]</a> That is, it is an <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonist</a> of the <a href="/wiki/Mineralocorticoid_receptor" title="Mineralocorticoid receptor">mineralocorticoid receptor</a> (MR), the <a href="/wiki/Biological_target" title="Biological target">biological target</a> of <a href="/wiki/Mineralocorticoid" title="Mineralocorticoid">mineralocorticoids</a> like <a href="/wiki/Aldosterone" title="Aldosterone">aldosterone</a> and <a href="/wiki/11-deoxycorticosterone" class="mw-redirect" title="11-deoxycorticosterone">11-deoxycorticosterone</a>.<a href="#cite_note-pmid15947888-11">[11]</a> By blocking the MR, spironolactone inhibits the effects of mineralocorticoids in the body.<a href="#cite_note-pmid15947888-11">[11]</a> The antimineralocorticoid activity of spironolactone is responsible for its therapeutic efficacy in the treatment of <a href="/wiki/Edema" title="Edema">edema</a>, <a href="/wiki/High_blood_pressure" class="mw-redirect" title="High blood pressure">high blood pressure</a>, <a href="/wiki/Heart_failure" title="Heart failure">heart failure</a>, <a href="/wiki/Hyperaldosteronism" title="Hyperaldosteronism">hyperaldosteronism</a>, and <a href="/wiki/Ascites" title="Ascites">ascites</a> due to <a href="/wiki/Cirrhosis" title="Cirrhosis">cirrhosis</a>.<a href="#cite_note-Feldman2008-188">[188]</a><a href="#cite_note-Health2015-189">[189]</a> It is also responsible for many of the side effects of spironolactone, such as <a href="/wiki/Urinary_frequency" class="mw-redirect" title="Urinary frequency">urinary frequency</a>, <a href="/wiki/Dehydration" title="Dehydration">dehydration</a>, <a href="/wiki/Hyponatremia" title="Hyponatremia">hyponatremia</a>, <a href="/wiki/Low_blood_pressure" class="mw-redirect" title="Low blood pressure">low blood pressure</a>, <a href="/wiki/Fatigue_(medical)" class="mw-redirect" title="Fatigue (medical)">fatigue</a>, <a href="/wiki/Dizziness" title="Dizziness">dizziness</a>, <a href="/wiki/Metabolic_acidosis" title="Metabolic acidosis">metabolic acidosis</a>, decreased <a href="/wiki/Kidney_function" class="mw-redirect" title="Kidney function">kidney function</a>, and its risk of <a href="/wiki/Hyperkalemia" title="Hyperkalemia">hyperkalemia</a>.<a href="#cite_note-pmid24456327-190">[190]</a> Due to the antimineralocorticoid activity of spironolactone, levels of <a href="/wiki/Aldosterone" title="Aldosterone">aldosterone</a> are significantly increased by the medication, probably reflecting an attempt of the body to maintain <a href="/wiki/Homeostasis" title="Homeostasis">homeostasis</a>.<a href="#cite_note-pmid9420861-60">[60]</a><a href="#cite_note-pmid10495361-86">[86]</a> Spironolactone is a moderate antiandrogen.<a href="#cite_note-pmid984618-109">[109]</a><a href="#cite_note-pmid8144871-141">[141]</a><a href="#cite_note-pmid1826112-172">[172]</a> That is, it is an <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonist</a> of the <a href="/wiki/Androgen_receptor" title="Androgen receptor">androgen receptor</a> (AR), the biological target of <a href="/wiki/Androgen" title="Androgen">androgens</a> like <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> and <a href="/wiki/Dihydrotestosterone" title="Dihydrotestosterone">dihydrotestosterone</a> (DHT).<a href="#cite_note-pmid984618-109">[109]</a><a href="#cite_note-pmid8144871-141">[141]</a><a href="#cite_note-pmid1826112-172">[172]</a> By blocking the AR, spironolactone inhibits the effects of androgens in the body.<a href="#cite_note-pmid984618-109">[109]</a><a href="#cite_note-pmid8144871-141">[141]</a><a href="#cite_note-pmid1826112-172">[172]</a> The antiandrogenic activity of spironolactone is mainly responsible for its therapeutic efficacy in the treatment of <a href="/wiki/Androgen-dependent_condition" title="Androgen-dependent condition">androgen-dependent</a> <a href="/wiki/Cutaneous_condition" class="mw-redirect" title="Cutaneous condition">skin and hair conditions</a> like <a href="/wiki/Acne" title="Acne">acne</a>, <a href="/wiki/Seborrhea" class="mw-redirect" title="Seborrhea">seborrhea</a>, <a href="/wiki/Hirsutism" title="Hirsutism">hirsutism</a>, and <a href="/wiki/Pattern_hair_loss" title="Pattern hair loss">pattern hair loss</a> and <a href="/wiki/Hyperandrogenism" title="Hyperandrogenism">hyperandrogenism</a> in women, <a href="/wiki/Precocious_puberty" title="Precocious puberty">precocious puberty</a> in boys with <a href="/wiki/Testotoxicosis" class="mw-redirect" title="Testotoxicosis">testotoxicosis</a>, and as a component of <a href="/wiki/Feminizing_hormone_therapy" title="Feminizing hormone therapy">feminizing hormone therapy</a> for <a href="/wiki/Transgender_women" class="mw-redirect" title="Transgender women">transgender women</a>.<a href="#cite_note-pmid8144871-141">[141]</a><a href="#cite_note-pmid29756046-174">[174]</a><a href="#cite_note-pmid11322868-191">[191]</a> It is also primarily responsible for some of its side effects, like <a href="/wiki/Breast_tenderness" class="mw-redirect" title="Breast tenderness">breast tenderness</a>, <a href="/wiki/Gynecomastia" title="Gynecomastia">gynecomastia</a>, <a href="/wiki/Feminization_(biology)" title="Feminization (biology)">feminization</a>, and <a href="/wiki/Demasculinization" class="mw-redirect" title="Demasculinization">demasculinization</a> in men.<a href="#cite_note-SeldinGiebisch1997-110">[110]</a><a href="#cite_note-pmid11322868-191">[191]</a> Blockade of androgen signaling in the <a href="/wiki/Breast" title="Breast">breast</a> disinhibits the actions of <a href="/wiki/Estrogen" title="Estrogen">estrogens</a> in this tissue.<a href="#cite_note-StraussIII2013-192">[192]</a> Although useful as an antiandrogen in women, who have low testosterone levels compared to men,<a href="#cite_note-pmid2941190-193">[193]</a><a href="#cite_note-GregoryTravis2015-194">[194]</a> spironolactone is described as having relatively weak antiandrogenic activity.<a href="#cite_note-Wu2012-195">[195]</a><a href="#cite_note-pmid11322868-191">[191]</a><a href="#cite_note-BenniVemer1990-196">[196]</a><a href="#cite_note-pmid8915726-197">[197]</a> Spironolactone is a weak steroidogenesis inhibitor.<a href="#cite_note-pmid984618-109">[109]</a><a href="#cite_note-pmid8094898-134">[134]</a><a href="#cite_note-pmid8144871-141">[141]</a><a href="#cite_note-pmid6786868-198">[198]</a> That is, it inhibits <a href="/wiki/Steroidogenic_enzyme" title="Steroidogenic enzyme">steroidogenic enzymes</a>, or <a href="/wiki/Enzyme" title="Enzyme">enzymes</a> involved in the <a href="/wiki/Steroidogenesis" class="mw-redirect" title="Steroidogenesis">production of steroid hormones</a>.<a href="#cite_note-pmid984618-109">[109]</a><a href="#cite_note-pmid8094898-134">[134]</a><a href="#cite_note-pmid8144871-141">[141]</a><a href="#cite_note-pmid6786868-198">[198]</a> Spironolactone and/or its metabolites have been found <a href="/wiki/In_vitro" title="In vitro">in vitro</a> to weakly <a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibit</a> a broad array of steroidogenic enzymes including <a href="/wiki/Cholesterol_side-chain_cleavage_enzyme" title="Cholesterol side-chain cleavage enzyme">cholesterol side-chain cleavage enzyme</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/5%CE%B1-reductase" class="mw-redirect" title="5α-reductase">5α-reductase</a>, <a href="/wiki/3%CE%B2-hydroxysteroid_dehydrogenase" class="mw-redirect" title="3β-hydroxysteroid dehydrogenase">3β-hydroxysteroid dehydrogenase</a>, <a href="/wiki/11%CE%B2-hydroxylase" class="mw-redirect" title="11β-hydroxylase">11β-hydroxylase</a>, <a href="/wiki/21-hydroxylase" class="mw-redirect" title="21-hydroxylase">21-hydroxylase</a>, and <a href="/wiki/Aldosterone_synthase" title="Aldosterone synthase">aldosterone synthase</a> (18-hydroxylase).<a href="#cite_note-pmid8144871-141">[141]</a><a href="#cite_note-pmid6786868-198">[198]</a><a href="#cite_note-pmid26001184-199">[199]</a><a href="#cite_note-pmid18819053-200">[200]</a> However, although very high doses of spironolactone can considerably decrease steroid hormone levels in animals, spironolactone has shown mixed and inconsistent effects on steroid hormone levels in clinical studies, even at high clinical doses.<a href="#cite_note-pmid28155090-63">[63]</a><a href="#cite_note-pmid984618-109">[109]</a><a href="#cite_note-pmid8094898-134">[134]</a><a href="#cite_note-pmid8144871-141">[141]</a><a href="#cite_note-pmid1826112-172">[172]</a> In any case, the levels of most steroid hormones, including testosterone and <a href="/wiki/Cortisol" title="Cortisol">cortisol</a>, are usually unchanged by spironolactone in humans, which may in part be related to compensatory upregulation of their synthesis.<a href="#cite_note-pmid984618-109">[109]</a><a href="#cite_note-pmid8094898-134">[134]</a><a href="#cite_note-WattsFaingold2009-201">[201]</a> The weak steroidogenesis inhibition of spironolactone might contribute to its antiandrogenic efficacy to some degree and may explain its side effect of menstrual irregularities in women.<a href="#cite_note-pmid984618-109">[109]</a><a href="#cite_note-SeldinGiebisch1997-110">[110]</a> However, its androgen synthesis inhibition is probably clinically insignificant.<a href="#cite_note-pmid9238337-66">[66]</a> Spironolactone has been found in some studies to increase levels of <a href="/wiki/Estradiol" title="Estradiol">estradiol</a>, an <a href="/wiki/Estrogen" title="Estrogen">estrogen</a>, although many other studies have found no changes in estradiol levels.<a href="#cite_note-pmid984618-109">[109]</a><a href="#cite_note-pmid8094898-134">[134]</a> The mechanism of how spironolactone increases estradiol levels is unclear, but it may involve inhibition of the inactivation of estradiol into <a href="/wiki/Estrone" title="Estrone">estrone</a> and enhancement of the peripheral conversion of testosterone into estradiol.<a href="#cite_note-pmid12477487-202">[202]</a><a href="#cite_note-pmid907238-203">[203]</a> It is notable that spironolactone has been found in vitro to act as a weak inhibitor of <a href="/wiki/17%CE%B2-hydroxysteroid_dehydrogenase_2" class="mw-redirect" title="17β-hydroxysteroid dehydrogenase 2">17β-hydroxysteroid dehydrogenase 2</a>, an enzyme that is involved in the conversion of estradiol into estrone.<a href="#cite_note-pmid12570693-204">[204]</a><a href="#cite_note-pmid19601747-205">[205]</a> Increased levels of estradiol with spironolactone may be involved in its preservation of <a href="/wiki/Bone_density" title="Bone density">bone density</a> and in its side effects such as breast tenderness, breast enlargement, and gynecomastia in women and men.<a href="#cite_note-pmid12477487-202">[202]</a><a href="#cite_note-pmid24189467-206">[206]</a><a href="#cite_note-pmid26230882-207">[207]</a> In response to the antimineralocorticoid activity spironolactone, and in an attempt to maintain <a href="/wiki/Homeostasis" title="Homeostasis">homeostasis</a>, the body increases aldosterone production in the <a href="/wiki/Adrenal_cortex" title="Adrenal cortex">adrenal cortex</a>.<a href="#cite_note-Adams2014-208">[208]</a><a href="#cite_note-pmid22836869-209">[209]</a><a href="#cite_note-pmid17035932-210">[210]</a> Some studies have found that levels of <a href="/wiki/Cortisol" title="Cortisol">cortisol</a>, a <a href="/wiki/Glucocorticoid" title="Glucocorticoid">glucocorticoid</a> hormone that is also produced in the adrenal cortex, are increased as well.<a href="#cite_note-pmid22836869-209">[209]</a><a href="#cite_note-pmid17035932-210">[210]</a><a href="#cite_note-pmid27519144-211">[211]</a> Spironolactone “acts at the basolateral side of the upper-distal tubule as well as in the collecting tubule,” and does not have glucocorticoid-like effects at these specific sites; it can sometimes be prescribed as an alternative to glucocorticoids for patients with Glucocorticoid-Remediable Aldosteronism characterized by aldosterone excess,<a href="#cite_note-pmid8144871-141">[141]</a><a href="#cite_note-FalconeHurd2007-212">[212]</a><a href="#cite_note-Hammerstein1990-97">[97]</a><a href="#cite_note-pmid628197-213">[213]</a> In patients “receiving spironolactone, there was a significant positive correlation between the change in cortisol and the change in HbA1c (r = 0.489, P = .003).”<a href="#cite_note-pmid21095280-214">[214]</a> Patients taking spironolactone must be monitored for side effects including dizziness, headache, fatigue, diarrhea, hypertriglyceridemia and elevated liver enzymes.<a href="#cite_note-KuntzKuntz2009-215">[215]</a><a href="#cite_note-MelmedPolonsky2011-216">[216]</a> Other activities of spironolactone may include very weak interactions with the <a href="/wiki/Estrogen_receptor" title="Estrogen receptor">estrogen</a> and <a href="/wiki/Progesterone_receptor" title="Progesterone receptor">progesterone receptors</a> and <a href="/wiki/Agonist" title="Agonist">agonism</a> of the <a href="/wiki/Pregnane_X_receptor" title="Pregnane X receptor">pregnane X receptor</a>.<a href="#cite_note-Hammerstein1990-97">[97]</a><a href="#cite_note-pmid12372848-217">[217]</a> These activities could contribute to the <a href="/wiki/Menstrual_irregularity" class="mw-redirect" title="Menstrual irregularity">menstrual irregularities</a> and <a href="/wiki/Breast" title="Breast">breast</a> side effects of spironolactone and to its <a href="/wiki/Drug_interaction" title="Drug interaction">drug interactions</a>, respectively.<a href="#cite_note-pmid27072668-218">[218]</a><a href="#cite_note-Delyani2000-219">[219]</a><a href="#cite_note-pmid9727070-220">[220]</a> <div class="mw-heading mw-heading3"><h3 id="Pharmacokinetics">Pharmacokinetics</h3>[<a href="/w/index.php?title=Spironolactone&action=edit&section=23" title="Edit section: Pharmacokinetics">edit</a>]</div> The <a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">pharmacokinetics</a> of spironolactone have not been studied well, which is in part because it is an old medication that was developed in the 1950s.<a href="#cite_note-Wilcox2008-135">[135]</a> Nonetheless, much has been elucidated about the pharmacokinetics of spironolactone over the decades.<a href="#cite_note-pmid363379-221">[221]</a><a href="#cite_note-pmid6369882-222">[222]</a><a href="#cite_note-pmid3333882-223">[223]</a><a href="#cite_note-pmid15947888-11">[11]</a><a href="#cite_note-pmid22099505-224">[224]</a><a href="#cite_note-pmid21771637-225">[225]</a><a href="#cite_note-pmid26939027-226">[226]</a><a href="#cite_note-pmid27830348-227">[227]</a> <div class="mw-heading mw-heading4"><h4 id="Absorption">Absorption</h4>[<a href="/w/index.php?title=Spironolactone&action=edit&section=24" title="Edit section: Absorption">edit</a>]</div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Spironolactone_and_metabolite_levels_after_a_single_oral_dose_of_100_mg_spironolactone.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/db/Spironolactone_and_metabolite_levels_after_a_single_oral_dose_of_100_mg_spironolactone.png/400px-Spironolactone_and_metabolite_levels_after_a_single_oral_dose_of_100_mg_spironolactone.png" decoding="async" width="400" height="275" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/db/Spironolactone_and_metabolite_levels_after_a_single_oral_dose_of_100_mg_spironolactone.png/600px-Spironolactone_and_metabolite_levels_after_a_single_oral_dose_of_100_mg_spironolactone.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/db/Spironolactone_and_metabolite_levels_after_a_single_oral_dose_of_100_mg_spironolactone.png/800px-Spironolactone_and_metabolite_levels_after_a_single_oral_dose_of_100_mg_spironolactone.png 2x" data-file-width="1676" data-file-height="1151" /></a><figcaption>Levels of spironolactone and its major active metabolites after a single oral dose of 100 mg spironolactone in humans.<a href="#cite_note-pmid8818057-228">[228]</a></figcaption></figure> The <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> of spironolactone when taken <a href="/wiki/Oral_administration" title="Oral administration">by mouth</a> is 60 to 90%.<a href="#cite_note-pmid15947888-11">[11]</a><a href="#cite_note-pmid18729003-12">[12]</a><a href="#cite_note-CaroneOxberry2017-13">[13]</a> The bioavailability of spironolactone and its metabolites increases significantly (+22–95% increases in levels) when spironolactone is taken with food, although it is uncertain whether this further increases the therapeutic effects of the medication.<a href="#cite_note-DeinumRiksen2015-229">[229]</a><a href="#cite_note-pmid3769384-230">[230]</a><a href="#cite_note-pmid872489-231">[231]</a> The increase in bioavailability is thought to be due to promotion of the gastric dissolution and <a href="/wiki/Absorption_(pharmacokinetics)" class="mw-redirect" title="Absorption (pharmacokinetics)">absorption</a> of spironolactone, as well as due to a decrease of the <a href="/wiki/First-pass_metabolism" class="mw-redirect" title="First-pass metabolism">first-pass metabolism</a>.<a href="#cite_note-DeinumRiksen2015-229">[229]</a><a href="#cite_note-Saini-ChohanHatch2009-232">[232]</a><a href="#cite_note-Al-HadiyaBelal2002-233">[233]</a> The relationship between a single dose of spironolactone and plasma levels of <a href="/wiki/Canrenone" title="Canrenone">canrenone</a>, a major <a href="/wiki/Active_metabolite" title="Active metabolite">active metabolite</a> of spironolactone, has been found to be linear across a dose range of 25 to 200 mg spironolactone.<a href="#cite_note-Wu2012-195">[195]</a> <a href="/wiki/Elimination_(pharmacology)#Steady_state" title="Elimination (pharmacology)">Steady-state concentrations</a> of spironolactone are achieved within 8 to 10 days of treatment initiation.<a href="#cite_note-CancerOrganization2001-186">[186]</a><a href="#cite_note-Elsevier2019-234">[234]</a> Little or no systemic <a href="/wiki/Absorption_(pharmacokinetics)" class="mw-redirect" title="Absorption (pharmacokinetics)">absorption</a> has been observed with topical spironolactone.<a href="#cite_note-pmid3411088-235">[235]</a> <div class="mw-heading mw-heading4"><h4 id="Distribution">Distribution</h4>[<a href="/w/index.php?title=Spironolactone&action=edit&section=25" title="Edit section: Distribution">edit</a>]</div> Spironolactone and its metabolite canrenone are highly <a href="/wiki/Plasma_protein_bound" class="mw-redirect" title="Plasma protein bound">plasma protein bound</a>, with percentages of 88.0% and 99.2%, respectively.<a href="#cite_note-pmid15947888-11">[11]</a><a href="#cite_note-TakamuraMaruyama1997-14">[14]</a> Spironolactone is bound equivalently to <a href="/wiki/Human_serum_albumin" title="Human serum albumin">albumin</a> and <a href="/wiki/Orosomucoid" title="Orosomucoid">α1-acid glycoprotein</a>, while canrenone is bound only to albumin.<a href="#cite_note-pmid15947888-11">[11]</a><a href="#cite_note-TakamuraMaruyama1997-14">[14]</a> Spironolactone and its metabolite <a href="/wiki/7%CE%B1-thiospironolactone" class="mw-redirect" title="7α-thiospironolactone">7α-thiospironolactone</a> show very low or negligible affinity for <a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin">sex hormone-binding globulin</a> (SHBG).<a href="#cite_note-pmid86546-236">[236]</a><a href="#cite_note-pmid7195405-237">[237]</a> In accordance, a study of high-dosage spironolactone treatment found no change in steroid binding capacity related to SHBG or to <a href="/wiki/Corticosteroid-binding_globulin" class="mw-redirect" title="Corticosteroid-binding globulin">corticosteroid-binding globulin</a> (CBG), suggesting that spironolactone does not displace <a href="/wiki/Steroid_hormone" title="Steroid hormone">steroid hormones</a> from their <a href="/wiki/Carrier_protein" class="mw-redirect" title="Carrier protein">carrier proteins</a>.<a href="#cite_note-pmid7189544-238">[238]</a> This is in contradiction with widespread statements that spironolactone increases free estradiol levels by displacing estradiol from SHBG.<a href="#cite_note-Hammerstein1990-97">[97]</a><a href="#cite_note-BlandIII2009-239">[239]</a> Spironolactone appears to cross the <a href="/wiki/Blood%E2%80%93brain_barrier" title="Blood–brain barrier">blood–brain barrier</a>.<a href="#cite_note-pmid25376974-240">[240]</a><a href="#cite_note-pmid22351473-241">[241]</a> <div class="mw-heading mw-heading4"><h4 id="Metabolism">Metabolism</h4>[<a href="/w/index.php?title=Spironolactone&action=edit&section=26" title="Edit section: Metabolism">edit</a>]</div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Spironolactone_metabolism.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4f/Spironolactone_metabolism.png/400px-Spironolactone_metabolism.png" decoding="async" width="400" height="327" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4f/Spironolactone_metabolism.png/600px-Spironolactone_metabolism.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4f/Spironolactone_metabolism.png/800px-Spironolactone_metabolism.png 2x" data-file-width="2570" data-file-height="2100" /></a><figcaption>Spironolactone <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> in humans.<a href="#cite_note-pmid1629288-242">[242]</a> <a href="/wiki/Canrenone" title="Canrenone">Canrenone</a> may be further <a href="/wiki/Redox" title="Redox">reduced</a> (into di-, tetra-, and hexahydrogenated metabolites), <a href="/wiki/Hydroxylation" title="Hydroxylation">hydroxylated</a>, and <a href="/wiki/Conjugation_(biochemistry)" class="mw-redirect" title="Conjugation (biochemistry)">conjugated</a> (e.g., <a href="/wiki/Glucuronidation" title="Glucuronidation">glucuronidated</a>).<a href="#cite_note-pmid1629288-242">[242]</a></figcaption></figure> Spironolactone is rapidly and extensively <a href="/wiki/Metabolism" title="Metabolism">metabolized</a> in the <a href="/wiki/Liver" title="Liver">liver</a> upon <a href="/wiki/Oral_administration" title="Oral administration">oral administration</a> and has a very short <a href="/wiki/Biological_half-life" title="Biological half-life">terminal half-life</a> of 1.4 hours.<a href="#cite_note-pmid15947888-11">[11]</a><a href="#cite_note-pmid18729003-12">[12]</a> The major <a href="/wiki/Metabolite" title="Metabolite">metabolites</a> of spironolactone are <a href="/wiki/7%CE%B1-thiomethylspironolactone" class="mw-redirect" title="7α-thiomethylspironolactone">7α-thiomethylspironolactone</a> (7α-TMS), <a href="/wiki/6%CE%B2-hydroxy-7%CE%B1-thiomethylspironolactone" class="mw-redirect" title="6β-hydroxy-7α-thiomethylspironolactone">6β-hydroxy-7α-thiomethylspironolactone</a> (6β-OH-7α-TMS), and <a href="/wiki/Canrenone" title="Canrenone">canrenone</a> (7α-desthioacetyl-δ6-spironolactone).<a href="#cite_note-pmid15947888-11">[11]</a><a href="#cite_note-pmid18729003-12">[12]</a><a href="#cite_note-AgustiBourgeois2013-185">[185]</a> These metabolites have much longer elimination half-lives than spironolactone of 13.8 hours, 15.0 hours, and 16.5 hours, respectively, and are responsible for the therapeutic effects of the medication.<a href="#cite_note-pmid15947888-11">[11]</a><a href="#cite_note-pmid18729003-12">[12]</a> As such, spironolactone is a <a href="/wiki/Prodrug" title="Prodrug">prodrug</a>.<a href="#cite_note-Oxford2003-243">[243]</a> The 7α-thiomethylated metabolites of spironolactone were not known for many years and it was originally thought that canrenone was the major active metabolite of the medication, but subsequent research identified 7α-TMS as the major metabolite.<a href="#cite_note-pmid15947888-11">[11]</a><a href="#cite_note-AgustiBourgeois2013-185">[185]</a><a href="#cite_note-CancerOrganization2001-186">[186]</a> Other known but more minor metabolites of spironolactone include <a href="/wiki/7%CE%B1-thiospironolactone" class="mw-redirect" title="7α-thiospironolactone">7α-thiospironolactone</a> (7α-TS), which is an important <a href="/wiki/Metabolic_intermediate" title="Metabolic intermediate">intermediate</a> to the major metabolites of spironolactone,<a href="#cite_note-Parkinson2001-17">[17]</a> as well as the 7α-methyl ethyl ester of spironolactone and the 6β-hydroxy-7α-methyl ethyl ester of spironolactone.<a href="#cite_note-SzaszBudvari-Barany1990-15">[15]</a> Spironolactone is <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolyzed</a> or <a href="/wiki/Acetylation" title="Acetylation">deacetylated</a> at the <a href="/wiki/Thioester" title="Thioester">thioester</a> of the C7α position into 7α-TS by <a href="/wiki/Carboxylesterase" title="Carboxylesterase">carboxylesterases</a>.<a href="#cite_note-Parkinson2001-17">[17]</a><a href="#cite_note-AnzenbacherZanger2012-244">[244]</a> Following formation of 7α-TS, it is S-<a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxygenated</a> by <a href="/wiki/Flavin-containing_monooxygenase" title="Flavin-containing monooxygenase">flavin-containing monooxygenases</a> to form an <a href="/wiki/Electrophilic" class="mw-redirect" title="Electrophilic">electrophilic</a> <a href="/wiki/Sulfenic_acid" title="Sulfenic acid">sulfenic acid</a> <a href="/wiki/Metabolite" title="Metabolite">metabolite</a>.<a href="#cite_note-Parkinson2001-17">[17]</a> This metabolite is involved in the CYP450 inhibition of spironolactone, and also binds <a href="/wiki/Covalent_bond" title="Covalent bond">covalently</a> to other <a href="/wiki/Protein" title="Protein">proteins</a>.<a href="#cite_note-Parkinson2001-17">[17]</a> 7α-TS is also S-<a href="/wiki/Methylation" title="Methylation">methylated</a> into 7α-TMS, a transformation catalyzed by <a href="/wiki/Thiol_S-methyltransferase" title="Thiol S-methyltransferase">thiol S-methyltransferase</a>.<a href="#cite_note-Parkinson2001-17">[17]</a> Unlike the related medication <a href="/wiki/Eplerenone" title="Eplerenone">eplerenone</a>, spironolactone is said to not be metabolized by <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a>.<a href="#cite_note-SmithPh.D.2014-245">[245]</a> However, hepatic CYP3A4 is likely responsible for the 6β-<a href="/wiki/Hydroxylation" title="Hydroxylation">hydroxylation</a> of 7α-TMS into 6β-OH-7α-TMS.<a href="#cite_note-Klaassen2007-18">[18]</a><a href="#cite_note-Montellano2015-246">[246]</a> 7α-TMS may also be <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxylated</a> at the C3α and C3β positions.<a href="#cite_note-pmid7895608-19">[19]</a> Spironolactone is <a href="/wiki/Dethioacetylated" class="mw-redirect" title="Dethioacetylated">dethioacetylated</a> into canrenone.<a href="#cite_note-BlackElliott2006-20">[20]</a> Finally, the C17 γ-<a href="/wiki/Lactone" title="Lactone">lactone</a> <a href="/wiki/Ring_(chemistry)" title="Ring (chemistry)">ring</a> of spironolactone is hydrolyzed by the <a href="/wiki/Paraoxonase" title="Paraoxonase">paraoxonase</a> <a href="/wiki/PON3" title="PON3">PON3</a>.<a href="#cite_note-pmid14579013-21">[21]</a><a href="#cite_note-AcademicPress2012-247">[247]</a> It was originally thought to be hydrolyzed by PON1, but this was due to contamination with PON3.<a href="#cite_note-pmid14579013-21">[21]</a> <table class="wikitable sortable mw-collapsible mw-collapsed" style="margin-left: auto; margin-right: auto; border: none;"> <caption class="nowrap"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Pharmacokinetics_of_100_mg_per_day_spironolactone_and_its_metabolites" title="Template:Pharmacokinetics of 100 mg per day spironolactone and its metabolites"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Pharmacokinetics_of_100_mg_per_day_spironolactone_and_its_metabolites" title="Template talk:Pharmacokinetics of 100 mg per day spironolactone and its metabolites"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Pharmacokinetics_of_100_mg_per_day_spironolactone_and_its_metabolites" title="Special:EditPage/Template:Pharmacokinetics of 100 mg per day spironolactone and its metabolites"><abbr title="Edit this template">e</abbr></a></li></ul></div> Pharmacokinetics of 100 mg/day spironolactone and its metabolites </caption> <tbody><tr> <th>Compound</th> <th><a href="/wiki/Peak_concentrations" class="mw-redirect" title="Peak concentrations"><abbr title="Peak concentrations">Cmax</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 Peak concentrations (day 1)</th> <th><a href="/wiki/Peak_concentrations" class="mw-redirect" title="Peak concentrations"><abbr title="Peak concentrations">Cmax</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 Peak concentrations (day 15)</th> <th><a href="/wiki/Area-under-the-curve_concentrations" class="mw-redirect" title="Area-under-the-curve concentrations"><abbr title="Area-under-the-curve concentrations">AUC</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 Area-under-the-curve concentrations (day 15)</th> <th><a href="/wiki/Elimination_half-life" class="mw-redirect" title="Elimination half-life"><abbr title="Elimination half-life">t1/2</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 Elimination half-life </th></tr> <tr> <td>Spironolactone</td> <td>72 ng/mL (173 nmol/L)</td> <td>80 ng/mL (192 nmol/L)</td> <td>231 ng•hour/mL (555 nmol•hour/L)</td> <td>1.4 hours </td></tr> <tr> <td><a href="/wiki/Canrenone" title="Canrenone">Canrenone</a></td> <td>155 ng/mL (455 nmol/L)</td> <td>181 ng/mL (532 nmol/L)</td> <td>2,173 ng•hour/mL (6,382 nmol•hour/L)</td> <td>16.5 hours </td></tr> <tr> <td><a href="/wiki/7%CE%B1-Thiomethylspironolactone" title="7α-Thiomethylspironolactone"><abbr title="7α-Thiomethylspironolactone">7α-TMS</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 7α-Thiomethylspironolactone</td> <td>359 ng/mL (924 nmol/L)</td> <td>391 ng/mL (1,006 nmol/L)</td> <td>2,804 ng•hour/mL (7,216 nmol•hour/L)</td> <td>13.8 hours </td></tr> <tr> <td><a href="/wiki/6%CE%B2-Hydroxy-7%CE%B1-thiomethylspironolactone" title="6β-Hydroxy-7α-thiomethylspironolactone"><abbr title="6β-Hydroxy-7α-thiomethylspironolactone">6β-OH-7α-TMS</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 6β-Hydroxy-7α-thiomethylspironolactone</td> <td>101 ng/mL (250 nmol/L)</td> <td>125 ng/mL (309 nmol/L)</td> <td>1,727 ng•hour/mL (4,269 nmol•hour/L)</td> <td>15.0 hours </td></tr> <tr class="sortbottom"> <td colspan="5" style="width: 1px; background-color:#eaecf0; text-align: center;">Sources: See template. </td></tr></tbody></table> <div class="mw-heading mw-heading4"><h4 id="Elimination">Elimination</h4>[<a href="/w/index.php?title=Spironolactone&action=edit&section=27" title="Edit section: Elimination">edit</a>]</div> The majority of spironolactone is eliminated by the <a href="/wiki/Kidney" title="Kidney">kidneys</a>, while minimal amounts are handled by <a href="/wiki/Bile" title="Bile">biliary</a> excretion.<a href="#cite_note-Brittain2002-248">[248]</a> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2>[<a href="/w/index.php?title=Spironolactone&action=edit&section=28" title="Edit section: Chemistry">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Spirolactone" title="Spirolactone">Spirolactone</a> and <a href="/wiki/List_of_steroidal_antiandrogens#Spirolactone_derivatives" title="List of steroidal antiandrogens">List of steroidal antiandrogens § Spirolactone derivatives</a></div> Spironolactone, also known as 7α-acetylthiospirolactone, is a <a href="/wiki/Steroid" title="Steroid">steroidal</a> <a href="/wiki/17%CE%B1-spirolactone" class="mw-redirect" title="17α-spirolactone">17α-spirolactone</a>, or more simply a spirolactone.<a href="#cite_note-pmid28634268-107">[107]</a> It can most appropriately be conceptualized as a <a href="/wiki/Chemical_derivative" class="mw-redirect" title="Chemical derivative">derivative</a> of <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a>,<a href="#cite_note-pmid15134800-133">[133]</a><a href="#cite_note-JamesonGroot2010-249">[249]</a><a href="#cite_note-Elsevier2019-234">[234]</a> itself also a potent antimineralocorticoid, in which a <a href="/wiki/Hydroxyl_group" class="mw-redirect" title="Hydroxyl group">hydroxyl group</a> has been <a href="/wiki/Substituent" title="Substituent">substituted</a> at the C17α position (as in <a href="/wiki/17%CE%B1-hydroxyprogesterone" class="mw-redirect" title="17α-hydroxyprogesterone">17α-hydroxyprogesterone</a>), the <a href="/wiki/Acetyl_group" title="Acetyl group">acetyl group</a> at the C17β position has been <a href="/wiki/Cyclic_compound" title="Cyclic compound">cyclized</a> with the C17α hydroxyl group to form a <a href="/wiki/Spiro_compound" title="Spiro compound">spiro</a> 21-<a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a> γ-<a href="/wiki/Lactone" title="Lactone">lactone</a> <a href="/wiki/Ring_(chemistry)" title="Ring (chemistry)">ring</a>, and an acetyl<a href="/wiki/Thio-" title="Thio-">thio</a> group has been substituted in at the C7α position.<a href="#cite_note-Elks2014-250">[250]</a><a href="#cite_note-PubChem-251">[251]</a><a href="#cite_note-ChemSpider-252">[252]</a> These <a href="/wiki/Structural_modification" class="mw-redirect" title="Structural modification">structural modifications</a> of progesterone confer increased <a href="/wiki/Oral_administration" title="Oral administration">oral</a> <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> and <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potency</a>,<a href="#cite_note-pmid8616985-253">[253]</a> potent antiandrogenic activity, and strongly reduced progestogenic activity.<a href="#cite_note-pmid16101407-254">[254]</a> The C7α substitution is likely responsible for or involved in the antiandrogenic activity of spironolactone, as <a href="/wiki/7%CE%B1-thioprogesterone" class="mw-redirect" title="7α-thioprogesterone">7α-thioprogesterone</a> (SC-8365), unlike progesterone,<a href="#cite_note-pmid16112947-255">[255]</a> is an antiandrogen with similar affinity to the AR as that of spironolactone.<a href="#cite_note-pmid263288-256">[256]</a> In addition, the C7α substitution appears to be responsible for the loss of progestogenic activity and good oral bioavailability of spironolactone, as <a href="/wiki/SC-5233" title="SC-5233">SC-5233</a>, the analogue of spironolactone without a C7α substitution, has potent progestogenic activity but very poor oral bioavailability similarly to progesterone.<a href="#cite_note-pmid16112947-255">[255]</a><a href="#cite_note-pmid13601900-257">[257]</a><a href="#cite_note-Butterworth1961-258">[258]</a> <div class="mw-heading mw-heading3"><h3 id="Names">Names</h3>[<a href="/w/index.php?title=Spironolactone&action=edit&section=29" title="Edit section: Names">edit</a>]</div> Spironolactone is also known by the following equivalent chemical names:<a href="#cite_note-Elks2014-250">[250]</a><a href="#cite_note-PubChem-251">[251]</a><a href="#cite_note-ChemSpider-252">[252]</a> <ul><li>7α-Acetylthio-17α-hydroxy-3-oxopregn-4-ene-21-carboxylic acid γ-lactone</li> <li>7α-Acetylthio-3-oxo-17α-pregn-4-ene-21,17β-carbolactone</li> <li>3-(3-Oxo-7α-acetylthio-17β-hydroxyandrost-4-en-17α-yl)propionic acid lactone</li> <li>7α-Acetylthio-17α-(2-carboxyethyl)androst-4-en-17β-ol-3-one γ-lactone</li> <li>7α-Acetylthio-17α-(2-carboxyethyl)testosterone γ-lactone</li></ul> <div class="mw-heading mw-heading3"><h3 id="Analogues">Analogues</h3>[<a href="/w/index.php?title=Spironolactone&action=edit&section=30" title="Edit section: Analogues">edit</a>]</div> <table role="presentation" cellpadding="0" style="border-spacing:0; clear:right; float:right;"> <tbody><tr> <td><div class="thumb tright"> <div class="thumbinner" style="width:552px;"> <div style="clear: both; font-weight: bold; font-size: 106.4%; text-align: center; background-color: aliceblue;margin-bottom:3px;"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Spirolactone_structures" title="Template:Spirolactone structures"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Spirolactone_structures" title="Template talk:Spirolactone structures"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Spirolactone_structures" title="Special:EditPage/Template:Spirolactone structures"><abbr title="Edit this template">e</abbr></a></li></ul></div> Chemical structures of <a href="/wiki/Spirolactone" title="Spirolactone">spirolactones</a></div> <div style="position:relative; width:550px; height:351px; overflow:hidden; border:solid #ccc 1px; background-color:white;"> <div style="left:0px; top:0px; width:550px; position:absolute"> <img alt="Spirolactone structures" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Spirolactone_structures.png/550px-Spirolactone_structures.png" decoding="async" width="550" height="347" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Spirolactone_structures.png/825px-Spirolactone_structures.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Spirolactone_structures.png/1100px-Spirolactone_structures.png 2x" data-file-width="2600" data-file-height="1640" /> </div> <div style="text-align:center; font-size:14px; line-height:110%"> <div style="background-color:transparent; color:black"><div id="annotation_53x134" style="position:absolute; left:53px; top:134px; line-height:110%;"><a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">Progesterone</a></div> <div id="annotation_235x134" style="position:absolute; left:235px; top:134px; line-height:110%;"><a href="/wiki/SC-5233" title="SC-5233">Spirolactone</a></div> <div id="annotation_420x134" style="position:absolute; left:420px; top:134px; line-height:110%;"><a href="/wiki/Canrenone" title="Canrenone">Canrenone</a></div> <div id="annotation_53x322" style="position:absolute; left:53px; top:322px; line-height:110%;">Spironolactone</div> <div id="annotation_235x322" style="position:absolute; left:235px; top:322px; line-height:110%;"><a href="/wiki/Drospirenone" title="Drospirenone">Drospirenone</a></div> <div id="annotation_420x322" style="position:absolute; left:420px; top:322px; line-height:110%;"><a href="/wiki/Spirorenone" title="Spirorenone">Spirorenone</a></div></div> </div> </div> <div class="thumbcaption" style="clear:left"><div style="float:left;margin-right:0.5em"><img alt="The image above contains clickable links" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/18px-Interactive_icon.svg.png" decoding="async" width="18" height="27" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/27px-Interactive_icon.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/36px-Interactive_icon.svg.png 2x" data-file-width="133" data-file-height="200" /></div><a href="/wiki/Chemical_structure" title="Chemical structure">Chemical structures</a> of <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a> and <a href="/wiki/Spirolactone" title="Spirolactone">spirolactones</a> (steroid-17α-spirolactones).</div> </div> </div> </td></tr></tbody></table> Spironolactone is closely related structurally to other clinically used spirolactones such as <a href="/wiki/Canrenone" title="Canrenone">canrenone</a>, <a href="/wiki/Potassium_canrenoate" title="Potassium canrenoate">potassium canrenoate</a>, <a href="/wiki/Drospirenone" title="Drospirenone">drospirenone</a>, and <a href="/wiki/Eplerenone" title="Eplerenone">eplerenone</a>, as well as to the never-marketed spirolactones <a href="/wiki/SC-5233" title="SC-5233">SC-5233</a> (6,7-dihydrocanrenone; 7α-desthioacetylspironolactone), <a href="/wiki/SC-8109" title="SC-8109">SC-8109</a> (19-nor-6,7-dihydrocanrenone), <a href="/wiki/Spiroxasone" title="Spiroxasone">spiroxasone</a>, <a href="/wiki/Prorenone" title="Prorenone">prorenone</a> (SC-23133), <a href="/wiki/Mexrenone" title="Mexrenone">mexrenone</a> (SC-25152, ZK-32055), <a href="/wiki/Dicirenone" title="Dicirenone">dicirenone</a> (SC-26304), <a href="/wiki/Spirorenone" title="Spirorenone">spirorenone</a> (ZK-35973), and <a href="/wiki/Mespirenone" title="Mespirenone">mespirenone</a> (ZK-94679).<a href="#cite_note-pmid28634268-107">[107]</a> <div class="mw-heading mw-heading3"><h3 id="Synthesis">Synthesis</h3>[<a href="/w/index.php?title=Spironolactone&action=edit&section=31" title="Edit section: Synthesis">edit</a>]</div> <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">Chemical syntheses</a> of spironolactone and its <a href="/wiki/Structural_analog" title="Structural analog">analogues</a> and <a href="/wiki/Chemical_derivative" class="mw-redirect" title="Chemical derivative">derivatives</a> have been described and reviewed.<a href="#cite_note-pmid28041953-259">[259]</a> <div class="mw-heading mw-heading2"><h2 id="History">History</h2>[<a href="/w/index.php?title=Spironolactone&action=edit&section=32" title="Edit section: History">edit</a>]</div> The <a href="/wiki/Natriuretic" class="mw-redirect" title="Natriuretic">natriuretic</a> effects of <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a> were demonstrated in 1955, and the development of spironolactone as a <a href="/wiki/Synthetic_compound" class="mw-redirect" title="Synthetic compound">synthetic</a> antimineralocorticoid <a href="/wiki/Structural_analog" title="Structural analog">analogue</a> of progesterone shortly followed this.<a href="#cite_note-pmid15134800-133">[133]</a><a href="#cite_note-JamesonGroot2010-249">[249]</a><a href="#cite_note-pmid13486053-260">[260]</a><a href="#cite_note-pmid13486054-261">[261]</a> Spironolactone was first <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">synthesized</a> in 1957,<a href="#cite_note-OttowWeinmann2008-28">[28]</a><a href="#cite_note-pmid13486053-260">[260]</a><a href="#cite_note-pmid13486054-261">[261]</a> was <a href="/wiki/Patent" title="Patent">patented</a> between 1958 and 1961,<a href="#cite_note-EngelKleemann2014-262">[262]</a><a href="#cite_note-LandauAchilladelis1999-263">[263]</a> and was first marketed, as an antimineralocorticoid, in 1959.<a href="#cite_note-Jugdutt2014-264">[264]</a><a href="#cite_note-Wermuth2011-265">[265]</a> Gynecomastia was first reported with spironolactone in 1962,<a href="#cite_note-pmid28634268-107">[107]</a><a href="#cite_note-Smith1962-266">[266]</a> and the antiandrogenic activity of the medication was first described in 1969.<a href="#cite_note-pmid5344274-267">[267]</a> This shortly followed the discovery in 1967 that gynecomastia is an important and major side effect of AR antagonists.<a href="#cite_note-pmid148431-268">[268]</a><a href="#cite_note-NeillJohansson1968-269">[269]</a> Spironolactone was first studied in the treatment of hirsutism in women in 1978.<a href="#cite_note-pmid6205409-270">[270]</a><a href="#cite_note-pmid27450358-176">[176]</a><a href="#cite_note-pmid717935-271">[271]</a><a href="#cite_note-pmid488407-272">[272]</a><a href="#cite_note-pmid7410528-273">[273]</a> It has since become the most widely used antiandrogen for dermatological indications in women in the United States.<a href="#cite_note-WakelinMaibach2002-103">[103]</a><a href="#cite_note-Curtis2014-274">[274]</a><a href="#cite_note-ShahBhathena2004-275">[275]</a><a href="#cite_note-Hillard2013-276">[276]</a> Spironolactone was first studied as an antiandrogen in transgender women in 1986, and has since become widely adopted for this purpose as well, particularly in the United States where cyproterone acetate is not available.<a href="#cite_note-DahlFeldman2006-277">[277]</a><a href="#cite_note-PriorVigna1986-278">[278]</a><a href="#cite_note-FisherMaggi2015-279">[279]</a> Early oral spironolactone tablets showed poor absorption.<a href="#cite_note-Dorfman2016-280">[280]</a> The formulation was eventually changed to a <a href="/wiki/Micronization" title="Micronization">micronized</a> formulation with <a href="/wiki/Particle_size" title="Particle size">particle sizes</a> of less than 50 μg, which resulted in approximately 4-fold increased potency.<a href="#cite_note-Dorfman2016-280">[280]</a><a href="#cite_note-GlázVecsei2017-281">[281]</a> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2>[<a href="/w/index.php?title=Spironolactone&action=edit&section=33" title="Edit section: Society and culture">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Generic_names">Generic names</h3>[<a href="/w/index.php?title=Spironolactone&action=edit&section=34" title="Edit section: Generic names">edit</a>]</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Spironolactone_for_veterinary_use.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e4/Spironolactone_for_veterinary_use.jpg/220px-Spironolactone_for_veterinary_use.jpg" decoding="async" width="220" height="196" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e4/Spironolactone_for_veterinary_use.jpg/330px-Spironolactone_for_veterinary_use.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e4/Spironolactone_for_veterinary_use.jpg/440px-Spironolactone_for_veterinary_use.jpg 2x" data-file-width="1946" data-file-height="1732" /></a><figcaption>Generic spironolactone for veterinary use</figcaption></figure> The English, French, and <a href="/wiki/Generic_drug" title="Generic drug">generic name</a> of the medication is spironolactone and this is 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, <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, <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, <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, <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, 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.<a href="#cite_note-IndexNominum2000-105">[105]</a><a href="#cite_note-Drugs.com-106">[106]</a><a href="#cite_note-Elks2014-250">[250]</a><a href="#cite_note-MortonHall1999-282">[282]</a> Its name is spironolactonum in Latin, Spironolacton in German, espironolactona in Spanish and Portuguese, and spironolattone in Italian (which is also its <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).<a href="#cite_note-IndexNominum2000-105">[105]</a><a href="#cite_note-Drugs.com-106">[106]</a><a href="#cite_note-MortonHall1999-282">[282]</a> Spironolactone is also known by its developmental code names SC-9420 and NSC-150339.<a href="#cite_note-IndexNominum2000-105">[105]</a><a href="#cite_note-Drugs.com-106">[106]</a><a href="#cite_note-Elks2014-250">[250]</a> <div class="mw-heading mw-heading3"><h3 id="Brand_names">Brand names</h3>[<a href="/w/index.php?title=Spironolactone&action=edit&section=35" title="Edit section: Brand names">edit</a>]</div> Spironolactone is marketed under a various brand names throughout the world.<a href="#cite_note-IndexNominum2000-105">[105]</a><a href="#cite_note-Drugs.com-106">[106]</a> The original brand name of spironolactone is Aldactone.<a href="#cite_note-IndexNominum2000-105">[105]</a><a href="#cite_note-Drugs.com-106">[106]</a> Other brand names include Aldactone-A, Berlactone, CaroSpir, Espironolactona, Espironolactona Genfar, Novo-Spiroton, Prilactone (<a href="/wiki/Veterinary_medicine" title="Veterinary medicine">veterinary</a>), Spiractin, Spiridon, Spirix, Spiroctan, Spiroderm (discontinued),<a href="#cite_note-FARIDDiamanti-Kandarakis2009-5">[5]</a> Spirogamma, Spirohexal, Spirolon, Spirolone, Spiron, Spironolactone Actavis, Spironolactone Orion, Spironolactone Teva, Spirotone, Tempora (veterinary), Uractone, Uractonum, Verospiron, and Vivitar.<a href="#cite_note-IndexNominum2000-105">[105]</a><a href="#cite_note-Drugs.com-106">[106]</a> Spironolactone is also formulated in combination with a variety of other medications, including with <a href="/wiki/Hydrochlorothiazide" title="Hydrochlorothiazide">hydrochlorothiazide</a> as Aldactazide, with <a href="/wiki/Hydroflumethiazide" title="Hydroflumethiazide">hydroflumethiazide</a> as Aldactide, Lasilacton, Lasilactone, and Spiromide, with <a href="/wiki/Altizide" title="Altizide">altizide</a> as Aldactacine and Aldactazine, with <a href="/wiki/Furosemide" title="Furosemide">furosemide</a> as Fruselac, with <a href="/wiki/Benazepril" title="Benazepril">benazepril</a> as Cardalis (veterinary), with <a href="/wiki/Metolazone" title="Metolazone">metolazone</a> as Metolactone, with <a href="/wiki/Bendroflumethiazide" title="Bendroflumethiazide">bendroflumethiazide</a> as Sali-Aldopur, and with <a href="/wiki/Torasemide" title="Torasemide">torasemide</a> as Dytor Plus, Torlactone, and Zator Plus.<a href="#cite_note-Drugs.com-106">[106]</a> <div class="mw-heading mw-heading3"><h3 id="Availability">Availability</h3>[<a href="/w/index.php?title=Spironolactone&action=edit&section=36" title="Edit section: Availability">edit</a>]</div> Spironolactone is marketed throughout the world.<a href="#cite_note-IndexNominum2000-105">[105]</a><a href="#cite_note-Drugs.com-106">[106]</a> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2>[<a href="/w/index.php?title=Spironolactone&action=edit&section=37" title="Edit section: Research">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Prostate_conditions">Prostate conditions</h3>[<a href="/w/index.php?title=Spironolactone&action=edit&section=38" title="Edit section: Prostate conditions">edit</a>]</div> Spironolactone has been studied at a high dosage in the treatment of <a href="/wiki/Benign_prostatic_hyperplasia" title="Benign prostatic hyperplasia">benign prostatic hyperplasia</a> (BPH; enlarged prostate).<a href="#cite_note-Springer2012-283">[283]</a><a href="#cite_note-pmid1702565-284">[284]</a><a href="#cite_note-pmid4104441-285">[285]</a> It was found to be better than placebo in terms of symptom relief following three months of treatment.<a href="#cite_note-Springer2012-283">[283]</a><a href="#cite_note-pmid1702565-284">[284]</a> However, this was not maintained after six months of treatment, by which point the improvements had largely disappeared.<a href="#cite_note-Springer2012-283">[283]</a><a href="#cite_note-pmid1702565-284">[284]</a><a href="#cite_note-pmid4104441-285">[285]</a> Moreover, no difference was observed between spironolactone and placebo with regard to volume of residual urine or prostate size.<a href="#cite_note-Springer2012-283">[283]</a><a href="#cite_note-pmid1702565-284">[284]</a> Gynecomastia was observed in about 5% of people.<a href="#cite_note-pmid1702565-284">[284]</a> On the basis of these results, it has been said that spironolactone has no place in the treatment of BPH.<a href="#cite_note-pmid1702565-284">[284]</a> Spironolactone has been studied and used limitedly in the treatment of <a href="/wiki/Prostate_cancer" title="Prostate cancer">prostate cancer</a>.<a href="#cite_note-pmid29603164-286">[286]</a><a href="#cite_note-pmid3540320-287">[287]</a><a href="#cite_note-EndouHosoyamada1995-37">[37]</a> <div class="mw-heading mw-heading3"><h3 id="Epstein–Barr_virus">Epstein–Barr virus</h3>[<a href="/w/index.php?title=Spironolactone&action=edit&section=39" title="Edit section: Epstein–Barr virus">edit</a>]</div> Spironolactone has been found to block <a href="/wiki/Epstein%E2%80%93Barr_virus" title="Epstein–Barr virus">Epstein–Barr virus</a> (EBV) production and that of other <a href="/wiki/Human_herpesviruses" class="mw-redirect" title="Human herpesviruses">human herpesviruses</a> by inhibiting the function of an EBV protein SM, which is essential for infectious virus production.<a href="#cite_note-Verma2016-288">[288]</a> This effect of spironolactone was determined to be independent of its antimineralocorticoid actions.<a href="#cite_note-Verma2016-288">[288]</a> <div class="mw-heading mw-heading3"><h3 id="Other_conditions">Other conditions</h3>[<a href="/w/index.php?title=Spironolactone&action=edit&section=40" title="Edit section: Other conditions">edit</a>]</div> Spironolactone has been studied in the treatment of <a href="/wiki/Rosacea" title="Rosacea">rosacea</a> in both males and females.<a href="#cite_note-pmid15389184-289">[289]</a><a href="#cite_note-GiurcăneanuMarinescu2016-290">[290]</a><a href="#cite_note-Wollina2014-291">[291]</a><a href="#cite_note-pmid9557251-74">[74]</a><a href="#cite_note-pmid23594595-292">[292]</a> Spironolactone has been studied in <a href="/wiki/Fibromyalgia" title="Fibromyalgia">fibromyalgia</a> in women.<a href="#cite_note-WernzeHerdegen2014-293">[293]</a><a href="#cite_note-Kalso2014-294">[294]</a> It has also been studied in <a href="/wiki/Bulimia_nervosa" title="Bulimia nervosa">bulimia nervosa</a> in women, but was not found to be effective.<a href="#cite_note-pmid22946772-295">[295]</a> <div class="mw-heading mw-heading2"><h2 id="References">References</h2>[<a href="/w/index.php?title=Spironolactone&action=edit&section=41" title="Edit section: References">edit</a>]</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-LoughlinGenerali2006-1"><a href="#cite_ref-LoughlinGenerali2006_1-0">^</a> <style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFLoughlinGenerali2006" class="citation book cs1">Loughlin KR, Generali JA (2006). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=fhEFkBxEtH8C&pg=PA131">The Guide to Off-label Prescription Drugs: New Uses for FDA-approved Prescription Drugs</a>. 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Current Opinion in Investigational Drugs. 9 (9): 963–9. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2967484">2967484</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/18729003">18729003</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Current+Opinion+in+Investigational+Drugs&rft.atitle=Mineralocorticoid+receptor+antagonists+and+endothelial+function&rft.volume=9&rft.issue=9&rft.pages=963-9&rft.date=2008-09&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2967484%23id-name%3DPMC&rft_id=info%3Apmid%2F18729003&rft.aulast=Maron&rft.aufirst=BA&rft.au=Leopold%2C+JA&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2967484&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-CaroneOxberry2017-13">^ <a href="#cite_ref-CaroneOxberry2017_13-0">a</a> <a href="#cite_ref-CaroneOxberry2017_13-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCaroneOxberryTwycrossCharlesworth2017" class="citation journal cs1">Carone L, Oxberry SG, Twycross R, Charlesworth S, Mihalyo M, Wilcock A (February 2017). <a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.jpainsymman.2016.12.320">"Spironolactone"</a>. 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Frontiers in Endocrinology. 14: 1184024. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3389%2Ffendo.2023.1184024">10.3389/fendo.2023.1184024</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10355117">10355117</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/37476490">37476490</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Frontiers+in+Endocrinology&rft.atitle=Review+of+adult+gender+transition+medications%3A+mechanisms%2C+efficacy+measures%2C+and+pharmacogenomic+considerations&rft.volume=14&rft.pages=1184024&rft.date=2023&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC10355117%23id-name%3DPMC&rft_id=info%3Apmid%2F37476490&rft_id=info%3Adoi%2F10.3389%2Ffendo.2023.1184024&rft.aulast=Sehgal&rft.aufirst=I&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC10355117&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-ineffectiveness_in_HRT-26">^ <a href="#cite_ref-ineffectiveness_in_HRT_26-0">a</a> <a href="#cite_ref-ineffectiveness_in_HRT_26-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCosgrove2018" class="citation web cs1">Cosgrove B (January 2018). <a rel="nofollow" class="external text" href="https://moderntranshormones.com/2018/01/01/whats-wrong-with-spironolactone/">"The Case Against Spironolactone"</a>. 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JP Medical Ltd. pp. 47–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-93-5090-723-8" title="Special:BookSources/978-93-5090-723-8"><bdi>978-93-5090-723-8</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20221007092257/https://books.google.com/books?id=k8bUAgAAQBAJ&pg=PA47">Archived</a> from the original on 7 October 2022. 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The Cochrane Database of Systematic Reviews. 2016 (5): CD007628. <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.CD007628.pub4">10.1002/14651858.CD007628.pub4</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6457957">6457957</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/27225981">27225981</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=Interventions+for+female+pattern+hair+loss&rft.volume=2016&rft.issue=5&rft.pages=CD007628&rft.date=2016-05&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6457957%23id-name%3DPMC&rft_id=info%3Apmid%2F27225981&rft_id=info%3Adoi%2F10.1002%2F14651858.CD007628.pub4&rft.aulast=van+Zuuren&rft.aufirst=EJ&rft.au=Fedorowicz%2C+Z&rft.au=Schoones%2C+J&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6457957&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-pmid19370553-96"><a href="#cite_ref-pmid19370553_96-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBrownFarquharLeeToomath2009" class="citation journal cs1">Brown J, Farquhar C, Lee O, Toomath R, Jepson RG (April 2009). 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Retrieved 1 December 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Spironolactone&rft_id=https%3A%2F%2Fwww.drugs.com%2Finternational%2Fspironolactone.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-pmid28634268-107">^ <a href="#cite_ref-pmid28634268_107-0">a</a> <a href="#cite_ref-pmid28634268_107-1">b</a> <a href="#cite_ref-pmid28634268_107-2">c</a> <a href="#cite_ref-pmid28634268_107-3">d</a> <a href="#cite_ref-pmid28634268_107-4">e</a> <a href="#cite_ref-pmid28634268_107-5">f</a> <a href="#cite_ref-pmid28634268_107-6">g</a> <a href="#cite_ref-pmid28634268_107-7">h</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKolkhofBärfacker2017" class="citation journal cs1">Kolkhof P, Bärfacker L (July 2017). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5488394">"30 YEARS OF THE MINERALOCORTICOID RECEPTOR: Mineralocorticoid receptor antagonists: 60 years of research and development"</a>. The Journal of Endocrinology. 234 (1): T125–T140. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1530%2FJOE-16-0600">10.1530/JOE-16-0600</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5488394">5488394</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/28634268">28634268</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Endocrinology&rft.atitle=30+YEARS+OF+THE+MINERALOCORTICOID+RECEPTOR%3A+Mineralocorticoid+receptor+antagonists%3A+60+years+of+research+and+development&rft.volume=234&rft.issue=1&rft.pages=T125-T140&rft.date=2017-07&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5488394%23id-name%3DPMC&rft_id=info%3Apmid%2F28634268&rft_id=info%3Adoi%2F10.1530%2FJOE-16-0600&rft.aulast=Kolkhof&rft.aufirst=P&rft.au=B%C3%A4rfacker%2C+L&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5488394&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-GoldsmithCovic2014-108"><a href="#cite_ref-GoldsmithCovic2014_108-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGoldsmithCovicSpaak2014" class="citation book cs1">Goldsmith D, Covic A, Spaak J (12 November 2014). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=GvZWBQAAQBAJ&pg=PA167">Cardio-Renal Clinical Challenges</a>. Springer. pp. 167–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-319-09162-4" title="Special:BookSources/978-3-319-09162-4"><bdi>978-3-319-09162-4</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20221007093305/https://books.google.com/books?id=GvZWBQAAQBAJ&pg=PA167">Archived</a> from the original on 7 October 2022. 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Academic Press. pp. 630–632. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-08-053046-8" title="Special:BookSources/978-0-08-053046-8"><bdi>978-0-08-053046-8</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20140704201956/http://books.google.com/books?id=VHcsrw6unuAC&pg=PA630">Archived</a> from the original on 4 July 2014.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Diuretic+Agents%3A+Clinical+Physiology+and+Pharmacology&rft.pages=630-632&rft.pub=Academic+Press&rft.date=1997-09-23&rft.isbn=978-0-08-053046-8&rft.aulast=Seldin&rft.aufirst=DW&rft.au=Giebisch%2C+GH&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DVHcsrw6unuAC%26pg%3DPA630&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-Aronson2009-111">^ <a href="#cite_ref-Aronson2009_111-0">a</a> <a href="#cite_ref-Aronson2009_111-1">b</a> <a href="#cite_ref-Aronson2009_111-2">c</a> <a href="#cite_ref-Aronson2009_111-3">d</a> <a href="#cite_ref-Aronson2009_111-4">e</a> <a href="#cite_ref-Aronson2009_111-5">f</a> <a href="#cite_ref-Aronson2009_111-6">g</a> <a href="#cite_ref-Aronson2009_111-7">h</a> <a href="#cite_ref-Aronson2009_111-8">i</a> <a href="#cite_ref-Aronson2009_111-9">j</a> <a href="#cite_ref-Aronson2009_111-10">k</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAronson2009" class="citation book cs1">Aronson JK (2 March 2009). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=oeBgU3UwgZkC&pg=PA255">Meyler's Side Effects of Cardiovascular Drugs</a>. Elsevier. pp. 253–258. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-08-093289-7" title="Special:BookSources/978-0-08-093289-7"><bdi>978-0-08-093289-7</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20221007093806/https://books.google.com/books?id=oeBgU3UwgZkC&pg=PA255">Archived</a> from the original on 7 October 2022. 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Journal of the Endocrine Society. 3 (5): 1031–1038. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1210%2Fjs.2019-00030">10.1210/js.2019-00030</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6497918">6497918</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/31065620">31065620</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+Endocrine+Society&rft.atitle=The+Utility+of+Potassium+Monitoring+in+Gender-Diverse+Adolescents+Taking+Spironolactone&rft.volume=3&rft.issue=5&rft.pages=1031-1038&rft.date=2019-05&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6497918%23id-name%3DPMC&rft_id=info%3Apmid%2F31065620&rft_id=info%3Adoi%2F10.1210%2Fjs.2019-00030&rft.aulast=Millington&rft.aufirst=K&rft.au=Liu%2C+E&rft.au=Chan%2C+YM&rft_id=https%3A%2F%2Fdoi.org%2F10.1210%252Fjs.2019-00030&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-pmid36267595-127">^ <a href="#cite_ref-pmid36267595_127-0">a</a> <a href="#cite_ref-pmid36267595_127-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHayesRussellHaugenNagavally2022" class="citation journal cs1">Hayes H, Russell R, Haugen A, Nagavally S, Sarvaideo J (October 2022). <a rel="nofollow" class="external text" href="https://doi.org/10.1210%2Fjendso%2Fbvac133">"The Utility of Monitoring Potassium in Transgender, Gender Diverse, and Nonbinary Individuals on Spironolactone"</a>. Journal of the Endocrine Society. 6 (11): bvac133. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1210%2Fjendso%2Fbvac133">10.1210/jendso/bvac133</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9562816">9562816</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/36267595">36267595</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+Endocrine+Society&rft.atitle=The+Utility+of+Monitoring+Potassium+in+Transgender%2C+Gender+Diverse%2C+and+Nonbinary+Individuals+on+Spironolactone&rft.volume=6&rft.issue=11&rft.pages=bvac133&rft.date=2022-10&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC9562816%23id-name%3DPMC&rft_id=info%3Apmid%2F36267595&rft_id=info%3Adoi%2F10.1210%2Fjendso%2Fbvac133&rft.aulast=Hayes&rft.aufirst=H&rft.au=Russell%2C+R&rft.au=Haugen%2C+A&rft.au=Nagavally%2C+S&rft.au=Sarvaideo%2C+J&rft_id=https%3A%2F%2Fdoi.org%2F10.1210%252Fjendso%252Fbvac133&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-Becker2001-128">^ <a href="#cite_ref-Becker2001_128-0">a</a> <a href="#cite_ref-Becker2001_128-1">b</a> <a href="#cite_ref-Becker2001_128-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBecker2001" class="citation book cs1">Becker KL (2001). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=FVfzRvaucq8C&pg=PA1196">Principles and Practice of Endocrinology and Metabolism</a>. 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Springer. p. 44. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-319-34141-5" title="Special:BookSources/978-3-319-34141-5"><bdi>978-3-319-34141-5</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20221007093807/https://books.google.com/books?id=MFfYDAAAQBAJ&pg=PA44">Archived</a> from the original on 7 October 2022. 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John Wiley & Sons. pp. 486–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-118-81959-3" title="Special:BookSources/978-1-118-81959-3"><bdi>978-1-118-81959-3</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170908165041/https://books.google.com/books?id=VOLhBQAAQBAJ&pg=PA486">Archived</a> from the original on 8 September 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Neonatal+Formulary%3A+Drug+Use+in+Pregnancy+and+the+First+Year+of+Life&rft.pages=486-&rft.pub=John+Wiley+%26+Sons&rft.date=2014-11-10&rft.isbn=978-1-118-81959-3&rft.aulast=Ainsworth&rft.aufirst=SB&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DVOLhBQAAQBAJ%26pg%3DPA486&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-Little2006-161">^ <a href="#cite_ref-Little2006_161-0">a</a> <a href="#cite_ref-Little2006_161-1">b</a> <a href="#cite_ref-Little2006_161-2">c</a> <a href="#cite_ref-Little2006_161-3">d</a> <a href="#cite_ref-Little2006_161-4">e</a> <a href="#cite_ref-Little2006_161-5">f</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLittle2006" class="citation book cs1">Little B (29 September 2006). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=lnySHcBjXsEC&pg=PA63">Drugs and Pregnancy: A Handbook</a>. CRC Press. pp. 63–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-340-80917-4" title="Special:BookSources/978-0-340-80917-4"><bdi>978-0-340-80917-4</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170908165041/https://books.google.com/books?id=lnySHcBjXsEC&pg=PA63">Archived</a> from the original on 8 September 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Drugs+and+Pregnancy%3A+A+Handbook&rft.pages=63-&rft.pub=CRC+Press&rft.date=2006-09-29&rft.isbn=978-0-340-80917-4&rft.aulast=Little&rft.aufirst=B&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DlnySHcBjXsEC%26pg%3DPA63&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-RubinRamsey2008-162">^ <a href="#cite_ref-RubinRamsey2008_162-0">a</a> <a href="#cite_ref-RubinRamsey2008_162-1">b</a> <a href="#cite_ref-RubinRamsey2008_162-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRubinRamsey2008" class="citation book cs1">Rubin PC, Ramsey M (30 April 2008). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=2zHGHec53oMC&pg=PA83">Prescribing in Pregnancy</a>. John Wiley & Sons. pp. 83–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-470-69555-5" title="Special:BookSources/978-0-470-69555-5"><bdi>978-0-470-69555-5</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170908165041/https://books.google.com/books?id=2zHGHec53oMC&pg=PA83">Archived</a> from the original on 8 September 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Prescribing+in+Pregnancy&rft.pages=83-&rft.pub=John+Wiley+%26+Sons&rft.date=2008-04-30&rft.isbn=978-0-470-69555-5&rft.aulast=Rubin&rft.aufirst=PC&rft.au=Ramsey%2C+M&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D2zHGHec53oMC%26pg%3DPA83&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-BriggsFreeman2011-163">^ <a href="#cite_ref-BriggsFreeman2011_163-0">a</a> <a href="#cite_ref-BriggsFreeman2011_163-1">b</a> <a href="#cite_ref-BriggsFreeman2011_163-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBriggsFreemanYaffe2011" class="citation book cs1">Briggs GG, Freeman RK, Yaffe SJ (2011). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=OIgTE4aynrMC&pg=PA1349">Drugs in Pregnancy and Lactation: A Reference Guide to Fetal and Neonatal Risk</a>. Lippincott Williams & Wilkins. pp. 1349–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-60831-708-0" title="Special:BookSources/978-1-60831-708-0"><bdi>978-1-60831-708-0</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170908165041/https://books.google.com/books?id=OIgTE4aynrMC&pg=PA1349">Archived</a> from the original on 8 September 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Drugs+in+Pregnancy+and+Lactation%3A+A+Reference+Guide+to+Fetal+and+Neonatal+Risk&rft.pages=1349-&rft.pub=Lippincott+Williams+%26+Wilkins&rft.date=2011&rft.isbn=978-1-60831-708-0&rft.aulast=Briggs&rft.aufirst=GG&rft.au=Freeman%2C+RK&rft.au=Yaffe%2C+SJ&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DOIgTE4aynrMC%26pg%3DPA1349&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-ElkayamGleicher1998-164"><a href="#cite_ref-ElkayamGleicher1998_164-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGleicherElkayamGleicher1998" class="citation book cs1">Gleicher N, Elkayam U, Gleicher N (23 June 1998). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=z6E-Hgeu1nYC&pg=PA353">Cardiac Problems in Pregnancy: Diagnosis and Management of Maternal and Fetal Heart Disease</a>. John Wiley & Sons. pp. 353–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-16358-9" title="Special:BookSources/978-0-471-16358-9"><bdi>978-0-471-16358-9</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170908165041/https://books.google.com/books?id=z6E-Hgeu1nYC&pg=PA353">Archived</a> from the original on 8 September 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Cardiac+Problems+in+Pregnancy%3A+Diagnosis+and+Management+of+Maternal+and+Fetal+Heart+Disease&rft.pages=353-&rft.pub=John+Wiley+%26+Sons&rft.date=1998-06-23&rft.isbn=978-0-471-16358-9&rft.aulast=Gleicher&rft.aufirst=N&rft.au=Elkayam%2C+U&rft.au=Gleicher%2C+N&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dz6E-Hgeu1nYC%26pg%3DPA353&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-Schaefer2001-165">^ <a href="#cite_ref-Schaefer2001_165-0">a</a> <a href="#cite_ref-Schaefer2001_165-1">b</a> <a href="#cite_ref-Schaefer2001_165-2">c</a> <a href="#cite_ref-Schaefer2001_165-3">d</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSchaefer2001" class="citation book cs1">Schaefer C (2001). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=CE569saGK70C&pg=PA115">Drugs During Pregnancy and Lactation: Handbook of Prescription Drugs and Comparative Risk Assessment</a>. Gulf Professional Publishing. pp. 115, 143. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-444-50763-1" title="Special:BookSources/978-0-444-50763-1"><bdi>978-0-444-50763-1</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170908165041/https://books.google.com/books?id=CE569saGK70C&pg=PA115">Archived</a> from the original on 8 September 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Drugs+During+Pregnancy+and+Lactation%3A+Handbook+of+Prescription+Drugs+and+Comparative+Risk+Assessment&rft.pages=115%2C+143&rft.pub=Gulf+Professional+Publishing&rft.date=2001&rft.isbn=978-0-444-50763-1&rft.aulast=Schaefer&rft.aufirst=C&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DCE569saGK70C%26pg%3DPA115&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-Upfal2006-166"><a href="#cite_ref-Upfal2006_166-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFUpfal2006" class="citation book cs1">Upfal J (2006). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=7O9kiqN2q2YC&pg=PA671">Australian Drug Guide</a>. 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Journal of Psychiatric Research. 44 (6): 339–46. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.jpsychires.2009.10.006">10.1016/j.jpsychires.2009.10.006</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/19909979">19909979</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Psychiatric+Research&rft.atitle=Modulation+of+the+mineralocorticoid+receptor+as+add-on+treatment+in+depression%3A+a+randomized%2C+double-blind%2C+placebo-controlled+proof-of-concept+study&rft.volume=44&rft.issue=6&rft.pages=339-46&rft.date=2010-04&rft_id=info%3Adoi%2F10.1016%2Fj.jpsychires.2009.10.006&rft_id=info%3Apmid%2F19909979&rft.aulast=Otte&rft.aufirst=C&rft.au=Hinkelmann%2C+K&rft.au=Moritz%2C+S&rft.au=Yassouridis%2C+A&rft.au=Jahn%2C+H&rft.au=Wiedemann%2C+K&rft.au=Kellner%2C+M&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-pmid21515309-184"><a href="#cite_ref-pmid21515309_184-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMostalac-Preciadode_GortariLópez-Rubalcava2011" class="citation journal cs1">Mostalac-Preciado CR, de Gortari P, López-Rubalcava C (September 2011). 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Steroids. 78 (1): 102–7. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.steroids.2012.09.005">10.1016/j.steroids.2012.09.005</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/23063964">23063964</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:8992318">8992318</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Steroids&rft.atitle=A+safe+and+practical+method+for+the+preparation+of+7%CE%B1-thioether+and+thioester+derivatives+of+spironolactone&rft.volume=78&rft.issue=1&rft.pages=102-7&rft.date=2013-01&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A8992318%23id-name%3DS2CID&rft_id=info%3Apmid%2F23063964&rft_id=info%3Adoi%2F10.1016%2Fj.steroids.2012.09.005&rft.aulast=Agusti&rft.aufirst=G&rft.au=Bourgeois%2C+S&rft.au=Cartiser%2C+N&rft.au=Fessi%2C+H&rft.au=Le+Borgne%2C+M&rft.au=Lomberget%2C+T&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-CancerOrganization2001-186">^ <a href="#cite_ref-CancerOrganization2001_186-0">a</a> <a href="#cite_ref-CancerOrganization2001_186-1">b</a> <a href="#cite_ref-CancerOrganization2001_186-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFInternational_Agency_for_Research_on_CancerWorld_Health_Organization2001" class="citation book cs1">International Agency for Research on Cancer, World Health Organization (2001). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=l965aqw_LSkC&pg=PA325">Some Thyrotropic Agents</a>. World Health Organization. pp. 325–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-92-832-1279-9" title="Special:BookSources/978-92-832-1279-9"><bdi>978-92-832-1279-9</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20221007094813/https://books.google.com/books?id=l965aqw_LSkC&pg=PA325">Archived</a> from the original on 7 October 2022. 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John Wiley & Sons. pp. 229, 231. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4051-4370-7" title="Special:BookSources/978-1-4051-4370-7"><bdi>978-1-4051-4370-7</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20221007092802/https://books.google.com/books?id=Z3PARx4oYDgC&pg=PA231">Archived</a> from the original on 7 October 2022. 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John Wiley & Sons. pp. 89–103. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4051-7253-0" title="Special:BookSources/978-1-4051-7253-0"><bdi>978-1-4051-7253-0</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20221007094310/https://books.google.com/books?id=6IfumyQQ35wC&pg=PA89">Archived</a> from the original on 7 October 2022. Retrieved 13 August 2018.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Heart+Failure%3A+Pharmacologic+Management&rft.pages=89-103&rft.pub=John+Wiley+%26+Sons&rft.date=2008-04-15&rft.isbn=978-1-4051-7253-0&rft.aulast=Feldman&rft.aufirst=AM&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D6IfumyQQ35wC%26pg%3DPA89&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-Health2015-189"><a href="#cite_ref-Health2015_189-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWalar2015" class="citation book cs1">Walar K (15 June 2015). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=AK1fDwAAQBAJ&pg=PA248">Pharmacology</a> (6th ed.). Wolter Kluwer Health. pp. 248–249. GGKEY:N57K51AQ0UA.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Pharmacology&rft.pages=248-249&rft.edition=6th&rft.pub=Wolter+Kluwer+Health&rft.date=2015-06-15&rft.aulast=Walar&rft.aufirst=K&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DAK1fDwAAQBAJ%26pg%3DPA248&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988">[<a href="/wiki/Wikipedia:Link_rot" title="Wikipedia:Link rot">permanent dead link</a>‍] </li> <li id="cite_note-pmid24456327-190"><a href="#cite_ref-pmid24456327_190-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTamargoSeguraRuilope2014" class="citation journal cs1">Tamargo J, Segura J, Ruilope LM (April 2014). "Diuretics in the treatment of hypertension. Part 2: loop diuretics and potassium-sparing agents". 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Elsevier Health Sciences. pp. 237–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4557-2758-2" title="Special:BookSources/978-1-4557-2758-2"><bdi>978-1-4557-2758-2</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20221007094311/https://books.google.com/books?id=KZ95AAAAQBAJ&pg=PA237">Archived</a> from the original on 7 October 2022. 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Human Kinetics. pp. 76–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4925-0162-6" title="Special:BookSources/978-1-4925-0162-6"><bdi>978-1-4925-0162-6</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20221007094311/https://books.google.com/books?id=bfuXCgAAQBAJ&pg=PA76">Archived</a> from the original on 7 October 2022. 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Elsevier Health Sciences. pp. 364–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4557-3801-4" title="Special:BookSources/978-1-4557-3801-4"><bdi>978-1-4557-3801-4</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20221007093304/https://books.google.com/books?id=Tqpsm5WKKlcC&pg=PA364">Archived</a> from the original on 7 October 2022. 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Elsevier Health Sciences. pp. 161–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4377-1121-9" title="Special:BookSources/978-1-4377-1121-9"><bdi>978-1-4377-1121-9</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20221007094814/https://books.google.com/books?id=1u4x_iGiHNEC&pg=PA161">Archived</a> from the original on 7 October 2022. Retrieved 14 September 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Breast%3A+Comprehensive+Management+of+Benign+and+Malignant+Diseases&rft.pages=161-&rft.pub=Elsevier+Health+Sciences&rft.date=2009-09-09&rft.isbn=978-1-4377-1121-9&rft.aulast=Bland&rft.aufirst=KI&rft.au=Copeland+III%2C+EM&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D1u4x_iGiHNEC%26pg%3DPA161&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-pmid25376974-240"><a href="#cite_ref-pmid25376974_240-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMurckBüttnerKircherKonrad2014" class="citation journal cs1">Murck H, Büttner M, Kircher T, Konrad C (2014). <a rel="nofollow" class="external text" href="https://doi.org/10.1159%2F000368265">"Genetic, molecular and clinical determinants for the involvement of aldosterone and its receptors in major depression"</a>. Nephron Physiology. 128 (1–2): 17–25. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1159%2F000368265">10.1159/000368265</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/25376974">25376974</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:19905165">19905165</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nephron+Physiology&rft.atitle=Genetic%2C+molecular+and+clinical+determinants+for+the+involvement+of+aldosterone+and+its+receptors+in+major+depression&rft.volume=128&rft.issue=1%E2%80%932&rft.pages=17-25&rft.date=2014&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A19905165%23id-name%3DS2CID&rft_id=info%3Apmid%2F25376974&rft_id=info%3Adoi%2F10.1159%2F000368265&rft.aulast=Murck&rft.aufirst=H&rft.au=B%C3%BCttner%2C+M&rft.au=Kircher%2C+T&rft.au=Konrad%2C+C&rft_id=https%3A%2F%2Fdoi.org%2F10.1159%252F000368265&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-pmid22351473-241"><a href="#cite_ref-pmid22351473_241-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKünzel2012" class="citation journal cs1">Künzel HE (March 2012). "Psychopathological symptoms in patients with primary hyperaldosteronism--possible pathways". Hormone and Metabolic Research. 44 (3): 202–7. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1055%2Fs-0032-1301921">10.1055/s-0032-1301921</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/22351473">22351473</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:23273751">23273751</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Hormone+and+Metabolic+Research&rft.atitle=Psychopathological+symptoms+in+patients+with+primary+hyperaldosteronism--possible+pathways&rft.volume=44&rft.issue=3&rft.pages=202-7&rft.date=2012-03&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A23273751%23id-name%3DS2CID&rft_id=info%3Apmid%2F22351473&rft_id=info%3Adoi%2F10.1055%2Fs-0032-1301921&rft.aulast=K%C3%BCnzel&rft.aufirst=HE&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-pmid1629288-242">^ <a href="#cite_ref-pmid1629288_242-0">a</a> <a href="#cite_ref-pmid1629288_242-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFVarinTuBenoîtVilleneuve1992" class="citation journal cs1">Varin F, Tu TM, Benoît F, Villeneuve JP, Théorêt Y (February 1992). "High-performance liquid chromatographic determination of spironolactone and its metabolites in human biological fluids after solid-phase extraction". Journal of Chromatography. 574 (1): 57–64. <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%2F0378-4347%2892%2980097-A">10.1016/0378-4347(92)80097-A</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/1629288">1629288</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Chromatography&rft.atitle=High-performance+liquid+chromatographic+determination+of+spironolactone+and+its+metabolites+in+human+biological+fluids+after+solid-phase+extraction&rft.volume=574&rft.issue=1&rft.pages=57-64&rft.date=1992-02&rft_id=info%3Adoi%2F10.1016%2F0378-4347%2892%2980097-A&rft_id=info%3Apmid%2F1629288&rft.aulast=Varin&rft.aufirst=F&rft.au=Tu%2C+TM&rft.au=Beno%C3%AEt%2C+F&rft.au=Villeneuve%2C+JP&rft.au=Th%C3%A9or%C3%AAt%2C+Y&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-Oxford2003-243"><a href="#cite_ref-Oxford2003_243-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1"><a rel="nofollow" class="external text" href="https://books.google.com/books?id=_s65U1n9Lf8C&pg=RA1-PA962">Oxford Textbook of Medicine: Vol. 1</a>. Oxford University Press. 2003. pp. 1–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-19-262922-7" title="Special:BookSources/978-0-19-262922-7"><bdi>978-0-19-262922-7</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20221007094814/https://books.google.com/books?id=_s65U1n9Lf8C&pg=RA1-PA962">Archived</a> from the original on 7 October 2022. Retrieved 6 October 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Oxford+Textbook+of+Medicine%3A+Vol.+1&rft.pages=1-&rft.pub=Oxford+University+Press&rft.date=2003&rft.isbn=978-0-19-262922-7&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D_s65U1n9Lf8C%26pg%3DRA1-PA962&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-AnzenbacherZanger2012-244"><a href="#cite_ref-AnzenbacherZanger2012_244-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAnzenbacherZanger2012" class="citation book cs1">Anzenbacher P, Zanger UM (23 February 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=f-XHh17NfwgC&pg=PA166">Metabolism of Drugs and Other Xenobiotics</a>. John Wiley & Sons. pp. 166, 169. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-527-64632-6" title="Special:BookSources/978-3-527-64632-6"><bdi>978-3-527-64632-6</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20221007095315/https://books.google.com/books?id=f-XHh17NfwgC&pg=PA166">Archived</a> from the original on 7 October 2022. Retrieved 12 August 2018.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Metabolism+of+Drugs+and+Other+Xenobiotics&rft.pages=166%2C+169&rft.pub=John+Wiley+%26+Sons&rft.date=2012-02-23&rft.isbn=978-3-527-64632-6&rft.aulast=Anzenbacher&rft.aufirst=P&rft.au=Zanger%2C+UM&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Df-XHh17NfwgC%26pg%3DPA166&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-SmithPh.D.2014-245"><a href="#cite_ref-SmithPh.D.2014_245-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSmithSeawardSmith2014" class="citation book cs1">Smith BT, Seaward BL, Smith BT (1 November 2014). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=7P-9BQAAQBAJ&pg=PA169">Pharmacology for Nurses</a>. Jones & Bartlett Publishers. pp. 169–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4496-8940-7" title="Special:BookSources/978-1-4496-8940-7"><bdi>978-1-4496-8940-7</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20221007095315/https://books.google.com/books?id=7P-9BQAAQBAJ&pg=PA169">Archived</a> from the original on 7 October 2022. Retrieved 6 October 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Pharmacology+for+Nurses&rft.pages=169-&rft.pub=Jones+%26+Bartlett+Publishers&rft.date=2014-11-01&rft.isbn=978-1-4496-8940-7&rft.aulast=Smith&rft.aufirst=BT&rft.au=Seaward%2C+BL&rft.au=Smith%2C+BT&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D7P-9BQAAQBAJ%26pg%3DPA169&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-Montellano2015-246"><a href="#cite_ref-Montellano2015_246-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFOrtiz_de_Montellano2015" class="citation book cs1">Ortiz de Montellano PR (13 March 2015). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=abZnBwAAQBAJ&pg=PA867">Cytochrome P450: Structure, Mechanism, and Biochemistry</a>. Springer. pp. 867–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-319-12108-6" title="Special:BookSources/978-3-319-12108-6"><bdi>978-3-319-12108-6</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20221007095316/https://books.google.com/books?id=abZnBwAAQBAJ&pg=PA867">Archived</a> from the original on 7 October 2022. Retrieved 12 August 2018.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Cytochrome+P450%3A+Structure%2C+Mechanism%2C+and+Biochemistry&rft.pages=867-&rft.pub=Springer&rft.date=2015-03-13&rft.isbn=978-3-319-12108-6&rft.aulast=Ortiz+de+Montellano&rft.aufirst=PR&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DabZnBwAAQBAJ%26pg%3DPA867&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-AcademicPress2012-247"><a href="#cite_ref-AcademicPress2012_247-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1"><a rel="nofollow" class="external text" href="https://books.google.com/books?id=sC8h4KM0nmYC&pg=PA69">Advances in Clinical Chemistry</a>. Academic Press. 31 December 2012. pp. 69–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-12-405852-1" title="Special:BookSources/978-0-12-405852-1"><bdi>978-0-12-405852-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Advances+in+Clinical+Chemistry&rft.pages=69-&rft.pub=Academic+Press&rft.date=2012-12-31&rft.isbn=978-0-12-405852-1&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DsC8h4KM0nmYC%26pg%3DPA69&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-Brittain2002-248"><a href="#cite_ref-Brittain2002_248-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBrittain2002" class="citation book cs1">Brittain HG (26 November 2002). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=RMN5zMW64ZEC&pg=PA309">Analytical Profiles of Drug Substances and Excipients</a>. Academic Press. p. 309. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-12-260829-2" title="Special:BookSources/978-0-12-260829-2"><bdi>978-0-12-260829-2</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20130621104609/http://books.google.com/books?id=RMN5zMW64ZEC&pg=PA309">Archived</a> from the original on 21 June 2013. Retrieved 27 May 2012.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Analytical+Profiles+of+Drug+Substances+and+Excipients&rft.pages=309&rft.pub=Academic+Press&rft.date=2002-11-26&rft.isbn=978-0-12-260829-2&rft.aulast=Brittain&rft.aufirst=HG&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DRMN5zMW64ZEC%26pg%3DPA309&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-JamesonGroot2010-249">^ <a href="#cite_ref-JamesonGroot2010_249-0">a</a> <a href="#cite_ref-JamesonGroot2010_249-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJamesonDe_Groot2010" class="citation book cs1">Jameson JL, De Groot LJ (18 May 2010). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=W4dZ-URK8ZoC&pg=PA2401">Endocrinology - E-Book: Adult and Pediatric</a>. 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Springer. p. 1111. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4757-2085-3" title="Special:BookSources/978-1-4757-2085-3"><bdi>978-1-4757-2085-3</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170215024945/https://books.google.com/books?id=0vXTBwAAQBAJ">Archived</a> from the original on 15 February 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Dictionary+of+Drugs%3A+Chemical+Data%3A+Chemical+Data%2C+Structures+and+Bibliographies&rft.pages=1111&rft.pub=Springer&rft.date=2014-11-14&rft.isbn=978-1-4757-2085-3&rft.aulast=Elks&rft.aufirst=J&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D0vXTBwAAQBAJ%26pg%3DPA1111&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-PubChem-251">^ <a href="#cite_ref-PubChem_251-0">a</a> <a href="#cite_ref-PubChem_251-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/5833">"Spironolactone"</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20160630101052/http://pubchem.ncbi.nlm.nih.gov/compound/5833/">Archived</a> from the original on 30 June 2016. 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Retrieved 27 December 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Pharmaceutical+Substances%2C+5th+Edition%2C+2009%3A+Syntheses%2C+Patents+and+Applications+of+the+most+relevant+APIs&rft.pages=1279-1280&rft.pub=Thieme&rft.date=2014-05-14&rft.isbn=978-3-13-179275-4&rft.aulast=Engel&rft.aufirst=J&rft.au=Kleemann%2C+A&rft.au=Kutscher%2C+B&rft.au=Reichert%2C+D&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D4lCGAwAAQBAJ%26pg%3DPA1279&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-LandauAchilladelis1999-263"><a href="#cite_ref-LandauAchilladelis1999_263-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLandauAchilladelisScriabine1999" class="citation book cs1">Landau R, Achilladelis B, Scriabine A (1999). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=IH4lPs6S1bMC&pg=PA198">Pharmaceutical Innovation: Revolutionizing Human Health</a>. Chemical Heritage Foundation. pp. 198–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-941901-21-5" title="Special:BookSources/978-0-941901-21-5"><bdi>978-0-941901-21-5</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20221007095318/https://books.google.com/books?id=IH4lPs6S1bMC&pg=PA198">Archived</a> from the original on 7 October 2022. Retrieved 27 December 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Pharmaceutical+Innovation%3A+Revolutionizing+Human+Health&rft.pages=198-&rft.pub=Chemical+Heritage+Foundation&rft.date=1999&rft.isbn=978-0-941901-21-5&rft.aulast=Landau&rft.aufirst=R&rft.au=Achilladelis%2C+B&rft.au=Scriabine%2C+A&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DIH4lPs6S1bMC%26pg%3DPA198&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-Jugdutt2014-264"><a href="#cite_ref-Jugdutt2014_264-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJugdutt2014" class="citation book cs1">Jugdutt BI (19 February 2014). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=0e23BAAAQBAJ&pg=PA175">Aging and Heart Failure: Mechanisms and Management</a>. Springer Science & Business Media. pp. 175–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4939-0268-2" title="Special:BookSources/978-1-4939-0268-2"><bdi>978-1-4939-0268-2</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20221007095841/https://books.google.com/books?id=0e23BAAAQBAJ&pg=PA175">Archived</a> from the original on 7 October 2022. Retrieved 27 December 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Aging+and+Heart+Failure%3A+Mechanisms+and+Management&rft.pages=175-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2014-02-19&rft.isbn=978-1-4939-0268-2&rft.aulast=Jugdutt&rft.aufirst=BI&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D0e23BAAAQBAJ%26pg%3DPA175&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-Wermuth2011-265"><a href="#cite_ref-Wermuth2011_265-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWermuth2011" class="citation book cs1">Wermuth CG (2 May 2011). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=Qmt1_DQkCpEC&pg=PA34">The Practice of Medicinal Chemistry</a>. Academic Press. pp. 34–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-08-056877-5" title="Special:BookSources/978-0-08-056877-5"><bdi>978-0-08-056877-5</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20130621115634/http://books.google.com/books?id=Qmt1_DQkCpEC&pg=PA34">Archived</a> from the original on 21 June 2013.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Practice+of+Medicinal+Chemistry&rft.pages=34-&rft.pub=Academic+Press&rft.date=2011-05-02&rft.isbn=978-0-08-056877-5&rft.aulast=Wermuth&rft.aufirst=CG&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DQmt1_DQkCpEC%26pg%3DPA34&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-Smith1962-266"><a href="#cite_ref-Smith1962_266-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSmith1962" class="citation journal cs1">Smith WG (1962). 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The Lancet. 280 (7261): 886. <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%2FS0140-6736%2862%2990668-2">10.1016/S0140-6736(62)90668-2</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0140-6736">0140-6736</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Lancet&rft.atitle=Spironolactone+and+gynaecomastia&rft.volume=280&rft.issue=7261&rft.pages=886&rft.date=1962&rft_id=info%3Adoi%2F10.1016%2FS0140-6736%2862%2990668-2&rft.issn=0140-6736&rft.aulast=Smith&rft.aufirst=WG&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-pmid5344274-267"><a href="#cite_ref-pmid5344274_267-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSteelmanBrooksMorganPatanelli1969" class="citation journal cs1">Steelman SL, Brooks JR, Morgan ER, Patanelli DJ (October 1969). 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Steroids. 14 (4): 449–50. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fs0039-128x%2869%2980007-3">10.1016/s0039-128x(69)80007-3</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/5344274">5344274</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Steroids&rft.atitle=Anti-androgenic+activity+of+spironolactone&rft.volume=14&rft.issue=4&rft.pages=449-50&rft.date=1969-10&rft_id=info%3Adoi%2F10.1016%2Fs0039-128x%2869%2980007-3&rft_id=info%3Apmid%2F5344274&rft.aulast=Steelman&rft.aufirst=SL&rft.au=Brooks%2C+JR&rft.au=Morgan%2C+ER&rft.au=Patanelli%2C+DJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-pmid148431-268"><a href="#cite_ref-pmid148431_268-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFStewartPochi1978" class="citation journal cs1">Stewart ME, Pochi PE (April 1978). 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International Journal of Dermatology. 17 (3): 167–79. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1365-4362.1978.tb06057.x">10.1111/j.1365-4362.1978.tb06057.x</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/148431">148431</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:43649686">43649686</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=International+Journal+of+Dermatology&rft.atitle=Antiandrogens+and+the+skin&rft.volume=17&rft.issue=3&rft.pages=167-79&rft.date=1978-04&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A43649686%23id-name%3DS2CID&rft_id=info%3Apmid%2F148431&rft_id=info%3Adoi%2F10.1111%2Fj.1365-4362.1978.tb06057.x&rft.aulast=Stewart&rft.aufirst=ME&rft.au=Pochi%2C+PE&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-NeillJohansson1968-269"><a href="#cite_ref-NeillJohansson1968_269-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNeillJohanssonDattaKnobil1968" class="citation journal cs1">Neill JD, Johansson ED, Datta JK, Knobil, E (1968). 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Pharmacology & Therapeutics. 24 (3): 367–400. <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%2F0163-7258%2884%2990010-X">10.1016/0163-7258(84)90010-X</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/6205409">6205409</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pharmacology+%26+Therapeutics&rft.atitle=Androgen+antagonists+in+androgen+target+tissues&rft.volume=24&rft.issue=3&rft.pages=367-400&rft.date=1984&rft_id=info%3Adoi%2F10.1016%2F0163-7258%2884%2990010-X&rft_id=info%3Apmid%2F6205409&rft.aulast=Tindall&rft.aufirst=DJ&rft.au=Chang%2C+CH&rft.au=Lobl%2C+TJ&rft.au=Cunningham%2C+GR&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-pmid717935-271"><a href="#cite_ref-pmid717935_271-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFOberHennessy1978" class="citation journal cs1">Ober KP, Hennessy JF (November 1978). 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Annals of Internal Medicine. 89 (5 Pt 1): 643–4. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.7326%2F0003-4819-89-5-643">10.7326/0003-4819-89-5-643</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/717935">717935</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annals+of+Internal+Medicine&rft.atitle=Spironolactone+therapy+for+hirsutism+in+a+hyperandrogenic+woman&rft.volume=89&rft.issue=5+Pt+1&rft.pages=643-4&rft.date=1978-11&rft_id=info%3Adoi%2F10.7326%2F0003-4819-89-5-643&rft_id=info%3Apmid%2F717935&rft.aulast=Ober&rft.aufirst=KP&rft.au=Hennessy%2C+JF&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-pmid488407-272"><a href="#cite_ref-pmid488407_272-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBoisselleTremblay1979" class="citation journal cs1">Boisselle A, Tremblay RR (September 1979). 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The Journal of Clinical Endocrinology and Metabolism. 51 (3): 429–32. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1210%2Fjcem-51-3-429">10.1210/jcem-51-3-429</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/7410528">7410528</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Clinical+Endocrinology+and+Metabolism&rft.atitle=A+novel+use+of+spironolactone%3A+treatment+of+hirsutism&rft.volume=51&rft.issue=3&rft.pages=429-32&rft.date=1980-09&rft_id=info%3Adoi%2F10.1210%2Fjcem-51-3-429&rft_id=info%3Apmid%2F7410528&rft.aulast=Shapiro&rft.aufirst=G&rft.au=Evron%2C+S&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-Curtis2014-274"><a href="#cite_ref-Curtis2014_274-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCurtis2014" class="citation book cs1">Curtis M (2014). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=w2AGBAAAQBAJ&pg=PA47">Glass' Office Gynecology</a>. Lippincott Williams & Wilkins. pp. 47–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-60831-820-9" title="Special:BookSources/978-1-60831-820-9"><bdi>978-1-60831-820-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Glass%27+Office+Gynecology&rft.pages=47-&rft.pub=Lippincott+Williams+%26+Wilkins&rft.date=2014&rft.isbn=978-1-60831-820-9&rft.aulast=Curtis&rft.aufirst=M&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dw2AGBAAAQBAJ%26pg%3DPA47&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-ShahBhathena2004-275"><a href="#cite_ref-ShahBhathena2004_275-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFShahBhathenaShroff2004" class="citation book cs1">Shah D, Bhathena RK, Shroff S (2004). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=Jxd03OBIn9wC&pg=PA78">The Polycystic Ovary Syndrome</a>. Orient Blackswan. pp. 78–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-81-250-2633-4" title="Special:BookSources/978-81-250-2633-4"><bdi>978-81-250-2633-4</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20221007095842/https://books.google.com/books?id=Jxd03OBIn9wC&pg=PA78">Archived</a> from the original on 7 October 2022. Retrieved 4 July 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Polycystic+Ovary+Syndrome&rft.pages=78-&rft.pub=Orient+Blackswan&rft.date=2004&rft.isbn=978-81-250-2633-4&rft.aulast=Shah&rft.aufirst=D&rft.au=Bhathena%2C+RK&rft.au=Shroff%2C+S&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DJxd03OBIn9wC%26pg%3DPA78&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-Hillard2013-276"><a href="#cite_ref-Hillard2013_276-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHillard2013" class="citation book cs1">Hillard PJ (29 March 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=vAA5Z5aqlUQC&pg=PT371">Practical Pediatric and Adolescent Gynecology</a>. John Wiley & Sons. pp. 371–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-118-53857-9" title="Special:BookSources/978-1-118-53857-9"><bdi>978-1-118-53857-9</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20221007095842/https://books.google.com/books?id=vAA5Z5aqlUQC&pg=PT371">Archived</a> from the original on 7 October 2022. Retrieved 4 July 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Practical+Pediatric+and+Adolescent+Gynecology&rft.pages=371-&rft.pub=John+Wiley+%26+Sons&rft.date=2013-03-29&rft.isbn=978-1-118-53857-9&rft.aulast=Hillard&rft.aufirst=PJ&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DvAA5Z5aqlUQC%26pg%3DPT371&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-DahlFeldman2006-277"><a href="#cite_ref-DahlFeldman2006_277-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDahlFeldmanGoldbergJaberi2006" class="citation journal cs1">Dahl M, Feldman JL, Goldberg JM, Jaberi A (2006). "Physical Aspects of Transgender Endocrine Therapy". International Journal of Transgenderism. 9 (3–4): 111–134. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1300%2FJ485v09n03_06">10.1300/J485v09n03_06</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1553-2739">1553-2739</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:146232471">146232471</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=International+Journal+of+Transgenderism&rft.atitle=Physical+Aspects+of+Transgender+Endocrine+Therapy&rft.volume=9&rft.issue=3%E2%80%934&rft.pages=111-134&rft.date=2006&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A146232471%23id-name%3DS2CID&rft.issn=1553-2739&rft_id=info%3Adoi%2F10.1300%2FJ485v09n03_06&rft.aulast=Dahl&rft.aufirst=M&rft.au=Feldman%2C+JL&rft.au=Goldberg%2C+JM&rft.au=Jaberi%2C+A&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-PriorVigna1986-278"><a href="#cite_ref-PriorVigna1986_278-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPriorVignaWatsonDiewold" class="citation journal cs1">Prior JC, Vigna YM, Watson D, Diewold P, Robinow O. 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Journal of Sex Information & Education Council of Canada (1): 1–7.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Sex+Information+%26+Education+Council+of+Canada&rft.atitle=Spironolactone+in+the+presurgical+therapy+of+male+to+female+transsexuals%3A+Philosophy+and+experience+of+the+Vancouver+Gender+Dysphoria+Clinic&rft.issue=1&rft.pages=1-7&rft.aulast=Prior&rft.aufirst=JC&rft.au=Vigna%2C+YM&rft.au=Watson%2C+D&rft.au=Diewold%2C+P&rft.au=Robinow%2C+O&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-FisherMaggi2015-279"><a href="#cite_ref-FisherMaggi2015_279-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFisherMaggi2015" class="citation book cs1">Fisher AD, Maggi M (2015). "Endocrine Treatment of Transsexual Male-to-Female Persons". Management of Gender Dysphoria. Springer. pp. 83–91. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-88-470-5696-1_10">10.1007/978-88-470-5696-1_10</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-88-470-5695-4" title="Special:BookSources/978-88-470-5695-4"><bdi>978-88-470-5695-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Endocrine+Treatment+of+Transsexual+Male-to-Female+Persons&rft.btitle=Management+of+Gender+Dysphoria&rft.pages=83-91&rft.pub=Springer&rft.date=2015&rft_id=info%3Adoi%2F10.1007%2F978-88-470-5696-1_10&rft.isbn=978-88-470-5695-4&rft.aulast=Fisher&rft.aufirst=AD&rft.au=Maggi%2C+M&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-Dorfman2016-280">^ <a href="#cite_ref-Dorfman2016_280-0">a</a> <a href="#cite_ref-Dorfman2016_280-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDorfman2016" class="citation book cs1">Dorfman RI (5 December 2016). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=BbLfBAAAQBAJ&pg=PA392">Steroidal Activity in Experimental Animals and Man</a>. Elsevier Science. pp. 392–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4832-7299-3" title="Special:BookSources/978-1-4832-7299-3"><bdi>978-1-4832-7299-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Steroidal+Activity+in+Experimental+Animals+and+Man&rft.pages=392-&rft.pub=Elsevier+Science&rft.date=2016-12-05&rft.isbn=978-1-4832-7299-3&rft.aulast=Dorfman&rft.aufirst=RI&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DBbLfBAAAQBAJ%26pg%3DPA392&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-GlázVecsei2017-281"><a href="#cite_ref-GlázVecsei2017_281-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGlázVecsei2017" class="citation book cs1">Gláz E, Vecsei P (11 January 2017). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=ya3YBAAAQBAJ&pg=PA380">Aldosterone: International Series of Monographs in Pure and Applied Biology</a>. Elsevier Science. p. 379. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4831-5997-3" title="Special:BookSources/978-1-4831-5997-3"><bdi>978-1-4831-5997-3</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20221010052225/https://books.google.com/books?id=ya3YBAAAQBAJ&pg=PA380">Archived</a> from the original on 10 October 2022. 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Springer Science & Business Media. pp. 261ff. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7514-0499-9" title="Special:BookSources/978-0-7514-0499-9"><bdi>978-0-7514-0499-9</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20221007095843/https://books.google.com/books?id=mqaOMOtk61IC&pg=PA261">Archived</a> from the original on 7 October 2022. Retrieved 1 December 2016.</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=261ff&rft.pub=Springer+Science+%26+Business+Media&rft.date=1999-10-31&rft.isbn=978-0-7514-0499-9&rft.aulast=Morton&rft.aufirst=IK&rft.au=Hall%2C+JM&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DmqaOMOtk61IC%26pg%3DPA261&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-Springer2012-283">^ <a href="#cite_ref-Springer2012_283-0">a</a> <a href="#cite_ref-Springer2012_283-1">b</a> <a href="#cite_ref-Springer2012_283-2">c</a> <a href="#cite_ref-Springer2012_283-3">d</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1"><a rel="nofollow" class="external text" href="https://books.google.com/books?id=Z5K-BwAAQBAJ&pg=PA266">Benign Prostatic Hypertrophy</a>. 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Urology. 37 (1): 1–16. <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%2F0090-4295%2891%2980069-j">10.1016/0090-4295(91)80069-j</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/1702565">1702565</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Urology&rft.atitle=Endocrine+treatment+of+benign+prostatic+hypertrophy%3A+current+concepts&rft.volume=37&rft.issue=1&rft.pages=1-16&rft.date=1991-01&rft_id=info%3Adoi%2F10.1016%2F0090-4295%2891%2980069-j&rft_id=info%3Apmid%2F1702565&rft.aulast=Matzkin&rft.aufirst=H&rft.au=Braf%2C+Z&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-pmid4104441-285">^ <a href="#cite_ref-pmid4104441_285-0">a</a> <a href="#cite_ref-pmid4104441_285-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCastroGriffithsEdwards1971" class="citation journal cs1">Castro JE, Griffiths HJ, Edwards DE (July 1971). 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The British Journal of Surgery. 58 (7): 485–9. <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%2Fbjs.1800580703">10.1002/bjs.1800580703</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/4104441">4104441</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:27601630">27601630</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+British+Journal+of+Surgery&rft.atitle=A+double-blind%2C+controlled%2C+clinical+trial+of+spironolactone+for+benign+prostatic+hypertrophy&rft.volume=58&rft.issue=7&rft.pages=485-9&rft.date=1971-07&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A27601630%23id-name%3DS2CID&rft_id=info%3Apmid%2F4104441&rft_id=info%3Adoi%2F10.1002%2Fbjs.1800580703&rft.aulast=Castro&rft.aufirst=JE&rft.au=Griffiths%2C+HJ&rft.au=Edwards%2C+DE&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASpironolactone" class="Z3988"> </li> <li id="cite_note-pmid29603164-286"><a href="#cite_ref-pmid29603164_286-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFScottMenonWalsh1980" class="citation journal cs1">Scott WW, Menon M, Walsh PC (April 1980). <a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fcncr.1980.45.s7.1929">"Hormonal Therapy of Prostatic Cancer"</a>. 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class="nowraplinks mw-collapsible expanded 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:Spironolactone" title="Template:Spironolactone"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Spironolactone" title="Template talk:Spironolactone"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Spironolactone" title="Special:EditPage/Template:Spironolactone"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Spironolactone" style="font-size:114%;margin:0 4em"><a class="mw-selflink selflink">Spironolactone</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Topics</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/Pharmacodynamics_of_spironolactone" title="Pharmacodynamics of spironolactone">Pharmacodynamics of spironolactone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Metabolites</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/7%CE%B1-Thiomethylspironolactone" title="7α-Thiomethylspironolactone">7α-Thiomethylspironolactone</a> (major)</li> <li><a href="/wiki/Canrenone" title="Canrenone">Canrenone</a> (minor)</li> <li><a href="/wiki/6%CE%B2-Hydroxy-7%CE%B1-thiomethylspironolactone" title="6β-Hydroxy-7α-thiomethylspironolactone">6β-Hydroxy-7α-thiomethylspironolactone</a> (minor)</li> <li><a href="/wiki/7%CE%B1-Thiospironolactone" title="7α-Thiospironolactone">7α-Thiospironolactone</a> (minor)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Related drugs</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/Spirolactone" title="Spirolactone">Spirolactone</a> <a href="/wiki/Antimineralocorticoid" class="mw-redirect" title="Antimineralocorticoid">antimineralocorticoids</a>: <a href="/wiki/Canrenone" title="Canrenone">Canrenone</a></li> <li><a href="/wiki/Potassium_canrenoate" title="Potassium canrenoate">Potassium canrenoate</a></li> <li><a href="/wiki/Drospirenone" title="Drospirenone">Drospirenone</a></li> <li><a href="/wiki/Eplerenone" title="Eplerenone">Eplerenone</a></li></ul> </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="Medical_uses" 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="Medical_uses" style="font-size:114%;margin:0 4em"><a href="/wiki/Medicine" title="Medicine">Medical uses</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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Diuretics_(C03)" 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:Diuretics" title="Template:Diuretics"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Diuretics" title="Template talk:Diuretics"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Diuretics" title="Special:EditPage/Template:Diuretics"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Diuretics_(C03)" style="font-size:114%;margin:0 4em"><a href="/wiki/Diuretic" title="Diuretic">Diuretics</a> (<a href="/wiki/ATC_code_C03" title="ATC code C03">C03</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sulfonamide_(medicine)" title="Sulfonamide (medicine)">Sulfonamides</a> (and <a href="/wiki/Etacrynic_acid" title="Etacrynic acid">etacrynic acid</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbonic_anhydrase_inhibitor" title="Carbonic anhydrase inhibitor">CA inhibitors</a> (at <a href="/wiki/Proximal_tubule" title="Proximal tubule">PT</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetazolamide" title="Acetazolamide">Acetazolamide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Loop_diuretic" title="Loop diuretic">Loop</a> (<a href="/wiki/Na-K-Cl_cotransporter" class="mw-redirect" title="Na-K-Cl cotransporter">Na-K-Cl</a> at <a href="/wiki/Thick_ascending_limb_of_loop_of_Henle" class="mw-redirect" title="Thick ascending limb of loop of Henle">AL</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/Furosemide" title="Furosemide">Furosemide</a>#</li> <li><a href="/wiki/Azosemide" title="Azosemide">Azosemide</a></li> <li><a href="/wiki/Bumetanide" title="Bumetanide">Bumetanide</a></li> <li><a href="/wiki/Etacrynic_acid" title="Etacrynic acid">Etacrynic acid</a></li> <li><a href="/wiki/Etozolin" title="Etozolin">Etozolin</a></li> <li><a href="/wiki/Indacrinone" title="Indacrinone">Indacrinone</a></li> <li><a href="/wiki/Muzolimine" title="Muzolimine">Muzolimine</a></li> <li><a href="/wiki/Ozolinone" title="Ozolinone">Ozolinone</a></li> <li><a href="/wiki/Piretanide" title="Piretanide">Piretanide</a></li> <li><a href="/wiki/Tienilic_acid" title="Tienilic acid">Tienilic acid</a>‡</li> <li><a href="/wiki/Torasemide" title="Torasemide">Torasemide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Thiazide" title="Thiazide">Thiazides</a> (<a href="/wiki/Sodium-chloride_symporter" title="Sodium-chloride symporter">Na-Cl</a> at <a href="/wiki/Distal_convoluted_tubule" title="Distal convoluted tubule">DCT</a>, <a href="/wiki/Diuretic#Calcium-sparing_diuretics" title="Diuretic">Calcium-sparing</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Altizide" title="Altizide">Altizide</a></li> <li><a href="/wiki/Bendroflumethiazide" title="Bendroflumethiazide">Bendroflumethiazide</a></li> <li><a href="/wiki/Butizide" title="Butizide">Butizide</a></li> <li><a href="/wiki/Chlorothiazide" title="Chlorothiazide">Chlorothiazide</a></li> <li><a href="/wiki/Cyclopenthiazide" title="Cyclopenthiazide">Cyclopenthiazide</a></li> <li><a href="/wiki/Cyclothiazide" title="Cyclothiazide">Cyclothiazide</a></li> <li><a href="/wiki/Epitizide" title="Epitizide">Epitizide</a></li> <li><a href="/wiki/Hydrochlorothiazide" title="Hydrochlorothiazide">Hydrochlorothiazide</a></li> <li><a href="/wiki/Hydroflumethiazide" title="Hydroflumethiazide">Hydroflumethiazide</a></li> <li><a href="/wiki/Mebutizide" title="Mebutizide">Mebutizide</a></li> <li><a href="/wiki/Methyclothiazide" title="Methyclothiazide">Methyclothiazide</a></li> <li><a href="/wiki/Polythiazide" title="Polythiazide">Polythiazide</a></li> <li><a href="/wiki/Trichlormethiazide" title="Trichlormethiazide">Trichlormethiazide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Thiazide-like_diuretic" title="Thiazide-like diuretic">Thiazide-likes</a> (primarily <a href="/wiki/Distal_convoluted_tubule" title="Distal convoluted tubule">DCT</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/Chlortalidone" title="Chlortalidone">Chlortalidone</a></li> <li><a href="/wiki/Clofenamide" title="Clofenamide">Clofenamide</a></li> <li><a href="/wiki/Clopamide" title="Clopamide">Clopamide</a></li> <li><a href="/wiki/Clorexolone" title="Clorexolone">Clorexolone</a></li> <li><a href="/wiki/Fenquizone" title="Fenquizone">Fenquizone</a></li> <li><a href="/wiki/Indapamide" title="Indapamide">Indapamide</a></li> <li><a href="/wiki/Mefruside" title="Mefruside">Mefruside</a></li> <li><a href="/wiki/Meticrane" title="Meticrane">Meticrane</a></li> <li><a href="/wiki/Metolazone" title="Metolazone">Metolazone</a></li> <li><a href="/wiki/Quinethazone" title="Quinethazone">Quinethazone</a></li> <li><a href="/wiki/Xipamide" title="Xipamide">Xipamide</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Potassium-sparing_diuretic" title="Potassium-sparing diuretic">Potassium-sparing</a> (at <a href="/wiki/Collecting_duct_system" title="Collecting duct system">CD</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Epithelial_sodium_channel_blocker" title="Epithelial sodium channel blocker">ESC blockers</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amiloride" title="Amiloride">Amiloride</a>#</li> <li><a href="/wiki/Benzamil" title="Benzamil">Benzamil</a></li> <li><a href="/wiki/Triamterene" title="Triamterene">Triamterene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antimineralocorticoid" class="mw-redirect" title="Antimineralocorticoid">Aldosterone antagonists</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/Spirolactone" title="Spirolactone">Spirolactones</a> <ul><li><a class="mw-selflink selflink">Spironolactone</a>#</li> <li><a href="/wiki/Canrenone" title="Canrenone">Canrenone</a></li> <li><a href="/wiki/Eplerenone" title="Eplerenone">Eplerenone</a></li> <li><a href="/wiki/Potassium_canrenoate" title="Potassium canrenoate">Potassium canrenoate</a></li></ul></li></ul> <ul><li><a href="/wiki/Nonsteroidal" title="Nonsteroidal">Nonsteroidal</a> <ul><li><a href="/wiki/Finerenone" title="Finerenone">Finerenone</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Osmotic_diuretic" title="Osmotic diuretic">Osmotic diuretics</a> (<a href="/wiki/Proximal_tubule" title="Proximal tubule">PT</a>, <a href="/wiki/Descending_limb_of_loop_of_Henle" title="Descending limb of loop of Henle">DL</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Mannitol" title="Mannitol">Mannitol</a>#</li> <li><a href="/wiki/Glycerol" title="Glycerol">Glycerol</a></li> <li><a href="/wiki/Urea" title="Urea">Urea</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vasopressin_receptor_antagonist" title="Vasopressin receptor antagonist">Vasopressin receptor inhibitors</a> (<a href="/wiki/Distal_convoluted_tubule" title="Distal convoluted tubule">DCT</a> and <a href="/wiki/Collecting_duct" class="mw-redirect" title="Collecting duct">CD</a>)</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Vasopressin_receptor_antagonist#Vaptans" title="Vasopressin receptor antagonist">Vaptans</a> <ul><li><a href="/wiki/Conivaptan" title="Conivaptan">Conivaptan</a></li> <li><a href="/wiki/Mozavaptan" title="Mozavaptan">Mozavaptan</a></li> <li><a href="/wiki/Satavaptan" title="Satavaptan">Satavaptan</a></li> <li><a href="/wiki/Tolvaptan" title="Tolvaptan">Tolvaptan</a></li></ul></li></ul> <ul><li><a href="/wiki/Vasopressin_receptor_antagonist#Demeclocycline_and_lithium" title="Vasopressin receptor antagonist">Others</a> <ul><li><a href="/wiki/Demeclocycline" title="Demeclocycline">Demeclocycline</a></li> <li><a href="/wiki/Lithium_carbonate" title="Lithium carbonate">Lithium carbonate</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a>, <a href="/wiki/Isopropanol" class="mw-redirect" title="Isopropanol">Isopropanol</a>, <a href="/wiki/Tert-Amyl_alcohol" title="Tert-Amyl alcohol">2M2B</a></li> <li><a href="/wiki/Mercurial_diuretic" title="Mercurial diuretic">mercurial diuretics</a> (<a href="/wiki/Chlormerodrin" title="Chlormerodrin">Chlormerodrin</a>, <a href="/wiki/Mersalyl" title="Mersalyl">Mersalyl</a>, <a href="/wiki/Meralluride" title="Meralluride">Meralluride</a>)</li> <li><a href="/wiki/Theobromine" title="Theobromine">Theobromine</a></li> <li><a href="/wiki/Cicletanine" title="Cicletanine">Cicletanine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Combination products</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/Hydrochlorothiazide/triamterene" title="Hydrochlorothiazide/triamterene">Hydrochlorothiazide/triamterene</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="background: transparent; padding: 0px;"><div><div class="hlist"> <ul><li>#<a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li>‡<a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li>†<a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li>§Never to phase III</li></ul></li></ul> </div></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="Acne-treating_agents_(D10)" 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:Acne-treating_agents" title="Template:Acne-treating agents"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Acne-treating_agents" title="Template talk:Acne-treating agents"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Acne-treating_agents" title="Special:EditPage/Template:Acne-treating agents"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Acne-treating_agents_(D10)" style="font-size:114%;margin:0 4em"><a href="/wiki/Acne_vulgaris" class="mw-redirect" title="Acne vulgaris">Acne</a>-treating agents (<a href="/wiki/ATC_code_D10" title="ATC code D10">D10</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antiseptic" title="Antiseptic">Antibacterial</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Azelaic_acid" title="Azelaic acid">Azelaic acid</a></li> <li><a href="/wiki/Benzoyl_peroxide" title="Benzoyl peroxide">Benzoyl peroxide</a>#</li> <li><a href="/wiki/8-Hydroxyquinoline" title="8-Hydroxyquinoline">8-Hydroxyquinoline</a></li> <li><a href="/wiki/Light_therapy" title="Light therapy">Blue light therapy</a></li> <li><a href="/wiki/Tea_tree_oil" title="Tea tree oil">Tea tree oil</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Keratolytic" title="Keratolytic">Keratolytic</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Glycolic_acid" title="Glycolic acid">Glycolic acid</a></li> <li><a href="/wiki/Salicylic_acid" title="Salicylic acid">Salicylic acid</a>#</li> <li><a href="/wiki/Sulfur_(pharmacy)" class="mw-redirect" title="Sulfur (pharmacy)">Sulfur</a></li> <li><a href="/wiki/Benzoyl_peroxide" title="Benzoyl peroxide">Benzoyl peroxide</a>#</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Anti-inflammatory" title="Anti-inflammatory">Anti-inflammatory</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Niacinamide" class="mw-redirect" title="Niacinamide">Niacinamide</a></li> <li><a href="/wiki/Ibuprofen" title="Ibuprofen">Ibuprofen</a>#</li> <li><a href="/wiki/Aspirin" title="Aspirin">Aspirin</a>#</li> <li><a href="/wiki/Light_therapy" title="Light therapy">Red light therapy</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antibiotics" class="mw-redirect" title="Antibiotics">Antibiotics</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Clindamycin" title="Clindamycin">Clindamycin</a></li> <li><a href="/wiki/Dapsone" title="Dapsone">Dapsone</a></li> <li><a href="/wiki/Erythromycin" title="Erythromycin">Erythromycin</a></li> <li><a href="/wiki/Sulfacetamide" title="Sulfacetamide">Sulfacetamide</a></li> <li><a href="/wiki/Tetracycline_antibiotics" title="Tetracycline antibiotics">Tetracyclines</a> (<a href="/wiki/Lymecycline" title="Lymecycline">Lymecycline</a></li> <li><a href="/wiki/Minocycline" title="Minocycline">Minocycline</a></li> <li><a href="/wiki/Doxycycline" title="Doxycycline">Doxycycline</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hormone" title="Hormone">Hormonal</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Antiandrogen" title="Antiandrogen">Antiandrogens</a> <ul><li><a href="/wiki/Bicalutamide" title="Bicalutamide">Bicalutamide</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Drospirenone" title="Drospirenone">Drospirenone</a></li> <li><a href="/wiki/Flutamide" title="Flutamide">Flutamide</a></li> <li><a class="mw-selflink selflink">Spironolactone</a>)</li></ul></li> <li><a href="/wiki/Estrogen" title="Estrogen">Estrogens</a> <ul><li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Retinoid" title="Retinoid">Retinoids</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adapalene" title="Adapalene">Adapalene</a></li> <li><a href="/wiki/Isotretinoin" title="Isotretinoin">Isotretinoin</a></li> <li><a href="/wiki/Motretinide" title="Motretinide">Motretinide</a></li> <li><a href="/wiki/Tazarotene" title="Tazarotene">Tazarotene</a></li> <li><a href="/wiki/Tretinoin" title="Tretinoin">Tretinoin</a></li> <li><a href="/wiki/Trifarotene" title="Trifarotene">Trifarotene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Epristeride" title="Epristeride">Epristeride</a></li> <li><a href="/wiki/Mesulfen" title="Mesulfen">Mesulfen</a></li> <li><a href="/wiki/Pelretin" title="Pelretin">Pelretin</a></li> <li><a href="/wiki/Stridex" title="Stridex">Stridex</a></li> <li><a href="/wiki/Tioxolone" title="Tioxolone">Tioxolone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Combinations</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/Adapalene/benzoyl_peroxide" title="Adapalene/benzoyl peroxide">Adapalene/benzoyl peroxide</a></li> <li><a href="/wiki/Clindamycin/adapalene/benzoyl_peroxide" title="Clindamycin/adapalene/benzoyl peroxide">Clindamycin/adapalene/benzoyl peroxide</a></li> <li><a href="/wiki/Clindamycin/benzoyl_peroxide" title="Clindamycin/benzoyl peroxide">Clindamycin/benzoyl peroxide</a></li> <li><a href="/wiki/Clindamycin/tretinoin" title="Clindamycin/tretinoin">Clindamycin/tretinoin</a></li> <li><a href="/wiki/Erythromycin/benzoyl_peroxide" title="Erythromycin/benzoyl peroxide">Erythromycin/benzoyl peroxide</a></li> <li><a href="/wiki/Erythromycin/isotretinoin" title="Erythromycin/isotretinoin">Erythromycin/isotretinoin</a></li> <li><a href="/wiki/Sulfacetamide/sulfur" title="Sulfacetamide/sulfur">Sulfacetamide/sulfur</a></li> <li><a href="/wiki/Tretinoin/benzoyl_peroxide" title="Tretinoin/benzoyl peroxide">Tretinoin/benzoyl peroxide</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><div class="hlist"> <ul><li>#<a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li>‡<a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li>†<a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li>§Never to phase III</li></ul></li></ul> </div></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_dermatological_preparations_(D11)" 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:Other_dermatological_preparations" title="Template:Other dermatological preparations"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Other_dermatological_preparations" title="Template talk:Other dermatological preparations"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Other_dermatological_preparations" title="Special:EditPage/Template:Other dermatological preparations"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Other_dermatological_preparations_(D11)" style="font-size:114%;margin:0 4em">Other <a href="/wiki/Dermatological" class="mw-redirect" title="Dermatological">dermatological</a> preparations (<a href="/wiki/ATC_code_D11" title="ATC code D11">D11</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Anti-seborrheic" title="Anti-seborrheic">Anti-seborrheics</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Antiandrogen" title="Antiandrogen">Antiandrogens</a> <ul><li><a href="/wiki/Bicalutamide" title="Bicalutamide">Bicalutamide</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 class="mw-selflink selflink">Spironolactone</a></li></ul></li> <li><a href="/wiki/Antifungal" title="Antifungal">Antifungals</a> <ul><li><a href="/wiki/Bifonazole" title="Bifonazole">Bifonazole</a></li> <li><a href="/wiki/Cetrimonium_bromide" title="Cetrimonium bromide">Cetrimonium bromide</a> (<a href="/wiki/Cetrimide" title="Cetrimide">cetrimide</a>)</li> <li><a href="/wiki/Ciclopirox_olamine" class="mw-redirect" title="Ciclopirox olamine">Ciclopirox olamine (ciclopirox)</a></li> <li><a href="/wiki/Climbazole" title="Climbazole">Climbazole</a></li> <li><a href="/wiki/Clotrimazole" title="Clotrimazole">Clotrimazole</a></li> <li><a href="/wiki/Ketoconazole" title="Ketoconazole">Ketoconazole</a></li> <li><a href="/wiki/Miconazole" title="Miconazole">Miconazole</a></li> <li><a href="/wiki/Piroctone_olamine" title="Piroctone olamine">Piroctone olamine</a></li> <li><a href="/wiki/Selenium_disulfide" title="Selenium disulfide">Selenium disulfide (selenium sulfide)</a></li> <li><a href="/w/index.php?title=Xenysalate&action=edit&redlink=1" class="new" title="Xenysalate (page does not exist)">Xenysalate</a></li> <li><a href="/wiki/Zinc_pyrithione" title="Zinc pyrithione">Zinc pyrithione (pyrithione zinc)</a></li></ul></li> <li><a href="/wiki/Antihistamine" title="Antihistamine">Antihistamines</a></li> <li><a href="/wiki/Calcineurin_inhibitor" class="mw-redirect" title="Calcineurin inhibitor">Calcineurin inhibitors</a> <ul><li><a href="/wiki/Cyclosporin" class="mw-redirect" title="Cyclosporin">Cyclosporin</a></li> <li><a href="/wiki/Pimecrolimus" title="Pimecrolimus">Pimecrolimus</a></li> <li><a href="/wiki/Tacrolimus" title="Tacrolimus">Tacrolimus</a></li></ul></li> <li><a href="/wiki/Isotretinoin" title="Isotretinoin">Isotretinoin</a></li> <li><a href="/wiki/Keratolytic" title="Keratolytic">Keratolytics</a> <ul><li><a href="/wiki/Coal_tar" title="Coal tar">Coal tar</a></li> <li><a href="/wiki/Resorcinol" title="Resorcinol">Resorcinol</a></li> <li><a href="/wiki/Salicylic_acid" title="Salicylic acid">Salicylic acid</a></li> <li><a href="/wiki/Sulfur" title="Sulfur">Sulfur</a></li> <li><a href="/wiki/Urea" title="Urea">Urea</a> (<a href="/wiki/Urea-containing_cream" title="Urea-containing cream">urea-containing cream</a>)</li></ul></li> <li><a href="/wiki/Lithium_(medication)" title="Lithium (medication)">Lithium salts</a> <ul><li><a href="/wiki/Lithium_gluconate" class="mw-redirect" title="Lithium gluconate">Lithium gluconate</a></li> <li><a href="/wiki/Lithium_succinate" title="Lithium succinate">Lithium succinate</a></li></ul></li> <li><a href="/wiki/Topical_steroid" title="Topical steroid">Topical corticosteroids</a> (e.g., <a href="/wiki/Hydrocortisone" title="Hydrocortisone">hydrocortisone</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Skin_whitening" title="Skin whitening">Skin lightening</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Hydroquinone" title="Hydroquinone">Hydroquinone</a></li> <li><a href="/wiki/Mequinol" title="Mequinol">Mequinol</a></li> <li><a href="/wiki/Monobenzone" title="Monobenzone">Monobenzone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sun_tanning" title="Sun tanning">Skin darkening</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Afamelanotide" title="Afamelanotide">Afamelanotide</a></li> <li><a href="/wiki/Melanotan_II" title="Melanotan II">Melanotan II</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Anti-inflammatories" class="mw-redirect" title="Anti-inflammatories">Anti-inflammatories</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alitretinoin" title="Alitretinoin">Alitretinoin</a></li> <li><a href="/wiki/Gamma-Linolenic_acid" class="mw-redirect" title="Gamma-Linolenic acid">Gamolenic acid</a></li> <li><a href="/wiki/Oxaceprol" title="Oxaceprol">Oxaceprol</a></li> <li><a href="/wiki/Pimecrolimus" title="Pimecrolimus">Pimecrolimus</a></li> <li><a href="/wiki/Tacrolimus" title="Tacrolimus">Tacrolimus</a></li></ul> <ul><li><a href="/wiki/Topical_steroid" title="Topical steroid">Topical corticosteroids</a> (e.g., <a href="/wiki/Hydrocortisone" title="Hydrocortisone">hydrocortisone</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Management_of_hair_loss" title="Management of hair loss">Alopecia treatments</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/5%CE%B1-Reductase_inhibitor" title="5α-Reductase inhibitor">5α-Reductase inhibitors</a> <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/Finasteride" title="Finasteride">Finasteride</a></li> <li><a href="/wiki/Saw_palmetto_extract" title="Saw palmetto extract">Saw palmetto extract</a></li></ul></li> <li><a href="/wiki/Antiandrogen" title="Antiandrogen">Antiandrogens</a> <ul><li><a href="/wiki/Bicalutamide" title="Bicalutamide">Bicalutamide</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 class="mw-selflink selflink">Spironolactone</a></li> <li><a href="/wiki/Topilutamide" title="Topilutamide">Topilutamide (fluridil)</a></li></ul></li> <li><a href="/wiki/Potassium_channel_opener" title="Potassium channel opener">Potassium channel openers</a> <ul><li><a href="/wiki/Minoxidil" title="Minoxidil">Minoxidil</a></li></ul></li> <li>Others <ul><li><a href="/wiki/Nepidermin" title="Nepidermin">Nepidermin</a></li> <li><a href="/wiki/Ritlecitinib" title="Ritlecitinib">Ritlecitinib</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hair_growth_inhibitor" class="mw-redirect" title="Hair growth inhibitor">Hair growth inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/5%CE%B1-Reductase_inhibitor" title="5α-Reductase inhibitor">5α-Reductase inhibitors</a> <ul><li><a href="/wiki/Dutasteride" title="Dutasteride">Dutasteride</a></li> <li><a href="/wiki/Finasteride" title="Finasteride">Finasteride</a></li></ul></li> <li><a href="/wiki/Antiandrogen" title="Antiandrogen">Antiandrogens</a> <ul><li><a href="/wiki/Bicalutamide" title="Bicalutamide">Bicalutamide</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 class="mw-selflink selflink">Spironolactone</a></li></ul></li> <li><a href="/wiki/Eflornithine" title="Eflornithine">Eflornithine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Abrocitinib" title="Abrocitinib">Abrocitinib</a></li> <li><a href="/wiki/Aminobenzoate" class="mw-redirect" title="Aminobenzoate">Aminobenzoate potassium</a></li> <li><a href="/wiki/Androgen" title="Androgen">Androgens</a> (e.g., <a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">testosterone</a>)</li> <li><a href="/wiki/Benzoylperoxide" class="mw-redirect" title="Benzoylperoxide">Benzoylperoxide</a></li> <li><a href="/wiki/Brimonidine" title="Brimonidine">Brimonidine</a></li> <li><a href="/wiki/Caffeine" title="Caffeine">Caffeine</a></li> <li><a href="/wiki/Calcium_gluconate" title="Calcium gluconate">Calcium gluconate</a></li> <li><a href="/wiki/Collagen" title="Collagen">Collagen</a></li> <li><a href="/wiki/Crisaborole" title="Crisaborole">Crisaborole</a></li> <li><a href="/wiki/Cromoglicic_acid" title="Cromoglicic acid">Cromoglicic acid</a></li> <li><a href="/wiki/Delgocitinib" title="Delgocitinib">Delgocitinib</a></li> <li><a href="/wiki/Deoxycholic_acid" title="Deoxycholic acid">Deoxycholic acid</a></li> <li><a href="/wiki/Diclofenac" title="Diclofenac">Diclofenac</a></li> <li><a href="/wiki/Dupilumab" title="Dupilumab">Dupilumab</a></li> <li><a href="/wiki/Estrogen" title="Estrogen">Estrogens</a> (e.g., <a href="/wiki/Estradiol" title="Estradiol">estradiol</a>)</li> <li><a href="/wiki/Glycopyrronium_bromide" title="Glycopyrronium bromide">Glycopyrronium bromide</a></li> <li><a href="/wiki/Glycopyrronium_tosylate" title="Glycopyrronium tosylate">Glycopyrronium tosylate</a></li> <li><a href="/wiki/Hyaluronic_acid" title="Hyaluronic acid">Hyaluronic acid</a></li> <li><a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">Hydrogen peroxide</a></li> <li><a href="/wiki/Ivermectin" title="Ivermectin">Ivermectin</a></li> <li><a href="/wiki/Lebrikizumab" title="Lebrikizumab">Lebrikizumab</a></li> <li><a href="/wiki/Lokivetmab" title="Lokivetmab">Lokivetmab</a></li> <li><a href="/wiki/Magnesium_sulfate" title="Magnesium sulfate">Magnesium sulfate</a></li> <li><a href="/wiki/Metandienone" title="Metandienone">Metandienone</a></li> <li><a href="/wiki/Nemolizumab" title="Nemolizumab">Nemolizumab</a></li> <li><a href="/wiki/Oclacitinib" title="Oclacitinib">Oclacitinib</a></li> <li><a href="/wiki/Oxymetazoline" title="Oxymetazoline">Oxymetazoline</a></li> <li><a href="/wiki/Povidone-iodine" title="Povidone-iodine">Povidone-iodine</a></li> <li><a href="/wiki/Pregnenolone_acetate" title="Pregnenolone acetate">Pregnenolone acetate</a></li> <li><a href="/wiki/Progestogen" title="Progestogen">Progestogens</a> (e.g., <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a>)</li> <li><a href="/wiki/Ruxolitinib" title="Ruxolitinib">Ruxolitinib</a></li> <li><a href="/wiki/Tiratricol" title="Tiratricol">Tiratricol</a></li> <li><a href="/wiki/Tralokinumab" title="Tralokinumab">Tralokinumab</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Androgens_and_antiandrogens" 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: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_antiandrogens" 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> (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)</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 <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>Testosterone derivatives: <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>#</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>Dihydrotestosterone derivatives: <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>19-Nortestosterone derivatives: <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>17α-Alkylated testosterone derivatives: <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>17α-Alkylated dihydrotestosterone derivatives: <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>17α-Alkylated 19-nortestosterone derivatives: <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>17α-Vinyltestosterone derivatives: <a href="/wiki/Norvinisterone" title="Norvinisterone">Norvinisterone (vinylnortestosterone)</a></li></ul> <ul><li>17α-Ethynyltestosterone derivatives: <a href="/wiki/Danazol" title="Danazol">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>Progesterone derivatives: <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, <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)</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 <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>Steroidal: <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 class="mw-selflink selflink">Spironolactone</a></li></ul> <ul><li>Nonsteroidal: <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>†</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 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>†</li> <li><a class="mw-selflink selflink">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">D2 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>Androstenedione immunogens: <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>#<a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li>‡<a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li>†<a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li>§Never to phase III</li></ul></li></ul> </div> <dl><dt>See also</dt> <dd><a href="/wiki/Template: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="Mineralocorticoids_and_antimineralocorticoids_(H02)" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Mineralocorticoids_and_antimineralocorticoids" title="Template:Mineralocorticoids and antimineralocorticoids"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Mineralocorticoids_and_antimineralocorticoids" title="Template talk:Mineralocorticoids and antimineralocorticoids"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Mineralocorticoids_and_antimineralocorticoids" title="Special:EditPage/Template:Mineralocorticoids and antimineralocorticoids"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Mineralocorticoids_and_antimineralocorticoids_(H02)" style="font-size:114%;margin:0 4em"><a href="/wiki/Mineralocorticoid" title="Mineralocorticoid">Mineralocorticoids</a> and <a href="/wiki/Antimineralocorticoid" class="mw-redirect" title="Antimineralocorticoid">antimineralocorticoids</a> (<a href="/wiki/ATC_code_H02" title="ATC code H02">H02</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Mineralocorticoid" title="Mineralocorticoid">Mineralocorticoids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Deoxycortone" class="mw-redirect" title="Deoxycortone">Desoxycortone (desoxycorticosterone)</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Desoxycortone_esters" title="List of corticosteroid esters">Desoxycortone esters</a></li></ul></li> <li><a href="/wiki/Hydrocortisone" title="Hydrocortisone">Hydrocortisone (cortisol)</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Hydrocortisone_esters" title="List of corticosteroid esters">Hydrocortisone esters</a></li></ul></li> <li><a href="/wiki/Fludrocortisone" title="Fludrocortisone">Fludrocortisone</a> <ul><li><a href="/wiki/Fludrocortisone_acetate" class="mw-redirect" title="Fludrocortisone acetate">Fludrocortisone acetate</a></li></ul></li> <li><a href="/wiki/Methylprednisolone" title="Methylprednisolone">Methylprednisolone</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Methylprednisolone_esters" title="List of corticosteroid esters">Methylprednisolone esters</a></li></ul></li> <li><a href="/wiki/Prednisolone" title="Prednisolone">Prednisolone</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Prednisolone_esters" title="List of corticosteroid esters">Prednisolone esters</a></li></ul></li> <li><a href="/wiki/Prednisone" title="Prednisone">Prednisone</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Prednisone_esters" title="List of corticosteroid esters">Prednisone esters</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Antimineralocorticoid" class="mw-redirect" title="Antimineralocorticoid">Antimineralocorticoids</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Steroidal: <a href="/wiki/Potassium_canrenoate" title="Potassium canrenoate">Canrenoate potassium (potassium canrenoate)</a></li> <li><a href="/wiki/Canrenone" title="Canrenone">Canrenone</a></li> <li><a href="/wiki/Drospirenone" title="Drospirenone">Drospirenone</a></li> <li><a href="/wiki/Dydrogesterone" title="Dydrogesterone">Dydrogesterone</a></li> <li><a href="/wiki/Eplerenone" title="Eplerenone">Eplerenone</a></li> <li><a href="/wiki/Gestodene" title="Gestodene">Gestodene</a></li> <li><a href="/wiki/Medrogestone" title="Medrogestone">Medrogestone</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a class="mw-selflink selflink">Spironolactone</a></li> <li><a href="/wiki/Trimegestone" title="Trimegestone">Trimegestone</a></li></ul> <ul><li>Nonsteroidal: <a href="/wiki/Amlodipine" title="Amlodipine">Amlodipine</a></li> <li><a href="/wiki/Apararenone" title="Apararenone">Apararenone</a>§</li> <li><a href="/wiki/Benidipine" title="Benidipine">Benidipine</a></li> <li><a href="/wiki/Esaxerenone" title="Esaxerenone">Esaxerenone</a>†</li> <li><a href="/wiki/Felodipine" title="Felodipine">Felodipine</a></li> <li><a href="/wiki/Finerenone" title="Finerenone">Finerenone</a></li> <li><a href="/wiki/Nifedipine" title="Nifedipine">Nifedipine</a></li> <li><a href="/wiki/Nimodipine" title="Nimodipine">Nimodipine</a></li> <li><a href="/wiki/Nitrendipine" title="Nitrendipine">Nitrendipine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Steroidogenesis_inhibitor" title="Steroidogenesis inhibitor">Synthesis modifiers</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetoxolone" title="Acetoxolone">Acetoxolone</a></li> <li><a href="/wiki/Aminoglutethimide" title="Aminoglutethimide">Aminoglutethimide</a></li> <li><a href="/wiki/Carbenoxolone" title="Carbenoxolone">Carbenoxolone</a></li> <li><a href="/wiki/Enoxolone" title="Enoxolone">Enoxolone</a></li> <li><a href="/wiki/Ketoconazole" title="Ketoconazole">Ketoconazole</a></li> <li><a href="/wiki/Metyrapone" title="Metyrapone">Metyrapone</a></li> <li><a href="/wiki/Mitotane" title="Mitotane">Mitotane</a></li> <li><a href="/wiki/Trilostane" title="Trilostane">Trilostane</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><div class="hlist"> <ul><li>#<a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li>‡<a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li>†<a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li>§Never to phase III</li></ul></li></ul> </div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Mineralocorticoid_receptor_modulators" title="Template:Mineralocorticoid receptor modulators">Mineralocorticoid receptor modulators</a></dd> <dd><a href="/wiki/Template:Glucocorticoids_and_antiglucocorticoids" title="Template:Glucocorticoids and antiglucocorticoids">Glucocorticoids and antiglucocorticoids</a></dd> <dd><a href="/wiki/List_of_corticosteroids" title="List of corticosteroids">List of corticosteroids</a></dd></dl></div></td></tr></tbody></table></div></div></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="Pharmacodynamics" 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="Pharmacodynamics" 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_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template: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_modulators" 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</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>Testosterone derivatives: <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># (<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>5α-Dihydrotestosterone derivatives: <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>19-Nortestosterone derivatives: <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-N-(2-chloroethyl)-N-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>5α-Dihydro-19-nortestosterone derivatives: <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>17α-Alkylated testosterone derivatives: <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>17α-Alkylated 5α-dihydrotestosterone derivatives: <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>17α-Alkylated 19-nortestosterone derivatives: <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>17α-Alkylated 5α-dihydro-19-nortestosterone derivatives: <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>17α-Vinyltestosterone derivatives: <a href="/wiki/Norvinisterone" title="Norvinisterone">Norvinisterone (vinylnortestosterone)</a></li></ul> <ul><li>17α-Vinyl-19-nortestosterone derivatives: <a href="/wiki/Vinyltestosterone" title="Vinyltestosterone">Vinyltestosterone</a></li></ul> <ul><li>17α-Ethynyltestosterone derivatives: <a href="/wiki/Danazol" title="Danazol">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>5α-Dihydro-17α-ethynyltestosterone derivatives: <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>17α-Ethynyl-19-nortestosterone derivatives: <a href="/wiki/%CE%944-Tibolone" title="Δ4-Tibolone">Δ4-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>5α-Dihydro-17α-ethynyl-19-nortestosterone derivatives: <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>Progesterone derivatives: <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>Others/unsorted: <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</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Nonsteroidal: <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>Steroidal: <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>Steroidal: <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 class="mw-selflink selflink">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>Nonsteroidal: <a href="/wiki/5N-Bicalutamide" title="5N-Bicalutamide">5N-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)">N-Butylbenzenesulfonamide</a></li> <li><a href="/wiki/N-Desmethylapalutamide" title="N-Desmethylapalutamide">N-Desmethylapalutamide</a></li> <li><a href="/wiki/N-Desmethylenzalutamide" title="N-Desmethylenzalutamide">N-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">L-α-Amino acids</a> (incl. <a href="/wiki/Arginine" title="Arginine">L-arginine</a>, <a href="/wiki/Lysine" title="Lysine">L-lysine</a>, <a href="/wiki/Ornithine" title="Ornithine">L-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</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_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Estrogen_receptor_modulators" title="Template talk:Estrogen receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Estrogen_receptor_modulators" title="Special:EditPage/Template:Estrogen receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Estrogen_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor">Estrogen receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor</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>Steroidal: <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">ent-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>Nonsteroidal: <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">meso-Butestrol</a></li> <li><a href="/wiki/Meso-Hexestrol" class="mw-redirect" title="Meso-Hexestrol">meso-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>Unknown/unsorted: <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>Xenoestrogens: <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 (cis-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 (<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)</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 class="mw-selflink selflink">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>Coregulator-binding modulators: <a href="/wiki/ERX-11" title="ERX-11">ERX-11</a></li></ul> <ul><li>Noncompetitive inhibitors: <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</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Methoxyestradiol" title="2-Methoxyestradiol">2-Methoxyestradiol</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/Afimoxifene" title="Afimoxifene">Afimoxifene (4-hydroxytamoxifen)</a></li> <li><a href="/wiki/Aldosterone" title="Aldosterone">Aldosterone</a></li> <li><a href="/wiki/Atrazine" title="Atrazine">Atrazine</a></li> <li><a href="/wiki/Bisphenol_A" title="Bisphenol A">Bisphenol A</a></li> <li><a href="/wiki/Daidzein" title="Daidzein">Daidzein</a></li> <li><a href="/wiki/DDT" title="DDT">DDT</a> (<a href="/wiki/P,p%27-DDT" class="mw-redirect" title="P,p'-DDT">p,p'-DDT</a>, <a href="/w/index.php?title=O%27,p%27-DDE&action=edit&redlink=1" class="new" title="O',p'-DDE (page does not exist)">o',p'-DDE</a>)</li> <li><a href="/wiki/Diarylpropionitrile" title="Diarylpropionitrile">Diarylpropionitrile</a></li> <li><a href="/wiki/Equol" title="Equol">Equol</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a></li> <li><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant (ICI-182780)</a></li> <li><a href="/w/index.php?title=G-1_(drug)&action=edit&redlink=1" class="new" title="G-1 (drug) (page does not exist)">G-1</a></li> <li><a href="/wiki/Genistein" title="Genistein">Genistein</a></li> <li><a href="/w/index.php?title=GPER-L1&action=edit&redlink=1" class="new" title="GPER-L1 (page does not exist)">GPER-L1</a></li> <li><a href="/w/index.php?title=GPER-L2&action=edit&redlink=1" class="new" title="GPER-L2 (page does not exist)">GPER-L2</a></li> <li><a href="/wiki/Hydroxytyrosol" title="Hydroxytyrosol">Hydroxytyrosol</a></li> <li><a href="/wiki/Kepone" class="mw-redirect" title="Kepone">Kepone</a></li> <li><a href="/wiki/Niacin" title="Niacin">Niacin</a></li> <li><a href="/wiki/Niacinamide" class="mw-redirect" title="Niacinamide">Niacinamide</a></li> <li><a href="/wiki/Nonylphenol" title="Nonylphenol">Nonylphenol</a></li> <li><a href="/wiki/Oleuropein" title="Oleuropein">Oleuropein</a></li> <li><a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">PCBs</a> (<a href="/w/index.php?title=2,2%27,5%27-PCB-4-OH&action=edit&redlink=1" class="new" title="2,2',5'-PCB-4-OH (page does not exist)">2,2',5'-PCB-4-OH</a>)</li> <li><a href="/wiki/Propylpyrazoletriol" title="Propylpyrazoletriol">Propylpyrazoletriol</a></li> <li><a href="/wiki/Quercetin" title="Quercetin">Quercetin</a></li> <li><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></li> <li><a href="/wiki/Resveratrol" title="Resveratrol">Resveratrol</a></li> <li><a href="/w/index.php?title=STX_(drug)&action=edit&redlink=1" class="new" title="STX (drug) (page does not exist)">STX</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a></li> <li><a href="/wiki/Tectoridin" title="Tectoridin">Tectoridin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/CCL18" title="CCL18">CCL18</a></li> <li><a href="/wiki/Estriol" title="Estriol">Estriol</a></li> <li><a href="/w/index.php?title=G-15_(drug)&action=edit&redlink=1" class="new" title="G-15 (drug) (page does not exist)">G-15</a></li> <li><a href="/w/index.php?title=G-36_(drug)&action=edit&redlink=1" class="new" title="G-36 (drug) (page does not exist)">G-36</a></li> <li><a href="/wiki/MIBE" title="MIBE">MIBE</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Unknown</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a></li> <li><a href="/wiki/Zearalenone" title="Zearalenone">Zearalenone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Estrogens_and_antiestrogens" title="Template:Estrogens and antiestrogens">Estrogens and antiestrogens</a></dd> <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="Mineralocorticoid_receptor_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Mineralocorticoid_receptor_modulators" title="Template:Mineralocorticoid receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Mineralocorticoid_receptor_modulators" title="Template talk:Mineralocorticoid receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Mineralocorticoid_receptor_modulators" title="Special:EditPage/Template:Mineralocorticoid receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Mineralocorticoid_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Mineralocorticoid_receptor" title="Mineralocorticoid receptor">Mineralocorticoid receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Mineralocorticoid_receptor" title="Mineralocorticoid receptor"><abbr title="Mineralocorticoid receptor">MR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Mineralocorticoid receptor</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/11-Dehydrocorticosterone" title="11-Dehydrocorticosterone">11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone)</a> <ul><li><a href="/w/index.php?title=11-Dehydrocorticosterone_acetate&action=edit&redlink=1" class="new" title="11-Dehydrocorticosterone acetate (page does not exist)">11-Dehydrocorticosterone acetate</a></li></ul></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone (desoxycortone, deoxycortone, desoxycorticosterone)</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Desoxycortone_esters" title="List of corticosteroid esters">Desoxycortone esters</a></li></ul></li> <li><a href="/wiki/11-Deoxycortisol" title="11-Deoxycortisol">11-Deoxycortisol (cortodoxone, cortexolone)</a> <ul><li><a href="/wiki/Cortifen" title="Cortifen">Cortifen (cortiphen, kortifen)</a></li> <li><a href="/w/index.php?title=Cortodoxone_acetate&action=edit&redlink=1" class="new" title="Cortodoxone acetate (page does not exist)">Cortodoxone acetate</a></li></ul></li> <li><a href="/wiki/11%CE%B2-Hydroxyprogesterone" title="11β-Hydroxyprogesterone">11β-Hydroxyprogesterone</a></li> <li><a href="/w/index.php?title=16%CE%B1,18-Dihydroxy-11-deoxycorticosterone&action=edit&redlink=1" class="new" title="16α,18-Dihydroxy-11-deoxycorticosterone (page does not exist)">16α,18-Dihydroxy-11-deoxycorticosterone</a></li> <li><a href="/w/index.php?title=17%CE%B1-Hydroxyaldosterone&action=edit&redlink=1" class="new" title="17α-Hydroxyaldosterone (page does not exist)">17α-Hydroxyaldosterone</a></li> <li><a href="/wiki/18-Hydroxy-11-deoxycorticosterone" title="18-Hydroxy-11-deoxycorticosterone">18-Hydroxy-11-deoxycorticosterone</a></li> <li><a href="/wiki/19-Norprogesterone" title="19-Norprogesterone">19-Norprogesterone</a></li> <li><a href="/wiki/Aldosterone" title="Aldosterone">Aldosterone</a></li> <li><a href="/wiki/Corticosterone" title="Corticosterone">Corticosterone</a> <ul><li><a href="/w/index.php?title=Corticosterone_acetate&action=edit&redlink=1" class="new" title="Corticosterone acetate (page does not exist)">Corticosterone acetate</a></li> <li><a href="/w/index.php?title=Corticosterone_benzoate&action=edit&redlink=1" class="new" title="Corticosterone benzoate (page does not exist)">Corticosterone benzoate</a></li></ul></li> <li><a href="/wiki/Cortisol" title="Cortisol">Cortisol</a> (<a href="/wiki/Hydrocortisone" title="Hydrocortisone">hydrocortisone</a>) <ul><li><a href="/wiki/Benzodrocortisone" title="Benzodrocortisone">Benzodrocortisone (hydrocortisone benzoate)</a></li> <li><a href="/wiki/Hydrocortamate" title="Hydrocortamate">Hydrocortamate (hydrocortisone diethylaminoacetate)</a></li> <li><a href="/wiki/List_of_corticosteroid_esters#Hydrocortisone_esters" title="List of corticosteroid esters">Hydrocortisone esters</a></li></ul></li> <li><a href="/wiki/Cortisone" title="Cortisone">Cortisone</a> <ul><li><a href="/wiki/Cortisone_acetate" title="Cortisone acetate">Cortisone acetate</a></li></ul></li> <li><a href="/wiki/Fludrocortisone" title="Fludrocortisone">Fludrocortisone (fludrocortone)</a> <ul><li><a href="/wiki/Fludrocortisone_acetate" class="mw-redirect" title="Fludrocortisone acetate">Fludrocortisone acetate</a></li></ul></li> <li><a href="/wiki/Mometasone" title="Mometasone">Mometasone</a> <ul><li><a href="/wiki/Mometasone_furoate" class="mw-redirect" title="Mometasone furoate">Mometasone furoate</a></li></ul></li> <li><a href="/wiki/Prednisolone" title="Prednisolone">Prednisolone</a> <ul><li><a href="/wiki/Prednazate" title="Prednazate">Prednazate</a></li> <li><a href="/wiki/Prednazoline" title="Prednazoline">Prednazoline</a></li> <li><a href="/wiki/Prednicarbate" title="Prednicarbate">Prednicarbate (prednisolone ethylcarbonate propionate)</a></li> <li><a href="/wiki/Prednimustine" title="Prednimustine">Prednimustine</a></li> <li><a href="/wiki/Prednisolamate" title="Prednisolamate">Prednisolamate (prednisolone diethylaminoacetate)</a></li> <li><a href="/wiki/List_of_corticosteroid_esters#Prednisolone_esters" title="List of corticosteroid esters">Prednisolone esters</a></li></ul></li> <li><a href="/wiki/Prednisone" title="Prednisone">Prednisone</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Prednisone_esters" title="List of corticosteroid esters">Prednisone esters</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Steroidal: <a href="/wiki/6%CE%B2-Hydroxy-7%CE%B1-thiomethylspironolactone" title="6β-Hydroxy-7α-thiomethylspironolactone">6β-Hydroxy-7α-thiomethylspironolactone</a></li> <li><a href="/w/index.php?title=7%CE%B1-Acetylthio-17%CE%B1-hydroxyprogesterone&action=edit&redlink=1" class="new" title="7α-Acetylthio-17α-hydroxyprogesterone (page does not exist)">7α-Acetylthio-17α-hydroxyprogesterone</a></li> <li><a href="/wiki/7%CE%B1-Thiomethylspironolactone" title="7α-Thiomethylspironolactone">7α-Thiomethylspironolactone (SC-26519)</a></li> <li><a href="/wiki/7%CE%B1-Thioprogesterone" title="7α-Thioprogesterone">7α-Thioprogesterone (SC-8365)</a></li> <li><a href="/wiki/7%CE%B1-Thiospironolactone" title="7α-Thiospironolactone">7α-Thiospironolactone (SC-24813)</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyprogesterone" title="16α-Hydroxyprogesterone">16α-Hydroxyprogesterone</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone (hydroxyprogesterone)</a></li> <li><a href="/wiki/18-Deoxyaldosterone" title="18-Deoxyaldosterone">18-Deoxyaldosterone</a></li> <li><a href="/w/index.php?title=18,19-Dinorprogesterone&action=edit&redlink=1" class="new" title="18,19-Dinorprogesterone (page does not exist)">18,19-Dinorprogesterone</a></li> <li><a href="/wiki/Potassium_canrenoate" title="Potassium canrenoate">Canrenoate potassium (potassium canrenoate)</a></li> <li><a href="/wiki/Canrenoic_acid" title="Canrenoic acid">Canrenoic acid (canrenoate)</a></li> <li><a href="/wiki/Canrenone" title="Canrenone">Canrenone (canrenoate y-lactone)</a></li> <li><a href="/wiki/Dicirenone" title="Dicirenone">Dicirenone</a></li> <li><a href="/wiki/Dimethisterone" title="Dimethisterone">Dimethisterone</a></li> <li><a href="/wiki/Drospirenone" title="Drospirenone">Drospirenone</a></li> <li><a href="/wiki/Dydrogesterone" title="Dydrogesterone">Dydrogesterone</a></li> <li><a href="/wiki/Eplerenone" title="Eplerenone">Eplerenone</a></li> <li><a href="/wiki/Gestodene" title="Gestodene">Gestodene</a></li> <li><a href="/wiki/Guggulsterone" title="Guggulsterone">Guggulsterone</a></li> <li><a href="/wiki/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">Hydroxyprogesterone caproate</a></li> <li><a href="/wiki/Medrogestone" title="Medrogestone">Medrogestone</a></li> <li><a href="/wiki/Mespirenone" title="Mespirenone">Mespirenone</a></li> <li><a href="/wiki/Metribolone" title="Metribolone">Metribolone</a></li> <li><a href="/wiki/Mexrenoate_potassium" title="Mexrenoate potassium">Mexrenoate potassium</a></li> <li><a href="/wiki/Mexrenoic_acid" title="Mexrenoic acid">Mexrenoic acid (mexrenoate)</a></li> <li><a href="/wiki/Mexrenone" title="Mexrenone">Mexrenone</a></li> <li><a href="/wiki/Oxprenoic_acid" title="Oxprenoic acid">Oxprenoic acid (oxprenoate)</a></li> <li><a href="/wiki/Oxprenoate_potassium" title="Oxprenoate potassium">Oxprenoate potassium (RU-28318)</a></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Prorenoate_potassium" title="Prorenoate potassium">Prorenoate potassium</a></li> <li><a href="/wiki/Prorenoic_acid" title="Prorenoic acid">Prorenoic acid (prorenoate)</a></li> <li><a href="/wiki/Prorenone" title="Prorenone">Prorenone</a></li> <li><a href="/w/index.php?title=RO-14-9012&action=edit&redlink=1" class="new" title="RO-14-9012 (page does not exist)">RO-14-9012</a></li> <li><a href="/w/index.php?title=RU-26752&action=edit&redlink=1" class="new" title="RU-26752 (page does not exist)">RU-26752</a></li> <li><a href="/wiki/SC-5233" title="SC-5233">SC-5233 (spirolactone)</a></li> <li><a href="/wiki/SC-8109" title="SC-8109">SC-8109</a></li> <li><a href="/w/index.php?title=SC-11927&action=edit&redlink=1" class="new" title="SC-11927 (page does not exist)">SC-11927 (CS-1)</a></li> <li><a href="/w/index.php?title=SC-19886&action=edit&redlink=1" class="new" title="SC-19886 (page does not exist)">SC-19886</a></li> <li><a href="/w/index.php?title=SC-27169&action=edit&redlink=1" class="new" title="SC-27169 (page does not exist)">SC-27169</a></li> <li><a href="/wiki/Spirorenone" title="Spirorenone">Spirorenone</a></li> <li><a class="mw-selflink selflink">Spironolactone</a></li> <li><a href="/wiki/Spiroxasone" title="Spiroxasone">Spiroxasone</a></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li> <li><a href="/wiki/Trimegestone" title="Trimegestone">Trimegestone</a></li> <li><a href="/wiki/Vamorolone" title="Vamorolone">Vamorolone</a></li> <li><a href="/w/index.php?title=ZK-91587&action=edit&redlink=1" class="new" title="ZK-91587 (page does not exist)">ZK-91587</a></li> <li><a href="/w/index.php?title=ZK-97894&action=edit&redlink=1" class="new" title="ZK-97894 (page does not exist)">ZK-97894</a></li></ul> <ul><li>Nonsteroidal: <a href="/wiki/Amlodipine" title="Amlodipine">Amlodipine</a></li> <li><a href="/wiki/Apararenone" title="Apararenone">Apararenone</a></li> <li><a href="/wiki/Benidipine" title="Benidipine">Benidipine</a></li> <li><a href="/w/index.php?title=BR-4628&action=edit&redlink=1" class="new" title="BR-4628 (page does not exist)">BR-4628</a></li> <li><a href="/wiki/Esaxerenone" title="Esaxerenone">Esaxerenone</a></li> <li><a href="/wiki/Felodipine" title="Felodipine">Felodipine</a></li> <li><a href="/wiki/Finerenone" title="Finerenone">Finerenone</a></li> <li><a href="/wiki/Miricorilant" title="Miricorilant">Miricorilant (CORT-118335)</a></li> <li><a href="/wiki/Nifedipine" title="Nifedipine">Nifedipine</a></li> <li><a href="/wiki/Nimodipine" title="Nimodipine">Nimodipine</a></li> <li><a href="/wiki/Nitrendipine" title="Nitrendipine">Nitrendipine</a></li> <li><a href="/wiki/Ocedurenone" title="Ocedurenone">Ocedurenone</a></li> <li><a href="/w/index.php?title=PF-03882845&action=edit&redlink=1" class="new" title="PF-03882845 (page does not exist)">PF-03882845</a></li> <li><a href="/w/index.php?title=SM-368229&action=edit&redlink=1" class="new" title="SM-368229 (page does not exist)">SM-368229</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Mineralocorticoids_and_antimineralocorticoids" title="Template:Mineralocorticoids and antimineralocorticoids">Mineralocorticoids and antimineralocorticoids</a></dd> <dd><a href="/wiki/Template:Glucocorticoid_receptor_modulators" title="Template:Glucocorticoid receptor modulators">Glucocorticoid receptor modulators</a></dd> <dd><a href="/wiki/List_of_corticosteroids" title="List of corticosteroids">List of corticosteroids</a></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Progesterone_receptor_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template: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_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Progesterone_receptor" title="Progesterone receptor">Progesterone receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Progesterone_receptor" title="Progesterone receptor"><abbr title="Progesterone receptor">PR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Progesterone receptor</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Progesterone derivatives: <a href="/wiki/3%CE%B2-Dihydroprogesterone" title="3β-Dihydroprogesterone">3β-Dihydroprogesterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">5α-Dihydroprogesterone</a></li> <li><a href="/wiki/6%CE%B1-Methylprogesterone" title="6α-Methylprogesterone">6α-Methylprogesterone</a></li> <li><a href="/wiki/9%CE%B1-Bromo-11-ketoprogesterone" class="mw-redirect" title="9α-Bromo-11-ketoprogesterone">9α-Bromo-11-ketoprogesterone</a></li> <li><a href="/wiki/11-Dehydroprogesterone" title="11-Dehydroprogesterone">11-Dehydroprogesterone</a></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyprogesterone" title="16α-Hydroxyprogesterone">16α-Hydroxyprogesterone</a></li> <li><a href="/w/index.php?title=17%CE%B1-Methyl-11-deoxycorticosterone_acetate&action=edit&redlink=1" class="new" title="17α-Methyl-11-deoxycorticosterone acetate (page does not exist)">17α-Methyl-11-deoxycorticosterone acetate</a></li> <li><a href="/wiki/20%CE%B1-Dihydroprogesterone" title="20α-Dihydroprogesterone">20α-Dihydroprogesterone</a></li> <li><a href="/wiki/20%CE%B2-Dihydroprogesterone" title="20β-Dihydroprogesterone">20β-Dihydroprogesterone</a></li> <li><a href="/wiki/Dimepregnen" title="Dimepregnen">Dimepregnen</a></li> <li><a href="/wiki/Diosgenin" title="Diosgenin">Diosgenin</a></li> <li><a href="/wiki/P1-185" title="P1-185">P1-185</a></li> <li><a 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>Retroprogesterone derivatives: <a href="/wiki/20%CE%B1-Dihydrodydrogesterone" title="20α-Dihydrodydrogesterone">20α-Dihydrodydrogesterone</a></li> <li><a href="/wiki/20%CE%B1-Dihydrotrengestone" title="20α-Dihydrotrengestone">20α-Dihydrotrengestone</a></li> <li><a href="/wiki/DU-41164" title="DU-41164">DU-41164</a></li> <li><a href="/wiki/DU-41165" title="DU-41165">DU-41165</a></li> <li><a href="/wiki/Dydrogesterone" title="Dydrogesterone">Dydrogesterone</a></li> <li><a href="/wiki/Retroprogesterone" title="Retroprogesterone">Retroprogesterone</a></li> <li><a href="/wiki/Ro_6-3129" title="Ro 6-3129">Ro 6-3129</a></li> <li><a href="/wiki/Trengestone" title="Trengestone">Trengestone</a></li></ul> <ul><li>17α-Substituted progesterone derivatives: <a href="/wiki/6%CE%B1-Methyl-17%CE%B1-bromoprogesterone" title="6α-Methyl-17α-bromoprogesterone">6α-Methyl-17α-bromoprogesterone</a></li> <li><a href="/wiki/15%CE%B2-Hydroxycyproterone_acetate" title="15β-Hydroxycyproterone acetate">15β-Hydroxycyproterone acetate</a></li> <li><a href="/wiki/16-Methylene-17%CE%B1-hydroxyprogesterone_acetate" title="16-Methylene-17α-hydroxyprogesterone acetate">16-Methylene-17α-hydroxyprogesterone acetate</a></li> <li><a href="/wiki/17%CE%B1-Bromoprogesterone" title="17α-Bromoprogesterone">17α-Bromoprogesterone</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone (hydroxyprogesterone)</a></li> <li><a href="/wiki/17%CE%B1-Methylprogesterone" title="17α-Methylprogesterone">17α-Methylprogesterone</a></li> <li><a href="/wiki/Acetomepregenol" title="Acetomepregenol">Acetomepregenol (mepregenol diacetate)</a></li> <li><a href="/wiki/Algestone" title="Algestone">Algestone</a></li> <li><a href="/wiki/Algestone_acetonide" title="Algestone acetonide">Algestone acetonide</a></li> <li><a href="/wiki/Algestone_acetophenide" title="Algestone acetophenide">Algestone acetophenide</a></li> <li><a href="/wiki/Anagestone" title="Anagestone">Anagestone</a></li> <li><a href="/wiki/Anagestone_acetate" title="Anagestone acetate">Anagestone acetate</a></li> <li><a href="/w/index.php?title=Bromethenmadinone&action=edit&redlink=1" class="new" title="Bromethenmadinone (page does not exist)">Bromethenmadinone</a></li> <li><a href="/wiki/Bromethenmadinone_acetate" title="Bromethenmadinone acetate">Bromethenmadinone acetate</a></li> <li><a href="/wiki/Butagest" title="Butagest">Butagest (buterol)</a></li> <li><a href="/wiki/Chlormadinone" title="Chlormadinone">Chlormadinone</a></li> <li><a href="/wiki/Chlormadinone_acetate" title="Chlormadinone acetate">Chlormadinone acetate</a></li> <li><a href="/wiki/Chlormadinone_caproate" title="Chlormadinone caproate">Chlormadinone caproate</a></li> <li><a href="/w/index.php?title=Chlormethenmadinone&action=edit&redlink=1" class="new" title="Chlormethenmadinone (page does not exist)">Chlormethenmadinone</a></li> <li><a href="/wiki/Chlormethenmadinone_acetate" title="Chlormethenmadinone acetate">Chlormethenmadinone acetate</a></li> <li><a href="/wiki/Cismadinone" title="Cismadinone">Cismadinone</a></li> <li><a href="/wiki/Cismadinone_acetate" title="Cismadinone acetate">Cismadinone acetate</a></li> <li><a href="/wiki/Clogestone" title="Clogestone">Clogestone</a></li> <li><a href="/wiki/Clogestone_acetate" title="Clogestone acetate">Clogestone acetate</a></li> <li><a href="/wiki/Clomegestone" title="Clomegestone">Clomegestone</a></li> <li><a href="/wiki/Clomegestone_acetate" title="Clomegestone acetate">Clomegestone acetate</a></li> <li><a href="/wiki/Cymegesolate" title="Cymegesolate">Cymegesolate</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Delmadinone" title="Delmadinone">Delmadinone</a></li> <li><a href="/wiki/Delmadinone_acetate" title="Delmadinone acetate">Delmadinone acetate</a></li> <li><a href="/wiki/Edogestrone" title="Edogestrone">Edogestrone</a></li> <li><a href="/wiki/Flugestone" title="Flugestone">Flugestone</a></li> <li><a href="/wiki/Flugestone_acetate" title="Flugestone acetate">Flugestone acetate</a></li> <li><a href="/wiki/Fluorometholone" title="Fluorometholone">Fluorometholone</a></li> <li><a href="/wiki/Fluorometholone_acetate" title="Fluorometholone acetate">Fluorometholone acetate</a></li> <li><a href="/wiki/Flumedroxone" title="Flumedroxone">Flumedroxone</a></li> <li><a href="/wiki/Flumedroxone_acetate" title="Flumedroxone acetate">Flumedroxone acetate</a></li> <li><a href="/wiki/Fluoromedroxyprogesterone_acetate" title="Fluoromedroxyprogesterone acetate">Fluoromedroxyprogesterone acetate</a></li> <li><a href="/wiki/Gestaclone" title="Gestaclone">Gestaclone</a></li> <li><a href="/w/index.php?title=Gestobutanoyl&action=edit&redlink=1" class="new" title="Gestobutanoyl (page does not exist)">Gestobutanoyl</a></li> <li><a href="/wiki/Haloprogesterone" title="Haloprogesterone">Haloprogesterone</a></li> <li><a href="/wiki/Hydromadinone" title="Hydromadinone">Hydromadinone</a></li> <li><a href="/wiki/Hydromadinone_acetate" title="Hydromadinone acetate">Hydromadinone acetate</a></li> <li><a href="/wiki/Hydroxyprogesterone_acetate" title="Hydroxyprogesterone acetate">Hydroxyprogesterone acetate</a></li> <li><a href="/wiki/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">Hydroxyprogesterone caproate (hydroxyprogesterone hexanoate)</a></li> <li><a href="/wiki/Hydroxyprogesterone_heptanoate" title="Hydroxyprogesterone heptanoate">Hydroxyprogesterone heptanoate (hydroxyprogesterone enanthate)</a></li> <li><a href="/wiki/Hydroxyprogesterone_heptanoate_benzilic_acid_hydrazone" title="Hydroxyprogesterone heptanoate benzilic acid hydrazone">Hydroxyprogesterone heptanoate benzilic acid hydrazone</a></li> <li><a href="/wiki/Mecigestone" title="Mecigestone">Mecigestone (pentarane B)</a></li> <li><a href="/wiki/Medrogestone" title="Medrogestone">Medrogestone</a></li> <li><a href="/wiki/Medroxyprogesterone" title="Medroxyprogesterone">Medroxyprogesterone</a></li> <li><a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">Medroxyprogesterone acetate</a></li> <li><a href="/wiki/Medroxyprogesterone_caproate" title="Medroxyprogesterone caproate">Medroxyprogesterone caproate</a></li> <li><a href="/wiki/Megestrol" title="Megestrol">Megestrol</a></li> <li><a href="/wiki/Megestrol_acetate" title="Megestrol acetate">Megestrol acetate</a></li> <li><a href="/wiki/Megestrol_caproate" title="Megestrol caproate">Megestrol caproate</a></li> <li><a href="/wiki/Melengestrol" title="Melengestrol">Melengestrol</a></li> <li><a href="/wiki/Melengestrol_acetate" title="Melengestrol acetate">Melengestrol acetate</a></li> <li><a href="/wiki/Methenmadinone" title="Methenmadinone">Methenmadinone</a></li> <li><a href="/wiki/Methenmadinone_acetate" title="Methenmadinone acetate">Methenmadinone acetate</a></li> <li><a href="/wiki/Methenmadinone_caproate" title="Methenmadinone caproate">Methenmadinone caproate</a></li> <li><a href="/wiki/Mometasone" title="Mometasone">Mometasone</a></li> <li><a href="/wiki/Mometasone_furoate" class="mw-redirect" title="Mometasone furoate">Mometasone furoate</a></li> <li><a href="/wiki/Osaterone" title="Osaterone">Osaterone</a></li> <li><a href="/wiki/Osaterone_acetate" title="Osaterone acetate">Osaterone acetate</a></li> <li><a href="/wiki/Pentagestrone" title="Pentagestrone">Pentagestrone</a></li> <li><a href="/wiki/Pentagestrone_acetate" title="Pentagestrone acetate">Pentagestrone acetate</a></li> <li><a href="/wiki/Pentarane_A" title="Pentarane A">Pentarane A</a></li> <li><a href="/wiki/Proligestone" title="Proligestone">Proligestone</a></li> <li><a href="/wiki/Triamcinolone_acetonide" title="Triamcinolone acetonide">Triamcinolone acetonide</a></li></ul> <ul><li>19-Norprogesterone derivatives: <a href="/wiki/17%CE%B1-Methyl-19-norprogesterone" title="17α-Methyl-19-norprogesterone">17α-Methyl-19-norprogesterone</a></li> <li><a href="/wiki/18-Methylsegesterone_acetate" title="18-Methylsegesterone acetate">18-Methylsegesterone acetate</a></li> <li><a href="/wiki/19-Norprogesterone" title="19-Norprogesterone">19-Norprogesterone</a></li> <li><a href="/wiki/Amadinone" title="Amadinone">Amadinone</a></li> <li><a href="/wiki/Amadinone_acetate" title="Amadinone acetate">Amadinone acetate</a></li> <li><a href="/wiki/Demegestone" title="Demegestone">Demegestone</a></li> <li><a href="/w/index.php?title=Fluoro_ethyl_norprogesterone&action=edit&redlink=1" class="new" title="Fluoro ethyl norprogesterone (page does not exist)">Fluoro ethyl norprogesterone</a></li> <li><a href="/w/index.php?title=Fluoro_furanyl_norprogesterone&action=edit&redlink=1" class="new" title="Fluoro furanyl norprogesterone (page does not exist)">Fluoro furanyl norprogesterone</a></li> <li><a href="/wiki/Gestadienol" title="Gestadienol">Gestadienol</a></li> <li><a href="/wiki/Gestadienol_acetate" title="Gestadienol acetate">Gestadienol acetate</a></li> <li><a href="/wiki/Gestonorone_acetate" title="Gestonorone acetate">Gestonorone acetate (gestronol acetate)</a></li> <li><a href="/wiki/Gestonorone_caproate" title="Gestonorone caproate">Gestonorone caproate (gestronol hexanoate)</a></li> <li><a href="/wiki/Gestronol" title="Gestronol">Gestronol (gestonorone)</a></li> <li><a href="/wiki/Nomegestrol" title="Nomegestrol">Nomegestrol</a></li> <li><a href="/wiki/Nomegestrol_acetate" title="Nomegestrol acetate">Nomegestrol acetate</a></li> <li><a href="/wiki/Norgestomet" title="Norgestomet">Norgestomet</a></li> <li><a href="/wiki/ORG-2058" title="ORG-2058">ORG-2058</a></li> <li><a href="/wiki/Oxogestone" title="Oxogestone">Oxogestone</a></li> <li><a href="/wiki/Oxogestone_phenpropionate" title="Oxogestone phenpropionate">Oxogestone phenpropionate (xinogestone)</a></li> <li><a href="/wiki/Promegestone" title="Promegestone">Promegestone</a></li> <li><a href="/wiki/Segesterone" title="Segesterone">Segesterone</a></li> <li><a href="/wiki/Nestorone" class="mw-redirect" title="Nestorone">Segesterone acetate (nestorone)</a></li> <li><a href="/wiki/Trimegestone" title="Trimegestone">Trimegestone</a></li></ul> <ul><li>Testosterone derivatives: Progestins: <a href="/wiki/6,6-Difluoronorethisterone" title="6,6-Difluoronorethisterone">6,6-Difluoronorethisterone</a></li> <li><a href="/wiki/6,6-Difluoronorethisterone_acetate" title="6,6-Difluoronorethisterone acetate">6,6-Difluoronorethisterone acetate</a></li> <li><a href="/wiki/17%CE%B1-Allyl-19-nortestosterone" title="17α-Allyl-19-nortestosterone">17α-Allyl-19-nortestosterone</a></li> <li><a href="/wiki/Allylestrenol" title="Allylestrenol">Allylestrenol</a></li> <li><a href="/wiki/Altrenogest" title="Altrenogest">Altrenogest</a></li> <li><a href="/wiki/Chloroethynylnorgestrel" title="Chloroethynylnorgestrel">Chloroethynylnorgestrel</a></li> <li><a href="/wiki/Cingestol" title="Cingestol">Cingestol</a></li> <li><a href="/wiki/Danazol" title="Danazol">Danazol</a></li> <li><a href="/wiki/Desogestrel" title="Desogestrel">Desogestrel</a></li> <li><a href="/wiki/Dienogest" title="Dienogest">Dienogest</a></li> <li><a href="/wiki/Ethinylandrostenediol" title="Ethinylandrostenediol">Ethinylandrostenediol</a> <ul><li><a href="/wiki/Ethandrostate" title="Ethandrostate">Ethandrostate</a></li></ul></li> <li><a href="/wiki/Ethisterone" title="Ethisterone">Ethisterone</a></li> <li><a href="/wiki/Ethynerone" title="Ethynerone">Ethynerone</a></li> <li><a href="/wiki/Etonogestrel" title="Etonogestrel">Etonogestrel</a></li> <li><a href="/wiki/Etynodiol" title="Etynodiol">Etynodiol</a></li> <li><a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">Etynodiol diacetate</a></li> <li><a href="/wiki/Gestodene" title="Gestodene">Gestodene</a></li> <li><a href="/wiki/Gestrinone" title="Gestrinone">Gestrinone</a></li> <li><a href="/wiki/Levonorgestrel" title="Levonorgestrel">Levonorgestrel</a></li> <li><a href="/wiki/Levonorgestrel_ester" class="mw-redirect" title="Levonorgestrel ester">Levonorgestrel esters</a> (e.g., <a href="/wiki/Levonorgestrel_butanoate" title="Levonorgestrel butanoate">levonorgestrel butanoate</a>)</li> <li><a href="/wiki/Lynestrenol" title="Lynestrenol">Lynestrenol</a></li> <li><a href="/wiki/Lynestrenol_phenylpropionate" title="Lynestrenol phenylpropionate">Lynestrenol phenylpropionate</a></li> <li><a href="/wiki/Metynodiol" title="Metynodiol">Metynodiol</a></li> <li><a href="/wiki/Metynodiol_diacetate" title="Metynodiol diacetate">Metynodiol diacetate</a></li> <li><a href="/wiki/Norelgestromin" title="Norelgestromin">Norelgestromin</a></li> <li><a href="/wiki/Norethisterone" title="Norethisterone">Norethisterone (norethindrone)</a></li> <li><a href="/wiki/Norethisterone_ester" class="mw-redirect" title="Norethisterone ester">Norethisterone esters</a> (e.g., <a href="/wiki/Norethisterone_acetate" title="Norethisterone acetate">norethisterone acetate</a>, <a href="/wiki/Norethisterone_enanthate" title="Norethisterone enanthate">norethisterone enanthate</a>)</li> <li><a href="/wiki/Noretynodrel" title="Noretynodrel">Noretynodrel</a></li> <li><a href="/wiki/Norgesterone" title="Norgesterone">Norgesterone</a></li> <li><a href="/wiki/Norgestimate" title="Norgestimate">Norgestimate</a></li> <li><a href="/wiki/Norgestrel" title="Norgestrel">Norgestrel</a></li> <li><a href="/wiki/Norgestrienone" title="Norgestrienone">Norgestrienone</a></li> <li><a href="/wiki/Norvinisterone" title="Norvinisterone">Norvinisterone</a></li> <li><a href="/wiki/Oxendolone" title="Oxendolone">Oxendolone</a></li> <li><a href="/wiki/Quingestanol" title="Quingestanol">Quingestanol</a></li> <li><a href="/wiki/Quingestanol_acetate" title="Quingestanol acetate">Quingestanol acetate</a></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li> <li><a href="/wiki/Tigestol" title="Tigestol">Tigestol</a></li> <li><a href="/wiki/Tosagestin" title="Tosagestin">Tosagestin</a>; Anabolic–androgenic steroids: <a href="/wiki/11%CE%B2-Methyl-19-nortestosterone" title="11β-Methyl-19-nortestosterone">11β-Methyl-19-nortestosterone</a></li> <li><a href="/wiki/11%CE%B2-Methyl-19-nortestosterone_dodecylcarbonate" title="11β-Methyl-19-nortestosterone dodecylcarbonate">11β-Methyl-19-nortestosterone dodecylcarbonate</a></li> <li><a href="/wiki/19-Nor-5-androstenediol" title="19-Nor-5-androstenediol">19-Nor-5-androstenediol</a></li> <li><a href="/wiki/19-Nor-5-androstenedione" title="19-Nor-5-androstenedione">19-Nor-5-androstenedione</a></li> <li><a href="/wiki/19-Nordehydroepiandrosterone" title="19-Nordehydroepiandrosterone">19-Nordehydroepiandrosterone</a></li> <li><a href="/wiki/Bolandiol" title="Bolandiol">Bolandiol</a></li> <li><a href="/wiki/Bolandiol_dipropionate" title="Bolandiol dipropionate">Bolandiol dipropionate</a></li> <li><a href="/wiki/Bolandione" title="Bolandione">Bolandione</a></li> <li><a href="/wiki/Dimethisterone" title="Dimethisterone">Dimethisterone</a></li> <li><a href="/wiki/Dienedione" title="Dienedione">Dienedione</a></li> <li><a href="/wiki/Dienolone" title="Dienolone">Dienolone</a></li> <li><a href="/wiki/Dimethandrolone" title="Dimethandrolone">Dimethandrolone</a></li> <li><a href="/wiki/Dimethandrolone_buciclate" title="Dimethandrolone buciclate">Dimethandrolone buciclate</a></li> <li><a href="/wiki/Dimethandrolone_dodecylcarbonate" title="Dimethandrolone dodecylcarbonate">Dimethandrolone dodecylcarbonate</a></li> <li><a href="/wiki/Dimethandrolone_undecanoate" title="Dimethandrolone undecanoate">Dimethandrolone undecanoate</a></li> <li><a href="/wiki/Dimethyldienolone" title="Dimethyldienolone">Dimethyldienolone</a></li> <li><a href="/wiki/Dimethyltrienolone" title="Dimethyltrienolone">Dimethyltrienolone</a></li> <li><a href="/wiki/Ethyldienolone" title="Ethyldienolone">Ethyldienolone</a></li> <li><a href="/wiki/Ethylestrenol" title="Ethylestrenol">Ethylestrenol (ethylnandrol)</a></li> <li><a href="/wiki/Methyldienolone" title="Methyldienolone">Methyldienolone</a></li> <li><a href="/wiki/Metribolone" title="Metribolone">Metribolone (R-1881)</a></li> <li><a href="/wiki/Methoxydienone" title="Methoxydienone">Methoxydienone (methoxygonadiene)</a></li> <li><a href="/wiki/Mibolerone" title="Mibolerone">Mibolerone</a></li> <li><a href="/wiki/Nandrolone" title="Nandrolone">Nandrolone</a></li> <li><a href="/wiki/Nandrolone_ester" class="mw-redirect" title="Nandrolone ester">Nandrolone esters</a> (e.g., <a href="/wiki/Nandrolone_decanoate" title="Nandrolone decanoate">nandrolone decanoate</a>, <a href="/wiki/Nandrolone_phenylpropionate" title="Nandrolone phenylpropionate">nandrolone phenylpropionate</a>)</li> <li><a href="/wiki/Norethandrolone" title="Norethandrolone">Norethandrolone</a></li> <li><a href="/wiki/Normethandrone" title="Normethandrone">Normethandrone (methylestrenolone, normethandrolone, normethisterone)</a></li> <li><a href="/wiki/RU-2309" title="RU-2309">RU-2309</a></li> <li><a href="/wiki/Tetrahydrogestrinone" title="Tetrahydrogestrinone">Tetrahydrogestrinone</a></li> <li><a href="/wiki/Trenbolone" title="Trenbolone">Trenbolone (trienolone)</a></li> <li><a href="/wiki/Trenbolone_ester" class="mw-redirect" title="Trenbolone ester">Trenbolone esters</a> (e.g., <a href="/wiki/Trenbolone_acetate" title="Trenbolone acetate">trenbolone acetate</a>, <a href="/wiki/Trenbolone_enanthate" title="Trenbolone enanthate">trenbolone enanthate</a>)</li> <li><a href="/wiki/Trendione" title="Trendione">Trendione</a></li> <li><a href="/wiki/Trestolone" title="Trestolone">Trestolone</a></li> <li><a href="/wiki/Trestolone_acetate" title="Trestolone acetate">Trestolone acetate</a></li></ul> <ul><li>Spirolactone derivatives: <a href="/wiki/Canrenoic_acid" title="Canrenoic acid">Canrenoic acid</a></li> <li><a href="/wiki/Canrenone" title="Canrenone">Canrenone</a></li> <li><a href="/wiki/Drospirenone" title="Drospirenone">Drospirenone</a></li> <li><a href="/wiki/Mespirenone" title="Mespirenone">Mespirenone</a></li> <li><a href="/wiki/Potassium_canrenoate" title="Potassium canrenoate">Potassium canrenoate</a></li> <li><a href="/wiki/Prorenone" title="Prorenone">Prorenone</a></li> <li><a href="/wiki/SC-5233" title="SC-5233">SC-5233 (spirolactone)</a></li> <li><a href="/wiki/SC-8109" title="SC-8109">SC-8109</a></li> <li><a class="mw-selflink selflink">Spironolactone</a></li> <li><a href="/wiki/Spirorenone" title="Spirorenone">Spirorenone</a></li></ul> <ul><li>Nonsteroidal: <a href="/wiki/3,8-Dihydrodiligustilide" title="3,8-Dihydrodiligustilide">3,8-Dihydrodiligustilide</a></li> <li><a href="/wiki/LG-2527" title="LG-2527">LG-2527</a></li> <li><a href="/w/index.php?title=LG-100128&action=edit&redlink=1" class="new" title="LG-100128 (page does not exist)">LG-100128</a></li> <li><a href="/wiki/Riligustilide" title="Riligustilide">Riligustilide</a></li> <li><a href="/w/index.php?title=RWJ-26819&action=edit&redlink=1" class="new" title="RWJ-26819 (page does not exist)">RWJ-26819</a></li> <li><a href="/w/index.php?title=RWJ-49853&action=edit&redlink=1" class="new" title="RWJ-49853 (page does not exist)">RWJ-49853</a></li> <li><a href="/w/index.php?title=RWJ-60130&action=edit&redlink=1" class="new" title="RWJ-60130 (page does not exist)">RWJ-60130</a></li> <li><a href="/wiki/Tanaproget" title="Tanaproget">Tanaproget</a></li> <li><a href="/wiki/ZM-182345" title="ZM-182345">ZM-182345</a></li></ul> <ul><li>Unknown: <a href="/wiki/ORG-47241" title="ORG-47241">ORG-47241</a></li> <li><a href="/wiki/ORG-201745" title="ORG-201745">ORG-201745</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Mixed (<a href="/wiki/Selective_progesterone_receptor_modulators" class="mw-redirect" title="Selective progesterone receptor modulators"><abbr title="Selective progesterone receptor modulators">SPRMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Selective progesterone receptor modulators)</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Steroidal: <a href="/wiki/Dihydroethisterone" class="mw-redirect" title="Dihydroethisterone">Dihydroethisterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydrolevonorgestrel" title="5α-Dihydrolevonorgestrel">5α-Dihydrolevonorgestrel</a></li> <li><a href="/wiki/5%CE%B1-Dihydronorethisterone" title="5α-Dihydronorethisterone">5α-Dihydronorethisterone</a></li> <li><a href="/wiki/Asoprisnil" title="Asoprisnil">Asoprisnil</a></li> <li><a href="/wiki/Asoprisnil_ecamate" title="Asoprisnil ecamate">Asoprisnil ecamate</a></li> <li><a href="/wiki/Guggulsterone" title="Guggulsterone">Guggulsterone</a></li> <li><a href="/w/index.php?title=J1042&action=edit&redlink=1" class="new" title="J1042 (page does not exist)">J1042</a></li> <li><a href="/w/index.php?title=LG-120838&action=edit&redlink=1" class="new" title="LG-120838 (page does not exist)">LG-120838</a></li> <li><a href="/wiki/Metapristone" title="Metapristone">Metapristone (RU-42633)</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone (RU-486)</a></li> <li><a href="/w/index.php?title=ORF-9371&action=edit&redlink=1" class="new" title="ORF-9371 (page does not exist)">ORF-9371</a></li> <li><a href="/wiki/ORF-9326" class="mw-redirect" title="ORF-9326">ORF-9326</a></li> <li><a href="/w/index.php?title=ORG-31710&action=edit&redlink=1" class="new" title="ORG-31710 (page does not exist)">ORG-31710</a></li> <li><a href="/w/index.php?title=ORG-33628&action=edit&redlink=1" class="new" title="ORG-33628 (page does not exist)">ORG-33628</a></li> <li><a href="/w/index.php?title=RMI-12936&action=edit&redlink=1" class="new" title="RMI-12936 (page does not exist)">RMI-12936</a></li> <li><a href="/wiki/Telapristone" title="Telapristone">Telapristone</a></li> <li><a href="/wiki/Ulipristal_acetate" title="Ulipristal acetate">Ulipristal acetate</a></li> <li><a href="/wiki/Vilaprisan" title="Vilaprisan">Vilaprisan</a></li> <li><a href="/w/index.php?title=ZK-137316&action=edit&redlink=1" class="new" title="ZK-137316 (page does not exist)">ZK-137316</a></li></ul> <ul><li>Nonsteroidal: <a href="/wiki/Apigenin" title="Apigenin">Apigenin</a></li> <li><a href="/wiki/Kaempferol" title="Kaempferol">Kaempferol</a></li> <li><a href="/w/index.php?title=LG-120920&action=edit&redlink=1" class="new" title="LG-120920 (page does not exist)">LG-120920</a></li> <li><a href="/wiki/Naringenin" title="Naringenin">Naringenin</a></li> <li><a href="/w/index.php?title=PRA-910&action=edit&redlink=1" class="new" title="PRA-910 (page does not exist)">PRA-910</a></li> <li><a href="/wiki/Syringic_acid" title="Syringic acid">Syringic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Steroidal: <a href="/wiki/Aglepristone" title="Aglepristone">Aglepristone</a></li> <li><a href="/wiki/Lilopristone" title="Lilopristone">Lilopristone</a></li> <li><a href="/wiki/Lonaprisan" title="Lonaprisan">Lonaprisan</a></li> <li><a href="/wiki/Onapristone" title="Onapristone">Onapristone</a></li> <li><a href="/w/index.php?title=ORG-31710&action=edit&redlink=1" class="new" title="ORG-31710 (page does not exist)">ORG-31710</a></li> <li><a href="/w/index.php?title=ORG-31806&action=edit&redlink=1" class="new" title="ORG-31806 (page does not exist)">ORG-31806</a></li> <li><a href="/w/index.php?title=ORG-33628&action=edit&redlink=1" class="new" title="ORG-33628 (page does not exist)">ORG-33628</a></li> <li><a href="/w/index.php?title=RTI_3021%E2%80%93022&action=edit&redlink=1" class="new" title="RTI 3021–022 (page does not exist)">RTI 3021–022</a></li> <li><a href="/wiki/Toripristone" title="Toripristone">Toripristone</a></li> <li><a href="/wiki/Zanoterone" title="Zanoterone">Zanoterone</a></li></ul> <ul><li>Nonsteroidal: <a href="/wiki/Darolutamide" title="Darolutamide">Darolutamide</a></li> <li><a href="/w/index.php?title=LG-001447&action=edit&redlink=1" class="new" title="LG-001447 (page does not exist)">LG-001447</a></li> <li><a href="/w/index.php?title=LG-100127&action=edit&redlink=1" class="new" title="LG-100127 (page does not exist)">LG-100127</a></li> <li><a href="/w/index.php?title=LG-100128&action=edit&redlink=1" class="new" title="LG-100128 (page does not exist)">LG-100128</a></li> <li><a href="/w/index.php?title=LG-120830&action=edit&redlink=1" class="new" title="LG-120830 (page does not exist)">LG-120830</a></li> <li><a href="/w/index.php?title=LG-121046&action=edit&redlink=1" class="new" title="LG-121046 (page does not exist)">LG-121046</a></li> <li><a href="/wiki/Valproic_acid" class="mw-redirect" title="Valproic acid">Valproic acid</a></li> <li><a href="/w/index.php?title=ZM-150271&action=edit&redlink=1" class="new" title="ZM-150271 (page does not exist)">ZM-150271</a></li> <li><a href="/w/index.php?title=ZM-172406&action=edit&redlink=1" class="new" title="ZM-172406 (page does not exist)">ZM-172406</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Membrane_progesterone_receptor" title="Membrane progesterone receptor"><abbr title="Membrane progesterone receptor">mPR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Membrane progesterone receptor (<a href="/wiki/Progestin_and_adipoQ_receptor" title="Progestin and adipoQ receptor"><abbr title="Progestin and adipoQ receptor">PAQR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Progestin and adipoQ receptor)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">5α-Dihydroprogesterone</a></li> <li><a href="/wiki/5%CE%B2-Dihydroprogesterone" title="5β-Dihydroprogesterone">5β-Dihydroprogesterone</a></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycortisone (21-hydroxyprogesterone)</a></li> <li><a href="/wiki/11-Deoxycortisol" title="11-Deoxycortisol">11-Deoxycortisol (17α,21-dihydroxyprogesterone)</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone</a></li> <li><a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a></li> <li><a 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="Xenobiotic-sensing_receptor_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Xenobiotic-sensing_receptor_modulators" title="Template:Xenobiotic-sensing receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Xenobiotic-sensing_receptor_modulators" title="Template talk:Xenobiotic-sensing receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Xenobiotic-sensing_receptor_modulators" title="Special:EditPage/Template:Xenobiotic-sensing receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Xenobiotic-sensing_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Xenobiotic-sensing_receptor" title="Xenobiotic-sensing receptor">Xenobiotic-sensing receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Constitutive_androstane_receptor" title="Constitutive androstane receptor"><abbr title="Constitutive androstane receptor">CAR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Constitutive androstane receptor</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/w/index.php?title=6,7-Dimethylesculetin&action=edit&redlink=1" class="new" title="6,7-Dimethylesculetin (page does not exist)">6,7-Dimethylesculetin</a></li> <li><a href="/wiki/Amiodarone" title="Amiodarone">Amiodarone</a></li> <li><a href="/wiki/Artemisinin" title="Artemisinin">Artemisinin</a></li> <li><a href="/w/index.php?title=Benfuracarb&action=edit&redlink=1" class="new" title="Benfuracarb (page does not exist)">Benfuracarb</a></li> <li><a href="/wiki/Carbamazepine" title="Carbamazepine">Carbamazepine</a></li> <li><a href="/wiki/Carvedilol" title="Carvedilol">Carvedilol</a></li> <li><a href="/wiki/Chlorpromazine" title="Chlorpromazine">Chlorpromazine</a></li> <li><a href="/wiki/Chrysin" title="Chrysin">Chrysin</a></li> <li><a href="/w/index.php?title=CITCO_(drug)&action=edit&redlink=1" class="new" title="CITCO (drug) (page does not exist)">CITCO</a></li> <li><a href="/wiki/Clotrimazole" title="Clotrimazole">Clotrimazole</a></li> <li><a href="/wiki/Cyclophosphamide" title="Cyclophosphamide">Cyclophosphamide</a></li> <li><a href="/wiki/Cypermethrin" title="Cypermethrin">Cypermethrin</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a> (<a href="/wiki/Prasterone" title="Prasterone">prasterone</a>)</li> <li><a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Ellagic_acid" title="Ellagic acid">Ellagic acid</a></li> <li><a href="/wiki/Griseofulvin" title="Griseofulvin">Griseofulvin</a></li> <li><a href="/wiki/Methoxychlor" title="Methoxychlor">Methoxychlor</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li> <li><a href="/wiki/Nefazodone" title="Nefazodone">Nefazodone</a></li> <li><a href="/wiki/Nevirapine" title="Nevirapine">Nevirapine</a></li> <li><a href="/wiki/Nicardipine" title="Nicardipine">Nicardipine</a></li> <li><a href="/w/index.php?title=Octicizer&action=edit&redlink=1" class="new" title="Octicizer (page does not exist)">Octicizer</a></li> <li><a href="/wiki/Permethrin" title="Permethrin">Permethrin</a></li> <li><a href="/wiki/Phenobarbital" title="Phenobarbital">Phenobarbital</a></li> <li><a href="/wiki/Phenytoin" title="Phenytoin">Phenytoin</a></li> <li><a href="/wiki/5%CE%B2-Dihydroprogesterone" title="5β-Dihydroprogesterone">Pregnanedione (5β-dihydroprogesterone)</a></li> <li><a href="/wiki/Reserpine" title="Reserpine">Reserpine</a></li> <li><a href="/w/index.php?title=TCPOBOP&action=edit&redlink=1" class="new" title="TCPOBOP (page does not exist)">TCPOBOP</a></li> <li><a href="/wiki/Telmisartan" title="Telmisartan">Telmisartan</a></li> <li><a href="/wiki/Tolnaftate" title="Tolnaftate">Tolnaftate</a></li> <li><a href="/wiki/Troglitazone" title="Troglitazone">Troglitazone</a></li> <li><a href="/wiki/Valproic_acid" class="mw-redirect" title="Valproic acid">Valproic acid</a></li></ul> <ul><li>Antagonists: <a href="/w/index.php?title=3,17%CE%B2-Estradiol&action=edit&redlink=1" class="new" title="3,17β-Estradiol (page does not exist)">3,17β-Estradiol</a></li> <li><a href="/w/index.php?title=5%CE%B1-Androstan-3%CE%B1-ol&action=edit&redlink=1" class="new" title="5α-Androstan-3α-ol (page does not exist)">3α-Androstanol</a></li> <li><a href="/wiki/5%CE%B1-Androst-16-en-3%CE%B1-ol" class="mw-redirect" title="5α-Androst-16-en-3α-ol">3α-Androstenol</a></li> <li><a href="/w/index.php?title=5%CE%B1-Androstan-3%CE%B2-ol&action=edit&redlink=1" class="new" title="5α-Androstan-3β-ol (page does not exist)">3β-Androstanol</a></li> <li><a href="/w/index.php?title=5%CE%B1-Androstan-17-ol&action=edit&redlink=1" class="new" title="5α-Androstan-17-ol (page does not exist)">17-Androstanol</a></li> <li><a href="/wiki/Allyl_isothiocyanate" title="Allyl isothiocyanate">AITC</a></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a></li> <li><a href="/wiki/Meclizine" title="Meclizine">Meclizine</a></li> <li><a href="/w/index.php?title=Nigramide_J&action=edit&redlink=1" class="new" title="Nigramide J (page does not exist)">Nigramide J</a></li> <li><a href="/wiki/Okadaic_acid" title="Okadaic acid">Okadaic acid</a></li> <li><a href="/wiki/PK-11195" class="mw-redirect" title="PK-11195">PK-11195</a></li> <li><a href="/w/index.php?title=S-07662&action=edit&redlink=1" class="new" title="S-07662 (page does not exist)">S-07662</a></li> <li><a href="/w/index.php?title=T-0901317&action=edit&redlink=1" class="new" title="T-0901317 (page does not exist)">T-0901317</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Pregnane_X_receptor" title="Pregnane X receptor"><abbr title="Pregnane X receptor">PXR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Pregnane X receptor</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/17%CE%B1-Hydroxypregnenolone" title="17α-Hydroxypregnenolone">17α-Hydroxypregnenolone</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone</a></li> <li><a href="/wiki/%CE%944-Androstenedione" class="mw-redirect" title="Δ4-Androstenedione">Δ4-Androstenedione</a></li> <li><a href="/wiki/%CE%945-Androstenediol" class="mw-redirect" title="Δ5-Androstenediol">Δ5-Androstenediol</a></li> <li><a href="/wiki/%CE%945-Androstenedione" class="mw-redirect" title="Δ5-Androstenedione">Δ5-Androstenedione</a></li> <li><a href="/w/index.php?title=AA-861&action=edit&redlink=1" class="new" title="AA-861 (page does not exist)">AA-861</a></li> <li><a href="/wiki/Allopregnanediol" title="Allopregnanediol">Allopregnanediol</a></li> <li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">Allopregnanedione (5α-dihydroprogesterone)</a></li> <li><a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone (brexanolone)</a></li> <li><a href="/wiki/Alpha-Lipoic_acid" class="mw-redirect" title="Alpha-Lipoic acid">Alpha-Lipoic acid</a></li> <li><a href="/wiki/Ambrisentan" title="Ambrisentan">Ambrisentan</a></li> <li><a href="/wiki/AMI-193" class="mw-redirect" title="AMI-193">AMI-193</a></li> <li><a href="/wiki/Amlodipine_besylate" class="mw-redirect" title="Amlodipine besylate">Amlodipine besylate</a></li> <li><a href="/wiki/Antimycotic" class="mw-redirect" title="Antimycotic">Antimycotics</a></li> <li><a href="/wiki/Artemisinin" title="Artemisinin">Artemisinin</a></li> <li><a href="/wiki/Aurothioglucose" title="Aurothioglucose">Aurothioglucose</a></li> <li><a href="/wiki/Bile_acid" title="Bile acid">Bile acids</a></li> <li><a href="/wiki/Bithionol" title="Bithionol">Bithionol</a></li> <li><a href="/wiki/Bosentan" title="Bosentan">Bosentan</a></li> <li><a href="/w/index.php?title=Bumecaine&action=edit&redlink=1" class="new" title="Bumecaine (page does not exist)">Bumecaine</a></li> <li><a href="/wiki/Cafestol" title="Cafestol">Cafestol</a></li> <li><a href="/wiki/Cephaloridine" title="Cephaloridine">Cephaloridine</a></li> <li><a href="/wiki/Cephradine" class="mw-redirect" title="Cephradine">Cephradine</a></li> <li><a href="/wiki/Chlorpromazine" title="Chlorpromazine">Chlorpromazine</a></li> <li><a href="/wiki/Ciglitazone" title="Ciglitazone">Ciglitazone</a></li> <li><a href="/wiki/Clindamycin" title="Clindamycin">Clindamycin</a></li> <li><a href="/wiki/Clofenvinfos" class="mw-redirect" title="Clofenvinfos">Clofenvinfos</a></li> <li><a href="/wiki/Chloroxine" title="Chloroxine">Chloroxine</a></li> <li><a href="/wiki/Clotrimazole" title="Clotrimazole">Clotrimazole</a></li> <li><a href="/wiki/Colforsin" class="mw-redirect" title="Colforsin">Colforsin</a></li> <li><a href="/wiki/Corticosterone" title="Corticosterone">Corticosterone</a></li> <li><a href="/wiki/Cyclophosphamide" title="Cyclophosphamide">Cyclophosphamide</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Demecolcine" title="Demecolcine">Demecolcine</a></li> <li><a href="/wiki/Dexamethasone" title="Dexamethasone">Dexamethasone</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a> (<a href="/wiki/Prasterone" title="Prasterone">prasterone</a>)</li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA-S</a> (<a href="/wiki/Prasterone_sulfate" title="Prasterone sulfate">prasterone sulfate</a>)</li> <li><a href="/wiki/Dibunate_sodium" class="mw-redirect" title="Dibunate sodium">Dibunate sodium</a></li> <li><a href="/wiki/Diclazuril" title="Diclazuril">Diclazuril</a></li> <li><a href="/wiki/Dicloxacillin" title="Dicloxacillin">Dicloxacillin</a></li> <li><a href="/wiki/Dimercaprol" title="Dimercaprol">Dimercaprol</a></li> <li><a href="/w/index.php?title=Dinaline&action=edit&redlink=1" class="new" title="Dinaline (page does not exist)">Dinaline</a></li> <li><a href="/wiki/Docetaxel" title="Docetaxel">Docetaxel</a></li> <li><a href="/wiki/Docusate_calcium" class="mw-redirect" title="Docusate calcium">Docusate calcium</a></li> <li><a href="/wiki/Dodecylbenzenesulfonic_acid" class="mw-redirect" title="Dodecylbenzenesulfonic acid">Dodecylbenzenesulfonic acid</a></li> <li><a href="/wiki/Dronabinol" title="Dronabinol">Dronabinol</a></li> <li><a href="/wiki/Droxidopa" title="Droxidopa">Droxidopa</a></li> <li><a href="/wiki/Eburnamonine" class="mw-redirect" title="Eburnamonine">Eburnamonine</a></li> <li><a href="/wiki/Ecopipam" title="Ecopipam">Ecopipam</a></li> <li><a href="/wiki/Enzacamene" title="Enzacamene">Enzacamene</a></li> <li><a href="/wiki/Epothilone_B" class="mw-redirect" title="Epothilone B">Epothilone B</a></li> <li><a href="/wiki/Erythromycin" title="Erythromycin">Erythromycin</a></li> <li><a href="/wiki/Famprofazone" title="Famprofazone">Famprofazone</a></li> <li><a href="/w/index.php?title=Febantel&action=edit&redlink=1" class="new" title="Febantel (page does not exist)">Febantel</a></li> <li><a href="/wiki/Felodipine" title="Felodipine">Felodipine</a></li> <li><a href="/wiki/Fenbendazole" title="Fenbendazole">Fenbendazole</a></li> <li><a href="/wiki/Fentanyl" title="Fentanyl">Fentanyl</a></li> <li><a href="/wiki/Flucloxacillin" title="Flucloxacillin">Flucloxacillin</a></li> <li><a href="/wiki/Fluorometholone" title="Fluorometholone">Fluorometholone</a></li> <li><a href="/wiki/Griseofulvin" title="Griseofulvin">Griseofulvin</a></li> <li><a href="/wiki/Guggulsterone" title="Guggulsterone">Guggulsterone</a></li> <li><a href="/wiki/Haloprogin" title="Haloprogin">Haloprogin</a></li> <li><a href="/wiki/Hetacillin_potassium" class="mw-redirect" title="Hetacillin potassium">Hetacillin potassium</a></li> <li><a href="/wiki/Hyperforin" title="Hyperforin">Hyperforin</a></li> <li><a href="/wiki/Hypericum_perforatum" title="Hypericum perforatum">Hypericum perforatum (St John's wort)</a></li> <li><a href="/wiki/Indinavir_sulfate" class="mw-redirect" title="Indinavir sulfate">Indinavir sulfate</a></li> <li><a href="/wiki/Lasalocid_sodium" class="mw-redirect" title="Lasalocid sodium">Lasalocid sodium</a></li> <li><a href="/wiki/Levothyroxine" title="Levothyroxine">Levothyroxine</a></li> <li>Linolenic acid: <a href="/wiki/%CE%91-Linolenic_acid" title="Α-Linolenic acid">α-Linolenic acid</a> and <a href="/wiki/Gamma-Linolenic_acid" class="mw-redirect" title="Gamma-Linolenic acid">γ-linolenic acid</a></li> <li><a href="/w/index.php?title=LOE-908&action=edit&redlink=1" class="new" title="LOE-908 (page does not exist)">LOE-908</a></li> <li><a href="/wiki/Loratadine" title="Loratadine">Loratadine</a></li> <li><a href="/wiki/Lovastatin" title="Lovastatin">Lovastatin</a></li> <li><a href="/wiki/Meclizine" title="Meclizine">Meclizine</a></li> <li><a href="/wiki/Metacycline" title="Metacycline">Metacycline</a></li> <li><a href="/wiki/Methylprednisolone" title="Methylprednisolone">Methylprednisolone</a></li> <li><a href="/wiki/Metyrapone" title="Metyrapone">Metyrapone</a></li> <li><a href="/wiki/Mevastatin" title="Mevastatin">Mevastatin</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li> <li><a href="/wiki/Nafcillin" title="Nafcillin">Nafcillin</a></li> <li><a href="/wiki/Nicardipine" title="Nicardipine">Nicardipine</a></li> <li><a href="/wiki/Nicotine" title="Nicotine">Nicotine</a></li> <li><a href="/wiki/Nifedipine" title="Nifedipine">Nifedipine</a></li> <li><a href="/wiki/Nilvadipine" title="Nilvadipine">Nilvadipine</a></li> <li><a href="/wiki/Nisoldipine" title="Nisoldipine">Nisoldipine</a></li> <li><a href="/wiki/Norelgestromin" title="Norelgestromin">Norelgestromin</a></li> <li><a href="/wiki/Omeprazole" title="Omeprazole">Omeprazole</a></li> <li><a href="/wiki/Orlistat" title="Orlistat">Orlistat</a></li> <li><a href="/wiki/Oxatomide" title="Oxatomide">Oxatomide</a></li> <li><a href="/wiki/Paclitaxel" title="Paclitaxel">Paclitaxel</a></li> <li><a href="/wiki/Phenobarbital" title="Phenobarbital">Phenobarbital</a></li> <li><a href="/wiki/Piperine" title="Piperine">Piperine</a></li> <li><a href="/wiki/Plicamycin" title="Plicamycin">Plicamycin</a></li> <li><a href="/wiki/Prednisolone" title="Prednisolone">Prednisolone</a></li> <li><a href="/wiki/Pregnanediol" title="Pregnanediol">Pregnanediol</a></li> <li><a href="/wiki/5%CE%B2-Dihydroprogesterone" title="5β-Dihydroprogesterone">Pregnanedione (5β-dihydroprogesterone)</a></li> <li><a href="/wiki/Pregnanolone" title="Pregnanolone">Pregnanolone</a></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a></li> <li><a href="/wiki/Pregnenolone_16%CE%B1-carbonitrile" title="Pregnenolone 16α-carbonitrile">Pregnenolone 16α-carbonitrile</a></li> <li><a href="/wiki/Proadifen" title="Proadifen">Proadifen</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Quingestrone" title="Quingestrone">Quingestrone</a></li> <li><a href="/wiki/Reserpine" title="Reserpine">Reserpine</a></li> <li><a href="/wiki/Reverse_triiodothyronine" title="Reverse triiodothyronine">Reverse triiodothyronine</a></li> <li><a href="/wiki/Rifampicin" title="Rifampicin">Rifampicin</a></li> <li><a href="/wiki/Rifaximin" title="Rifaximin">Rifaximin</a></li> <li><a href="/wiki/Rimexolone" title="Rimexolone">Rimexolone</a></li> <li><a href="/wiki/Riodipine" title="Riodipine">Riodipine</a></li> <li><a href="/wiki/Ritonavir" title="Ritonavir">Ritonavir</a></li> <li><a href="/wiki/Simvastatin" title="Simvastatin">Simvastatin</a></li> <li><a href="/wiki/Sirolimus" title="Sirolimus">Sirolimus</a></li> <li><a class="mw-selflink selflink">Spironolactone</a></li> <li><a href="/wiki/Spiroxatrine" title="Spiroxatrine">Spiroxatrine</a></li> <li><a href="/w/index.php?title=SR-12813&action=edit&redlink=1" class="new" title="SR-12813 (page does not exist)">SR-12813</a></li> <li><a href="/w/index.php?title=Suberoylanilide&action=edit&redlink=1" class="new" title="Suberoylanilide (page does not exist)">Suberoylanilide</a></li> <li><a href="/wiki/Sulfisoxazole" class="mw-redirect" title="Sulfisoxazole">Sulfisoxazole</a></li> <li><a href="/wiki/Suramin" title="Suramin">Suramin</a></li> <li><a href="/wiki/Tacrolimus" title="Tacrolimus">Tacrolimus</a></li> <li><a href="/w/index.php?title=Tenylidone&action=edit&redlink=1" class="new" title="Tenylidone (page does not exist)">Tenylidone</a></li> <li><a href="/wiki/Terconazole" title="Terconazole">Terconazole</a></li> <li><a href="/wiki/Testosterone_isocaproate" title="Testosterone isocaproate">Testosterone isocaproate</a></li> <li><a href="/wiki/Tetracycline" title="Tetracycline">Tetracycline</a></li> <li><a href="/wiki/Thiamylal_sodium" class="mw-redirect" title="Thiamylal sodium">Thiamylal sodium</a></li> <li><a href="/wiki/Thiothixene" class="mw-redirect" title="Thiothixene">Thiothixene</a></li> <li><a href="/wiki/Thonzonium_bromide" title="Thonzonium bromide">Thonzonium bromide</a></li> <li><a href="/wiki/Tianeptine" title="Tianeptine">Tianeptine</a></li> <li><a href="/wiki/Troglitazone" title="Troglitazone">Troglitazone</a></li> <li><a href="/wiki/Troleandomycin" title="Troleandomycin">Troleandomycin</a></li> <li><a href="/w/index.php?title=Tropanyl_3,5-dimethulbenzoate&action=edit&redlink=1" class="new" title="Tropanyl 3,5-dimethulbenzoate (page does not exist)">Tropanyl 3,5-dimethulbenzoate</a></li> <li><a href="/wiki/Zafirlukast" title="Zafirlukast">Zafirlukast</a></li> <li><a href="/wiki/Zeranol" title="Zeranol">Zeranol</a></li></ul> <ul><li>Antagonists: <a href="/wiki/Ketoconazole" title="Ketoconazole">Ketoconazole</a></li> <li><a href="/wiki/Sesamin" title="Sesamin">Sesamin</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd></dl> </div></td></tr></tbody></table></div></div></td></tr></tbody></table></div> <style 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