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class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Progestogenic_activity"> <div class="vector-toc-text"> 6.1.1 Progestogenic activity </div> </a> <ul id="toc-Progestogenic_activity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Androgenic_activity" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Androgenic_activity"> <div class="vector-toc-text"> 6.1.2 Androgenic activity </div> </a> <ul id="toc-Androgenic_activity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Estrogenic_activity" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Estrogenic_activity"> <div class="vector-toc-text"> 6.1.3 Estrogenic activity </div> </a> <ul id="toc-Estrogenic_activity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Neurosteroid_activity" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Neurosteroid_activity"> <div class="vector-toc-text"> 6.1.4 Neurosteroid activity </div> </a> <ul id="toc-Neurosteroid_activity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Steroidogenesis_inhibition" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Steroidogenesis_inhibition"> <div class="vector-toc-text"> 6.1.5 Steroidogenesis inhibition </div> </a> <ul id="toc-Steroidogenesis_inhibition-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_activities" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Other_activities"> <div class="vector-toc-text"> 6.1.6 Other activities </div> </a> <ul id="toc-Other_activities-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Antigonadotropic_effects" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Antigonadotropic_effects"> <div class="vector-toc-text"> 6.1.7 Antigonadotropic effects </div> </a> <ul id="toc-Antigonadotropic_effects-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Pharmacokinetics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmacokinetics"> <div class="vector-toc-text"> 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-Derivatives" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Derivatives"> <div class="vector-toc-text"> 7.1 Derivatives </div> </a> <ul id="toc-Derivatives-sublist" class="vector-toc-list"> <li id="toc-Non-17α-ethynylated" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Non-17α-ethynylated"> <div class="vector-toc-text"> 7.1.1 Non-17α-ethynylated </div> </a> <ul id="toc-Non-17α-ethynylated-sublist" class="vector-toc-list"> </ul> </li> </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"> 7.2 Synthesis </div> </a> <ul id="toc-Synthesis-sublist" class="vector-toc-list"> <li id="toc-Synthesis_1" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Synthesis_1"> <div class="vector-toc-text"> 7.2.1 Synthesis 1 </div> </a> <ul id="toc-Synthesis_1-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Synthesis_2" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Synthesis_2"> <div class="vector-toc-text"> 7.2.2 Synthesis 2 </div> </a> <ul id="toc-Synthesis_2-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> 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"> <li id="toc-United_States" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#United_States"> <div class="vector-toc-text"> 9.3.1 United States </div> </a> <ul id="toc-United_States-sublist" class="vector-toc-list"> </ul> </li> </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> <ul id="toc-Research-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> 11 References </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Further_reading" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Further_reading"> <div class="vector-toc-text"> 12 Further reading </div> </a> <ul id="toc-Further_reading-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" 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Available in 23 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-23" aria-hidden="true" > 23 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/%D9%86%D9%88%D8%B1%D9%8A%D8%AB%D9%8A%D8%B3%D8%AA%D9%8A%D8%B1%D9%88%D9%86" title="نوريثيستيرون – Arabic" lang="ar" hreflang="ar" data-title="نوريثيستيرون" 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/%D9%86%D9%88%D8%B1%D8%A7%D8%AA%DB%8C_%D8%B3%D8%AA%D8%B1%D9%88%D9%86" title="نوراتی سترون – South Azerbaijani" lang="azb" hreflang="azb" data-title="نوراتی سترون" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target">تۆرکجه</a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Norethisteron" title="Norethisteron – Welsh" lang="cy" hreflang="cy" data-title="Norethisteron" 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/Norethisteron" title="Norethisteron – German" lang="de" hreflang="de" data-title="Norethisteron" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target">Deutsch</a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/19-noretisterona" title="19-noretisterona – Spanish" lang="es" hreflang="es" data-title="19-noretisterona" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target">Español</a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%86%D9%88%D8%B1%D8%A7%D8%AA%DB%8C_%D8%B3%D8%AA%D8%B1%D9%88%D9%86" title="نوراتی سترون – Persian" lang="fa" hreflang="fa" data-title="نوراتی سترون" 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/Nor%C3%A9thist%C3%A9rone" title="Noréthistérone – French" lang="fr" hreflang="fr" data-title="Noréthistérone" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target">Français</a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Noretisteron" title="Noretisteron – Indonesian" lang="id" hreflang="id" data-title="Noretisteron" 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/Noretisterone" title="Noretisterone – Italian" lang="it" hreflang="it" data-title="Noretisterone" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target">Italiano</a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%9D%D0%BE%D1%80%D0%B5%D1%82%D0%B8%D1%81%D1%82%D0%B5%D1%80%D0%BE%D0%BD" title="Норетистерон – Macedonian" lang="mk" hreflang="mk" data-title="Норетистерон" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target">Македонски</a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%A8%E0%B5%8B%E0%B4%B1%E0%B5%86%E0%B4%A4%E0%B4%BF%E0%B4%B8%E0%B5%8D%E0%B4%B1%E0%B5%8D%E0%B4%B1%E0%B5%86%E0%B4%B1%E0%B5%8B%E0%B5%BA" title="നോറെതിസ്റ്റെറോൺ – Malayalam" lang="ml" hreflang="ml" data-title="നോറെതിസ്റ്റെറോൺ" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target">മലയാളം</a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Noretisteron" title="Noretisteron – Malay" lang="ms" hreflang="ms" data-title="Noretisteron" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target">Bahasa Melayu</a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%8E%E3%83%AB%E3%82%A8%E3%83%81%E3%82%B9%E3%83%86%E3%83%AD%E3%83%B3" title="ノルエチステロン – Japanese" lang="ja" hreflang="ja" data-title="ノルエチステロン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target">日本語</a></li><li class="interlanguage-link interwiki-or mw-list-item"><a href="https://or.wikipedia.org/wiki/%E0%AC%A8%E0%AC%B0%E0%AC%8F%E0%AC%A5%E0%AC%BF%E0%AC%B7%E0%AD%8D%E0%AC%9F%E0%AD%87%E0%AC%B0%E0%AC%A8" title="ନରଏଥିଷ୍ଟେରନ – Odia" lang="or" hreflang="or" data-title="ନରଏଥିଷ୍ଟେରନ" data-language-autonym="ଓଡ଼ିଆ" data-language-local-name="Odia" class="interlanguage-link-target">ଓଡ଼ିଆ</a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Noretysteron" title="Noretysteron – Polish" lang="pl" hreflang="pl" data-title="Noretysteron" 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/Noretisterona" title="Noretisterona – Portuguese" lang="pt" hreflang="pt" data-title="Noretisterona" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target">Português</a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9D%D0%BE%D1%80%D1%8D%D1%82%D0%B8%D1%81%D1%82%D0%B5%D1%80%D0%BE%D0%BD" title="Норэтистерон – Russian" lang="ru" hreflang="ru" data-title="Норэтистерон" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target">Русский</a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Noretindron" title="Noretindron – Slovenian" lang="sl" hreflang="sl" data-title="Noretindron" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target">Slovenščina</a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Noretisteron" title="Noretisteron – Serbian" lang="sr" hreflang="sr" data-title="Noretisteron" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target">Српски / srpski</a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Noretisteron" title="Noretisteron – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Noretisteron" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target">Srpskohrvatski / српскохрватски</a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Noretisteroni" title="Noretisteroni – Finnish" lang="fi" hreflang="fi" data-title="Noretisteroni" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target">Suomi</a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Noretisteron" title="Noretisteron – Turkish" lang="tr" hreflang="tr" data-title="Noretisteron" data-language-autonym="Türkçe" 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searchaux" style="display:none">Progestin medication</div> <div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Pharmaceutical compound</div> <style data-mw-deduplicate="TemplateStyles:r1269284339">@media screen{html.skin-theme-clientpref-night .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}</style> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title">Norethisterone</caption><tbody><tr><td colspan="2" class="infobox-image"><a href="/wiki/File:Norethisterone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d4/Norethisterone.svg/250px-Norethisterone.svg.png" decoding="async" width="225" height="164" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d4/Norethisterone.svg/500px-Norethisterone.svg.png 1.5x" data-file-width="512" data-file-height="373" /></a></td></tr><tr><td colspan="2" class="infobox-image"><a href="/wiki/File:Norethisterone_molecule_ball.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Norethisterone_molecule_ball.png/250px-Norethisterone_molecule_ball.png" decoding="async" width="235" height="191" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Norethisterone_molecule_ball.png/500px-Norethisterone_molecule_ball.png 1.5x" data-file-width="2000" data-file-height="1627" /></a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Norlutin, others</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">NET; Norethindrone; NSC-9564; LG-202; Ethinylnortestosterone; Norpregneninolone; Anhydrohydroxy-norprogesterone; Ethinylestrenolone; 17α-Ethynyl-19-nortestosterone; 17α-Ethynylestra-4-en-17β-ol-3-one; 17α-Hydroxy-19-norpregn-4-en-20-yn-3-one</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/norethindrone.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/a604034.html">a604034</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=Norethindrone">Norethindrone</a></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></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/Progestogen_(medication)" title="Progestogen (medication)">Progestin</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a href="/wiki/ATC_code_G03" title="ATC code G03">G03AC01</a> (<a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=G03AC01">WHO</a>) <a href="/wiki/ATC_code_G03" title="ATC code G03">G03DC02</a> (<a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=G03DC02">WHO</a>)</li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"> <ul><li><abbr class="country-name" title="Canada">CA</abbr>: <a href="/wiki/Prescription_drug" title="Prescription drug"> ℞-only</a><a href="#cite_note-1">[1]</a></li> <li><abbr class="country-name" title="United States">US</abbr>: <a href="/wiki/Prescription_drug" title="Prescription drug">℞-only</a><a href="#cite_note-2">[2]</a><a href="#cite_note-3">[3]</a><a href="#cite_note-4">[4]</a><a href="#cite_note-5">[5]</a><a href="#cite_note-6">[6]</a><a href="#cite_note-7">[7]</a><a href="#cite_note-MicronorLabel-8">[8]</a></li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a></th><td class="infobox-data">47–73% (mean 64%)<a href="#cite_note-pmid12215716-9">[9]</a><a href="#cite_note-pmid8842581-10">[10]</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">97%:<a href="#cite_note-pmid16112947-11">[11]</a> <a href="/wiki/Human_serum_albumin" title="Human serum albumin">Albumin</a>: 61%;<a href="#cite_note-pmid16112947-11">[11]</a> <a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin"><abbr title="Sex hormone-binding globulin">SHBG</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Sex hormone-binding globulin: 36%<a href="#cite_note-pmid16112947-11">[11]</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">Mainly <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a> (<a href="/wiki/Liver" title="Liver">liver</a>);<a href="#cite_note-pmid18356043-12">[12]</a> also <a href="/wiki/5%CE%B1-reductase" class="mw-redirect" title="5α-reductase">5α-</a>/<a href="/wiki/5%CE%B2-reductase" class="mw-redirect" title="5β-reductase">5β-reductase</a>, <a href="/wiki/3%CE%B1-hydroxysteroid_dehydrogenase" class="mw-redirect" title="3α-hydroxysteroid dehydrogenase"><abbr title="3α-hydroxysteroid dehydrogenase">3α-</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip 3α-hydroxysteroid dehydrogenase/<a href="/wiki/3%CE%B2-hydroxysteroid_dehydrogenase" class="mw-redirect" title="3β-hydroxysteroid dehydrogenase"><abbr title="3β-hydroxysteroid dehydrogenase">3β-HSD</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip 3β-hydroxysteroid dehydrogenase, and <a href="/wiki/Aromatase" title="Aromatase">aromatase</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">5.2–12.8 hours (mean 8.0 hours)<a href="#cite_note-pmid12215716-9">[9]</a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">(8R,9S,10R,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one</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=68-22-4">68-22-4</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/6230">6230</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=2880">2880</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/DB00717">DB00717</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.5994.html">5994</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/T18F433X4S">T18F433X4S</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/D00182">D00182</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:7627">CHEBI:7627</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/ChEMBL1162">ChEMBL1162</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/DTXSID9023380">DTXSID9023380</a> <a href="https://www.wikidata.org/wiki/Q421352#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/100.000.619">100.000.619</a> <a href="https://www.wikidata.org/wiki/Q421352#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;color:inherit;">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data">C20H26O2</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">298.426 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=C%5BC%40%5D12CC%5BC%40H%5D3%5BC%40H%5D%28%5BC%40%40H%5D1CC%5BC%40%5D2%28C%23C%29O%29CCC4%3DCC%28%3DO%29CC%5BC%40H%5D34">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">203 to 204 °C (397 to 399 °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%;">C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CC(=O)CC[C@H]34</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/C20H26O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,12,15-18,22H,4-11H2,2H3/t15-,16+,17+,18-,19-,20-/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:VIKNJXKGJWUCNN-XGXHKTLJSA-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=462262921&page2=Norethisterone">(verify)</a></td></tr></tbody></table> Norethisterone, also known as norethindrone and sold under the brand name Norlutin among others, is a <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestin</a> medication used in <a href="/wiki/Birth_control_pill" class="mw-redirect" title="Birth control pill">birth control pills</a>, <a href="/wiki/Menopausal_hormone_therapy" class="mw-redirect" title="Menopausal hormone therapy">menopausal hormone therapy</a>, and for the treatment of <a href="/wiki/Gynecological_disorder" class="mw-redirect" title="Gynecological disorder">gynecological disorders</a>.<a href="#cite_note-pmid16112947-11">[11]</a><a href="#cite_note-pmid8520623-13">[13]</a> The medication is available in both low-dose and high-dose formulations and both alone and in combination with an <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogen</a>.<a href="#cite_note-pmid8520623-13">[13]</a><a href="#cite_note-AldenLowdermilk2013-14">[14]</a> It is used <a href="/wiki/Oral_administration" title="Oral administration">by mouth</a> or, as <a href="/wiki/Norethisterone_enanthate" title="Norethisterone enanthate">norethisterone enanthate</a>, by <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">injection into muscle</a>.<a href="#cite_note-pmid16112947-11">[11]</a><a href="#cite_note-pmid8520623-13">[13]</a><a href="#cite_note-pmid2170822-15">[15]</a> <a href="/wiki/Side_effect" title="Side effect">Side effects</a> of norethisterone include <a href="/wiki/Menstrual_irregularities" class="mw-redirect" title="Menstrual irregularities">menstrual irregularities</a>, <a href="/wiki/Headache" title="Headache">headaches</a>, <a href="/wiki/Nausea" title="Nausea">nausea</a>, <a href="/wiki/Breast_tenderness" class="mw-redirect" title="Breast tenderness">breast tenderness</a>, <a href="/wiki/Mood_(psychology)" title="Mood (psychology)">mood</a> changes, <a href="/wiki/Acne" title="Acne">acne</a>, <a href="/wiki/Hirsutism" title="Hirsutism">increased hair growth</a>.<a href="#cite_note-Aygestin-Label-16">[16]</a><a href="#cite_note-pmid14450719-17">[17]</a> Norethisterone is a progestin, or a <a href="/wiki/Synthetic_compound" class="mw-redirect" title="Synthetic compound">synthetic</a> <a href="/wiki/Progestogen_(medication)" title="Progestogen (medication)">progestogen</a>, and hence is an <a href="/wiki/Agonist" title="Agonist">agonist</a> of the <a href="/wiki/Progesterone_receptor" title="Progesterone receptor">progesterone receptor</a>, the <a href="/wiki/Biological_target" title="Biological target">biological target</a> of progestogens like <a href="/wiki/Progesterone" title="Progesterone">progesterone</a>.<a href="#cite_note-pmid16112947-11">[11]</a><a href="#cite_note-pmid8520623-13">[13]</a> It has weak <a href="/wiki/Androgen" title="Androgen">androgenic</a> and <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogenic</a> activity, mostly at high dosages, and no other important <a href="/wiki/Hormonal_agent" class="mw-redirect" title="Hormonal agent">hormonal</a> activity.<a href="#cite_note-pmid16112947-11">[11]</a><a href="#cite_note-HumansOrganization2007-18">[18]</a> Norethisterone was discovered in 1951 and was one of the first progestins to be developed.<a href="#cite_note-DjerassiMiramontes1954-19">[19]</a><a href="#cite_note-Shoupe2007-20">[20]</a><a href="#cite_note-Marks2010-21">[21]</a> It was first introduced for medical use on its own in 1957 and was introduced in combination with an estrogen for use as a birth control pill in 1963.<a href="#cite_note-Marks2010-21">[21]</a><a href="#cite_note-Publishing2013-22">[22]</a> It is sometimes referred to as a "first-generation" progestin.<a href="#cite_note-HatcherM.D.2007-23">[23]</a><a href="#cite_note-Gunasheela2011-24">[24]</a> Like <a href="/wiki/Desogestrel" title="Desogestrel">desogestrel</a> and <a href="/wiki/Norgestrel" title="Norgestrel">Norgestrel</a>, Norethisterone is available as a <a href="/wiki/Progestogen-only_pill" title="Progestogen-only pill">progestogen-only "mini pill"</a> for birth control.<a href="#cite_note-pmid24226383-25">[25]</a><a href="#cite_note-pmid14759612-26">[26]</a><a href="#cite_note-27">[27]</a> Norethisterone is marketed widely throughout the world.<a href="#cite_note-Drugs.com-28">[28]</a> It is available as a <a href="/wiki/Generic_drug" title="Generic drug">generic medication</a>.<a href="#cite_note-Drugs.com-Generic-29">[29]</a> In 2022, it was the 135th most commonly prescribed medication in the United States, with more than 4 million prescriptions.<a href="#cite_note-30">[30]</a><a href="#cite_note-31">[31]</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-32">[32]</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=Norethisterone&action=edit&section=1" title="Edit section: Medical uses">edit</a>]</div> Norethisterone is used as a hormonal contraceptive in combination with an estrogen – usually <a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">ethinylestradiol</a> (EE) – in <a href="/wiki/Combined_oral_contraceptive_pill" title="Combined oral contraceptive pill">combined oral contraceptive pills</a> and alone in <a href="/wiki/Progestogen-only_pill" title="Progestogen-only pill">progestogen-only pills</a>. Another medical use of norethisterone is to alleviate <a href="/wiki/Endometriosis" title="Endometriosis">endometriosis</a> related pain. In fact, 50% of patients who received medical or surgical treatment for endometriosis-related pelvic pain have benefited from <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestin</a> therapy. This could be due to the fact that norethisterone induces endometrial proliferation during secretory phase, which has been shown to alleviate endometrial pain complaints. Another way in which norethisterone may be acting to reduce endometrial pain is via inhibition of <a href="/wiki/Ovulation" title="Ovulation">ovulation</a>. Endometriosis pain and discomfort is worse during ovulation.<a href="#cite_note-33">[33]</a> <table class="wikitable floatright" style="width:45%;"> <caption><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:Formulations_and_brand_names_of_norethisterone_and_esters" title="Template:Formulations and brand names of norethisterone and esters"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Formulations_and_brand_names_of_norethisterone_and_esters" title="Template talk:Formulations and brand names of norethisterone and esters"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Formulations_and_brand_names_of_norethisterone_and_esters" title="Special:EditPage/Template:Formulations and brand names of norethisterone and esters"><abbr title="Edit this template">e</abbr></a></li></ul></div> Formulations and brand names of norethisterone and esters </caption> <tbody><tr> <th style="width:100px;">Composition</th> <th style="width:100px;">Dose</th> <th style="width:100px;">Brand names</th> <th style="width:100px;">Use </th></tr> <tr> <td>NET only</td> <td>Low (e.g., 0.35 mg)</td> <td>Multiple<a href="#cite_note-34">[a]</a></td> <td><a href="/wiki/Progestogen-only_oral_contraceptive" class="mw-redirect" title="Progestogen-only oral contraceptive">Progestogen-only oral contraceptive</a> </td></tr> <tr> <td>NET or NETA only</td> <td>High (e.g., 5 mg, 10 mg)</td> <td>Multiple<a href="#cite_note-35">[b]</a></td> <td><a href="/wiki/Gynecological_disorder" class="mw-redirect" title="Gynecological disorder">Gynecological disorders</a> and other uses </td></tr> <tr> <td>NETE only</td> <td>Injection (e.g., 200 mg)</td> <td>Multiple<a href="#cite_note-36">[c]</a></td> <td><a href="/wiki/Progestogen-only_injectable_contraceptive" title="Progestogen-only injectable contraceptive">Progestogen-only injectable contraceptive</a> </td></tr> <tr> <td>NET or NETA with <a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">ethinylestradiol</a></td> <td>Low (e.g., 0.4 mg, 0.5 mg, 0.75 mg, 1 mg, 1.5 mg)</td> <td>Multiple<a href="#cite_note-37">[d]</a></td> <td><a href="/wiki/Combined_oral_contraceptive" class="mw-redirect" title="Combined oral contraceptive">Combined oral contraceptive</a> </td></tr> <tr> <td>NET with <a href="/wiki/Mestranol" title="Mestranol">mestranol</a></td> <td>Low (e.g., 1 mg, 2 mg)</td> <td>Multiple<a href="#cite_note-38">[e]</a></td> <td>Combined oral contraceptive </td></tr> <tr> <td>NETA with <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a></td> <td>Low (e.g., 0.1 mg, 0.5 mg)</td> <td>Multiple<a href="#cite_note-39">[f]</a></td> <td><a href="/wiki/Combined_menopausal_hormone_therapy" class="mw-redirect" title="Combined menopausal hormone therapy">Combined menopausal hormone therapy</a> </td></tr> <tr> <td>NETE with <a href="/wiki/Estradiol_valerate" title="Estradiol valerate">estradiol valerate</a></td> <td>Injection (e.g., 50 mg)</td> <td>Multiple<a href="#cite_note-40">[g]</a></td> <td><a href="/wiki/Combined_injectable_contraceptive" class="mw-redirect" title="Combined injectable contraceptive">Combined injectable contraceptive</a> </td></tr> <tr> <td colspan="4" style="background-color:#eaecf0; text-align: center;">Abbreviations: NET = Norethisterone. NETA = <a href="/wiki/Norethisterone_acetate" title="Norethisterone acetate">Norethisterone acetate</a>. NETE = <a href="/wiki/Norethisterone_enanthate" title="Norethisterone enanthate">Norethisterone enanthate</a>. Sources: <a href="#cite_note-Drugs.com_-41">[34]</a><a href="#cite_note-Drugs@FDA-42">[35]</a> <a href="#cite_note-IndexNominum2000-43">[36]</a><a href="#cite_note-HumansCancer1999-44">[37]</a> <style data-mw-deduplicate="TemplateStyles:r1214851843">.mw-parser-output .hidden-begin{box-sizing:border-box;width:100%;padding:5px;border:none;font-size:95%}.mw-parser-output .hidden-title{font-weight:bold;line-height:1.6;text-align:left}.mw-parser-output .hidden-content{text-align:left}@media all and (max-width:500px){.mw-parser-output .hidden-begin{width:auto!important;clear:none!important;float:none!important}}</style><div class="hidden-begin mw-collapsible mw-collapsed" style=""><div class="hidden-title skin-nightmode-reset-color" style="text-align:center;">Notes:</div><div class="hidden-content mw-collapsible-content" style=""> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-lower-alpha"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-34"><a href="#cite_ref-34">^</a> Camila, Errin, Heather, Jencycla, Jolivette, Locilan, Micro-Novum, Micronovum, Micronor, Nor-QD, Nora, Noriday, Ortho Micronor </li> <li id="cite_note-35"><a href="#cite_ref-35">^</a> Aygestin, Lupaneta Pack (combination pack with <a href="/wiki/Leuprorelin" title="Leuprorelin">leuprorelin</a>), Norcolut, Norlutate, Primolut N, Primolut Nor, SH-420, Utovlan </li> <li id="cite_note-36"><a href="#cite_ref-36">^</a> Depocon, Doryxas, NET-EN, Noristerat, Norigest, Nur-Isterate </li> <li id="cite_note-37"><a href="#cite_ref-37">^</a> Aranelle, Balziva, Binovum, Brevicon, Brevinor, Briellyn, Cyclafem, Dasetta, Estrostep, Femcon, Generess, Gildagia, Gildess, Jinteli, Junel, Larin, Leena, Lo Loestrin, Lo Minastrin, Loestrin, Lolo, Lomedia, Microgestin, Minastrin, Modicon, Nelova, Norimin, Norinyl, Nortrel, Ortho, Ortho-Novum, Ovcon, Ovysmen, Philith, Primella, Select, Synphase, Synphasic, Tilia, Tri-Legest, Tri-Norinyl, Trinovum, Vyfemla, Wera, Wymzya, Zenchent, Zeosa </li> <li id="cite_note-38"><a href="#cite_ref-38">^</a> Norethin, Noriday, Norinyl, Norquen, Ortho-Novum, Sophia </li> <li id="cite_note-39"><a href="#cite_ref-39">^</a> Activella, Activelle, Alyacen, Cliane, Climagest, Climesse, Cliovelle, CombiPatch, Elleste Duet, Estalis, Estropause, Eviana, Evorel, Kliane, Kliofem, Kliogest, Kliovance, Mesigyna, Mesygest, Mimvey, Necon, Novofem, Nuvelle, Sequidot, Systen, Trisequens </li> <li id="cite_note-40"><a href="#cite_ref-40">^</a> Chinese Injectable No. 3, Efectimes, Ginediol, Mesigyna, Mesilar, Meslart, Mesocept, Mesygest, Nofertyl, Nofertyl Lafrancol, Noregyna, Norestrin, Norifam, Norigynon, Nostidyn, Sexseg, Solouna </li> </ol></div></div></div></div> </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Contraindications">Contraindications</h2>[<a href="/w/index.php?title=Norethisterone&action=edit&section=2" title="Edit section: Contraindications">edit</a>]</div> High-dose (10 mg/day) norethisterone has been associated with <a href="/wiki/Hepatic_veno-occlusive_disease" title="Hepatic veno-occlusive disease">hepatic veno-occlusive disease</a>, and because of this adverse effect, norethisterone should not be given to patients undergoing <a href="https://en.wiktionary.org/wiki/allogeneic" class="extiw" title="wikt:allogeneic">allogeneic</a> <a href="/wiki/Bone_marrow_transplantation" class="mw-redirect" title="Bone marrow transplantation">bone marrow transplantation</a>, as it has been associated with substantially lower one-year survival post-transplantation.<a href="#cite_note-Aronson2009-45">[38]</a><a href="#cite_note-pmid9845522-46">[39]</a> <div class="mw-heading mw-heading2"><h2 id="Side_effects">Side effects</h2>[<a href="/w/index.php?title=Norethisterone&action=edit&section=3" title="Edit section: Side effects">edit</a>]</div> At contraceptive and hormone replacement dosages (0.35 to 1 mg/day), norethisterone has essentially progestogenic <a href="/wiki/Side_effect" title="Side effect">side effects</a> only. In most clinical studies of norethisterone for contraception or menopausal hormone therapy, the drug has been combined with an estrogen, and for this reason, it is difficult to determine which of the side effects were caused by norethisterone and which of them were caused by estrogen in such research. However, <a href="/wiki/Norethisterone_enanthate" title="Norethisterone enanthate">norethisterone enanthate</a>, an intramuscularly administered prodrug of norethisterone which is used as a long-acting contraceptive, is used without an estrogen, and hence can be employed as a surrogate for norethisterone in terms of understanding its effects and <a href="/wiki/Tolerability" title="Tolerability">tolerability</a>. In clinical studies, the most common side effect with norethisterone enanthate has been <a href="/wiki/Menstrual_disturbance" class="mw-redirect" title="Menstrual disturbance">menstrual disturbances</a>, including <a href="/wiki/Dysfunctional_uterine_bleeding" class="mw-redirect" title="Dysfunctional uterine bleeding">prolonged bleeding or spotting</a> and <a href="/wiki/Amenorrhea" title="Amenorrhea">amenorrhea</a>.<a href="#cite_note-Aronson2009-45">[38]</a>: 253  Other side effects have included periodic <a href="/wiki/Abdominal_bloating" class="mw-redirect" title="Abdominal bloating">abdominal bloating</a> and <a href="/wiki/Breast_tenderness" class="mw-redirect" title="Breast tenderness">breast tenderness</a>, both of which are thought to be due to <a href="/wiki/Water_retention_(medicine)" class="mw-redirect" title="Water retention (medicine)">water retention</a> and can be relieved with <a href="/wiki/Diuretic" title="Diuretic">diuretics</a>.<a href="#cite_note-Aronson2009-45">[38]</a>: 253  There has been no association with <a href="/wiki/Weight_gain" title="Weight gain">weight gain</a>, and <a href="/wiki/Blood_pressure" title="Blood pressure">blood pressure</a>, <a href="/wiki/Blood_clotting" class="mw-redirect" title="Blood clotting">blood clotting</a>, and <a href="/wiki/Glucose_tolerance" class="mw-redirect" title="Glucose tolerance">glucose tolerance</a> have all remained normal.<a href="#cite_note-Aronson2009-45">[38]</a>: 253  However, a decrease in <a href="/wiki/HDL_cholesterol" class="mw-redirect" title="HDL cholesterol"><abbr title="high-density lipoprotein">HDL</abbr> cholesterol</a> has been observed.<a href="#cite_note-Aronson2009-45">[38]</a>: 253  At high doses (5 to 60 mg/day), for instance those used in the treatment of gynecological disorders, norethisterone can cause <a href="/wiki/Hypogonadism" title="Hypogonadism">hypogonadism</a> due to its <a href="/wiki/Antigonadotropic" class="mw-redirect" title="Antigonadotropic">antigonadotropic</a> effects and can have estrogenic and weak androgenic side effects. High doses of norethisterone acetate (10 mg/day) have been associated with abnormal <a href="/wiki/Liver_function_tests" title="Liver function tests">liver function tests</a>, including significant <a href="/wiki/Elevated_liver_enzymes" class="mw-redirect" title="Elevated liver enzymes">elevations in liver enzymes</a>.<a href="#cite_note-pmid15571489-47">[40]</a><a href="#cite_note-CorniaAnawalt2005-48">[41]</a><a href="#cite_note-pmid11836281-49">[42]</a> These <a href="/wiki/Liver_enzyme" class="mw-redirect" title="Liver enzyme">liver enzymes</a> included <a href="/wiki/Lactate_dehydrogenase" title="Lactate dehydrogenase">lactate dehydrogenase</a> and <a href="/wiki/Glutamate_pyruvate_transaminase" class="mw-redirect" title="Glutamate pyruvate transaminase">glutamate pyruvate transaminase</a>.<a href="#cite_note-pmid11836281-49">[42]</a> Although they were described as having no clinical relevance,<a href="#cite_note-pmid11836281-49">[42]</a> the elevated liver enzymes associated with norethisterone acetate may have precluded its further development for male hormonal contraception.<a href="#cite_note-pmid15571489-47">[40]</a><a href="#cite_note-CorniaAnawalt2005-48">[41]</a> <div class="mw-heading mw-heading3"><h3 id="Androgenic">Androgenic</h3>[<a href="/w/index.php?title=Norethisterone&action=edit&section=4" title="Edit section: Androgenic">edit</a>]</div> Due to its weak androgenic activity, norethisterone can produce androgenic <a href="/wiki/Side_effect" title="Side effect">side effects</a> such as <a href="/wiki/Acne" title="Acne">acne</a>, <a href="/wiki/Hirsutism" title="Hirsutism">hirsutism</a>, and <a href="/wiki/Voice_change" title="Voice change">voice changes</a> of slight severity in some women at high dosages (e.g., 10 to 40 mg/day).<a href="#cite_note-pmid14450719-17">[17]</a> This is notably not the case with <a href="/wiki/Combined_oral_contraceptive" class="mw-redirect" title="Combined oral contraceptive">combined oral contraceptives</a> that contain norethisterone and EE, however.<a href="#cite_note-HumansOrganization2007-18">[18]</a> Such formulations contain low dosages of norethisterone (0.35 to 1 mg/day)<a href="#cite_note-HumansOrganization2007-18">[18]</a> in combination with <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogen</a> and are actually associated with improvement in acne symptoms.<a href="#cite_note-pmid20159314-50">[43]</a><a href="#cite_note-CO-51">[44]</a> In accordance, they are in fact approved by the <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration"><abbr title="Food and Drug Administration">FDA</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 Food and Drug Administration for the treatment of acne in women in the United States.<a href="#cite_note-pmid20159314-50">[43]</a><a href="#cite_note-CO-51">[44]</a> The improvement in acne symptoms is believed to be due to a 2- to 3-fold increase in <a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin">sex hormone-binding globulin</a> (SHBG) levels and a consequent decrease in free <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> levels caused by EE, which results in an overall decrease in androgenic signaling in the body.<a href="#cite_note-pmid15663340-52">[45]</a> The <a href="/wiki/Sebaceous_gland" title="Sebaceous gland">sebaceous glands</a> are highly androgen-sensitive and their size and activity are potential markers of androgenic effect.<a href="#cite_note-pmid5843402-53">[46]</a> A high dosage of 20 mg/day norethisterone or norethisterone acetate has been found to significantly stimulate the sebaceous glands, whereas lower dosages of 5 mg/day and 2.5 mg/day norethisterone and norethisterone acetate, respectively, did not significantly stimulate sebum production and were consequently regarded as devoid of significant androgenicity.<a href="#cite_note-pmid5843402-53">[46]</a> Conversely, dosages of norethisterone of 0.5 to 3 mg/day have been found to dose-dependently decrease SHBG levels (and hence to suppress hepatic SHBG production), which is another highly sensitive marker of androgenicity.<a href="#cite_note-pmid9494772-54">[47]</a> A large clinical study of high to very high oral dosages of norethisterone (10 to 40 mg/day) administered for prolonged periods of time (4 to 35 weeks) to prevent <a href="/wiki/Miscarriage" title="Miscarriage">miscarriage</a> in <a href="/wiki/Pregnancy" title="Pregnancy">pregnant</a> women found that 5.5% of the women experienced mild androgenic side effects such as mild <a href="/wiki/Voice_change" title="Voice change">voice changes</a> (<a href="/wiki/Hoarseness" class="mw-redirect" title="Hoarseness">hoarseness</a>), acne, and <a href="/wiki/Hirsutism" title="Hirsutism">hirsutism</a> and that 18.3% of female infants born to the mothers showed, in most cases only slight, <a href="/wiki/Virilization" title="Virilization">virilization</a> of the <a href="/wiki/Genital" class="mw-redirect" title="Genital">genitals</a>.<a href="#cite_note-pmid14450719-17">[17]</a> Maternal androgenic symptoms occurred most often in women who received a dosage of norethisterone of 30 mg/day or more for a period of 15 weeks or longer.<a href="#cite_note-pmid14450719-17">[17]</a> In the female infants who experienced virilization of the genitals, the sole manifestation in 86.7% of the cases was varied but almost always slight enlargement of the clitoris.<a href="#cite_note-pmid14450719-17">[17]</a> In the remaining 13.3% of the affected cases, marked clitoral enlargement and partial fusion of the <a href="/wiki/Labioscrotal_swelling" title="Labioscrotal swelling">labioscrotal folds</a> occurred.<a href="#cite_note-pmid14450719-17">[17]</a> The dosages used in these cases were 20 to 40 mg/day.<a href="#cite_note-pmid14450719-17">[17]</a> In a letter to the editor on the topic of virilization caused by high dosages of norethisterone acetate in women, a physician expressed that they had not observed the "slightest evidence of virilization" and that there had "certainly been no hirsutism nor any voice changes" in 55 women with advanced breast cancer that they had treated with 30 to 60 mg/day norethisterone for up to six months.<a href="#cite_note-Curwen1962-55">[48]</a> High-dosage norethisterone has been used to suppress <a href="/wiki/Menstruation" title="Menstruation">menstruation</a> in women with severe <a href="/wiki/Intellectual_disability" title="Intellectual disability">intellectual disability</a> who were incapable of handling their own menses.<a href="#cite_note-RoxburghWest1973-56">[49]</a><a href="#cite_note-RoxburghWest1974-57">[50]</a> A study of 118 nulliparous women treated with 5 mg/day norethisterone for a period of 2 to 30 months found that the drug was effective in producing <a href="/wiki/Amenorrhea" title="Amenorrhea">amenorrhea</a> in 86% of the women, with <a href="/wiki/Breakthrough_bleeding" class="mw-redirect" title="Breakthrough bleeding">breakthrough bleeding</a> occurring in the remaining 14%.<a href="#cite_note-RoxburghWest1973-56">[49]</a> Side effects including <a href="/wiki/Weight_gain" title="Weight gain">weight gain</a>, <a href="/wiki/Hirsutism" title="Hirsutism">hirsutism</a>, <a href="/wiki/Acne" title="Acne">acne</a>, <a href="/wiki/Headache" title="Headache">headache</a>, <a href="/wiki/Nausea" title="Nausea">nausea</a>, and <a href="/wiki/Vomiting" title="Vomiting">vomiting</a> all did not appear to increase in incidence and no "disturbing side effects" were noted in any of the women.<a href="#cite_note-RoxburghWest1973-56">[49]</a><a href="#cite_note-RoxburghWest1974-57">[50]</a> Another study of 5 mg/day norethisterone in 132 women also made no mention of androgenic side effects.<a href="#cite_note-pmid14272499-58">[51]</a> These findings suggest little to no risk of androgenic side effects with norethisterone at a dosage of 5 mg/day.<a href="#cite_note-RoxburghWest1973-56">[49]</a><a href="#cite_note-RoxburghWest1974-57">[50]</a> A study of 194 women treated with 5 to 15 mg/day norethisterone acetate for a median duration of 13 months of therapy to suppress symptoms of <a href="/wiki/Endometriosis" title="Endometriosis">endometriosis</a> observed no side effects in 55.2% of patients, weight gain in 16.1%, acne in 9.9%, <a href="/wiki/Mood_lability" class="mw-redirect" title="Mood lability">mood lability</a> in 8.9%, <a href="/wiki/Hot_flash" title="Hot flash">hot flashes</a> in 8.3%, and voice deepening in two women (1.0%).<a href="#cite_note-pmid22154396-59">[52]</a> <div class="mw-heading mw-heading3"><h3 id="Estrogenic">Estrogenic</h3>[<a href="/w/index.php?title=Norethisterone&action=edit&section=5" title="Edit section: Estrogenic">edit</a>]</div> Norethisterone is weakly <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogenic</a> (via conversion into its <a href="/wiki/Metabolite" title="Metabolite">metabolite</a> EE), and for this reason, it has been found at high dosages to be associated with high rates of estrogenic side effects such as <a href="/wiki/Breast_enlargement" title="Breast enlargement">breast enlargement</a> in women and <a href="/wiki/Gynecomastia" title="Gynecomastia">gynecomastia</a> in men, but also with improvement of <a href="/wiki/Menopause" title="Menopause">menopausal</a> <a href="/wiki/Symptom" class="mw-redirect" title="Symptom">symptoms</a> in postmenopausal women.<a href="#cite_note-pmid13942007-60">[53]</a> It has been suggested that very high dosages (e.g., 40 mg/day, which are sometimes used in clinical practice for various indications) of norethisterone acetate (and by extension norethisterone) may result in an increased risk of <a href="/wiki/Venous_thromboembolism" class="mw-redirect" title="Venous thromboembolism">venous thromboembolism</a> (VTE) analogously to high dosages (above 50 μg/day) of EE, and that even doses of norethisterone acetate of 10 to 20 mg, which correspond to EE doses of approximately 20 to 30 μg/day, may in certain women be associated with increased risk.<a href="#cite_note-pmid17341557-61">[54]</a><a href="#cite_note-ConnollyBritton2017-62">[55]</a> A study also found that ethinylestradiol and norethisterone had a greater influence on coagulation factors when the dose of norethisterone was 3 or 4 mg than when it was 1 mg.<a href="#cite_note-pmid28712325-63">[56]</a> This might have been due to additional ethinylestradiol generated by higher doses of norethisterone.<a href="#cite_note-pmid28712325-63">[56]</a> <div class="mw-heading mw-heading2"><h2 id="Overdose">Overdose</h2>[<a href="/w/index.php?title=Norethisterone&action=edit&section=6" title="Edit section: Overdose">edit</a>]</div> There have been no reports of serious <a href="/wiki/Side_effect" title="Side effect">side effects</a> with overdose of norethisterone, even in small children.<a href="#cite_note-MicronorLabel-8">[8]</a> As such, overdose usually does not require treatment.<a href="#cite_note-MicronorLabel-8">[8]</a> High dosages of as much as 60 mg/day norethisterone have been studied for extended treatment durations without serious adverse effects described.<a href="#cite_note-Curwen1962-55">[48]</a> <div class="mw-heading mw-heading2"><h2 id="Interactions">Interactions</h2>[<a href="/w/index.php?title=Norethisterone&action=edit&section=7" title="Edit section: Interactions">edit</a>]</div> <a href="/wiki/5%CE%B1-Reductase" title="5α-Reductase">5α-Reductase</a> plays an important role in the <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> of norethisterone, and <a href="/wiki/5%CE%B1-reductase_inhibitor" class="mw-redirect" title="5α-reductase inhibitor">5α-reductase inhibitors</a> such as <a href="/wiki/Finasteride" title="Finasteride">finasteride</a> and <a href="/wiki/Dutasteride" title="Dutasteride">dutasteride</a> can inhibit its metabolism.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] Norethisterone is partially metabolized via <a href="/wiki/Hydroxylation" title="Hydroxylation">hydroxylation</a> by <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a>, and <a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibitors</a> and <a href="/wiki/Enzyme_inducer" title="Enzyme inducer">inducers</a> of CYP3A4 can significantly alter circulating levels of norethisterone.<a href="#cite_note-pmid18356043-12">[12]</a> For instance, the CYP3A4 inducers <a href="/wiki/Rifampicin" title="Rifampicin">rifampicin</a> and <a href="/wiki/Bosentan" title="Bosentan">bosentan</a> have been found to decrease norethisterone exposure by 42% and 23%, respectively, and the CYP3A4 inducers <a href="/wiki/Carbamazepine" title="Carbamazepine">carbamazepine</a> and <a href="/wiki/St._John%27s_wort" class="mw-redirect" title="St. John's wort">St. John's wort</a> have also been found to accelerate norethisterone clearance.<a href="#cite_note-pmid18356043-12">[12]</a> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2>[<a href="/w/index.php?title=Norethisterone&action=edit&section=8" title="Edit section: Pharmacology">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Pharmacodynamics">Pharmacodynamics</h3>[<a href="/w/index.php?title=Norethisterone&action=edit&section=9" title="Edit section: Pharmacodynamics">edit</a>]</div> Norethisterone is a potent <a href="/wiki/Progestogen_(medication)" title="Progestogen (medication)">progestogen</a> and a weak <a href="/wiki/Androgen" title="Androgen">androgen</a> and <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogen</a>.<a href="#cite_note-pmid16112947-11">[11]</a> That is, it is a potent <a href="/wiki/Agonist" title="Agonist">agonist</a> of the <a href="/wiki/Progesterone_receptor" title="Progesterone receptor">progesterone receptor</a> (PR) and a weak agonist of the <a href="/wiki/Androgen_receptor" title="Androgen receptor">androgen receptor</a> (AR) and the <a href="/wiki/Estrogen_receptor" title="Estrogen receptor">estrogen receptor</a> (ER).<a href="#cite_note-pmid16112947-11">[11]</a> Norethisterone itself has insignificant <a href="/wiki/Affinity_(pharmacology)" class="mw-redirect" title="Affinity (pharmacology)">affinity</a> for the ER; its estrogenic activity is from an <a href="/wiki/Active_metabolite" title="Active metabolite">active metabolite</a> that is formed in very small amounts, <a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">ethinylestradiol</a> (EE), which is a very potent estrogen.<a href="#cite_note-pmid16112947-11">[11]</a> Norethisterone and its metabolites have negligible affinity for the <a href="/wiki/Glucocorticoid_receptor" title="Glucocorticoid receptor">glucocorticoid receptor</a> (GR) and <a href="/wiki/Mineralocorticoid_receptor" title="Mineralocorticoid receptor">mineralocorticoid receptor</a> (MR) and hence have no <a href="/wiki/Glucocorticoid" title="Glucocorticoid">glucocorticoid</a>, <a href="/wiki/Antiglucocorticoid" title="Antiglucocorticoid">antiglucocorticoid</a>, <a href="/wiki/Mineralocorticoid" title="Mineralocorticoid">mineralocorticoid</a>, or <a href="/wiki/Antimineralocorticoid" class="mw-redirect" title="Antimineralocorticoid">antimineralocorticoid</a> activity.<a href="#cite_note-pmid16112947-11">[11]</a> <table class="wikitable mw-collapsible mw-collapsed" style="text-align:left; margin-left:auto; margin-right:auto; border:none;"> <caption class="nowrap"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Relative_affinities_of_norethisterone,_metabolites,_and_prodrugs" title="Template:Relative affinities of norethisterone, metabolites, and prodrugs"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Relative_affinities_of_norethisterone,_metabolites,_and_prodrugs" title="Template talk:Relative affinities of norethisterone, metabolites, and prodrugs"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Relative_affinities_of_norethisterone,_metabolites,_and_prodrugs" title="Special:EditPage/Template:Relative affinities of norethisterone, metabolites, and prodrugs"><abbr title="Edit this template">e</abbr></a></li></ul></div> Relative affinities (%) of norethisterone, metabolites, and prodrugs </caption> <tbody><tr> <th>Compound</th> <th>Typea</th> <th><a href="/wiki/Progesterone_receptor" title="Progesterone receptor"><abbr title="Progesterone receptor">PR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Progesterone receptor</th> <th><a href="/wiki/Androgen_receptor" title="Androgen receptor"><abbr title="Androgen receptor">AR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Androgen receptor</th> <th><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor</th> <th><a href="/wiki/Glucocorticoid_receptor" title="Glucocorticoid receptor"><abbr title="Glucocorticoid receptor">GR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Glucocorticoid receptor</th> <th><a href="/wiki/Mineralocorticoid_receptor" title="Mineralocorticoid receptor"><abbr title="Mineralocorticoid receptor">MR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Mineralocorticoid receptor</th> <th><a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin"><abbr title="Sex hormone-binding globulin">SHBG</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Sex hormone-binding globulin</th> <th><a href="/wiki/Corticosteroid_binding_globulin" class="mw-redirect" title="Corticosteroid binding globulin"><abbr title="Corticosteroid binding globulin">CBG</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Corticosteroid binding globulin </th></tr> <tr> <td>Norethisterone</td> <td>–</td> <td>67–75</td> <td>15</td> <td>0</td> <td>0–1</td> <td>0–3</td> <td>16</td> <td>0 </td></tr> <tr> <td style="padding-left:1.5em;"><a href="/wiki/5%CE%B1-Dihydronorethisterone" title="5α-Dihydronorethisterone">5α-Dihydronorethisterone</a></td> <td>Metabolite</td> <td>25</td> <td>27</td> <td>0</td> <td>0</td> <td>?</td> <td>?</td> <td>? </td></tr> <tr> <td style="padding-left:1.5em;">3α,5α-Tetrahydronorethisterone</td> <td>Metabolite</td> <td>1</td> <td>0</td> <td>0–1</td> <td>0</td> <td>?</td> <td>?</td> <td>? </td></tr> <tr> <td style="padding-left:1.5em;">3α,5β-Tetrahydronorethisterone</td> <td>Metabolite</td> <td>?</td> <td>0</td> <td>0</td> <td>?</td> <td>?</td> <td>?</td> <td>? </td></tr> <tr> <td style="padding-left:1.5em;">3β,5α-Tetrahydronorethisterone</td> <td>Metabolite</td> <td>1</td> <td>0</td> <td>0–8</td> <td>0</td> <td>?</td> <td>?</td> <td>? </td></tr> <tr> <td style="padding-left:1.5em;"><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a></td> <td>Metabolite</td> <td>15–25</td> <td>1–3</td> <td>112</td> <td>1–3</td> <td>0</td> <td>0.18</td> <td>0 </td></tr> <tr> <td><a href="/wiki/Norethisterone_acetate" title="Norethisterone acetate">Norethisterone acetate</a></td> <td>Prodrug</td> <td>20</td> <td>5</td> <td>1</td> <td>0</td> <td>0</td> <td>?</td> <td>? </td></tr> <tr> <td><a href="/wiki/Norethisterone_enanthate" title="Norethisterone enanthate">Norethisterone enanthate</a></td> <td>Prodrug</td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>? </td></tr> <tr> <td><a href="/wiki/Noretynodrel" title="Noretynodrel">Noretynodrel</a></td> <td>Prodrug</td> <td>6</td> <td>0</td> <td>2</td> <td>0</td> <td>0</td> <td>0</td> <td>0 </td></tr> <tr> <td><a href="/wiki/Etynodiol" title="Etynodiol">Etynodiol</a></td> <td>Prodrug</td> <td>1</td> <td>0</td> <td>11–18</td> <td>0</td> <td>?</td> <td>?</td> <td>? </td></tr> <tr> <td><a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">Etynodiol diacetate</a></td> <td>Prodrug</td> <td>1</td> <td>0</td> <td>0</td> <td>0</td> <td>0</td> <td>?</td> <td>? </td></tr> <tr> <td><a href="/wiki/Lynestrenol" title="Lynestrenol">Lynestrenol</a></td> <td>Prodrug</td> <td>1</td> <td>1</td> <td>3</td> <td>0</td> <td>0</td> <td>?</td> <td>? </td></tr> <tr> <td colspan="9" style="width: 1px; background-color:#eaecf0; text-align: center;">Notes: Values are percentages (%). Reference <a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">ligands</a> (100%) were <a href="/wiki/Promegestone" title="Promegestone">promegestone</a> for the <a href="/wiki/Progesterone_receptor" title="Progesterone receptor"><abbr title="progesterone receptor">PR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip progesterone receptor, <a href="/wiki/Metribolone" title="Metribolone">metribolone</a> for the <a href="/wiki/Androgen_receptor" title="Androgen receptor"><abbr title="androgen receptor">AR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip androgen receptor, <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a> for the <a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip estrogen receptor, <a href="/wiki/Dexamethasone" title="Dexamethasone">dexamethasone</a> for the <a href="/wiki/Glucocorticoid_receptor" title="Glucocorticoid receptor"><abbr title="glucocorticoid receptor">GR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip glucocorticoid receptor, <a href="/wiki/Aldosterone" title="Aldosterone">aldosterone</a> for the <a href="/wiki/Mineralocorticoid_receptor" title="Mineralocorticoid receptor"><abbr title="mineralocorticoid receptor">MR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip mineralocorticoid receptor, <a href="/wiki/Androstanolone" title="Androstanolone">dihydrotestosterone</a> for <a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin"><abbr title="sex hormone-binding globulin">SHBG</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip sex hormone-binding globulin, and <a href="/wiki/Hydrocortisone" title="Hydrocortisone">cortisol</a> for <a href="/wiki/Corticosteroid-binding_globulin" class="mw-redirect" title="Corticosteroid-binding globulin"><abbr title="Corticosteroid-binding globulin">CBG</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Corticosteroid-binding globulin. Footnotes: a = <a href="/wiki/Active_metabolite" title="Active metabolite">Active</a> or inactive <a href="/wiki/Metabolite" title="Metabolite">metabolite</a>, <a href="/wiki/Prodrug" title="Prodrug">prodrug</a>, or neither of norethisterone. Sources: See template. </td></tr></tbody></table> <div class="mw-heading mw-heading4"><h4 id="Progestogenic_activity">Progestogenic activity</h4>[<a href="/w/index.php?title=Norethisterone&action=edit&section=10" title="Edit section: Progestogenic activity">edit</a>]</div> Norethisterone is a potent <a href="/wiki/Progestogen_(medication)" title="Progestogen (medication)">progestogen</a> and binds to the PR with approximately 150% of the <a href="/wiki/Affinity_(pharmacology)" class="mw-redirect" title="Affinity (pharmacology)">affinity</a> of <a href="/wiki/Progesterone" title="Progesterone">progesterone</a>.<a href="#cite_note-pmid16112947-11">[11]</a> In contrast, its parent compounds, <a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">testosterone</a>, <a href="/wiki/Nandrolone" title="Nandrolone">nandrolone</a> (19-nortestosterone), and <a href="/wiki/Ethisterone" title="Ethisterone">ethisterone</a> (17α-ethynyltestosterone), have 2%, 22%, and 44% of the relative binding affinity of progesterone for the PR.<a href="#cite_note-Kuhl2011-64">[57]</a> Unlike norethisterone, its major active metabolite <a href="/wiki/5%CE%B1-dihydronorethisterone" class="mw-redirect" title="5α-dihydronorethisterone">5α-dihydronorethisterone</a> (5α-DHNET), which is formed by transformation via <a href="/wiki/5%CE%B1-reductase" class="mw-redirect" title="5α-reductase">5α-reductase</a>, has been found to possess both progestogenic and marked <a href="/wiki/Antiprogestogen" title="Antiprogestogen">antiprogestogenic</a> activity,<a href="#cite_note-pmid2934946-65">[58]</a> although its affinity for the PR is greatly reduced relative to norethisterone at only 25% of that of progesterone.<a href="#cite_note-pmid16112947-11">[11]</a> Norethisterone produces similar changes in the <a href="/wiki/Endometrium" title="Endometrium">endometrium</a> and <a href="/wiki/Vagina" title="Vagina">vagina</a>, such as <a href="/wiki/Decidualization" title="Decidualization">endometrial transformation</a>, and is similarly <a href="/wiki/Antigonadotropic" class="mw-redirect" title="Antigonadotropic">antigonadotropic</a>, <a href="/wiki/Ovulation" title="Ovulation">ovulation</a>-inhibiting, and <a href="/wiki/Thermogenesis" title="Thermogenesis">thermogenic</a> in women compared to progesterone, which is in accordance with its progestogenic activity.<a href="#cite_note-McCuistionKee2014-66">[59]</a><a href="#cite_note-Kuhl2011-64">[57]</a><a href="#cite_note-pmid13332050-67">[60]</a> <div class="mw-heading mw-heading4"><h4 id="Androgenic_activity">Androgenic activity</h4>[<a href="/w/index.php?title=Norethisterone&action=edit&section=11" title="Edit section: Androgenic activity">edit</a>]</div> Norethisterone has approximately 15% of the affinity of the <a href="/wiki/Anabolic%E2%80%93androgenic_steroid" class="mw-redirect" title="Anabolic–androgenic steroid">anabolic–androgenic steroid</a> (AAS) <a href="/wiki/Metribolone" title="Metribolone">metribolone</a> (R-1881) for the AR, and in accordance, is weakly androgenic.<a href="#cite_note-pmid16112947-11">[11]</a> In contrast to norethisterone, 5α-DHNET, the major metabolite of norethisterone, shows higher affinity for the AR, with approximately 27% of the affinity of metribolone.<a href="#cite_note-pmid16112947-11">[11]</a> However, although 5α-DHNET has higher affinity for the AR than norethisterone, it has significantly diminished and in fact almost abolished androgenic potency in comparison to norethisterone in rodent <a href="/wiki/Bioassay" title="Bioassay">bioassays</a>.<a href="#cite_note-pmid19028512-68">[61]</a><a href="#cite_note-pmid9182866-69">[62]</a> Similar findings were observed for <a href="/wiki/Ethisterone" title="Ethisterone">ethisterone</a> (17α-ethynyltestosterone) and its 5α-reduced metabolite, whereas 5α-reduction enhanced both the AR affinity and androgenic potency of <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> and <a href="/wiki/Nandrolone" title="Nandrolone">nandrolone</a> (19-nortestosterone) in rodent bioassays.<a href="#cite_note-pmid9182866-69">[62]</a> As such, it appears that the ethynyl group of norethisterone at the C17α position is responsible for its loss of androgenicity upon 5α-reduction.<a href="#cite_note-pmid9182866-69">[62]</a> Norethisterone (0.5 to 3 mg/day) has been found to dose-dependently decrease circulating SHBG levels, which is a common property of androgens and is due to AR-mediated suppression of hepatic SHBG production.<a href="#cite_note-pmid9494772-54">[47]</a> The drug also has estrogenic activity, and estrogens are known to increase SHBG hepatic production and circulating levels, so it would appear that the androgenic activity of norethisterone overpowers its estrogenic activity in this regard.<a href="#cite_note-pmid9494772-54">[47]</a> Norethisterone is bound to a considerable extent (36%) to SHBG in circulation.<a href="#cite_note-pmid16112947-11">[11]</a> Although it has lower affinity for SHBG than endogenous androgens and estrogens,<a href="#cite_note-FilshieGuillebaud2013-70">[63]</a> Norethisterone may displace testosterone from SHBG and thereby increase free testosterone levels, and this action may contribute to its weak androgenic effects.<a href="#cite_note-Azziz2007-71">[64]</a> <div class="mw-heading mw-heading4"><h4 id="Estrogenic_activity">Estrogenic activity</h4>[<a href="/w/index.php?title=Norethisterone&action=edit&section=12" title="Edit section: Estrogenic activity">edit</a>]</div> <figure class="mw-halign-right skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Ethinylestradiol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Ethinylestradiol.svg/225px-Ethinylestradiol.svg.png" decoding="async" width="225" height="155" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Ethinylestradiol.svg/338px-Ethinylestradiol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Ethinylestradiol.svg/450px-Ethinylestradiol.svg.png 2x" data-file-width="512" data-file-height="353" /></a><figcaption><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a> (EE), the <a href="/wiki/Metabolite" title="Metabolite">metabolite</a> of norethisterone responsible for its <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogenic</a> activity.<a href="#cite_note-pmid16112947-11">[11]</a></figcaption></figure> Norethisterone binds to the ERs, the <a href="/wiki/ER%CE%B1" class="mw-redirect" title="ERα">ERα</a> and the <a href="/wiki/ER%CE%B2" class="mw-redirect" title="ERβ">ERβ</a>, with 0.07% and 0.01% of the <a href="/wiki/Relative_binding_affinity" class="mw-redirect" title="Relative binding affinity">relative binding affinity</a> of <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a>.<a href="#cite_note-pmid9048584-72">[65]</a> Due to these very low relative affinities, it is essentially inactive itself as a <a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">ligand</a> of the ERs at clinical concentrations.<a href="#cite_note-pmid16112947-11">[11]</a> However, norethisterone has been found to be a <a href="/wiki/Substrate_(biochemistry)" class="mw-redirect" title="Substrate (biochemistry)">substrate</a> for <a href="/wiki/Aromatase" title="Aromatase">aromatase</a> and is converted in the <a href="/wiki/Liver" title="Liver">liver</a> to a small extent (0.35%) to the highly <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potent</a> estrogen <a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">ethinylestradiol</a> (EE), and for this reason, unlike most other progestins, norethisterone has some estrogenic activity.<a href="#cite_note-pmid16112947-11">[11]</a> However, with typical dosages of norethisterone used in <a href="/wiki/Oral_contraceptive" class="mw-redirect" title="Oral contraceptive">oral contraceptives</a> (0.5 to 1 mg), the levels of EE produced are low, and it has been said that they are probably without clinical relevance.<a href="#cite_note-pmid16112947-11">[11]</a> Conversely, doses of 5 and 10 mg of norethisterone, which are used in the treatment of <a href="/wiki/Gynecological_disorder" class="mw-redirect" title="Gynecological disorder">gynecological disorders</a>, are converted at rates of 0.7% and 1.0% and produce levels of EE that correspond to those produced by 30 and 60 μg dosages of EE, respectively.<a href="#cite_note-pmid12215716-9">[9]</a><a href="#cite_note-pmid16112947-11">[11]</a> The levels of EE formed by 0.5 and 1 mg of norethisterone have been estimated based on higher dosages as corresponding to 2 and 10 μg dosages of EE, respectively.<a href="#cite_note-pmid12215716-9">[9]</a> At high doses, norethisterone may increase the risk of <a href="/wiki/Venous_thromboembolism" class="mw-redirect" title="Venous thromboembolism">venous thromboembolism</a> due to metabolism into EE.<a href="#cite_note-WiegratzKuhl2006-73">[66]</a> <div class="mw-heading mw-heading4"><h4 id="Neurosteroid_activity">Neurosteroid activity</h4>[<a href="/w/index.php?title=Norethisterone&action=edit&section=13" title="Edit section: Neurosteroid activity">edit</a>]</div> Like <a href="/wiki/Progesterone" title="Progesterone">progesterone</a> and <a href="/wiki/Testosterone" title="Testosterone">testosterone</a>, norethisterone is metabolized into 3,5-tetrahydro <a href="/wiki/Metabolite" title="Metabolite">metabolites</a>.<a href="#cite_note-GiattiMelcangi2016-74">[67]</a> Whether these metabolites of norethisterone interact with the <a href="/wiki/GABAA_receptor" title="GABAA receptor">GABAA receptor</a> similarly to the 3,5-tetrahydro metabolites of progesterone and testosterone like <a href="/wiki/Allopregnanolone" title="Allopregnanolone">allopregnanolone</a> and <a href="/wiki/3%CE%B1-androstanediol" class="mw-redirect" title="3α-androstanediol">3α-androstanediol</a>, respectively, is a topic that does not appear to have been studied and hence requires clarification.<a href="#cite_note-GiattiMelcangi2016-74">[67]</a> <div class="mw-heading mw-heading4"><h4 id="Steroidogenesis_inhibition">Steroidogenesis inhibition</h4>[<a href="/w/index.php?title=Norethisterone&action=edit&section=14" title="Edit section: Steroidogenesis inhibition">edit</a>]</div> Norethisterone is a substrate for and is known to be an <a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibitor</a> of <a href="/wiki/5%CE%B1-reductase" class="mw-redirect" title="5α-reductase">5α-reductase</a>, with 4.4% and 20.1% inhibition at 0.1 and 1 μM, respectively.<a href="#cite_note-pmid16112947-11">[11]</a> However, therapeutic concentrations of norethisterone are in the low <a href="/wiki/Nanomolar" class="mw-redirect" title="Nanomolar">nanomolar</a> range, so this action may not be clinically relevant at typical dosages.<a href="#cite_note-pmid16112947-11">[11]</a> Norethisterone and its major active metabolite 5α-DHNET have been found to act as <a href="/wiki/Irreversible_inhibition" class="mw-redirect" title="Irreversible inhibition">irreversible</a> <a href="/wiki/Aromatase_inhibitor" title="Aromatase inhibitor">aromatase inhibitors</a> (Ki = 1.7 μM and 9.0 μM, respectively).<a href="#cite_note-pmid8205267-75">[68]</a> However, like the case of 5α-reductase, the concentrations required are probably too high to be clinically relevant at typical dosages.<a href="#cite_note-pmid16112947-11">[11]</a> 5α-DHNET specifically has been assessed and found to be selective in its inhibition of aromatase, and does not affect <a href="/wiki/Cholesterol_side-chain_cleavage_enzyme" title="Cholesterol side-chain cleavage enzyme">cholesterol side-chain cleavage enzyme</a> (P450scc), <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/21-hydroxylase" class="mw-redirect" title="21-hydroxylase">21-hydroxylase</a>, or <a href="/wiki/Steroid_11%CE%B2-hydroxylase" title="Steroid 11β-hydroxylase">11β-hydroxylase</a>.<a href="#cite_note-pmid8205267-75">[68]</a> Since it is not aromatized (and hence cannot be transformed into an estrogenic metabolite), unlike norethisterone, 5α-DHNET has been proposed as a potential therapeutic agent in the treatment of ER-positive <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a>.<a href="#cite_note-pmid8205267-75">[68]</a> <div class="mw-heading mw-heading4"><h4 id="Other_activities">Other activities</h4>[<a href="/w/index.php?title=Norethisterone&action=edit&section=15" title="Edit section: Other activities">edit</a>]</div> Norethisterone is a very weak inhibitor of <a href="/wiki/CYP2C9" title="CYP2C9">CYP2C9</a> and <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a> (<a href="/wiki/IC50" title="IC50">IC50</a> = 46 μM and 51 μM, respectively), but these actions require very high concentrations of norethisterone that are far above therapeutic circulating levels (which are in the nanomolar range) and hence are probably not clinically relevant.<a href="#cite_note-pmid16112947-11">[11]</a> Norethisterone and some of its 5α-reduced metabolites have been found to produce <a href="/wiki/Vasodilator" class="mw-redirect" title="Vasodilator">vasodilating</a> effects in animals that are independent of <a href="/wiki/Sex_steroid_receptor" class="mw-redirect" title="Sex steroid receptor">sex steroid receptors</a> and hence appear to be non-genomic in mechanism.<a href="#cite_note-pmid12954372-76">[69]</a> Norethisterone stimulates the <a href="/wiki/Cell_proliferation" title="Cell proliferation">proliferation</a> of <a href="/wiki/MCF-7" title="MCF-7">MCF-7</a> <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a> <a href="/wiki/Cell_(biology)" title="Cell (biology)">cells</a> <a href="/wiki/In_vitro" title="In vitro">in vitro</a>, an action that is independent of the classical PRs and is instead mediated via the <a href="/wiki/Progesterone_receptor_membrane_component-1" class="mw-redirect" title="Progesterone receptor membrane component-1">progesterone receptor membrane component-1</a> (PGRMC1).<a href="#cite_note-pmid23758160-77">[70]</a> Certain other progestins act similarly in this assay, whereas <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a> acts neutrally.<a href="#cite_note-pmid23758160-77">[70]</a> It is unclear if these findings may explain the different risks of breast cancer observed with progesterone and progestins in <a href="/wiki/Clinical_trial" title="Clinical trial">clinical studies</a>.<a href="#cite_note-pmid31512725-78">[71]</a> <div class="mw-heading mw-heading4"><h4 id="Antigonadotropic_effects">Antigonadotropic effects</h4>[<a href="/w/index.php?title=Norethisterone&action=edit&section=16" title="Edit section: Antigonadotropic effects">edit</a>]</div> Due to its progestogenic activity, norethisterone suppresses the <a href="/wiki/Hypothalamic%E2%80%93pituitary%E2%80%93gonadal_axis" title="Hypothalamic–pituitary–gonadal axis">hypothalamic–pituitary–gonadal axis</a> (HPG axis) and hence has <a href="/wiki/Antigonadotropic" class="mw-redirect" title="Antigonadotropic">antigonadotropic</a> effects.<a href="#cite_note-pmid16112947-11">[11]</a><a href="#cite_note-Kuhl2011-64">[57]</a> The estrogenic activity of norethisterone at high doses would also be expected to contribute to its antigonadotropic effects.<a href="#cite_note-pmid12466187-79">[72]</a> Due to its antigonadotropic effects, norethisterone suppresses <a href="/wiki/Gonad" title="Gonad">gonadal</a> <a href="/wiki/Sex_hormone" title="Sex hormone">sex hormone</a> <a href="/wiki/Biosynthesis" title="Biosynthesis">production</a>, inhibits <a href="/wiki/Ovulation" title="Ovulation">ovulation</a> in women, and suppresses <a href="/wiki/Spermatogenesis" title="Spermatogenesis">spermatogenesis</a> in men.<a href="#cite_note-pmid16112947-11">[11]</a><a href="#cite_note-Kuhl2011-64">[57]</a><a href="#cite_note-KamischkeNieschlag2004-80">[73]</a> The <a href="/wiki/Ovulation" title="Ovulation">ovulation</a>-inhibiting dosage of both oral norethisterone and oral norethisterone acetate is about 0.5 mg/day in women.<a href="#cite_note-pmid16112947-11">[11]</a><a href="#cite_note-Rudel1968-81">[74]</a><a href="#cite_note-pmid14667980-82">[75]</a> However, some conflicting data exist, suggesting that higher doses might be necessary for full inhibition of ovulation.<a href="#cite_note-pmid22078182-83">[76]</a> An intramuscular injection of 200 mg norethisterone enanthate has been found to prevent ovulation and suppress levels of <a href="/wiki/Estradiol" title="Estradiol">estradiol</a>, <a href="/wiki/Progesterone" title="Progesterone">progesterone</a>, <a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone">luteinizing hormone</a> (LH), and <a href="/wiki/Follicle-stimulating_hormone" title="Follicle-stimulating hormone">follicle-stimulating hormone</a> (FSH) in women.<a href="#cite_note-Shoupe1993-84">[77]</a><a href="#cite_note-pmid1122756-85">[78]</a><a href="#cite_note-pmid606499-86">[79]</a><a href="#cite_note-pmid572279-87">[80]</a> Early studies of oral norethisterone in men employing doses of 20 to 50 mg/day observed suppression of <a href="/wiki/17-ketosteroid" class="mw-redirect" title="17-ketosteroid">17-ketosteroid</a> <a href="/wiki/Excretion" title="Excretion">excretion</a>, increased <a href="/wiki/Estrogen" title="Estrogen">estrogen</a> excretion (due to conversion into <a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">ethinylestradiol</a>), suppression of spermatogenesis, <a href="/wiki/Libido" title="Libido">libido</a>, and <a href="/wiki/Erectile_function" class="mw-redirect" title="Erectile function">erectile function</a>, and incidence of <a href="/wiki/Gynecomastia" title="Gynecomastia">gynecomastia</a>.<a href="#cite_note-pmid793446-88">[81]</a><a href="#cite_note-pmid13583821-89">[82]</a><a href="#cite_note-pmid14400846-90">[83]</a><a href="#cite_note-pmid13942007-60">[53]</a><a href="#cite_note-pmid14261416-91">[84]</a> A dosage of oral norethisterone of 25 mg/day for 3 weeks in men has been reported to suppress testosterone levels by about 70%, to 100 to 200 ng/dL, within 4 or 5 days, as well as to suppress <a href="/wiki/Sperm_count" class="mw-redirect" title="Sperm count">sperm count</a> and to have no effect on libido or erectile function over this short time period.<a href="#cite_note-MougdalSuresh1995-92">[85]</a><a href="#cite_note-JohonssonNygren1973-93">[86]</a> In healthy young men, norethisterone acetate alone at a dose of 5 to 10 mg/day orally for 2 weeks suppressed testosterone levels from ~527 ng/dL to ~231 ng/dL (–56%).<a href="#cite_note-pmid28189123-94">[87]</a> <figure class="mw-halign-right skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Hormone_levels_in_men_with_a_single_intramuscular_injection_of_5_mg_estradiol_valerate_and_50_mg_norethisterone_enanthate_in_oil.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Hormone_levels_in_men_with_a_single_intramuscular_injection_of_5_mg_estradiol_valerate_and_50_mg_norethisterone_enanthate_in_oil.png/500px-Hormone_levels_in_men_with_a_single_intramuscular_injection_of_5_mg_estradiol_valerate_and_50_mg_norethisterone_enanthate_in_oil.png" decoding="async" width="450" height="289" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Hormone_levels_in_men_with_a_single_intramuscular_injection_of_5_mg_estradiol_valerate_and_50_mg_norethisterone_enanthate_in_oil.png/960px-Hormone_levels_in_men_with_a_single_intramuscular_injection_of_5_mg_estradiol_valerate_and_50_mg_norethisterone_enanthate_in_oil.png 1.5x" data-file-width="1894" data-file-height="1218" /></a><figcaption>Hormone levels following a single intramuscular injection of <a href="/wiki/Estradiol_valerate/norethisterone_enanthate" class="mw-redirect" title="Estradiol valerate/norethisterone enanthate">estradiol valerate/norethisterone enanthate</a> (5 mg/50 mg) (Mesigyna) in healthy young men.<a href="#cite_note-ValleAlvarez2011-95">[88]</a> Testosterone levels were maximally suppressed by about 94%, to ~30 ng/dL, when measured at day 7 post-injection.<a href="#cite_note-ValleAlvarez2011-95">[88]</a></figcaption></figure> A single 200 mg intramuscular injection of norethisterone enanthate alone or in combination with 2 mg <a href="/wiki/Estradiol_valerate" title="Estradiol valerate">estradiol valerate</a> has been found to produce a rapid, strong, and sustained decrease in gonadotropin and testosterone levels for up to one month in men.<a href="#cite_note-KamischkeNieschlag2004-80">[73]</a><a href="#cite_note-Amory2003-96">[89]</a><a href="#cite_note-pmid10971453-97">[90]</a> Intramuscular injections of 200 mg norethisterone enanthate once every 3 weeks have also been found to suppress spermatogenesis in men.<a href="#cite_note-pmid793446-88">[81]</a><a href="#cite_note-PetryMauss1970-98">[91]</a> Similarly, a single intramuscular injection of 50 mg norethisterone enanthate in combination with 5 mg estradiol valerate has been found to strongly suppress testosterone levels in men.<a href="#cite_note-ValleAlvarez2011-95">[88]</a> Levels of testosterone decreased from ~503 ng/dL at baseline to ~30 ng/dL at the lowest point (–94%) which occurred at day 7 post-injection.<a href="#cite_note-ValleAlvarez2011-95">[88]</a> <div class="mw-heading mw-heading3"><h3 id="Pharmacokinetics">Pharmacokinetics</h3>[<a href="/w/index.php?title=Norethisterone&action=edit&section=17" title="Edit section: Pharmacokinetics">edit</a>]</div> The <a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">pharmacokinetics</a> of norethisterone have been reviewed.<a href="#cite_note-pmid16112947-11">[11]</a><a href="#cite_note-Springer2013-99">[92]</a> <div class="mw-heading mw-heading4"><h4 id="Absorption">Absorption</h4>[<a href="/w/index.php?title=Norethisterone&action=edit&section=18" title="Edit section: Absorption">edit</a>]</div> The <a href="/wiki/Oral_administration" title="Oral administration">oral</a> <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> of norethisterone is between 47 and 73%, with a mean oral bioavailability of 64%.<a href="#cite_note-pmid12215716-9">[9]</a><a href="#cite_note-pmid8842581-10">[10]</a> <a href="/wiki/Micronization" title="Micronization">Micronization</a> has been found to significantly improve the oral bioavailability of norethisterone by increasing <a href="/wiki/Intestinal" class="mw-redirect" title="Intestinal">intestinal</a> <a href="/wiki/Absorption_(pharmacokinetics)" class="mw-redirect" title="Absorption (pharmacokinetics)">absorption</a> and reducing <a href="/wiki/Intestinal" class="mw-redirect" title="Intestinal">intestinal</a> <a href="/wiki/Metabolism" title="Metabolism">metabolism</a>.<a href="#cite_note-pmid16112947-11">[11]</a><a href="#cite_note-pmid2620531-100">[93]</a> A single 2 mg oral dose of norethisterone has been found to result in peak circulating levels of the drug of 12 ng/mL (40 nmol/L), whereas a single 1 mg oral dose of norethisterone in combination with 2 mg estradiol resulted in peak levels of norethisterone of 8.5 ng/mL (29 nmol/L) one-hour post-administration.<a href="#cite_note-pmid16112947-11">[11]</a> <div class="skin-invert-image"> <style data-mw-deduplicate="TemplateStyles:r1275594942">@media all and (max-width:720px){.mw-parser-output .mod-gallery{width:100%!important}}.mw-parser-output .mod-gallery{display:table}.mw-parser-output .mod-gallery-default{background:transparent;margin-top:4px}.mw-parser-output .mod-gallery-center{margin-left:auto;margin-right:auto}.mw-parser-output .mod-gallery-left{float:left}.mw-parser-output .mod-gallery-right{float:right}.mw-parser-output .mod-gallery-none{float:none}.mw-parser-output .mod-gallery-center .gallery{justify-content:center}.mw-parser-output .mod-gallery-left .gallery{justify-content:left}.mw-parser-output .mod-gallery-right .gallery{justify-content:right}.mw-parser-output .mod-gallery-collapsible{width:100%}.mw-parser-output .mod-gallery .title,.mw-parser-output .mod-gallery .main,.mw-parser-output .mod-gallery .footer{display:table-row}.mw-parser-output .mod-gallery .title>div{display:table-cell;padding:0 4px 4px;text-align:center;font-weight:bold}.mw-parser-output .mod-gallery .main>div{display:table-cell}.mw-parser-output .mod-gallery .gallery.gallery.gallery{line-height:1.35em;display:flex;flex-wrap:wrap;column-gap:4px}.mw-parser-output .mod-gallery .footer>div{display:table-cell;padding:4px;text-align:right;font-size:85%;line-height:1em}.mw-parser-output .mod-gallery .title>div *,.mw-parser-output .mod-gallery .footer>div *{overflow:visible}.mw-parser-output .mod-gallery .gallerybox img{background:none!important}.mw-parser-output .mod-gallery .bordered-images .thumb img{outline:solid var(--background-color-neutral,#eaecf0)1px}.mw-parser-output .mod-gallery .whitebg .thumb{background:var(--background-color-base,#fff)!important}@media screen{html.skin-theme-clientpref-night .mw-parser-output .mod-gallery .bordered-images .thumb img[alt*="\200b \200b \200b "],html.skin-theme-clientpref-night .mw-parser-output .skin-invert-image .mod-gallery .whitebg .thumb.thumb.thumb img{outline:solid #d7d7d7 1px}html.skin-theme-clientpref-night .mw-parser-output .skin-invert-image .mod-gallery .whitebg .thumb.thumb.thumb img{background:none!important}html.skin-theme-clientpref-night .mw-parser-output .mod-gallery .whitebg .thumb img:not([alt*="\200b \200b \200b "]):not([alt*="\200b \200b \200c "]){background:white!important}html.skin-theme-clientpref-night .mw-parser-output .mod-gallery img[alt*="\200b \200b \200b "]{filter:invert(1)hue-rotate(180deg)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .mod-gallery .bordered-images .thumb img[alt*="\200b \200b \200b "],html.skin-theme-clientpref-os .mw-parser-output .skin-invert-image .mod-gallery .whitebg .thumb.thumb.thumb img{outline:solid #d7d7d7 1px}html.skin-theme-clientpref-os .mw-parser-output .skin-invert-image .mod-gallery .whitebg .thumb.thumb.thumb img{background:none!important}html.skin-theme-clientpref-os .mw-parser-output .mod-gallery .whitebg .thumb img:not([alt*="\200b \200b \200b "]):not([alt*="\200b \200b \200c "]){background:white!important}html.skin-theme-clientpref-os .mw-parser-output .mod-gallery img[alt*="\200b \200b \200b "]{filter:invert(1)hue-rotate(180deg)}}</style><div class="mod-gallery mod-gallery-center" style=""font-size:small;""><div class="title"><div>Hormone levels with norethisterone</div></div><div class="main"><div><ul class="gallery mw-gallery-traditional nochecker bordered-images whitebg"> <li class="gallerybox" style="width: 485px"> <div class="thumb" style="width: 480px; height: 330px;"><a href="/wiki/File:Norethisterone_and_ethinylestradiol_levels_after_a_single_oral_dose_of_10_mg_norethisterone_acetate_in_postmenopausal_women.png" class="mw-file-description" title="Norethisterone and ethinylestradiol levels over 24 hours after a single oral dose of 10 mg norethisterone acetate in postmenopausal women.[47]"><img alt="Norethisterone and ethinylestradiol levels over 24 hours after a single oral dose of 10 mg norethisterone acetate in postmenopausal women." src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e5/Norethisterone_and_ethinylestradiol_levels_after_a_single_oral_dose_of_10_mg_norethisterone_acetate_in_postmenopausal_women.png/500px-Norethisterone_and_ethinylestradiol_levels_after_a_single_oral_dose_of_10_mg_norethisterone_acetate_in_postmenopausal_women.png" decoding="async" width="450" height="281" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e5/Norethisterone_and_ethinylestradiol_levels_after_a_single_oral_dose_of_10_mg_norethisterone_acetate_in_postmenopausal_women.png/960px-Norethisterone_and_ethinylestradiol_levels_after_a_single_oral_dose_of_10_mg_norethisterone_acetate_in_postmenopausal_women.png 1.5x" data-file-width="1790" data-file-height="1118" /></a></div> <div class="gallerytext">Norethisterone and ethinylestradiol levels over 24 hours after a single oral dose of 10 mg norethisterone acetate in postmenopausal women.<a href="#cite_note-pmid9494772-54">[47]</a></div> </li> <li class="gallerybox" style="width: 485px"> <div class="thumb" style="width: 480px; height: 330px;"><a href="/wiki/File:Norethisterone_and_ethinylestradiol_levels_after_a_single_intramuscular_injection_of_200_mg_norethisterone_enanthate_in_premenopausal_women.png" class="mw-file-description" title="Norethisterone and ethinylestradiol levels over 8 weeks after a single intramuscular injection of 200 mg norethisterone enanthate in premenopausal women.[94]"><img alt="Norethisterone and ethinylestradiol levels over 8 weeks after a single intramuscular injection of 200 mg norethisterone enanthate in premenopausal women." src="//upload.wikimedia.org/wikipedia/commons/thumb/d/df/Norethisterone_and_ethinylestradiol_levels_after_a_single_intramuscular_injection_of_200_mg_norethisterone_enanthate_in_premenopausal_women.png/500px-Norethisterone_and_ethinylestradiol_levels_after_a_single_intramuscular_injection_of_200_mg_norethisterone_enanthate_in_premenopausal_women.png" decoding="async" width="450" height="281" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/df/Norethisterone_and_ethinylestradiol_levels_after_a_single_intramuscular_injection_of_200_mg_norethisterone_enanthate_in_premenopausal_women.png/960px-Norethisterone_and_ethinylestradiol_levels_after_a_single_intramuscular_injection_of_200_mg_norethisterone_enanthate_in_premenopausal_women.png 1.5x" data-file-width="1798" data-file-height="1124" /></a></div> <div class="gallerytext">Norethisterone and ethinylestradiol levels over 8 weeks after a single intramuscular injection of 200 mg norethisterone enanthate in premenopausal women.<a href="#cite_note-pmid29522253-101">[94]</a></div> </li> </ul></div></div></div></div> <div class="mw-heading mw-heading4"><h4 id="Distribution">Distribution</h4>[<a href="/w/index.php?title=Norethisterone&action=edit&section=19" title="Edit section: Distribution">edit</a>]</div> The <a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">plasma protein binding</a> of norethisterone is 97%.<a href="#cite_note-pmid16112947-11">[11]</a> It is bound 61% bound to <a href="/wiki/Human_serum_albumin" title="Human serum albumin">albumin</a> and 36% bound to SHBG.<a href="#cite_note-pmid16112947-11">[11]</a> <div class="mw-heading mw-heading4"><h4 id="Metabolism">Metabolism</h4>[<a href="/w/index.php?title=Norethisterone&action=edit&section=20" title="Edit section: Metabolism">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: light-dark(aliceblue,var(--background-color-neutral)); color:var(--color-base,light-dark(#202122,#eaecf0)); margin-bottom:3px;"><a href="/wiki/Metabolism" title="Metabolism">Metabolism</a> of norethisterone and its <a href="/wiki/Prodrug" title="Prodrug">prodrugs</a> in humans</div> <div class="skin-invert-image" style="position:relative; width:550px; height:510px; overflow:hidden; border:solid #ccc 1px; background-color:light-dark(white,transparent);"> <div style="left:0px; top:0px; width:550px; position:absolute"> <img alt="Norethisterone structures" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f3/Norethisterone_metabolism.png/550px-Norethisterone_metabolism.png" decoding="async" width="550" height="506" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f3/Norethisterone_metabolism.png/825px-Norethisterone_metabolism.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f3/Norethisterone_metabolism.png/1100px-Norethisterone_metabolism.png 2x" data-file-width="1847" data-file-height="1700" /> </div> <div style="text-align:center; font-size:14px; line-height:110%"> <div style="background-color:transparent; color:var(--color-base,#202122)"></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/20px-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/40px-Interactive_icon.svg.png 1.5x" data-file-width="133" data-file-height="200" /></div>The <a href="/wiki/Metabolic_pathway" title="Metabolic pathway">metabolic pathways</a> involved in the <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> of norethisterone in humans. <a href="/wiki/Norethisterone_acetate" title="Norethisterone acetate">Norethisterone acetate</a>, <a href="/wiki/Norethisterone_enanthate" title="Norethisterone enanthate">norethisterone enanthate</a>, <a href="/wiki/Etynodiol" title="Etynodiol">etynodiol</a>, <a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">etynodiol diacetate</a>, <a href="/wiki/Lynestrenol" title="Lynestrenol">lynestrenol</a>, <a href="/wiki/Noretynodrel" title="Noretynodrel">noretynodrel</a>, <a href="/wiki/Quingestanol" title="Quingestanol">quingestanol</a>, and <a href="/wiki/Quingestanol_acetate" title="Quingestanol acetate">quingestanol acetate</a> are all <a href="/wiki/Prodrug" title="Prodrug">prodrugs</a> of norethisterone. <a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a> is an <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogenic</a> <a href="/wiki/Metabolite" title="Metabolite">metabolite</a> of norethisterone formed by <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> <a href="/wiki/Enzyme" title="Enzyme">enzymes</a>. The two <a href="/wiki/Isomer" title="Isomer">isomers</a> of <a href="/wiki/Dihydronorethisterone" class="mw-redirect" title="Dihydronorethisterone">dihydronorethisterone</a> and the four isomers of tetrahydronorethisterone are formed by <a href="/wiki/5%CE%B1-reductase" class="mw-redirect" title="5α-reductase">5α-</a> and <a href="/wiki/5%CE%B2-reductase" class="mw-redirect" title="5β-reductase">5β-reductases</a> and <a href="/wiki/3%CE%B1-hydroxysteroid_dehydrogenase" class="mw-redirect" title="3α-hydroxysteroid dehydrogenase">3α-</a> and <a href="/wiki/3%CE%B2-hydroxysteroid_dehydrogenase" class="mw-redirect" title="3β-hydroxysteroid dehydrogenase">3β-hydroxysteroid dehydrogenases</a> and have diminished or absent activity. Norethisterone and its metabolites also undergo <a href="/wiki/Hydroxylation" title="Hydroxylation">hydroxylation</a> via cytochrome P450 enzymes and <a href="/wiki/Conjugation_(biochemistry)" class="mw-redirect" title="Conjugation (biochemistry)">conjugation</a> via <a href="/wiki/Glucuronidation" title="Glucuronidation">glucuronidation</a> and <a href="/wiki/Sulfation" title="Sulfation">sulfation</a> at available <a href="/wiki/Hydroxyl_group" class="mw-redirect" title="Hydroxyl group">hydroxyl</a> (–OH) <a href="/wiki/Functional_group" title="Functional group">groups</a>. Sources:<a href="#cite_note-Thijssen1972-102">[95]</a><a href="#cite_note-Okada2010-103">[96]</a><a href="#cite_note-Briggs1980-104">[97]</a><a href="#cite_note-ThomasKeenan1986-105">[98]</a><a href="#cite_note-pmid6342899-106">[99]</a><a href="#cite_note-pmid4206183-107">[100]</a><a href="#cite_note-pmid2170822-15">[15]</a><a href="#cite_note-Kuhl2011-64">[57]</a><a href="#cite_note-pmid16112947-11">[11]</a><a href="#cite_note-pmid17653961-108">[101]</a><a href="#cite_note-StanczykRoy1990-109">[102]</a></div> </div> </div> </td></tr></tbody></table> Norethisterone has an <a href="/wiki/Elimination_half-life" class="mw-redirect" title="Elimination half-life">elimination half-life</a> of 5.2 to 12.8 hours, with a mean elimination half-life of 8.0 hours.<a href="#cite_note-pmid12215716-9">[9]</a> The <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> of norethisterone is very similar to that of testosterone (and nandrolone) and is mainly via reduction of the Δ4 <a href="/wiki/Double_bond" title="Double bond">double bond</a> to 5α- and 5β-dihydronorethisterone, which is followed by the reduction of the C3 <a href="/wiki/Ketone" title="Ketone">keto</a> <a href="/wiki/Functional_group" title="Functional group">group</a> to the four <a href="/wiki/Isomer" title="Isomer">isomers</a> of 3,5-tetrahydronorethisterone.<a href="#cite_note-pmid16112947-11">[11]</a> These <a href="/wiki/Biotransformation" title="Biotransformation">transformations</a> are catalyzed by <a href="/wiki/5%CE%B1-reductase" class="mw-redirect" title="5α-reductase">5α-</a> and <a href="/wiki/5%CE%B2-reductase" class="mw-redirect" title="5β-reductase">5β-reductase</a> and <a href="/wiki/3%CE%B1-hydroxysteroid_dehydrogenase" class="mw-redirect" title="3α-hydroxysteroid dehydrogenase">3α-</a> and <a href="/wiki/3%CE%B2-hydroxysteroid_dehydrogenase" class="mw-redirect" title="3β-hydroxysteroid dehydrogenase">3β-hydroxysteroid dehydrogenase</a> both in the <a href="/wiki/Liver" title="Liver">liver</a> and in extrahepatic tissues such as the <a href="/wiki/Pituitary_gland" title="Pituitary gland">pituitary gland</a>, <a href="/wiki/Uterus" title="Uterus">uterus</a>, <a href="/wiki/Prostate_gland" class="mw-redirect" title="Prostate gland">prostate gland</a>, <a href="/wiki/Vagina" title="Vagina">vagina</a>, and <a href="/wiki/Breast" title="Breast">breast</a>.<a href="#cite_note-pmid11162927-110">[103]</a> With the exception of 3α,5α- and 3β,5α-tetrahydronorethisterone, which have significant affinity for the ER and are estrogenic to some degree, the 3,5-tetrahydro metabolites of norethisterone are inactive in terms of affinity for <a href="/wiki/Sex_steroid_receptor" class="mw-redirect" title="Sex steroid receptor">sex steroid receptors</a> (specifically, the PR, AR, and ER).<a href="#cite_note-pmid3871879-111">[104]</a><a href="#cite_note-pmid3090814-112">[105]</a><a href="#cite_note-pmid19008332-113">[106]</a> A small amount of norethisterone is also converted by <a href="/wiki/Aromatase" title="Aromatase">aromatase</a> into EE.<a href="#cite_note-pmid12215716-9">[9]</a><a href="#cite_note-pmid16112947-11">[11]</a><a href="#cite_note-pmid17341557-61">[54]</a> Norethisterone is metabolized in the liver via <a href="/wiki/Hydroxylation" title="Hydroxylation">hydroxylation</a> as well, mainly by <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a>.<a href="#cite_note-pmid18356043-12">[12]</a> Some <a href="/wiki/Conjugation_(biochemistry)" class="mw-redirect" title="Conjugation (biochemistry)">conjugation</a> (including <a href="/wiki/Glucuronidation" title="Glucuronidation">glucuronidation</a> and <a href="/wiki/Sulfation" title="Sulfation">sulfation</a>)<a href="#cite_note-pmid11162927-110">[103]</a><a href="#cite_note-ScarsiDarin2016-114">[107]</a> of norethisterone and its metabolites occurs in spite of <a href="/wiki/Steric_hindrance" class="mw-redirect" title="Steric hindrance">steric hindrance</a> by the <a href="/wiki/Ethynyl_group" title="Ethynyl group">ethynyl group</a> at C17α.<a href="#cite_note-pmid16112947-11">[11]</a> The ethynyl group of norethisterone is preserved in approximately 90% of all of its metabolites.<a href="#cite_note-pmid16112947-11">[11]</a> Norethisterone is used in birth control pills, opposed to progesterone itself, because it is not metabolized as rapidly as progesterone when consumed orally. When progesterone is consumed orally it is rapidly metabolized in the gastrointestinal tract and the liver, and broken down into many different metabolites. Whereas, norethisterone is not as rapidly metabolized allowing norethisterone to be present in higher quantities allowing it to more effectively compete for progesterone receptor binding sites.<a href="#cite_note-pmid16112947-11">[11]</a> <div class="mw-heading mw-heading4"><h4 id="Elimination">Elimination</h4>[<a href="/w/index.php?title=Norethisterone&action=edit&section=21" title="Edit section: Elimination">edit</a>]</div> Norethisterone is <a href="/wiki/Elimination_(pharmacology)" title="Elimination (pharmacology)">eliminated</a> 33 to 81% in <a href="/wiki/Urine" title="Urine">urine</a> and 35 to 43% in <a href="/wiki/Feces" title="Feces">feces</a>.<a href="#cite_note-DeGroot2001-115">[108]</a> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2>[<a href="/w/index.php?title=Norethisterone&action=edit&section=22" title="Edit section: Chemistry">edit</a>]</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">See also: <a href="/wiki/List_of_progestogens" title="List of progestogens">List of progestogens</a> and <a href="/wiki/List_of_androgens/anabolic_steroids" class="mw-redirect" title="List of androgens/anabolic steroids">List of androgens/anabolic steroids</a></div> Norethisterone, also known as 17α-ethynyl-19-nortestosterone or as 17α-ethynylestra-4-en-17β-ol-3-one, is a <a href="/wiki/Synthetic_compound" class="mw-redirect" title="Synthetic compound">synthetic</a> <a href="/wiki/Estrane" title="Estrane">estrane</a> <a href="/wiki/Steroid" title="Steroid">steroid</a> and a <a href="/wiki/Chemical_derivative" class="mw-redirect" title="Chemical derivative">derivative</a> of <a href="/wiki/Testosterone" title="Testosterone">testosterone</a>.<a href="#cite_note-Elks2014-116">[109]</a><a href="#cite_note-IN2000-117">[110]</a> It is specifically a derivative of testosterone in which an <a href="/wiki/Ethynyl_group" title="Ethynyl group">ethynyl group</a> has been added at the C17α position and the <a href="/wiki/Methyl_group" title="Methyl group">methyl group</a> at the C19 position has been removed; hence, it is a combined derivative of <a href="/wiki/Ethisterone" title="Ethisterone">ethisterone</a> (17α-ethynyltestosterone) and <a href="/wiki/Nandrolone" title="Nandrolone">nandrolone</a> (19-nortestosterone).<a href="#cite_note-Elks2014-116">[109]</a><a href="#cite_note-IN2000-117">[110]</a> These modifications result in increased <a href="/wiki/Progestogen_(medication)" title="Progestogen (medication)">progestogenic</a> activity and <a href="/wiki/Oral_administration" title="Oral administration">oral</a> <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> as well as decreased <a href="/wiki/Androgenic" class="mw-redirect" title="Androgenic">androgenic</a>/<a href="/wiki/Anabolic" class="mw-redirect" title="Anabolic">anabolic</a> activity.<a href="#cite_note-Chwalisz,_K._2012-118">[111]</a> <div class="mw-heading mw-heading3"><h3 id="Derivatives">Derivatives</h3>[<a href="/w/index.php?title=Norethisterone&action=edit&section=23" title="Edit section: Derivatives">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/Progestogen_ester" title="Progestogen ester">Progestogen ester</a> and <a href="/wiki/List_of_progestogen_esters" title="List of progestogen esters">List of progestogen esters</a></div> Norethisterone (NET) is the <a href="/wiki/Parent_compound" class="mw-redirect" title="Parent compound">parent compound</a> of a large group of progestins that includes most of the progestins known as the 19-nortestosterone derivatives.<a href="#cite_note-ShoupeHaseltine2012-119">[112]</a> This group is divided by <a href="/wiki/Chemical_structure" title="Chemical structure">chemical structure</a> into the <a href="/wiki/Estrane" title="Estrane">estranes</a> (derivatives of norethisterone) and the <a href="/wiki/Gonane" title="Gonane">gonanes</a> (18-methylgonanes or 13β-ethylestranes; derivatives of <a href="/wiki/Levonorgestrel" title="Levonorgestrel">levonorgestrel</a>) and includes the following marketed medications:<a href="#cite_note-Ryan1999-120">[113]</a> <style data-mw-deduplicate="TemplateStyles:r1216972533">.mw-parser-output .col-begin{border-collapse:collapse;padding:0;color:inherit;width:100%;border:0;margin:0}.mw-parser-output .col-begin-small{font-size:90%}.mw-parser-output .col-break{vertical-align:top;text-align:left}.mw-parser-output .col-break-2{width:50%}.mw-parser-output .col-break-3{width:33.3%}.mw-parser-output .col-break-4{width:25%}.mw-parser-output .col-break-5{width:20%}@media(max-width:720px){.mw-parser-output .col-begin,.mw-parser-output .col-begin>tbody,.mw-parser-output .col-begin>tbody>tr,.mw-parser-output .col-begin>tbody>tr>td{display:block!important;width:100%!important}.mw-parser-output .col-break{padding-left:0!important}}</style><div> <table class="col-begin" role="presentation"> <tbody><tr> <td class="col-break"> <dl><dt>Estranes</dt></dl> <ul><li><a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">Etynodiol diacetate</a> (3β-hydroxy-NET 3β,17β-diacetate)</li> <li><a href="/wiki/Lynestrenol" title="Lynestrenol">Lynestrenol</a> (3-desoxy-NET)</li> <li><a href="/wiki/Norethisterone_acetate" title="Norethisterone acetate">Norethisterone acetate</a> (NET 17β-acetate)</li> <li><a href="/wiki/Norethisterone_enanthate" title="Norethisterone enanthate">Norethisterone enanthate</a> (17β-enanthate)</li> <li><a href="/wiki/Noretynodrel" title="Noretynodrel">Noretynodrel</a> (δ5(10)-NET)</li> <li><a href="/wiki/Norgestrienone" title="Norgestrienone">Norgestrienone</a> (δ9,11-NET)</li> <li><a href="/wiki/Quingestanol_acetate" title="Quingestanol acetate">Quingestanol acetate</a> (NET 17β-acetate 3-cyclopentyl enol ether)</li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a> (7α-methyl-δ5(10)-NET)</li></ul> </td> <td class="col-break"> <dl><dt>Gonanes</dt></dl> <ul><li><a href="/wiki/Desogestrel" title="Desogestrel">Desogestrel</a> (3-deketo-11-methylene-18-methyl-NET)</li> <li><a href="/wiki/Etonogestrel" title="Etonogestrel">Etonogestrel</a> (11-methylene-18-methyl-NET)</li> <li><a href="/wiki/Gestodene" title="Gestodene">Gestodene</a> (18-methyl-δ15-NET)</li> <li><a href="/wiki/Gestrinone" title="Gestrinone">Gestrinone</a> (18-methyl-δ9,11-NET)</li> <li><a href="/wiki/Levonorgestrel" title="Levonorgestrel">Levonorgestrel</a> (18-methyl-NET)</li> <li><a href="/wiki/Norelgestromin" title="Norelgestromin">Norelgestromin</a> (18-methyl-NET 3-oxime)</li> <li><a href="/wiki/Norgestimate" title="Norgestimate">Norgestimate</a> (18-methyl-NET 3-oxime 17β-acetate)</li> <li><a href="/wiki/Norgestrel" title="Norgestrel">Norgestrel</a> (13-ethyl-NET)</li></ul> </td></tr></tbody></table></div> Several of these act as <a href="/wiki/Prodrug" title="Prodrug">prodrugs</a> of norethisterone, including <a href="/wiki/Norethisterone_acetate" title="Norethisterone acetate">norethisterone acetate</a>, <a href="/wiki/Norethisterone_enanthate" title="Norethisterone enanthate">norethisterone enanthate</a>, <a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">etynodiol diacetate</a>, <a href="/wiki/Lynestrenol" title="Lynestrenol">lynestrenol</a>, and <a href="/wiki/Quingestanol_acetate" title="Quingestanol acetate">quingestanol acetate</a>.<a href="#cite_note-pmid2256526-121">[114]</a><a href="#cite_note-pmid20851224-122">[115]</a><a href="#cite_note-pmid3543501-123">[116]</a> <a href="/wiki/Noretynodrel" title="Noretynodrel">Noretynodrel</a> may also be a prodrug of norethisterone.<a href="#cite_note-pmid16112947-11">[11]</a><a href="#cite_note-pmid12215716-9">[9]</a> Norethisterone acetate is taken by mouth similarly to norethisterone, while norethisterone enanthate is given by <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">injection into muscle</a>.<a href="#cite_note-HumansOrganization2007-18">[18]</a> <div class="mw-heading mw-heading4"><h4 id="Non-17α-ethynylated">Non-17α-ethynylated</h4>[<a href="/w/index.php?title=Norethisterone&action=edit&section=24" title="Edit section: Non-17α-ethynylated">edit</a>]</div> 19-Nortestosterone (19-NT) progestins which are technically not derivatives of norethisterone (as they do not have a C17α <a href="/wiki/Ethynyl_group" title="Ethynyl group">ethynyl group</a>) but are still closely related (with other substitutions at the C17α and/or C16β positions) include the following marketed medications:<a href="#cite_note-Elks2014-116">[109]</a><a href="#cite_note-IN2000-117">[110]</a> <ul><li>The C17α <a href="/wiki/Vinyl_group" title="Vinyl group">vinyl</a> (ethenyl) derivatives <a href="/wiki/Norgesterone" title="Norgesterone">norgesterone</a> (17α-vinyl-δ5(10)-19-NT) and <a href="/wiki/Norvinisterone" title="Norvinisterone">norvinisterone</a> (17α-vinyl-19-NT)</li> <li>The C17α <a href="/wiki/Allyl_group" title="Allyl group">allyl</a> derivatives <a href="/wiki/Allylestrenol" title="Allylestrenol">allylestrenol</a> (3-deketo-17α-allyl-19-NT) and <a href="/wiki/Altrenogest" title="Altrenogest">altrenogest</a> (17α-allyl-δ9,11-19-NT)</li> <li>The C17α <a href="/wiki/Alkyl_group" title="Alkyl group">alkyl</a> derivative <a href="/wiki/Normethandrone" title="Normethandrone">normethandrone</a> (17α-methyl-19-NT)</li> <li>The C17α <a href="/wiki/Cyanomethyl" title="Cyanomethyl">cyanomethyl</a> derivative <a href="/wiki/Dienogest" title="Dienogest">dienogest</a> (17α-cyanomethyl-δ9-19-NT)</li> <li>The C16β ethyl derivative <a href="/wiki/Oxendolone" title="Oxendolone">oxendolone</a> (16β-ethyl-19-NT)</li></ul> Many <a href="/wiki/Anabolic_steroid" title="Anabolic steroid">anabolic steroids</a> of the 19-nortestosterone family, like <a href="/wiki/Norethandrolone" title="Norethandrolone">norethandrolone</a> and <a href="/wiki/Ethylestrenol" title="Ethylestrenol">ethylestrenol</a>, are also potent progestogens, but were never marketed as such. <div class="mw-heading mw-heading3"><h3 id="Synthesis">Synthesis</h3>[<a href="/w/index.php?title=Norethisterone&action=edit&section=25" title="Edit section: Synthesis">edit</a>]</div> <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">Chemical syntheses</a> of norethisterone have been published.<a href="#cite_note-Elks2014-116">[109]</a><a href="#cite_note-Springer2013-99">[92]</a> <div class="mw-heading mw-heading4"><h4 id="Synthesis_1">Synthesis 1</h4>[<a href="/w/index.php?title=Norethisterone&action=edit&section=26" title="Edit section: Synthesis 1">edit</a>]</div> <figure class="mw-halign-right skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Norethisterone_synthesis.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/ca/Norethisterone_synthesis.svg/500px-Norethisterone_synthesis.svg.png" decoding="async" width="450" height="204" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/ca/Norethisterone_synthesis.svg/675px-Norethisterone_synthesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/ca/Norethisterone_synthesis.svg/900px-Norethisterone_synthesis.svg.png 2x" data-file-width="512" data-file-height="232" /></a><figcaption>Norethisterone synthesis #1.<a href="#cite_note-DjerassiMiramontes1954-19">[19]</a><a href="#cite_note-Colton-124">[117]</a></figcaption></figure> Estradiol 3-methyl ether (1, EME) is partially reduced to the 1,5-diene (2) as also occurs for the first step in the synthesis of nandrolone. <a href="/wiki/Oppenauer_oxidation" title="Oppenauer oxidation">Oppenauer oxidation</a> then transforms the C17β hydroxyl group into a ketone functionality (3). This is then reacted with metal <a href="/wiki/Acetylide" title="Acetylide">acetylide</a> into the corresponding C17α <a href="/wiki/Ethynyl" class="mw-redirect" title="Ethynyl">ethynyl</a> compound (4). Hydrolysis of the enol ether under mild conditions leads directly to (5),<a href="#cite_note-Colton-124">[117]</a> which appears to be <a href="/wiki/Noretynodrel" title="Noretynodrel">noretynodrel</a> (although Lednicer states that it is "etynodrel" in his book (which may be a synonym <a href="/wiki/Etynodiol" title="Etynodiol">etynodiol</a>); etynodrel is with a <a href="/wiki/Chlorine" title="Chlorine">chlorine</a> atom attached), an orally active progestin. This is the progestogen component of the first <a href="/wiki/Oral_contraceptive" class="mw-redirect" title="Oral contraceptive">oral contraceptive</a> to be offered for sale (i.e., Enovid). Treatment of the ethynyl enol ether with strong acid leads to norethisterone (6).<a href="#cite_note-DjerassiMiramontes1954-19">[19]</a> In practice, these and all other combined oral contraceptives are mixtures of 1 to 2% EE or <a href="/wiki/Mestranol" title="Mestranol">mestranol</a> and an oral <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestin</a>. It has been speculated that the discovery of the necessity of estrogen in addition to progestin for contraceptive efficacy is due to the presence of a small amount of unreduced EME (1) in early batches of 2. This when subjected to oxidation and <a href="/wiki/Alkynylation" title="Alkynylation">ethynylation</a>, would of course lead to mestranol (3). In any event, the need for the presence of estrogen in the mixture is now well established experimentally. <div class="mw-heading mw-heading4"><h4 id="Synthesis_2">Synthesis 2</h4>[<a href="/w/index.php?title=Norethisterone&action=edit&section=27" title="Edit section: Synthesis 2">edit</a>]</div> <figure class="mw-halign-right skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Norethindrone_synthesis.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Norethindrone_synthesis.svg/450px-Norethindrone_synthesis.svg.png" decoding="async" width="450" height="201" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Norethindrone_synthesis.svg/675px-Norethindrone_synthesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Norethindrone_synthesis.svg/900px-Norethindrone_synthesis.svg.png 2x" data-file-width="512" data-file-height="229" /></a><figcaption>Norethisterone synthesis #2.<a href="#cite_note-125">[118]</a><a href="#cite_note-126">[119]</a><a href="#cite_note-127">[120]</a><a href="#cite_note-US2744122-128">[121]</a><a href="#cite_note-US2774777-129">[122]</a></figcaption></figure> Norethisterone is made from <a href="/wiki/Estr-4-ene-3,17-dione" class="mw-redirect" title="Estr-4-ene-3,17-dione">estr-4-ene-3,17-dione</a> (bolandione), which in turn is synthesized by partial reduction of the aromatic region of the 3-O-methyl ether of <a href="/wiki/Estrone" title="Estrone">estrone</a> with lithium in liquid ammonia, and simultaneously of the keto group at C17α to a hydroxyl group, which is then oxidized back to a keto group by <a href="/wiki/Chromium_trioxide" title="Chromium trioxide">chromium trioxide</a> in <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a>. The conjugated C4-C5 olefin and the carbonyl group at C3 is then transformed to dienol ethyl ether using <a href="/wiki/Ethyl_orthoformate" class="mw-redirect" title="Ethyl orthoformate">ethyl orthoformate</a>. The obtained product is ethynylated by <a href="/wiki/Acetylene" title="Acetylene">acetylene</a> in the presence of <a href="/wiki/Potassium_tert-butoxide" title="Potassium tert-butoxide">potassium tert-butoxide</a>. After <a href="/wiki/Hydrochloride" title="Hydrochloride">hydrochloride</a> hydrolysis of the formed O-potassium derivative, during which the enol ether is also hydrolyzed, and the remaining double bond is shifted, the desired norethisterone is obtained. <div class="mw-heading mw-heading2"><h2 id="History">History</h2>[<a href="/w/index.php?title=Norethisterone&action=edit&section=28" title="Edit section: History">edit</a>]</div> Norethisterone was synthesized for the first time by chemists <a href="/wiki/Luis_E._Miramontes" title="Luis E. Miramontes">Luis Miramontes</a>, <a href="/wiki/Carl_Djerassi" title="Carl Djerassi">Carl Djerassi</a>, and <a href="/wiki/George_Rosenkranz" title="George Rosenkranz">George Rosenkranz</a> at <a href="/wiki/Syntex" title="Syntex">Syntex</a> in <a href="/wiki/Mexico_City" title="Mexico City">Mexico City</a> in 1951.<a href="#cite_note-DjerassiMiramontes1954-19">[19]</a> It was <a href="/wiki/Chemical_derivative" class="mw-redirect" title="Chemical derivative">derived</a> from <a href="/wiki/Ethisterone" title="Ethisterone">ethisterone</a>, and was found to possess about 20-fold greater potency as a progestogen in comparison.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] Norethisterone was the first highly active oral <a href="/wiki/Progestogen_(medication)" title="Progestogen (medication)">progestogen</a> to be synthesized, and was preceded (as a progestogen) by <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a> (1934), ethisterone (1938), <a href="/wiki/19-norprogesterone" class="mw-redirect" title="19-norprogesterone">19-norprogesterone</a> (1944), and <a href="/wiki/17%CE%B1-methylprogesterone" class="mw-redirect" title="17α-methylprogesterone">17α-methylprogesterone</a> (1949) as well as by <a href="/wiki/Nandrolone" title="Nandrolone">nandrolone</a> (1950), whereas <a href="/wiki/Noretynodrel" title="Noretynodrel">noretynodrel</a> (1952) and <a href="/wiki/Norethandrolone" title="Norethandrolone">norethandrolone</a> (1953) followed the synthesis of norethisterone.<a href="#cite_note-Shoupe2007-20">[20]</a><a href="#cite_note-Marks2010-21">[21]</a> The drug was introduced as Norlutin in the United States in 1957.<a href="#cite_note-Publishing2013-22">[22]</a> Norethisterone was subsequently combined with <a href="/wiki/Mestranol" title="Mestranol">mestranol</a> and marketed as Ortho-Novum in the United States in 1963. It was the second progestin, after <a href="/wiki/Noretynodrel" title="Noretynodrel">noretynodrel</a> in 1960, to be used in an <a href="/wiki/Oral_contraceptive" class="mw-redirect" title="Oral contraceptive">oral contraceptive</a>.<a href="#cite_note-Marks2010-21">[21]</a> In 1964, additional contraceptive preparations containing norethisterone in combination with mestranol or EE, such as Norlestrin and Norinyl, were marketed in the United States.<a href="#cite_note-Marks2010-21">[21]</a> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2>[<a href="/w/index.php?title=Norethisterone&action=edit&section=29" 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=Norethisterone&action=edit&section=30" title="Edit section: Generic names">edit</a>]</div> Norethisterone is the <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 and <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 of the drug while norethindrone is its <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="#cite_note-Elks2014-116">[109]</a><a href="#cite_note-IN2000-117">[110]</a> <div class="mw-heading mw-heading3"><h3 id="Brand_names">Brand names</h3>[<a href="/w/index.php?title=Norethisterone&action=edit&section=31" title="Edit section: Brand names">edit</a>]</div> Norethisterone is available in Bangladesh as Menogia (ACI), Normens (Renata) etc. Norethisterone (NET), including as norethisterone acetate and norethisterone enanthate, has been marketed under many brand names throughout the world.<a href="#cite_note-IN2000-117">[110]</a><a href="#cite_note-Drugs.com-28">[28]</a> <div class="mw-heading mw-heading3"><h3 id="Availability">Availability</h3>[<a href="/w/index.php?title=Norethisterone&action=edit&section=32" title="Edit section: Availability">edit</a>]</div> <div class="mw-heading mw-heading4"><h4 id="United_States">United States</h4>[<a href="/w/index.php?title=Norethisterone&action=edit&section=33" title="Edit section: United States">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/List_of_progestogens_available_in_the_United_States" title="List of progestogens available in the United States">List of progestogens available in the United States</a></div> Norethisterone was previously available alone in 5 mg tablets under the brand name Norlutin in the United States, but this formulation has since been discontinued.<a href="#cite_note-Drugs@FDA-42">[35]</a> However, norethisterone acetate remains available alone in 5 mg tablets under the brand name Aygestin in the United States.<a href="#cite_note-Drugs@FDA-42">[35]</a> It is one of the only non-contraceptive progestogen-only drug formulations that remains available in the United States.<a href="#cite_note-Drugs@FDA-42">[35]</a> The others include <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a>, <a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">medroxyprogesterone acetate</a>, <a href="/wiki/Megestrol_acetate" title="Megestrol acetate">megestrol acetate</a>, and <a href="/wiki/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">hydroxyprogesterone caproate</a>, as well as the atypical agent <a href="/wiki/Danazol" title="Danazol">danazol</a>.<a href="#cite_note-Drugs@FDA-42">[35]</a> Both norethisterone and norethisterone acetate are also available in the United States as contraceptives.<a href="#cite_note-Drugs@FDA-42">[35]</a> Norethisterone is available both alone (brand names Camila, Errin, Heather, Micronor, Nor-QD, others) and in combination with EE (Norinyl, Ortho-Novum, others) or mestranol (Norinyl, Ortho-Novum, others), while norethisterone acetate is available only in combination with EE (Norlestrin, others).<a href="#cite_note-Drugs@FDA-42">[35]</a> Norethisterone enanthate is not available in the United States in any form.<a href="#cite_note-Drugs@FDA-42">[35]</a><a href="#cite_note-Bullough2001-130">[123]</a><a href="#cite_note-MoskowitzJennings1996-131">[124]</a> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2>[<a href="/w/index.php?title=Norethisterone&action=edit&section=34" title="Edit section: Research">edit</a>]</div> Norethisterone, as norethisterone acetate and norethisterone enanthate, has been studied for use as a potential <a href="/wiki/Male_contraceptive" title="Male contraceptive">male hormonal contraceptive</a> in combination with <a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">testosterone</a> in men.<a href="#cite_note-pmid20933120-132">[125]</a><a href="#cite_note-NieschlagBehre2012-133">[126]</a> Long-acting norethisterone <a href="/wiki/Microsphere" class="mw-redirect" title="Microsphere">microspheres</a> for <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">intramuscular injection</a> have been studied for potential use in birth control.<a href="#cite_note-pmid6223801-134">[127]</a> <div class="mw-heading mw-heading2"><h2 id="References">References</h2>[<a href="/w/index.php?title=Norethisterone&action=edit&section=35" title="Edit section: References">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626" /><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><a href="#cite_ref-1">^</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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.canada.ca/en/health-canada/services/drugs-health-products/drug-products/drug-product-database/label-safety-assessment-update/product-monograph-brand-safety-updates.html">"Product monograph brand safety updates"</a>. <a href="/wiki/Health_Canada" title="Health Canada">Health Canada</a>. 6 June 2024. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20240329200203/https://www.canada.ca/en/health-canada/services/drugs-health-products/drug-products/drug-product-database/label-safety-assessment-update/product-monograph-brand-safety-updates.html">Archived</a> from the original on 29 March 2024. Retrieved 8 June 2024.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Health+Canada&rft.atitle=Product+monograph+brand+safety+updates&rft.date=2024-06-06&rft_id=https%3A%2F%2Fwww.canada.ca%2Fen%2Fhealth-canada%2Fservices%2Fdrugs-health-products%2Fdrug-products%2Fdrug-product-database%2Flabel-safety-assessment-update%2Fproduct-monograph-brand-safety-updates.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-2"><a href="#cite_ref-2">^</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://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=59985565-af09-21ba-0336-3f6db7711bd1">"Camila- norethindrone tablet"</a>. DailyMed. 1 April 2024. Retrieved 29 September 2024.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=DailyMed&rft.atitle=Camila-+norethindrone+tablet&rft.date=2024-04-01&rft_id=https%3A%2F%2Fdailymed.nlm.nih.gov%2Fdailymed%2FdrugInfo.cfm%3Fsetid%3D59985565-af09-21ba-0336-3f6db7711bd1&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-3"><a href="#cite_ref-3">^</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://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=197d31d3-eec8-49c7-9640-918ff138fea2">"Emzahh- norethindrone tablet"</a>. DailyMed. 10 April 2023. Retrieved 29 September 2024.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=DailyMed&rft.atitle=Emzahh-+norethindrone+tablet&rft.date=2023-04-10&rft_id=https%3A%2F%2Fdailymed.nlm.nih.gov%2Fdailymed%2FdrugInfo.cfm%3Fsetid%3D197d31d3-eec8-49c7-9640-918ff138fea2&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-4"><a href="#cite_ref-4">^</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://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=df29577b-c2f0-bea8-b048-7719972707aa">"Errin- norethindrone tablet"</a>. DailyMed. 1 March 2024. Retrieved 29 September 2024.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=DailyMed&rft.atitle=Errin-+norethindrone+tablet&rft.date=2024-03-01&rft_id=https%3A%2F%2Fdailymed.nlm.nih.gov%2Fdailymed%2FdrugInfo.cfm%3Fsetid%3Ddf29577b-c2f0-bea8-b048-7719972707aa&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-5"><a href="#cite_ref-5">^</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://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=35b5ddb5-1729-4588-b2a2-ead56d78b6f9">"Heather- norethindrone tablet"</a>. DailyMed. 31 August 2021. Retrieved 29 September 2024.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=DailyMed&rft.atitle=Heather-+norethindrone+tablet&rft.date=2021-08-31&rft_id=https%3A%2F%2Fdailymed.nlm.nih.gov%2Fdailymed%2FdrugInfo.cfm%3Fsetid%3D35b5ddb5-1729-4588-b2a2-ead56d78b6f9&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-6"><a href="#cite_ref-6">^</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://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=0b87cef0-610c-469d-92ba-4007f4bc3878">"Incassia- norethindrone tablet"</a>. DailyMed. 14 September 2021. Retrieved 29 September 2024.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=DailyMed&rft.atitle=Incassia-+norethindrone+tablet&rft.date=2021-09-14&rft_id=https%3A%2F%2Fdailymed.nlm.nih.gov%2Fdailymed%2FdrugInfo.cfm%3Fsetid%3D0b87cef0-610c-469d-92ba-4007f4bc3878&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-7"><a href="#cite_ref-7">^</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://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e91e7bdd-2984-4332-9b0b-04322792d7f6">"Jencycla- norethindrone tablet"</a>. DailyMed. 13 December 2023. Retrieved 29 September 2024.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=DailyMed&rft.atitle=Jencycla-+norethindrone+tablet&rft.date=2023-12-13&rft_id=https%3A%2F%2Fdailymed.nlm.nih.gov%2Fdailymed%2FdrugInfo.cfm%3Fsetid%3De91e7bdd-2984-4332-9b0b-04322792d7f6&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-MicronorLabel-8">^ <a href="#cite_ref-MicronorLabel_8-0">a</a> <a href="#cite_ref-MicronorLabel_8-1">b</a> <a href="#cite_ref-MicronorLabel_8-2">c</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://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=6fea0c04-cfbc-4bd2-8a1f-fa3d5ed2a941">"Micronor- norethindrone tablet"</a>. DailyMed. 1 April 2011. Retrieved 29 September 2024.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=DailyMed&rft.atitle=Micronor-+norethindrone+tablet&rft.date=2011-04-01&rft_id=https%3A%2F%2Fdailymed.nlm.nih.gov%2Fdailymed%2FdrugInfo.cfm%3Fsetid%3D6fea0c04-cfbc-4bd2-8a1f-fa3d5ed2a941&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid12215716-9">^ <a href="#cite_ref-pmid12215716_9-0">a</a> <a href="#cite_ref-pmid12215716_9-1">b</a> <a href="#cite_ref-pmid12215716_9-2">c</a> <a href="#cite_ref-pmid12215716_9-3">d</a> <a href="#cite_ref-pmid12215716_9-4">e</a> <a href="#cite_ref-pmid12215716_9-5">f</a> <a href="#cite_ref-pmid12215716_9-6">g</a> <a href="#cite_ref-pmid12215716_9-7">h</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFStanczyk2002" class="citation journal cs1">Stanczyk FZ (September 2002). "Pharmacokinetics and potency of progestins used for hormone replacement therapy and contraception". Reviews in Endocrine & Metabolic Disorders. 3 (3): 211–24. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1023%2FA%3A1020072325818">10.1023/A:1020072325818</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/12215716">12215716</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:27018468">27018468</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Reviews+in+Endocrine+%26+Metabolic+Disorders&rft.atitle=Pharmacokinetics+and+potency+of+progestins+used+for+hormone+replacement+therapy+and+contraception&rft.volume=3&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E211-%3C%2Fspan%3E24&rft.date=2002-09&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A27018468%23id-name%3DS2CID&rft_id=info%3Apmid%2F12215716&rft_id=info%3Adoi%2F10.1023%2FA%3A1020072325818&rft.aulast=Stanczyk&rft.aufirst=FZ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid8842581-10">^ <a href="#cite_ref-pmid8842581_10-0">a</a> <a href="#cite_ref-pmid8842581_10-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFotherby1996" class="citation journal cs1">Fotherby K (August 1996). "Bioavailability of orally administered sex steroids used in oral contraception and hormone replacement therapy". Contraception. 54 (2): 59–69. <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%2F0010-7824%2896%2900136-9">10.1016/0010-7824(96)00136-9</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/8842581">8842581</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Contraception&rft.atitle=Bioavailability+of+orally+administered+sex+steroids+used+in+oral+contraception+and+hormone+replacement+therapy&rft.volume=54&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E59-%3C%2Fspan%3E69&rft.date=1996-08&rft_id=info%3Adoi%2F10.1016%2F0010-7824%2896%2900136-9&rft_id=info%3Apmid%2F8842581&rft.aulast=Fotherby&rft.aufirst=K&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid16112947-11">^ <a href="#cite_ref-pmid16112947_11-0">a</a> <a href="#cite_ref-pmid16112947_11-1">b</a> <a href="#cite_ref-pmid16112947_11-2">c</a> <a href="#cite_ref-pmid16112947_11-3">d</a> <a href="#cite_ref-pmid16112947_11-4">e</a> <a href="#cite_ref-pmid16112947_11-5">f</a> <a href="#cite_ref-pmid16112947_11-6">g</a> <a href="#cite_ref-pmid16112947_11-7">h</a> <a href="#cite_ref-pmid16112947_11-8">i</a> <a href="#cite_ref-pmid16112947_11-9">j</a> <a href="#cite_ref-pmid16112947_11-10">k</a> <a href="#cite_ref-pmid16112947_11-11">l</a> <a href="#cite_ref-pmid16112947_11-12">m</a> <a href="#cite_ref-pmid16112947_11-13">n</a> <a href="#cite_ref-pmid16112947_11-14">o</a> <a href="#cite_ref-pmid16112947_11-15">p</a> <a href="#cite_ref-pmid16112947_11-16">q</a> <a href="#cite_ref-pmid16112947_11-17">r</a> <a href="#cite_ref-pmid16112947_11-18">s</a> <a href="#cite_ref-pmid16112947_11-19">t</a> <a href="#cite_ref-pmid16112947_11-20">u</a> <a href="#cite_ref-pmid16112947_11-21">v</a> <a href="#cite_ref-pmid16112947_11-22">w</a> <a href="#cite_ref-pmid16112947_11-23">x</a> <a href="#cite_ref-pmid16112947_11-24">y</a> <a href="#cite_ref-pmid16112947_11-25">z</a> <a href="#cite_ref-pmid16112947_11-26">aa</a> <a href="#cite_ref-pmid16112947_11-27">ab</a> <a href="#cite_ref-pmid16112947_11-28">ac</a> <a href="#cite_ref-pmid16112947_11-29">ad</a> <a href="#cite_ref-pmid16112947_11-30">ae</a> <a href="#cite_ref-pmid16112947_11-31">af</a> <a href="#cite_ref-pmid16112947_11-32">ag</a> <a href="#cite_ref-pmid16112947_11-33">ah</a> <a href="#cite_ref-pmid16112947_11-34">ai</a> <a href="#cite_ref-pmid16112947_11-35">aj</a> <a href="#cite_ref-pmid16112947_11-36">ak</a> <a href="#cite_ref-pmid16112947_11-37">al</a> <a href="#cite_ref-pmid16112947_11-38">am</a> <a href="#cite_ref-pmid16112947_11-39">an</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKuhl2005" class="citation journal cs1">Kuhl H (August 2005). <a rel="nofollow" class="external text" href="http://hormonebalance.org/images/documents/Kuhl%2005%20%20Pharm%20Estro%20Progest%20Climacteric_1313155660.pdf">"Pharmacology of estrogens and progestogens: influence of different routes of administration"</a> (PDF). Climacteric. 8 (Suppl 1): 3–63. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F13697130500148875">10.1080/13697130500148875</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16112947">16112947</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:24616324">24616324</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20160822055012/http://hormonebalance.org/images/documents/Kuhl%2005%20%20Pharm%20Estro%20Progest%20Climacteric_1313155660.pdf">Archived</a> (PDF) from the original on 22 August 2016. Retrieved 6 September 2018.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Climacteric&rft.atitle=Pharmacology+of+estrogens+and+progestogens%3A+influence+of+different+routes+of+administration&rft.volume=8&rft.issue=Suppl+1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E3-%3C%2Fspan%3E63&rft.date=2005-08&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A24616324%23id-name%3DS2CID&rft_id=info%3Apmid%2F16112947&rft_id=info%3Adoi%2F10.1080%2F13697130500148875&rft.aulast=Kuhl&rft.aufirst=H&rft_id=http%3A%2F%2Fhormonebalance.org%2Fimages%2Fdocuments%2FKuhl%252005%2520%2520Pharm%2520Estro%2520Progest%2520Climacteric_1313155660.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid18356043-12">^ <a href="#cite_ref-pmid18356043_12-0">a</a> <a href="#cite_ref-pmid18356043_12-1">b</a> <a href="#cite_ref-pmid18356043_12-2">c</a> <a href="#cite_ref-pmid18356043_12-3">d</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKorhonenTurpeinenTolonenLaine2008" class="citation journal cs1">Korhonen T, Turpeinen M, Tolonen A, Laine K, Pelkonen O (May 2008). "Identification of the human cytochrome P450 enzymes involved in the in vitro biotransformation of lynestrenol and norethindrone". The Journal of Steroid Biochemistry and Molecular Biology. 110 (1–2): 56–66. <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.jsbmb.2007.09.025">10.1016/j.jsbmb.2007.09.025</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/18356043">18356043</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:10809537">10809537</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+Steroid+Biochemistry+and+Molecular+Biology&rft.atitle=Identification+of+the+human+cytochrome+P450+enzymes+involved+in+the+in+vitro+biotransformation+of+lynestrenol+and+norethindrone&rft.volume=110&rft.issue=%3Cspan+class%3D%22nowrap%22%3E1%E2%80%93%3C%2Fspan%3E2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E56-%3C%2Fspan%3E66&rft.date=2008-05&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A10809537%23id-name%3DS2CID&rft_id=info%3Apmid%2F18356043&rft_id=info%3Adoi%2F10.1016%2Fj.jsbmb.2007.09.025&rft.aulast=Korhonen&rft.aufirst=T&rft.au=Turpeinen%2C+M&rft.au=Tolonen%2C+A&rft.au=Laine%2C+K&rft.au=Pelkonen%2C+O&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid8520623-13">^ <a href="#cite_ref-pmid8520623_13-0">a</a> <a href="#cite_ref-pmid8520623_13-1">b</a> <a href="#cite_ref-pmid8520623_13-2">c</a> <a href="#cite_ref-pmid8520623_13-3">d</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFTaitelKafrissen1995" class="citation journal cs1">Taitel HF, Kafrissen ME (1995). "Norethindrone – a review of therapeutic applications". International Journal of Fertility and Menopausal Studies. 40 (4): 207–23. <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/8520623">8520623</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+Fertility+and+Menopausal+Studies&rft.atitle=Norethindrone+%E2%80%93+a+review+of+therapeutic+applications&rft.volume=40&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E207-%3C%2Fspan%3E23&rft.date=1995&rft_id=info%3Apmid%2F8520623&rft.aulast=Taitel&rft.aufirst=HF&rft.au=Kafrissen%2C+ME&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-AldenLowdermilk2013-14"><a href="#cite_ref-AldenLowdermilk2013_14-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFAldenLowdermilkCashionPerry2013" class="citation book cs1">Alden KR, Lowdermilk DL, Cashion MC, Perry SE (2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=KLzwAwAAQBAJ&pg=PA135">Maternity and Women's Health Care – E-Book</a>. Elsevier Health Sciences. pp. 135–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-323-29368-6" title="Special:BookSources/978-0-323-29368-6"><bdi>978-0-323-29368-6</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230309072958/https://books.google.com/books?id=KLzwAwAAQBAJ&pg=PA135">Archived</a> from the original on 9 March 2023. Retrieved 8 January 2018.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Maternity+and+Women%27s+Health+Care+%E2%80%93+E-Book&rft.pages=135-&rft.pub=Elsevier+Health+Sciences&rft.date=2013&rft.isbn=978-0-323-29368-6&rft.aulast=Alden&rft.aufirst=KR&rft.au=Lowdermilk%2C+DL&rft.au=Cashion%2C+MC&rft.au=Perry%2C+SE&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DKLzwAwAAQBAJ%26pg%3DPA135&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid2170822-15">^ <a href="#cite_ref-pmid2170822_15-0">a</a> <a href="#cite_ref-pmid2170822_15-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKuhl1990" class="citation journal cs1">Kuhl H (September 1990). "Pharmacokinetics of oestrogens and progestogens". Maturitas. 12 (3): 171–97. <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%2F0378-5122%2890%2990003-o">10.1016/0378-5122(90)90003-o</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/2170822">2170822</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Maturitas&rft.atitle=Pharmacokinetics+of+oestrogens+and+progestogens&rft.volume=12&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E171-%3C%2Fspan%3E97&rft.date=1990-09&rft_id=info%3Adoi%2F10.1016%2F0378-5122%2890%2990003-o&rft_id=info%3Apmid%2F2170822&rft.aulast=Kuhl&rft.aufirst=H&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-Aygestin-Label-16"><a href="#cite_ref-Aygestin-Label_16-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/018405s023lbl.pdf">"Aygestin (norethindrone acetate tablets, USP)"</a> (PDF). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170210100747/http://www.accessdata.fda.gov/drugsatfda_docs/label/2007/018405s023lbl.pdf">Archived</a> (PDF) from the original on 10 February 2017. Retrieved 11 July 2024.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Aygestin+%28norethindrone+acetate+tablets%2C+USP%29&rft_id=https%3A%2F%2Fwww.accessdata.fda.gov%2Fdrugsatfda_docs%2Flabel%2F2007%2F018405s023lbl.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid14450719-17">^ <a href="#cite_ref-pmid14450719_17-0">a</a> <a href="#cite_ref-pmid14450719_17-1">b</a> <a href="#cite_ref-pmid14450719_17-2">c</a> <a href="#cite_ref-pmid14450719_17-3">d</a> <a href="#cite_ref-pmid14450719_17-4">e</a> <a href="#cite_ref-pmid14450719_17-5">f</a> <a href="#cite_ref-pmid14450719_17-6">g</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFJacobson1962" class="citation journal cs1">Jacobson BD (October 1962). "Hazards of norethindrone therapy during pregnancy". American Journal of Obstetrics and Gynecology. 84 (7): 962–68. <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%2F0002-9378%2862%2990075-3">10.1016/0002-9378(62)90075-3</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/14450719">14450719</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=American+Journal+of+Obstetrics+and+Gynecology&rft.atitle=Hazards+of+norethindrone+therapy+during+pregnancy&rft.volume=84&rft.issue=7&rft.pages=%3Cspan+class%3D%22nowrap%22%3E962-%3C%2Fspan%3E68&rft.date=1962-10&rft_id=info%3Adoi%2F10.1016%2F0002-9378%2862%2990075-3&rft_id=info%3Apmid%2F14450719&rft.aulast=Jacobson&rft.aufirst=BD&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-HumansOrganization2007-18">^ <a href="#cite_ref-HumansOrganization2007_18-0">a</a> <a href="#cite_ref-HumansOrganization2007_18-1">b</a> <a href="#cite_ref-HumansOrganization2007_18-2">c</a> <a href="#cite_ref-HumansOrganization2007_18-3">d</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFIARC_Working_Group_on_the_Evaluation_of_Carcinogenic_Risks_to_HumansWorld_Health_OrganizationInternational_Agency_for_Research_on_Cancer2007" class="citation book cs1">IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, World Health Organization, International Agency for Research on Cancer (2007). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=aGDU5xibtNgC&pg=PA417">Combined Estrogen-progestogen Contraceptives and Combined Estrogen-progestogen Menopausal Therapy</a>. World Health Organization. pp. 417–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-92-832-1291-1" title="Special:BookSources/978-92-832-1291-1"><bdi>978-92-832-1291-1</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230110231306/https://books.google.com/books?id=aGDU5xibtNgC&pg=PA417">Archived</a> from the original on 10 January 2023. Retrieved 12 October 2016. <q>Norethisterone and its acetate and enanthate esters are progestogens that have weak estrogenic and androgenic properties.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Combined+Estrogen-progestogen+Contraceptives+and+Combined+Estrogen-progestogen+Menopausal+Therapy&rft.pages=417-&rft.pub=World+Health+Organization&rft.date=2007&rft.isbn=978-92-832-1291-1&rft.au=IARC+Working+Group+on+the+Evaluation+of+Carcinogenic+Risks+to+Humans&rft.au=World+Health+Organization&rft.au=International+Agency+for+Research+on+Cancer&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DaGDU5xibtNgC%26pg%3DPA417&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-DjerassiMiramontes1954-19">^ <a href="#cite_ref-DjerassiMiramontes1954_19-0">a</a> <a href="#cite_ref-DjerassiMiramontes1954_19-1">b</a> <a href="#cite_ref-DjerassiMiramontes1954_19-2">c</a> <a href="#cite_ref-DjerassiMiramontes1954_19-3">d</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDjerassiMiramontesRosenkranzSondheimer2006" class="citation journal cs1">Djerassi C, Miramontes L, Rosenkranz G, Sondheimer F, Longo LD (January 2006). "Steroids LIV. Synthesis of 19-nor-17alpha-ethynyltestosterone and 19-nor-17alpha-methyltestosterone. 1954". American Journal of Obstetrics and Gynecology. 194 (1): 289; discussion 290. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja01645a010">10.1021/ja01645a010</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/16389045">16389045</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=American+Journal+of+Obstetrics+and+Gynecology&rft.atitle=Steroids+LIV.+Synthesis+of+19-nor-17alpha-ethynyltestosterone+and+19-nor-17alpha-methyltestosterone.+1954&rft.volume=194&rft.issue=1&rft.pages=289%3B+discussion+290&rft.date=2006-01&rft_id=info%3Adoi%2F10.1021%2Fja01645a010&rft_id=info%3Apmid%2F16389045&rft.aulast=Djerassi&rft.aufirst=C&rft.au=Miramontes%2C+L&rft.au=Rosenkranz%2C+G&rft.au=Sondheimer%2C+F&rft.au=Longo%2C+LD&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-Shoupe2007-20">^ <a href="#cite_ref-Shoupe2007_20-0">a</a> <a href="#cite_ref-Shoupe2007_20-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFShoupe2007" class="citation book cs1">Shoupe D (2007). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=sczb0Tk_2IwC&pg=PA15">The Handbook of Contraception: A Guide for Practical Management</a>. Springer Science & Business Media. pp. 15–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-59745-150-5" title="Special:BookSources/978-1-59745-150-5"><bdi>978-1-59745-150-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Handbook+of+Contraception%3A+A+Guide+for+Practical+Management&rft.pages=15-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2007&rft.isbn=978-1-59745-150-5&rft.aulast=Shoupe&rft.aufirst=D&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dsczb0Tk_2IwC%26pg%3DPA15&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-Marks2010-21">^ <a href="#cite_ref-Marks2010_21-0">a</a> <a href="#cite_ref-Marks2010_21-1">b</a> <a href="#cite_ref-Marks2010_21-2">c</a> <a href="#cite_ref-Marks2010_21-3">d</a> <a href="#cite_ref-Marks2010_21-4">e</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMarks2010" class="citation book cs1">Marks L (2010). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=_i-s4biQs7MC&pg=PA74">Sexual Chemistry: A History of the Contraceptive Pill</a>. Yale University Press. pp. 74, 76. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-300-16791-7" title="Special:BookSources/978-0-300-16791-7"><bdi>978-0-300-16791-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Sexual+Chemistry%3A+A+History+of+the+Contraceptive+Pill&rft.pages=74%2C+76&rft.pub=Yale+University+Press&rft.date=2010&rft.isbn=978-0-300-16791-7&rft.aulast=Marks&rft.aufirst=L&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D_i-s4biQs7MC%26pg%3DPA74&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-Publishing2013-22">^ <a href="#cite_ref-Publishing2013_22-0">a</a> <a href="#cite_ref-Publishing2013_22-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWilliam_Andrew_Publishing2013" class="citation book cs1">William Andrew Publishing (2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA2935-IA46">Pharmaceutical Manufacturing Encyclopedia</a> (3rd ed.). Elsevier. pp. 2935–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-8155-1856-3" title="Special:BookSources/978-0-8155-1856-3"><bdi>978-0-8155-1856-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Pharmaceutical+Manufacturing+Encyclopedia&rft.pages=2935-&rft.edition=3rd&rft.pub=Elsevier&rft.date=2013&rft.isbn=978-0-8155-1856-3&rft.au=William+Andrew+Publishing&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D_J2ti4EkYpkC%26pg%3DPA2935-IA46&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-HatcherM.D.2007-23"><a href="#cite_ref-HatcherM.D.2007_23-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHatcherNelson2007" class="citation book cs1">Hatcher RA, Nelson AL (2007). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=txh0LpjjhkoC&pg=PA195">Contraceptive Technology</a>. Ardent Media. pp. 195–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-59708-001-9" title="Special:BookSources/978-1-59708-001-9"><bdi>978-1-59708-001-9</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230110231241/https://books.google.com/books?id=txh0LpjjhkoC&pg=PA195">Archived</a> from the original on 10 January 2023. Retrieved 8 January 2018.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Contraceptive+Technology&rft.pages=195-&rft.pub=Ardent+Media&rft.date=2007&rft.isbn=978-1-59708-001-9&rft.aulast=Hatcher&rft.aufirst=RA&rft.au=Nelson%2C+AL&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dtxh0LpjjhkoC%26pg%3DPA195&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-Gunasheela2011-24"><a href="#cite_ref-Gunasheela2011_24-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFGunasheela2011" class="citation book cs1">Gunasheela S (2011). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=gZB-h_gqgS8C&pg=PA31">Practical Management of Gynecological Problems</a>. JP Medical Ltd. pp. 31–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-93-5025-240-6" title="Special:BookSources/978-93-5025-240-6"><bdi>978-93-5025-240-6</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230309062931/https://books.google.com/books?id=gZB-h_gqgS8C&pg=PA31">Archived</a> from the original on 9 March 2023. Retrieved 8 January 2018.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Practical+Management+of+Gynecological+Problems&rft.pages=31-&rft.pub=JP+Medical+Ltd&rft.date=2011&rft.isbn=978-93-5025-240-6&rft.aulast=Gunasheela&rft.aufirst=S&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DgZB-h_gqgS8C%26pg%3DPA31&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid24226383-25"><a href="#cite_ref-pmid24226383_25-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFGrimesLopezO'BrienRaymond2013" class="citation journal cs1">Grimes DA, Lopez LM, O'Brien PA, Raymond EG (November 2013). "Progestin-only pills for contraception". The Cochrane Database of Systematic Reviews (11): CD007541. <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.CD007541.pub3">10.1002/14651858.CD007541.pub3</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/24226383">24226383</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=Progestin-only+pills+for+contraception&rft.issue=11&rft.pages=CD007541&rft.date=2013-11&rft_id=info%3Adoi%2F10.1002%2F14651858.CD007541.pub3&rft_id=info%3Apmid%2F24226383&rft.aulast=Grimes&rft.aufirst=DA&rft.au=Lopez%2C+LM&rft.au=O%27Brien%2C+PA&rft.au=Raymond%2C+EG&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid14759612-26"><a href="#cite_ref-pmid14759612_26-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHussain2004" class="citation journal cs1">Hussain SF (February 2004). "Progestogen-only pills and high blood pressure: is there an association? A literature review". Contraception. 69 (2): 89–97. <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.contraception.2003.09.002">10.1016/j.contraception.2003.09.002</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/14759612">14759612</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Contraception&rft.atitle=Progestogen-only+pills+and+high+blood+pressure%3A+is+there+an+association%3F+A+literature+review&rft.volume=69&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E89-%3C%2Fspan%3E97&rft.date=2004-02&rft_id=info%3Adoi%2F10.1016%2Fj.contraception.2003.09.002&rft_id=info%3Apmid%2F14759612&rft.aulast=Hussain&rft.aufirst=SF&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-27"><a href="#cite_ref-27">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.drugs.com/pro/opill.html">"Opill: Package Insert / Prescribing Information"</a>. Drugs.com. Retrieved 30 September 2024.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Drugs.com&rft.atitle=Opill%3A+Package+Insert+%2F+Prescribing+Information&rft_id=https%3A%2F%2Fwww.drugs.com%2Fpro%2Fopill.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-Drugs.com-28">^ <a href="#cite_ref-Drugs.com_28-0">a</a> <a href="#cite_ref-Drugs.com_28-1">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://www.drugs.com/international/norethisterone.html">"Norethisterone"</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20180915084556/https://www.drugs.com/international/norethisterone.html">Archived</a> from the original on 15 September 2018. Retrieved 8 January 2018.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Norethisterone&rft_id=https%3A%2F%2Fwww.drugs.com%2Finternational%2Fnorethisterone.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-Drugs.com-Generic-29"><a href="#cite_ref-Drugs.com-Generic_29-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.drugs.com/availability/generic-aygestin.html">"Generic Aygestin Availability"</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20180824135000/https://www.drugs.com/availability/generic-aygestin.html">Archived</a> from the original on 24 August 2018. Retrieved 8 January 2018.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Generic+Aygestin+Availability&rft_id=https%3A%2F%2Fwww.drugs.com%2Favailability%2Fgeneric-aygestin.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-30"><a href="#cite_ref-30">^</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://clincalc.com/DrugStats/Top300Drugs.aspx">"The Top 300 of 2022"</a>. ClinCalc. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20240830202410/https://clincalc.com/DrugStats/Top300Drugs.aspx">Archived</a> from the original on 30 August 2024. Retrieved 30 August 2024.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=ClinCalc&rft.atitle=The+Top+300+of+2022&rft_id=https%3A%2F%2Fclincalc.com%2FDrugStats%2FTop300Drugs.aspx&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-31"><a href="#cite_ref-31">^</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://clincalc.com/DrugStats/Drugs/Norethindrone">"Norethindrone Drug Usage Statistics, United States, 2013–2022"</a>. ClinCalc. Retrieved 30 August 2024.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=ClinCalc&rft.atitle=Norethindrone+Drug+Usage+Statistics%2C+United+States%2C+2013%E2%80%932022&rft_id=https%3A%2F%2Fclincalc.com%2FDrugStats%2FDrugs%2FNorethindrone&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-WHO23rd-32"><a href="#cite_ref-WHO23rd_32-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWorld_Health_Organization2023" class="citation book cs1"><a href="/wiki/World_Health_Organization" title="World Health Organization">World Health Organization</a> (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list. Geneva: World Health Organization. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<a rel="nofollow" class="external text" href="https://hdl.handle.net/10665%2F371090">10665/371090</a>. WHO/MHP/HPS/EML/2023.02.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+selection+and+use+of+essential+medicines+2023%3A+web+annex+A%3A+World+Health+Organization+model+list+of+essential+medicines%3A+23rd+list&rft.place=Geneva&rft.pub=World+Health+Organization&rft.date=2023&rft_id=info%3Ahdl%2F10665%2F371090&rft.au=World+Health+Organization&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-33"><a href="#cite_ref-33">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKimKuritaBulun2013" class="citation journal cs1">Kim JJ, Kurita T, Bulun SE (February 2013). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3565104">"Progesterone action in endometrial cancer, endometriosis, uterine fibroids, and breast cancer"</a>. Endocrine Reviews. 34 (1): 130–62. <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%2Fer.2012-1043">10.1210/er.2012-1043</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/PMC3565104">3565104</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/23303565">23303565</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Endocrine+Reviews&rft.atitle=Progesterone+action+in+endometrial+cancer%2C+endometriosis%2C+uterine+fibroids%2C+and+breast+cancer&rft.volume=34&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E130-%3C%2Fspan%3E62&rft.date=2013-02&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3565104%23id-name%3DPMC&rft_id=info%3Apmid%2F23303565&rft_id=info%3Adoi%2F10.1210%2Fer.2012-1043&rft.aulast=Kim&rft.aufirst=JJ&rft.au=Kurita%2C+T&rft.au=Bulun%2C+SE&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3565104&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-Drugs.com_-41"><a href="#cite_ref-Drugs.com_41-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.drugs.com/international/norethisterone.html">"Norethisterone"</a>. Drugs.com.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Drugs.com&rft.atitle=Norethisterone&rft_id=https%3A%2F%2Fwww.drugs.com%2Finternational%2Fnorethisterone.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-Drugs@FDA-42">^ <a href="#cite_ref-Drugs@FDA_42-0">a</a> <a href="#cite_ref-Drugs@FDA_42-1">b</a> <a href="#cite_ref-Drugs@FDA_42-2">c</a> <a href="#cite_ref-Drugs@FDA_42-3">d</a> <a href="#cite_ref-Drugs@FDA_42-4">e</a> <a href="#cite_ref-Drugs@FDA_42-5">f</a> <a href="#cite_ref-Drugs@FDA_42-6">g</a> <a href="#cite_ref-Drugs@FDA_42-7">h</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.accessdata.fda.gov/scripts/cder/daf/">"Drugs@FDA: FDA Approved Drug Products"</a>. United States Food and Drug Administration. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20161116164727/http://www.accessdata.fda.gov/scripts/cder/daf/">Archived</a> from the original on 16 November 2016. Retrieved 27 November 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Drugs%40FDA%3A+FDA+Approved+Drug+Products&rft.pub=United+States+Food+and+Drug+Administration&rft_id=http%3A%2F%2Fwww.accessdata.fda.gov%2Fscripts%2Fcder%2Fdaf%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-IndexNominum2000-43"><a href="#cite_ref-IndexNominum2000_43-0">^</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=5GpcTQD_L2oC&pg=PA749">Index Nominum 2000: International Drug Directory</a>. Taylor & Francis. January 2000. pp. 749–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-88763-075-1" title="Special:BookSources/978-3-88763-075-1"><bdi>978-3-88763-075-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Index+Nominum+2000%3A+International+Drug+Directory&rft.pages=749-&rft.pub=Taylor+%26+Francis&rft.date=2000-01&rft.isbn=978-3-88763-075-1&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D5GpcTQD_L2oC%26pg%3DPA749&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-HumansCancer1999-44"><a href="#cite_ref-HumansCancer1999_44-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFIARC_Working_Group_on_the_Evaluation_of_Carcinogenic_Risks_to_HumansInternational_Agency_for_Research_on_Cancer1999" class="citation book cs1">IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, International Agency for Research on Cancer (1 January 1999). <a rel="nofollow" class="external text" href="https://monographs.iarc.fr/wp-content/uploads/2018/06/mono72.pdf">Hormonal Contraception and Post-menopausal Hormonal Therapy</a> (PDF). IARC. p. 65. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-92-832-1272-0" title="Special:BookSources/978-92-832-1272-0"><bdi>978-92-832-1272-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Hormonal+Contraception+and+Post-menopausal+Hormonal+Therapy&rft.pages=65&rft.pub=IARC&rft.date=1999-01-01&rft.isbn=978-92-832-1272-0&rft.au=IARC+Working+Group+on+the+Evaluation+of+Carcinogenic+Risks+to+Humans&rft.au=International+Agency+for+Research+on+Cancer&rft_id=https%3A%2F%2Fmonographs.iarc.fr%2Fwp-content%2Fuploads%2F2018%2F06%2Fmono72.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-Aronson2009-45">^ <a href="#cite_ref-Aronson2009_45-0">a</a> <a href="#cite_ref-Aronson2009_45-1">b</a> <a href="#cite_ref-Aronson2009_45-2">c</a> <a href="#cite_ref-Aronson2009_45-3">d</a> <a href="#cite_ref-Aronson2009_45-4">e</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFAronson2009" class="citation book cs1">Aronson JK (2009). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=BWMeSwVwfTkC&pg=PA217">Meyler's Side Effects of Endocrine and Metabolic Drugs</a>. Elsevier. pp. 217, 253, 275 [217]. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-08-093292-7" title="Special:BookSources/978-0-08-093292-7"><bdi>978-0-08-093292-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Meyler%27s+Side+Effects+of+Endocrine+and+Metabolic+Drugs&rft.pages=217%2C+253%2C+275+217&rft.pub=Elsevier&rft.date=2009&rft.isbn=978-0-08-093292-7&rft.aulast=Aronson&rft.aufirst=JK&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DBWMeSwVwfTkC%26pg%3DPA217&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid9845522-46"><a href="#cite_ref-pmid9845522_46-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHägglundRembergerKlaessonLönnqvist1998" class="citation journal cs1">Hägglund H, Remberger M, Klaesson S, Lönnqvist B, Ljungman P, Ringdén O (December 1998). "Norethisterone treatment, a major risk-factor for veno-occlusive disease in the liver after allogeneic bone marrow transplantation". Blood. 92 (12): 4568–72. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1182%2Fblood.V92.12.4568">10.1182/blood.V92.12.4568</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/9845522">9845522</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Blood&rft.atitle=Norethisterone+treatment%2C+a+major+risk-factor+for+veno-occlusive+disease+in+the+liver+after+allogeneic+bone+marrow+transplantation&rft.volume=92&rft.issue=12&rft.pages=%3Cspan+class%3D%22nowrap%22%3E4568-%3C%2Fspan%3E72&rft.date=1998-12&rft_id=info%3Adoi%2F10.1182%2Fblood.V92.12.4568&rft_id=info%3Apmid%2F9845522&rft.aulast=H%C3%A4gglund&rft.aufirst=H&rft.au=Remberger%2C+M&rft.au=Klaesson%2C+S&rft.au=L%C3%B6nnqvist%2C+B&rft.au=Ljungman%2C+P&rft.au=Ringd%C3%A9n%2C+O&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid15571489-47">^ <a href="#cite_ref-pmid15571489_47-0">a</a> <a href="#cite_ref-pmid15571489_47-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCorniaAnawalt2004" class="citation journal cs1">Cornia PB, Anawalt BD (November 2004). "Male hormonal contraception". Expert Opinion on Emerging Drugs. 9 (2): 335–44. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1517%2F14728214.9.2.335">10.1517/14728214.9.2.335</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/15571489">15571489</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:26886374">26886374</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Expert+Opinion+on+Emerging+Drugs&rft.atitle=Male+hormonal+contraception&rft.volume=9&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E335-%3C%2Fspan%3E44&rft.date=2004-11&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A26886374%23id-name%3DS2CID&rft_id=info%3Apmid%2F15571489&rft_id=info%3Adoi%2F10.1517%2F14728214.9.2.335&rft.aulast=Cornia&rft.aufirst=PB&rft.au=Anawalt%2C+BD&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-CorniaAnawalt2005-48">^ <a href="#cite_ref-CorniaAnawalt2005_48-0">a</a> <a href="#cite_ref-CorniaAnawalt2005_48-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCorniaAnawalt2005" class="citation journal cs1">Cornia PB, Anawalt BD (2005). "Male hormonal contraceptives: a potentially patentable and profitable product". Expert Opinion on Therapeutic Patents. 15 (12): 1727–37. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1517%2F13543776.15.12.1727">10.1517/13543776.15.12.1727</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/1354-3776">1354-3776</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:83941717">83941717</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Expert+Opinion+on+Therapeutic+Patents&rft.atitle=Male+hormonal+contraceptives%3A+a+potentially+patentable+and+profitable+product&rft.volume=15&rft.issue=12&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1727-%3C%2Fspan%3E37&rft.date=2005&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A83941717%23id-name%3DS2CID&rft.issn=1354-3776&rft_id=info%3Adoi%2F10.1517%2F13543776.15.12.1727&rft.aulast=Cornia&rft.aufirst=PB&rft.au=Anawalt%2C+BD&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid11836281-49">^ <a href="#cite_ref-pmid11836281_49-0">a</a> <a href="#cite_ref-pmid11836281_49-1">b</a> <a href="#cite_ref-pmid11836281_49-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKamischkeHeuermannKrügervon_Eckardstein2002" class="citation journal cs1">Kamischke A, Heuermann T, Krüger K, von Eckardstein S, Schellschmidt I, Rübig A, et al. (February 2002). <a rel="nofollow" class="external text" href="https://doi.org/10.1210%2Fjcem.87.2.8218">"An effective hormonal male contraceptive using testosterone undecanoate with oral or injectable norethisterone preparations"</a>. The Journal of Clinical Endocrinology and Metabolism. 87 (2): 530–39. <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.87.2.8218">10.1210/jcem.87.2.8218</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/11836281">11836281</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=An+effective+hormonal+male+contraceptive+using+testosterone+undecanoate+with+oral+or+injectable+norethisterone+preparations&rft.volume=87&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E530-%3C%2Fspan%3E39&rft.date=2002-02&rft_id=info%3Adoi%2F10.1210%2Fjcem.87.2.8218&rft_id=info%3Apmid%2F11836281&rft.aulast=Kamischke&rft.aufirst=A&rft.au=Heuermann%2C+T&rft.au=Kr%C3%BCger%2C+K&rft.au=von+Eckardstein%2C+S&rft.au=Schellschmidt%2C+I&rft.au=R%C3%BCbig%2C+A&rft.au=Nieschlag%2C+E&rft_id=https%3A%2F%2Fdoi.org%2F10.1210%252Fjcem.87.2.8218&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid20159314-50">^ <a href="#cite_ref-pmid20159314_50-0">a</a> <a href="#cite_ref-pmid20159314_50-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFJunkins-Hopkins2010" class="citation journal cs1">Junkins-Hopkins JM (March 2010). "Hormone therapy for acne". Journal of the American Academy of Dermatology. 62 (3): 486–88. <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.jaad.2009.12.002">10.1016/j.jaad.2009.12.002</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/20159314">20159314</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+American+Academy+of+Dermatology&rft.atitle=Hormone+therapy+for+acne&rft.volume=62&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E486-%3C%2Fspan%3E88&rft.date=2010-03&rft_id=info%3Adoi%2F10.1016%2Fj.jaad.2009.12.002&rft_id=info%3Apmid%2F20159314&rft.aulast=Junkins-Hopkins&rft.aufirst=JM&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-CO-51">^ <a href="#cite_ref-CO_51-0">a</a> <a href="#cite_ref-CO_51-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFArowojoluGalloLopezGrimes2012" class="citation journal cs1">Arowojolu AO, Gallo MF, Lopez LM, Grimes DA (July 2012). Arowojolu AO (ed.). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11437354">"Combined oral contraceptive pills for treatment of acne"</a>. The Cochrane Database of Systematic Reviews (7): CD004425. <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.CD004425.pub6">10.1002/14651858.CD004425.pub6</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/PMC11437354">11437354</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/22786490">22786490</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=Combined+oral+contraceptive+pills+for+treatment+of+acne&rft.issue=7&rft.pages=CD004425&rft.date=2012-07&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC11437354%23id-name%3DPMC&rft_id=info%3Apmid%2F22786490&rft_id=info%3Adoi%2F10.1002%2F14651858.CD004425.pub6&rft.aulast=Arowojolu&rft.aufirst=AO&rft.au=Gallo%2C+MF&rft.au=Lopez%2C+LM&rft.au=Grimes%2C+DA&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC11437354&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid15663340-52"><a href="#cite_ref-pmid15663340_52-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFvan_VlotenSigurdsson2004" class="citation journal cs1">van Vloten WA, Sigurdsson V (2004). "Selecting an oral contraceptive agent for the treatment of acne in women". American Journal of Clinical Dermatology. 5 (6): 435–41. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.2165%2F00128071-200405060-00008">10.2165/00128071-200405060-00008</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/15663340">15663340</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:9947402">9947402</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=American+Journal+of+Clinical+Dermatology&rft.atitle=Selecting+an+oral+contraceptive+agent+for+the+treatment+of+acne+in+women&rft.volume=5&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E435-%3C%2Fspan%3E41&rft.date=2004&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A9947402%23id-name%3DS2CID&rft_id=info%3Apmid%2F15663340&rft_id=info%3Adoi%2F10.2165%2F00128071-200405060-00008&rft.aulast=van+Vloten&rft.aufirst=WA&rft.au=Sigurdsson%2C+V&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid5843402-53">^ <a href="#cite_ref-pmid5843402_53-0">a</a> <a href="#cite_ref-pmid5843402_53-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPochiStrauss1965" class="citation journal cs1">Pochi PE, Strauss JS (December 1965). "Lack of androgen effect on human sebaceous glands with low-dosage norethindrone". American Journal of Obstetrics and Gynecology. 93 (7): 1002–04. <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%2F0002-9378%2865%2990162-6">10.1016/0002-9378(65)90162-6</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/5843402">5843402</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=American+Journal+of+Obstetrics+and+Gynecology&rft.atitle=Lack+of+androgen+effect+on+human+sebaceous+glands+with+low-dosage+norethindrone&rft.volume=93&rft.issue=7&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1002-%3C%2Fspan%3E04&rft.date=1965-12&rft_id=info%3Adoi%2F10.1016%2F0002-9378%2865%2990162-6&rft_id=info%3Apmid%2F5843402&rft.aulast=Pochi&rft.aufirst=PE&rft.au=Strauss%2C+JS&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid9494772-54">^ <a href="#cite_ref-pmid9494772_54-0">a</a> <a href="#cite_ref-pmid9494772_54-1">b</a> <a href="#cite_ref-pmid9494772_54-2">c</a> <a href="#cite_ref-pmid9494772_54-3">d</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKuhnzHeunerHümpelSeifert1997" class="citation journal cs1">Kuhnz W, Heuner A, Hümpel M, Seifert W, Michaelis K (December 1997). "In vivo conversion of norethisterone and norethisterone acetate to ethinyl etradiol in postmenopausal women". Contraception. 56 (6): 379–85. <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%2Fs0010-7824%2897%2900174-1">10.1016/s0010-7824(97)00174-1</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/9494772">9494772</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Contraception&rft.atitle=In+vivo+conversion+of+norethisterone+and+norethisterone+acetate+to+ethinyl+etradiol+in+postmenopausal+women&rft.volume=56&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E379-%3C%2Fspan%3E85&rft.date=1997-12&rft_id=info%3Adoi%2F10.1016%2Fs0010-7824%2897%2900174-1&rft_id=info%3Apmid%2F9494772&rft.aulast=Kuhnz&rft.aufirst=W&rft.au=Heuner%2C+A&rft.au=H%C3%BCmpel%2C+M&rft.au=Seifert%2C+W&rft.au=Michaelis%2C+K&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-Curwen1962-55">^ <a href="#cite_ref-Curwen1962_55-0">a</a> <a href="#cite_ref-Curwen1962_55-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCurwen1962" class="citation journal cs1">Curwen S (1962). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1958463">"Virilization with Norethisterone"</a>. BMJ. 1 (5289): 1415. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1136%2Fbmj.1.5289.1415-a">10.1136/bmj.1.5289.1415-a</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/0959-8138">0959-8138</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/PMC1958463">1958463</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=BMJ&rft.atitle=Virilization+with+Norethisterone&rft.volume=1&rft.issue=5289&rft.pages=1415&rft.date=1962&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1958463%23id-name%3DPMC&rft.issn=0959-8138&rft_id=info%3Adoi%2F10.1136%2Fbmj.1.5289.1415-a&rft.aulast=Curwen&rft.aufirst=S&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1958463&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-RoxburghWest1973-56">^ <a href="#cite_ref-RoxburghWest1973_56-0">a</a> <a href="#cite_ref-RoxburghWest1973_56-1">b</a> <a href="#cite_ref-RoxburghWest1973_56-2">c</a> <a href="#cite_ref-RoxburghWest1973_56-3">d</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRoxburghWest1973" class="citation journal cs1">Roxburgh DR, West MJ (August 1973). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20161220104951/http://www.popline.org/node/503602">"The use of norethisterone to suppress menstruation in the intellectually severely retarded woman"</a>. The Medical Journal of Australia. 2 (7): 310–13. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.5694%2Fj.1326-5377.1973.tb128175.x">10.5694/j.1326-5377.1973.tb128175.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/4746398">4746398</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:204094551">204094551</a>. Archived from <a rel="nofollow" class="external text" href="http://www.popline.org/node/503602">the original</a> on 20 December 2016. Retrieved 6 December 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Medical+Journal+of+Australia&rft.atitle=The+use+of+norethisterone+to+suppress+menstruation+in+the+intellectually+severely+retarded+woman&rft.volume=2&rft.issue=7&rft.pages=%3Cspan+class%3D%22nowrap%22%3E310-%3C%2Fspan%3E13&rft.date=1973-08&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A204094551%23id-name%3DS2CID&rft_id=info%3Apmid%2F4746398&rft_id=info%3Adoi%2F10.5694%2Fj.1326-5377.1973.tb128175.x&rft.aulast=Roxburgh&rft.aufirst=DR&rft.au=West%2C+MJ&rft_id=http%3A%2F%2Fwww.popline.org%2Fnode%2F503602&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-RoxburghWest1974-57">^ <a href="#cite_ref-RoxburghWest1974_57-0">a</a> <a href="#cite_ref-RoxburghWest1974_57-1">b</a> <a href="#cite_ref-RoxburghWest1974_57-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRoxburghWest1973" class="citation journal cs1">Roxburgh DR, West MJ (August 1973). "The use of norethisterone to suppress menstruation in the intellectually severely retarded woman". The Medical Journal of Australia. 2 (7): 310–13. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1097%2F00006254-197408000-00021">10.1097/00006254-197408000-00021</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/4746398">4746398</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Medical+Journal+of+Australia&rft.atitle=The+use+of+norethisterone+to+suppress+menstruation+in+the+intellectually+severely+retarded+woman&rft.volume=2&rft.issue=7&rft.pages=%3Cspan+class%3D%22nowrap%22%3E310-%3C%2Fspan%3E13&rft.date=1973-08&rft_id=info%3Adoi%2F10.1097%2F00006254-197408000-00021&rft_id=info%3Apmid%2F4746398&rft.aulast=Roxburgh&rft.aufirst=DR&rft.au=West%2C+MJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid14272499-58"><a href="#cite_ref-pmid14272499_58-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBoard1965" class="citation journal cs1">Board JA (April 1965). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1927985">"Clinical Evaluation of the Oral Contraceptive Use of Norethindrone 5 Mg. Plus Mestranol 0.075 Mg"</a>. Canadian Medical Association Journal. 92 (15): 814–17. <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/PMC1927985">1927985</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/14272499">14272499</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Canadian+Medical+Association+Journal&rft.atitle=Clinical+Evaluation+of+the+Oral+Contraceptive+Use+of+Norethindrone+5+Mg.+Plus+Mestranol+0.075+Mg&rft.volume=92&rft.issue=15&rft.pages=%3Cspan+class%3D%22nowrap%22%3E814-%3C%2Fspan%3E17&rft.date=1965-04&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1927985%23id-name%3DPMC&rft_id=info%3Apmid%2F14272499&rft.aulast=Board&rft.aufirst=JA&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1927985&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid22154396-59"><a href="#cite_ref-pmid22154396_59-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKaserMissmerBerryLaufer2012" class="citation journal cs1">Kaser DJ, Missmer SA, Berry KF, Laufer MR (April 2012). "Use of norethindrone acetate alone for postoperative suppression of endometriosis symptoms". Journal of Pediatric and Adolescent Gynecology. 25 (2): 105–08. <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.jpag.2011.09.013">10.1016/j.jpag.2011.09.013</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/22154396">22154396</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+Pediatric+and+Adolescent+Gynecology&rft.atitle=Use+of+norethindrone+acetate+alone+for+postoperative+suppression+of+endometriosis+symptoms&rft.volume=25&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E105-%3C%2Fspan%3E08&rft.date=2012-04&rft_id=info%3Adoi%2F10.1016%2Fj.jpag.2011.09.013&rft_id=info%3Apmid%2F22154396&rft.aulast=Kaser&rft.aufirst=DJ&rft.au=Missmer%2C+SA&rft.au=Berry%2C+KF&rft.au=Laufer%2C+MR&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid13942007-60">^ <a href="#cite_ref-pmid13942007_60-0">a</a> <a href="#cite_ref-pmid13942007_60-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPaulsenLeachLanmanGoldston1962" class="citation journal cs1">Paulsen CA, Leach RB, Lanman J, Goldston N, Maddock WO, Heller CG (October 1962). "Inherent estrogenicity of norethindrone and norethynodrel: comparison with other synthetic progestins and progesterone". The Journal of Clinical Endocrinology and Metabolism. 22 (10): 1033–39. <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-22-10-1033">10.1210/jcem-22-10-1033</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/13942007">13942007</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=Inherent+estrogenicity+of+norethindrone+and+norethynodrel%3A+comparison+with+other+synthetic+progestins+and+progesterone&rft.volume=22&rft.issue=10&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1033-%3C%2Fspan%3E39&rft.date=1962-10&rft_id=info%3Adoi%2F10.1210%2Fjcem-22-10-1033&rft_id=info%3Apmid%2F13942007&rft.aulast=Paulsen&rft.aufirst=CA&rft.au=Leach%2C+RB&rft.au=Lanman%2C+J&rft.au=Goldston%2C+N&rft.au=Maddock%2C+WO&rft.au=Heller%2C+CG&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid17341557-61">^ <a href="#cite_ref-pmid17341557_61-0">a</a> <a href="#cite_ref-pmid17341557_61-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFChuZhangGentzscheinStanczyk2007" class="citation journal cs1">Chu MC, Zhang X, Gentzschein E, Stanczyk FZ, Lobo RA (June 2007). <a rel="nofollow" class="external text" href="https://doi.org/10.1210%2Fjc.2007-0044">"Formation of ethinyl estradiol in women during treatment with norethindrone acetate"</a>. The Journal of Clinical Endocrinology and Metabolism. 92 (6): 2205–07. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1210%2Fjc.2007-0044">10.1210/jc.2007-0044</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/17341557">17341557</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=Formation+of+ethinyl+estradiol+in+women+during+treatment+with+norethindrone+acetate&rft.volume=92&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E2205-%3C%2Fspan%3E07&rft.date=2007-06&rft_id=info%3Adoi%2F10.1210%2Fjc.2007-0044&rft_id=info%3Apmid%2F17341557&rft.aulast=Chu&rft.aufirst=MC&rft.au=Zhang%2C+X&rft.au=Gentzschein%2C+E&rft.au=Stanczyk%2C+FZ&rft.au=Lobo%2C+RA&rft_id=https%3A%2F%2Fdoi.org%2F10.1210%252Fjc.2007-0044&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-ConnollyBritton2017-62"><a href="#cite_ref-ConnollyBritton2017_62-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFConnollyBritton2017" class="citation book cs1">Connolly A, Britton AG (2017). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=WONsDgAAQBAJ&pg=PA153">Women's Health in Primary Care</a>. Cambridge University Press. pp. 153–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-108-16595-2" title="Special:BookSources/978-1-108-16595-2"><bdi>978-1-108-16595-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Women%27s+Health+in+Primary+Care&rft.pages=153-&rft.pub=Cambridge+University+Press&rft.date=2017&rft.isbn=978-1-108-16595-2&rft.aulast=Connolly&rft.aufirst=A&rft.au=Britton%2C+AG&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DWONsDgAAQBAJ%26pg%3DPA153&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid28712325-63">^ <a href="#cite_ref-pmid28712325_63-0">a</a> <a href="#cite_ref-pmid28712325_63-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFarrisBastianelliRosatoBrosens2017" class="citation journal cs1">Farris M, Bastianelli C, Rosato E, Brosens I, Benagiano G (October 2017). "Pharmacodynamics of combined estrogen-progestin oral contraceptives: 2. effects on hemostasis". Expert Review of Clinical Pharmacology. 10 (10): 1129–44. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F17512433.2017.1356718">10.1080/17512433.2017.1356718</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/28712325">28712325</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:205931204">205931204</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Expert+Review+of+Clinical+Pharmacology&rft.atitle=Pharmacodynamics+of+combined+estrogen-progestin+oral+contraceptives%3A+2.+effects+on+hemostasis&rft.volume=10&rft.issue=10&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1129-%3C%2Fspan%3E44&rft.date=2017-10&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A205931204%23id-name%3DS2CID&rft_id=info%3Apmid%2F28712325&rft_id=info%3Adoi%2F10.1080%2F17512433.2017.1356718&rft.aulast=Farris&rft.aufirst=M&rft.au=Bastianelli%2C+C&rft.au=Rosato%2C+E&rft.au=Brosens%2C+I&rft.au=Benagiano%2C+G&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-Kuhl2011-64">^ <a href="#cite_ref-Kuhl2011_64-0">a</a> <a href="#cite_ref-Kuhl2011_64-1">b</a> <a href="#cite_ref-Kuhl2011_64-2">c</a> <a href="#cite_ref-Kuhl2011_64-3">d</a> <a href="#cite_ref-Kuhl2011_64-4">e</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKuhl2011" class="citation journal cs1">Kuhl H (2011). <a rel="nofollow" class="external text" href="http://www.kup.at/kup/pdf/10168.pdf">"Pharmacology of Progestogens"</a> (PDF). J Reproduktionsmed Endokrinol. 8 (1): 157–77. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20161011060809/http://www.kup.at/kup/pdf/10168.pdf">Archived</a> (PDF) from the original on 11 October 2016. Retrieved 10 October 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J+Reproduktionsmed+Endokrinol&rft.atitle=Pharmacology+of+Progestogens&rft.volume=8&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E157-%3C%2Fspan%3E77&rft.date=2011&rft.aulast=Kuhl&rft.aufirst=H&rft_id=http%3A%2F%2Fwww.kup.at%2Fkup%2Fpdf%2F10168.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid2934946-65"><a href="#cite_ref-pmid2934946_65-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFChuLiZhaoZhou1985" class="citation journal cs1 cs1-prop-foreign-lang-source">Chu YH, Li QA, Zhao ZF, Zhou YP, Cao DC (June 1985). "[Antiprogestational action of 5 alpha-dihydronorethisterone]". Zhongguo Yao Li Xue Bao = Acta Pharmacologica Sinica (in Chinese). 6 (2): 125–29. <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/2934946">2934946</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Zhongguo+Yao+Li+Xue+Bao+%3D+Acta+Pharmacologica+Sinica&rft.atitle=%5BAntiprogestational+action+of+5+alpha-dihydronorethisterone%5D&rft.volume=6&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E125-%3C%2Fspan%3E29&rft.date=1985-06&rft_id=info%3Apmid%2F2934946&rft.aulast=Chu&rft.aufirst=YH&rft.au=Li%2C+QA&rft.au=Zhao%2C+ZF&rft.au=Zhou%2C+YP&rft.au=Cao%2C+DC&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-McCuistionKee2014-66"><a href="#cite_ref-McCuistionKee2014_66-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMcCuistionKeeHayes2014" class="citation book cs1">McCuistion LE, Kee JL, Hayes ER (2014). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=abnwAwAAQBAJ&pg=PA846">Pharmacology: A Patient-Centered Nursing Process Approach</a>. Elsevier Health Sciences. pp. 846–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-323-29348-8" title="Special:BookSources/978-0-323-29348-8"><bdi>978-0-323-29348-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Pharmacology%3A+A+Patient-Centered+Nursing+Process+Approach&rft.pages=846-&rft.pub=Elsevier+Health+Sciences&rft.date=2014&rft.isbn=978-0-323-29348-8&rft.aulast=McCuistion&rft.aufirst=LE&rft.au=Kee%2C+JL&rft.au=Hayes%2C+ER&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DabnwAwAAQBAJ%26pg%3DPA846&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid13332050-67"><a href="#cite_ref-pmid13332050_67-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFGreenblatt1956" class="citation journal cs1">Greenblatt RB (July 1956). "The progestational activity of 17-alpha-ethinyl-19-nortestosterone". The Journal of Clinical Endocrinology and Metabolism. 16 (7): 869–75. <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-16-7-869">10.1210/jcem-16-7-869</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/13332050">13332050</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=The+progestational+activity+of+17-alpha-ethinyl-19-nortestosterone&rft.volume=16&rft.issue=7&rft.pages=%3Cspan+class%3D%22nowrap%22%3E869-%3C%2Fspan%3E75&rft.date=1956-07&rft_id=info%3Adoi%2F10.1210%2Fjcem-16-7-869&rft_id=info%3Apmid%2F13332050&rft.aulast=Greenblatt&rft.aufirst=RB&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid19028512-68"><a href="#cite_ref-pmid19028512_68-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFragkakiAngelisKoupparisTsantili-Kakoulidou2009" class="citation journal cs1">Fragkaki AG, Angelis YS, Koupparis M, Tsantili-Kakoulidou A, Kokotos G, Georgakopoulos C (February 2009). "Structural characteristics of anabolic androgenic steroids contributing to binding to the androgen receptor and to their anabolic and androgenic activities. Applied modifications in the steroidal structure". Steroids. 74 (2): 172–97. <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.2008.10.016">10.1016/j.steroids.2008.10.016</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/19028512">19028512</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:41356223">41356223</a>. <q>Many synthetic steroids with high myotrophic activity exhibit myotrophic–androgenic dissociation, since, due to changes introduced in the structure of ring A, they will probably not be substrates for the 5α-reductases [85]. 5α-Reduction does not always amplify the androgenic potency in spite of high RBA of androgens to the AR. This is the case for norethisterone (Fig. 1, 34), a synthetic 19-nor-17α-ethynyl testosterone derivative, which also undergoes enzyme-mediated 5α-reduction and exerts potent androgenic effects in target organs. 5α-Reduced norethisterone displays a higher AR binding but shows a significantly lower androgenic potency than unchanged norethisterone [102, 103].</q></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=Structural+characteristics+of+anabolic+androgenic+steroids+contributing+to+binding+to+the+androgen+receptor+and+to+their+anabolic+and+androgenic+activities.+Applied+modifications+in+the+steroidal+structure&rft.volume=74&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E172-%3C%2Fspan%3E97&rft.date=2009-02&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A41356223%23id-name%3DS2CID&rft_id=info%3Apmid%2F19028512&rft_id=info%3Adoi%2F10.1016%2Fj.steroids.2008.10.016&rft.aulast=Fragkaki&rft.aufirst=AG&rft.au=Angelis%2C+YS&rft.au=Koupparis%2C+M&rft.au=Tsantili-Kakoulidou%2C+A&rft.au=Kokotos%2C+G&rft.au=Georgakopoulos%2C+C&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid9182866-69">^ <a href="#cite_ref-pmid9182866_69-0">a</a> <a href="#cite_ref-pmid9182866_69-1">b</a> <a href="#cite_ref-pmid9182866_69-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLemusEnríquezGarcíaGrillasca1997" class="citation journal cs1">Lemus AE, Enríquez J, García GA, Grillasca I, Pérez-Palacios G (January 1997). "5alpha-reduction of norethisterone enhances its binding affinity for androgen receptors but diminishes its androgenic potency". The Journal of Steroid Biochemistry and Molecular Biology. 60 (1–2): 121–29. <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%2Fs0960-0760%2896%2900172-0">10.1016/s0960-0760(96)00172-0</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/9182866">9182866</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:33771349">33771349</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+Steroid+Biochemistry+and+Molecular+Biology&rft.atitle=5alpha-reduction+of+norethisterone+enhances+its+binding+affinity+for+androgen+receptors+but+diminishes+its+androgenic+potency&rft.volume=60&rft.issue=%3Cspan+class%3D%22nowrap%22%3E1%E2%80%93%3C%2Fspan%3E2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E121-%3C%2Fspan%3E29&rft.date=1997-01&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A33771349%23id-name%3DS2CID&rft_id=info%3Apmid%2F9182866&rft_id=info%3Adoi%2F10.1016%2Fs0960-0760%2896%2900172-0&rft.aulast=Lemus&rft.aufirst=AE&rft.au=Enr%C3%ADquez%2C+J&rft.au=Garc%C3%ADa%2C+GA&rft.au=Grillasca%2C+I&rft.au=P%C3%A9rez-Palacios%2C+G&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-FilshieGuillebaud2013-70"><a href="#cite_ref-FilshieGuillebaud2013_70-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFilshieGuillebaud2013" class="citation book cs1">Filshie M, Guillebaud J (2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=Ug3-BAAAQBAJ&pg=PA26">Contraception: Science and Practice</a>. Elsevier Science. pp. 26–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4831-6366-6" title="Special:BookSources/978-1-4831-6366-6"><bdi>978-1-4831-6366-6</bdi></a>. <q>Norethisterone binds to SHBG with less affinity than endogenous androgens and oestrogens [...]</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Contraception%3A+Science+and+Practice&rft.pages=26-&rft.pub=Elsevier+Science&rft.date=2013&rft.isbn=978-1-4831-6366-6&rft.aulast=Filshie&rft.aufirst=M&rft.au=Guillebaud%2C+J&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DUg3-BAAAQBAJ%26pg%3DPA26&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-Azziz2007-71"><a href="#cite_ref-Azziz2007_71-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFAzziz2007" class="citation book cs1">Azziz R (2007). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=Ch-BsGAOtucC&pg=PA124">Androgen Excess Disorders in Women</a>. Springer Science & Business Media. pp. 124–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-59745-179-6" title="Special:BookSources/978-1-59745-179-6"><bdi>978-1-59745-179-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Androgen+Excess+Disorders+in+Women&rft.pages=124-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2007&rft.isbn=978-1-59745-179-6&rft.aulast=Azziz&rft.aufirst=R&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DCh-BsGAOtucC%26pg%3DPA124&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid9048584-72"><a href="#cite_ref-pmid9048584_72-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKuiperCarlssonGrandienEnmark1997" class="citation journal cs1">Kuiper GG, Carlsson B, Grandien K, Enmark E, Häggblad J, Nilsson S, et al. (March 1997). <a rel="nofollow" class="external text" href="https://doi.org/10.1210%2Fendo.138.3.4979">"Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta"</a>. Endocrinology. 138 (3): 863–70. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1210%2Fendo.138.3.4979">10.1210/endo.138.3.4979</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/9048584">9048584</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Endocrinology&rft.atitle=Comparison+of+the+ligand+binding+specificity+and+transcript+tissue+distribution+of+estrogen+receptors+alpha+and+beta&rft.volume=138&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E863-%3C%2Fspan%3E70&rft.date=1997-03&rft_id=info%3Adoi%2F10.1210%2Fendo.138.3.4979&rft_id=info%3Apmid%2F9048584&rft.aulast=Kuiper&rft.aufirst=GG&rft.au=Carlsson%2C+B&rft.au=Grandien%2C+K&rft.au=Enmark%2C+E&rft.au=H%C3%A4ggblad%2C+J&rft.au=Nilsson%2C+S&rft.au=Gustafsson%2C+JA&rft_id=https%3A%2F%2Fdoi.org%2F10.1210%252Fendo.138.3.4979&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-WiegratzKuhl2006-73"><a href="#cite_ref-WiegratzKuhl2006_73-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWiegratzKuhl2006" class="citation journal cs1">Wiegratz I, Kuhl H (September 2006). "Metabolic and clinical effects of progestogens". The European Journal of Contraception & Reproductive Health Care. 11 (3): 153–61. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F13625180600772741">10.1080/13625180600772741</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/17056444">17056444</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:27088428">27088428</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+European+Journal+of+Contraception+%26+Reproductive+Health+Care&rft.atitle=Metabolic+and+clinical+effects+of+progestogens&rft.volume=11&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E153-%3C%2Fspan%3E61&rft.date=2006-09&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A27088428%23id-name%3DS2CID&rft_id=info%3Apmid%2F17056444&rft_id=info%3Adoi%2F10.1080%2F13625180600772741&rft.aulast=Wiegratz&rft.aufirst=I&rft.au=Kuhl%2C+H&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-GiattiMelcangi2016-74">^ <a href="#cite_ref-GiattiMelcangi2016_74-0">a</a> <a href="#cite_ref-GiattiMelcangi2016_74-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFGiattiMelcangiPesaresi2016" class="citation journal cs1">Giatti S, Melcangi RC, Pesaresi M (August 2016). <a rel="nofollow" class="external text" href="https://doi.org/10.1530%2FJME-16-0061">"The other side of progestins: effects in the brain"</a>. Journal of Molecular Endocrinology. 57 (2): R109–26. <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%2FJME-16-0061">10.1530/JME-16-0061</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/27339142">27339142</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+Molecular+Endocrinology&rft.atitle=The+other+side+of+progestins%3A+effects+in+the+brain&rft.volume=57&rft.issue=2&rft.pages=R109-26&rft.date=2016-08&rft_id=info%3Adoi%2F10.1530%2FJME-16-0061&rft_id=info%3Apmid%2F27339142&rft.aulast=Giatti&rft.aufirst=S&rft.au=Melcangi%2C+RC&rft.au=Pesaresi%2C+M&rft_id=https%3A%2F%2Fdoi.org%2F10.1530%252FJME-16-0061&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid8205267-75">^ <a href="#cite_ref-pmid8205267_75-0">a</a> <a href="#cite_ref-pmid8205267_75-1">b</a> <a href="#cite_ref-pmid8205267_75-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFYamamotoTamuraKitawakiOsawa1994" class="citation journal cs1">Yamamoto T, Tamura T, Kitawaki J, Osawa Y, Okada H (June 1994). "Suicide inactivation of aromatase in human placenta and uterine leiomyoma by 5 alpha-dihydronorethindrone, a metabolite of norethindrone, and its effect on steroid-producing enzymes". European Journal of Endocrinology. 130 (6): 634–40. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1530%2Feje.0.1300634">10.1530/eje.0.1300634</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/8205267">8205267</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=European+Journal+of+Endocrinology&rft.atitle=Suicide+inactivation+of+aromatase+in+human+placenta+and+uterine+leiomyoma+by+5+alpha-dihydronorethindrone%2C+a+metabolite+of+norethindrone%2C+and+its+effect+on+steroid-producing+enzymes&rft.volume=130&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E634-%3C%2Fspan%3E40&rft.date=1994-06&rft_id=info%3Adoi%2F10.1530%2Feje.0.1300634&rft_id=info%3Apmid%2F8205267&rft.aulast=Yamamoto&rft.aufirst=T&rft.au=Tamura%2C+T&rft.au=Kitawaki%2C+J&rft.au=Osawa%2C+Y&rft.au=Okada%2C+H&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid12954372-76"><a href="#cite_ref-pmid12954372_76-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPerusquíaVillalónNavarreteGarcía2003" class="citation journal cs1">Perusquía M, Villalón CM, Navarrete E, García GA, Pérez-Palacios G, Lemus AE (August 2003). "Vasodilating effect of norethisterone and its 5 alpha metabolites: a novel nongenomic action". European Journal of Pharmacology. 475 (1–3): 161–69. <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%2Fs0014-2999%2803%2902106-x">10.1016/s0014-2999(03)02106-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/12954372">12954372</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=European+Journal+of+Pharmacology&rft.atitle=Vasodilating+effect+of+norethisterone+and+its+5+alpha+metabolites%3A+a+novel+nongenomic+action&rft.volume=475&rft.issue=%3Cspan+class%3D%22nowrap%22%3E1%E2%80%93%3C%2Fspan%3E3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E161-%3C%2Fspan%3E69&rft.date=2003-08&rft_id=info%3Adoi%2F10.1016%2Fs0014-2999%2803%2902106-x&rft_id=info%3Apmid%2F12954372&rft.aulast=Perusqu%C3%ADa&rft.aufirst=M&rft.au=Villal%C3%B3n%2C+CM&rft.au=Navarrete%2C+E&rft.au=Garc%C3%ADa%2C+GA&rft.au=P%C3%A9rez-Palacios%2C+G&rft.au=Lemus%2C+AE&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid23758160-77">^ <a href="#cite_ref-pmid23758160_77-0">a</a> <a href="#cite_ref-pmid23758160_77-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFNeubauerMaZhouYu2013" class="citation journal cs1">Neubauer H, Ma Q, Zhou J, Yu Q, Ruan X, Seeger H, et al. (October 2013). "Possible role of PGRMC1 in breast cancer development". Climacteric. 16 (5): 509–13. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3109%2F13697137.2013.800038">10.3109/13697137.2013.800038</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/23758160">23758160</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:29808177">29808177</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Climacteric&rft.atitle=Possible+role+of+PGRMC1+in+breast+cancer+development&rft.volume=16&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E509-%3C%2Fspan%3E13&rft.date=2013-10&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A29808177%23id-name%3DS2CID&rft_id=info%3Apmid%2F23758160&rft_id=info%3Adoi%2F10.3109%2F13697137.2013.800038&rft.aulast=Neubauer&rft.aufirst=H&rft.au=Ma%2C+Q&rft.au=Zhou%2C+J&rft.au=Yu%2C+Q&rft.au=Ruan%2C+X&rft.au=Seeger%2C+H&rft.au=Fehm%2C+T&rft.au=Mueck%2C+AO&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: overridden setting (<a href="/wiki/Category:CS1_maint:_overridden_setting" title="Category:CS1 maint: overridden setting">link</a>) </li> <li id="cite_note-pmid31512725-78"><a href="#cite_ref-pmid31512725_78-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFTrabertShermanKannanStanczyk2020" class="citation journal cs1">Trabert B, Sherman ME, Kannan N, Stanczyk FZ (April 2020). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7156851">"Progesterone and Breast Cancer"</a>. Endocrine Reviews. 41 (2): 320–44. <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%2Fendrev%2Fbnz001">10.1210/endrev/bnz001</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/PMC7156851">7156851</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/31512725">31512725</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Endocrine+Reviews&rft.atitle=Progesterone+and+Breast+Cancer&rft.volume=41&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E320-%3C%2Fspan%3E44&rft.date=2020-04&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7156851%23id-name%3DPMC&rft_id=info%3Apmid%2F31512725&rft_id=info%3Adoi%2F10.1210%2Fendrev%2Fbnz001&rft.aulast=Trabert&rft.aufirst=B&rft.au=Sherman%2C+ME&rft.au=Kannan%2C+N&rft.au=Stanczyk%2C+FZ&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7156851&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid12466187-79"><a href="#cite_ref-pmid12466187_79-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFAndersonBaird2002" class="citation journal cs1">Anderson RA, Baird DT (December 2002). <a rel="nofollow" class="external text" href="http://www.hormonebalance.org/images/documents/Anderson%2002%20Male%20Contraception%20ER.pdf">"Male contraception"</a> (PDF). Endocrine Reviews. 23 (6): 735–62. <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%2Fer.2002-0002">10.1210/er.2002-0002</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/12466187">12466187</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210828191401/https://www.hormonebalance.org/images/documents/Anderson%2002%20Male%20Contraception%20ER.pdf">Archived</a> (PDF) from the original on 28 August 2021. Retrieved 11 December 2019.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Endocrine+Reviews&rft.atitle=Male+contraception&rft.volume=23&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E735-%3C%2Fspan%3E62&rft.date=2002-12&rft_id=info%3Adoi%2F10.1210%2Fer.2002-0002&rft_id=info%3Apmid%2F12466187&rft.aulast=Anderson&rft.aufirst=RA&rft.au=Baird%2C+DT&rft_id=http%3A%2F%2Fwww.hormonebalance.org%2Fimages%2Fdocuments%2FAnderson%252002%2520Male%2520Contraception%2520ER.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-KamischkeNieschlag2004-80">^ <a href="#cite_ref-KamischkeNieschlag2004_80-0">a</a> <a href="#cite_ref-KamischkeNieschlag2004_80-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKamischkeNieschlag2004" class="citation journal cs1">Kamischke A, Nieschlag E (January 2004). "Progress towards hormonal male contraception". Trends in Pharmacological Sciences. 25 (1): 49–57. <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.tips.2003.11.009">10.1016/j.tips.2003.11.009</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/14723979">14723979</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Trends+in+Pharmacological+Sciences&rft.atitle=Progress+towards+hormonal+male+contraception&rft.volume=25&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E49-%3C%2Fspan%3E57&rft.date=2004-01&rft_id=info%3Adoi%2F10.1016%2Fj.tips.2003.11.009&rft_id=info%3Apmid%2F14723979&rft.aulast=Kamischke&rft.aufirst=A&rft.au=Nieschlag%2C+E&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-Rudel1968-81"><a href="#cite_ref-Rudel1968_81-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRudel1968" class="citation journal cs1">Rudel HW (September 1968). "Pharmacology of oral contraceptives". Clinical Obstetrics and Gynecology. 11 (3): 632–44. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1097%2F00003081-196811030-00002">10.1097/00003081-196811030-00002</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/4878826">4878826</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Clinical+Obstetrics+and+Gynecology&rft.atitle=Pharmacology+of+oral+contraceptives&rft.volume=11&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E632-%3C%2Fspan%3E44&rft.date=1968-09&rft_id=info%3Adoi%2F10.1097%2F00003081-196811030-00002&rft_id=info%3Apmid%2F4878826&rft.aulast=Rudel&rft.aufirst=HW&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid14667980-82"><a href="#cite_ref-pmid14667980_82-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFStanczyk2003" class="citation journal cs1">Stanczyk FZ (November 2003). "All progestins are not created equal". Steroids. 68 (10–13): 879–90. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.steroids.2003.08.003">10.1016/j.steroids.2003.08.003</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/14667980">14667980</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:44601264">44601264</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Steroids&rft.atitle=All+progestins+are+not+created+equal&rft.volume=68&rft.issue=%3Cspan+class%3D%22nowrap%22%3E10%E2%80%93%3C%2Fspan%3E13&rft.pages=%3Cspan+class%3D%22nowrap%22%3E879-%3C%2Fspan%3E90&rft.date=2003-11&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A44601264%23id-name%3DS2CID&rft_id=info%3Apmid%2F14667980&rft_id=info%3Adoi%2F10.1016%2Fj.steroids.2003.08.003&rft.aulast=Stanczyk&rft.aufirst=FZ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid22078182-83"><a href="#cite_ref-pmid22078182_83-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFEndrikatGerlingerRichardRosenbaum2011" class="citation journal cs1">Endrikat J, Gerlinger C, Richard S, Rosenbaum P, Düsterberg B (December 2011). "Ovulation inhibition doses of progestins: a systematic review of the available literature and of marketed preparations worldwide". Contraception. 84 (6): 549–57. <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.contraception.2011.04.009">10.1016/j.contraception.2011.04.009</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/22078182">22078182</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Contraception&rft.atitle=Ovulation+inhibition+doses+of+progestins%3A+a+systematic+review+of+the+available+literature+and+of+marketed+preparations+worldwide&rft.volume=84&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E549-%3C%2Fspan%3E57&rft.date=2011-12&rft_id=info%3Adoi%2F10.1016%2Fj.contraception.2011.04.009&rft_id=info%3Apmid%2F22078182&rft.aulast=Endrikat&rft.aufirst=J&rft.au=Gerlinger%2C+C&rft.au=Richard%2C+S&rft.au=Rosenbaum%2C+P&rft.au=D%C3%BCsterberg%2C+B&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-Shoupe1993-84"><a href="#cite_ref-Shoupe1993_84-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFShoupe1993" class="citation book cs1">Shoupe D (1993). "Injectable Contraceptives and Contraceptive Vaginal Rings". Contraception. Clinical Perspectives in Obstetrics and Gynecology. Springer. pp. 144–57. <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%2F978-1-4612-2730-4_13">10.1007/978-1-4612-2730-4_13</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4612-7645-6" title="Special:BookSources/978-1-4612-7645-6"><bdi>978-1-4612-7645-6</bdi></a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0178-0328">0178-0328</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Injectable+Contraceptives+and+Contraceptive+Vaginal+Rings&rft.btitle=Contraception&rft.series=Clinical+Perspectives+in+Obstetrics+and+Gynecology&rft.pages=%3Cspan+class%3D%22nowrap%22%3E144-%3C%2Fspan%3E57&rft.pub=Springer&rft.date=1993&rft.issn=0178-0328&rft_id=info%3Adoi%2F10.1007%2F978-1-4612-2730-4_13&rft.isbn=978-1-4612-7645-6&rft.aulast=Shoupe&rft.aufirst=D&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid1122756-85"><a href="#cite_ref-pmid1122756_85-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWeinerJohansson1975" class="citation journal cs1">Weiner E, Johansson ED (April 1975). "Plasma levels of norethindrone after i.m. injection of 200 mg norethindrone enanthate". Contraception. 11 (4): 419–25. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0010-7824%2875%2990004-9">10.1016/0010-7824(75)90004-9</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/1122756">1122756</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Contraception&rft.atitle=Plasma+levels+of+norethindrone+after+i.m.+injection+of+200+mg+norethindrone+enanthate&rft.volume=11&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E419-%3C%2Fspan%3E25&rft.date=1975-04&rft_id=info%3Adoi%2F10.1016%2F0010-7824%2875%2990004-9&rft_id=info%3Apmid%2F1122756&rft.aulast=Weiner&rft.aufirst=E&rft.au=Johansson%2C+ED&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid606499-86"><a href="#cite_ref-pmid606499_86-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFotherbyHowardShrimankerElder1977" class="citation journal cs1">Fotherby K, Howard G, Shrimanker K, Elder M, Bye PG (December 1977). "Effect of norethisterone oenanthate on serum gonadotrophin levels". Contraception. 16 (6): 591–604. <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%2F0010-7824%2877%2990060-9">10.1016/0010-7824(77)90060-9</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/606499">606499</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Contraception&rft.atitle=Effect+of+norethisterone+oenanthate+on+serum+gonadotrophin+levels&rft.volume=16&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E591-%3C%2Fspan%3E604&rft.date=1977-12&rft_id=info%3Adoi%2F10.1016%2F0010-7824%2877%2990060-9&rft_id=info%3Apmid%2F606499&rft.aulast=Fotherby&rft.aufirst=K&rft.au=Howard%2C+G&rft.au=Shrimanker%2C+K&rft.au=Elder%2C+M&rft.au=Bye%2C+PG&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid572279-87"><a href="#cite_ref-pmid572279_87-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFGoebelsmannStanczykBrennerGoebelsmann1979" class="citation journal cs1">Goebelsmann U, Stanczyk FZ, Brenner PF, Goebelsmann AE, Gentzschein EK, Mishell DR (March 1979). "Serum norethindrone (NET) concentrations following intramuscular NET enanthate injection. Effect upon serum LH, FSH, estradiol and progesterone". Contraception. 19 (3): 283–313. <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%2F0010-7824%2879%2990022-2">10.1016/0010-7824(79)90022-2</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/572279">572279</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Contraception&rft.atitle=Serum+norethindrone+%28NET%29+concentrations+following+intramuscular+NET+enanthate+injection.+Effect+upon+serum+LH%2C+FSH%2C+estradiol+and+progesterone&rft.volume=19&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E283-%3C%2Fspan%3E313&rft.date=1979-03&rft_id=info%3Adoi%2F10.1016%2F0010-7824%2879%2990022-2&rft_id=info%3Apmid%2F572279&rft.aulast=Goebelsmann&rft.aufirst=U&rft.au=Stanczyk%2C+FZ&rft.au=Brenner%2C+PF&rft.au=Goebelsmann%2C+AE&rft.au=Gentzschein%2C+EK&rft.au=Mishell%2C+DR&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid793446-88">^ <a href="#cite_ref-pmid793446_88-0">a</a> <a href="#cite_ref-pmid793446_88-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFNeumannDialloHasanSchenck1976" class="citation journal cs1">Neumann F, Diallo FA, Hasan SH, Schenck B, Traore I (1976). <a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1439-0272.1976.tb02137.x">"The influence of pharmaceutical compounds on male fertility"</a>. Andrologia. 8 (3): 203–35. <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.1439-0272.1976.tb02137.x">10.1111/j.1439-0272.1976.tb02137.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/793446">793446</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:24859886">24859886</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Andrologia&rft.atitle=The+influence+of+pharmaceutical+compounds+on+male+fertility&rft.volume=8&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E203-%3C%2Fspan%3E35&rft.date=1976&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A24859886%23id-name%3DS2CID&rft_id=info%3Apmid%2F793446&rft_id=info%3Adoi%2F10.1111%2Fj.1439-0272.1976.tb02137.x&rft.aulast=Neumann&rft.aufirst=F&rft.au=Diallo%2C+FA&rft.au=Hasan%2C+SH&rft.au=Schenck%2C+B&rft.au=Traore%2C+I&rft_id=https%3A%2F%2Fdoi.org%2F10.1111%252Fj.1439-0272.1976.tb02137.x&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid13583821-89"><a href="#cite_ref-pmid13583821_89-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHellerLaidlawHarveyNelson1958" class="citation journal cs1">Heller CG, Laidlaw WM, Harvey HT, Nelson WO (July 1958). "Effects of progestational compounds on the reproductive processes of the human male". Annals of the New York Academy of Sciences. 71 (5): 649–65. <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.1749-6632.1958.tb54641.x">10.1111/j.1749-6632.1958.tb54641.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/13583821">13583821</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:32637425">32637425</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+the+New+York+Academy+of+Sciences&rft.atitle=Effects+of+progestational+compounds+on+the+reproductive+processes+of+the+human+male&rft.volume=71&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E649-%3C%2Fspan%3E65&rft.date=1958-07&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A32637425%23id-name%3DS2CID&rft_id=info%3Apmid%2F13583821&rft_id=info%3Adoi%2F10.1111%2Fj.1749-6632.1958.tb54641.x&rft.aulast=Heller&rft.aufirst=CG&rft.au=Laidlaw%2C+WM&rft.au=Harvey%2C+HT&rft.au=Nelson%2C+WO&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid14400846-90"><a href="#cite_ref-pmid14400846_90-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHellerMoorePaulsenNelson1959" class="citation journal cs1">Heller CG, Moore DJ, Paulsen CA, Nelson WO, Laidlaw WM (December 1959). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20181218193350/https://www.popline.org/node/472874">"Effects of progesterone and synthetic progestins on the reproductive physiology of normal men"</a>. Federation Proceedings. 18: 1057–65. <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/14400846">14400846</a>. Archived from <a rel="nofollow" class="external text" href="https://www.popline.org/node/472874">the original</a> on 18 December 2018. Retrieved 11 December 2019.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Federation+Proceedings&rft.atitle=Effects+of+progesterone+and+synthetic+progestins+on+the+reproductive+physiology+of+normal+men&rft.volume=18&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1057-%3C%2Fspan%3E65&rft.date=1959-12&rft_id=info%3Apmid%2F14400846&rft.aulast=Heller&rft.aufirst=CG&rft.au=Moore%2C+DJ&rft.au=Paulsen%2C+CA&rft.au=Nelson%2C+WO&rft.au=Laidlaw%2C+WM&rft_id=https%3A%2F%2Fwww.popline.org%2Fnode%2F472874&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid14261416-91"><a href="#cite_ref-pmid14261416_91-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPaulsen1965" class="citation journal cs1">Paulsen CA (March 1965). "Progestin Metabolism: Special Reference to Estrogenic Pathways". Metabolism. 14 (3): SUPPL:313–19. <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%2F0026-0495%2865%2990018-1">10.1016/0026-0495(65)90018-1</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/14261416">14261416</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Metabolism&rft.atitle=Progestin+Metabolism%3A+Special+Reference+to+Estrogenic+Pathways&rft.volume=14&rft.issue=3&rft.pages=SUPPL%3A313-19&rft.date=1965-03&rft_id=info%3Adoi%2F10.1016%2F0026-0495%2865%2990018-1&rft_id=info%3Apmid%2F14261416&rft.aulast=Paulsen&rft.aufirst=CA&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-MougdalSuresh1995-92"><a href="#cite_ref-MougdalSuresh1995_92-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMoudgalSuresh1995" class="citation journal cs1">Moudgal NR, Suresh R (1995). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20191211133812/https://www.currentscience.ac.in/Downloads/article_id_068_04_0470_0474_0.pdf">"Some thoughts on development of chemically based male contraceptives"</a> (PDF). Current Science (Bangalore). 68 (4): 470–74. <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/0011-3891">0011-3891</a>. Archived from <a rel="nofollow" class="external text" href="https://www.currentscience.ac.in/Downloads/article_id_068_04_0470_0474_0.pdf">the original</a> (PDF) on 11 December 2019. Retrieved 11 December 2019.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Current+Science+%28Bangalore%29&rft.atitle=Some+thoughts+on+development+of+chemically+based+male+contraceptives&rft.volume=68&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E470-%3C%2Fspan%3E74&rft.date=1995&rft.issn=0011-3891&rft.aulast=Moudgal&rft.aufirst=NR&rft.au=Suresh%2C+R&rft_id=https%3A%2F%2Fwww.currentscience.ac.in%2FDownloads%2Farticle_id_068_04_0470_0474_0.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-JohonssonNygren1973-93"><a href="#cite_ref-JohonssonNygren1973_93-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFJohonssonNygren1973" class="citation journal cs1">Johonsson ED, Nygren KG (1973). "Depression of plasma testosterone levels in men with norethindrone". Contraception. 8 (3): 219–26. <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%2F0010-7824%2873%2990032-2">10.1016/0010-7824(73)90032-2</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/0010-7824">0010-7824</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Contraception&rft.atitle=Depression+of+plasma+testosterone+levels+in+men+with+norethindrone&rft.volume=8&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E219-%3C%2Fspan%3E26&rft.date=1973&rft_id=info%3Adoi%2F10.1016%2F0010-7824%2873%2990032-2&rft.issn=0010-7824&rft.aulast=Johonsson&rft.aufirst=ED&rft.au=Nygren%2C+KG&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid28189123-94"><a href="#cite_ref-pmid28189123_94-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFZitzmannRohayemRaidtKliesch2017" class="citation journal cs1">Zitzmann M, Rohayem J, Raidt J, Kliesch S, Kumar N, Sitruk-Ware R, et al. (May 2017). <a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fandr.12328">"Impact of various progestins with or without transdermal testosterone on gonadotropin levels for non-invasive hormonal male contraception: a randomized clinical trial"</a>. Andrology. 5 (3): 516–26. <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%2Fandr.12328">10.1111/andr.12328</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/28189123">28189123</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:41502711">41502711</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Andrology&rft.atitle=Impact+of+various+progestins+with+or+without+transdermal+testosterone+on+gonadotropin+levels+for+non-invasive+hormonal+male+contraception%3A+a+randomized+clinical+trial&rft.volume=5&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E516-%3C%2Fspan%3E26&rft.date=2017-05&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A41502711%23id-name%3DS2CID&rft_id=info%3Apmid%2F28189123&rft_id=info%3Adoi%2F10.1111%2Fandr.12328&rft.aulast=Zitzmann&rft.aufirst=M&rft.au=Rohayem%2C+J&rft.au=Raidt%2C+J&rft.au=Kliesch%2C+S&rft.au=Kumar%2C+N&rft.au=Sitruk-Ware%2C+R&rft.au=Nieschlag%2C+E&rft_id=https%3A%2F%2Fdoi.org%2F10.1111%252Fandr.12328&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-ValleAlvarez2011-95">^ <a href="#cite_ref-ValleAlvarez2011_95-0">a</a> <a href="#cite_ref-ValleAlvarez2011_95-1">b</a> <a href="#cite_ref-ValleAlvarez2011_95-2">c</a> <a href="#cite_ref-ValleAlvarez2011_95-3">d</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFAlvarez2011" class="citation thesis cs1">Alvarez BD (11 May 2011). <a rel="nofollow" class="external text" href="http://repositoriodigital.ipn.mx/handle/123456789/12490">Efecto de una Dosis de 50 mg de Enantato de Noretisterona y 5 mg de Valerato de Estradiol en los Niveles de Testosterona Total en Hombres Mexicanos Sanos</a> [Effect of a Dose of 50 mg of Norethisterone Enanthate and 5 mg of Estradiol Valerate on Total Testosterone Levels in Healthy Mexican Men] (MSc). National Polytechnic Institute of Mexico. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20220916063742/https://repositoriodigital.ipn.mx/handle/123456789/12490">Archived</a> from the original on 16 September 2022. Retrieved 12 September 2022.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Adissertation&rft.title=Efecto+de+una+Dosis+de+50+mg+de+Enantato+de+Noretisterona+y+5+mg+de+Valerato+de+Estradiol+en+los+Niveles+de+Testosterona+Total+en+Hombres+Mexicanos+Sanos&rft.inst=National+Polytechnic+Institute+of+Mexico&rft.date=2011-05-11&rft.aulast=Alvarez&rft.aufirst=BD&rft_id=http%3A%2F%2Frepositoriodigital.ipn.mx%2Fhandle%2F123456789%2F12490&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-Amory2003-96"><a href="#cite_ref-Amory2003_96-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFAmory2003" class="citation book cs1">Amory JK (2003). "Androgens and Male Contraception". Androgens in Health and Disease. Contemporary Endocrinology. Humana Press. pp. 405–17. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-1-59259-388-0_21">10.1007/978-1-59259-388-0_21</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-61737-314-5" title="Special:BookSources/978-1-61737-314-5"><bdi>978-1-61737-314-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Androgens+and+Male+Contraception&rft.btitle=Androgens+in+Health+and+Disease&rft.series=Contemporary+Endocrinology&rft.pages=%3Cspan+class%3D%22nowrap%22%3E405-%3C%2Fspan%3E17&rft.pub=Humana+Press&rft.date=2003&rft_id=info%3Adoi%2F10.1007%2F978-1-59259-388-0_21&rft.isbn=978-1-61737-314-5&rft.aulast=Amory&rft.aufirst=JK&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid10971453-97"><a href="#cite_ref-pmid10971453_97-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKamischkeDiebäckerNieschlag2000" class="citation journal cs1">Kamischke A, Diebäcker J, Nieschlag E (September 2000). "Potential of norethisterone enanthate for male contraception: pharmacokinetics and suppression of pituitary and gonadal function". Clinical Endocrinology. 53 (3): 351–58. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1046%2Fj.1365-2265.2000.01097.x">10.1046/j.1365-2265.2000.01097.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/10971453">10971453</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:70515136">70515136</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Clinical+Endocrinology&rft.atitle=Potential+of+norethisterone+enanthate+for+male+contraception%3A+pharmacokinetics+and+suppression+of+pituitary+and+gonadal+function&rft.volume=53&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E351-%3C%2Fspan%3E58&rft.date=2000-09&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A70515136%23id-name%3DS2CID&rft_id=info%3Apmid%2F10971453&rft_id=info%3Adoi%2F10.1046%2Fj.1365-2265.2000.01097.x&rft.aulast=Kamischke&rft.aufirst=A&rft.au=Dieb%C3%A4cker%2C+J&rft.au=Nieschlag%2C+E&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-PetryMauss1970-98"><a href="#cite_ref-PetryMauss1970_98-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPetryMaussSengeRausch-Stroomann1970" class="citation journal cs1">Petry R, Mauss J, Senge T, Rausch-Stroomann JG (1970). "Über den Einfluß von Cyproteronacetat, Norethisteronönanthat und Gestonoroncapronat auf die Hypophysen-Gonadenachse beim Mann: Influence of Cyproterone-acetate, Norethisterone-enanthate and Gestonorone-capronate on the Hypophyseal-Gonadal-Axis in the Male" [Influence of Cyproterone-acetate, Norethisterone-enanthate and Gestonorone-capronate on the Hypophyseal-Gonadal-Axis in the Male]. Endokrinologie der Entwicklung und Reifung. Symposion der Deutschen Gesellschaft für Endokrinologie in Ulm vom 26–28 Februar 1970. Springer: 428–30. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-3-642-80591-2_118">10.1007/978-3-642-80591-2_118</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9783642805912" title="Special:BookSources/9783642805912"><bdi>9783642805912</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Endokrinologie+der+Entwicklung+und+Reifung&rft.atitle=%C3%9Cber+den+Einflu%C3%9F+von+Cyproteronacetat%2C+Norethisteron%C3%B6nanthat+und+Gestonoroncapronat+auf+die+Hypophysen-Gonadenachse+beim+Mann%3A+Influence+of+Cyproterone-acetate%2C+Norethisterone-enanthate+and+Gestonorone-capronate+on+the+Hypophyseal-Gonadal-Axis+in+the+Male&rft.pages=%3Cspan+class%3D%22nowrap%22%3E428-%3C%2Fspan%3E30&rft.date=1970&rft_id=info%3Adoi%2F10.1007%2F978-3-642-80591-2_118&rft.isbn=9783642805912&rft.aulast=Petry&rft.aufirst=R&rft.au=Mauss%2C+J&rft.au=Senge%2C+T&rft.au=Rausch-Stroomann%2C+JG&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-Springer2013-99">^ <a href="#cite_ref-Springer2013_99-0">a</a> <a href="#cite_ref-Springer2013_99-1">b</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=t8GpBgAAQBAJ&pg=PA13">Die Gestagene</a>. Springer-Verlag. 2013. pp. 13–14, 283–84. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-99941-3" title="Special:BookSources/978-3-642-99941-3"><bdi>978-3-642-99941-3</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230110231243/https://books.google.com/books?id=t8GpBgAAQBAJ&pg=PA13">Archived</a> from the original on 10 January 2023. Retrieved 19 September 2018.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Die+Gestagene&rft.pages=%3Cspan+class%3D%22nowrap%22%3E13-%3C%2Fspan%3E14%2C+%3Cspan+class%3D%22nowrap%22%3E283-%3C%2Fspan%3E84&rft.pub=Springer-Verlag&rft.date=2013&rft.isbn=978-3-642-99941-3&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dt8GpBgAAQBAJ%26pg%3DPA13&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid2620531-100"><a href="#cite_ref-pmid2620531_100-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSapersteinEdgrenJungMroszczak1989" class="citation journal cs1">Saperstein S, Edgren RA, Jung D, Mroszczak EJ, Lee GJ, Dorr A, et al. (December 1989). "Pharmacokinetics of norethindrone: effect of particle size". Contraception. 40 (6): 731–40. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0010-7824%2889%2990075-9">10.1016/0010-7824(89)90075-9</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/2620531">2620531</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Contraception&rft.atitle=Pharmacokinetics+of+norethindrone%3A+effect+of+particle+size&rft.volume=40&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E731-%3C%2Fspan%3E40&rft.date=1989-12&rft_id=info%3Adoi%2F10.1016%2F0010-7824%2889%2990075-9&rft_id=info%3Apmid%2F2620531&rft.aulast=Saperstein&rft.aufirst=S&rft.au=Edgren%2C+RA&rft.au=Jung%2C+D&rft.au=Mroszczak%2C+EJ&rft.au=Lee%2C+GJ&rft.au=Dorr%2C+A&rft.au=Pritchard%2C+R&rft.au=Kushinsky%2C+S&rft.au=Fong%2C+JC&rft.au=Combs%2C+DL&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid29522253-101"><a href="#cite_ref-pmid29522253_101-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFriedrichBerseKleinRohde2018" class="citation journal cs1">Friedrich C, Berse M, Klein S, Rohde B, Höchel J (June 2018). "In Vivo Formation of Ethinylestradiol After Intramuscular Administration of Norethisterone Enantate". Journal of Clinical Pharmacology. 58 (6): 781–89. <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%2Fjcph.1079">10.1002/jcph.1079</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/29522253">29522253</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:3813229">3813229</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Clinical+Pharmacology&rft.atitle=In+Vivo+Formation+of+Ethinylestradiol+After+Intramuscular+Administration+of+Norethisterone+Enantate&rft.volume=58&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E781-%3C%2Fspan%3E89&rft.date=2018-06&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A3813229%23id-name%3DS2CID&rft_id=info%3Apmid%2F29522253&rft_id=info%3Adoi%2F10.1002%2Fjcph.1079&rft.aulast=Friedrich&rft.aufirst=C&rft.au=Berse%2C+M&rft.au=Klein%2C+S&rft.au=Rohde%2C+B&rft.au=H%C3%B6chel%2C+J&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-Thijssen1972-102"><a href="#cite_ref-Thijssen1972_102-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFThijssen1972" class="citation book cs1">Thijssen JH (1972). "Metabolism of Orally Active Synthetic Progestational Compounds". In Tausk M (ed.). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=Nv5sAAAAMAAJ">Pharmacology of the Endocrine System and Related Drugs: Progesterone, Progestational Drugs and Antifertility Agents</a>. Vol. II. Pergamon Press. pp. 217–73. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0080168128" title="Special:BookSources/978-0080168128"><bdi>978-0080168128</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/278011135">278011135</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Metabolism+of+Orally+Active+Synthetic+Progestational+Compounds&rft.btitle=Pharmacology+of+the+Endocrine+System+and+Related+Drugs%3A+Progesterone%2C+Progestational+Drugs+and+Antifertility+Agents&rft.pages=%3Cspan+class%3D%22nowrap%22%3E217-%3C%2Fspan%3E73&rft.pub=Pergamon+Press&rft.date=1972&rft_id=info%3Aoclcnum%2F278011135&rft.isbn=978-0080168128&rft.aulast=Thijssen&rft.aufirst=JH&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DNv5sAAAAMAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-Okada2010-103"><a href="#cite_ref-Okada2010_103-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFOkada2010" class="citation journal cs1">Okada H (2010). "Receptors and Mechanism Action of Synthetic Progestogens". Asia-Oceania Journal of Obstetrics and Gynaecology. 7 (1): 15–27. <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.1447-0756.1981.tb00511.x">10.1111/j.1447-0756.1981.tb00511.x</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/0389-2328">0389-2328</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Asia-Oceania+Journal+of+Obstetrics+and+Gynaecology&rft.atitle=Receptors+and+Mechanism+Action+of+Synthetic+Progestogens&rft.volume=7&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E15-%3C%2Fspan%3E27&rft.date=2010&rft_id=info%3Adoi%2F10.1111%2Fj.1447-0756.1981.tb00511.x&rft.issn=0389-2328&rft.aulast=Okada&rft.aufirst=H&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-Briggs1980-104"><a href="#cite_ref-Briggs1980_104-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBriggs1980" class="citation book cs1">Briggs MH (1980). "Comparative Pharmacodynamics and Pharmacokinetics of Contraceptive Steroids in Animals and Man: A Selective Review". Clinical Pharmacology & Therapeutics. Palgrave Macmillan UK. pp. 493–518. <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%2F978-1-349-05952-2_57">10.1007/978-1-349-05952-2_57</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-349-05954-6" title="Special:BookSources/978-1-349-05954-6"><bdi>978-1-349-05954-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Comparative+Pharmacodynamics+and+Pharmacokinetics+of+Contraceptive+Steroids+in+Animals+and+Man%3A+A+Selective+Review&rft.btitle=Clinical+Pharmacology+%26+Therapeutics&rft.pages=%3Cspan+class%3D%22nowrap%22%3E493-%3C%2Fspan%3E518&rft.pub=Palgrave+Macmillan+UK&rft.date=1980&rft_id=info%3Adoi%2F10.1007%2F978-1-349-05952-2_57&rft.isbn=978-1-349-05954-6&rft.aulast=Briggs&rft.aufirst=MH&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-ThomasKeenan1986-105"><a href="#cite_ref-ThomasKeenan1986_105-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFThomasKeenan1986" class="citation book cs1">Thomas JA, Keenan EJ (1986). "Progestins and Oral Contraceptives". Principles of Endocrine Pharmacology. Springer. pp. 167–96. <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%2F978-1-4684-5036-1_8">10.1007/978-1-4684-5036-1_8</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4684-5036-1" title="Special:BookSources/978-1-4684-5036-1"><bdi>978-1-4684-5036-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Progestins+and+Oral+Contraceptives&rft.btitle=Principles+of+Endocrine+Pharmacology&rft.pages=%3Cspan+class%3D%22nowrap%22%3E167-%3C%2Fspan%3E96&rft.pub=Springer&rft.date=1986&rft_id=info%3Adoi%2F10.1007%2F978-1-4684-5036-1_8&rft.isbn=978-1-4684-5036-1&rft.aulast=Thomas&rft.aufirst=JA&rft.au=Keenan%2C+EJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid6342899-106"><a href="#cite_ref-pmid6342899_106-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFOrmeBackBreckenridge1983" class="citation journal cs1">Orme ML, Back DJ, Breckenridge AM (1983). "Clinical pharmacokinetics of oral contraceptive steroids". Clinical Pharmacokinetics. 8 (2): 95–136. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.2165%2F00003088-198308020-00001">10.2165/00003088-198308020-00001</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/6342899">6342899</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:43298472">43298472</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Clinical+Pharmacokinetics&rft.atitle=Clinical+pharmacokinetics+of+oral+contraceptive+steroids&rft.volume=8&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E95-%3C%2Fspan%3E136&rft.date=1983&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A43298472%23id-name%3DS2CID&rft_id=info%3Apmid%2F6342899&rft_id=info%3Adoi%2F10.2165%2F00003088-198308020-00001&rft.aulast=Orme&rft.aufirst=ML&rft.au=Back%2C+DJ&rft.au=Breckenridge%2C+AM&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid4206183-107"><a href="#cite_ref-pmid4206183_107-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFotherby1974" class="citation journal cs1">Fotherby K (1974). "Metabolism of synthetic steroids by animals and man". Acta Endocrinologica. Supplementum. 185: 119–47. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1530%2Facta.0.075s119">10.1530/acta.0.075s119</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/4206183">4206183</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Endocrinologica.+Supplementum&rft.atitle=Metabolism+of+synthetic+steroids+by+animals+and+man&rft.volume=185&rft.pages=%3Cspan+class%3D%22nowrap%22%3E119-%3C%2Fspan%3E47&rft.date=1974&rft_id=info%3Adoi%2F10.1530%2Facta.0.075s119&rft_id=info%3Apmid%2F4206183&rft.aulast=Fotherby&rft.aufirst=K&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid17653961-108"><a href="#cite_ref-pmid17653961_108-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKuhlWiegratz2007" class="citation journal cs1">Kuhl H, Wiegratz I (August 2007). "Can 19-nortestosterone derivatives be aromatized in the liver of adult humans? Are there clinical implications?". Climacteric. 10 (4): 344–53. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F13697130701380434">10.1080/13697130701380434</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/17653961">17653961</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:20759583">20759583</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Climacteric&rft.atitle=Can+19-nortestosterone+derivatives+be+aromatized+in+the+liver+of+adult+humans%3F+Are+there+clinical+implications%3F&rft.volume=10&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E344-%3C%2Fspan%3E53&rft.date=2007-08&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A20759583%23id-name%3DS2CID&rft_id=info%3Apmid%2F17653961&rft_id=info%3Adoi%2F10.1080%2F13697130701380434&rft.aulast=Kuhl&rft.aufirst=H&rft.au=Wiegratz%2C+I&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-StanczykRoy1990-109"><a href="#cite_ref-StanczykRoy1990_109-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFStanczykRoy1990" class="citation journal cs1">Stanczyk FZ, Roy S (July 1990). "Metabolism of levonorgestrel, norethindrone, and structurally related contraceptive steroids". Contraception. 42 (1): 67–96. <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%2F0010-7824%2890%2990093-B">10.1016/0010-7824(90)90093-B</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/2143719">2143719</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Contraception&rft.atitle=Metabolism+of+levonorgestrel%2C+norethindrone%2C+and+structurally+related+contraceptive+steroids&rft.volume=42&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E67-%3C%2Fspan%3E96&rft.date=1990-07&rft_id=info%3Adoi%2F10.1016%2F0010-7824%2890%2990093-B&rft_id=info%3Apmid%2F2143719&rft.aulast=Stanczyk&rft.aufirst=FZ&rft.au=Roy%2C+S&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid11162927-110">^ <a href="#cite_ref-pmid11162927_110-0">a</a> <a href="#cite_ref-pmid11162927_110-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSchoonenDeckersde_Gooijerde_Ries2000" class="citation journal cs1">Schoonen WG, Deckers GH, de Gooijer ME, de Ries R, Kloosterboer HJ (November 2000). "Hormonal properties of norethisterone, 7alpha-methyl-norethisterone and their derivatives". The Journal of Steroid Biochemistry and Molecular Biology. 74 (4): 213–22. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fs0960-0760%2800%2900125-4">10.1016/s0960-0760(00)00125-4</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/11162927">11162927</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:19797254">19797254</a>. <q>[...] several mono- and disulphated as well as mono- and diglucuronidated metabolites of NET have been detected in urine from NET treated women [16,17]. In unconjugated form these NET (or MeNET) metabolites are represented by 5α- and 5β-reduced NET (5α-NET or 5β-NET) and by 3α- and 3β-hydrogenated 5α-NET and 5β-NET, leading to 3α,5α-NET, 3β,5α-NET, 3α,5β-NET and 3β,5β-NET or their corresponding MeNET metabolites (Figs. 1 and 2). These steroid conversions of NET or MeNET may take place in the liver, but also in the pituitary, endometrium, prostate, vagina and breast. The enzymes involved in these metabolic processes are 5α- and 5β-reductase as well as 3α- and 3β-hydroxysteroid dehydrogenase (HSD).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Steroid+Biochemistry+and+Molecular+Biology&rft.atitle=Hormonal+properties+of+norethisterone%2C+7alpha-methyl-norethisterone+and+their+derivatives&rft.volume=74&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E213-%3C%2Fspan%3E22&rft.date=2000-11&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A19797254%23id-name%3DS2CID&rft_id=info%3Apmid%2F11162927&rft_id=info%3Adoi%2F10.1016%2Fs0960-0760%2800%2900125-4&rft.aulast=Schoonen&rft.aufirst=WG&rft.au=Deckers%2C+GH&rft.au=de+Gooijer%2C+ME&rft.au=de+Ries%2C+R&rft.au=Kloosterboer%2C+HJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid3871879-111"><a href="#cite_ref-pmid3871879_111-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFChávezVilchisPérezGarcía1985" class="citation journal cs1">Chávez BA, Vilchis F, Pérez AE, García GA, Grillasca I, Pérez-Palacios G (January 1985). <a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0022-4731%2885%2990151-7">"Stereospecificity of the intracellular binding of norethisterone and its A-ring reduced metabolites"</a>. Journal of Steroid Biochemistry. 22 (1): 121–26. <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%2F0022-4731%2885%2990151-7">10.1016/0022-4731(85)90151-7</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/3871879">3871879</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+Steroid+Biochemistry&rft.atitle=Stereospecificity+of+the+intracellular+binding+of+norethisterone+and+its+A-ring+reduced+metabolites&rft.volume=22&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E121-%3C%2Fspan%3E26&rft.date=1985-01&rft_id=info%3Adoi%2F10.1016%2F0022-4731%2885%2990151-7&rft_id=info%3Apmid%2F3871879&rft.aulast=Ch%C3%A1vez&rft.aufirst=BA&rft.au=Vilchis%2C+F&rft.au=P%C3%A9rez%2C+AE&rft.au=Garc%C3%ADa%2C+GA&rft.au=Grillasca%2C+I&rft.au=P%C3%A9rez-Palacios%2C+G&rft_id=https%3A%2F%2Fdoi.org%2F10.1016%252F0022-4731%252885%252990151-7&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid3090814-112"><a href="#cite_ref-pmid3090814_112-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFGarza-FloresVilchisGarcíaMenjívar1986" class="citation journal cs1">Garza-Flores J, Vilchis F, García GA, Menjívar M, Pérez-Palacios G (June 1986). "A-ring reduction enhances the antigonadotropic potency of norethisterone". Acta Endocrinologica. 112 (2): 278–83. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1530%2Facta.0.1120278">10.1530/acta.0.1120278</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/3090814">3090814</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Endocrinologica&rft.atitle=A-ring+reduction+enhances+the+antigonadotropic+potency+of+norethisterone&rft.volume=112&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E278-%3C%2Fspan%3E83&rft.date=1986-06&rft_id=info%3Adoi%2F10.1530%2Facta.0.1120278&rft_id=info%3Apmid%2F3090814&rft.aulast=Garza-Flores&rft.aufirst=J&rft.au=Vilchis%2C+F&rft.au=Garc%C3%ADa%2C+GA&rft.au=Menj%C3%ADvar%2C+M&rft.au=P%C3%A9rez-Palacios%2C+G&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid19008332-113"><a href="#cite_ref-pmid19008332_113-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLemusEnríquezHernándezSantillán2009" class="citation journal cs1">Lemus AE, Enríquez J, Hernández A, Santillán R, Pérez-Palacios G (February 2009). <a rel="nofollow" class="external text" href="https://doi.org/10.1677%2FJOE-08-0166">"Bioconversion of norethisterone, a progesterone receptor agonist into estrogen receptor agonists in osteoblastic cells"</a>. The Journal of Endocrinology. 200 (2): 199–206. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1677%2FJOE-08-0166">10.1677/JOE-08-0166</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/19008332">19008332</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=Bioconversion+of+norethisterone%2C+a+progesterone+receptor+agonist+into+estrogen+receptor+agonists+in+osteoblastic+cells&rft.volume=200&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E199-%3C%2Fspan%3E206&rft.date=2009-02&rft_id=info%3Adoi%2F10.1677%2FJOE-08-0166&rft_id=info%3Apmid%2F19008332&rft.aulast=Lemus&rft.aufirst=AE&rft.au=Enr%C3%ADquez%2C+J&rft.au=Hern%C3%A1ndez%2C+A&rft.au=Santill%C3%A1n%2C+R&rft.au=P%C3%A9rez-Palacios%2C+G&rft_id=https%3A%2F%2Fdoi.org%2F10.1677%252FJOE-08-0166&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-ScarsiDarin2016-114"><a href="#cite_ref-ScarsiDarin2016_114-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFScarsiDarinChappellNitz2016" class="citation journal cs1">Scarsi KK, Darin KM, Chappell CA, Nitz SM, Lamorde M (November 2016). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5048570">"Drug-Drug Interactions, Effectiveness, and Safety of Hormonal Contraceptives in Women Living with HIV"</a>. Drug Safety. 39 (11): 1053–72. <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%2Fs40264-016-0452-7">10.1007/s40264-016-0452-7</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/PMC5048570">5048570</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/27562873">27562873</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Drug+Safety&rft.atitle=Drug-Drug+Interactions%2C+Effectiveness%2C+and+Safety+of+Hormonal+Contraceptives+in+Women+Living+with+HIV&rft.volume=39&rft.issue=11&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1053-%3C%2Fspan%3E72&rft.date=2016-11&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5048570%23id-name%3DPMC&rft_id=info%3Apmid%2F27562873&rft_id=info%3Adoi%2F10.1007%2Fs40264-016-0452-7&rft.aulast=Scarsi&rft.aufirst=KK&rft.au=Darin%2C+KM&rft.au=Chappell%2C+CA&rft.au=Nitz%2C+SM&rft.au=Lamorde%2C+M&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5048570&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-DeGroot2001-115"><a href="#cite_ref-DeGroot2001_115-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDeGroot2001" class="citation book cs1">DeGroot LJ (2001). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=NBdsAAAAMAAJ">Endocrinology</a>. W.B. Saunders Co. p. 2617. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7216-7843-6" title="Special:BookSources/978-0-7216-7843-6"><bdi>978-0-7216-7843-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Endocrinology&rft.pages=2617&rft.pub=W.B.+Saunders+Co.&rft.date=2001&rft.isbn=978-0-7216-7843-6&rft.aulast=DeGroot&rft.aufirst=LJ&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DNBdsAAAAMAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-Elks2014-116">^ <a href="#cite_ref-Elks2014_116-0">a</a> <a href="#cite_ref-Elks2014_116-1">b</a> <a href="#cite_ref-Elks2014_116-2">c</a> <a href="#cite_ref-Elks2014_116-3">d</a> <a href="#cite_ref-Elks2014_116-4">e</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFElks2014" class="citation book cs1">Elks J (2014). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA886">The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies</a>. Springer. pp. 886–. <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/20230110231242/https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA886">Archived</a> from the original on 10 January 2023. Retrieved 5 October 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Dictionary+of+Drugs%3A+Chemical+Data%3A+Chemical+Data%2C+Structures+and+Bibliographies&rft.pages=886-&rft.pub=Springer&rft.date=2014&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%3DPA886&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-IN2000-117">^ <a href="#cite_ref-IN2000_117-0">a</a> <a href="#cite_ref-IN2000_117-1">b</a> <a href="#cite_ref-IN2000_117-2">c</a> <a href="#cite_ref-IN2000_117-3">d</a> <a href="#cite_ref-IN2000_117-4">e</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=5GpcTQD_L2oC&pg=PA749">Index Nominum 2000: International Drug Directory</a>. Taylor & Francis. 2000. pp. 749–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-88763-075-1" title="Special:BookSources/978-3-88763-075-1"><bdi>978-3-88763-075-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Index+Nominum+2000%3A+International+Drug+Directory&rft.pages=749-&rft.pub=Taylor+%26+Francis&rft.date=2000&rft.isbn=978-3-88763-075-1&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D5GpcTQD_L2oC%26pg%3DPA749&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-Chwalisz,_K._2012-118"><a href="#cite_ref-Chwalisz,_K._2012_118-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFChwaliszSurreyStanczyk2012" class="citation journal cs1">Chwalisz K, Surrey E, Stanczyk FZ (June 2012). "The hormonal profile of norethindrone acetate: rationale for add-back therapy with gonadotropin-releasing hormone agonists in women with endometriosis". Reproductive Sciences. 19 (6): 563–71. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1177%2F1933719112438061">10.1177/1933719112438061</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/22457429">22457429</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:2882899">2882899</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Reproductive+Sciences&rft.atitle=The+hormonal+profile+of+norethindrone+acetate%3A+rationale+for+add-back+therapy+with+gonadotropin-releasing+hormone+agonists+in+women+with+endometriosis&rft.volume=19&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E563-%3C%2Fspan%3E71&rft.date=2012-06&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A2882899%23id-name%3DS2CID&rft_id=info%3Apmid%2F22457429&rft_id=info%3Adoi%2F10.1177%2F1933719112438061&rft.aulast=Chwalisz&rft.aufirst=K&rft.au=Surrey%2C+E&rft.au=Stanczyk%2C+FZ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-ShoupeHaseltine2012-119"><a href="#cite_ref-ShoupeHaseltine2012_119-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFShoupeHaseltine2012" class="citation book cs1">Shoupe D, Haseltine FP (2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=cpDhBwAAQBAJ&pg=PA112">Contraception</a>. Springer Science & Business Media. pp. 112–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4612-2730-4" title="Special:BookSources/978-1-4612-2730-4"><bdi>978-1-4612-2730-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Contraception&rft.pages=112-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012&rft.isbn=978-1-4612-2730-4&rft.aulast=Shoupe&rft.aufirst=D&rft.au=Haseltine%2C+FP&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DcpDhBwAAQBAJ%26pg%3DPA112&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-Ryan1999-120"><a href="#cite_ref-Ryan1999_120-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRyan1999" class="citation book cs1">Ryan KJ (1999). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=i8xsAAAAMAAJ">Kistner's Gynecology and Women's Health</a>. Mosby. p. 292. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-323-00201-1" title="Special:BookSources/978-0-323-00201-1"><bdi>978-0-323-00201-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Kistner%27s+Gynecology+and+Women%27s+Health&rft.pages=292&rft.pub=Mosby&rft.date=1999&rft.isbn=978-0-323-00201-1&rft.aulast=Ryan&rft.aufirst=KJ&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Di8xsAAAAMAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid2256526-121"><a href="#cite_ref-pmid2256526_121-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHammerstein1990" class="citation journal cs1">Hammerstein J (December 1990). "Prodrugs: advantage or disadvantage?". American Journal of Obstetrics and Gynecology. 163 (6 Pt 2): 2198–203. <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%2F0002-9378%2890%2990561-K">10.1016/0002-9378(90)90561-K</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/2256526">2256526</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=American+Journal+of+Obstetrics+and+Gynecology&rft.atitle=Prodrugs%3A+advantage+or+disadvantage%3F&rft.volume=163&rft.issue=6+Pt+2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E2198-%3C%2Fspan%3E203&rft.date=1990-12&rft_id=info%3Adoi%2F10.1016%2F0002-9378%2890%2990561-K&rft_id=info%3Apmid%2F2256526&rft.aulast=Hammerstein&rft.aufirst=J&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid20851224-122"><a href="#cite_ref-pmid20851224_122-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFEdelmanCheralaStanczyk2010" class="citation journal cs1">Edelman AB, Cherala G, Stanczyk FZ (October 2010). "Metabolism and pharmacokinetics of contraceptive steroids in obese women: a review". Contraception. 82 (4): 314–23. <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.contraception.2010.04.016">10.1016/j.contraception.2010.04.016</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/20851224">20851224</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Contraception&rft.atitle=Metabolism+and+pharmacokinetics+of+contraceptive+steroids+in+obese+women%3A+a+review&rft.volume=82&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E314-%3C%2Fspan%3E23&rft.date=2010-10&rft_id=info%3Adoi%2F10.1016%2Fj.contraception.2010.04.016&rft_id=info%3Apmid%2F20851224&rft.aulast=Edelman&rft.aufirst=AB&rft.au=Cherala%2C+G&rft.au=Stanczyk%2C+FZ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid3543501-123"><a href="#cite_ref-pmid3543501_123-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRaynaudOjasoo1986" class="citation journal cs1">Raynaud JP, Ojasoo T (November 1986). "The design and use of sex-steroid antagonists". Journal of Steroid Biochemistry. 25 (5B): 811–33. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0022-4731%2886%2990313-4">10.1016/0022-4731(86)90313-4</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/3543501">3543501</a>. <q>Similar androgenic potential is inherent to norethisterone and its prodrugs (norethisterone acetate, ethynodiol diacetate, lynestrenol, norethynodrel, quingestanol [acetate]).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Steroid+Biochemistry&rft.atitle=The+design+and+use+of+sex-steroid+antagonists&rft.volume=25&rft.issue=5B&rft.pages=%3Cspan+class%3D%22nowrap%22%3E811-%3C%2Fspan%3E33&rft.date=1986-11&rft_id=info%3Adoi%2F10.1016%2F0022-4731%2886%2990313-4&rft_id=info%3Apmid%2F3543501&rft.aulast=Raynaud&rft.aufirst=JP&rft.au=Ojasoo%2C+T&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-Colton-124">^ <a href="#cite_ref-Colton_124-0">a</a> <a href="#cite_ref-Colton_124-1">b</a> Frank B. Colton, <a rel="nofollow" class="external text" href="https://patents.google.com/patent/US2655518">U.S. patent 2,655,518</a> (1952 to <a href="/wiki/G.D._Searle,_LLC" title="G.D. Searle, LLC">Searle</a> & Co). </li> <li id="cite_note-125"><a href="#cite_ref-125">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRingoldRosenkranzSondheimer1956" class="citation journal cs1">Ringold HJ, Rosenkranz G, Sondheimer F (1956). "Steroids. LXXX.11-Methyl-19-nortestosterone and 1-Methyl-17α-ethinyl-19-nortestosterone". Journal of the American Chemical Society. 78 (11): 2477–79. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1956JAChS..78.2477R">1956JAChS..78.2477R</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja01592a037">10.1021/ja01592a037</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+American+Chemical+Society&rft.atitle=Steroids.+LXXX.11-Methyl-19-nortestosterone+and+1-Methyl-17%CE%B1-ethinyl-19-nortestosterone&rft.volume=78&rft.issue=11&rft.pages=%3Cspan+class%3D%22nowrap%22%3E2477-%3C%2Fspan%3E79&rft.date=1956&rft_id=info%3Adoi%2F10.1021%2Fja01592a037&rft_id=info%3Abibcode%2F1956JAChS..78.2477R&rft.aulast=Ringold&rft.aufirst=HJ&rft.au=Rosenkranz%2C+G&rft.au=Sondheimer%2C+F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-126"><a href="#cite_ref-126">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFUeberwasserHeuslerKalvodaMeystre1963" class="citation journal cs1">Ueberwasser H, Heusler K, Kalvoda J, Meystre C, Wieland P, Anner G, et al. (1963). "19-Norsteroide II. Ein einfaches Herstellungsverfahren für 19-Norandrostan-Derivate. über Steroide, 193. Mitteilung". Helvetica Chimica Acta. 46: 344–52. <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%2Fhlca.19630460135">10.1002/hlca.19630460135</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Helvetica+Chimica+Acta&rft.atitle=19-Norsteroide+II.+Ein+einfaches+Herstellungsverfahren+f%C3%BCr+19-Norandrostan-Derivate.+%C3%BCber+Steroide%2C+193.+Mitteilung&rft.volume=46&rft.pages=%3Cspan+class%3D%22nowrap%22%3E344-%3C%2Fspan%3E52&rft.date=1963&rft_id=info%3Adoi%2F10.1002%2Fhlca.19630460135&rft.aulast=Ueberwasser&rft.aufirst=H&rft.au=Heusler%2C+K&rft.au=Kalvoda%2C+J&rft.au=Meystre%2C+C&rft.au=Wieland%2C+P&rft.au=Anner%2C+G&rft.au=Wettstein%2C+A&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-127"><a href="#cite_ref-127">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFOnkenHeublein1970" class="citation journal cs1">Onken D, Heublein D (January 1970). "[Ethinylated steroids]". Die Pharmazie. 25 (1): 3–9. <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/4914401">4914401</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Die+Pharmazie&rft.atitle=%5BEthinylated+steroids%5D&rft.volume=25&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E3-%3C%2Fspan%3E9&rft.date=1970-01&rft_id=info%3Apmid%2F4914401&rft.aulast=Onken&rft.aufirst=D&rft.au=Heublein%2C+D&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-US2744122-128"><a href="#cite_ref-US2744122_128-0">^</a> <a rel="nofollow" class="external text" href="https://patents.google.com/patent/US2744122">U.S. patent 2,744,122</a> </li> <li id="cite_note-US2774777-129"><a href="#cite_ref-US2774777_129-0">^</a> <a rel="nofollow" class="external text" href="https://patents.google.com/patent/US2774777">U.S. patent 2,774,777</a> </li> <li id="cite_note-Bullough2001-130"><a href="#cite_ref-Bullough2001_130-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBullough2001" class="citation book cs1">Bullough VL (2001). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=XuX-MGTZnJoC&pg=PA145">Encyclopedia of Birth Control</a>. ABC-CLIO. pp. 145–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-57607-181-6" title="Special:BookSources/978-1-57607-181-6"><bdi>978-1-57607-181-6</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230110231243/https://books.google.com/books?id=XuX-MGTZnJoC&pg=PA145">Archived</a> from the original on 10 January 2023. Retrieved 27 November 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Encyclopedia+of+Birth+Control&rft.pages=145-&rft.pub=ABC-CLIO&rft.date=2001&rft.isbn=978-1-57607-181-6&rft.aulast=Bullough&rft.aufirst=VL&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DXuX-MGTZnJoC%26pg%3DPA145&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-MoskowitzJennings1996-131"><a href="#cite_ref-MoskowitzJennings1996_131-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMoskowitzJennings1996" class="citation book cs1">Moskowitz EH, Jennings B (1996). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=5lf4xeSt5-AC&pg=PA40">Coerced Contraception?: Moral and Policy Challenges of Long Acting Birth Control</a>. Georgetown University Press. pp. 40–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-58901-807-5" title="Special:BookSources/978-1-58901-807-5"><bdi>978-1-58901-807-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Coerced+Contraception%3F%3A+Moral+and+Policy+Challenges+of+Long+Acting+Birth+Control&rft.pages=40-&rft.pub=Georgetown+University+Press&rft.date=1996&rft.isbn=978-1-58901-807-5&rft.aulast=Moskowitz&rft.aufirst=EH&rft.au=Jennings%2C+B&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D5lf4xeSt5-AC%26pg%3DPA40&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid20933120-132"><a href="#cite_ref-pmid20933120_132-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFNieschlag2010" class="citation journal cs1">Nieschlag E (November 2010). <a rel="nofollow" class="external text" href="http://www.kup.at/kup/pdf/10172.pdf">"Clinical trials in male hormonal contraception"</a> (PDF). Contraception. 82 (5): 457–70. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.contraception.2010.03.020">10.1016/j.contraception.2010.03.020</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/20933120">20933120</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20201205082822/https://www.kup.at/kup/pdf/10172.pdf">Archived</a> (PDF) from the original on 5 December 2020. Retrieved 28 December 2018.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Contraception&rft.atitle=Clinical+trials+in+male+hormonal+contraception&rft.volume=82&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E457-%3C%2Fspan%3E70&rft.date=2010-11&rft_id=info%3Adoi%2F10.1016%2Fj.contraception.2010.03.020&rft_id=info%3Apmid%2F20933120&rft.aulast=Nieschlag&rft.aufirst=E&rft_id=http%3A%2F%2Fwww.kup.at%2Fkup%2Fpdf%2F10172.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-NieschlagBehre2012-133"><a href="#cite_ref-NieschlagBehre2012_133-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFNieschlagBehreNieschlagBehre2012" class="citation journal cs1">Nieschlag E, Behre HM, Nieschlag E, Behre HM, Nieschlag S (2012). Nieschlag E, Behre HM, Nieschlag S (eds.). "The essential role of testosterone in hormonal male contraception". Testosterone: 470–93. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1017%2FCBO9781139003353.023">10.1017/CBO9781139003353.023</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9781139003353" title="Special:BookSources/9781139003353"><bdi>9781139003353</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Testosterone&rft.atitle=The+essential+role+of+testosterone+in+hormonal+male+contraception&rft.pages=%3Cspan+class%3D%22nowrap%22%3E470-%3C%2Fspan%3E93&rft.date=2012&rft_id=info%3Adoi%2F10.1017%2FCBO9781139003353.023&rft.isbn=9781139003353&rft.aulast=Nieschlag&rft.aufirst=E&rft.au=Behre%2C+HM&rft.au=Nieschlag%2C+E&rft.au=Behre%2C+HM&rft.au=Nieschlag%2C+S&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> <li id="cite_note-pmid6223801-134"><a href="#cite_ref-pmid6223801_134-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBenagianoPrimiero1983" class="citation journal cs1">Benagiano G, Primiero FM (June 1983). "Long acting contraceptives. Present status". Drugs. 25 (6): 570–609. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.2165%2F00003495-198325060-00003">10.2165/00003495-198325060-00003</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/6223801">6223801</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:45898359">45898359</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Drugs&rft.atitle=Long+acting+contraceptives.+Present+status&rft.volume=25&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E570-%3C%2Fspan%3E609&rft.date=1983-06&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A45898359%23id-name%3DS2CID&rft_id=info%3Apmid%2F6223801&rft_id=info%3Adoi%2F10.2165%2F00003495-198325060-00003&rft.aulast=Benagiano&rft.aufirst=G&rft.au=Primiero%2C+FM&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2>[<a href="/w/index.php?title=Norethisterone&action=edit&section=36" title="Edit section: Further reading">edit</a>]</div> <style data-mw-deduplicate="TemplateStyles:r1239549316">.mw-parser-output .refbegin{margin-bottom:0.5em}.mw-parser-output .refbegin-hanging-indents>ul{margin-left:0}.mw-parser-output .refbegin-hanging-indents>ul>li{margin-left:0;padding-left:3.2em;text-indent:-3.2em}.mw-parser-output .refbegin-hanging-indents ul,.mw-parser-output .refbegin-hanging-indents ul li{list-style:none}@media(max-width:720px){.mw-parser-output .refbegin-hanging-indents>ul>li{padding-left:1.6em;text-indent:-1.6em}}.mw-parser-output .refbegin-columns{margin-top:0.3em}.mw-parser-output .refbegin-columns ul{margin-top:0}.mw-parser-output .refbegin-columns li{page-break-inside:avoid;break-inside:avoid-column}@media screen{.mw-parser-output .refbegin{font-size:90%}}</style><div class="refbegin refbegin-columns references-column-width" style="column-width: 30em"> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBrogdenSpeightAvery1973" class="citation journal cs1">Brogden RN, Speight TM, Avery GS (1973). "Progestagen-only oral contraceptives: a preliminary report of the action and clinical use of norgestrel and norethisterone". Drugs. 6 (3): 169–81. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.2165%2F00003495-197306030-00004">10.2165/00003495-197306030-00004</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/4130566">4130566</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:42295736">42295736</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Drugs&rft.atitle=Progestagen-only+oral+contraceptives%3A+a+preliminary+report+of+the+action+and+clinical+use+of+norgestrel+and+norethisterone&rft.volume=6&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E169-%3C%2Fspan%3E81&rft.date=1973&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A42295736%23id-name%3DS2CID&rft_id=info%3Apmid%2F4130566&rft_id=info%3Adoi%2F10.2165%2F00003495-197306030-00004&rft.aulast=Brogden&rft.aufirst=RN&rft.au=Speight%2C+TM&rft.au=Avery%2C+GS&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation journal cs1">"Norethisterone and norethisterone acetate". IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. 21: 441–60. December 1979. <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/120838">120838</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=IARC+Monographs+on+the+Evaluation+of+the+Carcinogenic+Risk+of+Chemicals+to+Humans&rft.atitle=Norethisterone+and+norethisterone+acetate&rft.volume=21&rft.pages=%3Cspan+class%3D%22nowrap%22%3E441-%3C%2Fspan%3E60&rft.date=1979-12&rft_id=info%3Apmid%2F120838&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFStanczykRoy1990" class="citation journal cs1">Stanczyk FZ, Roy S (July 1990). "Metabolism of levonorgestrel, norethindrone, and structurally related contraceptive steroids". Contraception. 42 (1): 67–96. <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%2F0010-7824%2890%2990093-b">10.1016/0010-7824(90)90093-b</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/2143719">2143719</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Contraception&rft.atitle=Metabolism+of+levonorgestrel%2C+norethindrone%2C+and+structurally+related+contraceptive+steroids&rft.volume=42&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E67-%3C%2Fspan%3E96&rft.date=1990-07&rft_id=info%3Adoi%2F10.1016%2F0010-7824%2890%2990093-b&rft_id=info%3Apmid%2F2143719&rft.aulast=Stanczyk&rft.aufirst=FZ&rft.au=Roy%2C+S&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWisemanMcTavish1994" class="citation journal cs1">Wiseman LR, McTavish D (March 1994). "Transdermal estradiol/norethisterone. A review of its pharmacological properties and clinical use in postmenopausal women". Drugs & Aging. 4 (3): 238–56. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.2165%2F00002512-199404030-00006">10.2165/00002512-199404030-00006</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/8199397">8199397</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:68007924">68007924</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Drugs+%26+Aging&rft.atitle=Transdermal+estradiol%2Fnorethisterone.+A+review+of+its+pharmacological+properties+and+clinical+use+in+postmenopausal+women&rft.volume=4&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E238-%3C%2Fspan%3E56&rft.date=1994-03&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A68007924%23id-name%3DS2CID&rft_id=info%3Apmid%2F8199397&rft_id=info%3Adoi%2F10.2165%2F00002512-199404030-00006&rft.aulast=Wiseman&rft.aufirst=LR&rft.au=McTavish%2C+D&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFTaitelKafrissen1995" class="citation journal cs1">Taitel HF, Kafrissen ME (1995). "Norethindrone – a review of therapeutic applications". International Journal of Fertility and Menopausal Studies. 40 (4): 207–23. <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/8520623">8520623</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+Fertility+and+Menopausal+Studies&rft.atitle=Norethindrone+%E2%80%93+a+review+of+therapeutic+applications&rft.volume=40&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E207-%3C%2Fspan%3E23&rft.date=1995&rft_id=info%3Apmid%2F8520623&rft.aulast=Taitel&rft.aufirst=HF&rft.au=Kafrissen%2C+ME&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMaierHerman2001" class="citation journal cs1">Maier WE, Herman JR (August 2001). "Pharmacology and toxicology of ethinyl estradiol and norethindrone acetate in experimental animals". Regulatory Toxicology and Pharmacology. 34 (1): 53–61. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1006%2Frtph.2001.1483">10.1006/rtph.2001.1483</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/11502156">11502156</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Regulatory+Toxicology+and+Pharmacology&rft.atitle=Pharmacology+and+toxicology+of+ethinyl+estradiol+and+norethindrone+acetate+in+experimental+animals&rft.volume=34&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E53-%3C%2Fspan%3E61&rft.date=2001-08&rft_id=info%3Adoi%2F10.1006%2Frtph.2001.1483&rft_id=info%3Apmid%2F11502156&rft.aulast=Maier&rft.aufirst=WE&rft.au=Herman%2C+JR&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRiisLehmannChristiansen2002" class="citation journal cs1">Riis BJ, Lehmann HJ, Christiansen C (October 2002). "Norethisterone acetate in combination with estrogen: effects on the skeleton and other organs. A review". American Journal of Obstetrics and Gynecology. 187 (4): 1101–16. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1067%2Fmob.2002.122852">10.1067/mob.2002.122852</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/12389012">12389012</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=American+Journal+of+Obstetrics+and+Gynecology&rft.atitle=Norethisterone+acetate+in+combination+with+estrogen%3A+effects+on+the+skeleton+and+other+organs.+A+review&rft.volume=187&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1101-%3C%2Fspan%3E16&rft.date=2002-10&rft_id=info%3Adoi%2F10.1067%2Fmob.2002.122852&rft_id=info%3Apmid%2F12389012&rft.aulast=Riis&rft.aufirst=BJ&rft.au=Lehmann%2C+HJ&rft.au=Christiansen%2C+C&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDraperMorroniHoffmanSmit2006" class="citation journal cs1">Draper BH, Morroni C, Hoffman M, Smit J, Beksinska M, Hapgood J, et al. (July 2006). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11491191">"Depot medroxyprogesterone versus norethisterone oenanthate for long-acting progestogenic contraception"</a>. The Cochrane Database of Systematic Reviews. 2012 (3): CD005214. <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.CD005214.pub2">10.1002/14651858.CD005214.pub2</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/PMC11491191">11491191</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/16856087">16856087</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=Depot+medroxyprogesterone+versus+norethisterone+oenanthate+for+long-acting+progestogenic+contraception&rft.volume=2012&rft.issue=3&rft.pages=CD005214&rft.date=2006-07&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC11491191%23id-name%3DPMC&rft_id=info%3Apmid%2F16856087&rft_id=info%3Adoi%2F10.1002%2F14651858.CD005214.pub2&rft.aulast=Draper&rft.aufirst=BH&rft.au=Morroni%2C+C&rft.au=Hoffman%2C+M&rft.au=Smit%2C+J&rft.au=Beksinska%2C+M&rft.au=Hapgood%2C+J&rft.au=Van+der+Merwe%2C+L&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC11491191&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKuhlWiegratz2007" class="citation journal cs1">Kuhl H, Wiegratz I (August 2007). "Can 19-nortestosterone derivatives be aromatized in the liver of adult humans? Are there clinical implications?". Climacteric. 10 (4): 344–53. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F13697130701380434">10.1080/13697130701380434</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/17653961">17653961</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:20759583">20759583</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Climacteric&rft.atitle=Can+19-nortestosterone+derivatives+be+aromatized+in+the+liver+of+adult+humans%3F+Are+there+clinical+implications%3F&rft.volume=10&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E344-%3C%2Fspan%3E53&rft.date=2007-08&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A20759583%23id-name%3DS2CID&rft_id=info%3Apmid%2F17653961&rft_id=info%3Adoi%2F10.1080%2F13697130701380434&rft.aulast=Kuhl&rft.aufirst=H&rft.au=Wiegratz%2C+I&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCaseyMurray2008" class="citation journal cs1">Casey CL, Murray CA (2008). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2544373">"HT update: spotlight on estradiol/norethindrone acetate combination therapy"</a>. Clinical Interventions in Aging. 3 (1): 9–16. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.2147%2Fcia.s1663">10.2147/cia.s1663</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/PMC2544373">2544373</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/18488874">18488874</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Clinical+Interventions+in+Aging&rft.atitle=HT+update%3A+spotlight+on+estradiol%2Fnorethindrone+acetate+combination+therapy&rft.volume=3&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E9-%3C%2Fspan%3E16&rft.date=2008&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2544373%23id-name%3DPMC&rft_id=info%3Apmid%2F18488874&rft_id=info%3Adoi%2F10.2147%2Fcia.s1663&rft.aulast=Casey&rft.aufirst=CL&rft.au=Murray%2C+CA&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2544373&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPaulenCurtis2009" class="citation journal cs1">Paulen ME, Curtis KM (October 2009). "When can a woman have repeat progestogen-only injectables--depot medroxyprogesterone acetate or norethisterone enantate?". Contraception. 80 (4): 391–408. <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.contraception.2009.03.023">10.1016/j.contraception.2009.03.023</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/19751863">19751863</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Contraception&rft.atitle=When+can+a+woman+have+repeat+progestogen-only+injectables--depot+medroxyprogesterone+acetate+or+norethisterone+enantate%3F&rft.volume=80&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E391-%3C%2Fspan%3E408&rft.date=2009-10&rft_id=info%3Adoi%2F10.1016%2Fj.contraception.2009.03.023&rft_id=info%3Apmid%2F19751863&rft.aulast=Paulen&rft.aufirst=ME&rft.au=Curtis%2C+KM&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorethisterone" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFChwaliszSurreyStanczyk2012" class="citation journal cs1">Chwalisz K, Surrey E, Stanczyk FZ (June 2012). "The hormonal profile of norethindrone acetate: rationale for add-back therapy with gonadotropin-releasing hormone agonists in women with endometriosis". Reproductive Sciences. 19 (6): 563–71. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1177%2F1933719112438061">10.1177/1933719112438061</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/22457429">22457429</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:2882899">2882899</a>.</cite><span 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style="font-size:114%;margin:0 4em"><a href="/wiki/Progestogen_(medication)" title="Progestogen (medication)">Progestogens</a> and <a href="/wiki/Antiprogestogen" title="Antiprogestogen">antiprogestogens</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Progestogen_(medication)" title="Progestogen (medication)">Progestogens</a> (and <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestins</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="PRTooltip_Progesterone_receptor_agonists408" scope="row" class="navbox-group" style="width:8em;;text-align:center;"><a href="/wiki/Progesterone_receptor" title="Progesterone receptor"><abbr title="Progesterone receptor">PR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Progesterone receptor <a href="/wiki/Agonist" title="Agonist">agonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Progesterone derivatives: <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">Progesterone</a></li> <li><a href="/wiki/Quingestrone" title="Quingestrone">Quingestrone</a></li></ul> <ul><li>Retroprogesterone derivatives: <a href="/wiki/Dydrogesterone" title="Dydrogesterone">Dydrogesterone</a></li> <li><a href="/wiki/Trengestone" title="Trengestone">Trengestone</a></li></ul> <ul><li>17α-Hydroxyprogesterone (and closely related) derivatives: 17α-Hydroxylated: <a href="/wiki/Acetomepregenol" title="Acetomepregenol">Acetomepregenol (mepregenol diacetate)</a></li> <li><a href="/wiki/Algestone_acetophenide" title="Algestone acetophenide">Algestone acetophenide (dihydroxyprogesterone acetophenide)</a></li> <li><a href="/wiki/Anagestone_acetate" title="Anagestone acetate">Anagestone acetate</a></li> <li><a href="/wiki/Chlormadinone_acetate" title="Chlormadinone acetate">Chlormadinone acetate</a></li> <li><a href="/wiki/Chlormethenmadinone_acetate" title="Chlormethenmadinone acetate">Chlormethenmadinone acetate</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Delmadinone_acetate" title="Delmadinone acetate">Delmadinone acetate</a></li> <li><a href="/wiki/Flugestone_acetate" title="Flugestone acetate">Flugestone acetate (flurogestone acetate)</a></li> <li><a href="/wiki/Flumedroxone_acetate" title="Flumedroxone acetate">Flumedroxone acetate</a></li> <li><a href="/wiki/Hydroxyprogesterone_acetate" title="Hydroxyprogesterone acetate">Hydroxyprogesterone acetate</a></li> <li><a href="/wiki/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">Hydroxyprogesterone caproate</a></li> <li><a href="/wiki/Hydroxyprogesterone_heptanoate" title="Hydroxyprogesterone heptanoate">Hydroxyprogesterone heptanoate</a></li> <li><a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">Medroxyprogesterone acetate</a>#</li> <li><a href="/wiki/Megestrol_acetate" title="Megestrol acetate">Megestrol acetate</a></li> <li><a href="/wiki/Melengestrol_acetate" title="Melengestrol acetate">Melengestrol acetate</a></li> <li><a href="/wiki/Methenmadinone_acetate" title="Methenmadinone acetate">Methenmadinone acetate</a></li> <li><a href="/wiki/Osaterone_acetate" title="Osaterone acetate">Osaterone acetate</a></li> <li><a href="/wiki/Pentagestrone_acetate" title="Pentagestrone acetate">Pentagestrone acetate</a></li> <li><a href="/wiki/Proligestone" title="Proligestone">Proligestone</a>; 17α-Methylated: <a href="/wiki/Medrogestone" title="Medrogestone">Medrogestone</a>; Others: <a href="/wiki/Haloprogesterone" title="Haloprogesterone">Haloprogesterone</a></li></ul> <ul><li>19-Norprogesterone derivatives: 17α-Hydroxylated: <a href="/wiki/Gestonorone_caproate" title="Gestonorone caproate">Gestonorone caproate (gestronol hexanoate)</a></li> <li><a href="/wiki/Nomegestrol_acetate" title="Nomegestrol acetate">Nomegestrol acetate</a></li> <li><a href="/wiki/Norgestomet" title="Norgestomet">Norgestomet</a></li> <li><a href="/wiki/Segesterone_acetate" title="Segesterone acetate">Segesterone acetate (nestorone, elcometrine)</a>; 17α-Methylated: <a href="/wiki/Demegestone" title="Demegestone">Demegestone</a></li> <li><a href="/wiki/Promegestone" title="Promegestone">Promegestone</a></li> <li><a href="/wiki/Trimegestone" title="Trimegestone">Trimegestone</a></li></ul> <ul><li>Testosterone derivatives: Estranes: <a href="/wiki/Danazol" title="Danazol">Danazol</a></li> <li><a href="/wiki/Dimethisterone" title="Dimethisterone">Dimethisterone</a></li> <li><a href="/wiki/Ethisterone" title="Ethisterone">Ethisterone</a></li></ul> <ul><li>19-Nortestosterone derivatives: Estranes: <a href="/wiki/Allylestrenol" title="Allylestrenol">Allylestrenol</a></li> <li><a href="/wiki/Altrenogest" title="Altrenogest">Altrenogest</a></li> <li><a href="/wiki/Dienogest" title="Dienogest">Dienogest</a></li> <li><a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">Etynodiol diacetate</a></li> <li><a href="/wiki/Lynestrenol" title="Lynestrenol">Lynestrenol</a></li> <li><a class="mw-selflink selflink">Norethisterone (norethindrone)</a>#</li> <li><a href="/wiki/Norethisterone_acetate" title="Norethisterone acetate">Norethisterone acetate</a></li> <li><a href="/wiki/Norethisterone_enanthate" title="Norethisterone enanthate">Norethisterone enanthate</a></li> <li><a href="/wiki/Noretynodrel" title="Noretynodrel">Noretynodrel</a></li> <li><a href="/wiki/Norgesterone" title="Norgesterone">Norgesterone</a></li> <li><a href="/wiki/Norgestrienone" title="Norgestrienone">Norgestrienone</a></li> <li><a href="/wiki/Normethandrone" title="Normethandrone">Normethandrone (methylestrenolone)</a></li> <li><a href="/wiki/Norvinisterone" title="Norvinisterone">Norvinisterone</a></li> <li><a href="/wiki/Oxendolone" title="Oxendolone">Oxendolone</a></li> <li><a href="/wiki/Quingestanol_acetate" title="Quingestanol acetate">Quingestanol acetate</a></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a>; Gonanes: <a href="/wiki/Desogestrel" title="Desogestrel">Desogestrel</a></li> <li><a href="/wiki/Etonogestrel" title="Etonogestrel">Etonogestrel</a></li> <li><a href="/wiki/Gestodene" title="Gestodene">Gestodene</a></li> <li><a href="/wiki/Gestrinone" title="Gestrinone">Gestrinone</a></li> <li><a href="/wiki/Levonorgestrel" title="Levonorgestrel">Levonorgestrel</a>#</li> <li><a href="/wiki/Norelgestromin" title="Norelgestromin">Norelgestromin</a></li> <li><a href="/wiki/Norgestimate" title="Norgestimate">Norgestimate</a></li> <li><a href="/wiki/Norgestrel" title="Norgestrel">Norgestrel</a></li></ul> <ul><li>Spirolactone derivatives: <a href="/wiki/Drospirenone" title="Drospirenone">Drospirenone</a></li></ul> <ul><li>Others: <a href="/wiki/Anabolic%E2%80%93androgenic_steroid" class="mw-redirect" title="Anabolic–androgenic steroid">Anabolic–androgenic steroids</a> (e.g., <a href="/wiki/Nandrolone" title="Nandrolone">nandrolone</a> and <a href="/wiki/Nandrolone_ester" class="mw-redirect" title="Nandrolone ester">esters</a>, <a href="/wiki/Trenbolone" title="Trenbolone">trenbolone</a> and <a href="/wiki/Trenbolone_ester" class="mw-redirect" title="Trenbolone ester">esters</a>, <a href="/wiki/Ethylestrenol" title="Ethylestrenol">ethylestrenol</a>, <a href="/wiki/Norethandrolone" title="Norethandrolone">norethandrolone</a>, others)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Antiprogestogen" title="Antiprogestogen">Antiprogestogens</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8em;;text-align:center;"><a href="/wiki/Selective_progesterone_receptor_modulators" class="mw-redirect" title="Selective progesterone receptor modulators"><abbr title="Selective progesterone receptor modulators">SPRMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Selective progesterone receptor modulators</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Telapristone" title="Telapristone">Telapristone</a>§</li> <li><a href="/wiki/Ulipristal_acetate" title="Ulipristal acetate">Ulipristal acetate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8em;;text-align:center;"><a href="/wiki/Progesterone_receptor" title="Progesterone receptor"><abbr title="Progesterone receptor">PR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Progesterone receptor <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aglepristone" title="Aglepristone">Aglepristone</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td colspan="2" class="navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><div class="hlist"> <ul><li>#<a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li>‡<a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li>†<a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li>§Never to phase III</li></ul></li></ul> </div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Progesterone_receptor_modulators" title="Template:Progesterone receptor modulators">Progesterone receptor modulators</a></dd> <dd><a href="/wiki/Template:Androgens_and_antiandrogens" title="Template:Androgens and antiandrogens">Androgens and antiandrogens</a></dd> <dd><a href="/wiki/Template:Estrogens_and_antiestrogens" title="Template:Estrogens and antiestrogens">Estrogens and antiestrogens</a></dd> <dd><a href="/wiki/List_of_steroidal_progestogens" class="mw-redirect" title="List of steroidal progestogens">List of progestogens</a></dd></dl></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /></div><div role="navigation" class="navbox" aria-labelledby="Androgens_and_antiandrogens491" 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_antiandrogens491" style="font-size:114%;margin:0 4em"><a href="/wiki/Androgen" title="Androgen">Androgens</a> and <a href="/wiki/Antiandrogen" title="Antiandrogen">antiandrogens</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Androgen" title="Androgen">Androgens</a> (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 class="mw-selflink selflink">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 href="/wiki/Spironolactone" title="Spironolactone">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 href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:9em;;text-align:center;"><a href="/wiki/Antigonadotropin" title="Antigonadotropin">Antigonadotropins</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/D2_receptor" class="mw-redirect" title="D2 receptor">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="Estrogens_and_antiestrogens109" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Estrogens_and_antiestrogens" title="Template:Estrogens and antiestrogens"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Estrogens_and_antiestrogens" title="Template talk:Estrogens and antiestrogens"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Estrogens_and_antiestrogens" title="Special:EditPage/Template:Estrogens and antiestrogens"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Estrogens_and_antiestrogens109" style="font-size:114%;margin:0 4em"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogens</a> and <a href="/wiki/Antiestrogen" title="Antiestrogen">antiestrogens</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogens</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor 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/Alfatradiol" title="Alfatradiol">Alfatradiol</a></li> <li>Certain <a href="/wiki/Androgen" title="Androgen">androgens</a>/<a href="/wiki/Anabolic_steroid" title="Anabolic steroid">anabolic steroids</a> (e.g., <a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">testosterone</a>, <a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">testosterone esters</a>, <a href="/wiki/Methyltestosterone" title="Methyltestosterone">methyltestosterone</a>, <a href="/wiki/Metandienone" title="Metandienone">metandienone</a>, <a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">nandrolone esters</a>) (via estrogenic metabolites)</li> <li>Certain <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestins</a> (e.g., <a class="mw-selflink selflink">norethisterone</a>, <a href="/wiki/Noretynodrel" title="Noretynodrel">noretynodrel</a>, <a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">etynodiol diacetate</a>, <a href="/wiki/Tibolone" title="Tibolone">tibolone</a>)</li> <li><a href="/wiki/Clomestrone" title="Clomestrone">Clomestrone</a></li> <li><a href="/wiki/Cloxestradiol_acetate" title="Cloxestradiol acetate">Cloxestradiol acetate</a></li> <li><a href="/wiki/Conjugated_estriol" title="Conjugated estriol">Conjugated estriol</a></li> <li><a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a></li> <li><a href="/wiki/Epiestriol" title="Epiestriol">Epiestriol</a></li> <li><a href="/wiki/Epimestrol" title="Epimestrol">Epimestrol</a></li> <li><a href="/wiki/Esterified_estrogens" title="Esterified estrogens">Esterified estrogens</a></li> <li><a href="/wiki/Estetrol_(medication)" title="Estetrol (medication)">Estetrol</a>†</li> <li><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a></li> <li><a href="/wiki/List_of_estrogen_esters#Estradiol_esters" title="List of estrogen esters">Estradiol esters</a> (e.g., <a href="/wiki/Estradiol_acetate" title="Estradiol acetate">estradiol acetate</a>, <a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">estradiol benzoate</a>, <a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">estradiol cypionate</a>, <a href="/wiki/Estradiol_enanthate" class="mw-redirect" title="Estradiol enanthate">estradiol enanthate</a>, <a href="/wiki/Estradiol_undecylate" title="Estradiol undecylate">estradiol undecylate</a>, <a href="/wiki/Estradiol_valerate" title="Estradiol valerate">estradiol valerate</a>, <a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">polyestradiol phosphate</a>, <a href="/wiki/Estradiol_ester_mixture" class="mw-redirect" title="Estradiol ester mixture">estradiol ester mixtures</a> (<a href="/wiki/Climacteron" class="mw-redirect" title="Climacteron">Climacteron</a>))</li> <li><a href="/wiki/Estramustine_phosphate" title="Estramustine phosphate">Estramustine phosphate</a></li> <li><a href="/wiki/Estriol_(medication)" title="Estriol (medication)">Estriol</a></li> <li><a href="/wiki/List_of_estrogen_esters#Estriol_esters" title="List of estrogen esters">Estriol esters</a> (e.g., <a href="/wiki/Estriol_succinate" title="Estriol succinate">estriol succinate</a>, <a href="/wiki/Polyestriol_phosphate" title="Polyestriol phosphate">polyestriol phosphate</a>)</li> <li><a href="/wiki/Estrogenic_substances" title="Estrogenic substances">Estrogenic substances</a></li> <li><a href="/wiki/Estrone_(medication)" title="Estrone (medication)">Estrone</a></li> <li><a href="/wiki/List_of_estrogen_esters#Estrone_esters" title="List of estrogen esters">Estrone esters</a> <ul><li><a href="/wiki/Estrone_sulfate_(medication)" title="Estrone sulfate (medication)">Estrone sulfate</a></li> <li><a href="/wiki/Estropipate" title="Estropipate">Estropipate (piperazine estrone sulfate)</a></li></ul></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a># <ul><li><a href="/wiki/Ethinylestradiol_sulfonate" title="Ethinylestradiol sulfonate">Ethinylestradiol sulfonate</a></li></ul></li> <li><a href="/wiki/Hydroxyestrone_diacetate" title="Hydroxyestrone diacetate">Hydroxyestrone diacetate</a></li> <li><a href="/wiki/Mestranol" title="Mestranol">Mestranol</a></li> <li><a href="/wiki/Methylestradiol" title="Methylestradiol">Methylestradiol</a></li> <li><a href="/wiki/Moxestrol" title="Moxestrol">Moxestrol</a></li> <li><a href="/wiki/Nilestriol" title="Nilestriol">Nilestriol</a></li> <li><a href="/wiki/Prasterone" title="Prasterone">Prasterone (dehydroepiandrosterone; DHEA)</a> <ul><li><a href="/wiki/Prasterone_enanthate" title="Prasterone enanthate">Prasterone enanthate</a></li> <li><a href="/wiki/Prasterone_sulfate" title="Prasterone sulfate">Prasterone sulfate</a></li></ul></li> <li><a href="/wiki/Promestriene" title="Promestriene">Promestriene</a></li> <li><a href="/wiki/Quinestradol" title="Quinestradol">Quinestradol</a></li> <li><a href="/wiki/Quinestrol" title="Quinestrol">Quinestrol</a></li></ul> <ul><li>Nonsteroidal: <a href="/wiki/Benzestrol" title="Benzestrol">Benzestrol</a></li> <li><a href="/wiki/Bifluranol" title="Bifluranol">Bifluranol</a></li> <li><a href="/wiki/Chlorotrianisene" title="Chlorotrianisene">Chlorotrianisene</a></li> <li><a href="/wiki/Dienestrol" title="Dienestrol">Dienestrol</a> <ul><li><a href="/wiki/Dienestrol_diacetate" title="Dienestrol diacetate">Dienestrol diacetate</a></li></ul></li> <li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol (stilbestrol)</a></li> <li><a href="/wiki/List_of_estrogen_esters#Diethylstilbestrol_esters" title="List of estrogen esters">Diethylstilbestrol esters/ethers</a> <ul><li><a href="/wiki/Dimestrol" title="Dimestrol">Dimestrol (diethylstilbestrol dimethyl ether)</a></li> <li><a href="/wiki/Fosfestrol" title="Fosfestrol">Fosfestrol (diethylstilbestrol diphosphate)</a></li> <li><a href="/wiki/Mestilbol" title="Mestilbol">Mestilbol (diethylstilbestrol monomethyl ether)</a></li></ul></li> <li><a href="/wiki/Doisynoestrol" title="Doisynoestrol">Doisynoestrol (fenocycline)</a></li> <li><a href="/wiki/Hexestrol" title="Hexestrol">Hexestrol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Hexestrol_esters" title="List of estrogen esters">Hexestrol esters</a></li></ul></li> <li><a href="/wiki/Methallenestril" title="Methallenestril">Methallenestril</a></li> <li><a href="/wiki/Methestrol" title="Methestrol">Methestrol (promethestrol)</a> <ul><li><a href="/wiki/Methestrol_dipropionate" title="Methestrol dipropionate">Methestrol dipropionate (promethestrol dipropionate)</a></li></ul></li> <li><a href="/wiki/Paroxypropione" title="Paroxypropione">Paroxypropione</a></li> <li><a href="/wiki/Quadrosilan" title="Quadrosilan">Quadrosilan</a></li> <li><a href="/wiki/Triphenylbromoethylene" title="Triphenylbromoethylene">Triphenylbromoethylene</a></li> <li><a href="/wiki/Triphenylchloroethylene" title="Triphenylchloroethylene">Triphenylchloroethylene</a></li> <li><a href="/wiki/Zeranol" title="Zeranol">Zeranol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Progonadotropin" title="Progonadotropin">Progonadotropins</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Antiandrogen" title="Antiandrogen">Antiandrogens</a> (e.g., <a href="/wiki/Bicalutamide" title="Bicalutamide">bicalutamide</a>)</li> <li><a href="/wiki/GnRH_agonist" class="mw-redirect" title="GnRH agonist"><abbr title="gonadotropin-releasing hormone">GnRH</abbr> agonists</a> (e.g., <a href="/wiki/Gonadotropin-releasing_hormone" title="Gonadotropin-releasing hormone"><abbr title="gonadotropin-releasing hormone">GnRH</abbr> (gonadorelin)</a>, <a href="/wiki/Leuprorelin" title="Leuprorelin">leuprorelin</a>)</li> <li><a href="/wiki/Gonadotropin" title="Gonadotropin">Gonadotropins</a> (e.g., <a href="/wiki/Follicle-stimulating_hormone" title="Follicle-stimulating hormone"><abbr title="follicle-stimulating hormone">FSH</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip follicle-stimulating hormone, <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)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Antiestrogen" title="Antiestrogen">Antiestrogens</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor antagonists (incl. <a href="/wiki/Selective_estrogen_receptor_modulators" class="mw-redirect" title="Selective estrogen receptor modulators"><abbr title="selective estrogen receptor modulators">SERMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip selective estrogen receptor modulators/<a href="/wiki/Selective_estrogen_receptor_downregulators" class="mw-redirect" title="Selective estrogen receptor downregulators"><abbr title="selective estrogen receptor downregulators">SERDs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip selective estrogen receptor downregulators)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acolbifene" title="Acolbifene">Acolbifene</a>†</li> <li><a href="/wiki/Anordrin" title="Anordrin">Anordrin</a></li> <li><a href="/wiki/Bazedoxifene" title="Bazedoxifene">Bazedoxifene</a></li> <li><a href="/wiki/Broparestrol" title="Broparestrol">Broparestrol</a></li> <li><a href="/wiki/Clomifene" title="Clomifene">Clomifene</a>#</li> <li><a href="/wiki/Cyclofenil" title="Cyclofenil">Cyclofenil</a></li> <li><a href="/wiki/Enclomifene" title="Enclomifene">Enclomifene</a>†</li> <li><a href="/wiki/Epitiostanol" title="Epitiostanol">Epitiostanol</a></li> <li><a href="/wiki/Lasofoxifene" title="Lasofoxifene">Lasofoxifene</a></li> <li><a href="/wiki/Mepitiostane" title="Mepitiostane">Mepitiostane</a></li> <li><a href="/wiki/Ormeloxifene" title="Ormeloxifene">Ormeloxifene</a></li> <li><a href="/wiki/Ospemifene" title="Ospemifene">Ospemifene</a></li> <li><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a>#</li> <li><a href="/wiki/Toremifene" title="Toremifene">Toremifene</a></li></ul> <ul><li>Exclusively antagonistic: <a href="/wiki/Elacestrant" title="Elacestrant">Elacestrant</a></li> <li><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant</a></li></ul> <ul><li>Noncompetitive inhibitors: <a href="/wiki/Trilostane" title="Trilostane">Trilostane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Aromatase_inhibitor" title="Aromatase inhibitor">Aromatase inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li>First-generation: <a href="/wiki/Aminoglutethimide" title="Aminoglutethimide">Aminoglutethimide</a></li> <li><a href="/wiki/Testolactone" title="Testolactone">Testolactone</a></li></ul> <ul><li>Second-generation: <a href="/wiki/Fadrozole" title="Fadrozole">Fadrozole</a></li> <li><a href="/wiki/Formestane" title="Formestane">Formestane</a></li></ul> <ul><li>Third-generation: <a href="/wiki/Anastrozole" title="Anastrozole">Anastrozole</a></li> <li><a href="/wiki/Exemestane" title="Exemestane">Exemestane</a></li> <li><a href="/wiki/Letrozole" title="Letrozole">Letrozole</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Antigonadotropin" title="Antigonadotropin">Antigonadotropins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Androgen" title="Androgen">Androgens</a>/<a href="/wiki/Anabolic_steroid" title="Anabolic steroid">anabolic steroids</a> (e.g., <a href="/wiki/Testosterone" title="Testosterone">testosterone</a>, <a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">testosterone esters</a>, <a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">nandrolone esters</a>, <a href="/wiki/Oxandrolone" title="Oxandrolone">oxandrolone</a>, <a href="/wiki/Fluoxymesterone" title="Fluoxymesterone">fluoxymesterone</a>)</li> <li><a href="/wiki/D2_receptor" class="mw-redirect" title="D2 receptor">D2 receptor</a> <a href="/wiki/Dopamine_antagonist" title="Dopamine antagonist">antagonists</a> (<a href="/wiki/Prolactin" title="Prolactin">prolactin</a> releasers) (e.g., <a href="/wiki/Domperidone" title="Domperidone">domperidone</a>, <a href="/wiki/Metoclopramide" title="Metoclopramide">metoclopramide</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>, <a href="/wiki/Haloperidol" title="Haloperidol">haloperidol</a>, <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>, <a href="/wiki/Sulpiride" title="Sulpiride">sulpiride</a>)</li> <li><a href="/wiki/GnRH_agonist" class="mw-redirect" title="GnRH agonist"><abbr title="gonadotropin-releasing hormone">GnRH</abbr> agonists</a> (e.g., <a href="/wiki/Leuprorelin" title="Leuprorelin">leuprorelin</a>, <a href="/wiki/Goserelin" title="Goserelin">goserelin</a>)</li> <li><a href="/wiki/GnRH_antagonist" class="mw-redirect" title="GnRH antagonist"><abbr title="gonadotropin-releasing hormone">GnRH</abbr> antagonists</a> (e.g., <a href="/wiki/Cetrorelix" title="Cetrorelix">cetrorelix</a>, <a href="/wiki/Elagolix" title="Elagolix">elagolix</a>)</li> <li><a href="/wiki/Progestogen" title="Progestogen">Progestogens</a> (e.g., <a href="/wiki/Chlormadinone_acetate" title="Chlormadinone acetate">chlormadinone acetate</a>, <a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">cyproterone acetate</a>, <a href="/wiki/Gestonorone_caproate" title="Gestonorone caproate">gestonorone caproate</a>, <a href="/wiki/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">hydroxyprogesterone caproate</a>, <a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">medroxyprogesterone acetate</a>, <a href="/wiki/Megestrol_acetate" title="Megestrol acetate">megestrol acetate</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Mixed mechanism of action: <a href="/wiki/Danazol" title="Danazol">Danazol</a></li> <li><a href="/wiki/Gestrinone" title="Gestrinone">Gestrinone</a></li></ul> <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-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> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators">Estrogen receptor modulators</a></dd> <dd><a href="/wiki/Template:Androgens_and_antiandrogens" title="Template:Androgens and antiandrogens">Androgens and antiandrogens</a></dd> <dd><a href="/wiki/Template:Progestogens_and_antiprogestogens" title="Template:Progestogens and antiprogestogens">Progestogens and antiprogestogens</a></dd> <dd><a href="/wiki/List_of_steroidal_estrogens" class="mw-redirect" title="List of steroidal estrogens">List of estrogens</a></dd></dl></div></td></tr></tbody></table></div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Pharmacodynamics105" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2" style="background:#e8e8ff;background:#ccccff"><div id="Pharmacodynamics105" style="font-size:114%;margin:0 4em"><a href="/wiki/Pharmacodynamics" title="Pharmacodynamics">Pharmacodynamics</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;font-size:114%"><div style="padding:0px"> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Androgen_receptor_modulators801" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Androgen_receptor_modulators" title="Template:Androgen receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Androgen_receptor_modulators" title="Template talk:Androgen receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Androgen_receptor_modulators" title="Special:EditPage/Template:Androgen receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Androgen_receptor_modulators801" style="font-size:114%;margin:0 4em"><a href="/wiki/Androgen_receptor" title="Androgen receptor">Androgen receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Androgen_receptor" title="Androgen receptor"><abbr title="Androgen receptor">AR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Androgen receptor</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 class="mw-selflink selflink">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 href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/wiki/Spirorenone" title="Spirorenone">Spirorenone</a></li> <li><a href="/wiki/Spiroxasone" title="Spiroxasone">Spiroxasone</a></li> <li><a href="/wiki/Topterone" title="Topterone">Topterone</a></li> <li><a href="/wiki/Trimegestone" title="Trimegestone">Trimegestone</a></li> <li><a href="/wiki/Trimethyltrienolone" title="Trimethyltrienolone">Trimethyltrienolone (R-2956)</a></li> <li><a href="/wiki/Zanoterone" title="Zanoterone">Zanoterone</a></li></ul> <ul><li>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_modulators1222" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Estrogen_receptor_modulators" title="Template talk:Estrogen receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Estrogen_receptor_modulators" title="Special:EditPage/Template:Estrogen receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Estrogen_receptor_modulators1222" style="font-size:114%;margin:0 4em"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor">Estrogen receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor</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 class="mw-selflink selflink">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 href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/w/index.php?title=SS1010&action=edit&redlink=1" class="new" title="SS1010 (page does not exist)">SS1010</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a></li> <li><a href="/wiki/TAS-108" title="TAS-108">TAS-108 (SR-16234)</a></li> <li><a href="/wiki/Toremifene" title="Toremifene">Toremifene</a></li> <li><a href="/wiki/Trioxifene" title="Trioxifene">Trioxifene</a></li> <li><a href="/w/index.php?title=TZE-5323&action=edit&redlink=1" class="new" title="TZE-5323 (page does not exist)">TZE-5323</a></li> <li><a href="/w/index.php?title=U-11555A&action=edit&redlink=1" class="new" title="U-11555A (page does not exist)">U-11555A</a></li> <li><a href="/w/index.php?title=U-11634&action=edit&redlink=1" class="new" title="U-11634 (page does not exist)">U-11634</a></li> <li><a href="/w/index.php?title=Y-134&action=edit&redlink=1" class="new" title="Y-134 (page does not exist)">Y-134</a></li> <li><a href="/wiki/Zindoxifene" title="Zindoxifene">Zindoxifene</a></li> <li><a href="/wiki/Zuclomifene" title="Zuclomifene">Zuclomifene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/(R,R)-Tetrahydrochrysene" title="(R,R)-Tetrahydrochrysene">(R,R)-THC</a></li> <li><a href="/wiki/7%CE%B2-Hydroxy-DHEA" title="7β-Hydroxy-DHEA">7β-Hydroxy-DHEA</a></li> <li><a href="/w/index.php?title=Chloroindazole&action=edit&redlink=1" class="new" title="Chloroindazole (page does not exist)">Chloroindazole</a></li> <li><a href="/wiki/Cytestrol_acetate" title="Cytestrol acetate">Cytestrol acetate</a></li> <li><a href="/w/index.php?title=EM-800&action=edit&redlink=1" class="new" title="EM-800 (page does not exist)">EM-800 (SCH-57050)</a></li> <li><a href="/wiki/Epitiostanol" title="Epitiostanol">Epitiostanol</a></li> <li><a href="/w/index.php?title=ERA-90&action=edit&redlink=1" class="new" title="ERA-90 (page does not exist)">ERA-90</a></li> <li><a href="/w/index.php?title=ERB-88&action=edit&redlink=1" class="new" title="ERB-88 (page does not exist)">ERB-88</a></li> <li><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant (ICI-182780)</a></li> <li><a href="/wiki/Glyceollin" title="Glyceollin">Glyceollins</a> (<a href="/wiki/Glyceollin_I" title="Glyceollin I">I</a>, <a href="/w/index.php?title=Glyceollin_II&action=edit&redlink=1" class="new" title="Glyceollin II (page does not exist)">II</a>, <a href="/wiki/Glyceollin_III" title="Glyceollin III">III</a>, <a href="/w/index.php?title=Glyceollin_IV&action=edit&redlink=1" class="new" title="Glyceollin IV (page does not exist)">IV</a>)</li> <li><a href="/wiki/ICI-164384" title="ICI-164384">ICI-164384</a></li> <li><a href="/w/index.php?title=MDL-101906&action=edit&redlink=1" class="new" title="MDL-101906 (page does not exist)">MDL-101906</a></li> <li><a href="/wiki/Mepitiostane" title="Mepitiostane">Mepitiostane</a></li> <li><a href="/wiki/Methylepitiostanol" title="Methylepitiostanol">Methylepitiostanol</a></li> <li><a href="/wiki/Methylpiperidinopyrazole" title="Methylpiperidinopyrazole">Methylpiperidinopyrazole</a></li> <li><a href="/wiki/MIBE" title="MIBE">MIBE</a></li> <li><a href="/w/index.php?title=Oxabicycloheptene_sulfonate&action=edit&redlink=1" class="new" title="Oxabicycloheptene sulfonate (page does not exist)">Oxabicycloheptene sulfonate</a></li> <li><a href="/wiki/Phenytoin" title="Phenytoin">Phenytoin</a></li> <li><a href="/wiki/PHTPP" title="PHTPP">PHTPP</a></li> <li><a href="/wiki/Prochloraz" title="Prochloraz">Prochloraz</a></li> <li><a href="/w/index.php?title=RU-39411&action=edit&redlink=1" class="new" title="RU-39411 (page does not exist)">RU-39411</a></li> <li><a href="/w/index.php?title=RU-58668&action=edit&redlink=1" class="new" title="RU-58668 (page does not exist)">RU-58668</a></li> <li><a href="/w/index.php?title=SS1020&action=edit&redlink=1" class="new" title="SS1020 (page does not exist)">SS1020</a></li> <li><a href="/wiki/TAS-108" title="TAS-108">TAS-108 (SR-16234)</a></li> <li><a href="/wiki/ZB716" title="ZB716">ZB716</a></li> <li><a href="/w/index.php?title=ZK-164015&action=edit&redlink=1" class="new" title="ZK-164015 (page does not exist)">ZK-164015</a></li> <li><a href="/w/index.php?title=ZK-191703&action=edit&redlink=1" class="new" title="ZK-191703 (page does not exist)">ZK-191703</a></li></ul> <ul><li>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="/wiki/G-1_(drug)" class="mw-redirect" title="G-1 (drug)">G-1</a></li> <li><a href="/wiki/Genistein" title="Genistein">Genistein</a></li> <li><a href="/w/index.php?title=GPER-L1&action=edit&redlink=1" class="new" title="GPER-L1 (page does not exist)">GPER-L1</a></li> <li><a href="/w/index.php?title=GPER-L2&action=edit&redlink=1" class="new" title="GPER-L2 (page does not exist)">GPER-L2</a></li> <li><a href="/wiki/Hydroxytyrosol" title="Hydroxytyrosol">Hydroxytyrosol</a></li> <li><a href="/wiki/Kepone" class="mw-redirect" title="Kepone">Kepone</a></li> <li><a href="/wiki/Nicotinic_acid" title="Nicotinic acid">Nicotinic acid</a></li> <li><a href="/wiki/Nicotinamide" title="Nicotinamide">Nicotinamide</a></li> <li><a href="/wiki/Nonylphenol" title="Nonylphenol">Nonylphenol</a></li> <li><a href="/wiki/Oleuropein" title="Oleuropein">Oleuropein</a></li> <li><a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">PCBs</a> (<a href="/w/index.php?title=2,2%27,5%27-PCB-4-OH&action=edit&redlink=1" class="new" title="2,2',5'-PCB-4-OH (page does not exist)">2,2',5'-PCB-4-OH</a>)</li> <li><a href="/wiki/Propylpyrazoletriol" title="Propylpyrazoletriol">Propylpyrazoletriol</a></li> <li><a href="/wiki/Quercetin" title="Quercetin">Quercetin</a></li> <li><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></li> <li><a href="/wiki/Resveratrol" title="Resveratrol">Resveratrol</a></li> <li><a href="/w/index.php?title=STX_(drug)&action=edit&redlink=1" class="new" title="STX (drug) (page does not exist)">STX</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a></li> <li><a href="/wiki/Tectoridin" title="Tectoridin">Tectoridin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/CCL18" title="CCL18">CCL18</a></li> <li><a href="/wiki/Estriol" title="Estriol">Estriol</a></li> <li><a href="/w/index.php?title=G-15_(drug)&action=edit&redlink=1" class="new" title="G-15 (drug) (page does not exist)">G-15</a></li> <li><a href="/w/index.php?title=G-36_(drug)&action=edit&redlink=1" class="new" title="G-36 (drug) (page does not exist)">G-36</a></li> <li><a href="/wiki/MIBE" title="MIBE">MIBE</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Unknown</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a></li> <li><a href="/wiki/Zearalenone" title="Zearalenone">Zearalenone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Estrogens_and_antiestrogens" title="Template:Estrogens and antiestrogens">Estrogens and antiestrogens</a></dd> <dd><a href="/wiki/Template:Androgen_receptor_modulators" title="Template:Androgen receptor modulators">Androgen receptor modulators</a></dd> <dd><a href="/wiki/Template:Progesterone_receptor_modulators" title="Template:Progesterone receptor modulators">Progesterone receptor modulators</a></dd> <dd><a href="/wiki/List_of_steroidal_estrogens" class="mw-redirect" title="List of steroidal estrogens">List of estrogens</a></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Progesterone_receptor_modulators1654" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Progesterone_receptor_modulators" title="Template:Progesterone receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Progesterone_receptor_modulators" title="Template talk:Progesterone receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Progesterone_receptor_modulators" title="Special:EditPage/Template:Progesterone receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Progesterone_receptor_modulators1654" style="font-size:114%;margin:0 4em"><a href="/wiki/Progesterone_receptor" title="Progesterone receptor">Progesterone receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Progesterone_receptor" title="Progesterone receptor"><abbr title="Progesterone receptor">PR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Progesterone receptor</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Progesterone derivatives: <a href="/wiki/3%CE%B2-Dihydroprogesterone" title="3β-Dihydroprogesterone">3β-Dihydroprogesterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">5α-Dihydroprogesterone</a></li> <li><a href="/wiki/6%CE%B1-Methylprogesterone" title="6α-Methylprogesterone">6α-Methylprogesterone</a></li> <li><a href="/wiki/9%CE%B1-Bromo-11-ketoprogesterone" class="mw-redirect" title="9α-Bromo-11-ketoprogesterone">9α-Bromo-11-ketoprogesterone</a></li> <li><a href="/wiki/11-Dehydroprogesterone" title="11-Dehydroprogesterone">11-Dehydroprogesterone</a></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyprogesterone" title="16α-Hydroxyprogesterone">16α-Hydroxyprogesterone</a></li> <li><a href="/w/index.php?title=17%CE%B1-Methyl-11-deoxycorticosterone_acetate&action=edit&redlink=1" class="new" title="17α-Methyl-11-deoxycorticosterone acetate (page does not exist)">17α-Methyl-11-deoxycorticosterone acetate</a></li> <li><a href="/wiki/20%CE%B1-Dihydroprogesterone" title="20α-Dihydroprogesterone">20α-Dihydroprogesterone</a></li> <li><a href="/wiki/20%CE%B2-Dihydroprogesterone" title="20β-Dihydroprogesterone">20β-Dihydroprogesterone</a></li> <li><a href="/wiki/Dimepregnen" title="Dimepregnen">Dimepregnen</a></li> <li><a href="/wiki/Diosgenin" title="Diosgenin">Diosgenin</a></li> <li><a href="/wiki/P1-185" title="P1-185">P1-185</a></li> <li><a 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 class="mw-selflink selflink">Norethisterone (norethindrone)</a></li> <li><a href="/wiki/Norethisterone_ester" class="mw-redirect" title="Norethisterone ester">Norethisterone esters</a> (e.g., <a href="/wiki/Norethisterone_acetate" title="Norethisterone acetate">norethisterone acetate</a>, <a href="/wiki/Norethisterone_enanthate" title="Norethisterone enanthate">norethisterone enanthate</a>)</li> <li><a href="/wiki/Noretynodrel" title="Noretynodrel">Noretynodrel</a></li> <li><a href="/wiki/Norgesterone" title="Norgesterone">Norgesterone</a></li> <li><a href="/wiki/Norgestimate" title="Norgestimate">Norgestimate</a></li> <li><a href="/wiki/Norgestrel" title="Norgestrel">Norgestrel</a></li> <li><a href="/wiki/Norgestrienone" title="Norgestrienone">Norgestrienone</a></li> <li><a href="/wiki/Norvinisterone" title="Norvinisterone">Norvinisterone</a></li> <li><a href="/wiki/Oxendolone" title="Oxendolone">Oxendolone</a></li> <li><a href="/wiki/Quingestanol" title="Quingestanol">Quingestanol</a></li> <li><a href="/wiki/Quingestanol_acetate" title="Quingestanol acetate">Quingestanol acetate</a></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li> <li><a href="/wiki/Tigestol" title="Tigestol">Tigestol</a></li> <li><a href="/wiki/Tosagestin" title="Tosagestin">Tosagestin</a>; Anabolic–androgenic steroids: <a href="/wiki/11%CE%B2-Methyl-19-nortestosterone" title="11β-Methyl-19-nortestosterone">11β-Methyl-19-nortestosterone</a></li> <li><a href="/wiki/11%CE%B2-Methyl-19-nortestosterone_dodecylcarbonate" title="11β-Methyl-19-nortestosterone dodecylcarbonate">11β-Methyl-19-nortestosterone dodecylcarbonate</a></li> <li><a href="/wiki/19-Nor-5-androstenediol" title="19-Nor-5-androstenediol">19-Nor-5-androstenediol</a></li> <li><a href="/wiki/19-Nor-5-androstenedione" title="19-Nor-5-androstenedione">19-Nor-5-androstenedione</a></li> <li><a href="/wiki/19-Nordehydroepiandrosterone" title="19-Nordehydroepiandrosterone">19-Nordehydroepiandrosterone</a></li> <li><a href="/wiki/Bolandiol" title="Bolandiol">Bolandiol</a></li> <li><a href="/wiki/Bolandiol_dipropionate" title="Bolandiol dipropionate">Bolandiol dipropionate</a></li> <li><a href="/wiki/Bolandione" title="Bolandione">Bolandione</a></li> <li><a href="/wiki/Dimethisterone" title="Dimethisterone">Dimethisterone</a></li> <li><a href="/wiki/Dienedione" title="Dienedione">Dienedione</a></li> <li><a href="/wiki/Dienolone" title="Dienolone">Dienolone</a></li> <li><a href="/wiki/Dimethandrolone" title="Dimethandrolone">Dimethandrolone</a></li> <li><a href="/wiki/Dimethandrolone_buciclate" title="Dimethandrolone buciclate">Dimethandrolone buciclate</a></li> <li><a href="/wiki/Dimethandrolone_dodecylcarbonate" title="Dimethandrolone dodecylcarbonate">Dimethandrolone dodecylcarbonate</a></li> <li><a href="/wiki/Dimethandrolone_undecanoate" title="Dimethandrolone undecanoate">Dimethandrolone undecanoate</a></li> <li><a href="/wiki/Dimethyldienolone" title="Dimethyldienolone">Dimethyldienolone</a></li> <li><a href="/wiki/Dimethyltrienolone" title="Dimethyltrienolone">Dimethyltrienolone</a></li> <li><a href="/wiki/Ethyldienolone" title="Ethyldienolone">Ethyldienolone</a></li> <li><a href="/wiki/Ethylestrenol" title="Ethylestrenol">Ethylestrenol (ethylnandrol)</a></li> <li><a href="/wiki/Methyldienolone" title="Methyldienolone">Methyldienolone</a></li> <li><a href="/wiki/Metribolone" title="Metribolone">Metribolone (R-1881)</a></li> <li><a href="/wiki/Methoxydienone" title="Methoxydienone">Methoxydienone (methoxygonadiene)</a></li> <li><a href="/wiki/Mibolerone" title="Mibolerone">Mibolerone</a></li> <li><a href="/wiki/Nandrolone" title="Nandrolone">Nandrolone</a></li> <li><a href="/wiki/Nandrolone_ester" class="mw-redirect" title="Nandrolone ester">Nandrolone esters</a> (e.g., <a href="/wiki/Nandrolone_decanoate" title="Nandrolone decanoate">nandrolone decanoate</a>, <a href="/wiki/Nandrolone_phenylpropionate" title="Nandrolone phenylpropionate">nandrolone phenylpropionate</a>)</li> <li><a href="/wiki/Norethandrolone" title="Norethandrolone">Norethandrolone</a></li> <li><a href="/wiki/Normethandrone" title="Normethandrone">Normethandrone (methylestrenolone, normethandrolone, normethisterone)</a></li> <li><a href="/wiki/RU-2309" title="RU-2309">RU-2309</a></li> <li><a href="/wiki/Tetrahydrogestrinone" title="Tetrahydrogestrinone">Tetrahydrogestrinone</a></li> <li><a href="/wiki/Trenbolone" title="Trenbolone">Trenbolone (trienolone)</a></li> <li><a href="/wiki/Trenbolone_ester" class="mw-redirect" title="Trenbolone ester">Trenbolone esters</a> (e.g., <a href="/wiki/Trenbolone_acetate" title="Trenbolone acetate">trenbolone acetate</a>, <a href="/wiki/Trenbolone_enanthate" title="Trenbolone enanthate">trenbolone enanthate</a>)</li> <li><a href="/wiki/Trendione" title="Trendione">Trendione</a></li> <li><a href="/wiki/Trestolone" title="Trestolone">Trestolone</a></li> <li><a href="/wiki/Trestolone_acetate" title="Trestolone acetate">Trestolone acetate</a></li></ul> <ul><li>Spirolactone derivatives: <a href="/wiki/Canrenoic_acid" title="Canrenoic acid">Canrenoic acid</a></li> <li><a href="/wiki/Canrenone" title="Canrenone">Canrenone</a></li> <li><a href="/wiki/Drospirenone" title="Drospirenone">Drospirenone</a></li> <li><a href="/wiki/Mespirenone" title="Mespirenone">Mespirenone</a></li> <li><a href="/wiki/Potassium_canrenoate" title="Potassium canrenoate">Potassium canrenoate</a></li> <li><a href="/wiki/Prorenone" title="Prorenone">Prorenone</a></li> <li><a href="/wiki/SC-5233" title="SC-5233">SC-5233 (spirolactone)</a></li> <li><a href="/wiki/SC-8109" title="SC-8109">SC-8109</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/wiki/Spirorenone" title="Spirorenone">Spirorenone</a></li></ul> <ul><li>Nonsteroidal: <a href="/wiki/3,8-Dihydrodiligustilide" title="3,8-Dihydrodiligustilide">3,8-Dihydrodiligustilide</a></li> <li><a href="/wiki/LG-2527" title="LG-2527">LG-2527</a></li> <li><a href="/w/index.php?title=LG-100128&action=edit&redlink=1" class="new" title="LG-100128 (page does not exist)">LG-100128</a></li> <li><a href="/wiki/Riligustilide" title="Riligustilide">Riligustilide</a></li> <li><a href="/w/index.php?title=RWJ-26819&action=edit&redlink=1" class="new" title="RWJ-26819 (page does not exist)">RWJ-26819</a></li> <li><a href="/w/index.php?title=RWJ-49853&action=edit&redlink=1" class="new" title="RWJ-49853 (page does not exist)">RWJ-49853</a></li> <li><a href="/w/index.php?title=RWJ-60130&action=edit&redlink=1" class="new" title="RWJ-60130 (page does not exist)">RWJ-60130</a></li> <li><a href="/wiki/Tanaproget" title="Tanaproget">Tanaproget</a></li> <li><a href="/wiki/ZM-182345" title="ZM-182345">ZM-182345</a></li></ul> <ul><li>Unknown: <a href="/wiki/ORG-47241" title="ORG-47241">ORG-47241</a></li> <li><a href="/wiki/ORG-201745" title="ORG-201745">ORG-201745</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Mixed (<a href="/wiki/Selective_progesterone_receptor_modulators" class="mw-redirect" title="Selective progesterone receptor modulators"><abbr title="Selective progesterone receptor modulators">SPRMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Selective progesterone receptor modulators)</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Steroidal: <a href="/wiki/Dihydroethisterone" class="mw-redirect" title="Dihydroethisterone">Dihydroethisterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydrolevonorgestrel" title="5α-Dihydrolevonorgestrel">5α-Dihydrolevonorgestrel</a></li> <li><a href="/wiki/5%CE%B1-Dihydronorethisterone" title="5α-Dihydronorethisterone">5α-Dihydronorethisterone</a></li> <li><a href="/wiki/Asoprisnil" title="Asoprisnil">Asoprisnil</a></li> <li><a href="/wiki/Asoprisnil_ecamate" title="Asoprisnil ecamate">Asoprisnil ecamate</a></li> <li><a href="/wiki/Guggulsterone" title="Guggulsterone">Guggulsterone</a></li> <li><a href="/w/index.php?title=J1042&action=edit&redlink=1" class="new" title="J1042 (page does not exist)">J1042</a></li> <li><a href="/w/index.php?title=LG-120838&action=edit&redlink=1" class="new" title="LG-120838 (page does not exist)">LG-120838</a></li> <li><a href="/wiki/Metapristone" title="Metapristone">Metapristone (RU-42633)</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone (RU-486)</a></li> <li><a href="/w/index.php?title=ORF-9371&action=edit&redlink=1" class="new" title="ORF-9371 (page does not exist)">ORF-9371</a></li> <li><a href="/wiki/ORF-9326" class="mw-redirect" title="ORF-9326">ORF-9326</a></li> <li><a href="/w/index.php?title=ORG-31710&action=edit&redlink=1" class="new" title="ORG-31710 (page does not exist)">ORG-31710</a></li> <li><a href="/w/index.php?title=ORG-33628&action=edit&redlink=1" class="new" title="ORG-33628 (page does not exist)">ORG-33628</a></li> <li><a href="/w/index.php?title=RMI-12936&action=edit&redlink=1" class="new" title="RMI-12936 (page does not exist)">RMI-12936</a></li> <li><a href="/wiki/Telapristone" title="Telapristone">Telapristone</a></li> <li><a href="/wiki/Ulipristal_acetate" title="Ulipristal acetate">Ulipristal acetate</a></li> <li><a href="/wiki/Vilaprisan" title="Vilaprisan">Vilaprisan</a></li> <li><a href="/w/index.php?title=ZK-137316&action=edit&redlink=1" class="new" title="ZK-137316 (page does not exist)">ZK-137316</a></li></ul> <ul><li>Nonsteroidal: <a href="/wiki/Apigenin" title="Apigenin">Apigenin</a></li> <li><a href="/wiki/Kaempferol" title="Kaempferol">Kaempferol</a></li> <li><a href="/w/index.php?title=LG-120920&action=edit&redlink=1" class="new" title="LG-120920 (page does not exist)">LG-120920</a></li> <li><a href="/wiki/Naringenin" title="Naringenin">Naringenin</a></li> <li><a href="/w/index.php?title=PRA-910&action=edit&redlink=1" class="new" title="PRA-910 (page does not exist)">PRA-910</a></li> <li><a href="/wiki/Syringic_acid" title="Syringic acid">Syringic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Steroidal: <a href="/wiki/Aglepristone" title="Aglepristone">Aglepristone</a></li> <li><a href="/wiki/Lilopristone" title="Lilopristone">Lilopristone</a></li> <li><a href="/wiki/Lonaprisan" title="Lonaprisan">Lonaprisan</a></li> <li><a href="/wiki/Onapristone" title="Onapristone">Onapristone</a></li> <li><a href="/w/index.php?title=ORG-31710&action=edit&redlink=1" class="new" title="ORG-31710 (page does not exist)">ORG-31710</a></li> <li><a href="/w/index.php?title=ORG-31806&action=edit&redlink=1" class="new" title="ORG-31806 (page does not exist)">ORG-31806</a></li> <li><a href="/w/index.php?title=ORG-33628&action=edit&redlink=1" class="new" title="ORG-33628 (page does not exist)">ORG-33628</a></li> <li><a href="/w/index.php?title=RTI_3021%E2%80%93022&action=edit&redlink=1" class="new" title="RTI 3021–022 (page does not exist)">RTI 3021–022</a></li> <li><a href="/wiki/Toripristone" title="Toripristone">Toripristone</a></li> <li><a href="/wiki/Zanoterone" title="Zanoterone">Zanoterone</a></li></ul> <ul><li>Nonsteroidal: <a href="/wiki/Darolutamide" title="Darolutamide">Darolutamide</a></li> <li><a href="/w/index.php?title=LG-001447&action=edit&redlink=1" class="new" title="LG-001447 (page does not exist)">LG-001447</a></li> <li><a href="/w/index.php?title=LG-100127&action=edit&redlink=1" class="new" title="LG-100127 (page does not exist)">LG-100127</a></li> <li><a href="/w/index.php?title=LG-100128&action=edit&redlink=1" class="new" title="LG-100128 (page does not exist)">LG-100128</a></li> <li><a href="/w/index.php?title=LG-120830&action=edit&redlink=1" class="new" title="LG-120830 (page does not exist)">LG-120830</a></li> <li><a href="/w/index.php?title=LG-121046&action=edit&redlink=1" class="new" title="LG-121046 (page does not exist)">LG-121046</a></li> <li><a href="/wiki/Valproic_acid" class="mw-redirect" title="Valproic acid">Valproic acid</a></li> <li><a href="/w/index.php?title=ZM-150271&action=edit&redlink=1" class="new" title="ZM-150271 (page does not exist)">ZM-150271</a></li> <li><a href="/w/index.php?title=ZM-172406&action=edit&redlink=1" class="new" title="ZM-172406 (page does not exist)">ZM-172406</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Membrane_progesterone_receptor" title="Membrane progesterone receptor"><abbr title="Membrane progesterone receptor">mPR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Membrane progesterone receptor (<a href="/wiki/Progestin_and_adipoQ_receptor" title="Progestin and adipoQ receptor"><abbr title="Progestin and adipoQ receptor">PAQR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Progestin and adipoQ receptor)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">5α-Dihydroprogesterone</a></li> <li><a href="/wiki/5%CE%B2-Dihydroprogesterone" title="5β-Dihydroprogesterone">5β-Dihydroprogesterone</a></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycortisone (21-hydroxyprogesterone)</a></li> <li><a href="/wiki/11-Deoxycortisol" title="11-Deoxycortisol">11-Deoxycortisol (17α,21-dihydroxyprogesterone)</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone</a></li> <li><a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a></li> <li><a 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></td></tr></tbody></table></div> <style data-mw-deduplicate="TemplateStyles:r1130092004">.mw-parser-output .portal-bar{font-size:88%;font-weight:bold;display:flex;justify-content:center;align-items:baseline}.mw-parser-output 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.portal-bar-related{font-size:100%;align-items:flex-start}.mw-parser-output .portal-bar-content{display:flex;flex-flow:row wrap;align-items:center;flex:0;column-gap:1em;border-top:1px solid #a2a9b1;margin:0 auto;list-style:none}.mw-parser-output .portal-bar-content-related{border-top:none;margin:0;list-style:none}}.mw-parser-output .navbox+link+.portal-bar,.mw-parser-output .navbox+style+.portal-bar,.mw-parser-output .navbox+link+.portal-bar-bordered,.mw-parser-output .navbox+style+.portal-bar-bordered,.mw-parser-output .sister-bar+link+.portal-bar,.mw-parser-output .sister-bar+style+.portal-bar,.mw-parser-output .portal-bar+.navbox-styles+.navbox,.mw-parser-output .portal-bar+.navbox-styles+.sister-bar{margin-top:-1px}</style><div class="portal-bar noprint metadata noviewer portal-bar-bordered" role="navigation" aria-label="Portals"><a href="/wiki/Wikipedia:Contents/Portals" title="Wikipedia:Contents/Portals">Portal</a>:<ul class="portal-bar-content"><li class="portal-bar-item"><img alt="icon" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/WHO_Rod.svg/20px-WHO_Rod.svg.png" decoding="async" width="8" height="19" class="mw-file-element" data-file-width="107" data-file-height="250" /> <a href="/wiki/Portal:Medicine" title="Portal:Medicine">Medicine</a></li></ul></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Norethisterone&oldid=1282656382">https://en.wikipedia.org/w/index.php?title=Norethisterone&oldid=1282656382</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Norethisterone" 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