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id="toc-By_mouth-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Skin_patch" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Skin_patch"> <div class="vector-toc-text"> 1.4.2 Skin patch </div> </a> <ul id="toc-Skin_patch-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Intrauterine_device" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Intrauterine_device"> <div class="vector-toc-text"> 1.4.3 Intrauterine device </div> </a> <ul id="toc-Intrauterine_device-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Implant" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Implant"> <div class="vector-toc-text"> 1.4.4 Implant </div> </a> <ul id="toc-Implant-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Contraindications" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Contraindications"> <div class="vector-toc-text"> 2 Contraindications </div> </a> <ul id="toc-Contraindications-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Side_effects" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Side_effects"> <div class="vector-toc-text"> 3 Side effects </div> </a> <ul id="toc-Side_effects-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Overdose" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Overdose"> <div class="vector-toc-text"> 4 Overdose </div> </a> <ul id="toc-Overdose-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Interactions" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Interactions"> <div class="vector-toc-text"> 5 Interactions </div> </a> <ul id="toc-Interactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pharmacology" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Pharmacology"> <div class="vector-toc-text"> 6 Pharmacology </div> </a> <button aria-controls="toc-Pharmacology-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Pharmacology subsection </button> <ul id="toc-Pharmacology-sublist" class="vector-toc-list"> <li id="toc-Pharmacodynamics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmacodynamics"> <div class="vector-toc-text"> 6.1 Pharmacodynamics </div> </a> <ul id="toc-Pharmacodynamics-sublist" class="vector-toc-list"> <li id="toc-Progestogenic_activity" 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-Antigonadotropic_effects" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Antigonadotropic_effects"> <div class="vector-toc-text"> 6.1.2 Antigonadotropic effects </div> </a> <ul id="toc-Antigonadotropic_effects-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"> 6.1.3 Androgenic activity </div> </a> <ul id="toc-Androgenic_activity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_activity" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Other_activity"> <div class="vector-toc-text"> 6.1.4 Other activity </div> </a> <ul id="toc-Other_activity-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"> </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> <ul id="toc-Chemistry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> 8 History </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Society_and_culture" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Society_and_culture"> <div class="vector-toc-text"> 9 Society and culture </div> </a> <button aria-controls="toc-Society_and_culture-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Society and culture subsection </button> <ul id="toc-Society_and_culture-sublist" class="vector-toc-list"> <li id="toc-Generic_names" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Generic_names"> <div class="vector-toc-text"> 9.1 Generic names </div> </a> <ul id="toc-Generic_names-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Brand_names" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Brand_names"> <div class="vector-toc-text"> 9.2 Brand names </div> </a> <ul id="toc-Brand_names-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Availability" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Availability"> <div class="vector-toc-text"> 9.3 Availability </div> </a> <ul id="toc-Availability-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Accessibility" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Accessibility"> <div class="vector-toc-text"> 9.4 Accessibility </div> </a> <ul id="toc-Accessibility-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Research" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Research"> <div class="vector-toc-text"> 10 Research </div> </a> <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-External_links" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> 12 External links </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" > Toggle the table of contents </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading">Levonorgestrel</h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" 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Available in 28 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-28" aria-hidden="true" > 28 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%84%D9%8A%D9%81%D9%88%D9%86%D9%88%D8%B1%D8%BA%D9%8A%D8%B3%D8%AA%D8%B1%D9%8A%D9%84" title="ليفونورغيستريل – Arabic" lang="ar" hreflang="ar" data-title="ليفونورغيستريل" 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%84%D9%88%D9%88%D9%86%D9%88%D8%B1%DA%98%D8%B3%D8%AA%D8%B1%D9%88%D9%84" title="لوونورژسترول – South Azerbaijani" lang="azb" hreflang="azb" data-title="لوونورژسترول" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target">تۆرکجه</a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Levonorgestrel" title="Levonorgestrel – Catalan" lang="ca" hreflang="ca" data-title="Levonorgestrel" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target">Català</a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Levonorgestrel" title="Levonorgestrel – German" lang="de" hreflang="de" data-title="Levonorgestrel" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target">Deutsch</a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9B%CE%B5%CE%B2%CE%BF%CE%BD%CE%BF%CF%81%CE%B3%CE%B5%CF%83%CF%84%CF%81%CE%AD%CE%BB%CE%B7" title="Λεβονοργεστρέλη – Greek" lang="el" hreflang="el" data-title="Λεβονοργεστρέλη" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target">Ελληνικά</a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Levonorgestrel" title="Levonorgestrel – Spanish" lang="es" hreflang="es" data-title="Levonorgestrel" 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%84%D9%88%D9%88%D9%86%D9%88%D8%B1%DA%98%D8%B3%D8%AA%D8%B1%D9%88%D9%84" title="لوونورژسترول – Persian" lang="fa" hreflang="fa" data-title="لوونورژسترول" 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/L%C3%A9vonorgestrel" title="Lévonorgestrel – French" lang="fr" hreflang="fr" data-title="Lévonorgestrel" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target">Français</a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%A0%88%EB%B3%B4%EB%85%B8%EB%A5%B4%EA%B2%8C%EC%8A%A4%ED%8A%B8%EB%A0%90" title="레보노르게스트렐 – Korean" lang="ko" hreflang="ko" data-title="레보노르게스트렐" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target">한국어</a></li><li class="interlanguage-link interwiki-ha mw-list-item"><a href="https://ha.wikipedia.org/wiki/Levonorgestrel" title="Levonorgestrel – Hausa" lang="ha" hreflang="ha" data-title="Levonorgestrel" data-language-autonym="Hausa" data-language-local-name="Hausa" class="interlanguage-link-target">Hausa</a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Levonorgestrel" title="Levonorgestrel – Indonesian" lang="id" hreflang="id" data-title="Levonorgestrel" 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/Levonorgestrel" title="Levonorgestrel – Italian" lang="it" hreflang="it" data-title="Levonorgestrel" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target">Italiano</a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Levonorgestrel" title="Levonorgestrel – Dutch" lang="nl" hreflang="nl" data-title="Levonorgestrel" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target">Nederlands</a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%AC%E3%83%9C%E3%83%8E%E3%83%AB%E3%82%B2%E3%82%B9%E3%83%88%E3%83%AC%E3%83%AB" title="レボノルゲストレル – Japanese" lang="ja" hreflang="ja" data-title="レボノルゲストレル" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target">日本語</a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Levonorgestrel" title="Levonorgestrel – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Levonorgestrel" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target">Norsk bokmål</a></li><li class="interlanguage-link interwiki-or mw-list-item"><a href="https://or.wikipedia.org/wiki/%E0%AC%B2%E0%AD%87%E0%AC%AD%E0%AD%8B%E0%AC%A8%E0%AC%B0%E0%AC%9C%E0%AD%87%E0%AC%B8%E0%AD%8D%E0%AC%9F%E0%AD%8D%E0%AC%B0%E0%AD%87%E0%AC%B2" title="ଲେଭୋନରଜେସ୍ଟ୍ରେଲ – Odia" lang="or" hreflang="or" data-title="ଲେଭୋନରଜେସ୍ଟ୍ରେଲ" 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/Lewonorgestrel" title="Lewonorgestrel – Polish" lang="pl" hreflang="pl" data-title="Lewonorgestrel" 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/Levonorgestrel" title="Levonorgestrel – Portuguese" lang="pt" hreflang="pt" data-title="Levonorgestrel" 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%9B%D0%B5%D0%B2%D0%BE%D0%BD%D0%BE%D1%80%D0%B3%D0%B5%D1%81%D1%82%D1%80%D0%B5%D0%BB" title="Левоноргестрел – Russian" lang="ru" hreflang="ru" data-title="Левоноргестрел" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target">Русский</a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Levonorgestrel" title="Levonorgestrel – Simple English" lang="en-simple" hreflang="en-simple" data-title="Levonorgestrel" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target">Simple English</a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Levonorgestrel" title="Levonorgestrel – Serbian" lang="sr" hreflang="sr" data-title="Levonorgestrel" 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/Levonorgestrel" title="Levonorgestrel – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Levonorgestrel" 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/Levonorgestreeli" title="Levonorgestreeli – Finnish" lang="fi" hreflang="fi" data-title="Levonorgestreeli" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target">Suomi</a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Levonorgestrel" title="Levonorgestrel – Swedish" lang="sv" hreflang="sv" data-title="Levonorgestrel" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target">Svenska</a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%A5%E0%B8%B5%E0%B9%82%E0%B8%A7%E0%B8%99%E0%B8%AD%E0%B8%A3%E0%B9%8C%E0%B9%80%E0%B8%88%E0%B8%AA%E0%B9%80%E0%B8%95%E0%B8%A3%E0%B8%A5" title="ลีโวนอร์เจสเตรล – Thai" lang="th" hreflang="th" data-title="ลีโวนอร์เจสเตรล" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target">ไทย</a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Levonorgestrel" title="Levonorgestrel – Turkish" lang="tr" hreflang="tr" data-title="Levonorgestrel" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target">Türkçe</a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Levonorgestrel" title="Levonorgestrel – Vietnamese" lang="vi" hreflang="vi" data-title="Levonorgestrel" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target">Tiếng Việt</a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E5%B7%A6%E7%82%94%E8%AF%BA%E5%AD%95%E9%85%AE" title="左炔诺孕酮 – Chinese" lang="zh" hreflang="zh" data-title="左炔诺孕酮" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target">中文</a></li> </ul> <div class="after-portlet after-portlet-lang"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q416950#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul 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dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Hormonal medication used for birth control</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Medication_abortion" class="mw-redirect" title="Medication abortion">Medication abortion</a>.</div> <div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Pharmaceutical compound</div> <style data-mw-deduplicate="TemplateStyles:r1269284339">@media screen{html.skin-theme-clientpref-night .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}</style> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title">Levonorgestrel</caption><tbody><tr><td colspan="2" class="infobox-image"><a href="/wiki/File:Levonorgestrel.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7e/Levonorgestrel.svg/225px-Levonorgestrel.svg.png" decoding="async" width="225" height="164" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7e/Levonorgestrel.svg/338px-Levonorgestrel.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7e/Levonorgestrel.svg/450px-Levonorgestrel.svg.png 2x" data-file-width="512" data-file-height="374" /></a></td></tr><tr><td colspan="2" class="infobox-image"><a href="/wiki/File:Levonorgestrel_molecule_ball.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/ca/Levonorgestrel_molecule_ball.png/235px-Levonorgestrel_molecule_ball.png" decoding="async" width="235" height="177" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/ca/Levonorgestrel_molecule_ball.png/353px-Levonorgestrel_molecule_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/ca/Levonorgestrel_molecule_ball.png/470px-Levonorgestrel_molecule_ball.png 2x" data-file-width="2560" data-file-height="1923" /></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">Plan B, Plan B One-Step, others</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">LNG; LNG-EC; d-Norgestrel; d(–)-Norgestrel; D-Norgestrel; WY-5104; SH-90999; NSC-744007; 18-Methylnorethisterone; 17α-Ethynyl-18-methyl-19-nortestosterone; 17α-Ethynyl-18-methylestr-4-en-17β-ol-3-one; 13β-Ethyl-17α-hydroxy-18,19-dinorpregn-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/progestins-etonogestrel-levonorgestrel-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/a610021.html">a610021</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Pregnancy_category" title="Pregnancy category">Pregnancy category</a></th><td class="infobox-data"><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="Australia">AU</abbr>: B3<a href="#cite_note-Drugs.com_pregnancy-1">[1]</a></li> <li>Contraindicated<a href="#cite_note-Drugs.com_pregnancy-1">[1]</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>, <a href="/wiki/Transdermal_patch" title="Transdermal patch">transdermal patch</a>, <a href="/wiki/Intrauterine_device" title="Intrauterine device">intrauterine device</a>, <a href="/wiki/Subcutaneous_implant" title="Subcutaneous implant">subcutaneous implant</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)">Progestogen (medication)</a>; <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">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">G03AC03</a> (<a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=G03AC03">WHO</a>) <a href="/wiki/ATC_code_G03" title="ATC code G03">G03AD01</a> (<a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=G03AD01">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> / OTC<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></li> <li><abbr class="country-name" title="United Kingdom">UK</abbr>: <a href="/wiki/Prescription_drug" title="Prescription drug">POM</a> (Prescription only)<a href="#cite_note-6">[6]</a></li> <li><abbr class="country-name" title="United States">US</abbr>: <a href="/wiki/Prescription_drug" title="Prescription drug">℞-only</a> / OTC<a href="#cite_note-Plan_B_One-Step_FDA_label-7">[7]</a></li> <li>Rx/OTC</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">95% (range 85–100%)<a href="#cite_note-pmid16112947-8">[8]</a><a href="#cite_note-pmid8842581-9">[9]</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">98% (50% to <a href="/wiki/Human_serum_albumin" title="Human serum albumin">albumin</a>, 48% to <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)<a href="#cite_note-pmid16112947-8">[8]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_metabolism" title="Drug metabolism">Metabolism</a></th><td class="infobox-data"><a href="/wiki/Liver" title="Liver">Liver</a> (<a href="/wiki/Redox" title="Redox">reduction</a>, <a href="/wiki/Hydroxylation" title="Hydroxylation">hydroxylation</a>, <a href="/wiki/Conjugation_(biochemistry)" class="mw-redirect" title="Conjugation (biochemistry)">conjugation</a>)<a href="#cite_note-pmid16112947-8">[8]</a><a href="#cite_note-ShoupeHaseltine2012-10">[10]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Metabolite" title="Metabolite">Metabolites</a></th><td class="infobox-data">• <a href="/wiki/5%CE%B1-Dihydrolevonorgestrel" title="5α-Dihydrolevonorgestrel">5α-Dihydro-<abbr title="levonorgestrel">LNG</abbr></a><a href="#cite_note-pmid16112947-8">[8]</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">24–32 hours<a href="#cite_note-pmid16112947-8">[8]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Excretion" title="Excretion">Excretion</a></th><td class="infobox-data"><a href="/wiki/Urine" title="Urine">Urine</a>: 20–67% <a href="/wiki/Feces" title="Feces">Feces</a>: 21–34%<a href="#cite_note-ShoupeHaseltine2012-10">[10]</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)-13-ethyl-17-ethynyl-17-hydroxy-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=797-63-7">797-63-7</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/13109">13109</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=2881">2881</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/DB00367">DB00367</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.12560.html">12560</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/5W7SIA7YZW">5W7SIA7YZW</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/D00950">D00950</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:6443">CHEBI:6443</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/ChEMBL1389">ChEMBL1389</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/DTXSID3036496">DTXSID3036496</a> <a href="https://www.wikidata.org/wiki/Q416950#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/100.011.227">100.011.227</a> <a href="https://www.wikidata.org/wiki/Q416950#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">C21H28O2</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">312.453 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=CC%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">235 to 237 °C (455 to 459 °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%;">CC[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/C21H28O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23H,3,5-12H2,1H3/t16-,17+,18+,19-,20-,21-/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:WWYNJERNGUHSAO-XUDSTZEESA-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=462091161&page2=Levonorgestrel">(verify)</a></td></tr></tbody></table> Levonorgestrel is a <a href="/wiki/Hormonal_medication" class="mw-redirect" title="Hormonal medication">hormonal medication</a> which is used in a number of <a href="/wiki/Birth_control" title="Birth control">birth control</a> methods.<a href="#cite_note-Plan_B_One-Step_FDA_label-7">[7]</a><a href="#cite_note-AHFS2015-11">[11]</a> It is combined with an <a href="/wiki/Estrogen" title="Estrogen">estrogen</a> to make <a href="/wiki/Combined_oral_birth_control_pill" class="mw-redirect" title="Combined oral birth control pill">combination birth control pills</a>.<a href="#cite_note-12">[12]</a> As an <a href="/wiki/Emergency_birth_control" class="mw-redirect" title="Emergency birth control">emergency birth control</a>, sold under the brand names Plan B One-Step and Julie, among others, it is useful within 72 hours of unprotected <a href="/wiki/Sexual_intercourse" title="Sexual intercourse">sex</a>.<a href="#cite_note-Plan_B_One-Step_FDA_label-7">[7]</a><a href="#cite_note-AHFS2015-11">[11]</a><a href="#cite_note-13">[13]</a> The more time that has passed since sex, the less effective the medication becomes, and it does not work after pregnancy (<a href="/wiki/Implantation_(human_embryo)" class="mw-redirect" title="Implantation (human embryo)">implantation</a>) has occurred.<a href="#cite_note-AHFS2015-11">[11]</a> Levonorgestrel works by preventing <a href="/wiki/Ovulation" title="Ovulation">ovulation</a> or <a href="/wiki/Human_fertilization" title="Human fertilization">fertilization</a> from occurring.<a href="#cite_note-14">[14]</a> It decreases the chances of pregnancy by 57–93%.<a href="#cite_note-Gem2010-15">[15]</a> In an <a href="/wiki/Intrauterine_device" title="Intrauterine device">intrauterine device</a> (IUD), such as Mirena among others, it is effective for the long-term prevention of <a href="/wiki/Pregnancy" title="Pregnancy">pregnancy</a>.<a href="#cite_note-AHFS2015-11">[11]</a> A <a href="/wiki/Levonorgestrel-releasing_implant" title="Levonorgestrel-releasing implant">levonorgestrel-releasing implant</a> is also available in some countries.<a href="#cite_note-16">[16]</a> Common <a href="/wiki/Side_effect" title="Side effect">side effects</a> include <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/Headache" title="Headache">headaches</a>, and <a href="/wiki/Menorrhagia" class="mw-redirect" title="Menorrhagia">increased</a>, <a href="/wiki/Hypomenorrhea" title="Hypomenorrhea">decreased</a>, or <a href="/wiki/Irregular_menstrual_bleeding" class="mw-redirect" title="Irregular menstrual bleeding">irregular menstrual bleeding</a>.<a href="#cite_note-AHFS2015-11">[11]</a> When used as an emergency contraceptive, if pregnancy occurs, there is no evidence that its use <a href="/wiki/Teratogen" class="mw-redirect" title="Teratogen">harms the fetus</a>.<a href="#cite_note-AHFS2015-11">[11]</a> It is safe to use during <a href="/wiki/Breastfeeding" title="Breastfeeding">breastfeeding</a>.<a href="#cite_note-AHFS2015-11">[11]</a> Birth control that contains levonorgestrel will not change the risk of <a href="/wiki/Sexually_transmitted_infection" title="Sexually transmitted infection">sexually transmitted infections</a>.<a href="#cite_note-AHFS2015-11">[11]</a> It is a <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestin</a> and has effects similar to those of the hormone <a href="/wiki/Progesterone" title="Progesterone">progesterone</a>.<a href="#cite_note-AHFS2015-11">[11]</a> It works primarily by preventing <a href="/wiki/Ovulation" title="Ovulation">ovulation</a> and closing off the <a href="/wiki/Cervix" title="Cervix">cervix</a> to prevent the passage of <a href="/wiki/Sperm" title="Sperm">sperm</a>.<a href="#cite_note-AHFS2015-11">[11]</a> Levonorgestrel was patented in 1960 and introduced for medical use together with <a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">ethinylestradiol</a> in 1970.<a href="#cite_note-Fis2006-17">[17]</a><a href="#cite_note-Roth2014-18">[18]</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-WHO21st-19">[19]</a> It is available as a <a href="/wiki/Generic_medication" class="mw-redirect" title="Generic medication">generic medication</a>.<a href="#cite_note-Ric2014-20">[20]</a> In the United States, levonorgestrel-containing emergency contraceptives are available <a href="/wiki/Over_the_counter" class="mw-redirect" title="Over the counter">over the counter</a> (OTC) for all ages.<a href="#cite_note-21">[21]</a> In 2020, it was the 323rd most commonly prescribed medication in the United States, with more than 800 thousand prescriptions.<a href="#cite_note-22">[22]</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=Levonorgestrel&action=edit&section=1" title="Edit section: Medical uses">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Birth_control">Birth control</h3>[<a href="/w/index.php?title=Levonorgestrel&action=edit&section=2" title="Edit section: Birth control">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/Ethinylestradiol/levonorgestrel" title="Ethinylestradiol/levonorgestrel">Ethinylestradiol/levonorgestrel</a></div> At low doses, levonorgestrel is used in <a href="/wiki/Oral_contraceptive_formulations" class="mw-redirect" title="Oral contraceptive formulations">monophasic</a> and <a href="/wiki/Oral_contraceptive_formulations" class="mw-redirect" title="Oral contraceptive formulations">triphasic</a> formulations of <a href="/wiki/Combined_oral_contraceptive_pill" title="Combined oral contraceptive pill">combined oral contraceptive pills</a>, with available monophasic doses ranging from 100 to 250 μg, and triphasic doses of 50 μg, 75 μg, and 125 μg.<a href="#cite_note-Drugs.com-23">[23]</a> It is combined with the estrogen <a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">ethinylestradiol</a> in these formulations.<a href="#cite_note-Drugs.com-23">[23]</a> At very low daily dose of 30 μg, levonorgestrel is used in some <a href="/wiki/Progestogen-only_pill" title="Progestogen-only pill">progestogen-only pill</a> <a href="/wiki/Oral_contraceptive_formulations#Progestogen-only_pills" class="mw-redirect" title="Oral contraceptive formulations">formulations</a>.<a href="#cite_note-Drugs.com-23">[23]</a> Levonorgestrel is the active ingredient in a number of <a href="/wiki/Intrauterine_devices" class="mw-redirect" title="Intrauterine devices">intrauterine devices</a> including Mirena and Skyla.<a href="#cite_note-Drugs.com-23">[23]</a><a href="#cite_note-pmid26732558-24">[24]</a> It is also the active ingredient in the <a href="/wiki/Birth_control_implant" class="mw-redirect" title="Birth control implant">birth control implants</a> <a href="/wiki/Norplant" class="mw-redirect" title="Norplant">Norplant</a> and <a href="/wiki/Norplant" class="mw-redirect" title="Norplant">Jadelle</a>.<a href="#cite_note-Drugs.com-23">[23]</a><a href="#cite_note-pmid26732558-24">[24]</a> One of the more common forms of contraception that contains only levonorgestrel is an IUD. One IUD, the Mirena, is a small hollow cylinder containing levonorgestrel and polydimethylsiloxane and covered with a release rate-controlling membrane.<a href="#cite_note-Bao_Q_2018-25">[25]</a> <div class="mw-heading mw-heading3"><h3 id="Emergency_birth_control">Emergency birth control</h3>[<a href="/w/index.php?title=Levonorgestrel&action=edit&section=3" title="Edit section: Emergency birth control">edit</a>]</div> Levonorgestrel is used in <a href="/wiki/Emergency_contraceptive_pill#Emergency_contraceptive_pills" class="mw-redirect" title="Emergency contraceptive pill">emergency contraceptive pills</a> (ECPs), both in a combined <a href="/wiki/Yuzpe_regimen" title="Yuzpe regimen">Yuzpe regimen</a> which includes estrogen, and as a levonorgestrel-only method. The levonorgestrel-only method uses levonorgestrel 1.5 mg (as a single dose or as two 0.75 mg doses 12 hours apart) taken within three days of unprotected sex. One study indicated that beginning as late as 120 hours (5 days) after intercourse could be effective.[<a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)">medical citation needed</a>] However, taking more than one dose of emergency contraception does not increase the chance of pregnancy not happening. Planned Parenthood asserts "Taking the morning-after pill (also known as emergency contraception) multiple times doesn't change its effectiveness, and won't cause any long-term side effects."<a href="#cite_note-26">[26]</a> The primary mechanism of action of levonorgestrel as a progestogen-only emergency contraceptive pill is, according to <a href="/wiki/International_Federation_of_Gynecology_and_Obstetrics" class="mw-redirect" title="International Federation of Gynecology and Obstetrics">International Federation of Gynecology and Obstetrics</a> (FIGO), to prevent fertilization by inhibition of <a href="/wiki/Ovulation" title="Ovulation">ovulation</a> and thickening of cervical mucus.<a href="#cite_note-Trussell_2011-27">[27]</a><a href="#cite_note-FSRH_EC_2012-28">[28]</a><a href="#cite_note-WHO_2010-29">[29]</a><a href="#cite_note-Speroff_2011-30">[30]</a> FIGO has stated that: "review of the evidence suggests that LNG [levonorgestreol] ECPs cannot prevent implantation of a fertilized egg. Language on implantation should not be included in LNG ECP product labeling."<a href="#cite_note-Belluck_2012b-31">[31]</a><a href="#cite_note-FIGO_2011-32">[32]</a> In November 2013, the <a href="/wiki/European_Medicines_Agency" title="European Medicines Agency">European Medicines Agency</a> (EMA) approved a change to the label saying it cannot prevent implantation of a fertilized egg.<a href="#cite_note-Belluck_2013-33">[33]</a> Other studies still find the evidence to be unclear.<a href="#cite_note-34">[34]</a> While it is unlikely that emergency contraception affects implantation it is impossible to completely exclude the possibility of post-fertilization effect.<a href="#cite_note-35">[35]</a> In November 2013, the EMA also approved a change to the label for <a href="/wiki/HRA_Pharma" class="mw-redirect" title="HRA Pharma">HRA Pharma</a>'s NorLevo saying: "In clinical trials, contraceptive efficacy was reduced in women weighing 75 kg [165 pounds] or more, and levonorgestrel was not effective in women who weighed more than 80 kg [176 pounds]."<a href="#cite_note-Belluck_2013-33">[33]</a><a href="#cite_note-Glasier_2011-36">[36]</a><a href="#cite_note-Trussell_2014-37">[37]</a> In November 2013 and January 2014, the FDA and the EMA said they were reviewing whether increased weight and <a href="/wiki/Body_mass_index" title="Body mass index">body mass index</a> (BMI) reduce the efficacy of emergency contraceptives.<a href="#cite_note-Belluck_2013-33">[33]</a> An analysis of four WHO randomised clinical trials, published in January 2017, showed pregnancy rates of 1.25% (68/5428) in women with BMI under 25, 0.61% (7/1140) in women with BMI between 25 and 30, and 2.03% (6/295) in women with BMI over 30.<a href="#cite_note-38">[38]</a> These values yield an eight-fold reduction in efficacy for women with a BMI over 30 compared to women with a BMI under 25. However, emergency contraceptives remain effective regardless of BMI. <div class="mw-heading mw-heading3"><h3 id="Hormone_therapy">Hormone therapy</h3>[<a href="/w/index.php?title=Levonorgestrel&action=edit&section=4" title="Edit section: Hormone therapy">edit</a>]</div> Levonorgestrel is used in combination with an <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogen</a> in <a href="/wiki/Menopausal_hormone_therapy" class="mw-redirect" title="Menopausal hormone therapy">menopausal hormone therapy</a>.<a href="#cite_note-Drugs.com-23">[23]</a><a href="#cite_note-Kubíková2014-39">[39]</a> It is used under the brand name Klimonorm as a <a href="/wiki/Tablet_(pharmacy)" title="Tablet (pharmacy)">combined oral tablet</a> with <a href="/wiki/Estradiol_valerate" title="Estradiol valerate">estradiol valerate</a> and under the brand name Climara Pro as a <a href="/wiki/Transdermal_patch" title="Transdermal patch">combined transdermal patch</a> with <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a>.<a href="#cite_note-Drugs.com-23">[23]</a><a href="#cite_note-Kubíková2014-39">[39]</a> <div class="mw-heading mw-heading3"><h3 id="Available_forms">Available forms</h3>[<a href="/w/index.php?title=Levonorgestrel&action=edit&section=5" title="Edit section: Available forms">edit</a>]</div> As a type of emergency contraception, levonorgestrel is used after unprotected intercourse to reduce the risk of pregnancy.<a href="#cite_note-Emergency_Contraception_-_ACOG-40">[40]</a> However, it can serve different hormonal purposes in its different methods of delivery. It is available for use in a variety of forms: <div class="mw-heading mw-heading4"><h4 id="By_mouth">By mouth</h4>[<a href="/w/index.php?title=Levonorgestrel&action=edit&section=6" title="Edit section: By mouth">edit</a>]</div> Levonorgestrel can be taken by mouth as a form of emergency birth control. The typical dosage is either 1.5 mg taken once or 0.75 mg taken 12–24 hours apart.<a href="#cite_note-:0-41">[41]</a> The effectiveness in both methods is similar.<a href="#cite_note-:0-41">[41]</a> The most widely used form of oral emergency contraception is the <a href="/wiki/Progestogen-only_pill" title="Progestogen-only pill">progestin-only pill</a>, which contains a 1.5 mg dosage of levonorgestrel.<a href="#cite_note-Emergency_Contraception_-_ACOG-40">[40]</a> Levonorgestrel-only emergency contraceptive pills are reported to have an 89% effectiveness rate if taken within the recommended 72 hours after sex.<a href="#cite_note-:1-42">[42]</a> The efficacy of the drug decreases by 50% for each 12-hour delay in taking the dose after the emergency contraceptive regimen has been started.<a href="#cite_note-:1-42">[42]</a> <div class="mw-heading mw-heading4"><h4 id="Skin_patch">Skin patch</h4>[<a href="/w/index.php?title=Levonorgestrel&action=edit&section=7" title="Edit section: Skin patch">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/Estradiol/levonorgestrel" title="Estradiol/levonorgestrel">Estradiol/levonorgestrel</a></div> <a href="/wiki/Estradiol/levonorgestrel" title="Estradiol/levonorgestrel">Estradiol with levonorgestrel</a> in the form of a skin patch is used under the brand name Climara Pro for <a href="/wiki/Hormone_replacement_therapy" title="Hormone replacement therapy">hormone replacement therapy</a> in postmenstrual women, treating symptoms such as <a href="/wiki/Hot_flash" title="Hot flash">hot flashes</a> or <a href="/wiki/Osteoporosis" title="Osteoporosis">osteoporosis</a>.<a href="#cite_note-:2-43">[43]</a> The simultaneous delivery of a <a href="/wiki/Progestogen_(medication)" title="Progestogen (medication)">progestogen</a> such as levonorgestrel is necessary for the protection of the <a href="/wiki/Endometrium" title="Endometrium">endometrium</a>.<a href="#cite_note-:3-44">[44]</a><a href="#cite_note-45">[45]</a> <div class="mw-heading mw-heading4"><h4 id="Intrauterine_device">Intrauterine device</h4>[<a href="/w/index.php?title=Levonorgestrel&action=edit&section=8" title="Edit section: Intrauterine device">edit</a>]</div> The levonorgestrel intrauterine system (LNG-IUS) is a type of long-term birth control that releases the progestin into the uterine cavity.<a href="#cite_note-Jeff2005-46">[46]</a><a href="#cite_note-Bao_Q_2018-25">[25]</a> Levonorgestrel is released at a constant, gradual rate of 0.02 mg per day by the polydimethylsiloxane membrane of the device, which renders it effective for up to five years.<a href="#cite_note-Jeff2005-46">[46]</a> Because it is inserted directly into the uterus, levonorgestrel is present in the endometrium in much higher concentrations that would result from a LNG-containing oral pill; the LNG-IUS delivers 391 ng of levonorgestrel to the inner uterine region while a comparable oral contraceptive delivers only 1.35 ng.<a href="#cite_note-Jeff2005-46">[46]</a> This high level of levonorgestrel impedes the function of the endometrium, making it hostile for sperm transport, fertilization, and implantation of an ovum.<a href="#cite_note-Jeff2005-46">[46]</a> <div class="mw-heading mw-heading4"><h4 id="Implant">Implant</h4>[<a href="/w/index.php?title=Levonorgestrel&action=edit&section=9" title="Edit section: Implant">edit</a>]</div> <a href="/wiki/Subcutaneous_implant" title="Subcutaneous implant">Subcutaneous implants</a> of levonorgestrel have been marketed as <a href="/wiki/Birth_control_implant" class="mw-redirect" title="Birth control implant">birth control implants</a> under the brand names Norplant and Jadelle and are available for use in some countries.<a href="#cite_note-pmid18803473-47">[47]</a><a href="#cite_note-Drugs.com-23">[23]</a> <div class="mw-heading mw-heading2"><h2 id="Contraindications">Contraindications</h2>[<a href="/w/index.php?title=Levonorgestrel&action=edit&section=10" title="Edit section: Contraindications">edit</a>]</div> Known or suspected pregnancy is a <a href="/wiki/Contraindication" title="Contraindication">contraindication</a> of levonorgestrel as an emergency contraceptive.<a href="#cite_note-PlanB_One-Step-Label-48">[48]</a> <div class="mw-heading mw-heading2"><h2 id="Side_effects">Side effects</h2>[<a href="/w/index.php?title=Levonorgestrel&action=edit&section=11" title="Edit section: Side effects">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/Progestin#Side_effects" class="mw-redirect" title="Progestin">Progestin § Side effects</a></div> After an intake of 1.5 mg levonorgestrel in <a href="/wiki/Clinical_trial" title="Clinical trial">clinical trials</a>, very common <a href="/wiki/Side_effect" title="Side effect">side effects</a> (reported by 10% or more) included: <a href="/wiki/Urticaria" class="mw-redirect" title="Urticaria">hives</a>, <a href="/wiki/Dizziness" title="Dizziness">dizziness</a>, <a href="/wiki/Hair_loss" title="Hair loss">hair loss</a>, <a href="/wiki/Headache" title="Headache">headache</a>, <a href="/wiki/Nausea" title="Nausea">nausea</a>, <a href="/wiki/Abdominal_pain" title="Abdominal pain">abdominal pain</a>, <a href="/wiki/Uterine_pain" class="mw-redirect" title="Uterine pain">uterine pain</a>, <a href="/wiki/Delayed_menstruation" class="mw-redirect" title="Delayed menstruation">delayed menstruation</a>, <a href="/wiki/Heavy_menstruation" class="mw-redirect" title="Heavy menstruation">heavy menstruation</a>, <a href="/wiki/Uterine_bleeding" class="mw-redirect" title="Uterine bleeding">uterine bleeding</a>, and <a href="/wiki/Fatigue_(medical)" class="mw-redirect" title="Fatigue (medical)">fatigue</a>; common side effects (reported by 1% to 10%) included <a href="/wiki/Diarrhea" title="Diarrhea">diarrhea</a>, <a href="/wiki/Vomiting" title="Vomiting">vomiting</a>, and <a href="/wiki/Painful_menstruation" class="mw-redirect" title="Painful menstruation">painful menstruation</a>; these side effects usually disappeared within 48 hours.<a href="#cite_note-49">[49]</a><a href="#cite_note-pmid24708811-50">[50]</a> However, the long term side effects common with oral contraceptives such as arterial disease are lower with levonorgestrel than in combination pills.[<a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)">medical citation needed</a>] Levonorgestrel as a contraceptive <a href="/wiki/Intrauterine_device" title="Intrauterine device">intrauterine device</a> has been associated with a slightly higher risk of <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a> than with non-use in select studies.<a href="#cite_note-pmid31990981-51">[51]</a> <div class="mw-heading mw-heading2"><h2 id="Overdose">Overdose</h2>[<a href="/w/index.php?title=Levonorgestrel&action=edit&section=12" title="Edit section: Overdose">edit</a>]</div> <a href="/wiki/Overdose" class="mw-redirect" title="Overdose">Overdose</a> of levonorgestrel as an emergency contraoceptive has not been described.<a href="#cite_note-PlanB_One-Step-Label-48">[48]</a> <a href="/wiki/Nausea" title="Nausea">Nausea</a> and <a href="/wiki/Vomiting" title="Vomiting">vomiting</a> might be expected.<a href="#cite_note-PlanB_One-Step-Label-48">[48]</a> <div class="mw-heading mw-heading2"><h2 id="Interactions">Interactions</h2>[<a href="/w/index.php?title=Levonorgestrel&action=edit&section=13" title="Edit section: Interactions">edit</a>]</div> If taken together with drugs that <a href="/wiki/Enzyme_inducer" title="Enzyme inducer">induce</a> the <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a> <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> <a href="/wiki/Liver" title="Liver">liver</a> <a href="/wiki/Enzyme" title="Enzyme">enzyme</a>, levonorgestrel may be <a href="/wiki/Metabolism" title="Metabolism">metabolized</a> faster and may have lower effectiveness.<a href="#cite_note-52">[52]</a> These include, but are not limited to barbiturates, bosentan, carbamazepine, felbamate, griseofulvin, oxcarbazepine, phenytoin, rifampin, St. John's wort and topiramate.[<a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)">medical citation needed</a>] <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2>[<a href="/w/index.php?title=Levonorgestrel&action=edit&section=14" title="Edit section: Pharmacology">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Pharmacodynamics">Pharmacodynamics</h3>[<a href="/w/index.php?title=Levonorgestrel&action=edit&section=15" title="Edit section: Pharmacodynamics">edit</a>]</div> Levonorgestrel is a <a href="/wiki/Progestogen_(medication)" title="Progestogen (medication)">progestogen</a> with weak <a href="/wiki/Androgen" title="Androgen">androgenic</a> activity.<a href="#cite_note-pmid16112947-8">[8]</a> It has no other important <a href="/wiki/Hormone" title="Hormone">hormonal</a> activity, including no <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogenic</a>, <a href="/wiki/Glucocorticoid" title="Glucocorticoid">glucocorticoid</a>, or <a href="/wiki/Antimineralocorticoid" class="mw-redirect" title="Antimineralocorticoid">antimineralocorticoid</a> activity.<a href="#cite_note-pmid16112947-8">[8]</a> The lack of significant <a href="/wiki/Mineralocorticoid" title="Mineralocorticoid">mineralocorticoid</a> or antimineralocorticoid activity with levonorgestrel is in spite of it having relatively high <a href="/wiki/Affinity_(pharmacology)" class="mw-redirect" title="Affinity (pharmacology)">affinity</a> for the <a href="/wiki/Mineralocorticoid_receptor" title="Mineralocorticoid receptor">mineralocorticoid receptor</a>, which is as much as 75% of that of <a href="/wiki/Aldosterone" title="Aldosterone">aldosterone</a>.<a href="#cite_note-pmid16112947-8">[8]</a> <table class="wikitable sortable mw-collapsible mw-collapsed" style="text-align:left; margin-left:auto; margin-right:auto; border:none;"> <caption class="nowrap"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul ul{display:inline}.mw-parser-output .hlist .mw-empty-li{display:none}.mw-parser-output .hlist dt::after{content:": "}.mw-parser-output .hlist dd::after,.mw-parser-output .hlist li::after{content:" · ";font-weight:bold}.mw-parser-output .hlist dd:last-child::after,.mw-parser-output .hlist dt:last-child::after,.mw-parser-output .hlist li:last-child::after{content:none}.mw-parser-output .hlist dd dd:first-child::before,.mw-parser-output .hlist dd dt:first-child::before,.mw-parser-output .hlist dd li:first-child::before,.mw-parser-output .hlist dt dd:first-child::before,.mw-parser-output .hlist dt dt:first-child::before,.mw-parser-output .hlist dt li:first-child::before,.mw-parser-output .hlist li dd:first-child::before,.mw-parser-output .hlist li dt:first-child::before,.mw-parser-output .hlist li li:first-child::before{content:" (";font-weight:normal}.mw-parser-output .hlist dd dd:last-child::after,.mw-parser-output .hlist dd dt:last-child::after,.mw-parser-output .hlist dd li:last-child::after,.mw-parser-output .hlist dt dd:last-child::after,.mw-parser-output .hlist dt dt:last-child::after,.mw-parser-output .hlist dt li:last-child::after,.mw-parser-output .hlist li dd:last-child::after,.mw-parser-output .hlist li dt:last-child::after,.mw-parser-output .hlist li li:last-child::after{content:")";font-weight:normal}.mw-parser-output .hlist ol{counter-reset:listitem}.mw-parser-output .hlist ol>li{counter-increment:listitem}.mw-parser-output .hlist ol>li::before{content:" "counter(listitem)"\a0 "}.mw-parser-output .hlist dd ol>li:first-child::before,.mw-parser-output .hlist dt ol>li:first-child::before,.mw-parser-output .hlist li ol>li:first-child::before{content:" ("counter(listitem)"\a0 "}</style><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Relative_affinities_of_levonorgestrel_and_metabolites" title="Template:Relative affinities of levonorgestrel and metabolites"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Relative_affinities_of_levonorgestrel_and_metabolites" title="Template talk:Relative affinities of levonorgestrel and metabolites"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Relative_affinities_of_levonorgestrel_and_metabolites" title="Special:EditPage/Template:Relative affinities of levonorgestrel and metabolites"><abbr title="Edit this template">e</abbr></a></li></ul></div> Relative affinities (%) of levonorgestrel and metabolites </caption> <tbody><tr> <th>Compound</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>Levonorgestrel</td> <td>150–162</td> <td>34a, 45</td> <td>0</td> <td>1–8</td> <td>17–75</td> <td>50</td> <td>0 </td></tr> <tr> <td><a href="/wiki/5%CE%B1-Dihydrolevonorgestrel" title="5α-Dihydrolevonorgestrel">5α-Dihydrolevonorgestrel</a></td> <td>50</td> <td>38a</td> <td>0</td> <td>?</td> <td>?</td> <td>?</td> <td>? </td></tr> <tr> <td>3α,5α-Tetrahydrolevonorgestrel</td> <td>?</td> <td>?</td> <td>0.4</td> <td>?</td> <td>?</td> <td>?</td> <td>? </td></tr> <tr> <td>3β,5α-Tetrahydrolevonorgestrel</td> <td>?</td> <td>?</td> <td>2.4</td> <td>?</td> <td>?</td> <td>?</td> <td>? </td></tr> <tr class="sortbottom"> <td colspan="8" 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> (a = <a href="/wiki/Mibolerone" title="Mibolerone">mibolerone</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)"><abbr title="estradiol">E2</abbr></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"><abbr title="dexamethasone">DEXA</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 dexamethasone 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/Dihydrotestosterone" title="Dihydrotestosterone"><abbr title="dihydrotestosterone">DHT</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 dihydrotestosterone 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. 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=Levonorgestrel&action=edit&section=16" title="Edit section: Progestogenic activity">edit</a>]</div> Levonorgestrel is a <a href="/wiki/Progestogen_(medication)" title="Progestogen (medication)">progestogen</a>; that is, an <a href="/wiki/Agonist" title="Agonist">agonist</a> of the <a href="/wiki/Progesterone_receptor" title="Progesterone receptor">progesterone receptor</a> (PR), the main <a href="/wiki/Biological_target" title="Biological target">biological target</a> of the progestogen <a href="/wiki/Sex_hormone" title="Sex hormone">sex hormone</a> <a href="/wiki/Progesterone" title="Progesterone">progesterone</a>.<a href="#cite_note-pmid16112947-8">[8]</a> It has effects similar to those of the hormone <a href="/wiki/Progesterone" title="Progesterone">progesterone</a>.<a href="#cite_note-AHFS2015-11">[11]</a> As a contraceptive, it works primarily by preventing <a href="/wiki/Ovulation" title="Ovulation">ovulation</a> and closing off the <a href="/wiki/Cervix" title="Cervix">cervix</a> to prevent the passage of <a href="/wiki/Sperm" title="Sperm">sperm</a>.<a href="#cite_note-AHFS2015-11">[11]</a> The <a href="/wiki/Endometrial_transformation_dose" class="mw-redirect" title="Endometrial transformation dose">endometrial transformation dose</a> of levonorgestrel is 150 to 250 μg/day or 2.5 to 6 mg per cycle.<a href="#cite_note-pmid16112947-8">[8]</a><a href="#cite_note-pmid14670641-53">[53]</a><a href="#cite_note-KnörrKnörr-Gärtner2013-54">[54]</a><a href="#cite_note-pmid2215269-55">[55]</a> <div class="mw-heading mw-heading4"><h4 id="Antigonadotropic_effects">Antigonadotropic effects</h4>[<a href="/w/index.php?title=Levonorgestrel&action=edit&section=17" title="Edit section: Antigonadotropic effects">edit</a>]</div> Due to its progestogenic activity, levonorgestrel has <a href="/wiki/Antigonadotropic" class="mw-redirect" title="Antigonadotropic">antigonadotropic</a> effects and is able to suppress the secretion of the <a href="/wiki/Gonadotropin" title="Gonadotropin">gonadotropins</a>, <a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone">luteinizing hormone</a> and <a href="/wiki/Follicle-stimulating_hormone" title="Follicle-stimulating hormone">follicle-stimulating hormone</a>, from the <a href="/wiki/Pituitary_gland" title="Pituitary gland">pituitary gland</a>.<a href="#cite_note-pmid16112947-8">[8]</a> This in turn, results in suppression of <a href="/wiki/Gonad" title="Gonad">gonadal</a> activity, including reduction of <a href="/wiki/Fertility" title="Fertility">fertility</a> and <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> in both women and men.<a href="#cite_note-pmid16112947-8">[8]</a><a href="#cite_note-pmid20933120-56">[56]</a> The <a href="/wiki/Ovulation" title="Ovulation">ovulation</a>-inhibiting dose of levonorgestrel in <a href="/wiki/Premenopausal" class="mw-redirect" title="Premenopausal">premenopausal</a> women is 50 to 60 μg/day.<a href="#cite_note-pmid16112947-8">[8]</a><a href="#cite_note-pmid14670641-53">[53]</a><a href="#cite_note-pmid22078182-57">[57]</a> In men, levonorgestrel causes marked suppression of circulating testosterone levels secondary to its antigonadotropic effects.<a href="#cite_note-pmid12826683-58">[58]</a> In healthy young men, levonorgestrel alone at a dose of 120 to 240 μg/day orally for 2 weeks suppressed testosterone levels from ~450 ng/dL to ~248 ng/dL (–45%).<a href="#cite_note-pmid28189123-59">[59]</a> Because of its effects on testosterone levels, and due to its androgenic activity being only weak and hence insufficient for purposes of androgen replacement in males, levonorgestrel has potent functional <a href="/wiki/Antiandrogen" title="Antiandrogen">antiandrogenic</a> effects in men.<a href="#cite_note-pmid12826683-58">[58]</a> Consequently, it can produce <a href="/wiki/Adverse_effect" title="Adverse effect">adverse effects</a> like <a href="/wiki/Decreased_libido" class="mw-redirect" title="Decreased libido">decreased libido</a> and <a href="/wiki/Erectile_dysfunction" title="Erectile dysfunction">erectile dysfunction</a>, among others.<a href="#cite_note-pmid12826683-58">[58]</a> Levonorgestrel has been combined with an <a href="/wiki/Androgen" title="Androgen">androgen</a> like <a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">testosterone</a> or <a href="/wiki/Androstanolone" title="Androstanolone">dihydrotestosterone</a> when it has been studied as a <a href="/wiki/Male_hormonal_contraceptive" class="mw-redirect" title="Male hormonal contraceptive">hormonal contraceptive in men</a>.<a href="#cite_note-pmid20933120-56">[56]</a><a href="#cite_note-pmid12826683-58">[58]</a> <div class="mw-heading mw-heading4"><h4 id="Androgenic_activity">Androgenic activity</h4>[<a href="/w/index.php?title=Levonorgestrel&action=edit&section=18" title="Edit section: Androgenic activity">edit</a>]</div> Levonorgestrel is a weak agonist of the <a href="/wiki/Androgen_receptor" title="Androgen receptor">androgen receptor</a> (AR), the main biological target of the <a href="/wiki/Androgen" title="Androgen">androgen</a> sex hormone <a href="/wiki/Testosterone" title="Testosterone">testosterone</a>.<a href="#cite_note-pmid16112947-8">[8]</a> It is a weakly <a href="/wiki/Androgen" title="Androgen">androgenic</a> progestin and in women may cause androgenic <a href="/wiki/Biochemical" class="mw-redirect" title="Biochemical">biochemical</a> changes and side effects such as decreased <a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin">sex hormone-binding globulin</a> (SHBG) levels, decreased <a href="/wiki/HDL_cholesterol" class="mw-redirect" title="HDL cholesterol"><abbr title="high-density lipoprotein">HDL</abbr> cholesterol</a> levels, <a href="/wiki/Weight_gain" title="Weight gain">weight gain</a>, and <a href="/wiki/Acne" title="Acne">acne</a>.<a href="#cite_note-pmid16112947-8">[8]</a><a href="#cite_note-pmid7825629-60">[60]</a> In combination with a potent estrogen like <a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">ethinylestradiol</a> however, all contraceptives containing androgenic progestins are negligibly androgenic in practice and in fact can be used to treat <a href="/wiki/Androgen-dependent_condition" title="Androgen-dependent condition">androgen-dependent conditions</a> like acne and <a href="/wiki/Hirsutism" title="Hirsutism">hirsutism</a> in women.<a href="#cite_note-pmid7825629-60">[60]</a> This is because ethinylestradiol causes a marked increase in SHBG levels and thereby decreases levels of free and hence bioactive testosterone, acting as a functional <a href="/wiki/Antiandrogen" title="Antiandrogen">antiandrogen</a>.<a href="#cite_note-pmid7825629-60">[60]</a> Nonetheless, contraceptives containing progestins that are less androgenic increase SHBG levels to a greater extent and may be more effective for such indications.<a href="#cite_note-pmid7825629-60">[60]</a> Levonorgestrel is currently the most androgenic progestin that is used in contraceptives, and contraceptives containing levonorgestrel may be less effective for androgen-dependent conditions relative to those containing other progestins that are less androgenic.<a href="#cite_note-KnausIsaacs2012-61">[61]</a><a href="#cite_note-GolanTashjian2011-62">[62]</a><a href="#cite_note-BreastCancer1991-63">[63]</a> <div class="mw-heading mw-heading4"><h4 id="Other_activity">Other activity</h4>[<a href="/w/index.php?title=Levonorgestrel&action=edit&section=19" title="Edit section: Other activity">edit</a>]</div> Levonorgestrel 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-pmid23758160-64">[64]</a><a href="#cite_note-pmid22335423-65">[65]</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-pmid23758160-64">[64]</a><a href="#cite_note-pmid22335423-65">[65]</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-pmid31512725-66">[66]</a> <div class="mw-heading mw-heading3"><h3 id="Pharmacokinetics">Pharmacokinetics</h3>[<a href="/w/index.php?title=Levonorgestrel&action=edit&section=20" title="Edit section: Pharmacokinetics">edit</a>]</div> The <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> of levonorgestrel is approximately 95% (range 85 to 100%).<a href="#cite_note-pmid16112947-8">[8]</a><a href="#cite_note-pmid8842581-9">[9]</a> The <a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">plasma protein binding</a> of levonorgestrel is about 98%.<a href="#cite_note-pmid16112947-8">[8]</a> It is bound 50% to <a href="/wiki/Human_serum_albumin" title="Human serum albumin">albumin</a> and 48% to SHBG.<a href="#cite_note-pmid16112947-8">[8]</a> Levonorgestrel is <a href="/wiki/Metabolism" title="Metabolism">metabolized</a> in the <a href="/wiki/Liver" title="Liver">liver</a>, via <a href="/wiki/Redox" title="Redox">reduction</a>, <a href="/wiki/Hydroxylation" title="Hydroxylation">hydroxylation</a>, and <a href="/wiki/Conjugation_(biochemistry)" class="mw-redirect" title="Conjugation (biochemistry)">conjugation</a> (specifically <a href="/wiki/Glucuronidation" title="Glucuronidation">glucuronidation</a> and <a href="/wiki/Sulfation" title="Sulfation">sulfation</a>).<a href="#cite_note-pmid16112947-8">[8]</a><a href="#cite_note-ShoupeHaseltine2012-10">[10]</a> <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">Oxidation</a> occurs primarily at the C2α and C16β positions, while reduction occurs in the A ring.<a href="#cite_note-ShoupeHaseltine2012-10">[10]</a> <a href="/wiki/5%CE%B1-Dihydrolevonorgestrel" title="5α-Dihydrolevonorgestrel">5α-Dihydrolevonorgestrel</a> is produced as an <a href="/wiki/Active_metabolite" title="Active metabolite">active metabolite</a> of levonorgestrel by <a href="/wiki/5%CE%B1-reductase" class="mw-redirect" title="5α-reductase">5α-reductase</a>.<a href="#cite_note-pmid16112947-8">[8]</a> The <a href="/wiki/Elimination_half-life" class="mw-redirect" title="Elimination half-life">elimination half-life</a> of levonorgestrel is 24 to 32 hours, although values as short as 8 hours and as great as 45 hours have been reported.<a href="#cite_note-pmid16112947-8">[8]</a><a href="#cite_note-ShoupeHaseltine2012-10">[10]</a> About 20 to 67% of a single oral dose of levonorgestrel is <a href="/wiki/Elimination_(pharmacology)" title="Elimination (pharmacology)">eliminated</a> in <a href="/wiki/Urine" title="Urine">urine</a> and 21 to 34% in <a href="/wiki/Feces" title="Feces">feces</a>.<a href="#cite_note-ShoupeHaseltine2012-10">[10]</a> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2>[<a href="/w/index.php?title=Levonorgestrel&action=edit&section=21" title="Edit section: Chemistry">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/List_of_progestogens" title="List of progestogens">List of progestogens</a>, <a href="/wiki/List_of_androgens/anabolic_steroids" class="mw-redirect" title="List of androgens/anabolic steroids">List of androgens/anabolic steroids</a>, and <a href="/wiki/Norgestrel" title="Norgestrel">Norgestrel</a></div> Levonorgestrel, also known as 17α-ethynyl-18-methyl-19-nortestosterone or as 17α-ethynyl-18-methylestr-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-Elks2014-67">[67]</a><a href="#cite_note-IndexNominum2000-68">[68]</a> It is the C13β or <a href="/wiki/Dextrorotation_and_levorotation" class="mw-redirect" title="Dextrorotation and levorotation">levorotatory</a> <a href="/wiki/Stereoisomer" class="mw-redirect" title="Stereoisomer">stereoisomer</a> and <a href="/wiki/Enantiopure" class="mw-redirect" title="Enantiopure">enantiopure</a> form of <a href="/wiki/Norgestrel" title="Norgestrel">norgestrel</a>, the C13α or dextrorotatory isomer being inactive.<a href="#cite_note-AlldredgeCorelli2012-69">[69]</a><a href="#cite_note-LaverySanfilippo2012-70">[70]</a> Levonorgestrel is more specifically a derivative of <a href="/wiki/Norethisterone" title="Norethisterone">norethisterone</a> (17α-ethynyl-19-nortestosterone) and is the <a href="/wiki/Parent_compound" class="mw-redirect" title="Parent compound">parent compound</a> of the <a href="/wiki/Gonane" title="Gonane">gonane</a> (18-methylestrane or 13β-ethylgonane) subgroup of the <a href="/wiki/19-nortestosterone" class="mw-redirect" title="19-nortestosterone">19-nortestosterone</a> family of progestins.<a href="#cite_note-OffermannsRosenthal2008-71">[71]</a> Besides levonorgestrel itself, this group includes <a href="/wiki/Desogestrel" title="Desogestrel">desogestrel</a>, <a href="/wiki/Dienogest" title="Dienogest">dienogest</a>, <a href="/wiki/Etonogestrel" title="Etonogestrel">etonogestrel</a>, <a href="/wiki/Gestodene" title="Gestodene">gestodene</a>, <a href="/wiki/Norelgestromin" title="Norelgestromin">norelgestromin</a>, <a href="/wiki/Norgestimate" title="Norgestimate">norgestimate</a>, and <a href="/wiki/Norgestrel" title="Norgestrel">norgestrel</a>.<a href="#cite_note-pmid24333799-72">[72]</a> <a href="/wiki/Levonorgestrel_acetate" title="Levonorgestrel acetate">Levonorgestrel acetate</a> and <a href="/wiki/Levonorgestrel_butanoate" title="Levonorgestrel butanoate">levonorgestrel butanoate</a> are C17β <a href="/wiki/Ester" title="Ester">esters</a> of levonorgestrel.<a href="#cite_note-GWU1987-73">[73]</a><a href="#cite_note-pmid6658872-74">[74]</a> Levonorgestrel has a <a href="/wiki/Molecular_weight" class="mw-redirect" title="Molecular weight">molecular weight</a> of 312.45 g/mol and a <a href="/wiki/Partition_coefficient" title="Partition coefficient">partition coefficient</a> (log P) of 3.8.<a href="#cite_note-PubChem-75">[75]</a><a href="#cite_note-DrugBank-76">[76]</a> <div class="mw-heading mw-heading2"><h2 id="History">History</h2>[<a href="/w/index.php?title=Levonorgestrel&action=edit&section=22" title="Edit section: History">edit</a>]</div> <a href="/wiki/Norgestrel" title="Norgestrel">Norgestrel</a> (rac-13-ethyl-17α-ethynyl-19-nortestosterone), the <a href="/wiki/Racemic_mixture" title="Racemic mixture">racemic mixture</a> containing levonorgestrel and <a href="/wiki/Dextronorgestrel" class="mw-redirect" title="Dextronorgestrel">dextronorgestrel</a>, was discovered by Hughes and colleagues at <a href="/wiki/Wyeth" title="Wyeth">Wyeth</a> in 1963 via <a href="/wiki/Structural_modification" class="mw-redirect" title="Structural modification">structural modification</a> of <a href="/wiki/Norethisterone" title="Norethisterone">norethisterone</a> (17α-ethynyl-19-nortestosterone).<a href="#cite_note-Meikle1999-77">[77]</a><a href="#cite_note-SzejtliSzente2012-78">[78]</a><a href="#cite_note-FilshieGuillebaud2013-79">[79]</a><a href="#cite_note-Marks2010-80">[80]</a> It was the first progestogen to be manufactured via <a href="/wiki/Total_chemical_synthesis" class="mw-redirect" title="Total chemical synthesis">total chemical synthesis</a>.<a href="#cite_note-FilshieGuillebaud2013-79">[79]</a><a href="#cite_note-Marks2010-80">[80]</a> Norgestrel was introduced for medical use as a <a href="/wiki/Combined_birth_control_pill" class="mw-redirect" title="Combined birth control pill">combined birth control pill</a> with <a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">ethinylestradiol</a> under the brand name Eugynon in <a href="/wiki/Germany" title="Germany">Germany</a> in 1966 and under the brand name Ovral in the United States 1968, and as a <a href="/wiki/Progestogen-only_pill" title="Progestogen-only pill">progestogen-only pill</a> under the brand name Ovrette in the United States in 1973.<a href="#cite_note-Marks2010-80">[80]</a><a href="#cite_note-Pohl2004-81">[81]</a><a href="#cite_note-Ortiz-GómezSantesmases2016-82">[82]</a><a href="#cite_note-ToneWatkins2007-83">[83]</a> Following its discovery, norgestrel had been licensed by Wyeth to <a href="/wiki/Schering_AG" title="Schering AG">Schering AG</a>, which separated the racemic mixture into its two <a href="/wiki/Optical_isomer" class="mw-redirect" title="Optical isomer">optical isomers</a> and identified levonorgestrel (13β-ethyl-17α-ethynyl-19-nortestosterone) as the active component of the mixture.<a href="#cite_note-Roth2014-18">[18]</a><a href="#cite_note-FilshieGuillebaud2013-79">[79]</a><a href="#cite_note-Marks2010-80">[80]</a> Levonorgestrel was first studied in humans by 1970, and was introduced for medical use in Germany as a combined birth control pill with ethinylestradiol under the brand name Neogynon in August 1970.<a href="#cite_note-Roth2014-18">[18]</a><a href="#cite_note-Pohl2004-81">[81]</a><a href="#cite_note-Ortiz-GómezSantesmases2016-82">[82]</a><a href="#cite_note-Albach1993-84">[84]</a><a href="#cite_note-ApeloVeloso1970-85">[85]</a><a href="#cite_note-BrosensVanAssche1971-86">[86]</a> A more widely used formulation, containing lower doses of ethinylestradiol and levonorgestrel, was introduced under the brand name Microgynon by 1973.<a href="#cite_note-Drugs.com-23">[23]</a><a href="#cite_note-SchneiderSpona1974-87">[87]</a><a href="#cite_note-pmid4614952-88">[88]</a> In addition to combined formulations, levonorgestrel was introduced as a progestogen-only pill under the brand names Microlut by 1972 and Microval by 1974.<a href="#cite_note-Scharff1972-89">[89]</a><a href="#cite_note-pmid4817042-90">[90]</a> Many other formulations and brand names of levonorgestrel-containing birth control pills have also been marketed.<a href="#cite_note-Drugs.com-23">[23]</a> Levonorgestrel, taken alone in a single high dose, was first evaluated as a form of <a href="/wiki/Emergency_contraception" title="Emergency contraception">emergency contraception</a> in 1973.<a href="#cite_note-KesserüLarrañaga1973-91">[91]</a> It was the second progestin to be evaluated for such purposes, following a study of <a href="/wiki/Quingestanol_acetate" title="Quingestanol acetate">quingestanol acetate</a> in 1970.<a href="#cite_note-KesserüLarrañaga1973-91">[91]</a><a href="#cite_note-RubioBerman1970-92">[92]</a> In 1974, the <a href="/wiki/Yuzpe_regimen" title="Yuzpe regimen">Yuzpe regimen</a>, which consisted of high doses of a combined birth control pill containing ethinylestradiol and norgestrel, was described as a method of emergency contraception by <a href="/wiki/A._Albert_Yuzpe" title="A. Albert Yuzpe">A. Albert Yuzpe</a> and colleagues, and saw widespread interest.<a href="#cite_note-Balaji2009-93">[93]</a><a href="#cite_note-pmid4844513-94">[94]</a> Levonorgestrel-only emergency contraception was introduced under the brand name Postinor by 1978.<a href="#cite_note-Farkas1978-95">[95]</a> Ho and Kwan published the first study comparing levonorgestrel only and the Yuzpe regimen as methods of emergency contraception in 1993 and found that they had similar effectiveness but that levonorgestrel alone was better-tolerated.<a href="#cite_note-ArtiniGenazzani2001-96">[96]</a><a href="#cite_note-pmid8473453-97">[97]</a> In relation to this, the Yuzpe regimen has largely been replaced as a method of emergency contraception by levonorgrestrel-only preparations.<a href="#cite_note-King2013-98">[98]</a> Levonorgestrel-only emergency contraception was approved in the United States under the brand name Plan B in 1999, and has also been marketed widely elsewhere throughout the world under other brand names such as Levonelle and NorLevo in addition to Postinor.<a href="#cite_note-Drugs.com-23">[23]</a><a href="#cite_note-Harrison-Woolrych2015-99">[99]</a> In 2013, the <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> approved Plan B One-Step for sale <a href="/wiki/Over-the-counter" class="mw-redirect" title="Over-the-counter">over-the-counter</a> in the United States without a prescription or age restriction.<a href="#cite_note-CBSNews2013-100">[100]</a> Levonorgestrel has also been introduced for use as a <a href="/wiki/Progestogen-only_intrauterine_device" class="mw-redirect" title="Progestogen-only intrauterine device">progestogen-only intrauterine device</a> under the brand names Mirena and Skyla among others, as a <a href="/wiki/Progestogen-only_birth_control_implant" class="mw-redirect" title="Progestogen-only birth control implant">progestogen-only birth control implant</a> under the brand names Norplant and Jadelle, as a <a href="/wiki/Tablet_(pharmacy)" title="Tablet (pharmacy)">combined oral tablet</a> with <a href="/wiki/Estradiol_valerate" title="Estradiol valerate">estradiol valerate</a> for <a href="/wiki/Menopausal_hormone_therapy" class="mw-redirect" title="Menopausal hormone therapy">menopausal hormone therapy</a> under the brand name Klimonorm, and as a <a href="/wiki/Transdermal_patch" title="Transdermal patch">combined transdermal patch</a> with <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a> for menopausal hormone therapy under the brand name Climara Pro.<a href="#cite_note-Drugs.com-23">[23]</a><a href="#cite_note-pmid26732558-24">[24]</a><a href="#cite_note-Kubíková2014-39">[39]</a> <a href="/wiki/Ester" title="Ester">Ester</a> <a href="/wiki/Prodrug" title="Prodrug">prodrugs</a> of levonorgestrel such as <a href="/wiki/Levonorgestrel_acetate" title="Levonorgestrel acetate">levonorgestrel acetate</a> and <a href="/wiki/Levonorgestrel_butanoate" title="Levonorgestrel butanoate">levonorgestrel butanoate</a> have been developed and studied as other forms of birth control such as long-acting <a href="/wiki/Injectable_contraceptive" class="mw-redirect" title="Injectable contraceptive">progestogen-only injectable contraceptives</a> and <a href="/wiki/Contraceptive_vaginal_ring" title="Contraceptive vaginal ring">contraceptive vaginal rings</a>, but have not been marketed for medical use.<a href="#cite_note-GWU1987-73">[73]</a><a href="#cite_note-pmid6658872-74">[74]</a> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2>[<a href="/w/index.php?title=Levonorgestrel&action=edit&section=23" 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=Levonorgestrel&action=edit&section=24" title="Edit section: Generic names">edit</a>]</div> Levonorgestrel is the <a href="/wiki/Generic_term" class="mw-redirect" title="Generic term">generic name</a> of the drug and its <a href="/wiki/International_Nonproprietary_Name" class="mw-redirect" title="International Nonproprietary Name"><abbr title="International Nonproprietary Name">INN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip International Nonproprietary Name, <a href="/wiki/United_States_Adopted_Name" title="United States Adopted Name"><abbr title="United States Adopted Name">USAN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip United States Adopted Name, <a href="/wiki/United_States_Pharmacopeia" title="United States Pharmacopeia"><abbr title="United States Pharmacopeia">USP</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip United States Pharmacopeia, <a href="/wiki/British_Approved_Name" title="British Approved Name"><abbr title="British Approved Name">BAN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip British Approved Name, <a href="/wiki/Denominazione_Comune_Italiana" title="Denominazione Comune Italiana"><abbr title="Denominazione Comune Italiana">DCIT</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Denominazione Comune Italiana, and <a href="/wiki/Japanese_Accepted_Name" title="Japanese Accepted Name"><abbr title="Japanese Accepted Name">JAN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Japanese Accepted Name, while lévonorgestrel is its <a href="/wiki/D%C3%A9nomination_Commune_Fran%C3%A7aise" title="Dénomination Commune Française"><abbr title="Dénomination Commune Française">DCF</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Dénomination Commune Française.<a href="#cite_note-Drugs.com-23">[23]</a><a href="#cite_note-Elks2014-67">[67]</a><a href="#cite_note-IndexNominum2000-68">[68]</a> It is also known as d-norgestrel, d(–)-norgestrel, or D-norgestrel, as well as by its developmental code names WY-5104 (<a href="/wiki/Wyeth" title="Wyeth">Wyeth</a>) and SH-90999 (<a href="/wiki/Schering_AG" title="Schering AG">Schering AG</a>).<a href="#cite_note-Drugs.com-23">[23]</a><a href="#cite_note-Elks2014-67">[67]</a><a href="#cite_note-IndexNominum2000-68">[68]</a><a href="#cite_note-Scharff1972-89">[89]</a> <div class="mw-heading mw-heading3"><h3 id="Brand_names">Brand names</h3>[<a href="/w/index.php?title=Levonorgestrel&action=edit&section=25" title="Edit section: Brand names">edit</a>]</div> Levonorgestrel is marketed alone or in combination with an <a href="/wiki/Estrogen" title="Estrogen">estrogen</a> (specifically <a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">ethinylestradiol</a>, <a href="/wiki/Estradiol" title="Estradiol">estradiol</a>, or <a href="/wiki/Estradiol_valerate" title="Estradiol valerate">estradiol valerate</a>) under a multitude of brand names throughout the world, including Alesse, Altavera, Alysena, Amethia, Amethyst, Ashlyna, Aviane, Camrese, Chateal, Climara Pro, Cycle 21, Daysee, Emerres, Enpresse, Erlibelle, Escapelle, Falmina, Introvale, Isteranda, Jadelle, Jaydess, Jolessa, Klimonorm, Kurvelo, Kyleena, Lessina, Levlen, Levodonna, Levonelle, Levonest, Levosert, Levora, Liletta, Loette, Logynon, LoSeasonique, Lutera, Lybrel, Marlissa, Microgynon, Microlut, Microvlar, Min-Ovral, Miranova, Mirena, My Way, Myzilra, Next Choice, Nordette, Norgeston, NorLevo, Norplant, One Pill, Option 2, Orsythia, Ovima, Ovranette, Plan B, Plan B One-Step, Portia, Postinor, Postinor-2, Preventeza, Ramonna, <a href="/wiki/Rigevidon" class="mw-redirect" title="Rigevidon">Rigevidon</a>, Quartette, Quasense, Seasonale, Seasonique, Skyla, Sronyx, Tri-Levlen, Trinordiol, Triphasil, Triquilar, Tri-Regol, Trivora, and Upostelle, among many others.<a href="#cite_note-Drugs.com-23">[23]</a><a href="#cite_note-IndexNominum2000-68">[68]</a><a href="#cite_note-Princeton2017-101">[101]</a> These formulations are used as emergency contraceptives, normal contraceptives, or in menopausal hormone therapy for the treatment of menopausal symptoms.[<a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)">medical citation needed</a>] As an emergency contraceptive, levonorgestrel is often referred to colloquially as the "morning-after pill".<a href="#cite_note-OatsAbraham2011-102">[102]</a><a href="#cite_note-CarlsonEisenstat2004-103">[103]</a> <div class="mw-heading mw-heading3"><h3 id="Availability">Availability</h3>[<a href="/w/index.php?title=Levonorgestrel&action=edit&section=26" title="Edit section: Availability">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> Levonorgestrel is very widely marketed throughout the world and is available in almost every country.<a href="#cite_note-Drugs.com-23">[23]</a><a href="#cite_note-IndexNominum2000-68">[68]</a> <div class="mw-heading mw-heading3"><h3 id="Accessibility">Accessibility</h3>[<a href="/w/index.php?title=Levonorgestrel&action=edit&section=27" title="Edit section: Accessibility">edit</a>]</div> Levonorgestrel-containing emergency contraception is available <a href="/wiki/Over-the-counter" class="mw-redirect" title="Over-the-counter">over-the-counter</a> in some countries, such as the United States.<a href="#cite_note-CBSNews2013-100">[100]</a> On some college campuses, Plan B is available from vending machines.<a href="#cite_note-104">[104]</a> A policy update in 2015, required all pharmacies, clinics, and emergency departments run by <a href="/wiki/Indian_Health_Services" class="mw-redirect" title="Indian Health Services">Indian Health Services</a> (for Native Americans) to have Plan B One-Step in stock, to distribute it to any woman (or her representative) who asked for it without a prescription, age verification, registration or any other requirement, to provide orientation training to all staff regarding the medication, to provide unbiased and medically accurate information about emergency contraception, and to make someone available at all times to distribute the pill in case the primary staffer objected to providing it on religious or moral grounds.<a href="#cite_note-105">[105]</a> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2>[<a href="/w/index.php?title=Levonorgestrel&action=edit&section=28" title="Edit section: Research">edit</a>]</div> Levonorgestrel has been studied in combination with <a href="/wiki/Androgen" title="Androgen">androgens</a> such as <a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">testosterone</a> and <a href="/wiki/Androstanolone" title="Androstanolone">dihydrotestosterone</a> as a <a href="/wiki/Male_hormonal_contraceptive" class="mw-redirect" title="Male hormonal contraceptive">hormonal contraceptive for men</a>.<a href="#cite_note-pmid20933120-56">[56]</a><a href="#cite_note-pmid12826683-58">[58]</a> <div class="mw-heading mw-heading2"><h2 id="References">References</h2>[<a href="/w/index.php?title=Levonorgestrel&action=edit&section=29" title="Edit section: References">edit</a>]</div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-Drugs.com_pregnancy-1">^ <a href="#cite_ref-Drugs.com_pregnancy_1-0">a</a> <a href="#cite_ref-Drugs.com_pregnancy_1-1">b</a> <style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output 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Retrieved 5 August 2020.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Analogue-based+Drug+Discovery&rft.pages=479&rft.pub=John+Wiley+%26+Sons&rft.date=2006&rft.isbn=9783527607495&rft.aulast=Fischer&rft.aufirst=J&rft.au=Ganellin%2C+CR&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DFjKfqkaKkAAC%26pg%3DPA479&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-Roth2014-18">^ <a href="#cite_ref-Roth2014_18-0">a</a> <a href="#cite_ref-Roth2014_18-1">b</a> <a href="#cite_ref-Roth2014_18-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRoth2014" class="citation book cs1">Roth K (2014). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=FsKpBAAAQBAJ&pg=PA77">Chemische Leckerbissen</a>. John Wiley & Sons. pp. 77–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-527-33739-2" title="Special:BookSources/978-3-527-33739-2"><bdi>978-3-527-33739-2</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210828143152/https://books.google.com/books?id=FsKpBAAAQBAJ&pg=PA77">Archived</a> from the original on 28 August 2021. Retrieved 18 April 2018. <q>[Levonorgestrel (24): The product generated by Smith's norgestrel total synthesis was a racemate, so half of each consisted of the left- and the right-handed enantiomer. Chemists at Schering discovered that only the levorotatory enantiomer was effective [49] and developed a biotechnological process for the preparation of the pure levorotatory enantiomer. This was the active ingredient levonorgestrel born. With the single-acting enantiomer, the dose and thus the liver burden could be halved again. The resulting Neogynon® contained 0.25 mg levonorgestrel and 0.05 mg ethinylestradiol and was introduced in 1970.]</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Chemische+Leckerbissen&rft.pages=77-&rft.pub=John+Wiley+%26+Sons&rft.date=2014&rft.isbn=978-3-527-33739-2&rft.aulast=Roth&rft.aufirst=K&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DFsKpBAAAQBAJ%26pg%3DPA77&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-WHO21st-19"><a href="#cite_ref-WHO21st_19-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWorld_Health_Organization2019" class="citation book cs1"><a href="/wiki/World_Health_Organization" title="World Health Organization">World Health Organization</a> (2019). World Health Organization model list of essential medicines: 21st list 2019. 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%2F325771">10665/325771</a>. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=World+Health+Organization+model+list+of+essential+medicines%3A+21st+list+2019&rft.place=Geneva&rft.pub=World+Health+Organization&rft.date=2019&rft_id=info%3Ahdl%2F10665%2F325771&rft.au=World+Health+Organization&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-Ric2014-20"><a href="#cite_ref-Ric2014_20-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHamilton2014" class="citation book cs1">Hamilton RJ (2014). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=BwqEAgAAQBAJ&pg=PA310">Tarascon pocket pharmacopoeia : 2014 deluxe lab-pocket edition</a> (15th ed.). Sudbury: Jones & Bartlett Learning. pp. 310–312. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9781284053999" title="Special:BookSources/9781284053999"><bdi>9781284053999</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20150926022049/https://books.google.ca/books?id=BwqEAgAAQBAJ&pg=PA310">Archived</a> from the original on 26 September 2015.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Tarascon+pocket+pharmacopoeia+%3A+2014+deluxe+lab-pocket+edition&rft.place=Sudbury&rft.pages=%3Cspan+class%3D%22nowrap%22%3E310-%3C%2Fspan%3E312&rft.edition=15th&rft.pub=Jones+%26+Bartlett+Learning&rft.date=2014&rft.isbn=9781284053999&rft.aulast=Hamilton&rft.aufirst=RJ&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DBwqEAgAAQBAJ%26pg%3DPA310&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-21"><a href="#cite_ref-21">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation pressrelease cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20160114114254/https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm358082.htm">"FDA approves Plan B One-Step emergency contraceptive for use without a prescription for all women of child-bearing potential"</a> (Press release). 20 June 2013. Archived from <a rel="nofollow" class="external text" href="https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm358082.htm">the original</a> on 14 January 2016. Retrieved 2 February 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=FDA+approves+Plan+B+One-Step+emergency+contraceptive+for+use+without+a+prescription+for+all+women+of+child-bearing+potential&rft.date=2013-06-20&rft_id=https%3A%2F%2Fwww.fda.gov%2FNewsEvents%2FNewsroom%2FPressAnnouncements%2Fucm358082.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-22"><a href="#cite_ref-22">^</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/Levonorgestrel">"Levonorgestrel - Drug Usage Statistics"</a>. ClinCalc. Retrieved 7 October 2022.</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=Levonorgestrel+-+Drug+Usage+Statistics&rft_id=https%3A%2F%2Fclincalc.com%2FDrugStats%2FDrugs%2FLevonorgestrel&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-Drugs.com-23">^ <a href="#cite_ref-Drugs.com_23-0">a</a> <a href="#cite_ref-Drugs.com_23-1">b</a> <a href="#cite_ref-Drugs.com_23-2">c</a> <a href="#cite_ref-Drugs.com_23-3">d</a> <a href="#cite_ref-Drugs.com_23-4">e</a> <a href="#cite_ref-Drugs.com_23-5">f</a> <a href="#cite_ref-Drugs.com_23-6">g</a> <a href="#cite_ref-Drugs.com_23-7">h</a> <a href="#cite_ref-Drugs.com_23-8">i</a> <a href="#cite_ref-Drugs.com_23-9">j</a> <a href="#cite_ref-Drugs.com_23-10">k</a> <a href="#cite_ref-Drugs.com_23-11">l</a> <a href="#cite_ref-Drugs.com_23-12">m</a> <a href="#cite_ref-Drugs.com_23-13">n</a> <a href="#cite_ref-Drugs.com_23-14">o</a> <a href="#cite_ref-Drugs.com_23-15">p</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/levonorgestrel.html">"Levonorgestrel"</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170803221748/https://www.drugs.com/international/levonorgestrel.html">Archived</a> from the original on 3 August 2017. Retrieved 3 August 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Levonorgestrel&rft_id=https%3A%2F%2Fwww.drugs.com%2Finternational%2Flevonorgestrel.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-pmid26732558-24">^ <a href="#cite_ref-pmid26732558_24-0">a</a> <a href="#cite_ref-pmid26732558_24-1">b</a> <a href="#cite_ref-pmid26732558_24-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFriend2016" class="citation journal cs1">Friend DR (October 2016). "Development of controlled release systems over the past 50 years in the area of contraception". Journal of Controlled Release. 240: 235–241. <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.jconrel.2015.12.043">10.1016/j.jconrel.2015.12.043</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/26732558">26732558</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+Controlled+Release&rft.atitle=Development+of+controlled+release+systems+over+the+past+50+years+in+the+area+of+contraception&rft.volume=240&rft.pages=%3Cspan+class%3D%22nowrap%22%3E235-%3C%2Fspan%3E241&rft.date=2016-10&rft_id=info%3Adoi%2F10.1016%2Fj.jconrel.2015.12.043&rft_id=info%3Apmid%2F26732558&rft.aulast=Friend&rft.aufirst=DR&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-Bao_Q_2018-25">^ <a href="#cite_ref-Bao_Q_2018_25-0">a</a> <a href="#cite_ref-Bao_Q_2018_25-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBaoGuPriceZou2018" class="citation journal cs1">Bao Q, Gu B, Price CF, Zou Y, Wang Y, Kozak D, et al. (October 2018). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6622171">"Manufacturing and characterization of long-acting levonorgestrel intrauterine systems"</a>. International Journal of Pharmaceutics. 550 (1–2): 447–454. <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.ijpharm.2018.09.004">10.1016/j.ijpharm.2018.09.004</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/PMC6622171">6622171</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/30195080">30195080</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+Pharmaceutics&rft.atitle=Manufacturing+and+characterization+of+long-acting+levonorgestrel+intrauterine+systems&rft.volume=550&rft.issue=%3Cspan+class%3D%22nowrap%22%3E1%E2%80%93%3C%2Fspan%3E2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E447-%3C%2Fspan%3E454&rft.date=2018-10&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6622171%23id-name%3DPMC&rft_id=info%3Apmid%2F30195080&rft_id=info%3Adoi%2F10.1016%2Fj.ijpharm.2018.09.004&rft.aulast=Bao&rft.aufirst=Q&rft.au=Gu%2C+B&rft.au=Price%2C+CF&rft.au=Zou%2C+Y&rft.au=Wang%2C+Y&rft.au=Kozak%2C+D&rft.au=Choi%2C+S&rft.au=Burgess%2C+DJ&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6622171&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-26"><a href="#cite_ref-26">^</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.plannedparenthood.org/learn/ask-experts/how-often-can-you-take-the-morning-after-pill">"How often can you take the morning-after pill?"</a>. www.plannedparenthood.org. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20220624164100/https://www.plannedparenthood.org/learn/ask-experts/how-often-can-you-take-the-morning-after-pill">Archived</a> from the original on 24 June 2022. Retrieved 18 June 2022.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=www.plannedparenthood.org&rft.atitle=How+often+can+you+take+the+morning-after+pill%3F&rft_id=https%3A%2F%2Fwww.plannedparenthood.org%2Flearn%2Fask-experts%2Fhow-often-can-you-take-the-morning-after-pill&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-Trussell_2011-27"><a href="#cite_ref-Trussell_2011_27-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFTrussellSchwarz2011" class="citation book cs1">Trussell J, Schwarz EB (2011). "Emergency contraception". In Hatcher RA, Trussell J, Nelson AL, Cates Jr W, Kowal D, Policar MS (eds.). Contraceptive technology (20th revised ed.). New York: Ardent Media. pp. 113–145. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-59708-004-0" title="Special:BookSources/978-1-59708-004-0"><bdi>978-1-59708-004-0</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/0091-9721">0091-9721</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/781956734">781956734</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Emergency+contraception&rft.btitle=Contraceptive+technology&rft.place=New+York&rft.pages=%3Cspan+class%3D%22nowrap%22%3E113-%3C%2Fspan%3E145&rft.edition=20th+revised&rft.pub=Ardent+Media&rft.date=2011&rft_id=info%3Aoclcnum%2F781956734&rft.issn=0091-9721&rft.isbn=978-1-59708-004-0&rft.aulast=Trussell&rft.aufirst=J&rft.au=Schwarz%2C+EB&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"><code class="cs1-code">{{<a href="/wiki/Template:Cite_book" title="Template:Cite book">cite book</a>}}</code>: CS1 maint: overridden setting (<a href="/wiki/Category:CS1_maint:_overridden_setting" title="Category:CS1 maint: overridden setting">link</a>) p. 121:<blockquote>Mechanism of action Copper-releasing IUCs When used as a regular or emergency method of contraception, copper-releasing IUCs act primarily to prevent fertilization. Emergency insertion of a copper IUC is significantly more effective than the use of ECPs, reducing the risk of pregnancy following unprotected intercourse by more than 99%.2,3 This very high level of effectiveness implies that emergency insertion of a copper IUC must prevent some pregnancies after fertilization. Emergency contraceptive pills To make an informed choice, women must know that ECPs—like the birth control pill, patch, ring, shot, and implant,76 and even like breastfeeding77—prevent pregnancy primarily by delaying or inhibiting ovulation and inhibiting fertilization, but may at times inhibit implantation of a fertilized egg in the endometrium. However, women should also be informed that the best available evidence indicates that ECPs prevent pregnancy by mechanisms that do not involve interference with post-fertilization events. ECPs do not cause abortion78 or harm an established pregnancy. Pregnancy begins with implantation according to medical authorities such as the US FDA, the National Institutes of Health79 and the American College of Obstetricians and Gynecologists (ACOG).80 Ulipristal acetate (UPA). One study has demonstrated that UP can delay ovulation.81... Another study found that UPA altered the endometrium, but whether this change would inhibit implantation is unknown.82 p. 122: Progestin-only emergency contraceptive pills. Early treatment with ECPs containing only the progestin levonorgestrel has been shown to impair the ovulatory process and luteal function.83–87 p. 123: Combined emergency contraceptive pills. Several clinical studies have shown that combined ECPs containing ethinyl estradiol and levonorgestrel can inhibit or delay ovulation.107–110</blockquote> </li> <li id="cite_note-FSRH_EC_2012-28"><a href="#cite_ref-FSRH_EC_2012_28-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRCOG_Faculty_of_SexualReproductive_HealthcareClinical_Effectiveness_Unit2012" class="citation journal cs1">RCOG Faculty of Sexual, Reproductive Healthcare, Clinical Effectiveness Unit (January 2012). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20120526135043/http://www.fsrh.org/pdfs/CEUguidanceEmergencyContraception11.pdf">"Clinical guidance: emergency contraception"</a> (PDF). Clinical Guidance. London: Royal College of Obstetricians and Gynaecologists. <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/1755-103X">1755-103X</a>. Archived from <a rel="nofollow" class="external text" href="http://www.fsrh.org/pdfs/CEUguidanceEmergencyContraception11.pdf">the original</a> (PDF) on 26 May 2012. Retrieved 30 April 2012.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Clinical+Guidance&rft.atitle=Clinical+guidance%3A+emergency+contraception&rft.date=2012-01&rft.issn=1755-103X&rft.au=RCOG+Faculty+of+Sexual&rft.au=Reproductive+Healthcare&rft.au=Clinical+Effectiveness+Unit&rft_id=http%3A%2F%2Fwww.fsrh.org%2Fpdfs%2FCEUguidanceEmergencyContraception11.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> p.3:<blockquote>How does EC work? In 2002, a judicial review ruled that pregnancy begins at implantation, not fertilisation.8 The possible mechanisms of action should be explained to the patient as some methods may not be acceptable, depending on individual beliefs about the onset of pregnancy and abortion. Copper-bearing intrauterine device (Cu-IUD). Copper is toxic to the ovum and sperm and thus the copper-bearing intrauterine device (Cu-IUD) is effective immediately after insertion and works primarily by inhibiting fertilisation.9–11 A systematic review on mechanisms of action of IUDs showed that both pre- and postfertilisation effects contribute to efficacy.11 If fertilisation has already occurred, it is accepted that there is an anti-implantation effect,12,13 Levonorgestrel (LNG). The precise mode of action of levonorgestrel (LNG) is incompletely understood but it is thought to work primarily by inhibition of ovulation.16,17 Ulipristal acetate (UPA). UPA's primary mechanism of action is thought to be inhibition or delay of ovulation.2</blockquote> </li> <li id="cite_note-WHO_2010-29"><a href="#cite_ref-WHO_2010_29-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFUNDP/UNFPA/WHO/World_Bank_Special_Programme_of_Research,_Development_and_Research_Training_in_Human_Reproduction_(HRP)2010" class="citation web cs1">UNDP/UNFPA/WHO/World Bank Special Programme of Research, Development and Research Training in Human Reproduction (HRP) (25 March 2010). <a rel="nofollow" class="external text" href="http://whqlibdoc.who.int/hq/2010/WHO_RHR_HRP_10.06_eng.pdf">"Fact sheet on the safety of levonorgestrel-alone emergency contraceptive pills (LNG ECPs)"</a> (PDF). Geneva: World Health Organization. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20120316134151/http://whqlibdoc.who.int/hq/2010/WHO_RHR_HRP_10.06_eng.pdf">Archived</a> (PDF) from the original on 16 March 2012.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Fact+sheet+on+the+safety+of+levonorgestrel-alone+emergency+contraceptive+pills+%28LNG+ECPs%29&rft.place=Geneva&rft.pub=World+Health+Organization&rft.date=2010-03-25&rft.au=UNDP%2FUNFPA%2FWHO%2FWorld+Bank+Special+Programme+of+Research%2C+Development+and+Research+Training+in+Human+Reproduction+%28HRP%29&rft_id=http%3A%2F%2Fwhqlibdoc.who.int%2Fhq%2F2010%2FWHO_RHR_HRP_10.06_eng.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"><blockquote>Can LNG ECPs cause an abortion? LNG ECPs do not interrupt an established pregnancy or harm a developing embryo.15 The evidence available to date shows that LNG ECP use does not prevent a fertilized egg from attaching to the uterine lining. The primary mechanism of action is to stop or disrupt ovulation; LNG ECP use may also prevent the sperm and egg from meeting.16</blockquote> </li> <li id="cite_note-Speroff_2011-30"><a href="#cite_ref-Speroff_2011_30-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSperoffDarney2011" class="citation book cs1">Speroff L, Darney PD (2011). "Special uses of oral contraception: emergency contraception, the progestin-only minipill". A clinical guide for contraception (5th ed.). Philadelphia: Lippincott Williams & Wilkins. pp. 153–166. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-60831-610-6" title="Special:BookSources/978-1-60831-610-6"><bdi>978-1-60831-610-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Special+uses+of+oral+contraception%3A+emergency+contraception%2C+the+progestin-only+minipill&rft.btitle=A+clinical+guide+for+contraception&rft.place=Philadelphia&rft.pages=%3Cspan+class%3D%22nowrap%22%3E153-%3C%2Fspan%3E166&rft.edition=5th&rft.pub=Lippincott+Williams+%26+Wilkins&rft.date=2011&rft.isbn=978-1-60831-610-6&rft.aulast=Speroff&rft.aufirst=L&rft.au=Darney%2C+PD&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> p. 155: <blockquote>Emergency postcoital contraception Levonorgestrel Mechanism and efficacy</blockquote> </li> <li id="cite_note-Belluck_2012b-31"><a href="#cite_ref-Belluck_2012b_31-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBelluck2012" class="citation news cs1">Belluck P (6 June 2012). <a rel="nofollow" class="external text" href="https://www.nytimes.com/2012/06/06/health/research/morning-after-pills-dont-block-implantation-science-suggests.html?pagewanted=all">"No abortion role seen for morning-after pill"</a>. The New York Times. p. A1. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170227112421/http://www.nytimes.com/2012/06/06/health/research/morning-after-pills-dont-block-implantation-science-suggests.html?pagewanted=all">Archived</a> from the original on 27 February 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+New+York+Times&rft.atitle=No+abortion+role+seen+for+morning-after+pill&rft.pages=A1&rft.date=2012-06-06&rft.aulast=Belluck&rft.aufirst=P&rft_id=https%3A%2F%2Fwww.nytimes.com%2F2012%2F06%2F06%2Fhealth%2Fresearch%2Fmorning-after-pills-dont-block-implantation-science-suggests.html%3Fpagewanted%3Dall&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBelluck2012" class="citation news cs1">Belluck P (6 June 2012). <a rel="nofollow" class="external text" href="https://www.nytimes.com/2012/06/06/health/research/medications-nickname-may-have-helped-in-its-politcization.html">"Drug's nickname may have aided politicization"</a>. The New York Times. p. A14.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+New+York+Times&rft.atitle=Drug%27s+nickname+may+have+aided+politicization&rft.pages=A14&rft.date=2012-06-06&rft.aulast=Belluck&rft.aufirst=P&rft_id=https%3A%2F%2Fwww.nytimes.com%2F2012%2F06%2F06%2Fhealth%2Fresearch%2Fmedications-nickname-may-have-helped-in-its-politcization.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-FIGO_2011-32"><a href="#cite_ref-FIGO_2011_32-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFInternational_Federation_of_Gynecology_and_Obstetrics_(FIGO)_and_International_Consortium_for_Emergency_Contraception_(ICEC)2011" class="citation web cs1"><a href="/wiki/International_Federation_of_Gynecology_and_Obstetrics" class="mw-redirect" title="International Federation of Gynecology and Obstetrics">International Federation of Gynecology and Obstetrics</a> (FIGO) and International Consortium for Emergency Contraception (ICEC) (4 April 2011). <a rel="nofollow" class="external text" href="http://www.figo.org/sites/default/files/uploads/MOA_FINAL_2011_ENG.pdf">"Mechanism of action: How do levonorgestrel-only emergency contraceptive pills (LNG ECPs) prevent pregnancy?"</a> (PDF). London: International Federation of Gynecology and Obstetrics. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20141229024754/http://www.figo.org/sites/default/files/uploads/MOA_FINAL_2011_ENG.pdf">Archived</a> (PDF) from the original on 29 December 2014.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Mechanism+of+action%3A+How+do+levonorgestrel-only+emergency+contraceptive+pills+%28LNG+ECPs%29+prevent+pregnancy%3F&rft.place=London&rft.pub=International+Federation+of+Gynecology+and+Obstetrics&rft.date=2011-04-04&rft.au=International+Federation+of+Gynecology+and+Obstetrics+%28FIGO%29+and+International+Consortium+for+Emergency+Contraception+%28ICEC%29&rft_id=http%3A%2F%2Fwww.figo.org%2Fsites%2Fdefault%2Ffiles%2Fuploads%2FMOA_FINAL_2011_ENG.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"><blockquote>Levonorgestrel-only emergency contraceptive pills: • Interfere with the process of ovulation; • May possibly prevent the sperm and the egg from meeting. Implications of the research: • Inhibition or delay of ovulation is LNG ECPs principal and possibly only mechanism of action. • Review of the evidence suggests that LNG-ECs cannot prevent implantation of a fertilized egg. Language on implantation should not be included in LNG ECP product labeling. • The fact that LNG-ECs have no demonstrated effect on implantation explains why they are not 100% effective in preventing pregnancy and are less effective the later they are taken. Women should be given a clear message that LNG-ECs are more effective the sooner they are taken. • LNG ECPs do not interrupt a pregnancy (by any definition of the beginning of pregnancy). However, LNG ECPs can prevent abortions by reducing unwanted pregnancies.</blockquote> </li> <li id="cite_note-Belluck_2013-33">^ <a href="#cite_ref-Belluck_2013_33-0">a</a> <a href="#cite_ref-Belluck_2013_33-1">b</a> <a href="#cite_ref-Belluck_2013_33-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBelluck2013" class="citation news cs1">Belluck P (26 November 2013). <a rel="nofollow" class="external text" href="https://www.nytimes.com/2013/11/27/us/shift-on-birth-control-pill-may-affect-court-cases.html">"New birth control label counters lawsuit claim; European authorities found that a drug like Plan B One-Step cannot prevent fertilized eggs from implanting in the womb"</a>. The New York Times. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20140304233807/http://www.nytimes.com/2013/11/27/us/shift-on-birth-control-pill-may-affect-court-cases.html">Archived</a> from the original on 4 March 2014. Retrieved 5 March 2014.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+New+York+Times&rft.atitle=New+birth+control+label+counters+lawsuit+claim%3B+European+authorities+found+that+a+drug+like+Plan+B+One-Step+cannot+prevent+fertilized+eggs+from+implanting+in+the+womb&rft.date=2013-11-26&rft.aulast=Belluck&rft.aufirst=P&rft_id=https%3A%2F%2Fwww.nytimes.com%2F2013%2F11%2F27%2Fus%2Fshift-on-birth-control-pill-may-affect-court-cases.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHRA_Pharma2013" class="citation web cs1"><a href="/wiki/HRA_Pharma" class="mw-redirect" title="HRA Pharma">HRA Pharma</a> (November 2013). <a rel="nofollow" class="external text" href="http://www.imb.ie/images/uploaded/swedocuments/2126041.PA1166_002_001.a60606c0-00f0-4866-bc34-91bdfd679b1e.000001PACKAGE%20LEAFLET%201.5.131128.pdf">"NorLevo 1.5 mg tablet Patient Information Leaflet (PIL)"</a> (PDF). Dublin: Irish Medicines Board. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20140305170311/http://www.imb.ie/images/uploaded/swedocuments/2126041.PA1166_002_001.a60606c0-00f0-4866-bc34-91bdfd679b1e.000001PACKAGE%20LEAFLET%201.5.131128.pdf">Archived</a> (PDF) from the original on 5 March 2014. Retrieved 5 March 2014. <q>NorLevo works by stopping your ovaries from releasing an egg. It cannot stop a fertilized egg from attaching to the womb.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=NorLevo+1.5+mg+tablet+Patient+Information+Leaflet+%28PIL%29&rft.place=Dublin&rft.pub=Irish+Medicines+Board&rft.date=2013-11&rft.au=HRA+Pharma&rft_id=http%3A%2F%2Fwww.imb.ie%2Fimages%2Fuploaded%2Fswedocuments%2F2126041.PA1166_002_001.a60606c0-00f0-4866-bc34-91bdfd679b1e.000001PACKAGE%2520LEAFLET%25201.5.131128.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHRA_Pharma2013" class="citation web cs1"><a href="/wiki/HRA_Pharma" class="mw-redirect" title="HRA Pharma">HRA Pharma</a> (November 2013). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20120615184048/http://www.medicines.ie/medicine/11933/SPC/Norlevo+1.5mg+tablet#PHARMACODYNAMIC_PROPS">"NorLevo 1.5 mg tablet Summary of Product Characteristics (SPC)"</a>. Dublin: Irish Pharmaceutical Healthcare Association. Archived from <a rel="nofollow" class="external text" href="http://www.medicines.ie/medicine/11933/SPC/Norlevo+1.5mg+tablet/#PHARMACODYNAMIC_PROPS">the original</a> on 15 June 2012. Retrieved 5 March 2014.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=NorLevo+1.5+mg+tablet+Summary+of+Product+Characteristics+%28SPC%29&rft.place=Dublin&rft.pub=Irish+Pharmaceutical+Healthcare+Association&rft.date=2013-11&rft.au=HRA+Pharma&rft_id=http%3A%2F%2Fwww.medicines.ie%2Fmedicine%2F11933%2FSPC%2FNorlevo%2B1.5mg%2Btablet%2F%23PHARMACODYNAMIC_PROPS&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFEuropean_Medicines_Agency2014" class="citation news cs1">European Medicines Agency (24 January 2014). <a rel="nofollow" class="external text" href="http://www.ema.europa.eu/ema/index.jsp?curl=pages/news_and_events/news/2014/01/news_detail_002010.jsp&mid=WC0b01ac058004d5c1">"Review of emergency contraceptives started"</a>. London: European Medicines Agency. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20140327002519/http://www.ema.europa.eu/ema/index.jsp?curl=pages%2Fnews_and_events%2Fnews%2F2014%2F01%2Fnews_detail_002010.jsp&mid=WC0b01ac058004d5c1">Archived</a> from the original on 27 March 2014. Retrieved 5 March 2014.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Review+of+emergency+contraceptives+started&rft.date=2014-01-24&rft.au=European+Medicines+Agency&rft_id=http%3A%2F%2Fwww.ema.europa.eu%2Fema%2Findex.jsp%3Fcurl%3Dpages%2Fnews_and_events%2Fnews%2F2014%2F01%2Fnews_detail_002010.jsp%26mid%3DWC0b01ac058004d5c1&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-34"><a href="#cite_ref-34">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMozzanegaCosmi2011" class="citation journal cs1">Mozzanega B, Cosmi E (June 2011). "How do levonorgestrel-only emergency contraceptive pills prevent pregnancy? Some considerations". Gynecological Endocrinology. 27 (6): 439–42. <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%2F09513590.2010.501885">10.3109/09513590.2010.501885</a>. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<a rel="nofollow" class="external text" href="https://hdl.handle.net/11577%2F2476296">11577/2476296</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/20670097">20670097</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:6431709">6431709</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Gynecological+Endocrinology&rft.atitle=How+do+levonorgestrel-only+emergency+contraceptive+pills+prevent+pregnancy%3F+Some+considerations&rft.volume=27&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E439-%3C%2Fspan%3E42&rft.date=2011-06&rft_id=info%3Ahdl%2F11577%2F2476296&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A6431709%23id-name%3DS2CID&rft_id=info%3Apmid%2F20670097&rft_id=info%3Adoi%2F10.3109%2F09513590.2010.501885&rft.aulast=Mozzanega&rft.aufirst=B&rft.au=Cosmi%2C+E&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-35"><a href="#cite_ref-35">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLeungLevineSoon2010" class="citation journal cs1">Leung VW, Levine M, Soon JA (February 2010). "Mechanisms of action of hormonal emergency contraceptives". Pharmacotherapy. 30 (2): 158–68. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1592%2Fphco.30.2.158">10.1592/phco.30.2.158</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/20099990">20099990</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:41337748">41337748</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pharmacotherapy&rft.atitle=Mechanisms+of+action+of+hormonal+emergency+contraceptives&rft.volume=30&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E158-%3C%2Fspan%3E68&rft.date=2010-02&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A41337748%23id-name%3DS2CID&rft_id=info%3Apmid%2F20099990&rft_id=info%3Adoi%2F10.1592%2Fphco.30.2.158&rft.aulast=Leung&rft.aufirst=VW&rft.au=Levine%2C+M&rft.au=Soon%2C+JA&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-Glasier_2011-36"><a href="#cite_ref-Glasier_2011_36-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFGlasierCameronBlitheScherrer2011" class="citation journal cs1">Glasier A, Cameron ST, Blithe D, Scherrer B, Mathe H, Levy D, et al. 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Contraception. 84 (4): 363–7. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.contraception.2011.02.009">10.1016/j.contraception.2011.02.009</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/21920190">21920190</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=Can+we+identify+women+at+risk+of+pregnancy+despite+using+emergency+contraception%3F+Data+from+randomized+trials+of+ulipristal+acetate+and+levonorgestrel&rft.volume=84&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E363-%3C%2Fspan%3E7&rft.date=2011-10&rft_id=info%3Adoi%2F10.1016%2Fj.contraception.2011.02.009&rft_id=info%3Apmid%2F21920190&rft.aulast=Glasier&rft.aufirst=A&rft.au=Cameron%2C+ST&rft.au=Blithe%2C+D&rft.au=Scherrer%2C+B&rft.au=Mathe%2C+H&rft.au=Levy%2C+D&rft.au=Gainer%2C+E&rft.au=Ulmann%2C+A&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-Trussell_2014-37"><a href="#cite_ref-Trussell_2014_37-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFTrussellRaymondCleland2014" class="citation web cs1">Trussell J, Raymond EG, Cleland K (February 2014). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20100923040101/http://ec.princeton.edu/questions/ec-review.pdf">"Emergency contraception: a last chance to prevent unintended pregnancy"</a> (PDF). 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Journal of Andrology. 24 (4): 466–83. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fj.1939-4640.2003.tb02695.x">10.1002/j.1939-4640.2003.tb02695.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/12826683">12826683</a>. <q>Based on animal studies and clinical studies in women, 19‐norderived progestins are known to be potent in terms of gonadotropin suppression (Couzinet et al, 1996). Among this class of steroidal compounds are norethisterone (NET), norethynodrel, and its dextrorotatory isomer LNG (ie, the biologically active form of this progestin). The progestins of this class are known to be potent suppressors of gonadotropin secretion, and when administered to men these compounds induced a profound suppression of sperm production (Frick, 1973). 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Springer Science & Business Media. pp. 151–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4612-4340-3" title="Special:BookSources/978-1-4612-4340-3"><bdi>978-1-4612-4340-3</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170908140504/https://books.google.com/books?id=dgnpBwAAQBAJ&pg=PA151">Archived</a> from the original on 8 September 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Office+Gynecology%3A+Advanced+Management+Concepts&rft.pages=151-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-1-4612-4340-3&rft.aulast=Knaus&rft.aufirst=JV&rft.au=Isaacs%2C+JH&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DdgnpBwAAQBAJ%26pg%3DPA151&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-GolanTashjian2011-62"><a href="#cite_ref-GolanTashjian2011_62-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFGolanTashjianArmstrong2011" class="citation book cs1">Golan DE, Tashjian AH, Armstrong EJ (15 December 2011). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=WM7rvNUcrdsC&pg=PA516">Principles of Pharmacology: The Pathophysiologic Basis of Drug Therapy</a>. Lippincott Williams & Wilkins. pp. 516–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-60831-270-2" title="Special:BookSources/978-1-60831-270-2"><bdi>978-1-60831-270-2</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170908140504/https://books.google.com/books?id=WM7rvNUcrdsC&pg=PA516">Archived</a> from the original on 8 September 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Principles+of+Pharmacology%3A+The+Pathophysiologic+Basis+of+Drug+Therapy&rft.pages=516-&rft.pub=Lippincott+Williams+%26+Wilkins&rft.date=2011-12-15&rft.isbn=978-1-60831-270-2&rft.aulast=Golan&rft.aufirst=DE&rft.au=Tashjian%2C+AH&rft.au=Armstrong%2C+EJ&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DWM7rvNUcrdsC%26pg%3DPA516&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-BreastCancer1991-63"><a href="#cite_ref-BreastCancer1991_63-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCommittee_on_the_Relationship_Between_Oral_Contraceptives_and_BreastCancer1991" class="citation book cs1">Committee on the Relationship Between Oral Contraceptives and BreastCancer (1 January 1991). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=upYrAAAAYAAJ&pg=PA147">Oral Contraceptives and Breast Cancer</a>. 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Taylor & Francis. 2000. pp. 605–. <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>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170908140504/https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA605">Archived</a> from the original on 8 September 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Index+Nominum+2000%3A+International+Drug+Directory&rft.pages=605-&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%3DPA605&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-AlldredgeCorelli2012-69"><a href="#cite_ref-AlldredgeCorelli2012_69-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFAlldredgeCorelliErnst2012" class="citation book cs1">Alldredge BK, Corelli RL, Ernst ME (1 February 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=qcVpuHngXK0C&pg=PA1072">Koda-Kimble and Young's Applied Therapeutics: The Clinical Use of Drugs</a>. Lippincott Williams & Wilkins. pp. 1072–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-60913-713-7" title="Special:BookSources/978-1-60913-713-7"><bdi>978-1-60913-713-7</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170908140504/https://books.google.com/books?id=qcVpuHngXK0C&pg=PA1072">Archived</a> from the original on 8 September 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Koda-Kimble+and+Young%27s+Applied+Therapeutics%3A+The+Clinical+Use+of+Drugs&rft.pages=1072-&rft.pub=Lippincott+Williams+%26+Wilkins&rft.date=2012-02-01&rft.isbn=978-1-60913-713-7&rft.aulast=Alldredge&rft.aufirst=BK&rft.au=Corelli%2C+RL&rft.au=Ernst%2C+ME&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DqcVpuHngXK0C%26pg%3DPA1072&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-LaverySanfilippo2012-70"><a href="#cite_ref-LaverySanfilippo2012_70-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLaverySanfilippo2012" class="citation book cs1">Lavery JP, Sanfilippo JS (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=l9XTBwAAQBAJ&pg=PA248">Pediatric and Adolescent Obstetrics and Gynecology</a>. Springer Science & Business Media. pp. 248–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4612-5064-7" title="Special:BookSources/978-1-4612-5064-7"><bdi>978-1-4612-5064-7</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170908140504/https://books.google.com/books?id=l9XTBwAAQBAJ&pg=PA248">Archived</a> from the original on 8 September 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Pediatric+and+Adolescent+Obstetrics+and+Gynecology&rft.pages=248-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-1-4612-5064-7&rft.aulast=Lavery&rft.aufirst=JP&rft.au=Sanfilippo%2C+JS&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dl9XTBwAAQBAJ%26pg%3DPA248&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-OffermannsRosenthal2008-71"><a href="#cite_ref-OffermannsRosenthal2008_71-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFOffermannsRosenthal2008" class="citation book cs1">Offermanns S, Rosenthal W (14 August 2008). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=iwwo5gx8aX8C&pg=PA390">Encyclopedia of Molecular Pharmacology</a>. Springer Science & Business Media. pp. 390–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-540-38916-3" title="Special:BookSources/978-3-540-38916-3"><bdi>978-3-540-38916-3</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170908140504/https://books.google.com/books?id=iwwo5gx8aX8C&pg=PA390">Archived</a> from the original on 8 September 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Encyclopedia+of+Molecular+Pharmacology&rft.pages=390-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2008-08-14&rft.isbn=978-3-540-38916-3&rft.aulast=Offermanns&rft.aufirst=S&rft.au=Rosenthal%2C+W&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Diwwo5gx8aX8C%26pg%3DPA390&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-pmid24333799-72"><a href="#cite_ref-pmid24333799_72-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSchindler2014" class="citation journal cs1">Schindler AE (July 2014). "The "newer" progestogens and postmenopausal hormone therapy (HRT)". J Steroid Biochem Mol Biol. 142: 48–51. <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.2013.12.003">10.1016/j.jsbmb.2013.12.003</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/24333799">24333799</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:32126275">32126275</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J+Steroid+Biochem+Mol+Biol&rft.atitle=The+%22newer%22+progestogens+and+postmenopausal+hormone+therapy+%28HRT%29&rft.volume=142&rft.pages=%3Cspan+class%3D%22nowrap%22%3E48-%3C%2Fspan%3E51&rft.date=2014-07&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A32126275%23id-name%3DS2CID&rft_id=info%3Apmid%2F24333799&rft_id=info%3Adoi%2F10.1016%2Fj.jsbmb.2013.12.003&rft.aulast=Schindler&rft.aufirst=AE&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-GWU1987-73">^ <a href="#cite_ref-GWU1987_73-0">a</a> <a href="#cite_ref-GWU1987_73-1">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=zZhLAQAAIAAJ">Population Reports: Injectables and implants</a>. Department of Medical and Public Affairs, George Washington University. 1987. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210420164649/https://books.google.com/books?id=zZhLAQAAIAAJ">Archived</a> from the original on 20 April 2021. Retrieved 15 April 2018. <q>The Population Council also plans to test vaginal rings with two other progestins, ST-1435 and levonorgestrel acetate, alone and combined with ethinyl estradiol (168).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Population+Reports%3A+Injectables+and+implants&rft.pub=Department+of+Medical+and+Public+Affairs%2C+George+Washington+University.&rft.date=1987&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DzZhLAQAAIAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-pmid6658872-74">^ <a href="#cite_ref-pmid6658872_74-0">a</a> <a href="#cite_ref-pmid6658872_74-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCrabbéArcherBenagianoDiczfalusy1983" class="citation journal cs1">Crabbé P, Archer S, Benagiano G, Diczfalusy E, Djerassi C, Fried J, et al. (March 1983). "Long-acting contraceptive agents: design of the WHO Chemical Synthesis Programme". Steroids. 41 (3): 243–53. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0039-128X%2883%2990095-8">10.1016/0039-128X(83)90095-8</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/6658872">6658872</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:12896179">12896179</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=Long-acting+contraceptive+agents%3A+design+of+the+WHO+Chemical+Synthesis+Programme&rft.volume=41&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E243-%3C%2Fspan%3E53&rft.date=1983-03&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A12896179%23id-name%3DS2CID&rft_id=info%3Apmid%2F6658872&rft_id=info%3Adoi%2F10.1016%2F0039-128X%2883%2990095-8&rft.aulast=Crabb%C3%A9&rft.aufirst=P&rft.au=Archer%2C+S&rft.au=Benagiano%2C+G&rft.au=Diczfalusy%2C+E&rft.au=Djerassi%2C+C&rft.au=Fried%2C+J&rft.au=Higuchi%2C+T&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-PubChem-75"><a href="#cite_ref-PubChem_75-0">^</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://pubchem.ncbi.nlm.nih.gov/compound/13109">"Levonorgestrel"</a>. PubChem. Retrieved 18 August 2022.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=PubChem&rft.atitle=Levonorgestrel&rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fcompound%2F13109&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-DrugBank-76"><a href="#cite_ref-DrugBank_76-0">^</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://go.drugbank.com/drugs/DB00367">"Levonorgestrel: Uses, Interactions, Mechanism of Action"</a>. DrugBank Online. 30 October 2013. Retrieved 18 August 2022.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=DrugBank+Online&rft.atitle=Levonorgestrel%3A+Uses%2C+Interactions%2C+Mechanism+of+Action&rft.date=2013-10-30&rft_id=https%3A%2F%2Fgo.drugbank.com%2Fdrugs%2FDB00367&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-Meikle1999-77"><a href="#cite_ref-Meikle1999_77-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMeikle1999" class="citation book cs1">Meikle AW (1 June 1999). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=ja2nBgAAQBAJ&pg=PA383">Hormone Replacement Therapy</a>. Springer Science & Business Media. pp. 383–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-59259-700-0" title="Special:BookSources/978-1-59259-700-0"><bdi>978-1-59259-700-0</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200801012058/https://books.google.com/books?id=ja2nBgAAQBAJ&pg=PA383">Archived</a> from the original on 1 August 2020. Retrieved 15 April 2018. <q>The gonanes share the structural modifications found in the estranes and also possess [an ethyl] group at the position 13 and a keto group at position 3. Norgestrel was synthesized in 1963 and is a racemic mixture of dextro and levorotatory forms. The levorotatory form, levonorgestrel, provides the biological activity.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Hormone+Replacement+Therapy&rft.pages=383-&rft.pub=Springer+Science+%26+Business+Media&rft.date=1999-06-01&rft.isbn=978-1-59259-700-0&rft.aulast=Meikle&rft.aufirst=AW&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dja2nBgAAQBAJ%26pg%3DPA383&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-SzejtliSzente2012-78"><a href="#cite_ref-SzejtliSzente2012_78-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSzejtliSzente2012" class="citation book cs1">Szejtli J, Szente L (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=hkbqCAAAQBAJ&pg=PA317">Proceedings of the Eighth International Symposium on Cyclodextrins: Budapest, Hungary, March 31–April 2, 1996</a>. Springer Science & Business Media. pp. 317–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-94-011-5448-2" title="Special:BookSources/978-94-011-5448-2"><bdi>978-94-011-5448-2</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210828143153/https://books.google.com/books?id=hkbqCAAAQBAJ&pg=PA317">Archived</a> from the original on 28 August 2021. Retrieved 15 April 2018. <q>[Norgestrel] was discovered by Hughes et al. (1963).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Proceedings+of+the+Eighth+International+Symposium+on+Cyclodextrins%3A+Budapest%2C+Hungary%2C+March+31%E2%80%93April+2%2C+1996&rft.pages=317-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-94-011-5448-2&rft.aulast=Szejtli&rft.aufirst=J&rft.au=Szente%2C+L&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DhkbqCAAAQBAJ%26pg%3DPA317&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-FilshieGuillebaud2013-79">^ <a href="#cite_ref-FilshieGuillebaud2013_79-0">a</a> <a href="#cite_ref-FilshieGuillebaud2013_79-1">b</a> <a href="#cite_ref-FilshieGuillebaud2013_79-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFilshieGuillebaud2013" class="citation book cs1">Filshie M, Guillebaud J (22 October 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=Ug3-BAAAQBAJ&pg=PA12">Contraception: Science and Practice</a>. Elsevier Science. pp. 12–. <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>Norgestrel, developed by Wyeth and patented in 1964, was the first progestogen to be manufactured by total chemical synthesis. It was subsequently licensed to Schering AG, who separated the racemic mixture into an inactive structural isomer l-norgestrel and the active d-norgestrel -- more usually known as dextronorgestrel and levonorgestrel respectively, because of the optical isomerism that each displays.</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=12-&rft.pub=Elsevier+Science&rft.date=2013-10-22&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%3DPA12&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-Marks2010-80">^ <a href="#cite_ref-Marks2010_80-0">a</a> <a href="#cite_ref-Marks2010_80-1">b</a> <a href="#cite_ref-Marks2010_80-2">c</a> <a href="#cite_ref-Marks2010_80-3">d</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=PA76">Sexual Chemistry: A History of the Contraceptive Pill</a>. Yale University Press. pp. 73, 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>. <q>In 1964 the pharmaceutical company Wyeth developed norgestrel, the first progestogen to be made from a total chemical synthesis. Subsequently licensed to Schering AG, norgestrel was used to develop levonorgestrel, another active progestogen later used for oral contraception.</q></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=73%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%3DPA76&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-Pohl2004-81">^ <a href="#cite_ref-Pohl2004_81-0">a</a> <a href="#cite_ref-Pohl2004_81-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPohl2004" class="citation book cs1">Pohl WG (2004). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=PtTuOXYBi3IC&pg=PA150">Die wissenschaftliche Welt von gestern: die Preisträger des Ignaz L. Lieben-Preises 1865-1937 und des Richard Lieben-Preises 1912-1928 : ein Kapitel österreichischer Wissenschaftsgeschichte in Kurzbiografien</a>. Böhlau Verlag Wien. pp. 150–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-205-77303-0" title="Special:BookSources/978-3-205-77303-0"><bdi>978-3-205-77303-0</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210828143152/https://books.google.com/books?id=PtTuOXYBi3IC&pg=PA150">Archived</a> from the original on 28 August 2021. Retrieved 18 April 2018. <q>[The contraceptive EUGYNON is launched in 1966. NEOGYNON follows in 1970.]</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Die+wissenschaftliche+Welt+von+gestern%3A+die+Preistr%C3%A4ger+des+Ignaz+L.+Lieben-Preises+1865-1937+und+des+Richard+Lieben-Preises+1912-1928+%3A+ein+Kapitel+%C3%B6sterreichischer+Wissenschaftsgeschichte+in+Kurzbiografien&rft.pages=150-&rft.pub=B%C3%B6hlau+Verlag+Wien&rft.date=2004&rft.isbn=978-3-205-77303-0&rft.aulast=Pohl&rft.aufirst=WG&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DPtTuOXYBi3IC%26pg%3DPA150&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-Ortiz-GómezSantesmases2016-82">^ <a href="#cite_ref-Ortiz-GómezSantesmases2016_82-0">a</a> <a href="#cite_ref-Ortiz-GómezSantesmases2016_82-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFOrtiz-GómezSantesmases2016" class="citation book cs1">Ortiz-Gómez T, Santesmases MJ (22 April 2016). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=snUGDAAAQBAJ&pg=PT175">Gendered Drugs and Medicine: Historical and Socio-Cultural Perspectives</a>. Taylor & Francis. pp. 175–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-317-12981-3" title="Special:BookSources/978-1-317-12981-3"><bdi>978-1-317-12981-3</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20211006041600/https://books.google.com/books?id=SNuGDAAAQBAJ">Archived</a> from the original on 6 October 2021. Retrieved 18 April 2018. <q>The 1966 marketing campaign for Schering's second contraceptive, Eugynon, [...] (Schering AG Berline 1966, 11). [...] In 1970 [Schering] had already conducted an opinion poll among doctors in the run-up to the marketing campaign for the newly introduced Neogynon. [...]</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Gendered+Drugs+and+Medicine%3A+Historical+and+Socio-Cultural+Perspectives&rft.pages=175-&rft.pub=Taylor+%26+Francis&rft.date=2016-04-22&rft.isbn=978-1-317-12981-3&rft.aulast=Ortiz-G%C3%B3mez&rft.aufirst=T&rft.au=Santesmases%2C+MJ&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DsnUGDAAAQBAJ%26pg%3DPT175&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-ToneWatkins2007-83"><a href="#cite_ref-ToneWatkins2007_83-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFToneWatkins2007" class="citation book cs1">Tone A, Watkins ES (8 January 2007). <a rel="nofollow" class="external text" href="https://archive.org/details/isbn_9780814783016">Medicating Modern America: Prescription Drugs in History</a>. NYU Press. pp. <a rel="nofollow" class="external text" href="https://archive.org/details/isbn_9780814783016/page/118">118</a>–119. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-8147-8300-9" title="Special:BookSources/978-0-8147-8300-9"><bdi>978-0-8147-8300-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Medicating+Modern+America%3A+Prescription+Drugs+in+History&rft.pages=118-119&rft.pub=NYU+Press&rft.date=2007-01-08&rft.isbn=978-0-8147-8300-9&rft.aulast=Tone&rft.aufirst=A&rft.au=Watkins%2C+ES&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fisbn_9780814783016&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-Albach1993-84"><a href="#cite_ref-Albach1993_84-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFAlbach1993" class="citation book cs1">Albach H (1993). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=jIi3AAAAIAAJ&q=neogynon">Culture and Technical Innovation: A Cross-Cultural Analysis and Policy Recommendations</a>. Walter de Gruyter. p. 952. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-11-013947-1" title="Special:BookSources/978-3-11-013947-1"><bdi>978-3-11-013947-1</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210828143153/https://books.google.com/books?id=jIi3AAAAIAAJ&q=neogynon">Archived</a> from the original on 28 August 2021. Retrieved 5 August 2020. <q>[Since the safety of ovulation inhibition by levonorgestrel was also proven in the clinical studies, the cycle was extremely stable and the side effects were low, the drug was on August 1, 1970 introduced as Neogynon 21 and Neogynon 28 in Germany on the market.] [...] After the OC market had risen sharply in 1968 and 1969, the launch of Neogynon / Schering and Stediril-d / Wyeth in August 1970 gave the market a fresh boost.]</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Culture+and+Technical+Innovation%3A+A+Cross-Cultural+Analysis+and+Policy+Recommendations&rft.pages=952&rft.pub=Walter+de+Gruyter&rft.date=1993&rft.isbn=978-3-11-013947-1&rft.aulast=Albach&rft.aufirst=H&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DjIi3AAAAIAAJ%26q%3Dneogynon&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-ApeloVeloso1970-85"><a href="#cite_ref-ApeloVeloso1970_85-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFApeloVeloso1970" class="citation journal cs1">Apelo R, Veloso I (1970). "Results of a controlled study employing d-norgestrel and ethinyl estradiol". Contraception. 2 (6): 391–400. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0010-7824%2870%2980002-6">10.1016/S0010-7824(70)80002-6</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>. <q>The results obtained in these series clinically confirmed the findings in animal work on the potency of d-norgestrel, i.e., that the biological activity of norgestrel resides largely in the d-enantlomer (5,6).</q></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=Results+of+a+controlled+study+employing+d-norgestrel+and+ethinyl+estradiol&rft.volume=2&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E391-%3C%2Fspan%3E400&rft.date=1970&rft_id=info%3Adoi%2F10.1016%2FS0010-7824%2870%2980002-6&rft.issn=0010-7824&rft.aulast=Apelo&rft.aufirst=R&rft.au=Veloso%2C+I&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-BrosensVanAssche1971-86"><a href="#cite_ref-BrosensVanAssche1971_86-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBrosensVan_AsscheWijnants1971" class="citation journal cs1">Brosens I, Van Assche A, Wijnants P (1971). <a rel="nofollow" class="external text" href="https://www.popline.org/node/485953">"Comparative clinical and morphological studies on 2 oral contraceptives which contain DL-norgestrel and D-norgestrel respectively"</a>. Geburtshilfe und Frauenheilkunde. 31 (3): 251–257. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20180415190302/https://www.popline.org/node/485953">Archived</a> from the original on 15 April 2018. Retrieved 15 April 2018. <q>Comparison of the effects of Eugynon and Neogynon (.05 mg ethinyl estradiol with .5 mg norgestrel or with .25 mg d-norgestrel, respectively) in 272 women is reported. The 2 preparations were comparable as regards effectiveness (100%), cycle control, and endometrial and cervical morphology. No clinical or biological complications occurred, and the incidence of minor side effects was very small. The d-norgestrel preparation (Neogynon) may be preferable for metabolic reasons because of its lower steroid dose.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Geburtshilfe+und+Frauenheilkunde&rft.atitle=Comparative+clinical+and+morphological+studies+on+2+oral+contraceptives+which+contain+DL-norgestrel+and+D-norgestrel+respectively.&rft.volume=31&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E251-%3C%2Fspan%3E257&rft.date=1971&rft.aulast=Brosens&rft.aufirst=I&rft.au=Van+Assche%2C+A&rft.au=Wijnants%2C+P&rft_id=https%3A%2F%2Fwww.popline.org%2Fnode%2F485953&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-SchneiderSpona1974-87"><a href="#cite_ref-SchneiderSpona1974_87-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSchneiderSponaMatt1974" class="citation journal cs1">Schneider W, Spona J, Matt K (1974). "Inhibition of ovulation by means of a combined preparation with reduced amounts of active substance". Contraception. 9 (1): 81–92. <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%2874%2990096-1">10.1016/0010-7824(74)90096-1</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=Inhibition+of+ovulation+by+means+of+a+combined+preparation+with+reduced+amounts+of+active+substance&rft.volume=9&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E81-%3C%2Fspan%3E92&rft.date=1974&rft_id=info%3Adoi%2F10.1016%2F0010-7824%2874%2990096-1&rft.issn=0010-7824&rft.aulast=Schneider&rft.aufirst=W&rft.au=Spona%2C+J&rft.au=Matt%2C+K&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-pmid4614952-88"><a href="#cite_ref-pmid4614952_88-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBrat1974" class="citation journal cs1">Brat T (1974). "Clinical trial with a new low oestrogen combined oral contraceptive". Current Medical Research and Opinion. 2 (8): 465–470. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1185%2F03007997409115244">10.1185/03007997409115244</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/4614952">4614952</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Current+Medical+Research+and+Opinion&rft.atitle=Clinical+trial+with+a+new+low+oestrogen+combined+oral+contraceptive&rft.volume=2&rft.issue=8&rft.pages=%3Cspan+class%3D%22nowrap%22%3E465-%3C%2Fspan%3E470&rft.date=1974&rft_id=info%3Adoi%2F10.1185%2F03007997409115244&rft_id=info%3Apmid%2F4614952&rft.aulast=Brat&rft.aufirst=T&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-Scharff1972-89">^ <a href="#cite_ref-Scharff1972_89-0">a</a> <a href="#cite_ref-Scharff1972_89-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFScharff1972" class="citation journal cs1">Scharff HJ (1972). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20180415190319/https://www.popline.org/node/488633">"Clinical experience with Microlut"</a>. Medical News Schering. 28 (9): 2–9. Archived from <a rel="nofollow" class="external text" href="https://www.popline.org/node/488633">the original</a> on 15 April 2018.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Medical+News+Schering&rft.atitle=Clinical+experience+with+Microlut.&rft.volume=28&rft.issue=9&rft.pages=%3Cspan+class%3D%22nowrap%22%3E2-%3C%2Fspan%3E9&rft.date=1972&rft.aulast=Scharff&rft.aufirst=HJ&rft_id=https%3A%2F%2Fwww.popline.org%2Fnode%2F488633&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-pmid4817042-90"><a href="#cite_ref-pmid4817042_90-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLambotteWerbrouck-Navette1974" class="citation journal cs1 cs1-prop-foreign-lang-source">Lambotte R, Werbrouck-Navette J (March 1974). <a rel="nofollow" class="external text" href="https://www.popline.org/node/493200">"[Minipill as the new contraceptive method]"</a>. Revue Médicale de Liège (in French). 29 (6): 157–159. <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/4817042">4817042</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20180415190418/https://www.popline.org/node/493200">Archived</a> from the original on 15 April 2018. Retrieved 15 April 2018.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Revue+M%C3%A9dicale+de+Li%C3%A8ge&rft.atitle=%5BMinipill+as+the+new+contraceptive+method%5D&rft.volume=29&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E157-%3C%2Fspan%3E159&rft.date=1974-03&rft_id=info%3Apmid%2F4817042&rft.aulast=Lambotte&rft.aufirst=R&rft.au=Werbrouck-Navette%2C+J&rft_id=https%3A%2F%2Fwww.popline.org%2Fnode%2F493200&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-KesserüLarrañaga1973-91">^ <a href="#cite_ref-KesserüLarrañaga1973_91-0">a</a> <a href="#cite_ref-KesserüLarrañaga1973_91-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKesserüLarrañagaParada1973" class="citation journal cs1">Kesserü E, Larrañaga A, Parada J (1973). "Postcoital contraception with D-norgestrel". Contraception. 7 (5): 367–379. <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%2990139-X">10.1016/0010-7824(73)90139-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/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=Postcoital+contraception+with+D-norgestrel&rft.volume=7&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E367-%3C%2Fspan%3E379&rft.date=1973&rft_id=info%3Adoi%2F10.1016%2F0010-7824%2873%2990139-X&rft.issn=0010-7824&rft.aulast=Kesser%C3%BC&rft.aufirst=E&rft.au=Larra%C3%B1aga%2C+A&rft.au=Parada%2C+J&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-RubioBerman1970-92"><a href="#cite_ref-RubioBerman1970_92-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRubioBermanLarranagaGuiloff1970" class="citation journal cs1">Rubio B, Berman E, Larranaga A, Guiloff E (1970). "A new postcoital oral contraceptive". Contraception. 1 (5): 303–314. <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%2870%2990016-8">10.1016/0010-7824(70)90016-8</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=A+new+postcoital+oral+contraceptive&rft.volume=1&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E303-%3C%2Fspan%3E314&rft.date=1970&rft_id=info%3Adoi%2F10.1016%2F0010-7824%2870%2990016-8&rft.issn=0010-7824&rft.aulast=Rubio&rft.aufirst=B&rft.au=Berman%2C+E&rft.au=Larranaga%2C+A&rft.au=Guiloff%2C+E&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-Balaji2009-93"><a href="#cite_ref-Balaji2009_93-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBalaji2009" class="citation book cs1">Balaji (19 November 2009). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=xbp2B4fFL7wC&pg=RA1-PA569">Textbook of Oral and Maxillofacial Surgery</a>. Elsevier India. p. 569. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-81-312-0300-2" title="Special:BookSources/978-81-312-0300-2"><bdi>978-81-312-0300-2</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210828143153/https://www.google.com/books/edition/Textbook_of_Oral_and_Maxillofacial_Surge/xbp2B4fFL7wC?hl=en&gbpv=1&pg=RA1-PA569&printsec=frontcover">Archived</a> from the original on 28 August 2021. Retrieved 15 April 2018. <q>There are two main methods involving oral emergency pills, commonly misleadingly described as the 'morning-after pill'. The first older method, developed in the mid-1970s, involves two high-dose combined pills containing oestrogen (50 ug ethinyloestradiol) and progesterone (0.25 mg levonorgestrel): the Yuzpe regime (Schering PC4 or Ovran). The second involves progesterone only (0.75 mg levonorgestrel), and therefore, has a lower incidence of side effects, in particular vomiting (6%).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Textbook+of+Oral+and+Maxillofacial+Surgery&rft.pages=569&rft.pub=Elsevier+India&rft.date=2009-11-19&rft.isbn=978-81-312-0300-2&rft.au=Balaji&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dxbp2B4fFL7wC%26pg%3DRA1-PA569&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-pmid4844513-94"><a href="#cite_ref-pmid4844513_94-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFYuzpeThurlowRamzyLeyshon1974" class="citation journal cs1">Yuzpe AA, Thurlow HJ, Ramzy I, Leyshon JI (August 1974). "Post coital contraception--A pilot study". The Journal of Reproductive Medicine. 13 (2): 53–8. <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/4844513">4844513</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+Reproductive+Medicine&rft.atitle=Post+coital+contraception--A+pilot+study&rft.volume=13&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E53-%3C%2Fspan%3E8&rft.date=1974-08&rft_id=info%3Apmid%2F4844513&rft.aulast=Yuzpe&rft.aufirst=AA&rft.au=Thurlow%2C+HJ&rft.au=Ramzy%2C+I&rft.au=Leyshon%2C+JI&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-Farkas1978-95"><a href="#cite_ref-Farkas1978_95-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFarkas1978" class="citation journal cs1">Farkas M (1978). <a rel="nofollow" class="external text" href="https://scholar.google.com/scholar?cluster=8190066278284376785">"Post-coital contraception with Postinor, a preparation containing 0.75 mg d-norgestrel"</a>. Magyar Nöorvosok Lapja. 41: 474.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Magyar+N%C3%B6orvosok+Lapja&rft.atitle=Post-coital+contraception+with+Postinor%2C+a+preparation+containing+0.75+mg+d-norgestrel.&rft.volume=41&rft.pages=474&rft.date=1978&rft.aulast=Farkas&rft.aufirst=M&rft_id=https%3A%2F%2Fscholar.google.com%2Fscholar%3Fcluster%3D8190066278284376785&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-ArtiniGenazzani2001-96"><a href="#cite_ref-ArtiniGenazzani2001_96-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFArtiniGenazzaniPetraglia2001" class="citation book cs1">Artini PG, Genazzani AR, Petraglia F (11 December 2001). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=dknDdAonzlUC&pg=PA96">Advances in Gynecological Endocrinology</a>. CRC Press. pp. 96–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-84214-071-0" title="Special:BookSources/978-1-84214-071-0"><bdi>978-1-84214-071-0</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210828143313/https://books.google.com/books?id=dknDdAonzlUC&pg=PA96">Archived</a> from the original on 28 August 2021. Retrieved 15 April 2018.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Advances+in+Gynecological+Endocrinology&rft.pages=96-&rft.pub=CRC+Press&rft.date=2001-12-11&rft.isbn=978-1-84214-071-0&rft.aulast=Artini&rft.aufirst=PG&rft.au=Genazzani%2C+AR&rft.au=Petraglia%2C+F&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DdknDdAonzlUC%26pg%3DPA96&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-pmid8473453-97"><a href="#cite_ref-pmid8473453_97-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHoKwan1993" class="citation journal cs1">Ho PC, Kwan MS (March 1993). "A prospective randomized comparison of levonorgestrel with the Yuzpe regimen in post-coital contraception". Human Reproduction. 8 (3): 389–92. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Foxfordjournals.humrep.a138057">10.1093/oxfordjournals.humrep.a138057</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/8473453">8473453</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Human+Reproduction&rft.atitle=A+prospective+randomized+comparison+of+levonorgestrel+with+the+Yuzpe+regimen+in+post-coital+contraception&rft.volume=8&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E389-%3C%2Fspan%3E92&rft.date=1993-03&rft_id=info%3Adoi%2F10.1093%2Foxfordjournals.humrep.a138057&rft_id=info%3Apmid%2F8473453&rft.aulast=Ho&rft.aufirst=PC&rft.au=Kwan%2C+MS&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-King2013-98"><a href="#cite_ref-King2013_98-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKing2013" class="citation book cs1">King (21 October 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=dbaNAQAAQBAJ&pg=PA493">Varney's Midwifery</a>. Jones & Bartlett Publishers. pp. 493–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-284-02542-2" title="Special:BookSources/978-1-284-02542-2"><bdi>978-1-284-02542-2</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210828143335/https://books.google.com/books?id=dbaNAQAAQBAJ&pg=PA493">Archived</a> from the original on 28 August 2021. Retrieved 15 April 2018.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Varney%27s+Midwifery&rft.pages=493-&rft.pub=Jones+%26+Bartlett+Publishers&rft.date=2013-10-21&rft.isbn=978-1-284-02542-2&rft.au=King&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DdbaNAQAAQBAJ%26pg%3DPA493&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-Harrison-Woolrych2015-99"><a href="#cite_ref-Harrison-Woolrych2015_99-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHarrison-Woolrych2015" class="citation book cs1">Harrison-Woolrych M (28 January 2015). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=A0ZvBgAAQBAJ&pg=PA205">Medicines For Women</a>. Springer. pp. 205–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-319-12406-3" title="Special:BookSources/978-3-319-12406-3"><bdi>978-3-319-12406-3</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210828143313/https://books.google.com/books?id=A0ZvBgAAQBAJ&pg=PA205">Archived</a> from the original on 28 August 2021. Retrieved 15 April 2018.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Medicines+For+Women&rft.pages=205-&rft.pub=Springer&rft.date=2015-01-28&rft.isbn=978-3-319-12406-3&rft.aulast=Harrison-Woolrych&rft.aufirst=M&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DA0ZvBgAAQBAJ%26pg%3DPA205&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-CBSNews2013-100">^ <a href="#cite_ref-CBSNews2013_100-0">a</a> <a href="#cite_ref-CBSNews2013_100-1">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="http://www.cbsnews.com/news/fda-approves-over-the-counter-sales-of-plan-b-one-step-for-all-ages/">"FDA approves over-the-counter sales of Plan B One-Step for all ages"</a>. <a href="/wiki/CBS_News" title="CBS News">CBS News</a>. 20 June 2013. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170803212130/http://www.cbsnews.com/news/fda-approves-over-the-counter-sales-of-plan-b-one-step-for-all-ages/">Archived</a> from the original on 3 August 2017. Retrieved 3 August 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=CBS+News&rft.atitle=FDA+approves+over-the-counter+sales+of+Plan+B+One-Step+for+all+ages&rft.date=2013-06-20&rft_id=http%3A%2F%2Fwww.cbsnews.com%2Fnews%2Ffda-approves-over-the-counter-sales-of-plan-b-one-step-for-all-ages%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-Princeton2017-101"><a href="#cite_ref-Princeton2017_101-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFTrussellCleland2007" class="citation web cs1">Trussell J, Cleland K (10 April 2007). <a rel="nofollow" class="external text" href="http://ec.princeton.edu/questions/dedicated.html">"Emergency Contraceptive Pills Worldwide"</a>. <a href="/wiki/Princeton_University" title="Princeton University">Princeton University</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20070522214523/http://ec.princeton.edu/questions/dedicated.html">Archived</a> from the original on 22 May 2007. Retrieved 28 May 2007.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Emergency+Contraceptive+Pills+Worldwide&rft.pub=Princeton+University&rft.date=2007-04-10&rft.aulast=Trussell&rft.aufirst=J&rft.au=Cleland%2C+K&rft_id=http%3A%2F%2Fec.princeton.edu%2Fquestions%2Fdedicated.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-OatsAbraham2011-102"><a href="#cite_ref-OatsAbraham2011_102-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFOatsAbraham2011" class="citation book cs1">Oats JJ, Abraham S (17 November 2011). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=oZjGAAAAQBAJ&pg=PA247">Llewellyn-Jones Fundamentals of Obstetrics and Gynaecology E-Book</a>. Elsevier Health Sciences. pp. 247–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7234-3719-2" title="Special:BookSources/978-0-7234-3719-2"><bdi>978-0-7234-3719-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Llewellyn-Jones+Fundamentals+of+Obstetrics+and+Gynaecology+E-Book&rft.pages=247-&rft.pub=Elsevier+Health+Sciences&rft.date=2011-11-17&rft.isbn=978-0-7234-3719-2&rft.aulast=Oats&rft.aufirst=JJ&rft.au=Abraham%2C+S&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DoZjGAAAAQBAJ%26pg%3DPA247&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-CarlsonEisenstat2004-103"><a href="#cite_ref-CarlsonEisenstat2004_103-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCarlsonEisenstatZiporyn2004" class="citation book cs1">Carlson KJ, Eisenstat SA, Ziporyn TD (2004). <a rel="nofollow" class="external text" href="https://archive.org/details/newharvardguidet00carl">The New Harvard Guide to Women's Health</a>. Harvard University Press. pp. <a rel="nofollow" class="external text" href="https://archive.org/details/newharvardguidet00carl/page/285">285</a>–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-674-01282-0" title="Special:BookSources/978-0-674-01282-0"><bdi>978-0-674-01282-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+New+Harvard+Guide+to+Women%27s+Health&rft.pages=285-&rft.pub=Harvard+University+Press&rft.date=2004&rft.isbn=978-0-674-01282-0&rft.aulast=Carlson&rft.aufirst=KJ&rft.au=Eisenstat%2C+SA&rft.au=Ziporyn%2C+TD&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fnewharvardguidet00carl&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-104"><a href="#cite_ref-104">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDugan_Arnett2022" class="citation news cs1">Dugan Arnett (27 March 2022). <a rel="nofollow" class="external text" href="https://www.bostonglobe.com/2022/03/27/metro/some-states-seek-limit-reproductive-freedoms-bu-opens-plan-b-vending-machine/">"As some states seek to limit reproductive freedoms, BU opens 'Plan B' vending machine"</a>. <a href="/wiki/The_Boston_Globe" title="The Boston Globe">The Boston Globe</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20220328235410/https://www.bostonglobe.com/2022/03/27/metro/some-states-seek-limit-reproductive-freedoms-bu-opens-plan-b-vending-machine/">Archived</a> from the original on 28 March 2022. Retrieved 28 March 2022.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Boston+Globe&rft.atitle=As+some+states+seek+to+limit+reproductive+freedoms%2C+BU+opens+%27Plan+B%27+vending+machine&rft.date=2022-03-27&rft.au=Dugan+Arnett&rft_id=https%3A%2F%2Fwww.bostonglobe.com%2F2022%2F03%2F27%2Fmetro%2Fsome-states-seek-limit-reproductive-freedoms-bu-opens-plan-b-vending-machine%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> <li id="cite_note-105"><a href="#cite_ref-105">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRankin2015" class="citation web cs1">Rankin K (22 October 2015). <a rel="nofollow" class="external text" href="http://www.colorlines.com/articles/policy-gives-native-women-equal-access-emergency-contraception">"This Policy Gives Native Women Equal Access to Emergency Contraception"</a>. Colorlines. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20151026014315/http://www.colorlines.com/articles/policy-gives-native-women-equal-access-emergency-contraception">Archived</a> from the original on 26 October 2015. Retrieved 24 October 2015.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=This+Policy+Gives+Native+Women+Equal+Access+to+Emergency+Contraception&rft.pub=Colorlines&rft.date=2015-10-22&rft.aulast=Rankin&rft.aufirst=K&rft_id=http%3A%2F%2Fwww.colorlines.com%2Farticles%2Fpolicy-gives-native-women-equal-access-emergency-contraception&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALevonorgestrel" class="Z3988"> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2>[<a href="/w/index.php?title=Levonorgestrel&action=edit&section=30" title="Edit section: External links">edit</a>]</div> <a href="/wiki/File:Commons-logo.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/12px-Commons-logo.svg.png" decoding="async" width="12" height="16" class="mw-file-element" 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style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Progestogens_and_antiprogestogens" title="Template:Progestogens and antiprogestogens"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Progestogens_and_antiprogestogens" title="Template talk:Progestogens and antiprogestogens"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Progestogens_and_antiprogestogens" title="Special:EditPage/Template:Progestogens and antiprogestogens"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Progestogens_and_antiprogestogens153" style="font-size:114%;margin:0 4em"><a href="/wiki/Progestogen_(medication)" title="Progestogen (medication)">Progestogens</a> and <a href="/wiki/Antiprogestogen" title="Antiprogestogen">antiprogestogens</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Progestogen_(medication)" title="Progestogen (medication)">Progestogens</a> (and <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestins</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="PRTooltip_Progesterone_receptor_agonists408" scope="row" class="navbox-group" style="width:8em;;text-align:center;"><a href="/wiki/Progesterone_receptor" title="Progesterone receptor"><abbr title="Progesterone receptor">PR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Progesterone receptor <a href="/wiki/Agonist" title="Agonist">agonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Progesterone derivatives: <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">Progesterone</a></li> <li><a href="/wiki/Quingestrone" title="Quingestrone">Quingestrone</a></li></ul> <ul><li>Retroprogesterone derivatives: <a href="/wiki/Dydrogesterone" title="Dydrogesterone">Dydrogesterone</a></li> <li><a href="/wiki/Trengestone" title="Trengestone">Trengestone</a></li></ul> <ul><li>17α-Hydroxyprogesterone (and closely related) derivatives: 17α-Hydroxylated: <a href="/wiki/Acetomepregenol" title="Acetomepregenol">Acetomepregenol (mepregenol diacetate)</a></li> <li><a href="/wiki/Algestone_acetophenide" title="Algestone acetophenide">Algestone acetophenide (dihydroxyprogesterone acetophenide)</a></li> <li><a href="/wiki/Anagestone_acetate" title="Anagestone acetate">Anagestone acetate</a></li> <li><a href="/wiki/Chlormadinone_acetate" title="Chlormadinone acetate">Chlormadinone acetate</a></li> <li><a href="/wiki/Chlormethenmadinone_acetate" title="Chlormethenmadinone acetate">Chlormethenmadinone acetate</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Delmadinone_acetate" title="Delmadinone acetate">Delmadinone acetate</a></li> <li><a href="/wiki/Flugestone_acetate" title="Flugestone acetate">Flugestone acetate (flurogestone acetate)</a></li> <li><a href="/wiki/Flumedroxone_acetate" title="Flumedroxone acetate">Flumedroxone acetate</a></li> <li><a href="/wiki/Hydroxyprogesterone_acetate" title="Hydroxyprogesterone acetate">Hydroxyprogesterone acetate</a></li> <li><a href="/wiki/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">Hydroxyprogesterone caproate</a></li> <li><a href="/wiki/Hydroxyprogesterone_heptanoate" title="Hydroxyprogesterone heptanoate">Hydroxyprogesterone heptanoate</a></li> <li><a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">Medroxyprogesterone acetate</a>#</li> <li><a href="/wiki/Megestrol_acetate" title="Megestrol acetate">Megestrol acetate</a></li> <li><a href="/wiki/Melengestrol_acetate" title="Melengestrol acetate">Melengestrol acetate</a></li> <li><a href="/wiki/Methenmadinone_acetate" title="Methenmadinone acetate">Methenmadinone acetate</a></li> <li><a href="/wiki/Osaterone_acetate" title="Osaterone acetate">Osaterone acetate</a></li> <li><a href="/wiki/Pentagestrone_acetate" title="Pentagestrone acetate">Pentagestrone acetate</a></li> <li><a href="/wiki/Proligestone" title="Proligestone">Proligestone</a>; 17α-Methylated: <a href="/wiki/Medrogestone" title="Medrogestone">Medrogestone</a>; Others: <a href="/wiki/Haloprogesterone" title="Haloprogesterone">Haloprogesterone</a></li></ul> <ul><li>19-Norprogesterone derivatives: 17α-Hydroxylated: <a href="/wiki/Gestonorone_caproate" title="Gestonorone caproate">Gestonorone caproate (gestronol hexanoate)</a></li> <li><a href="/wiki/Nomegestrol_acetate" title="Nomegestrol acetate">Nomegestrol acetate</a></li> <li><a href="/wiki/Norgestomet" title="Norgestomet">Norgestomet</a></li> <li><a href="/wiki/Segesterone_acetate" title="Segesterone acetate">Segesterone acetate (nestorone, elcometrine)</a>; 17α-Methylated: <a href="/wiki/Demegestone" title="Demegestone">Demegestone</a></li> <li><a href="/wiki/Promegestone" title="Promegestone">Promegestone</a></li> <li><a href="/wiki/Trimegestone" title="Trimegestone">Trimegestone</a></li></ul> <ul><li>Testosterone derivatives: Estranes: <a href="/wiki/Danazol" title="Danazol">Danazol</a></li> <li><a href="/wiki/Dimethisterone" title="Dimethisterone">Dimethisterone</a></li> <li><a href="/wiki/Ethisterone" title="Ethisterone">Ethisterone</a></li></ul> <ul><li>19-Nortestosterone derivatives: Estranes: <a href="/wiki/Allylestrenol" title="Allylestrenol">Allylestrenol</a></li> <li><a href="/wiki/Altrenogest" title="Altrenogest">Altrenogest</a></li> <li><a href="/wiki/Dienogest" title="Dienogest">Dienogest</a></li> <li><a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">Etynodiol diacetate</a></li> <li><a href="/wiki/Lynestrenol" title="Lynestrenol">Lynestrenol</a></li> <li><a href="/wiki/Norethisterone" title="Norethisterone">Norethisterone (norethindrone)</a>#</li> <li><a href="/wiki/Norethisterone_acetate" title="Norethisterone acetate">Norethisterone acetate</a></li> <li><a href="/wiki/Norethisterone_enanthate" title="Norethisterone enanthate">Norethisterone enanthate</a></li> <li><a href="/wiki/Noretynodrel" title="Noretynodrel">Noretynodrel</a></li> <li><a href="/wiki/Norgesterone" title="Norgesterone">Norgesterone</a></li> <li><a href="/wiki/Norgestrienone" title="Norgestrienone">Norgestrienone</a></li> <li><a href="/wiki/Normethandrone" title="Normethandrone">Normethandrone (methylestrenolone)</a></li> <li><a href="/wiki/Norvinisterone" title="Norvinisterone">Norvinisterone</a></li> <li><a href="/wiki/Oxendolone" title="Oxendolone">Oxendolone</a></li> <li><a href="/wiki/Quingestanol_acetate" title="Quingestanol acetate">Quingestanol acetate</a></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a>; Gonanes: <a href="/wiki/Desogestrel" title="Desogestrel">Desogestrel</a></li> <li><a href="/wiki/Etonogestrel" title="Etonogestrel">Etonogestrel</a></li> <li><a href="/wiki/Gestodene" title="Gestodene">Gestodene</a></li> <li><a href="/wiki/Gestrinone" title="Gestrinone">Gestrinone</a></li> <li><a class="mw-selflink selflink">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" /></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 class="mw-selflink selflink">Levonorgestrel</a></li> <li><a href="/wiki/Levonorgestrel_ester" class="mw-redirect" title="Levonorgestrel ester">Levonorgestrel esters</a> (e.g., <a href="/wiki/Levonorgestrel_butanoate" title="Levonorgestrel butanoate">levonorgestrel butanoate</a>)</li> <li><a href="/wiki/Lynestrenol" title="Lynestrenol">Lynestrenol</a></li> <li><a href="/wiki/Lynestrenol_phenylpropionate" title="Lynestrenol phenylpropionate">Lynestrenol phenylpropionate</a></li> <li><a href="/wiki/Metynodiol" title="Metynodiol">Metynodiol</a></li> <li><a href="/wiki/Metynodiol_diacetate" title="Metynodiol diacetate">Metynodiol diacetate</a></li> <li><a href="/wiki/Norelgestromin" title="Norelgestromin">Norelgestromin</a></li> <li><a href="/wiki/Norethisterone" title="Norethisterone">Norethisterone (norethindrone)</a></li> <li><a href="/wiki/Norethisterone_ester" class="mw-redirect" title="Norethisterone ester">Norethisterone esters</a> (e.g., <a href="/wiki/Norethisterone_acetate" title="Norethisterone acetate">norethisterone acetate</a>, <a href="/wiki/Norethisterone_enanthate" title="Norethisterone enanthate">norethisterone enanthate</a>)</li> <li><a href="/wiki/Noretynodrel" title="Noretynodrel">Noretynodrel</a></li> <li><a href="/wiki/Norgesterone" title="Norgesterone">Norgesterone</a></li> <li><a href="/wiki/Norgestimate" title="Norgestimate">Norgestimate</a></li> <li><a href="/wiki/Norgestrel" title="Norgestrel">Norgestrel</a></li> <li><a href="/wiki/Norgestrienone" title="Norgestrienone">Norgestrienone</a></li> <li><a href="/wiki/Norvinisterone" title="Norvinisterone">Norvinisterone</a></li> <li><a href="/wiki/Oxendolone" title="Oxendolone">Oxendolone</a></li> <li><a href="/wiki/Quingestanol" title="Quingestanol">Quingestanol</a></li> <li><a href="/wiki/Quingestanol_acetate" title="Quingestanol acetate">Quingestanol acetate</a></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li> <li><a href="/wiki/Tigestol" title="Tigestol">Tigestol</a></li> <li><a href="/wiki/Tosagestin" title="Tosagestin">Tosagestin</a>; Anabolic–androgenic steroids: <a href="/wiki/11%CE%B2-Methyl-19-nortestosterone" title="11β-Methyl-19-nortestosterone">11β-Methyl-19-nortestosterone</a></li> <li><a href="/wiki/11%CE%B2-Methyl-19-nortestosterone_dodecylcarbonate" title="11β-Methyl-19-nortestosterone dodecylcarbonate">11β-Methyl-19-nortestosterone dodecylcarbonate</a></li> <li><a href="/wiki/19-Nor-5-androstenediol" title="19-Nor-5-androstenediol">19-Nor-5-androstenediol</a></li> <li><a href="/wiki/19-Nor-5-androstenedione" title="19-Nor-5-androstenedione">19-Nor-5-androstenedione</a></li> <li><a href="/wiki/19-Nordehydroepiandrosterone" title="19-Nordehydroepiandrosterone">19-Nordehydroepiandrosterone</a></li> <li><a href="/wiki/Bolandiol" title="Bolandiol">Bolandiol</a></li> <li><a href="/wiki/Bolandiol_dipropionate" title="Bolandiol dipropionate">Bolandiol dipropionate</a></li> <li><a href="/wiki/Bolandione" title="Bolandione">Bolandione</a></li> <li><a href="/wiki/Dimethisterone" title="Dimethisterone">Dimethisterone</a></li> <li><a href="/wiki/Dienedione" title="Dienedione">Dienedione</a></li> <li><a href="/wiki/Dienolone" title="Dienolone">Dienolone</a></li> <li><a href="/wiki/Dimethandrolone" title="Dimethandrolone">Dimethandrolone</a></li> <li><a href="/wiki/Dimethandrolone_buciclate" title="Dimethandrolone buciclate">Dimethandrolone buciclate</a></li> <li><a href="/wiki/Dimethandrolone_dodecylcarbonate" title="Dimethandrolone dodecylcarbonate">Dimethandrolone dodecylcarbonate</a></li> <li><a href="/wiki/Dimethandrolone_undecanoate" title="Dimethandrolone undecanoate">Dimethandrolone undecanoate</a></li> <li><a href="/wiki/Dimethyldienolone" title="Dimethyldienolone">Dimethyldienolone</a></li> <li><a href="/wiki/Dimethyltrienolone" title="Dimethyltrienolone">Dimethyltrienolone</a></li> <li><a href="/wiki/Ethyldienolone" title="Ethyldienolone">Ethyldienolone</a></li> <li><a href="/wiki/Ethylestrenol" title="Ethylestrenol">Ethylestrenol (ethylnandrol)</a></li> <li><a href="/wiki/Methyldienolone" title="Methyldienolone">Methyldienolone</a></li> <li><a href="/wiki/Metribolone" title="Metribolone">Metribolone (R-1881)</a></li> <li><a href="/wiki/Methoxydienone" title="Methoxydienone">Methoxydienone (methoxygonadiene)</a></li> <li><a href="/wiki/Mibolerone" title="Mibolerone">Mibolerone</a></li> <li><a href="/wiki/Nandrolone" title="Nandrolone">Nandrolone</a></li> <li><a href="/wiki/Nandrolone_ester" class="mw-redirect" title="Nandrolone ester">Nandrolone esters</a> (e.g., <a href="/wiki/Nandrolone_decanoate" title="Nandrolone decanoate">nandrolone decanoate</a>, <a href="/wiki/Nandrolone_phenylpropionate" title="Nandrolone phenylpropionate">nandrolone phenylpropionate</a>)</li> <li><a href="/wiki/Norethandrolone" title="Norethandrolone">Norethandrolone</a></li> <li><a href="/wiki/Normethandrone" title="Normethandrone">Normethandrone (methylestrenolone, normethandrolone, normethisterone)</a></li> <li><a href="/wiki/RU-2309" title="RU-2309">RU-2309</a></li> <li><a href="/wiki/Tetrahydrogestrinone" title="Tetrahydrogestrinone">Tetrahydrogestrinone</a></li> <li><a href="/wiki/Trenbolone" title="Trenbolone">Trenbolone (trienolone)</a></li> <li><a href="/wiki/Trenbolone_ester" class="mw-redirect" title="Trenbolone ester">Trenbolone esters</a> (e.g., <a href="/wiki/Trenbolone_acetate" title="Trenbolone acetate">trenbolone acetate</a>, <a href="/wiki/Trenbolone_enanthate" title="Trenbolone enanthate">trenbolone enanthate</a>)</li> <li><a href="/wiki/Trendione" title="Trendione">Trendione</a></li> <li><a href="/wiki/Trestolone" title="Trestolone">Trestolone</a></li> <li><a href="/wiki/Trestolone_acetate" title="Trestolone acetate">Trestolone acetate</a></li></ul> <ul><li>Spirolactone derivatives: <a href="/wiki/Canrenoic_acid" title="Canrenoic acid">Canrenoic acid</a></li> <li><a href="/wiki/Canrenone" title="Canrenone">Canrenone</a></li> <li><a href="/wiki/Drospirenone" title="Drospirenone">Drospirenone</a></li> <li><a href="/wiki/Mespirenone" title="Mespirenone">Mespirenone</a></li> <li><a href="/wiki/Potassium_canrenoate" title="Potassium canrenoate">Potassium canrenoate</a></li> <li><a href="/wiki/Prorenone" title="Prorenone">Prorenone</a></li> <li><a href="/wiki/SC-5233" title="SC-5233">SC-5233 (spirolactone)</a></li> <li><a href="/wiki/SC-8109" title="SC-8109">SC-8109</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/wiki/Spirorenone" title="Spirorenone">Spirorenone</a></li></ul> <ul><li>Nonsteroidal: <a href="/wiki/3,8-Dihydrodiligustilide" title="3,8-Dihydrodiligustilide">3,8-Dihydrodiligustilide</a></li> <li><a href="/wiki/LG-2527" title="LG-2527">LG-2527</a></li> <li><a href="/w/index.php?title=LG-100128&action=edit&redlink=1" class="new" title="LG-100128 (page does not exist)">LG-100128</a></li> <li><a href="/wiki/Riligustilide" title="Riligustilide">Riligustilide</a></li> <li><a href="/w/index.php?title=RWJ-26819&action=edit&redlink=1" class="new" title="RWJ-26819 (page does not exist)">RWJ-26819</a></li> <li><a href="/w/index.php?title=RWJ-49853&action=edit&redlink=1" class="new" title="RWJ-49853 (page does not exist)">RWJ-49853</a></li> <li><a href="/w/index.php?title=RWJ-60130&action=edit&redlink=1" class="new" title="RWJ-60130 (page does not exist)">RWJ-60130</a></li> <li><a href="/wiki/Tanaproget" title="Tanaproget">Tanaproget</a></li> <li><a href="/wiki/ZM-182345" title="ZM-182345">ZM-182345</a></li></ul> <ul><li>Unknown: <a href="/wiki/ORG-47241" title="ORG-47241">ORG-47241</a></li> <li><a href="/wiki/ORG-201745" title="ORG-201745">ORG-201745</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Mixed (<a href="/wiki/Selective_progesterone_receptor_modulators" class="mw-redirect" title="Selective progesterone receptor modulators"><abbr title="Selective progesterone receptor modulators">SPRMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Selective progesterone receptor modulators)</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Steroidal: <a href="/wiki/Dihydroethisterone" class="mw-redirect" title="Dihydroethisterone">Dihydroethisterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydrolevonorgestrel" title="5α-Dihydrolevonorgestrel">5α-Dihydrolevonorgestrel</a></li> <li><a href="/wiki/5%CE%B1-Dihydronorethisterone" title="5α-Dihydronorethisterone">5α-Dihydronorethisterone</a></li> <li><a href="/wiki/Asoprisnil" title="Asoprisnil">Asoprisnil</a></li> <li><a href="/wiki/Asoprisnil_ecamate" title="Asoprisnil ecamate">Asoprisnil ecamate</a></li> <li><a href="/wiki/Guggulsterone" title="Guggulsterone">Guggulsterone</a></li> <li><a href="/w/index.php?title=J1042&action=edit&redlink=1" class="new" title="J1042 (page does not exist)">J1042</a></li> <li><a href="/w/index.php?title=LG-120838&action=edit&redlink=1" class="new" title="LG-120838 (page does not exist)">LG-120838</a></li> <li><a href="/wiki/Metapristone" title="Metapristone">Metapristone (RU-42633)</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone (RU-486)</a></li> <li><a href="/w/index.php?title=ORF-9371&action=edit&redlink=1" class="new" title="ORF-9371 (page does not exist)">ORF-9371</a></li> <li><a href="/wiki/ORF-9326" class="mw-redirect" title="ORF-9326">ORF-9326</a></li> <li><a href="/w/index.php?title=ORG-31710&action=edit&redlink=1" class="new" title="ORG-31710 (page does not exist)">ORG-31710</a></li> <li><a href="/w/index.php?title=ORG-33628&action=edit&redlink=1" class="new" title="ORG-33628 (page does not exist)">ORG-33628</a></li> <li><a href="/w/index.php?title=RMI-12936&action=edit&redlink=1" class="new" title="RMI-12936 (page does not exist)">RMI-12936</a></li> <li><a href="/wiki/Telapristone" title="Telapristone">Telapristone</a></li> <li><a href="/wiki/Ulipristal_acetate" title="Ulipristal acetate">Ulipristal acetate</a></li> <li><a href="/wiki/Vilaprisan" title="Vilaprisan">Vilaprisan</a></li> <li><a href="/w/index.php?title=ZK-137316&action=edit&redlink=1" class="new" title="ZK-137316 (page does not exist)">ZK-137316</a></li></ul> <ul><li>Nonsteroidal: <a href="/wiki/Apigenin" title="Apigenin">Apigenin</a></li> <li><a href="/wiki/Kaempferol" title="Kaempferol">Kaempferol</a></li> <li><a href="/w/index.php?title=LG-120920&action=edit&redlink=1" class="new" title="LG-120920 (page does not exist)">LG-120920</a></li> <li><a href="/wiki/Naringenin" title="Naringenin">Naringenin</a></li> <li><a href="/w/index.php?title=PRA-910&action=edit&redlink=1" class="new" title="PRA-910 (page does not exist)">PRA-910</a></li> <li><a href="/wiki/Syringic_acid" title="Syringic acid">Syringic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Steroidal: <a href="/wiki/Aglepristone" title="Aglepristone">Aglepristone</a></li> <li><a href="/wiki/Lilopristone" title="Lilopristone">Lilopristone</a></li> <li><a href="/wiki/Lonaprisan" title="Lonaprisan">Lonaprisan</a></li> <li><a href="/wiki/Onapristone" title="Onapristone">Onapristone</a></li> <li><a href="/w/index.php?title=ORG-31710&action=edit&redlink=1" class="new" title="ORG-31710 (page does not exist)">ORG-31710</a></li> <li><a href="/w/index.php?title=ORG-31806&action=edit&redlink=1" class="new" title="ORG-31806 (page does not exist)">ORG-31806</a></li> <li><a href="/w/index.php?title=ORG-33628&action=edit&redlink=1" class="new" title="ORG-33628 (page does not exist)">ORG-33628</a></li> <li><a href="/w/index.php?title=RTI_3021%E2%80%93022&action=edit&redlink=1" class="new" title="RTI 3021–022 (page does not exist)">RTI 3021–022</a></li> <li><a href="/wiki/Toripristone" title="Toripristone">Toripristone</a></li> <li><a href="/wiki/Zanoterone" title="Zanoterone">Zanoterone</a></li></ul> <ul><li>Nonsteroidal: <a href="/wiki/Darolutamide" title="Darolutamide">Darolutamide</a></li> <li><a href="/w/index.php?title=LG-001447&action=edit&redlink=1" class="new" title="LG-001447 (page does not exist)">LG-001447</a></li> <li><a href="/w/index.php?title=LG-100127&action=edit&redlink=1" class="new" title="LG-100127 (page does not exist)">LG-100127</a></li> <li><a href="/w/index.php?title=LG-100128&action=edit&redlink=1" class="new" title="LG-100128 (page does not exist)">LG-100128</a></li> <li><a href="/w/index.php?title=LG-120830&action=edit&redlink=1" class="new" title="LG-120830 (page does not exist)">LG-120830</a></li> <li><a href="/w/index.php?title=LG-121046&action=edit&redlink=1" class="new" title="LG-121046 (page does not exist)">LG-121046</a></li> <li><a href="/wiki/Valproic_acid" class="mw-redirect" title="Valproic acid">Valproic acid</a></li> <li><a href="/w/index.php?title=ZM-150271&action=edit&redlink=1" class="new" title="ZM-150271 (page does not exist)">ZM-150271</a></li> <li><a href="/w/index.php?title=ZM-172406&action=edit&redlink=1" class="new" title="ZM-172406 (page does not exist)">ZM-172406</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Membrane_progesterone_receptor" title="Membrane progesterone receptor"><abbr title="Membrane progesterone receptor">mPR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Membrane progesterone receptor (<a href="/wiki/Progestin_and_adipoQ_receptor" title="Progestin and adipoQ receptor"><abbr title="Progestin and adipoQ receptor">PAQR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Progestin and adipoQ receptor)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">5α-Dihydroprogesterone</a></li> <li><a href="/wiki/5%CE%B2-Dihydroprogesterone" title="5β-Dihydroprogesterone">5β-Dihydroprogesterone</a></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycortisone (21-hydroxyprogesterone)</a></li> <li><a href="/wiki/11-Deoxycortisol" title="11-Deoxycortisol">11-Deoxycortisol (17α,21-dihydroxyprogesterone)</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone</a></li> <li><a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Progestogens_and_antiprogestogens" title="Template:Progestogens and antiprogestogens">Progestogens and antiprogestogens</a></dd> <dd><a href="/wiki/Template:Androgen_receptor_modulators" title="Template:Androgen receptor modulators">Androgen receptor modulators</a></dd> <dd><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators">Estrogen receptor modulators</a></dd> <dd><a href="/wiki/List_of_steroidal_progestogens" class="mw-redirect" title="List of steroidal progestogens">List of progestogens</a></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="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 class="mw-selflink selflink">Levonorgestrel</a></li> <li><a href="/wiki/Levonorgestrel_ester" class="mw-redirect" title="Levonorgestrel ester">Levonorgestrel esters</a> (e.g., <a href="/wiki/Levonorgestrel_butanoate" title="Levonorgestrel butanoate">levonorgestrel butanoate</a>)</li> <li><a href="/wiki/Lynestrenol" title="Lynestrenol">Lynestrenol</a> <ul><li><a href="/wiki/Lynestrenol_phenylpropionate" title="Lynestrenol phenylpropionate">Lynestrenol phenylpropionate</a></li></ul></li> <li><a href="/wiki/Norethisterone" title="Norethisterone">Norethisterone</a></li> <li><a href="/wiki/Norethisterone_ester" class="mw-redirect" title="Norethisterone ester">Norethisterone esters</a> (e.g., <a href="/wiki/Norethisterone_acetate" title="Norethisterone acetate">norethisterone acetate</a>, <a href="/wiki/Norethisterone_enanthate" title="Norethisterone enanthate">norethisterone enanthate</a>)</li> <li><a href="/wiki/Norgestrel" title="Norgestrel">Norgestrel</a></li> <li><a href="/wiki/Norgestrienone" title="Norgestrienone">Norgestrienone</a></li> <li><a href="/wiki/Quingestanol" title="Quingestanol">Quingestanol</a> <ul><li><a href="/wiki/Quingestanol_acetate" title="Quingestanol acetate">Quingestanol acetate</a></li></ul></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li></ul> <ul><li>5α-Dihydro-17α-ethynyl-19-nortestosterone derivatives: <a href="/wiki/5%CE%B1-Dihydrolevonorgestrel" title="5α-Dihydrolevonorgestrel">5α-Dihydrolevonorgestrel</a></li> <li><a href="/wiki/5%CE%B1-Dihydronorethisterone" title="5α-Dihydronorethisterone">5α-Dihydronorethisterone</a></li></ul> <ul><li>Progesterone derivatives: <a href="/wiki/6%CE%B1-Methylprogesterone" title="6α-Methylprogesterone">6α-Methylprogesterone</a></li> <li><a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">Medroxyprogesterone acetate</a></li> <li><a href="/wiki/Megestrol_acetate" title="Megestrol acetate">Megestrol acetate</a></li></ul> <ul><li>Others/unsorted: <a href="/wiki/3-Keto-5%CE%B1-abiraterone" title="3-Keto-5α-abiraterone">3-Keto-5α-abiraterone</a></li> <li><a href="/wiki/5%CE%B1-Androstane" class="mw-redirect" title="5α-Androstane">5α-Androstane</a></li> <li><a href="/wiki/Alternariol" title="Alternariol">Alternariol</a></li> <li><a href="/wiki/Cl-4AS-1" title="Cl-4AS-1">Cl-4AS-1</a></li> <li><a href="/wiki/Drupanol" title="Drupanol">Drupanol</a></li> <li><a href="/wiki/Trilostane" title="Trilostane">Trilostane</a></li> <li><a href="/wiki/ZM-182345" title="ZM-182345">ZM-182345</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center"><a href="/wiki/Selective_androgen_receptor_modulator" title="Selective androgen receptor modulator"><abbr title="Selective androgen receptor modulator">SARMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Selective androgen receptor modulator</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Nonsteroidal: <a href="/w/index.php?title=198RL26&action=edit&redlink=1" class="new" title="198RL26 (page does not exist)">198RL26</a></li> <li><a href="/wiki/ACP-105" title="ACP-105">ACP-105</a></li> <li><a href="/wiki/AC-262,536" title="AC-262,536">AC-262,536</a></li> <li><a href="/wiki/Acetothiolutamide" title="Acetothiolutamide">Acetothiolutamide</a></li> <li><a href="/wiki/Acetoxolutamide" title="Acetoxolutamide">Acetoxolutamide</a></li> <li><a href="/wiki/Andarine" title="Andarine">Andarine (acetamidoxolutamide, androxolutamide, GTx-007, S-4)</a></li> <li><a href="/wiki/BMS-564,929" title="BMS-564,929">BMS-564,929</a></li> <li><a href="/w/index.php?title=DTIB&action=edit&redlink=1" class="new" title="DTIB (page does not exist)">DTIB</a></li> <li><a href="/wiki/Enobosarm" title="Enobosarm">Enobosarm (ostarine, MK-2866, GTx-024, S-22)</a></li> <li><a href="/w/index.php?title=FTBU-1&action=edit&redlink=1" class="new" title="FTBU-1 (page does not exist)">FTBU-1</a></li> <li><a href="/wiki/GLPG-0492" title="GLPG-0492">GLPG-0492</a></li> <li><a href="/wiki/GSK2881078" title="GSK2881078">GSK2881078</a></li> <li><a href="/wiki/GSK-4336A" title="GSK-4336A">GSK-4336A</a></li> <li><a href="/w/index.php?title=GSK-8698&action=edit&redlink=1" class="new" title="GSK-8698 (page does not exist)">GSK-8698</a></li> <li><a href="/wiki/LG121071" title="LG121071">LG121071 (LGD-121071)</a></li> <li><a href="/wiki/LGD-2226" title="LGD-2226">LGD-2226</a></li> <li><a href="/wiki/LGD-2941" title="LGD-2941">LGD-2941 (LGD-122941)</a></li> <li><a href="/wiki/LGD-3303" title="LGD-3303">LGD-3303</a></li> <li><a href="/wiki/LGD-4033" class="mw-redirect" title="LGD-4033">LGD-4033</a></li> <li><a href="/wiki/LY305" title="LY305">LY305</a></li> <li><a href="/wiki/JNJ-26146900" title="JNJ-26146900">JNJ-26146900</a></li> <li><a href="/wiki/JNJ-28330835" title="JNJ-28330835">JNJ-28330835</a></li> <li><a href="/wiki/JNJ-37654032" title="JNJ-37654032">JNJ-37654032</a></li> <li><a href="/wiki/OPK-88004" title="OPK-88004">OPK-88004 (LY-2452473, TT-701)</a></li> <li><a href="/w/index.php?title=ORM-11984&action=edit&redlink=1" class="new" title="ORM-11984 (page does not exist)">ORM-11984</a></li> <li><a href="/wiki/PF-06260414" title="PF-06260414">PF-06260414</a></li> <li><a href="/w/index.php?title=R-1_(drug)&action=edit&redlink=1" class="new" title="R-1 (drug) (page does not exist)">R-1</a></li> <li><a href="/wiki/RU-59063" title="RU-59063">RU-59063</a></li> <li><a href="/w/index.php?title=S-1_(drug)&action=edit&redlink=1" class="new" title="S-1 (drug) (page does not exist)">S-1</a></li> <li><a href="/wiki/S-23_(drug)" title="S-23 (drug)">S-23</a></li> <li><a href="/wiki/S-40503" title="S-40503">S-40503</a></li> <li><a href="/w/index.php?title=S-101479&action=edit&redlink=1" class="new" title="S-101479 (page does not exist)">S-101479</a></li> <li><a href="/wiki/Vosilasarm" title="Vosilasarm">Vosilasarm</a></li></ul> <ul><li>Steroidal: <a href="/w/index.php?title=EM-9017&action=edit&redlink=1" class="new" title="EM-9017 (page does not exist)">EM-9017</a></li> <li><a href="/wiki/MK-0773" title="MK-0773">MK-0773</a></li> <li><a href="/wiki/TFM-4AS-1" title="TFM-4AS-1">TFM-4AS-1</a></li> <li><a href="/wiki/YK-11" title="YK-11">YK-11</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Steroidal: <a href="/wiki/7%CE%B1-Thioprogesterone" title="7α-Thioprogesterone">7α-Thioprogesterone</a></li> <li><a href="/wiki/7%CE%B1-Thiospironolactone" title="7α-Thiospironolactone">7α-Thiospironolactone</a></li> <li><a href="/wiki/7%CE%B1-Thiomethylspironolactone" title="7α-Thiomethylspironolactone">7α-Thiomethylspironolactone</a></li> <li><a href="/wiki/11%CE%B1-Hydroxyprogesterone" title="11α-Hydroxyprogesterone">11α-Hydroxyprogesterone</a></li> <li><a href="/wiki/15%CE%B2-Hydroxycyproterone_acetate" title="15β-Hydroxycyproterone acetate">15β-Hydroxycyproterone acetate</a></li> <li><a href="/wiki/Abiraterone" class="mw-redirect" title="Abiraterone">Abiraterone</a></li> <li><a href="/wiki/Abiraterone_acetate" title="Abiraterone acetate">Abiraterone acetate</a></li> <li><a href="/wiki/Allyltestosterone" title="Allyltestosterone">Allyltestosterone</a></li> <li><a href="/wiki/Benorterone" title="Benorterone">Benorterone</a></li> <li><a href="/wiki/BOMT" title="BOMT">BOMT</a></li> <li><a href="/wiki/Canrenoic_acid" title="Canrenoic acid">Canrenoic acid</a></li> <li><a href="/wiki/Canrenone" title="Canrenone">Canrenone</a></li> <li><a href="/wiki/Chlormadinone_acetate" title="Chlormadinone acetate">Chlormadinone acetate</a></li> <li><a href="/wiki/Clascoterone" title="Clascoterone">Clascoterone</a></li> <li><a href="/wiki/Clometerone" title="Clometerone">Clometerone</a></li> <li><a href="/wiki/Cyproheptadine" title="Cyproheptadine">Cyproheptadine</a></li> <li><a href="/wiki/Cyproterone" title="Cyproterone">Cyproterone</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Delanterone" title="Delanterone">Delanterone</a></li> <li><a href="/wiki/Delmadinone_acetate" title="Delmadinone acetate">Delmadinone acetate</a></li> <li><a href="/wiki/Dicirenone" title="Dicirenone">Dicirenone</a></li> <li><a href="/wiki/Dienogest" title="Dienogest">Dienogest</a></li> <li><a href="/wiki/Drospirenone" title="Drospirenone">Drospirenone</a></li> <li><a href="/wiki/DU-41165" title="DU-41165">DU-41165</a></li> <li><a href="/wiki/Edogestrone" title="Edogestrone">Edogestrone</a></li> <li><a href="/w/index.php?title=EM-4350&action=edit&redlink=1" class="new" title="EM-4350 (page does not exist)">EM-4350</a></li> <li><a href="/wiki/EM-5854" title="EM-5854">EM-5854</a></li> <li><a href="/w/index.php?title=EM-5855&action=edit&redlink=1" class="new" title="EM-5855 (page does not exist)">EM-5855</a></li> <li><a href="/w/index.php?title=EM-6537&action=edit&redlink=1" class="new" title="EM-6537 (page does not exist)">EM-6537</a></li> <li><a href="/wiki/Epitestosterone" title="Epitestosterone">Epitestosterone</a></li> <li><a href="/wiki/Galeterone" title="Galeterone">Galeterone</a></li> <li><a href="/wiki/Guggulsterone" title="Guggulsterone">Guggulsterone</a></li> <li><a href="/w/index.php?title=Ludaterone&action=edit&redlink=1" class="new" title="Ludaterone (page does not exist)">Ludaterone</a></li> <li><a href="/wiki/Medrogestone" title="Medrogestone">Medrogestone</a></li> <li><a href="/wiki/Megestrol_acetate" title="Megestrol acetate">Megestrol acetate</a></li> <li><a href="/wiki/Mespirenone" title="Mespirenone">Mespirenone</a></li> <li><a href="/wiki/Metogest" title="Metogest">Metogest</a></li> <li><a href="/wiki/Mexrenone" title="Mexrenone">Mexrenone</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li> <li><a href="/wiki/Nomegestrol_acetate" title="Nomegestrol acetate">Nomegestrol acetate</a></li> <li><a href="/wiki/Nordinone" title="Nordinone">Nordinone</a></li> <li><a href="/wiki/Osaterone" title="Osaterone">Osaterone</a></li> <li><a href="/wiki/Osaterone_acetate" title="Osaterone acetate">Osaterone acetate</a></li> <li><a href="/wiki/Oxendolone" title="Oxendolone">Oxendolone</a></li> <li><a href="/wiki/Potassium_canrenoate" title="Potassium canrenoate">Potassium canrenoate</a></li> <li><a href="/wiki/Promegestone" title="Promegestone">Promegestone</a></li> <li><a href="/wiki/Prorenone" title="Prorenone">Prorenone</a></li> <li><a href="/wiki/Rosterolone" title="Rosterolone">Rosterolone</a></li> <li><a href="/w/index.php?title=RU-15328&action=edit&redlink=1" class="new" title="RU-15328 (page does not exist)">RU-15328</a></li> <li><a href="/wiki/SC-5233" title="SC-5233">SC-5233 (spirolactone)</a></li> <li><a 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="Birth_control_methods322" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Birth_control_methods" title="Template:Birth control methods"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Birth_control_methods" title="Template talk:Birth control methods"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Birth_control_methods" title="Special:EditPage/Template:Birth control methods"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Birth_control_methods322" style="font-size:114%;margin:0 4em"><a href="/wiki/Birth_control" title="Birth control">Birth control</a> methods</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Related topics</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Comparison_of_birth_control_methods" title="Comparison of birth control methods">Comparison of birth control methods</a></li> <li><a href="/wiki/Male_contraceptive" title="Male contraceptive">Male contraceptives</a></li> <li><a href="/wiki/Safe_sex" title="Safe sex">Preventing sexually-transmitted infections</a></li> <li><a href="/wiki/Birth_control#Approval" title="Birth control">Over-the-counter oral contraceptives</a></li> <li><a href="/wiki/Oral_contraceptive_formulations" class="mw-redirect" title="Oral contraceptive formulations">Oral contraceptive formulations</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Long-acting_reversible_contraception" class="mw-redirect" title="Long-acting reversible contraception">Long-acting reversible contraception</a> (LARC)</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Intrauterine_device" title="Intrauterine device">Intrauterine device</a> (<a href="/wiki/Hormonal_IUD" class="mw-redirect" title="Hormonal IUD">Hormonal IUD</a></li> <li><a href="/wiki/Copper_IUD" title="Copper IUD">Copper IUD</a>)</li> <li><a href="/wiki/Contraceptive_implant" title="Contraceptive implant">Contraceptive implant</a> (<a href="/wiki/Etonogestrel_implant" title="Etonogestrel implant">Etonogestrel implant</a>, <a href="/wiki/Levonorgestrel_implant" class="mw-redirect" title="Levonorgestrel implant">Levonorgestrel implant</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sterilization_(medicine)" title="Sterilization (medicine)">Sterilization</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Tubal_ligation" title="Tubal ligation">Tubal ligation</a> (female)</li> <li><a href="/wiki/Vasectomy" title="Vasectomy">Vasectomy</a> (male)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hormonal_contraception" title="Hormonal contraception">Hormonal contraception</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hormonal_contraception#Combined" title="Hormonal contraception">Combined estrogen–progestogen</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/Combined_oral_contraceptive_pill" title="Combined oral contraceptive pill">Oral pill</a></li> <li><a href="/wiki/Extended_cycle_combined_hormonal_contraceptive" title="Extended cycle combined hormonal contraceptive">Extended cycle Pill</a></li> <li><a href="/wiki/Contraceptive_patch" title="Contraceptive patch">Contraceptive patch</a></li> <li><a href="/wiki/Combined_injectable_contraceptive" class="mw-redirect" title="Combined injectable contraceptive">Monthly injections</a></li> <li><a href="/wiki/Ethinylestradiol/etonogestrel" title="Ethinylestradiol/etonogestrel">Vaginal ring</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Progestogen-only_contraception" title="Progestogen-only contraception">Progestogen-only</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Progestogen-only_injectable_contraceptive" title="Progestogen-only injectable contraceptive">Multi-month injections</a></li> <li><a href="/wiki/Progestogen-only_pill" title="Progestogen-only pill">Progestogen-only pill</a></li> <li><a href="/wiki/Progesterone_vaginal_ring" title="Progesterone vaginal ring">Vaginal ring</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Selective_estrogen_receptor_modulator" title="Selective estrogen receptor modulator">SERMs</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/Ormeloxifene" title="Ormeloxifene">Ormeloxifene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Barrier_contraception" class="mw-redirect" title="Barrier contraception">Barrier Methods</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Condom" title="Condom">External condom</a></li> <li><a href="/wiki/Female_condom" title="Female condom">Internal condom</a></li> <li><a href="/wiki/Cervical_cap" title="Cervical cap">Cervical cap</a></li> <li><a href="/wiki/Diaphragm_(birth_control)" title="Diaphragm (birth control)">Diaphragm</a></li> <li><a href="/wiki/Contraceptive_sponge" title="Contraceptive sponge">Contraceptive sponge</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Emergency_Contraception" class="mw-redirect" title="Emergency Contraception">Emergency Contraception</a> (Post-intercourse)</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Copper_IUD#Emergency_contraception" title="Copper IUD">Copper IUD</a></li> <li><a href="/wiki/Ulipristal_acetate" title="Ulipristal acetate">Ulipristal acetate</a></li> <li><a class="mw-selflink-fragment" href="#Emergency_birth_control">Levonorgestrel</a></li> <li><a href="/wiki/Mifepristone#Other" title="Mifepristone">Low-dose mifepristone</a></li> <li><a href="/wiki/Yuzpe_regimen" title="Yuzpe regimen">Yuzpe regimen</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Spermicides" class="mw-redirect" title="Spermicides">Spermicides</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Lactic_acid/citric_acid/potassium_bitartrate" title="Lactic acid/citric acid/potassium bitartrate">Vaginal pH modulation</a></li> <li><a href="/wiki/Nonoxynol-9" title="Nonoxynol-9">Nonoxynol-9</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Behavioral</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Including <a href="/wiki/Penile-vaginal_intercourse" class="mw-redirect" title="Penile-vaginal intercourse">vaginal intercourse</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/Lactational_amenorrhea#Use_as_birth_control" title="Lactational amenorrhea">Breastfeeding method</a></li> <li><a href="/wiki/Calendar-based_contraceptive_methods" title="Calendar-based contraceptive methods">Calendar (rhythm) methods</a></li> <li><a href="/wiki/Fertility_awareness" title="Fertility awareness">Fertility awareness methods</a></li> <li><a href="/wiki/Coitus_interruptus" title="Coitus interruptus">Withdrawal</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Avoiding <a href="/wiki/Penile-vaginal_intercourse" class="mw-redirect" title="Penile-vaginal intercourse">vaginal intercourse</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Non-penetrative_sex" title="Non-penetrative sex">Non-penetrative sex</a></li> <li><a href="/wiki/Sexual_abstinence" title="Sexual abstinence">Abstinence</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Experimental</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Male_contraceptive#Research_into_new_methods" title="Male contraceptive">Male contraceptives in development</a></li></ul> </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 .portal-bar-bordered{padding:0 2em;background-color:#fdfdfd;border:1px solid #a2a9b1;clear:both;margin:1em auto 0}.mw-parser-output .portal-bar-related{font-size:100%;justify-content:flex-start}.mw-parser-output .portal-bar-unbordered{padding:0 1.7em;margin-left:0}.mw-parser-output .portal-bar-header{margin:0 1em 0 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