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<li id="toc-Rings_and_functional_groups" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Rings_and_functional_groups"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>Rings and functional groups</span> </div> </a> <ul id="toc-Rings_and_functional_groups-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Naming_convention" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Naming_convention"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.2</span> <span>Naming convention</span> </div> </a> <ul id="toc-Naming_convention-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Species_distribution" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Species_distribution"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Species distribution</span> </div> </a> <button aria-controls="toc-Species_distribution-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Species distribution subsection</span> </button> <ul id="toc-Species_distribution-sublist" class="vector-toc-list"> <li id="toc-Eukaryotic_and_Prokaryotic" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Eukaryotic_and_Prokaryotic"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Eukaryotic and Prokaryotic</span> </div> </a> <ul id="toc-Eukaryotic_and_Prokaryotic-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Fungal" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Fungal"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>Fungal</span> </div> </a> <ul id="toc-Fungal-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Plant" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Plant"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Plant</span> </div> </a> <ul id="toc-Plant-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Animal" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Animal"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.4</span> <span>Animal</span> </div> </a> <ul id="toc-Animal-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Types" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Types"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Types</span> </div> </a> <button aria-controls="toc-Types-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Types subsection</span> </button> <ul id="toc-Types-sublist" class="vector-toc-list"> <li id="toc-By_function" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#By_function"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>By function</span> </div> </a> <ul id="toc-By_function-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-By_structure" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#By_structure"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>By structure</span> </div> </a> <ul id="toc-By_structure-sublist" class="vector-toc-list"> <li id="toc-Intact_ring_system" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Intact_ring_system"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2.1</span> <span>Intact ring system</span> </div> </a> <ul id="toc-Intact_ring_system-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cleaved,_contracted,_and_expanded_rings" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Cleaved,_contracted,_and_expanded_rings"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2.2</span> <span>Cleaved, contracted, and expanded rings</span> </div> </a> <ul id="toc-Cleaved,_contracted,_and_expanded_rings-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Biological_significance" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Biological_significance"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Biological significance</span> </div> </a> <ul id="toc-Biological_significance-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biosynthesis_and_metabolism" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Biosynthesis_and_metabolism"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Biosynthesis and metabolism</span> </div> </a> <button aria-controls="toc-Biosynthesis_and_metabolism-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Biosynthesis and metabolism subsection</span> </button> <ul id="toc-Biosynthesis_and_metabolism-sublist" class="vector-toc-list"> <li id="toc-Mevalonate_pathway" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Mevalonate_pathway"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Mevalonate pathway</span> </div> </a> <ul id="toc-Mevalonate_pathway-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Steroidogenesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Steroidogenesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span><span>Steroidogenesis</span></span> </div> </a> <ul id="toc-Steroidogenesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Alternative_pathways" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Alternative_pathways"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>Alternative pathways</span> </div> </a> <ul id="toc-Alternative_pathways-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Catabolism_and_excretion" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Catabolism_and_excretion"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Catabolism and excretion</span> </div> </a> <ul id="toc-Catabolism_and_excretion-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Isolation,_structure_determination,_and_methods_of_analysis" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Isolation,_structure_determination,_and_methods_of_analysis"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Isolation, structure determination, and methods of analysis</span> </div> </a> <ul id="toc-Isolation,_structure_determination,_and_methods_of_analysis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Chemical_synthesis" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Chemical_synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Chemical synthesis</span> </div> </a> <button aria-controls="toc-Chemical_synthesis-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Chemical synthesis subsection</span> </button> <ul id="toc-Chemical_synthesis-sublist" class="vector-toc-list"> <li id="toc-Precursors" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Precursors"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.1</span> <span>Precursors</span> </div> </a> <ul id="toc-Precursors-sublist" class="vector-toc-list"> <li id="toc-Semisynthesis" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Semisynthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.1.1</span> <span>Semisynthesis</span> </div> </a> <ul id="toc-Semisynthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Total_synthesis" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Total_synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.1.2</span> <span>Total synthesis</span> </div> </a> <ul id="toc-Total_synthesis-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Research_awards" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Research_awards"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Research awards</span> </div> </a> <ul id="toc-Research_awards-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>See also</span> </div> </a> <ul id="toc-See_also-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"> <span class="vector-toc-numb">11</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Bibliography" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Bibliography"> <div class="vector-toc-text"> <span class="vector-toc-numb">12</span> <span>Bibliography</span> </div> </a> <ul id="toc-Bibliography-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </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"><span class="mw-page-title-main">Steroid</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 75 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-75" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">75 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Stero%C3%AFed" title="Steroïed – Afrikaans" lang="af" hreflang="af" data-title="Steroïed" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%B3%D8%AA%D9%8A%D8%B1%D9%88%D9%8A%D8%AF" title="ستيرويد – Arabic" lang="ar" hreflang="ar" data-title="ستيرويد" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-as mw-list-item"><a href="https://as.wikipedia.org/wiki/%E0%A6%B7%E0%A7%8D%E0%A6%9F%E0%A7%87%E0%A7%B0%E0%A6%87%E0%A6%A1" title="ষ্টেৰইড – Assamese" lang="as" hreflang="as" data-title="ষ্টেৰইড" data-language-autonym="অসমীয়া" data-language-local-name="Assamese" class="interlanguage-link-target"><span>অসমীয়া</span></a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/Esteroide" title="Esteroide – Asturian" lang="ast" hreflang="ast" data-title="Esteroide" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target"><span>Asturianu</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Steroidl%C9%99r" title="Steroidlər – Azerbaijani" lang="az" hreflang="az" data-title="Steroidlər" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%B8%E0%A7%8D%E0%A6%9F%E0%A7%87%E0%A6%B0%E0%A6%AF%E0%A6%BC%E0%A7%87%E0%A6%A1" title="স্টেরয়েড – Bangla" lang="bn" hreflang="bn" data-title="স্টেরয়েড" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%A1%D1%82%D1%8D%D1%80%D0%BE%D1%96%D0%B4%D1%8B" title="Стэроіды – Belarusian" lang="be" hreflang="be" data-title="Стэроіды" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-be-x-old mw-list-item"><a href="https://be-tarask.wikipedia.org/wiki/%D0%A1%D1%82%D1%8D%D1%80%D0%BE%D1%96%D0%B4%D1%8B" title="Стэроіды – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Стэроіды" data-language-autonym="Беларуская (тарашкевіца)" data-language-local-name="Belarusian (Taraškievica orthography)" class="interlanguage-link-target"><span>Беларуская (тарашкевіца)</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%A1%D1%82%D0%B5%D1%80%D0%BE%D0%B8%D0%B4" title="Стероид – Bulgarian" lang="bg" hreflang="bg" data-title="Стероид" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Steroidogeneza" title="Steroidogeneza – Bosnian" lang="bs" hreflang="bs" data-title="Steroidogeneza" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Esteroide" title="Esteroide – Catalan" lang="ca" hreflang="ca" data-title="Esteroide" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cv mw-list-item"><a href="https://cv.wikipedia.org/wiki/%D0%A1%D1%82%D0%B5%D1%80%D0%BE%D0%B8%D0%B4%D1%81%D0%B5%D0%BC" title="Стероидсем – Chuvash" lang="cv" hreflang="cv" data-title="Стероидсем" data-language-autonym="Чӑвашла" data-language-local-name="Chuvash" class="interlanguage-link-target"><span>Чӑвашла</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Steroidy" title="Steroidy – Czech" lang="cs" hreflang="cs" data-title="Steroidy" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Steroid" title="Steroid – Welsh" lang="cy" hreflang="cy" data-title="Steroid" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Steroid" title="Steroid – Danish" lang="da" hreflang="da" data-title="Steroid" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Steroide" title="Steroide – German" lang="de" hreflang="de" data-title="Steroide" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Steroidid" title="Steroidid – Estonian" lang="et" hreflang="et" data-title="Steroidid" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A3%CF%84%CE%B5%CF%81%CE%BF%CE%B5%CE%B9%CE%B4%CE%AD%CF%82" title="Στεροειδές – Greek" lang="el" hreflang="el" data-title="Στεροειδές" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Esteroide" title="Esteroide – Spanish" lang="es" hreflang="es" data-title="Esteroide" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Steroido" title="Steroido – Esperanto" lang="eo" hreflang="eo" data-title="Steroido" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Esteroide" title="Esteroide – Basque" lang="eu" hreflang="eu" data-title="Esteroide" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%D8%B3%D8%AA%D8%B1%D9%88%D8%A6%DB%8C%D8%AF" title="استروئید – Persian" lang="fa" hreflang="fa" data-title="استروئید" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/St%C3%A9ro%C3%AFde" title="Stéroïde – French" lang="fr" hreflang="fr" data-title="Stéroïde" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/St%C3%A9ar%C3%B3ideach" title="Stéaróideach – Irish" lang="ga" hreflang="ga" data-title="Stéaróideach" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Esteroide" title="Esteroide – Galician" lang="gl" hreflang="gl" data-title="Esteroide" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%8A%A4%ED%85%8C%EB%A1%9C%EC%9D%B4%EB%93%9C" title="스테로이드 – Korean" lang="ko" hreflang="ko" data-title="스테로이드" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%8D%D5%BF%D5%A5%D6%80%D5%B8%D5%AB%D5%A4%D5%B6%D5%A5%D6%80" title="Ստերոիդներ – Armenian" lang="hy" hreflang="hy" data-title="Ստերոիդներ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%B8%E0%A5%8D%E0%A4%9F%E0%A5%87%E0%A4%B0%E0%A5%89%E0%A4%AF%E0%A4%A1" title="स्टेरॉयड – Hindi" lang="hi" hreflang="hi" data-title="स्टेरॉयड" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Steroidi" title="Steroidi – Croatian" lang="hr" hreflang="hr" data-title="Steroidi" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Steroid" title="Steroid – Indonesian" lang="id" hreflang="id" data-title="Steroid" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-is mw-list-item"><a href="https://is.wikipedia.org/wiki/Sterar" title="Sterar – Icelandic" lang="is" hreflang="is" data-title="Sterar" data-language-autonym="Íslenska" data-language-local-name="Icelandic" class="interlanguage-link-target"><span>Íslenska</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Steroide" title="Steroide – Italian" lang="it" hreflang="it" data-title="Steroide" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A1%D7%98%D7%A8%D7%95%D7%90%D7%99%D7%93" title="סטרואיד – Hebrew" lang="he" hreflang="he" data-title="סטרואיד" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-jv mw-list-item"><a href="https://jv.wikipedia.org/wiki/Steroid" title="Steroid – Javanese" lang="jv" hreflang="jv" data-title="Steroid" data-language-autonym="Jawa" data-language-local-name="Javanese" class="interlanguage-link-target"><span>Jawa</span></a></li><li class="interlanguage-link interwiki-kn mw-list-item"><a href="https://kn.wikipedia.org/wiki/%E0%B2%B8%E0%B3%8D%E0%B2%9F%E0%B3%80%E0%B2%B0%E0%B2%BE%E0%B2%AF%E0%B3%8D%E0%B2%A1%E0%B3%8D" title="ಸ್ಟೀರಾಯ್ಡ್ – Kannada" lang="kn" hreflang="kn" data-title="ಸ್ಟೀರಾಯ್ಡ್" data-language-autonym="ಕನ್ನಡ" data-language-local-name="Kannada" class="interlanguage-link-target"><span>ಕನ್ನಡ</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%A1%E1%83%A2%E1%83%94%E1%83%A0%E1%83%9D%E1%83%98%E1%83%93%E1%83%94%E1%83%91%E1%83%98" title="სტეროიდები – Georgian" lang="ka" hreflang="ka" data-title="სტეროიდები" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%A1%D1%82%D0%B5%D1%80%D0%BE%D0%B8%D0%B4%D1%82%D0%B0%D1%80" title="Стероидтар – Kazakh" lang="kk" hreflang="kk" data-title="Стероидтар" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-sw mw-list-item"><a href="https://sw.wikipedia.org/wiki/Steroidi" title="Steroidi – Swahili" lang="sw" hreflang="sw" data-title="Steroidi" data-language-autonym="Kiswahili" data-language-local-name="Swahili" class="interlanguage-link-target"><span>Kiswahili</span></a></li><li class="interlanguage-link interwiki-ht mw-list-item"><a href="https://ht.wikipedia.org/wiki/Estewoyid" title="Estewoyid – Haitian Creole" lang="ht" hreflang="ht" data-title="Estewoyid" data-language-autonym="Kreyòl ayisyen" data-language-local-name="Haitian Creole" class="interlanguage-link-target"><span>Kreyòl ayisyen</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%A1%D1%82%D0%B5%D1%80%D0%BE%D0%B8%D0%B4%D0%B4%D0%B5%D1%80" title="Стероиддер – Kyrgyz" lang="ky" hreflang="ky" data-title="Стероиддер" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Stero%C4%ABdi" title="Steroīdi – Latvian" lang="lv" hreflang="lv" data-title="Steroīdi" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Steroidai" title="Steroidai – Lithuanian" lang="lt" hreflang="lt" data-title="Steroidai" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Szteroidok" title="Szteroidok – Hungarian" lang="hu" hreflang="hu" data-title="Szteroidok" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%A1%D1%82%D0%B5%D1%80%D0%BE%D0%B8%D0%B4" title="Стероид – Macedonian" lang="mk" hreflang="mk" data-title="Стероид" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Steroid" title="Steroid – Malay" lang="ms" hreflang="ms" data-title="Steroid" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Stero%C3%AFde" title="Steroïde – Dutch" lang="nl" hreflang="nl" data-title="Steroïde" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%B9%E3%83%86%E3%83%AD%E3%82%A4%E3%83%89" title="ステロイド – Japanese" lang="ja" hreflang="ja" data-title="ステロイド" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Steroid" title="Steroid – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Steroid" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Steroid" title="Steroid – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Steroid" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Estero%C3%AFde" title="Esteroïde – Occitan" lang="oc" hreflang="oc" data-title="Esteroïde" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Steroidy" title="Steroidy – Polish" lang="pl" hreflang="pl" data-title="Steroidy" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Esteroide" title="Esteroide – Portuguese" lang="pt" hreflang="pt" data-title="Esteroide" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Steroid" title="Steroid – Romanian" lang="ro" hreflang="ro" data-title="Steroid" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-rue mw-list-item"><a href="https://rue.wikipedia.org/wiki/%D0%A1%D1%82%D0%B5%D1%80%D0%BE%D0%B8%D0%B4%D1%8B" title="Стероиды – Rusyn" lang="rue" hreflang="rue" data-title="Стероиды" data-language-autonym="Русиньскый" data-language-local-name="Rusyn" class="interlanguage-link-target"><span>Русиньскый</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A1%D1%82%D0%B5%D1%80%D0%BE%D0%B8%D0%B4%D1%8B" title="Стероиды – Russian" lang="ru" hreflang="ru" data-title="Стероиды" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Steroid" title="Steroid – Simple English" lang="en-simple" hreflang="en-simple" data-title="Steroid" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Steroid" title="Steroid – Slovak" lang="sk" hreflang="sk" data-title="Steroid" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Steroid" title="Steroid – Slovenian" lang="sl" hreflang="sl" data-title="Steroid" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%A1%D1%82%D0%B5%D1%80%D0%BE%D0%B8%D0%B4" title="Стероид – Serbian" lang="sr" hreflang="sr" data-title="Стероид" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Steroid" title="Steroid – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Steroid" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-su mw-list-item"><a href="https://su.wikipedia.org/wiki/St%C3%A9roid" title="Stéroid – Sundanese" lang="su" hreflang="su" data-title="Stéroid" data-language-autonym="Sunda" data-language-local-name="Sundanese" class="interlanguage-link-target"><span>Sunda</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Steroidit" title="Steroidit – Finnish" lang="fi" hreflang="fi" data-title="Steroidit" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Steroid" title="Steroid – Swedish" lang="sv" hreflang="sv" data-title="Steroid" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tt mw-list-item"><a href="https://tt.wikipedia.org/wiki/%D0%A1%D1%82%D0%B5%D1%80%D0%BE%D0%B8%D0%B4%D0%BB%D0%B0%D1%80" title="Стероидлар – Tatar" lang="tt" hreflang="tt" data-title="Стероидлар" data-language-autonym="Татарча / tatarça" data-language-local-name="Tatar" class="interlanguage-link-target"><span>Татарча / tatarça</span></a></li><li class="interlanguage-link interwiki-te mw-list-item"><a href="https://te.wikipedia.org/wiki/%E0%B0%B8%E0%B1%8D%E0%B0%9F%E0%B1%86%E0%B0%B0%E0%B0%BE%E0%B0%AF%E0%B0%BF%E0%B0%A1%E0%B1%8D" title="స్టెరాయిడ్ – Telugu" lang="te" hreflang="te" data-title="స్టెరాయిడ్" data-language-autonym="తెలుగు" data-language-local-name="Telugu" class="interlanguage-link-target"><span>తెలుగు</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%AA%E0%B9%80%E0%B8%95%E0%B8%AD%E0%B8%A3%E0%B8%AD%E0%B8%A2%E0%B8%94%E0%B9%8C" title="สเตอรอยด์ – Thai" lang="th" hreflang="th" data-title="สเตอรอยด์" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Steroid" title="Steroid – Turkish" lang="tr" hreflang="tr" data-title="Steroid" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A1%D1%82%D0%B5%D1%80%D0%BE%D1%97%D0%B4%D0%B8" title="Стероїди – Ukrainian" lang="uk" hreflang="uk" data-title="Стероїди" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%D8%B3%D9%B9%DB%8C%D8%B1%D8%A7%D8%A6%DB%8C%DA%88" title="سٹیرائیڈ – Urdu" lang="ur" hreflang="ur" data-title="سٹیرائیڈ" data-language-autonym="اردو" data-language-local-name="Urdu" class="interlanguage-link-target"><span>اردو</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Steroid" title="Steroid – Vietnamese" lang="vi" hreflang="vi" data-title="Steroid" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-war mw-list-item"><a href="https://war.wikipedia.org/wiki/Steroid" title="Steroid – Waray" lang="war" hreflang="war" data-title="Steroid" data-language-autonym="Winaray" data-language-local-name="Waray" class="interlanguage-link-target"><span>Winaray</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E7%94%BE%E4%BD%93" title="甾体 – Wu" lang="wuu" hreflang="wuu" data-title="甾体" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-yi mw-list-item"><a href="https://yi.wikipedia.org/wiki/%D7%A1%D7%98%D7%A2%D7%A8%D7%95%D7%99%D7%93" title="סטערויד – Yiddish" lang="yi" hreflang="yi" data-title="סטערויד" data-language-autonym="ייִדיש" data-language-local-name="Yiddish" class="interlanguage-link-target"><span>ייִדיש</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E9%A1%9E%E5%9B%BA%E9%86%87" title="類固醇 – Cantonese" lang="yue" hreflang="yue" data-title="類固醇" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E7%94%BE%E4%BD%93" title="甾体 – Chinese" lang="zh" hreflang="zh" data-title="甾体" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q177911#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></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 class="vector-menu-content-list"> <li id="ca-nstab-main" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Steroid" title="View the content page [c]" accesskey="c"><span>Article</span></a></li><li id="ca-talk" class="vector-tab-noicon mw-list-item"><a href="/wiki/Talk:Steroid" rel="discussion" title="Discuss improvements to the content page 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							cdx-button--size-medium cdx-button--icon-only cdx-dialog__header__close-button" aria-label="Close" onclick="document.getElementById("mw-fr-revision-details").style.display = "none";" type="submit"><span class="cdx-icon cdx-icon--medium
							cdx-fr-css-icon--close"></span></button></header><div class="cdx-dialog__body">This is the <a href="/wiki/Wikipedia:Pending_changes" title="Wikipedia:Pending changes">latest accepted revision</a>, <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:Log&type=review&page=Special:Badtitle/Message">reviewed</a> on <i>18 November 2024</i>.</div></div><div tabindex="0"></div></div></div></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Polycyclic organic compound having sterane as a core structure</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">This article is about the family of polycyclic compounds. For the drugs, also used as performance-enhancing substances, see <a href="/wiki/Anabolic_steroid" title="Anabolic steroid">Anabolic steroid</a>. For the scientific journal, see <a href="/wiki/Steroids_(journal)" title="Steroids (journal)">Steroids (journal)</a>. For the Death Grips EP, see <a href="/wiki/Steroids_(Crouching_Tiger_Hidden_Gabber_Megamix)" title="Steroids (Crouching Tiger Hidden Gabber Megamix)">Steroids (Crouching Tiger Hidden Gabber Megamix)</a>.</div> <p class="mw-empty-elt"> </p> <figure class="mw-default-size mw-halign-right skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Trimethyl_steroid-nomenclature.svg" class="mw-file-description"><img alt="Complex chemical diagram" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Trimethyl_steroid-nomenclature.svg/220px-Trimethyl_steroid-nomenclature.svg.png" decoding="async" width="220" height="168" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Trimethyl_steroid-nomenclature.svg/330px-Trimethyl_steroid-nomenclature.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Trimethyl_steroid-nomenclature.svg/440px-Trimethyl_steroid-nomenclature.svg.png 2x" data-file-width="427" data-file-height="326" /></a><figcaption>Structure of 24-ethyl-<a href="/wiki/Lanostane" title="Lanostane">lanostane</a>, a prototypical steroid with 32 carbon atoms. Its core ring system (ABCD), composed of 17 carbon atoms, is shown with <a href="/wiki/IUPAC" class="mw-redirect" title="IUPAC">IUPAC</a>-approved ring lettering and atom numbering.<sup id="cite_ref-IUPAC_steroids_1-0" class="reference"><a href="#cite_note-IUPAC_steroids-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 1785f">: 1785f </span></sup></figcaption></figure><p>A <b>steroid</b> is an <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> with four <a href="/wiki/Fused_compound" class="mw-redirect" title="Fused compound">fused</a> rings (designated A, B, C, and D) arranged in a specific <a href="/wiki/Molecular_configuration" title="Molecular configuration">molecular configuration</a>. </p><p>Steroids have two principal biological functions: as important components of <a href="/wiki/Cell_membrane" title="Cell membrane">cell membranes</a> that alter <a href="/wiki/Membrane_fluidity" title="Membrane fluidity">membrane fluidity</a>; and as <a href="/wiki/Signal_transduction" title="Signal transduction">signaling molecules</a>. Examples include the <a href="/wiki/Lipid" title="Lipid">lipid</a> <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a>, sex hormones <a href="/wiki/Estradiol" title="Estradiol">estradiol</a> and <a href="/wiki/Testosterone" title="Testosterone">testosterone</a>,<sup id="cite_ref-Lednicer_2011_2-0" class="reference"><a href="#cite_note-Lednicer_2011-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 10–19">: 10–19 </span></sup> <a href="/wiki/Anabolic_steroids" class="mw-redirect" title="Anabolic steroids">anabolic steroids</a>, and the <a href="/wiki/Anti-inflammatory" title="Anti-inflammatory">anti-inflammatory</a> corticosteroid drug <a href="/wiki/Dexamethasone" title="Dexamethasone">dexamethasone</a>.<sup id="cite_ref-pmid16236742_3-0" class="reference"><a href="#cite_note-pmid16236742-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Hundreds of steroids are found in <a href="/wiki/Fungus" title="Fungus">fungi</a>, <a href="/wiki/Plant" title="Plant">plants</a>, and <a href="/wiki/Animal" title="Animal">animals</a>. All steroids are manufactured in cells from the <a href="/wiki/Sterols" class="mw-redirect" title="Sterols">sterols</a> <a href="/wiki/Lanosterol" title="Lanosterol">lanosterol</a> (<a href="/wiki/Opisthokonts" class="mw-redirect" title="Opisthokonts">opisthokonts</a>) or <a href="/wiki/Cycloartenol" title="Cycloartenol">cycloartenol</a> (plants). Lanosterol and cycloartenol are derived from the <a href="/wiki/Cyclic_compound" title="Cyclic compound">cyclization</a> of the <a href="/wiki/Triterpene" title="Triterpene">triterpene</a> <a href="/wiki/Squalene" title="Squalene">squalene</a>.<sup id="cite_ref-urlLanosterol_biosynthesis_4-0" class="reference"><a href="#cite_note-urlLanosterol_biosynthesis-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>Steroids are named after the steroid <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a><sup id="cite_ref-Harper-Sterol_5-0" class="reference"><a href="#cite_note-Harper-Sterol-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> which was first described in gall stones from <a href="/wiki/Ancient_Greek" title="Ancient Greek">Ancient Greek</a> <i>chole-</i> '<a href="/wiki/Bile" title="Bile">bile</a>' and <i>stereos</i> 'solid'.<sup id="cite_ref-Chevreul-1815_6-0" class="reference"><a href="#cite_note-Chevreul-1815-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Arago-1816_7-0" class="reference"><a href="#cite_note-Arago-1816-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-R-2.4.1_Fusion_nomenclature_8-0" class="reference"><a href="#cite_note-R-2.4.1_Fusion_nomenclature-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>The steroid nucleus (<a href="/wiki/Parent_structure" title="Parent structure">core structure</a>) is called <a href="/wiki/Gonane" title="Gonane">gonane</a> (cyclopentanoperhydrophenanthrene).<sup id="cite_ref-pmid36677830_9-0" class="reference"><a href="#cite_note-pmid36677830-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> It is typically composed of seventeen <a href="/wiki/Carbon" title="Carbon">carbon</a> atoms, bonded in four fused rings: three six-member <a href="/wiki/Cyclohexane" title="Cyclohexane">cyclohexane</a> rings (rings A, B and C in the first illustration) and one five-member <a href="/wiki/Cyclopentane" title="Cyclopentane">cyclopentane</a> ring (the D ring). Steroids vary by the <a href="/wiki/Functional_groups" class="mw-redirect" title="Functional groups">functional groups</a> attached to this four-ring core and by the <a href="/wiki/Oxidation_state" title="Oxidation state">oxidation state</a> of the rings. <a href="/wiki/Sterol" title="Sterol">Sterols</a> are forms of steroids with a <a href="/wiki/Hydroxy_group" title="Hydroxy group">hydroxy group</a> at position three and a skeleton derived from <a href="/wiki/Cholestane" title="Cholestane">cholestane</a>.<sup id="cite_ref-IUPAC_steroids_1-1" class="reference"><a href="#cite_note-IUPAC_steroids-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 1785f">: 1785f </span></sup><sup id="cite_ref-Hill-1991_10-0" class="reference"><a href="#cite_note-Hill-1991-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Steroids can also be more radically modified, such as by changes to the ring structure, for example, <a href="/wiki/Bond_cleavage" title="Bond cleavage">cutting</a> one of the rings. Cutting Ring B produces <a href="/wiki/Secosteroid" title="Secosteroid">secosteroids</a> one of which is <a href="/wiki/Vitamin_D3" class="mw-redirect" title="Vitamin D3">vitamin D<sub>3</sub></a>. </p> <style data-mw-deduplicate="TemplateStyles:r1237032888/mw-parser-output/.tmulti">.mw-parser-output .tmulti .multiimageinner{display:flex;flex-direction:column}.mw-parser-output .tmulti .trow{display:flex;flex-direction:row;clear:left;flex-wrap:wrap;width:100%;box-sizing:border-box}.mw-parser-output .tmulti .tsingle{margin:1px;float:left}.mw-parser-output .tmulti .theader{clear:both;font-weight:bold;text-align:center;align-self:center;background-color:transparent;width:100%}.mw-parser-output .tmulti .thumbcaption{background-color:transparent}.mw-parser-output .tmulti .text-align-left{text-align:left}.mw-parser-output .tmulti .text-align-right{text-align:right}.mw-parser-output .tmulti .text-align-center{text-align:center}@media all and (max-width:720px){.mw-parser-output .tmulti .thumbinner{width:100%!important;box-sizing:border-box;max-width:none!important;align-items:center}.mw-parser-output .tmulti .trow{justify-content:center}.mw-parser-output .tmulti .tsingle{float:none!important;max-width:100%!important;box-sizing:border-box;text-align:center}.mw-parser-output .tmulti .tsingle .thumbcaption{text-align:left}.mw-parser-output .tmulti .trow>.thumbcaption{text-align:center}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .tmulti .multiimageinner img{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .tmulti .multiimageinner img{background-color:white}}</style><div class="thumb tmulti tright"><div class="thumbinner multiimageinner" style="width:408px;max-width:408px"><div class="trow"><div class="tsingle" style="width:202px;max-width:202px"><div class="thumbimage"><span typeof="mw:File"><a href="/wiki/File:5alpha-Dihydroprogesterone_3D_spacefill.png" class="mw-file-description"><img alt="Filled-in diagram of a steroid" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/5alpha-Dihydroprogesterone_3D_spacefill.png/200px-5alpha-Dihydroprogesterone_3D_spacefill.png" decoding="async" width="200" height="148" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/5alpha-Dihydroprogesterone_3D_spacefill.png/300px-5alpha-Dihydroprogesterone_3D_spacefill.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3f/5alpha-Dihydroprogesterone_3D_spacefill.png/400px-5alpha-Dihydroprogesterone_3D_spacefill.png 2x" data-file-width="2000" data-file-height="1477" /></a></span></div><div class="thumbcaption">Space-filling representation</div></div><div class="tsingle" style="width:202px;max-width:202px"><div class="thumbimage"><span typeof="mw:File"><a href="/wiki/File:5alpha-Dihydroprogesterone_3D_ball.png" class="mw-file-description"><img alt="Ball-and-stick diagram of the same steroid" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e4/5alpha-Dihydroprogesterone_3D_ball.png/200px-5alpha-Dihydroprogesterone_3D_ball.png" decoding="async" width="200" height="136" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e4/5alpha-Dihydroprogesterone_3D_ball.png/300px-5alpha-Dihydroprogesterone_3D_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e4/5alpha-Dihydroprogesterone_3D_ball.png/400px-5alpha-Dihydroprogesterone_3D_ball.png 2x" data-file-width="2000" data-file-height="1362" /></a></span></div><div class="thumbcaption">Ball-and-stick representation</div></div></div><div class="trow" style="display:flex"><div class="thumbcaption">5α-dihydroprogesterone (5α-DHP), a steroid. The shape of the four rings of most steroids is illustrated (carbon atoms in black, oxygens in red and hydrogens in grey). The <a href="/wiki/Nonpolar" class="mw-redirect" title="Nonpolar">nonpolar</a> "slab" of <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbon</a> in the middle (grey, black) and the <a href="/wiki/Ketone" title="Ketone">polar</a> groups at opposing ends (red) are common features of natural steroids. <a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">5α-DHP</a> is an endogenous <a href="/wiki/Steroid_hormone" title="Steroid hormone">steroid hormone</a> and a <a href="/wiki/Biosynthesis" title="Biosynthesis">biosynthetic</a> intermediate.</div></div></div></div> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Nomenclature">Nomenclature</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Steroid&action=edit&section=1" title="Edit section: Nomenclature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Rings_and_functional_groups">Rings and functional groups</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Steroid&action=edit&section=2" title="Edit section: Rings and functional groups"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Gonane" title="Gonane">Gonane</a> and <a href="/wiki/Sterane" title="Sterane">Sterane</a></div> <figure class="skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Gonane.png" class="mw-file-description"><img alt="Chemical diagram" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Gonane.png/120px-Gonane.png" decoding="async" width="120" height="102" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Gonane.png/180px-Gonane.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Gonane.png/240px-Gonane.png 2x" data-file-width="1081" data-file-height="917" /></a><figcaption><a href="/wiki/Gonane" title="Gonane">Gonane</a>, the simplest steroid, consisting only of the common steroid nucleus</figcaption></figure> <figure class="mw-default-size skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:5alpha5betaSteroidIUPAC.png" class="mw-file-description"><img alt="Chemical diagram" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/5alpha5betaSteroidIUPAC.png/220px-5alpha5betaSteroidIUPAC.png" decoding="async" width="220" height="73" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/5alpha5betaSteroidIUPAC.png/330px-5alpha5betaSteroidIUPAC.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8b/5alpha5betaSteroidIUPAC.png/440px-5alpha5betaSteroidIUPAC.png 2x" data-file-width="630" data-file-height="208" /></a><figcaption>Steroid 5α and 5β <a href="/wiki/Stereoisomerism" title="Stereoisomerism">stereoisomers</a><sup id="cite_ref-IUPAC_steroids_1-2" class="reference"><a href="#cite_note-IUPAC_steroids-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 1786f">: 1786f </span></sup></figcaption></figure> <p><a href="/wiki/Gonane" title="Gonane">Gonane</a>, also known as steran or cyclopentanoperhydrophenanthrene, the simplest steroid and the nucleus of all steroids and sterols,<sup id="cite_ref-Rogozkin1991_11-0" class="reference"><a href="#cite_note-Rogozkin1991-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Urich1994_12-0" class="reference"><a href="#cite_note-Urich1994-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> is composed of seventeen <a href="/wiki/Carbon" title="Carbon">carbon</a> atoms in carbon-carbon bonds forming four <a href="/wiki/Fused_compound" class="mw-redirect" title="Fused compound">fused rings</a> in a <a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">three-dimensional shape</a>. The three <a href="/wiki/Cyclohexane" title="Cyclohexane">cyclohexane</a> rings (A, B, and C in the first illustration) form the skeleton of a <a href="/wiki/Hydrogenation" title="Hydrogenation">perhydro</a> derivative of <a href="/wiki/Phenanthrene" title="Phenanthrene">phenanthrene</a>. The D ring has a <a href="/wiki/Cyclopentane" title="Cyclopentane">cyclopentane</a> structure. When the two methyl groups and eight carbon <a href="/wiki/Side_chain" title="Side chain">side chains</a> (at C-17, as shown for cholesterol) are present, the steroid is said to have a cholestane framework. The two common 5α and 5β stereoisomeric forms of steroids exist because of differences in the side of the largely planar ring system where the hydrogen (H) atom at carbon-5 is attached, which results in a change in steroid A-ring conformation. Isomerisation at the C-21 side chain produces a parallel series of compounds, referred to as isosteroids.<sup id="cite_ref-FOOTNOTEGreep2013_13-0" class="reference"><a href="#cite_note-FOOTNOTEGreep2013-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p><p>Examples of steroid structures are: </p> <div class="skin-invert-image"> <ul class="gallery mw-gallery-traditional"> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Testosteron.svg" class="mw-file-description" title="Testosterone, the principal male sex hormone and an anabolic steroid"><img alt="Chemical diagram" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/ce/Testosteron.svg/120px-Testosteron.svg.png" decoding="async" width="120" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/ce/Testosteron.svg/180px-Testosteron.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/ce/Testosteron.svg/240px-Testosteron.svg.png 2x" data-file-width="512" data-file-height="341" /></a></span></div> <div class="gallerytext"><a href="/wiki/Testosterone" title="Testosterone">Testosterone</a>, the principal male <a href="/wiki/Sex_steroid" class="mw-redirect" title="Sex steroid">sex hormone</a> and an <a href="/wiki/Anabolic_steroid" title="Anabolic steroid">anabolic steroid</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Chols%C3%A4ure.svg" class="mw-file-description" title="Cholic acid, a bile acid, showing the carboxylic acid and additional hydroxyl groups often present"><img alt="Chemical diagram" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/Chols%C3%A4ure.svg/120px-Chols%C3%A4ure.svg.png" decoding="async" width="120" height="63" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/Chols%C3%A4ure.svg/180px-Chols%C3%A4ure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/Chols%C3%A4ure.svg/240px-Chols%C3%A4ure.svg.png 2x" data-file-width="433" data-file-height="228" /></a></span></div> <div class="gallerytext"><a href="/wiki/Cholic_acid" title="Cholic acid">Cholic acid</a>, a <a href="/wiki/Bile_acid" title="Bile acid">bile acid</a>, showing the <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a> and additional <a href="/wiki/Hydroxyl_group" class="mw-redirect" title="Hydroxyl group">hydroxyl groups</a> often present</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Dexamethasone_structure.svg" class="mw-file-description" title="Dexamethasone, a synthetic corticosteroid drug"><img alt="Chemical diagram" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1f/Dexamethasone_structure.svg/120px-Dexamethasone_structure.svg.png" decoding="async" width="120" height="95" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1f/Dexamethasone_structure.svg/180px-Dexamethasone_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1f/Dexamethasone_structure.svg/240px-Dexamethasone_structure.svg.png 2x" data-file-width="512" data-file-height="407" /></a></span></div> <div class="gallerytext"><a href="/wiki/Dexamethasone" title="Dexamethasone">Dexamethasone</a>, a synthetic <a href="/wiki/Corticosteroid" title="Corticosteroid">corticosteroid</a> drug</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Lanosterin.svg" class="mw-file-description" title="Lanosterol, the biosynthetic precursor to animal steroids. The number of carbons (30) indicates its triterpenoid classification."><img alt="Chemical diagram" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f9/Lanosterin.svg/120px-Lanosterin.svg.png" decoding="async" width="120" height="63" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f9/Lanosterin.svg/180px-Lanosterin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f9/Lanosterin.svg/240px-Lanosterin.svg.png 2x" data-file-width="441" data-file-height="230" /></a></span></div> <div class="gallerytext"><a href="/wiki/Lanosterol" title="Lanosterol">Lanosterol</a>, the <a href="/wiki/Biosynthetic" class="mw-redirect" title="Biosynthetic">biosynthetic</a> precursor to animal steroids. The number of carbons (30) indicates its <a href="/wiki/Triterpenoid" class="mw-redirect" title="Triterpenoid">triterpenoid</a> classification.</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Progesteron.svg" class="mw-file-description" title="Progesterone, a steroid hormone involved in the female menstrual cycle, pregnancy, and embryogenesis"><img alt="Chemical diagram" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Progesteron.svg/120px-Progesteron.svg.png" decoding="async" width="120" height="84" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Progesteron.svg/180px-Progesteron.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Progesteron.svg/240px-Progesteron.svg.png 2x" data-file-width="297" data-file-height="209" /></a></span></div> <div class="gallerytext"><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a>, a steroid hormone involved in the female menstrual cycle, pregnancy, and embryogenesis</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Medrogestone.png" class="mw-file-description" title="Medrogestone, a synthetic drug with effects similar to progesterone"><img alt="Chemical diagram" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7e/Medrogestone.png/120px-Medrogestone.png" decoding="async" width="120" height="90" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7e/Medrogestone.png/180px-Medrogestone.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7e/Medrogestone.png/240px-Medrogestone.png 2x" data-file-width="941" data-file-height="706" /></a></span></div> <div class="gallerytext"><a href="/wiki/Medrogestone" title="Medrogestone">Medrogestone</a>, a synthetic drug with effects similar to progesterone</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Sitosterol_structure.svg" class="mw-file-description" title="β-Sitosterol, a plant or phytosterol, with a fully branched hydrocarbon side chain at C-17 and an hydroxyl group at C-3"><img alt="Chemical diagram" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/be/Sitosterol_structure.svg/120px-Sitosterol_structure.svg.png" decoding="async" width="120" height="71" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/be/Sitosterol_structure.svg/180px-Sitosterol_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/be/Sitosterol_structure.svg/240px-Sitosterol_structure.svg.png 2x" data-file-width="1220" data-file-height="720" /></a></span></div> <div class="gallerytext"><a href="/wiki/Beta-Sitosterol" class="mw-redirect" title="Beta-Sitosterol">β-Sitosterol</a>, a plant or <a href="/wiki/Phytosterol" title="Phytosterol">phytosterol</a>, with a fully branched hydrocarbon side chain at C-17 and an hydroxyl group at C-3</div> </li> </ul> </div> <p>In addition to the ring scissions (cleavages), <a href="/wiki/Ring_expansion" class="mw-redirect" title="Ring expansion">expansions</a> and <a href="/wiki/Ring_contraction" class="mw-redirect" title="Ring contraction">contractions</a> (cleavage and reclosing to a larger or smaller rings)—all variations in the carbon-carbon bond framework—steroids can also vary: </p> <ul><li>in the <a href="/wiki/Bond_order" title="Bond order">bond orders</a> within the rings,</li> <li>in the number of methyl groups attached to the ring (and, when present, on the prominent side chain at C17),</li> <li>in the functional groups attached to the rings and side chain, and</li> <li>in the <a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">configuration</a> of groups attached to the rings and chain.<sup id="cite_ref-Lednicer_2011_2-1" class="reference"><a href="#cite_note-Lednicer_2011-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 2–9">: 2–9 </span></sup></li></ul> <p>For instance, <a href="/wiki/Sterol" title="Sterol">sterols</a> such as cholesterol and lanosterol have a <a href="/wiki/Hydroxyl_group" class="mw-redirect" title="Hydroxyl group">hydroxyl group</a> attached at position C-3, while <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> and <a href="/wiki/Progesterone" title="Progesterone">progesterone</a> have a carbonyl (oxo substituent) at C-3. Among these compounds, only <a href="/wiki/Lanosterol" title="Lanosterol">lanosterol</a> has two methyl groups at C-4. Cholesterol which has a C-5 to C-6 double bond, differs from testosterone and progesterone which have a C-4 to C-5 double bond. </p> <table> <tbody><tr valign="top"> <td><figure class="mw-default-size skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Cholesterol_lettering_numbering.svg" class="mw-file-description"><img alt="Chemical diagram" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2e/Cholesterol_lettering_numbering.svg/220px-Cholesterol_lettering_numbering.svg.png" decoding="async" width="220" height="149" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2e/Cholesterol_lettering_numbering.svg/330px-Cholesterol_lettering_numbering.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2e/Cholesterol_lettering_numbering.svg/440px-Cholesterol_lettering_numbering.svg.png 2x" data-file-width="1708" data-file-height="1158" /></a><figcaption><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a>, a <a href="/wiki/Prototype" title="Prototype">prototypical</a> animal sterol. This structural <a href="/wiki/Lipid" title="Lipid">lipid</a> and key steroid <a href="/wiki/Biosynthesis" title="Biosynthesis">biosynthetic</a> precursor.<sup id="cite_ref-IUPAC_steroids_1-3" class="reference"><a href="#cite_note-IUPAC_steroids-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 1785f">: 1785f </span></sup></figcaption></figure> </td> <td><figure class="mw-default-size skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Cholestane.svg" class="mw-file-description"><img alt="Chemical diagram" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cb/Cholestane.svg/220px-Cholestane.svg.png" decoding="async" width="220" height="200" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cb/Cholestane.svg/330px-Cholestane.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cb/Cholestane.svg/440px-Cholestane.svg.png 2x" data-file-width="1340" data-file-height="1220" /></a><figcaption>5α-<a href="/wiki/Cholestane" title="Cholestane">cholestane</a>, a common steroid core</figcaption></figure> </td> <td> </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Naming_convention">Naming convention</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Steroid&action=edit&section=3" title="Edit section: Naming convention"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Almost all biologically relevant steroids can be presented as a derivative of a parent <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a>-like <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbon</a> structure that serves as a <a href="/wiki/Skeletal_formula" title="Skeletal formula">skeleton</a>.<sup id="cite_ref-wj_14-0" class="reference"><a href="#cite_note-wj-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid2606099-skeleton_15-0" class="reference"><a href="#cite_note-pmid2606099-skeleton-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> These parent structures have specific names, such as <a href="/wiki/Pregnane" title="Pregnane">pregnane</a>, <a href="/wiki/Androstane" title="Androstane">androstane</a>, etc. The derivatives carry various <a href="/wiki/Functional_group" title="Functional group">functional groups</a> called suffixes or prefixes after the respective numbers, indicating their position in the steroid nucleus.<sup id="cite_ref-pmid2606099-parent-elisions_16-0" class="reference"><a href="#cite_note-pmid2606099-parent-elisions-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> There are widely used trivial steroid names of natural origin with significant biologic activity, such as <a href="/wiki/Progesterone" title="Progesterone">progesterone</a>, <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> or <a href="/wiki/Cortisol" title="Cortisol">cortisol</a>. Some of these names are defined in The Nomenclature of Steroids.<sup id="cite_ref-pmid2606099-trivial_17-0" class="reference"><a href="#cite_note-pmid2606099-trivial-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> These trivial names can also be used as a base to derive new names, however, by adding prefixes only rather than suffixes, e.g., the steroid <a href="/wiki/17%CE%B1-hydroxyprogesterone" class="mw-redirect" title="17α-hydroxyprogesterone">17α-hydroxyprogesterone</a> has a <a href="/wiki/Hydroxy_group" title="Hydroxy group">hydroxy group</a> (-OH) at position 17 of the steroid nucleus comparing to progesterone. </p><p>The letters α and β<sup id="cite_ref-pmid2606099-rs_18-0" class="reference"><a href="#cite_note-pmid2606099-rs-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> denote absolute <a href="/wiki/Stereochemistry" title="Stereochemistry">stereochemistry</a> at <a href="/wiki/Stereocenter" title="Stereocenter">chiral centers</a>—a specific nomenclature distinct from the <a href="/wiki/R/S_convention" class="mw-redirect" title="R/S convention">R/S convention</a><sup id="cite_ref-norc-rs_19-0" class="reference"><a href="#cite_note-norc-rs-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> of organic chemistry to denote absolute configuration of functional groups, known as <a href="/wiki/Cahn%E2%80%93Ingold%E2%80%93Prelog_priority_rules" title="Cahn–Ingold–Prelog priority rules">Cahn–Ingold–Prelog priority rules</a>. The R/S convention assigns priorities to substituents on a chiral center based on their atomic number. The highest priority group is assigned to the atom with the highest atomic number, and the lowest priority group is assigned to the atom with the lowest atomic number. The molecule is then oriented so that the lowest priority group points away from the viewer, and the remaining three groups are arranged in order of decreasing priority around the chiral center. If this arrangement is clockwise, it is assigned an R configuration; if it is counterclockwise, it is assigned an S configuration.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> In contrast, steroid nomenclature uses α and β to denote stereochemistry at chiral centers. The α and β designations are based on the orientation of substituents relative to each other in a specific ring system. In general, α refers to a substituent that is oriented towards the plane of the ring system, while β refers to a substituent that is oriented away from the plane of the ring system. In steroids drawn from the standard perspective used in this paper, α-bonds are depicted on figures as dashed wedges and β-bonds as solid wedges.<sup id="cite_ref-wj_14-1" class="reference"><a href="#cite_note-wj-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>The name "<a href="/wiki/11-Deoxycortisol" title="11-Deoxycortisol">11-deoxycortisol</a>" is an example of a derived name that uses cortisol as a parent structure without an <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> <a href="/wiki/Atom" title="Atom">atom</a> (hence "deoxy") attached to position 11 (as a part of a hydroxy group).<sup id="cite_ref-wj_14-2" class="reference"><a href="#cite_note-wj-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-norc-deoxy_21-0" class="reference"><a href="#cite_note-norc-deoxy-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> The numbering of positions of <a href="/wiki/Carbon" title="Carbon">carbon</a> atoms in the steroid nucleus is set in a template found in the Nomenclature of Steroids<sup id="cite_ref-pmid2606099-numbering_22-0" class="reference"><a href="#cite_note-pmid2606099-numbering-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> that is used regardless of whether an atom is present in the steroid in question.<sup id="cite_ref-wj_14-3" class="reference"><a href="#cite_note-wj-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Saturated_and_unsaturated_compounds" title="Saturated and unsaturated compounds">Unsaturated</a> carbons (generally, ones that are part of a double bond) in the steroid nucleus are indicated by changing -ane to -ene.<sup id="cite_ref-pmid2606099-unsaturation_23-0" class="reference"><a href="#cite_note-pmid2606099-unsaturation-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> This change was traditionally done in the parent name, adding a prefix to denote the position, with or without Δ (Greek capital delta) which designates unsaturation, for example, 4-pregnene-11β,17α-diol-3,20-dione (also Δ<sup>4</sup>-pregnene-11β,17α-diol-3,20-dione) or <a href="/wiki/4-androstene-3,11-17-trione" class="mw-redirect" title="4-androstene-3,11-17-trione">4-androstene-3,11,17-trione</a> (also Δ<sup>4</sup>-androstene-3,11,17-trione). However, the Nomenclature of Steroids recommends the <a href="/wiki/Locant" title="Locant">locant</a> of a double bond to be always adjacent to the syllable designating the unsaturation, therefore, having it as a suffix rather than a prefix, and without the use of the Δ character, i.e. pregn-4-ene-11β,17α-diol-3,20-dione or <a href="/wiki/Androst-4-ene-3,11-17-trione" class="mw-redirect" title="Androst-4-ene-3,11-17-trione">androst-4-ene-3,11,17-trione</a>. The double bond is designated by the lower-numbered carbon atom, i.e. "Δ<sup>4</sup>-" or "4-ene" means the double bond between positions 4 and 5. The saturation of carbons of a parent steroid can be done by adding "dihydro-" prefix,<sup id="cite_ref-norc_24-0" class="reference"><a href="#cite_note-norc-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> i.e., a saturation of carbons 4 and 5 of testosterone with two <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> atoms is 4,5α-dihydrotestosterone or 4,5β-dihydrotestosterone. Generally, when there is no ambiguity, one number of a hydrogen position from a steroid with a saturated bond may be omitted, leaving only the position of the second hydrogen atom, e.g., <a href="/wiki/5%CE%B1-dihydrotestosterone" class="mw-redirect" title="5α-dihydrotestosterone">5α-dihydrotestosterone</a> or <a href="/wiki/5%CE%B2-Dihydrotestosterone" title="5β-Dihydrotestosterone">5β-dihydrotestosterone</a>. The Δ<sup>5</sup>-steroids are those with a double bond between carbons 5 and 6 and the Δ<sup>4</sup> steroids are those with a double bond between carbons 4 and 5.<sup id="cite_ref-pmid21051590_25-0" class="reference"><a href="#cite_note-pmid21051590-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid2606099-unsaturation_23-1" class="reference"><a href="#cite_note-pmid2606099-unsaturation-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p><p>The abbreviations like "<a href="/wiki/Progesterone" title="Progesterone">P4</a>" for <a href="/wiki/Progesterone" title="Progesterone">progesterone</a> and "<a href="/wiki/Androstenedione" title="Androstenedione">A4</a>" for <a href="/wiki/Androstenedione" title="Androstenedione">androstenedione</a> for refer to Δ<sup>4</sup>-steroids, while "<a href="/wiki/Pregnenolone" title="Pregnenolone">P5</a>" for <a href="/wiki/Pregnenolone" title="Pregnenolone">pregnenolone</a> and "<a href="/wiki/Androstenediol" title="Androstenediol">A5</a>" for <a href="/wiki/Androstenediol" title="Androstenediol">androstenediol</a> refer to Δ<sup>5</sup>-steroids.<sup id="cite_ref-wj_14-4" class="reference"><a href="#cite_note-wj-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>The suffix -ol denotes a <a href="/wiki/Hydroxy_group" title="Hydroxy group">hydroxy group</a>, while the suffix -one denotes an oxo group. When two or three identical groups are attached to the base structure at different positions, the suffix is indicated as -diol or -triol for hydroxy, and -dione or -trione for oxo groups, respectively. For example, <a href="/wiki/5%CE%B1-Pregnane-3%CE%B1,17%CE%B1-diol-20-one" title="5α-Pregnane-3α,17α-diol-20-one">5α-pregnane-3α,17α-diol-20-one</a> has a hydrogen atom at the 5α position (hence the "5α-" prefix), two hydroxy groups (-OH) at the 3α and 17α positions (hence "3α,17α-diol" suffix) and an oxo group (=O) at the position 20 (hence the "20-one" suffix). However, erroneous use of suffixes can be found, e.g., "5α-pregnan-17α-diol-3,11,20-trione"<sup id="cite_ref-google-pregnan17diol_26-0" class="reference"><a href="#cite_note-google-pregnan17diol-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> [<i>sic</i>] — since it has just one hydroxy group (at 17α) rather than two, then the suffix should be -ol, rather than -diol, so that the correct name to be "5α-pregnan-17α-ol-3,11,20-trione". </p><p>According to the rule set in the Nomenclature of Steroids, the terminal "e" in the parent structure name should be elided before the <a href="/wiki/Vowel" title="Vowel">vowel</a> (the presence or absence of a number does not affect such elision).<sup id="cite_ref-wj_14-5" class="reference"><a href="#cite_note-wj-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid2606099-parent-elisions_16-1" class="reference"><a href="#cite_note-pmid2606099-parent-elisions-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> This means, for instance, that if the suffix immediately appended to the parent structure name begins with a vowel, the trailing "e" is removed from that name. An example of such removal is "<a href="/wiki/5%CE%B1-Pregnan-17%CE%B1-ol-3,20-dione" title="5α-Pregnan-17α-ol-3,20-dione">5α-pregnan-17α-ol-3,20-dione</a>", where the last "e" of "<a href="/wiki/Pregnane" title="Pregnane">pregnane</a>" is dropped due to the vowel ("o") at the beginning of the suffix -ol. Some authors incorrectly use this rule, eliding the terminal "e" where it should be kept, or vice versa.<sup id="cite_ref-google-pregnane17ol_27-0" class="reference"><a href="#cite_note-google-pregnane17ol-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p><p>The term "11-oxygenated" refers to the presence of an oxygen atom as an oxo (=O) or hydroxy (-OH) substituent at carbon 11. "Oxygenated" is consistently used within the chemistry of the steroids<sup id="cite_ref-chemster_28-0" class="reference"><a href="#cite_note-chemster-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> since the 1950s.<sup id="cite_ref-pmid13167092_29-0" class="reference"><a href="#cite_note-pmid13167092-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> Some studies use the term "11-oxyandrogens"<sup id="cite_ref-11oxyhs_30-0" class="reference"><a href="#cite_note-11oxyhs-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid35611324_31-0" class="reference"><a href="#cite_note-pmid35611324-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> as an abbreviation for 11-oxygenated androgens, to emphasize that they all have an oxygen atom attached to carbon at position 11.<sup id="cite_ref-pmid32203405_32-0" class="reference"><a href="#cite_note-pmid32203405-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid33539964_33-0" class="reference"><a href="#cite_note-pmid33539964-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> However, in chemical nomenclature, the prefix "oxy" is associated with ether functional groups, i.e., a <a href="/wiki/Chemical_compound" title="Chemical compound">compound</a> with an oxygen atom connected to two <a href="/wiki/Alkyl_group" title="Alkyl group">alkyl</a> or <a href="/wiki/Aryl_group" title="Aryl group">aryl</a> groups (R-O-R),<sup id="cite_ref-norc-oxy_34-0" class="reference"><a href="#cite_note-norc-oxy-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> therefore, using "oxy" within the name of a steroid class may be misleading. One can find clear examples of "oxygenated" to refer to a broad class of organic molecules containing a variety of oxygen containing functional groups in other domains of organic chemistry,<sup id="cite_ref-Barrientos-2013_35-0" class="reference"><a href="#cite_note-Barrientos-2013-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> and it is appropriate to use this convention.<sup id="cite_ref-wj_14-6" class="reference"><a href="#cite_note-wj-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>Even though "keto" is a standard prefix in organic chemistry, the 1989 recommendations of the Joint Commission on Biochemical Nomenclature discourage the application of the prefix "keto" for steroid names, and favor the prefix "oxo" (e.g., 11-oxo steroids rather than 11-keto steroids), because "keto" includes the carbon that is part of the steroid nucleus and the same carbon atom should not be specified twice.<sup id="cite_ref-pmid2606099-keto_36-0" class="reference"><a href="#cite_note-pmid2606099-keto-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-wj_14-7" class="reference"><a href="#cite_note-wj-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Species_distribution">Species distribution</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Steroid&action=edit&section=4" title="Edit section: Species distribution"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1251242444">.mw-parser-output .ambox{border:1px solid #a2a9b1;border-left:10px solid #36c;background-color:#fbfbfb;box-sizing:border-box}.mw-parser-output .ambox+link+.ambox,.mw-parser-output .ambox+link+style+.ambox,.mw-parser-output .ambox+link+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+style+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+link+.ambox{margin-top:-1px}html body.mediawiki .mw-parser-output .ambox.mbox-small-left{margin:4px 1em 4px 0;overflow:hidden;width:238px;border-collapse:collapse;font-size:88%;line-height:1.25em}.mw-parser-output .ambox-speedy{border-left:10px solid #b32424;background-color:#fee7e6}.mw-parser-output .ambox-delete{border-left:10px solid #b32424}.mw-parser-output .ambox-content{border-left:10px solid #f28500}.mw-parser-output .ambox-style{border-left:10px solid #fc3}.mw-parser-output .ambox-move{border-left:10px solid #9932cc}.mw-parser-output .ambox-protection{border-left:10px solid #a2a9b1}.mw-parser-output .ambox .mbox-text{border:none;padding:0.25em 0.5em;width:100%}.mw-parser-output .ambox .mbox-image{border:none;padding:2px 0 2px 0.5em;text-align:center}.mw-parser-output .ambox .mbox-imageright{border:none;padding:2px 0.5em 2px 0;text-align:center}.mw-parser-output .ambox .mbox-empty-cell{border:none;padding:0;width:1px}.mw-parser-output .ambox .mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-Expert_needed plainlinks metadata ambox ambox-content" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/b/b4/Ambox_important.svg/40px-Ambox_important.svg.png" decoding="async" width="40" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/b/b4/Ambox_important.svg/60px-Ambox_important.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/b/b4/Ambox_important.svg/80px-Ambox_important.svg.png 2x" data-file-width="40" data-file-height="40" /></span></span></div></td><td class="mbox-text"><div class="mbox-text-span">This section <b>needs attention from an expert in pharmacology</b>. The specific problem is: <b>to examine this and the following section (and throughout), and to remove redundancies of listed content, and to ensure sourcing for the listed content that remains in any section.</b><span class="hide-when-compact"> <a href="/wiki/Wikipedia:WikiProject_Pharmacology" title="Wikipedia:WikiProject Pharmacology">WikiProject Pharmacology</a> may be able to help recruit an expert.</span> <span class="date-container"><i>(<span class="date">March 2017</span>)</i></span></div></td></tr></tbody></table> <p>Steroids are found in all domains of life including <a href="/wiki/Bacteria" title="Bacteria">bacteria</a>, <a href="/wiki/Archaea" title="Archaea">archaea</a>, and <a href="/wiki/Eukaryote" title="Eukaryote">eukaryotes</a>. In eukaryotes, steroids are found in fungi, plants, and animals.<sup id="cite_ref-Britannica-Biological-significance-of-steroids_37-0" class="reference"><a href="#cite_note-Britannica-Biological-significance-of-steroids-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-libre_38-0" class="reference"><a href="#cite_note-libre-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Eukaryotic_and_Prokaryotic">Eukaryotic and Prokaryotic</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Steroid&action=edit&section=5" title="Edit section: Eukaryotic and Prokaryotic"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1251242444"><table class="box-Missing_information plainlinks metadata ambox ambox-content" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><a href="/wiki/File:Wiki_letter_w.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/en/thumb/6/6c/Wiki_letter_w.svg/44px-Wiki_letter_w.svg.png" decoding="async" width="44" height="44" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/6/6c/Wiki_letter_w.svg/66px-Wiki_letter_w.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/6/6c/Wiki_letter_w.svg/88px-Wiki_letter_w.svg.png 2x" data-file-width="44" data-file-height="44" /></a></span></div></td><td class="mbox-text"><div class="mbox-text-span">This section <b>is missing information</b> about non-eukaryotic type sterol framework – see PMID 27446030, fig 4/5, group 1 <a href="/wiki/Oxidosqualene_cyclase" title="Oxidosqualene cyclase">oxidosqualene cyclase</a>.<span class="hide-when-compact"> Please expand the section to include this information. Further details may exist on the <a href="/wiki/Talk:Steroid" title="Talk:Steroid">talk page</a>.</span> <span class="date-container"><i>(<span class="date">November 2021</span>)</i></span></div></td></tr></tbody></table> <p><a href="/wiki/Eukaryote" title="Eukaryote">Eukaryotic</a> cells, which include animals, plants, fungi, and protists, have complex cellular structures with a true nucleus and membrane-bound organelles.<sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> </p><p>Steroids are integral to eukaryotic cellular membranes, where they help maintain membrane integrity and function.<sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </p><p>During <a href="/wiki/Eukaryogenesis" title="Eukaryogenesis">eukaryogenesis</a> (the emergence of modern eukaryotic cells), steroids likely played a role in the acquisition of mitochondria via endocytosis.<sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p><p>In <a href="/wiki/Prokaryotes" class="mw-redirect" title="Prokaryotes">prokaryotes</a>, biosynthetic pathways exist for the tetracyclic steroid framework (e.g. in <a href="/wiki/Myxobacteria" title="Myxobacteria">myxobacteria</a>)<sup id="cite_ref-pmid12519197_42-0" class="reference"><a href="#cite_note-pmid12519197-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> – where its origin from <a href="/wiki/Eukaryote" title="Eukaryote">eukaryotes</a> is conjectured<sup id="cite_ref-pmid20333205_43-0" class="reference"><a href="#cite_note-pmid20333205-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> – and the more-common pentacyclic <a href="/wiki/Triterpene" title="Triterpene">triterpinoid</a> <a href="/wiki/Hopane" title="Hopane">hopanoid</a> framework.<sup id="cite_ref-pmid21531832_44-0" class="reference"><a href="#cite_note-pmid21531832-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Fungal">Fungal</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Steroid&action=edit&section=6" title="Edit section: Fungal"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Fungal steroids include the <a href="/wiki/Ergosterol" title="Ergosterol">ergosterols</a>, which are involved in maintaining the integrity of the fungal cellular membrane. Various <a href="/wiki/Antifungal_drugs" class="mw-redirect" title="Antifungal drugs">antifungal drugs</a>, such as <a href="/wiki/Amphotericin_B" title="Amphotericin B">amphotericin B</a> and <a href="/wiki/Azole_antifungals" class="mw-redirect" title="Azole antifungals">azole antifungals</a>, utilize this information to kill <a href="/wiki/Pathogenic" class="mw-redirect" title="Pathogenic">pathogenic</a> fungi.<sup id="cite_ref-Bhetariya-2017_45-0" class="reference"><a href="#cite_note-Bhetariya-2017-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> Fungi can alter their ergosterol content (e.g. through loss of function mutations in the enzymes <a href="/wiki/C-5_sterol_desaturase" title="C-5 sterol desaturase">ERG3</a> or <a href="/wiki/Sterol_24-C-methyltransferase" title="Sterol 24-C-methyltransferase">ERG6</a>, inducing depletion of ergosterol, or mutations that decrease the ergosterol content) to develop resistance to drugs that target ergosterol.<sup id="cite_ref-Kavanagh_Fungi_46-0" class="reference"><a href="#cite_note-Kavanagh_Fungi-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> </p><p>Ergosterol is analogous to the <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a> found in the cellular membranes of animals (including humans), or the <a href="/wiki/Phytosterols" class="mw-redirect" title="Phytosterols">phytosterols</a> found in the cellular membranes of plants.<sup id="cite_ref-Kavanagh_Fungi_46-1" class="reference"><a href="#cite_note-Kavanagh_Fungi-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> All mushrooms contain large quantities of ergosterol, in the range of tens to hundreds of milligrams per 100 grams of dry weight.<sup id="cite_ref-Kavanagh_Fungi_46-2" class="reference"><a href="#cite_note-Kavanagh_Fungi-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> Oxygen is necessary for the synthesis of <a href="/wiki/Ergosterol" title="Ergosterol">ergosterol</a> in fungi.<sup id="cite_ref-Kavanagh_Fungi_46-3" class="reference"><a href="#cite_note-Kavanagh_Fungi-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> </p><p>Ergosterol is responsible for the <a href="/wiki/Vitamin_D" title="Vitamin D">vitamin D</a> content found in mushrooms; ergosterol is chemically converted into provitamin D2 by exposure to <a href="/wiki/Ultraviolet_light" class="mw-redirect" title="Ultraviolet light">ultraviolet light</a>.<sup id="cite_ref-Kavanagh_Fungi_46-4" class="reference"><a href="#cite_note-Kavanagh_Fungi-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> Provitamin D2 spontaneously forms vitamin D2.<sup id="cite_ref-Kavanagh_Fungi_46-5" class="reference"><a href="#cite_note-Kavanagh_Fungi-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> However, not all fungi utilize ergosterol in their cellular membranes; for example, the pathogenic fungal species <i><a href="/wiki/Pneumocystis_jirovecii" title="Pneumocystis jirovecii">Pneumocystis jirovecii</a></i> does not, which has important clinical implications (given the mechanism of action of many antifungal drugs). Using the fungus <i><a href="/wiki/Saccharomyces_cerevisiae" title="Saccharomyces cerevisiae">Saccharomyces cerevisiae</a></i> as an example, other major steroids include <a href="/w/index.php?title=Ergosta%E2%80%905,7,22,24(28)%E2%80%90tetraen%E2%80%903%CE%B2%E2%80%90ol&action=edit&redlink=1" class="new" title="Ergosta‐5,7,22,24(28)‐tetraen‐3β‐ol (page does not exist)">ergosta‐5,7,22,24(28)‐tetraen‐3β‐ol</a>, <a href="/wiki/Zymosterol" title="Zymosterol">zymosterol</a>, and <a href="/wiki/Lanosterol" title="Lanosterol">lanosterol</a>. <i>S. cerevisiae</i> utilizes <a href="/w/index.php?title=5,6%E2%80%90dihydroergosterol&action=edit&redlink=1" class="new" title="5,6‐dihydroergosterol (page does not exist)">5,6‐dihydroergosterol</a> in place of ergosterol in its cell membrane.<sup id="cite_ref-Kavanagh_Fungi_46-6" class="reference"><a href="#cite_note-Kavanagh_Fungi-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Plant">Plant</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Steroid&action=edit&section=7" title="Edit section: Plant"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Plant steroids include steroidal <a href="/wiki/Alkaloid" title="Alkaloid">alkaloids</a> found in <a href="/wiki/Solanaceae" title="Solanaceae">Solanaceae</a><sup id="cite_ref-pmid12946402_47-0" class="reference"><a href="#cite_note-pmid12946402-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Melanthiaceae" title="Melanthiaceae">Melanthiaceae</a> (specially the genus <a href="/wiki/Veratrum" title="Veratrum">Veratrum</a>),<sup id="cite_ref-Maappotw1_48-0" class="reference"><a href="#cite_note-Maappotw1-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Cardiac_glycoside" title="Cardiac glycoside">cardiac glycosides</a>,<sup id="cite_ref-Maappotw2_49-0" class="reference"><a href="#cite_note-Maappotw2-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> the <a href="/wiki/Phytosterol" title="Phytosterol">phytosterols</a> and the <a href="/wiki/Brassinosteroid" title="Brassinosteroid">brassinosteroids</a> (which include several plant hormones). </p> <div class="mw-heading mw-heading3"><h3 id="Animal">Animal</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Steroid&action=edit&section=8" title="Edit section: Animal"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Animal steroids include compounds of <a href="/wiki/Vertebrate" title="Vertebrate">vertebrate</a> and <a href="/wiki/Insect" title="Insect">insect</a> origin, the latter including <a href="/wiki/Ecdysteroid" title="Ecdysteroid">ecdysteroids</a> such as <a href="/wiki/Ecdysterone" class="mw-redirect" title="Ecdysterone">ecdysterone</a> (controlling molting in some species). Vertebrate examples include the <a href="/wiki/Steroid_hormones" class="mw-redirect" title="Steroid hormones">steroid hormones</a> and cholesterol; the latter is a structural component of <a href="/wiki/Cell_membranes" class="mw-redirect" title="Cell membranes">cell membranes</a> that helps determine the fluidity of <a href="/wiki/Cell_membranes" class="mw-redirect" title="Cell membranes">cell membranes</a> and is a principal constituent of <a href="/wiki/Atheroma" title="Atheroma">plaque</a> (implicated in <a href="/wiki/Atherosclerosis" title="Atherosclerosis">atherosclerosis</a>). Steroid hormones include: </p> <ul><li><a href="/wiki/Sex_hormone" title="Sex hormone">Sex hormones</a>, which influence <a href="/wiki/Sexual_differentiation" title="Sexual differentiation">sex differences</a> and support <a href="/wiki/Reproduction" title="Reproduction">reproduction</a>. These include <a href="/wiki/Androgen" title="Androgen">androgens</a>, <a href="/wiki/Estrogen" title="Estrogen">estrogens</a>, and <a href="/wiki/Progestogen" title="Progestogen">progestogens</a>.</li> <li><a href="/wiki/Corticosteroid" title="Corticosteroid">Corticosteroids</a>, including most synthetic steroid drugs, with <a href="/wiki/Natural_product" title="Natural product">natural product</a> classes the <a href="/wiki/Glucocorticoid" title="Glucocorticoid">glucocorticoids</a> (which regulate many aspects of <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> and <a href="/wiki/Immune_system" title="Immune system">immune function</a>) and the <a href="/wiki/Mineralocorticoid" title="Mineralocorticoid">mineralocorticoids</a> (which help maintain blood volume and control <a href="/wiki/Kidney" title="Kidney">renal</a> excretion of <a href="/wiki/Electrolyte" title="Electrolyte">electrolytes</a>)</li> <li><a href="/wiki/Anabolic_steroid" title="Anabolic steroid">Anabolic steroids</a>, <a href="/wiki/Natural_product" title="Natural product">natural</a> and synthetic, which interact with androgen receptors to increase muscle and bone synthesis. In popular use, the term "steroids" often refers to anabolic steroids.</li></ul> <div class="mw-heading mw-heading2"><h2 id="Types">Types</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Steroid&action=edit&section=9" title="Edit section: Types"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="By_function">By function</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Steroid&action=edit&section=10" title="Edit section: By function"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1251242444"><table class="box-Expand_section plainlinks metadata ambox ambox-content" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><a href="/wiki/File:Wiki_letter_w_cropped.svg" class="mw-file-description"><img alt="[icon]" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Wiki_letter_w_cropped.svg/20px-Wiki_letter_w_cropped.svg.png" decoding="async" width="20" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Wiki_letter_w_cropped.svg/30px-Wiki_letter_w_cropped.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Wiki_letter_w_cropped.svg/40px-Wiki_letter_w_cropped.svg.png 2x" data-file-width="44" data-file-height="31" /></a></span></div></td><td class="mbox-text"><div class="mbox-text-span">This section <b>needs expansion</b> with: A more detailed explanation of function would also be beneficial. You can help by <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Steroid&action=edit&section=">adding to it</a>. <span class="date-container"><i>(<span class="date">January 2019</span>)</i></span></div></td></tr></tbody></table> <p>The major classes of <a href="/wiki/Steroid_hormones" class="mw-redirect" title="Steroid hormones">steroid hormones</a>, with prominent members and examples of related functions, are:<sup id="cite_ref-pmid24940130_50-0" class="reference"><a href="#cite_note-pmid24940130-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> </p> <ul><li><a href="/wiki/Corticosteroid" title="Corticosteroid">Corticosteroids</a>: <ul><li><a href="/wiki/Glucocorticoid" title="Glucocorticoid">Glucocorticoids</a>: <ul><li><a href="/wiki/Cortisol" title="Cortisol">Cortisol</a>, a <a href="/wiki/Glucocorticoid" title="Glucocorticoid">glucocorticoid</a> whose functions include <a href="/wiki/Immunosuppression" title="Immunosuppression">immunosuppression</a></li></ul></li> <li><a href="/wiki/Mineralocorticoid" title="Mineralocorticoid">Mineralocorticoids</a>: <ul><li><a href="/wiki/Aldosterone" title="Aldosterone">Aldosterone</a>, a <a href="/wiki/Mineralocorticoid" title="Mineralocorticoid">mineralocorticoid</a> that helps regulate <a href="/wiki/Blood_pressure" title="Blood pressure">blood pressure</a> through water and electrolyte balance</li></ul></li></ul></li> <li><a href="/wiki/Sex_steroid" class="mw-redirect" title="Sex steroid">Sex steroids</a>: <ul><li><a href="/wiki/Progestogen" title="Progestogen">Progestogens</a>: <ul><li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a>, which regulates cyclical changes in the <a href="/wiki/Endometrium" title="Endometrium">endometrium</a> of the <a href="/wiki/Uterus" title="Uterus">uterus</a> and maintains a <a href="/wiki/Pregnancy" title="Pregnancy">pregnancy</a></li></ul></li> <li><a href="/wiki/Androgens" class="mw-redirect" title="Androgens">Androgens</a>: <ul><li><a href="/wiki/Testosterone" title="Testosterone">Testosterone</a>, which contributes to the development and maintenance of male <a href="/wiki/Secondary_sex_characteristic" title="Secondary sex characteristic">secondary sex characteristics</a></li></ul></li> <li><a href="/wiki/Estrogens" class="mw-redirect" title="Estrogens">Estrogens</a>: <ul><li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a>, which contributes to the development and maintenance of female secondary sex characteristics</li></ul></li></ul></li></ul> <p>Additional classes of steroids include: </p> <ul><li><a href="/wiki/Neurosteroid" title="Neurosteroid">Neurosteroids</a> such as <a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone"><abbr title="dehydroepiandrosterone">DHEA</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip dehydroepiandrosterone</span> and <a href="/wiki/Allopregnanolone" title="Allopregnanolone">allopregnanolone</a></li> <li><a href="/wiki/Bile_acid" title="Bile acid">Bile acids</a> such as <a href="/wiki/Taurocholic_acid" title="Taurocholic acid">taurocholic acid</a></li> <li><a href="/wiki/Aminosteroid" title="Aminosteroid">Aminosteroid</a> <a href="/wiki/Neuromuscular_blocking_agent" class="mw-redirect" title="Neuromuscular blocking agent">neuromuscular blocking agents</a> (mainly synthetic) such as <a href="/wiki/Pancuronium_bromide" title="Pancuronium bromide">pancuronium bromide</a></li> <li><a href="/wiki/Steroidal_antiandrogen" title="Steroidal antiandrogen">Steroidal antiandrogens</a> (mainly synthetic) such as <a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">cyproterone acetate</a></li> <li><a href="/wiki/Steroidogenesis_inhibitor" title="Steroidogenesis inhibitor">Steroidogenesis inhibitors</a> (mainly exogenous) such as <a href="/wiki/Alfatradiol" title="Alfatradiol">alfatradiol</a></li> <li>Membrane sterols such as <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a>, <a href="/wiki/Ergosterol" title="Ergosterol">ergosterol</a>, and various <a href="/wiki/Phytosterol" title="Phytosterol">phytosterols</a></li> <li>Toxins such as steroidal <a href="/wiki/Saponin" title="Saponin">saponins</a> and <a href="/wiki/Cardenolide" title="Cardenolide">cardenolides</a>/<a href="/wiki/Cardiac_glycoside" title="Cardiac glycoside">cardiac glycosides</a></li></ul> <p>As well as the following class of <a href="/wiki/Secosteroid" title="Secosteroid">secosteroids</a> (open-ring steroids): </p> <ul><li><a href="/wiki/Vitamin_D" title="Vitamin D">Vitamin D</a> forms such as <a href="/wiki/Ergocalciferol" title="Ergocalciferol">ergocalciferol</a>, <a href="/wiki/Cholecalciferol" title="Cholecalciferol">cholecalciferol</a>, and <a href="/wiki/Calcitriol" title="Calcitriol">calcitriol</a></li></ul> <div class="mw-heading mw-heading3"><h3 id="By_structure">By structure</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Steroid&action=edit&section=11" title="Edit section: By structure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="Intact_ring_system">Intact ring system</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Steroid&action=edit&section=12" title="Edit section: Intact ring system"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1251242444"><table class="box-Expand_section plainlinks metadata ambox ambox-content" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><a href="/wiki/File:Wiki_letter_w_cropped.svg" class="mw-file-description"><img alt="[icon]" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Wiki_letter_w_cropped.svg/44px-Wiki_letter_w_cropped.svg.png" decoding="async" width="44" height="31" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Wiki_letter_w_cropped.svg/66px-Wiki_letter_w_cropped.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Wiki_letter_w_cropped.svg/88px-Wiki_letter_w_cropped.svg.png 2x" data-file-width="44" data-file-height="31" /></a></span></div></td><td class="mbox-text"><div class="mbox-text-span">This section <b>needs expansion</b> with: a more full discussion of this most prominent structural type. You can help by <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Steroid&action=edit&section=">adding to it</a>. <span class="date-container"><i>(<span class="date">March 2017</span>)</i></span></div></td></tr></tbody></table> <p>Steroids can be classified based on their chemical composition.<sup id="cite_ref-Zorea-2014_52-0" class="reference"><a href="#cite_note-Zorea-2014-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> One example of how <a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a> performs this classification is available at the Wikipedia MeSH catalog. Examples of this classification include: </p> <figure class="mw-default-size skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Cholecalciferol.svg" class="mw-file-description"><img alt="Chemical diagram" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/79/Cholecalciferol.svg/220px-Cholecalciferol.svg.png" decoding="async" width="220" height="235" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/79/Cholecalciferol.svg/330px-Cholecalciferol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/79/Cholecalciferol.svg/440px-Cholecalciferol.svg.png 2x" data-file-width="512" data-file-height="546" /></a><figcaption><a href="/wiki/Cholecalciferol" title="Cholecalciferol">Cholecalciferol</a> (vitamin D<sub><small>3</small></sub>), an example of a 9,10-<a href="/wiki/Secosteroid" title="Secosteroid">secosteroid</a></figcaption></figure> <figure class="mw-default-size skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Cyclopamine.svg" class="mw-file-description"><img alt="Chemical diagram" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5b/Cyclopamine.svg/220px-Cyclopamine.svg.png" decoding="async" width="220" height="154" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5b/Cyclopamine.svg/330px-Cyclopamine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5b/Cyclopamine.svg/440px-Cyclopamine.svg.png 2x" data-file-width="1505" data-file-height="1054" /></a><figcaption><a href="/wiki/Cyclopamine" title="Cyclopamine">Cyclopamine</a>, an example of a complex C-nor-D-homosteroid</figcaption></figure> <table class="wikitable"> <tbody><tr> <th align="center">Class </th> <th align="center">Example </th> <th align="center">Number of carbon atoms </th></tr> <tr> <td align="center"><a href="/wiki/Cholestane" title="Cholestane">Cholestanes</a> </td> <td align="center">Cholesterol </td> <td align="center">27 </td></tr> <tr> <td align="center"><a href="/wiki/Cholane" title="Cholane">Cholanes</a> </td> <td align="center">Cholic acid </td> <td align="center">24 </td></tr> <tr> <td align="center"><a href="/wiki/Pregnane" title="Pregnane">Pregnanes</a> </td> <td align="center">Progesterone </td> <td align="center">21 </td></tr> <tr> <td align="center"><a href="/wiki/Androstane" title="Androstane">Androstanes</a> </td> <td align="center">Testosterone </td> <td align="center">19 </td></tr> <tr> <td align="center"><a href="/wiki/Estrane" title="Estrane">Estranes</a> </td> <td align="center">Estradiol </td> <td align="center">18 </td></tr> </tbody></table> <p>In biology, it is common to name the above steroid classes by the number of carbon atoms present when referring to hormones: C<sub>18</sub>-steroids for the estranes (mostly estrogens), C<sub>19</sub>-steroids for the androstanes (mostly androgens), and C<sub>21</sub>-steroids for the pregnanes (mostly corticosteroids).<sup id="cite_ref-rgd.mcw.edu-C19_53-0" class="reference"><a href="#cite_note-rgd.mcw.edu-C19-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> The classification "<a href="/wiki/17-ketosteroid" class="mw-redirect" title="17-ketosteroid">17-ketosteroid</a>" is also important in medicine. </p><p>The gonane (steroid nucleus) is the parent 17-carbon tetracyclic hydrocarbon molecule with no <a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">alkyl</a> sidechains.<sup id="cite_ref-pmid10715364_54-0" class="reference"><a href="#cite_note-pmid10715364-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Cleaved,_contracted,_and_expanded_rings"><span id="Cleaved.2C_contracted.2C_and_expanded_rings"></span>Cleaved, contracted, and expanded rings</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Steroid&action=edit&section=13" title="Edit section: Cleaved, contracted, and expanded rings"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Secosteroids (Latin <i>seco</i>, "to cut") are a subclass of steroidal compounds resulting, <a href="/wiki/Biosynthesis" title="Biosynthesis">biosynthetically</a> or conceptually, from scission (cleavage) of parent steroid rings (generally one of the four). Major secosteroid subclasses are defined by the steroid carbon atoms where this scission has taken place. For instance, the prototypical secosteroid <a href="/wiki/Cholecalciferol" title="Cholecalciferol">cholecalciferol</a>, <a href="/wiki/Vitamin_D3" class="mw-redirect" title="Vitamin D3">vitamin D<sub>3</sub></a> (shown), is in the 9,10-secosteroid subclass and derives from the cleavage of carbon atoms C-9 and C-10 of the steroid B-ring; 5,6-secosteroids and 13,14-steroids are similar.<sup id="cite_ref-pmid20424788_55-0" class="reference"><a href="#cite_note-pmid20424788-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Norsteroid" title="Norsteroid">Norsteroids</a> (<a href="/wiki/Nor-" title="Nor-">nor-</a>, L. <i>norma</i>; "normal" in chemistry, indicating carbon removal)<sup id="cite_ref-iupacRF41_56-0" class="reference"><a href="#cite_note-iupacRF41-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> and homosteroids (homo-, Greek <i>homos</i>; "same", indicating carbon addition) are structural subclasses of steroids formed from biosynthetic steps. The former involves enzymic <a href="/wiki/Ring_expansion" class="mw-redirect" title="Ring expansion">ring expansion-contraction</a> reactions, and the latter is accomplished (<a href="/wiki/Biomimetic_synthesis" title="Biomimetic synthesis">biomimetically</a>) or (more frequently) through <a href="/wiki/Ring_closure" class="mw-redirect" title="Ring closure">ring closures</a> of <a href="/wiki/Open-chain_compound" title="Open-chain compound">acyclic</a> precursors with more (or fewer) ring atoms than the parent steroid framework.<sup id="cite_ref-Wolfing07_57-0" class="reference"><a href="#cite_note-Wolfing07-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> </p><p>Combinations of these ring alterations are known in nature. For instance, <a href="/wiki/Sheep" title="Sheep">ewes</a> who graze on <a href="/wiki/Veratrum" title="Veratrum">corn lily</a> ingest <a href="/wiki/Cyclopamine" title="Cyclopamine">cyclopamine</a> (shown) and <a href="/wiki/Veratramine" title="Veratramine">veratramine</a>, two of a sub-family of steroids where the C- and D-rings are contracted and expanded respectively via a <a href="/wiki/Biosynthesis" title="Biosynthesis">biosynthetic</a> migration of the original C-13 atom. Ingestion of these C-nor-D-homosteroids results in birth defects in lambs: <a href="/wiki/Cyclopia" title="Cyclopia">cyclopia</a> from <a href="/wiki/Cyclopamine" title="Cyclopamine">cyclopamine</a> and leg deformity from veratramine.<sup id="cite_ref-GaoChen2012_58-0" class="reference"><a href="#cite_note-GaoChen2012-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> A further C-nor-D-homosteroid (nakiterpiosin) is excreted by <a href="/wiki/Okinawa_Prefecture" title="Okinawa Prefecture">Okinawan</a> <a href="/wiki/Cyanobacteria" title="Cyanobacteria">cyanobacteriosponges</a>. e.g., <i><a href="/wiki/Terpios" title="Terpios">Terpios</a> hoshinota</i>, leading to coral mortality from black coral disease.<sup id="cite_ref-Uemura-2009_59-0" class="reference"><a href="#cite_note-Uemura-2009-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> Nakiterpiosin-type steroids are active against the signaling pathway involving the <a href="/wiki/Smoothened" title="Smoothened">smoothened</a> and <a href="/wiki/Hedgehog_(cell_signaling)" class="mw-redirect" title="Hedgehog (cell signaling)">hedgehog</a> proteins, a pathway which is hyperactive in a number of cancers.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (March 2019)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="Biological_significance">Biological significance</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Steroid&action=edit&section=14" title="Edit section: Biological significance"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Steroids and their metabolites often function as <a href="/wiki/Signal_transduction" title="Signal transduction">signalling</a> molecules (the most notable examples are steroid hormones), and steroids and <a href="/wiki/Phospholipid" title="Phospholipid">phospholipids</a> are components of <a href="/wiki/Cell_membrane" title="Cell membrane">cell membranes</a>.<sup id="cite_ref-Silverthorn-2016_60-0" class="reference"><a href="#cite_note-Silverthorn-2016-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup> Steroids such as cholesterol decrease <a href="/wiki/Membrane_fluidity" title="Membrane fluidity">membrane fluidity</a>.<sup id="cite_ref-isbn1-4292-4646-4_61-0" class="reference"><a href="#cite_note-isbn1-4292-4646-4-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> Similar to <a href="/wiki/Lipid" title="Lipid">lipids</a>, steroids are highly concentrated energy stores. However, they are not typically sources of energy; in mammals, they are normally metabolized and excreted. </p><p>Steroids play critical roles in a number of disorders, including malignancies like <a href="/wiki/Prostate_cancer" title="Prostate cancer">prostate cancer</a>, where steroid production inside and outside the tumour promotes cancer cell aggressiveness.<sup id="cite_ref-pmid27672740_62-0" class="reference"><a href="#cite_note-pmid27672740-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Biosynthesis_and_metabolism">Biosynthesis and metabolism</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Steroid&action=edit&section=15" title="Edit section: Biosynthesis and metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Sterol_synthesis.svg" class="mw-file-description"><img alt="Chemical-diagram flow chart" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/18/Sterol_synthesis.svg/300px-Sterol_synthesis.svg.png" decoding="async" width="300" height="336" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/18/Sterol_synthesis.svg/450px-Sterol_synthesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/18/Sterol_synthesis.svg/600px-Sterol_synthesis.svg.png 2x" data-file-width="571" data-file-height="640" /></a><figcaption>Simplification of the end of the steroid synthesis pathway, where the intermediates <a href="/wiki/Isopentenyl_pyrophosphate" title="Isopentenyl pyrophosphate">isopentenyl pyrophosphate</a> (PP or IPP) and <a href="/wiki/Dimethylallyl_pyrophosphate" title="Dimethylallyl pyrophosphate">dimethylallyl pyrophosphate</a> (DMAPP) form <a href="/wiki/Geranyl_pyrophosphate" title="Geranyl pyrophosphate">geranyl pyrophosphate</a> (GPP), <a href="/wiki/Squalene" title="Squalene">squalene</a> and <a href="/wiki/Lanosterol" title="Lanosterol">lanosterol</a> (the first steroid in the pathway)</figcaption></figure> <p>The hundreds of steroids found in animals, fungi, and <a href="/wiki/Plant" title="Plant">plants</a> are made from <a href="/wiki/Lanosterol" title="Lanosterol">lanosterol</a> (in animals and fungi; see examples above) or <a href="/wiki/Cycloartenol" title="Cycloartenol">cycloartenol</a> (in other eukaryotes). Both lanosterol and cycloartenol derive from <a href="/wiki/Cyclic_compound" title="Cyclic compound">cyclization</a> of the <a href="/wiki/Triterpene" title="Triterpene">triterpenoid</a> <a href="/wiki/Squalene" title="Squalene">squalene</a>.<sup id="cite_ref-urlLanosterol_biosynthesis_4-1" class="reference"><a href="#cite_note-urlLanosterol_biosynthesis-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Lanosterol and cycloartenol are sometimes called protosterols because they serve as the starting compounds for all other steroids. </p><p>Steroid biosynthesis is an <a href="/wiki/Anabolism" title="Anabolism">anabolic</a> pathway which produces steroids from simple precursors. A unique biosynthetic pathway is followed in animals (compared to many other <a href="/wiki/Organism" title="Organism">organisms</a>), making the pathway a common target for <a href="/wiki/Antibiotic" title="Antibiotic">antibiotics</a> and other anti-infection drugs. Steroid metabolism in humans is also the target of cholesterol-lowering drugs, such as <a href="/wiki/Statin" title="Statin">statins</a>. In humans and other animals the biosynthesis of steroids follows the mevalonate pathway, which uses <a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">acetyl-CoA</a> as building blocks for <a href="/wiki/Dimethylallyl_pyrophosphate" title="Dimethylallyl pyrophosphate">dimethylallyl diphosphate</a> (DMAPP) and <a href="/wiki/Isopentenyl_pyrophosphate" title="Isopentenyl pyrophosphate">isopentenyl diphosphate</a> (IPP).<sup id="cite_ref-pmid16621811_63-0" class="reference"><a href="#cite_note-pmid16621811-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup><sup class="noprint Inline-Template noprint noexcerpt Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:NOTRS" class="mw-redirect" title="Wikipedia:NOTRS"><span title="This claim needs references to better sources. (July 2014)">better source needed</span></a></i>]</sup> </p><p>In subsequent steps DMAPP and IPP conjugate to form <a href="/wiki/Farnesyl_pyrophosphate" title="Farnesyl pyrophosphate">farnesyl diphosphate</a> (FPP), which further conjugates with each other to form the linear triterpenoid squalene. Squalene biosynthesis is catalyzed by <a href="/wiki/Farnesyl-diphosphate_farnesyltransferase" title="Farnesyl-diphosphate farnesyltransferase">squalene synthase</a>, which belongs to the <a href="/wiki/Squalene/phytoene_synthase_family" title="Squalene/phytoene synthase family">squalene/phytoene synthase family</a>. Subsequent <a href="/wiki/Epoxide" title="Epoxide">epoxidation</a> and cyclization of squalene generate lanosterol, which is the starting point for additional modifications into other steroids (steroidogenesis).<sup id="cite_ref-pmid30258364_64-0" class="reference"><a href="#cite_note-pmid30258364-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> In other eukaryotes, the cyclization product of epoxidized squalene (oxidosqualene) is cycloartenol. </p> <div class="mw-heading mw-heading3"><h3 id="Mevalonate_pathway">Mevalonate pathway</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Steroid&action=edit&section=16" title="Edit section: Mevalonate pathway"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Mevalonate_pathway.svg" class="mw-file-description"><img alt="Chemical flow chart" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b4/Mevalonate_pathway.svg/300px-Mevalonate_pathway.svg.png" decoding="async" width="300" height="424" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b4/Mevalonate_pathway.svg/450px-Mevalonate_pathway.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b4/Mevalonate_pathway.svg/600px-Mevalonate_pathway.svg.png 2x" data-file-width="744" data-file-height="1052" /></a><figcaption>Mevalonate pathway</figcaption></figure> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Mevalonate_pathway" title="Mevalonate pathway">Mevalonate pathway</a></div> <p>The mevalonate pathway (also called HMG-CoA reductase pathway) begins with <a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">acetyl-CoA</a> and ends with <a href="/wiki/Dimethylallyl_pyrophosphate" title="Dimethylallyl pyrophosphate">dimethylallyl diphosphate</a> (DMAPP) and <a href="/wiki/Isopentenyl_pyrophosphate" title="Isopentenyl pyrophosphate">isopentenyl diphosphate</a> (IPP). </p><p>DMAPP and IPP donate <a href="/wiki/Isoprene" title="Isoprene">isoprene</a> units, which are assembled and modified to form <a href="/wiki/Terpene" title="Terpene">terpenes</a> and <a href="/wiki/Terpenoid" title="Terpenoid">isoprenoids</a><sup id="cite_ref-pmid12735695_65-0" class="reference"><a href="#cite_note-pmid12735695-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> (a large class of lipids, which include the <a href="/wiki/Carotenoid" title="Carotenoid">carotenoids</a> and form the largest class of plant <a href="/wiki/Natural_product" title="Natural product">natural products</a>).<sup id="cite_ref-pmid14517367_66-0" class="reference"><a href="#cite_note-pmid14517367-66"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup> Here, the activated isoprene units are joined to make <a href="/wiki/Squalene" title="Squalene">squalene</a> and folded into a set of rings to make <a href="/wiki/Lanosterol" title="Lanosterol">lanosterol</a>.<sup id="cite_ref-pmid7023367_67-0" class="reference"><a href="#cite_note-pmid7023367-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup> Lanosterol can then be converted into other steroids, such as cholesterol and <a href="/wiki/Ergosterol" title="Ergosterol">ergosterol</a>.<sup id="cite_ref-pmid7023367_67-1" class="reference"><a href="#cite_note-pmid7023367-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid7791529_68-0" class="reference"><a href="#cite_note-pmid7791529-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> </p><p><span class="anchor" id="Pharmacological_actions"></span> Two classes of <a href="/wiki/Medication" title="Medication">drugs</a> target the <a href="/wiki/Mevalonate_pathway" title="Mevalonate pathway">mevalonate pathway</a>: <a href="/wiki/Statin" title="Statin">statins</a> (like <a href="/wiki/Rosuvastatin" title="Rosuvastatin">rosuvastatin</a>), which are used to reduce <a href="/wiki/Hypercholesterolemia" title="Hypercholesterolemia">elevated cholesterol levels</a>,<sup id="cite_ref-pmid21267417_69-0" class="reference"><a href="#cite_note-pmid21267417-69"><span class="cite-bracket">[</span>69<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Bisphosphonate" title="Bisphosphonate">bisphosphonates</a> (like <a href="/wiki/Zoledronate" class="mw-redirect" title="Zoledronate">zoledronate</a>), which are used to treat a number of bone-degenerative diseases.<sup id="cite_ref-pmid17062705_70-0" class="reference"><a href="#cite_note-pmid17062705-70"><span class="cite-bracket">[</span>70<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Steroidogenesis"><span class="anchor" id="Regulation">Steroidogenesis</span></h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Steroid&action=edit&section=17" title="Edit section: Steroidogenesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Steroidogenesis.svg" class="mw-file-description"><img alt="Chemical-diagram flow chart" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/13/Steroidogenesis.svg/300px-Steroidogenesis.svg.png" decoding="async" width="300" height="266" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/13/Steroidogenesis.svg/450px-Steroidogenesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/13/Steroidogenesis.svg/600px-Steroidogenesis.svg.png 2x" data-file-width="1245" data-file-height="1105" /></a><figcaption>Human steroidogenesis, with the major classes of steroid hormones, individual steroids and <a href="/wiki/Enzyme" title="Enzyme">enzymatic</a> pathways.<sup id="cite_ref-HäggströmRichfield2014_71-0" class="reference"><a href="#cite_note-HäggströmRichfield2014-71"><span class="cite-bracket">[</span>71<span class="cite-bracket">]</span></a></sup> Changes in molecular structure from a precursor are highlighted in white.</figcaption></figure> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Steroidogenic_enzyme" title="Steroidogenic enzyme">Steroidogenic enzyme</a></div> <p>Steroidogenesis is the biological process by which steroids are generated from cholesterol and changed into other steroids.<sup id="cite_ref-pmid22217824_72-0" class="reference"><a href="#cite_note-pmid22217824-72"><span class="cite-bracket">[</span>72<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Metabolic_pathway" title="Metabolic pathway">pathways</a> of steroidogenesis differ among species. The major classes of steroid hormones, as noted above (with their prominent members and functions), are the <a href="/wiki/Progestogen" title="Progestogen">progestogens</a>, <a href="/wiki/Corticosteroid" title="Corticosteroid">corticosteroids</a> (corticoids), <a href="/wiki/Androgen" title="Androgen">androgens</a>, and <a href="/wiki/Estrogen" title="Estrogen">estrogens</a>.<sup id="cite_ref-pmid21051590_25-1" class="reference"><a href="#cite_note-pmid21051590-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid38035948_73-0" class="reference"><a href="#cite_note-pmid38035948-73"><span class="cite-bracket">[</span>73<span class="cite-bracket">]</span></a></sup> Human steroidogenesis of these classes occurs in a number of locations: </p> <ul><li>Progestogens are the precursors of all other human steroids, and all human tissues which produce steroids must first convert cholesterol to <a href="/wiki/Pregnenolone" title="Pregnenolone">pregnenolone</a>. This conversion is the rate-limiting step of steroid synthesis, which occurs inside the <a href="/wiki/Mitochondrion" title="Mitochondrion">mitochondrion</a> of the respective tissue. It is catalyzed by the mitochondrial P450scc system.<sup id="cite_ref-1980-Hanukoglu_74-0" class="reference"><a href="#cite_note-1980-Hanukoglu-74"><span class="cite-bracket">[</span>74<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-1981-Hanukoglu_75-0" class="reference"><a href="#cite_note-1981-Hanukoglu-75"><span class="cite-bracket">[</span>75<span class="cite-bracket">]</span></a></sup></li> <li>Cortisol, <a href="/wiki/Corticosterone" title="Corticosterone">corticosterone</a>, aldosterone are produced in the <a href="/wiki/Adrenal_cortex" title="Adrenal cortex">adrenal cortex</a>.<sup id="cite_ref-pmid21051590_25-2" class="reference"><a href="#cite_note-pmid21051590-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid38035948_73-1" class="reference"><a href="#cite_note-pmid38035948-73"><span class="cite-bracket">[</span>73<span class="cite-bracket">]</span></a></sup></li> <li>Estradiol, <a href="/wiki/Estrone" title="Estrone">estrone</a> and progesterone are made primarily in the <a href="/wiki/Ovary" title="Ovary">ovary</a>, estriol in <a href="/wiki/Placenta" title="Placenta">placenta</a> during pregnancy, and <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> primarily in the <a href="/wiki/Testes" class="mw-redirect" title="Testes">testes</a><sup id="cite_ref-pmid21051590_25-3" class="reference"><a href="#cite_note-pmid21051590-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-endocrine-poster_76-0" class="reference"><a href="#cite_note-endocrine-poster-76"><span class="cite-bracket">[</span>76<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-hpa_77-0" class="reference"><a href="#cite_note-hpa-77"><span class="cite-bracket">[</span>77<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-78" class="reference"><a href="#cite_note-78"><span class="cite-bracket">[</span>78<span class="cite-bracket">]</span></a></sup> (some testosterone may also be produced in the adrenal cortex).<sup id="cite_ref-pmid21051590_25-4" class="reference"><a href="#cite_note-pmid21051590-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid38035948_73-2" class="reference"><a href="#cite_note-pmid38035948-73"><span class="cite-bracket">[</span>73<span class="cite-bracket">]</span></a></sup></li> <li>Estradiol is converted from testosterone directly (in males), or via the primary pathway DHEA – androstenedione – estrone and secondarily via testosterone (in females).<sup id="cite_ref-pmid21051590_25-5" class="reference"><a href="#cite_note-pmid21051590-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Stromal_cells" class="mw-redirect" title="Stromal cells">Stromal cells</a> have been shown to produce steroids in response to signaling produced by androgen-starved <a href="/wiki/Prostate_cancer" title="Prostate cancer">prostate cancer</a> cells.<sup id="cite_ref-pmid27672740_62-1" class="reference"><a href="#cite_note-pmid27672740-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup><sup class="noprint Inline-Template noprint Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:No_original_research#Primary,_secondary_and_tertiary_sources" title="Wikipedia:No original research"><span title="This claim needs references to reliable secondary sources. (March 2017)">non-primary source needed</span></a></i>]</sup><sup class="noprint Inline-Template noprint noexcerpt Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:NOTRS" class="mw-redirect" title="Wikipedia:NOTRS"><span title="This claim needs references to better sources. (March 2017)">better source needed</span></a></i>]</sup></li> <li>Some <a href="/wiki/Neurons" class="mw-redirect" title="Neurons">neurons</a> and <a href="/wiki/Glia" title="Glia">glia</a> in the <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a> (CNS) express the <a href="/wiki/Enzymes" class="mw-redirect" title="Enzymes">enzymes</a> required for the local synthesis of pregnenolone, progesterone, DHEA and DHEAS, <a href="/wiki/De_novo_synthesis" title="De novo synthesis"><i>de novo</i></a> or from peripheral sources.<sup id="cite_ref-pmid21051590_25-6" class="reference"><a href="#cite_note-pmid21051590-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (March 2017)">citation needed</span></a></i>]</sup></li></ul> <table class="wikitable mw-collapsible mw-collapsed" style="margin: 1em auto;"> <caption class="nowrap"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist 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 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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:Production_rates,_secretion_rates,_clearance_rates,_and_blood_levels_of_major_sex_hormones" title="Template:Production rates, secretion rates, clearance rates, and blood levels of major sex hormones"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Production_rates,_secretion_rates,_clearance_rates,_and_blood_levels_of_major_sex_hormones" title="Template talk:Production rates, secretion rates, clearance rates, and blood levels of major sex hormones"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Production_rates,_secretion_rates,_clearance_rates,_and_blood_levels_of_major_sex_hormones" title="Special:EditPage/Template:Production rates, secretion rates, clearance rates, and blood levels of major sex hormones"><abbr title="Edit this template">e</abbr></a></li></ul></div> Production rates, secretion rates, clearance rates, and blood levels of major sex hormones </caption> <tbody><tr> <th rowspan="2">Sex </th> <th rowspan="2">Sex hormone </th> <th rowspan="2">Reproductive<br />phase </th> <th rowspan="2">Blood<br />production rate </th> <th rowspan="2">Gonadal<br />secretion rate </th> <th rowspan="2">Metabolic<br />clearance rate </th> <th colspan="2">Reference range (serum levels) </th></tr> <tr> <th><abbr title="Système International">SI</abbr> units </th> <th>Non-<abbr title="Système International">SI</abbr> units </th></tr> <tr> <td rowspan="5">Men </td> <td><a href="/wiki/Androstenedione" title="Androstenedione">Androstenedione</a> </td> <td><div class="center" style="width:auto; margin-left:auto; margin-right:auto;">–</div> </td> <td>2.8 mg/day </td> <td>1.6 mg/day </td> <td>2200 L/day </td> <td>2.8–7.3 nmol/L </td> <td>80–210 ng/dL </td></tr> <tr> <td><a href="/wiki/Testosterone" title="Testosterone">Testosterone</a> </td> <td><div class="center" style="width:auto; margin-left:auto; margin-right:auto;">–</div> </td> <td>6.5 mg/day </td> <td>6.2 mg/day </td> <td>950 L/day </td> <td>6.9–34.7 nmol/L </td> <td>200–1000 ng/dL </td></tr> <tr> <td><a href="/wiki/Estrone" title="Estrone">Estrone</a> </td> <td><div class="center" style="width:auto; margin-left:auto; margin-right:auto;">–</div> </td> <td>150 μg/day </td> <td>110 μg/day </td> <td>2050 L/day </td> <td>37–250 pmol/L </td> <td>10–70 pg/mL </td></tr> <tr> <td><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a> </td> <td><div class="center" style="width:auto; margin-left:auto; margin-right:auto;">–</div> </td> <td>60 μg/day </td> <td>50 μg/day </td> <td>1600 L/day </td> <td><37–210 pmol/L </td> <td>10–57 pg/mL </td></tr> <tr> <td><a href="/wiki/Estrone_sulfate" title="Estrone sulfate">Estrone sulfate</a> </td> <td><div class="center" style="width:auto; margin-left:auto; margin-right:auto;">–</div> </td> <td>80 μg/day </td> <td>Insignificant </td> <td>167 L/day </td> <td>600–2500 pmol/L </td> <td>200–900 pg/mL </td></tr> <tr> <td rowspan="12">Women </td> <td><a href="/wiki/Androstenedione" title="Androstenedione">Androstenedione</a> </td> <td><div class="center" style="width:auto; margin-left:auto; margin-right:auto;">–</div> </td> <td>3.2 mg/day </td> <td>2.8 mg/day </td> <td>2000 L/day </td> <td>3.1–12.2 nmol/L </td> <td>89–350 ng/dL </td></tr> <tr> <td><a href="/wiki/Testosterone" title="Testosterone">Testosterone</a> </td> <td><div class="center" style="width:auto; margin-left:auto; margin-right:auto;">–</div> </td> <td>190 μg/day </td> <td>60 μg/day </td> <td>500 L/day </td> <td>0.7–2.8 nmol/L </td> <td>20–81 ng/dL </td></tr> <tr> <td rowspan="3"><a href="/wiki/Estrone" title="Estrone">Estrone</a> </td> <td>Follicular phase </td> <td>110 μg/day </td> <td>80 μg/day </td> <td>2200 L/day </td> <td>110–400 pmol/L </td> <td>30–110 pg/mL </td></tr> <tr> <td>Luteal phase </td> <td>260 μg/day </td> <td>150 μg/day </td> <td>2200 L/day </td> <td>310–660 pmol/L </td> <td>80–180 pg/mL </td></tr> <tr> <td>Postmenopause </td> <td>40 μg/day </td> <td>Insignificant </td> <td>1610 L/day </td> <td>22–230 pmol/L </td> <td>6–60 pg/mL </td></tr> <tr> <td rowspan="3"><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a> </td> <td>Follicular phase </td> <td>90 μg/day </td> <td>80 μg/day </td> <td>1200 L/day </td> <td><37–360 pmol/L </td> <td>10–98 pg/mL </td></tr> <tr> <td>Luteal phase </td> <td>250 μg/day </td> <td>240 μg/day </td> <td>1200 L/day </td> <td>699–1250 pmol/L </td> <td>190–341 pg/mL </td></tr> <tr> <td>Postmenopause </td> <td>6 μg/day </td> <td>Insignificant </td> <td>910 L/day </td> <td><37–140 pmol/L </td> <td>10–38 pg/mL </td></tr> <tr> <td rowspan="2"><a href="/wiki/Estrone_sulfate" title="Estrone sulfate">Estrone sulfate</a> </td> <td>Follicular phase </td> <td>100 μg/day </td> <td>Insignificant </td> <td>146 L/day </td> <td>700–3600 pmol/L </td> <td>250–1300 pg/mL </td></tr> <tr> <td>Luteal phase </td> <td>180 μg/day </td> <td>Insignificant </td> <td>146 L/day </td> <td>1100–7300 pmol/L </td> <td>400–2600 pg/mL </td></tr> <tr> <td rowspan="2"><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a> </td> <td>Follicular phase </td> <td>2 mg/day </td> <td>1.7 mg/day </td> <td>2100 L/day </td> <td>0.3–3 nmol/L </td> <td>0.1–0.9 ng/mL </td></tr> <tr> <td>Luteal phase </td> <td>25 mg/day </td> <td>24 mg/day </td> <td>2100 L/day </td> <td>19–45 nmol/L </td> <td>6–14 ng/mL </td></tr> <tr> <td colspan="8" style="width: 1px; background-color:#eaecf0; text-align: center;"><style data-mw-deduplicate="TemplateStyles:r1214851843">.mw-parser-output .hidden-begin{box-sizing:border-box;width:100%;padding:5px;border:none;font-size:95%}.mw-parser-output .hidden-title{font-weight:bold;line-height:1.6;text-align:left}.mw-parser-output .hidden-content{text-align:left}@media all and (max-width:500px){.mw-parser-output .hidden-begin{width:auto!important;clear:none!important;float:none!important}}</style><div class="hidden-begin mw-collapsible mw-collapsed" style=""><div class="hidden-title skin-nightmode-reset-color" style="text-align:center;">Notes and sources</div><div class="hidden-content mw-collapsible-content" style=""> <span style="font-size:small;"><b>Notes:</b> "The <i>concentration</i> of a steroid in the circulation is determined by the rate at which it is secreted from glands, the rate of metabolism of precursor or prehormones into the steroid, and the rate at which it is extracted by tissues and metabolized. The <i>secretion rate</i> of a steroid refers to the total secretion of the compound from a gland per unit time. Secretion rates have been assessed by sampling the venous effluent from a gland over time and subtracting out the arterial and peripheral venous hormone concentration. The <i>metabolic clearance rate</i> of a steroid is defined as the volume of blood that has been completely cleared of the hormone per unit time. The <i>production rate</i> of a steroid hormone refers to entry into the blood of the compound from all possible sources, including secretion from glands and conversion of prohormones into the steroid of interest. At steady state, the amount of hormone entering the blood from all sources will be equal to the rate at which it is being cleared (metabolic clearance rate) multiplied by blood concentration (production rate = metabolic clearance rate × concentration). If there is little contribution of prohormone metabolism to the circulating pool of steroid, then the production rate will approximate the secretion rate." <b>Sources:</b> See template.</span></div></div> </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Alternative_pathways">Alternative pathways</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Steroid&action=edit&section=18" title="Edit section: Alternative pathways"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In plants and bacteria, the <a href="/wiki/Non-mevalonate_pathway" title="Non-mevalonate pathway">non-mevalonate pathway</a> (MEP pathway) uses <a href="/wiki/Pyruvic_acid" title="Pyruvic acid">pyruvate</a> and <a href="/wiki/Glyceraldehyde_3-phosphate" title="Glyceraldehyde 3-phosphate">glyceraldehyde 3-phosphate</a> as substrates to produce IPP and DMAPP.<sup id="cite_ref-pmid12735695_65-1" class="reference"><a href="#cite_note-pmid12735695-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid15012203_79-0" class="reference"><a href="#cite_note-pmid15012203-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup> </p><p>During diseases pathways otherwise not significant in healthy humans can become utilized. For example, in one form of <a href="/wiki/Congenital_adrenal_hyperplasia" title="Congenital adrenal hyperplasia">congenital adrenal hyperplasia</a> a <a href="/wiki/Congenital_adrenal_hyperplasia_due_to_21-hydroxylase_deficiency" title="Congenital adrenal hyperplasia due to 21-hydroxylase deficiency">deficiency in the 21-hydroxylase enzymatic pathway</a> leads to an excess of <a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone</a> (17-OHP) – this pathological excess of 17-OHP in turn may be converted to <a href="/wiki/Dihydrotestosterone" title="Dihydrotestosterone">dihydrotestosterone</a> (DHT, a potent androgen) through among others <a href="/wiki/CYP17A1" title="CYP17A1">17,20 Lyase</a> (a member of the <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> family of enzymes), <a href="/wiki/5%CE%B1-Reductase" title="5α-Reductase">5α-Reductase</a> and <a href="/wiki/3%CE%B1-Hydroxysteroid_dehydrogenase" title="3α-Hydroxysteroid dehydrogenase">3α-Hydroxysteroid dehydrogenase</a>.<sup id="cite_ref-pmid20671993_80-0" class="reference"><a href="#cite_note-pmid20671993-80"><span class="cite-bracket">[</span>80<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Catabolism_and_excretion">Catabolism and excretion</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Steroid&action=edit&section=19" title="Edit section: Catabolism and excretion"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Steroids are primarily oxidized by <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450 oxidase</a> enzymes, such as <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a>. These reactions introduce oxygen into the steroid ring, allowing the cholesterol to be broken up by other enzymes into bile acids.<sup id="cite_ref-pmid16872679_81-0" class="reference"><a href="#cite_note-pmid16872679-81"><span class="cite-bracket">[</span>81<span class="cite-bracket">]</span></a></sup> These acids can then be eliminated by secretion from the <a href="/wiki/Liver" title="Liver">liver</a> in <a href="/wiki/Bile" title="Bile">bile</a>.<sup id="cite_ref-pmid16749856_82-0" class="reference"><a href="#cite_note-pmid16749856-82"><span class="cite-bracket">[</span>82<span class="cite-bracket">]</span></a></sup> The expression of the <a href="/wiki/Oxidase" title="Oxidase">oxidase</a> gene can be <a href="/wiki/Downregulation_and_upregulation" title="Downregulation and upregulation">upregulated</a> by the steroid sensor <a href="/wiki/PXR" class="mw-redirect" title="PXR">PXR</a> when there is a high blood concentration of steroids.<sup id="cite_ref-pmid12372848_83-0" class="reference"><a href="#cite_note-pmid12372848-83"><span class="cite-bracket">[</span>83<span class="cite-bracket">]</span></a></sup> Steroid hormones, lacking the side chain of cholesterol and bile acids, are typically <a href="/wiki/Hydroxylation" title="Hydroxylation">hydroxylated</a> at various ring positions or <a href="/wiki/17-ketosteroid" class="mw-redirect" title="17-ketosteroid">oxidized at the 17 position</a>, <a href="/wiki/Conjugated_system" title="Conjugated system">conjugated</a> with sulfate or <a href="/wiki/Glucuronic_acid" title="Glucuronic acid">glucuronic acid</a> and excreted in the urine.<sup id="cite_ref-Steimer-WHO_84-0" class="reference"><a href="#cite_note-Steimer-WHO-84"><span class="cite-bracket">[</span>84<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Isolation,_structure_determination,_and_methods_of_analysis"><span id="Isolation.2C_structure_determination.2C_and_methods_of_analysis"></span>Isolation, structure determination, and methods of analysis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Steroid&action=edit&section=20" title="Edit section: Isolation, structure determination, and methods of analysis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Steroid <i>isolation</i>, depending on context, is the isolation of chemical matter required for <a href="/wiki/Chemical_structure" title="Chemical structure">chemical structure</a> elucidation, derivitzation or degradation chemistry, biological testing, and other research needs (generally milligrams to grams, but often more<sup id="cite_ref-Landmark_ACS_85-0" class="reference"><a href="#cite_note-Landmark_ACS-85"><span class="cite-bracket">[</span>85<span class="cite-bracket">]</span></a></sup> or the isolation of "analytical quantities" of the substance of interest (where the focus is on identifying and quantifying the substance (for example, in biological tissue or fluid). The amount isolated depends on the analytical method, but is generally less than one microgram.<sup id="cite_ref-Makin_Gower_2010_86-0" class="reference"><a href="#cite_note-Makin_Gower_2010-86"><span class="cite-bracket">[</span>86<span class="cite-bracket">]</span></a></sup><sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citing_sources" title="Wikipedia:Citing sources"><span title="This citation requires a reference to the specific page or range of pages in which the material appears. (May 2014)">page needed</span></a></i>]</sup> </p><p>The methods of isolation to achieve the two scales of product are distinct, but include <a href="/wiki/Extraction_(chemistry)" title="Extraction (chemistry)">extraction</a>, precipitation, <a href="/wiki/Adsorption" title="Adsorption">adsorption</a>, <a href="/wiki/Chromatography" title="Chromatography">chromatography</a>, and <a href="/wiki/Crystallization" title="Crystallization">crystallization</a>. In both cases, the isolated substance is purified to chemical homogeneity; combined separation and analytical methods, such as <a href="/wiki/Liquid_chromatography%E2%80%93mass_spectrometry" title="Liquid chromatography–mass spectrometry">LC-MS</a>, are chosen to be "orthogonal"—achieving their separations based on distinct modes of interaction between substance and isolating matrix—to detect a single species in the pure sample. </p><p><i>Structure determination</i> refers to the methods to determine the chemical structure of an isolated pure steroid, using an evolving array of chemical and physical methods which have included <a href="/wiki/NMR" class="mw-redirect" title="NMR">NMR</a> and small-molecule <a href="/wiki/Crystallography" title="Crystallography">crystallography</a>.<sup id="cite_ref-Lednicer_2011_2-2" class="reference"><a href="#cite_note-Lednicer_2011-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 10–19">: 10–19 </span></sup> <i>Methods of analysis</i> overlap both of the above areas, emphasizing analytical methods to determining if a steroid is present in a mixture and determining its quantity.<sup id="cite_ref-Makin_Gower_2010_86-1" class="reference"><a href="#cite_note-Makin_Gower_2010-86"><span class="cite-bracket">[</span>86<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemical_synthesis"><span class="anchor" id="Chemical_synthesis_of_steroids"></span><span class="anchor" id="Partial_and_total_chemical_synthesis"></span><span class="anchor" id="Microbial_transformations"></span>Chemical synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Steroid&action=edit&section=21" title="Edit section: Chemical synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Microbial <a href="/wiki/Catabolism" title="Catabolism">catabolism</a> of <a href="/wiki/Phytosterol" title="Phytosterol">phytosterol</a> <a href="/wiki/Side_chain" title="Side chain">side chains</a> yields C-19 steroids, C-22 steroids, and <a href="/wiki/17-ketosteroid" class="mw-redirect" title="17-ketosteroid">17-ketosteroids</a> (i.e. <a href="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">precursors</a> to <a href="/wiki/Adrenocortical_hormone" title="Adrenocortical hormone">adrenocortical hormones</a> and <a href="/wiki/Contraceptive" class="mw-redirect" title="Contraceptive">contraceptives</a>).<sup id="cite_ref-pmid987752_87-0" class="reference"><a href="#cite_note-pmid987752-87"><span class="cite-bracket">[</span>87<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Cyclodextrins_88-0" class="reference"><a href="#cite_note-Cyclodextrins-88"><span class="cite-bracket">[</span>88<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sandow-2000_89-0" class="reference"><a href="#cite_note-Sandow-2000-89"><span class="cite-bracket">[</span>89<span class="cite-bracket">]</span></a></sup> The addition and modification of <a href="/wiki/Functional_group" title="Functional group">functional groups</a> is key when producing the wide variety of medications available within this chemical classification. These modifications are performed using conventional <a href="/wiki/Organic_synthesis" title="Organic synthesis">organic synthesis</a> and/or <a href="/wiki/Biotransformation" title="Biotransformation">biotransformation</a> techniques.<sup id="cite_ref-Fried-1952_90-0" class="reference"><a href="#cite_note-Fried-1952-90"><span class="cite-bracket">[</span>90<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Capek-1966_91-0" class="reference"><a href="#cite_note-Capek-1966-91"><span class="cite-bracket">[</span>91<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Precursors">Precursors</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Steroid&action=edit&section=22" title="Edit section: Precursors"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="Semisynthesis">Semisynthesis</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Steroid&action=edit&section=23" title="Edit section: Semisynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Semisynthesis" title="Semisynthesis">semisynthesis</a> of steroids often begins from precursors such as <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a>,<sup id="cite_ref-Sandow-2000_89-1" class="reference"><a href="#cite_note-Sandow-2000-89"><span class="cite-bracket">[</span>89<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Phytosterol" title="Phytosterol">phytosterols</a>,<sup id="cite_ref-Cyclodextrins_88-1" class="reference"><a href="#cite_note-Cyclodextrins-88"><span class="cite-bracket">[</span>88<span class="cite-bracket">]</span></a></sup> or <a href="/wiki/Sapogenin" title="Sapogenin">sapogenins</a>.<sup id="cite_ref-MarkersDiscovery_92-0" class="reference"><a href="#cite_note-MarkersDiscovery-92"><span class="cite-bracket">[</span>92<span class="cite-bracket">]</span></a></sup> The efforts of <a href="/wiki/Syntex" title="Syntex">Syntex</a>, a company involved in the <a href="/wiki/Mexican_barbasco_trade" title="Mexican barbasco trade">Mexican barbasco trade</a>, used <i><a href="/wiki/Dioscorea_mexicana" title="Dioscorea mexicana">Dioscorea mexicana</a></i> to produce the sapogenin <a href="/wiki/Diosgenin" title="Diosgenin">diosgenin</a> in the early days of the synthetic steroid <a href="/wiki/Fine_chemical#Pharmaceuticals" title="Fine chemical">pharmaceutical industry</a>.<sup id="cite_ref-Landmark_ACS_85-1" class="reference"><a href="#cite_note-Landmark_ACS-85"><span class="cite-bracket">[</span>85<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Total_synthesis">Total synthesis</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Steroid&action=edit&section=24" title="Edit section: Total synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Some steroidal hormones are economically obtained only by <a href="/wiki/Total_synthesis" title="Total synthesis">total synthesis</a> from <a href="/wiki/Petrochemical" title="Petrochemical">petrochemicals</a> (e.g. 13-<a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">alkyl</a> steroids).<sup id="cite_ref-Sandow-2000_89-2" class="reference"><a href="#cite_note-Sandow-2000-89"><span class="cite-bracket">[</span>89<span class="cite-bracket">]</span></a></sup> For example, the pharmaceutical <a href="/wiki/Norgestrel" title="Norgestrel">Norgestrel</a> begins from <a href="/wiki/Methoxy" class="mw-redirect" title="Methoxy">methoxy</a>-<a href="/wiki/1-tetralone" class="mw-redirect" title="1-tetralone">1-tetralone</a>, a petrochemical derived from <a href="/wiki/Phenol" title="Phenol">phenol</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Research_awards"><span class="anchor" id="History"></span>Research awards</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Steroid&action=edit&section=25" title="Edit section: Research awards"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A number of <a href="/wiki/Nobel_Prize" title="Nobel Prize">Nobel Prizes</a> have been awarded for steroid research, including: </p> <ul><li>1927 (<a href="/wiki/Nobel_Prize_in_Chemistry" title="Nobel Prize in Chemistry">Chemistry</a>) <a href="/wiki/Heinrich_Otto_Wieland" title="Heinrich Otto Wieland">Heinrich Otto Wieland</a> — Constitution of bile acids and sterols and their connection to vitamins<sup id="cite_ref-Nobel_Prize_Chemistry_1927_93-0" class="reference"><a href="#cite_note-Nobel_Prize_Chemistry_1927-93"><span class="cite-bracket">[</span>93<span class="cite-bracket">]</span></a></sup></li> <li>1928 (Chemistry) <a href="/wiki/Adolf_Otto_Reinhold_Windaus" class="mw-redirect" title="Adolf Otto Reinhold Windaus">Adolf Otto Reinhold Windaus</a> — Constitution of sterols and their connection to vitamins<sup id="cite_ref-Nobel_Prize_Chemistry_1928_94-0" class="reference"><a href="#cite_note-Nobel_Prize_Chemistry_1928-94"><span class="cite-bracket">[</span>94<span class="cite-bracket">]</span></a></sup></li> <li>1939 (Chemistry) <a href="/wiki/Adolf_Butenandt" title="Adolf Butenandt">Adolf Butenandt</a> and <a href="/wiki/Leopold_Ruzicka" class="mw-redirect" title="Leopold Ruzicka">Leopold Ružička</a> — Isolation and structural studies of steroid sex hormones, and related studies on higher <a href="/wiki/Terpene" title="Terpene">terpenes</a><sup id="cite_ref-Nobel_Prize_Chemistry_1939_95-0" class="reference"><a href="#cite_note-Nobel_Prize_Chemistry_1939-95"><span class="cite-bracket">[</span>95<span class="cite-bracket">]</span></a></sup></li> <li>1950 (<a href="/wiki/Nobel_Prize_in_Physiology_or_Medicine" title="Nobel Prize in Physiology or Medicine">Physiology or Medicine</a>) <a href="/wiki/Edward_Calvin_Kendall" title="Edward Calvin Kendall">Edward Calvin Kendall</a>, <a href="/wiki/Tadeus_Reichstein" class="mw-redirect" title="Tadeus Reichstein">Tadeus Reichstein</a>, and <a href="/wiki/Philip_Hench" class="mw-redirect" title="Philip Hench">Philip Hench</a> — Structure and biological effects of <a href="/wiki/Adrenocortical_hormone" title="Adrenocortical hormone">adrenal hormones</a><sup id="cite_ref-Nobel_Prize_Medicine_1950_96-0" class="reference"><a href="#cite_note-Nobel_Prize_Medicine_1950-96"><span class="cite-bracket">[</span>96<span class="cite-bracket">]</span></a></sup></li> <li>1965 (Chemistry) <a href="/wiki/Robert_Burns_Woodward" title="Robert Burns Woodward">Robert Burns Woodward</a> — In part, for the synthesis of cholesterol, <a href="/wiki/Cortisone" title="Cortisone">cortisone</a>, and <a href="/wiki/Lanosterol" title="Lanosterol">lanosterol</a><sup id="cite_ref-Nobel_Prize_Chemistry_1965_97-0" class="reference"><a href="#cite_note-Nobel_Prize_Chemistry_1965-97"><span class="cite-bracket">[</span>97<span class="cite-bracket">]</span></a></sup></li> <li>1969 (Chemistry) <a href="/wiki/Derek_Barton" title="Derek Barton">Derek Barton</a> and <a href="/wiki/Odd_Hassel" title="Odd Hassel">Odd Hassel</a> — Development of the concept of conformation in chemistry, emphasizing the steroid nucleus<sup id="cite_ref-Nobel_Prize_Chemistry_1969_98-0" class="reference"><a href="#cite_note-Nobel_Prize_Chemistry_1969-98"><span class="cite-bracket">[</span>98<span class="cite-bracket">]</span></a></sup></li> <li>1975 (Chemistry) <a href="/wiki/Vladimir_Prelog" title="Vladimir Prelog">Vladimir Prelog</a> — In part, for developing methods to determine the stereochemical course of cholesterol biosynthesis from <a href="/wiki/Mevalonic_acid" title="Mevalonic acid">mevalonic acid</a> via <a href="/wiki/Squalene" title="Squalene">squalene</a><sup id="cite_ref-Nobel_Prize_Chemistry_1975_99-0" class="reference"><a href="#cite_note-Nobel_Prize_Chemistry_1975-99"><span class="cite-bracket">[</span>99<span class="cite-bracket">]</span></a></sup></li></ul> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Steroid&action=edit&section=26" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1184024115">.mw-parser-output .div-col{margin-top:0.3em;column-width:30em}.mw-parser-output .div-col-small{font-size:90%}.mw-parser-output .div-col-rules{column-rule:1px solid #aaa}.mw-parser-output .div-col dl,.mw-parser-output .div-col ol,.mw-parser-output .div-col ul{margin-top:0}.mw-parser-output .div-col li,.mw-parser-output .div-col dd{page-break-inside:avoid;break-inside:avoid-column}</style><div class="div-col"> <ul><li><a href="/wiki/Adrenal_gland" title="Adrenal gland">Adrenal gland</a></li> <li><a href="/wiki/Batrachotoxin" title="Batrachotoxin">Batrachotoxin</a></li> <li><a href="/wiki/List_of_steroid_abbreviations" title="List of steroid abbreviations">List of steroid abbreviations</a></li> <li><a href="/wiki/List_of_steroids" title="List of steroids">List of steroids</a></li> <li><a href="/wiki/Membrane_steroid_receptor" title="Membrane steroid receptor">Membrane steroid receptor</a></li> <li><a href="/wiki/Pheromone" title="Pheromone">Pheromone</a></li> <li><a href="/wiki/Reverse_cholesterol_transport" title="Reverse cholesterol transport">Reverse cholesterol transport</a></li> <li><a href="/wiki/Steroidogenesis_inhibitor" title="Steroidogenesis inhibitor">Steroidogenesis inhibitor</a></li> <li><a href="/wiki/Steroidogenic_acute_regulatory_protein" title="Steroidogenic acute regulatory protein">Steroidogenic acute regulatory protein</a></li> <li><a href="/wiki/Steroidogenic_enzyme" title="Steroidogenic enzyme">Steroidogenic enzyme</a></li></ul> </div> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Steroid&action=edit&section=27" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-IUPAC_steroids-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-IUPAC_steroids_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-IUPAC_steroids_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-IUPAC_steroids_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-IUPAC_steroids_1-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFMossthe_Working_Party_of_the_IUPAC-IUB_Joint_Commission_on_Biochemical_Nomenclature1989" class="citation journal cs1">Moss GP, the Working Party of the IUPAC-IUB Joint Commission on Biochemical Nomenclature (1989). <a rel="nofollow" class="external text" href="http://iupac.org/publications/pac/pdf/1989/pdf/6110x1783.pdf">"Nomenclature of steroids, recommendations 1989"</a> <span class="cs1-format">(PDF)</span>. <i><a href="/wiki/Pure_and_Applied_Chemistry" title="Pure and Applied Chemistry">Pure Appl. Chem.</a></i> <b>61</b> (10): 1783–1822. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fpac198961101783">10.1351/pac198961101783</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:97612891">97612891</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20121130182412/http://iupac.org/publications/pac/pdf/1989/pdf/6110x1783.pdf">Archived</a> <span class="cs1-format">(PDF)</span> from the original on 30 November 2012<span class="reference-accessdate">. Retrieved <span class="nowrap">21 February</span> 2012</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pure+Appl.+Chem.&rft.atitle=Nomenclature+of+steroids%2C+recommendations+1989&rft.volume=61&rft.issue=10&rft.pages=1783-1822&rft.date=1989&rft_id=info%3Adoi%2F10.1351%2Fpac198961101783&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A97612891%23id-name%3DS2CID&rft.aulast=Moss&rft.aufirst=GP&rft.au=the+Working+Party+of+the+IUPAC-IUB+Joint+Commission+on+Biochemical+Nomenclature&rft_id=http%3A%2F%2Fiupac.org%2Fpublications%2Fpac%2Fpdf%2F1989%2Fpdf%2F6110x1783.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span> <i>Also available with the same authors at</i> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation journal cs1">"IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN). The nomenclature of steroids. Recommendations 1989". <i>European Journal of Biochemistry</i>. <b>186</b> (3): 429–458. December 1989. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1432-1033.1989.tb15228.x">10.1111/j.1432-1033.1989.tb15228.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/2606099">2606099</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=European+Journal+of+Biochemistry&rft.atitle=IUPAC-IUB+Joint+Commission+on+Biochemical+Nomenclature+%28JCBN%29.+The+nomenclature+of+steroids.+Recommendations+1989&rft.volume=186&rft.issue=3&rft.pages=429-458&rft.date=1989-12&rft_id=info%3Adoi%2F10.1111%2Fj.1432-1033.1989.tb15228.x&rft_id=info%3Apmid%2F2606099&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span>; <i>Also available online at</i> <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.chem.qmul.ac.uk/iupac/steroid/3S01.html">"The Nomenclature of Steroids"</a>. London, GBR: Queen Mary University of London. p. 3S-1.4. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170910193822/http://www.chem.qmul.ac.uk/iupac/steroid/3S01.html">Archived</a> from the original on 10 September 2017<span class="reference-accessdate">. Retrieved <span class="nowrap">10 May</span> 2014</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=The+Nomenclature+of+Steroids&rft.place=London%2C+GBR&rft.pages=3S-1.4&rft.pub=Queen+Mary+University+of+London&rft_id=http%3A%2F%2Fwww.chem.qmul.ac.uk%2Fiupac%2Fsteroid%2F3S01.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span></span> </li> <li id="cite_note-Lednicer_2011-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-Lednicer_2011_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Lednicer_2011_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Lednicer_2011_2-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLednicer2011" class="citation book cs1">Lednicer D (2011). <i>Steroid Chemistry at a Glance</i>. Hoboken: Wiley. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-470-66084-3" title="Special:BookSources/978-0-470-66084-3"><bdi>978-0-470-66084-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Steroid+Chemistry+at+a+Glance&rft.place=Hoboken&rft.pub=Wiley&rft.date=2011&rft.isbn=978-0-470-66084-3&rft.aulast=Lednicer&rft.aufirst=D&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span></span> </li> <li id="cite_note-pmid16236742-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid16236742_3-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRhenCidlowski2005" class="citation journal cs1">Rhen T, Cidlowski JA (October 2005). "Antiinflammatory action of glucocorticoids--new mechanisms for old drugs". <i>The New England Journal of Medicine</i>. <b>353</b> (16): 1711–1723. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1056%2FNEJMra050541">10.1056/NEJMra050541</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/16236742">16236742</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:5744727">5744727</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+New+England+Journal+of+Medicine&rft.atitle=Antiinflammatory+action+of+glucocorticoids--new+mechanisms+for+old+drugs&rft.volume=353&rft.issue=16&rft.pages=1711-1723&rft.date=2005-10&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A5744727%23id-name%3DS2CID&rft_id=info%3Apmid%2F16236742&rft_id=info%3Adoi%2F10.1056%2FNEJMra050541&rft.aulast=Rhen&rft.aufirst=T&rft.au=Cidlowski%2C+JA&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span></span> </li> <li id="cite_note-urlLanosterol_biosynthesis-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-urlLanosterol_biosynthesis_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-urlLanosterol_biosynthesis_4-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20110308161403/http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/terp/lanost.html">"Lanosterol biosynthesis"</a>. <i>Recommendations on Biochemical & Organic Nomenclature, Symbols & Terminology</i>. International Union Of Biochemistry And Molecular Biology. Archived from <a rel="nofollow" class="external text" href="http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/terp/lanost.html">the original</a> on 8 March 2011<span class="reference-accessdate">. Retrieved <span class="nowrap">28 November</span> 2006</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Recommendations+on+Biochemical+%26+Organic+Nomenclature%2C+Symbols+%26+Terminology&rft.atitle=Lanosterol+biosynthesis&rft_id=http%3A%2F%2Fwww.chem.qmul.ac.uk%2Fiubmb%2Fenzyme%2Freaction%2Fterp%2Flanost.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span></span> </li> <li id="cite_note-Harper-Sterol-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-Harper-Sterol_5-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHarper" class="citation web cs1">Harper D. <a rel="nofollow" class="external text" href="https://www.etymonline.com/word/sterol">"sterol | Etymology, origin and meaning of sterol by etymonline"</a>. <i>Online Etymology Dictionary</i>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230319092627/https://www.etymonline.com/word/sterol">Archived</a> from the original on 19 March 2023<span class="reference-accessdate">. Retrieved <span class="nowrap">19 March</span> 2023</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Online+Etymology+Dictionary&rft.atitle=sterol+%7C+Etymology%2C+origin+and+meaning+of+sterol+by+etymonline&rft.aulast=Harper&rft.aufirst=D&rft_id=https%3A%2F%2Fwww.etymonline.com%2Fword%2Fsterol&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span></span> </li> <li id="cite_note-Chevreul-1815-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-Chevreul-1815_6-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChevreul1815" class="citation journal cs1 cs1-prop-foreign-lang-source"><a href="/wiki/Michel_Eug%C3%A8ne_Chevreul" title="Michel Eugène Chevreul">Chevreul ME</a> (8 May 1815). <a rel="nofollow" class="external text" href="https://www.deutsche-digitale-bibliothek.de/item/254EFGXQPJNOVNAF575XO6K7MXD7EQOZ">"Recherches chimiques sur les corps gras, et particulièrement sur leurs combinaisons avec les alcalis. Sixième mémoire. Examen des graisses d'homme, de mouton, de boeuf, de jaguar et d'oie"</a> [Chemical research on fatty substances, and particularly on their combinations with alkalis. Sixth memoir. Examination of human, sheep, beef, jaguar and goose fats]. <i>Annales de Chimie et de Physique (Annals of Chemistry and Physics)</i> (in French). <b>2</b>: 339–372. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20231004081946/https://www.deutsche-digitale-bibliothek.de/item/254EFGXQPJNOVNAF575XO6K7MXD7EQOZ">Archived</a> from the original on 4 October 2023<span class="reference-accessdate">. Retrieved <span class="nowrap">11 September</span> 2023</span> – via Deutsche Digitale Bibliothek.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annales+de+Chimie+et+de+Physique+%28Annals+of+Chemistry+and+Physics%29&rft.atitle=Recherches+chimiques+sur+les+corps+gras%2C+et+particuli%C3%A8rement+sur+leurs+combinaisons+avec+les+alcalis.+Sixi%C3%A8me+m%C3%A9moire.+Examen+des+graisses+d%27homme%2C+de+mouton%2C+de+boeuf%2C+de+jaguar+et+d%27oie&rft.volume=2&rft.pages=339-372&rft.date=1815-05-08&rft.aulast=Chevreul&rft.aufirst=ME&rft_id=https%3A%2F%2Fwww.deutsche-digitale-bibliothek.de%2Fitem%2F254EFGXQPJNOVNAF575XO6K7MXD7EQOZ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span></span> </li> <li id="cite_note-Arago-1816-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-Arago-1816_7-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAragoGay-Lussac1816" class="citation book cs1 cs1-prop-foreign-lang-source">Arago F, Gay-Lussac JL (1816). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=DHCz1nhhYL8C&pg=PA346"><i>Annales de chimie et de physique (Annals of Chemistry and Physics)</i></a> (in French). Chez Crochard. p. 346. <q><span class="cs1-kern-left"></span>"Je nommerai <i>cholesterine</i>, de χολη, bile, et στερεος, solide, la substance cristallisée des calculs biliares humains, ... " (I will name <i>cholesterine</i> – from χολη (bile) and στερεος (solid) – the crystalized substance from human gallstones ... )</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Annales+de+chimie+et+de+physique+%28Annals+of+Chemistry+and+Physics%29&rft.pages=346&rft.pub=Chez+Crochard&rft.date=1816&rft.aulast=Arago&rft.aufirst=F&rft.au=Gay-Lussac%2C+JL&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DDHCz1nhhYL8C%26pg%3DPA346&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span></span> </li> <li id="cite_note-R-2.4.1_Fusion_nomenclature-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-R-2.4.1_Fusion_nomenclature_8-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.acdlabs.com/iupac/nomenclature/93/r93_229.htm">"R-2.4.1 Fusion nomenclature"</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20231122015342/https://www.acdlabs.com/iupac/nomenclature/93/r93_229.htm">Archived</a> from the original on 22 November 2023<span class="reference-accessdate">. Retrieved <span class="nowrap">22 November</span> 2023</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=R-2.4.1+Fusion+nomenclature&rft_id=https%3A%2F%2Fwww.acdlabs.com%2Fiupac%2Fnomenclature%2F93%2Fr93_229.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span></span> </li> <li id="cite_note-pmid36677830-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid36677830_9-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFYangKrinCaiPoopari2023" class="citation journal cs1">Yang Y, Krin A, Cai X, Poopari MR, Zhang Y, Cheeseman JR, Xu Y (January 2023). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9864676">"Conformations of Steroid Hormones: Infrared and Vibrational Circular Dichroism Spectroscopy"</a>. <i>Molecules</i>. <b>28</b> (2): 771. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.3390%2Fmolecules28020771">10.3390/molecules28020771</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9864676">9864676</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/36677830">36677830</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Molecules&rft.atitle=Conformations+of+Steroid+Hormones%3A+Infrared+and+Vibrational+Circular+Dichroism+Spectroscopy&rft.volume=28&rft.issue=2&rft.pages=771&rft.date=2023-01&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC9864676%23id-name%3DPMC&rft_id=info%3Apmid%2F36677830&rft_id=info%3Adoi%2F10.3390%2Fmolecules28020771&rft.aulast=Yang&rft.aufirst=Y&rft.au=Krin%2C+A&rft.au=Cai%2C+X&rft.au=Poopari%2C+MR&rft.au=Zhang%2C+Y&rft.au=Cheeseman%2C+JR&rft.au=Xu%2C+Y&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC9864676&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span></span> </li> <li id="cite_note-Hill-1991-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-Hill-1991_10-0">^</a></b></span> <span class="reference-text">Also available in print at <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHillMakinKirkMurphy1991" class="citation book cs1">Hill RA, Makin HL, Kirk DN, Murphy GM (1991). <a rel="nofollow" class="external text" href="https://books.google.com/books?isbn=0-412-27060-9"><i>Dictionary of Steroids</i></a>. London, GBR: Chapman and Hall. pp. xxx–lix. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-412-27060-4" title="Special:BookSources/978-0-412-27060-4"><bdi>978-0-412-27060-4</bdi></a><span class="reference-accessdate">. Retrieved <span class="nowrap">20 June</span> 2015</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Dictionary+of+Steroids&rft.place=London%2C+GBR&rft.pages=xxx-lix&rft.pub=Chapman+and+Hall&rft.date=1991&rft.isbn=978-0-412-27060-4&rft.aulast=Hill&rft.aufirst=RA&rft.au=Makin%2C+HL&rft.au=Kirk%2C+DN&rft.au=Murphy%2C+GM&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fisbn%3D0-412-27060-9&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span></span> </li> <li id="cite_note-Rogozkin1991-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-Rogozkin1991_11-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRogozkin1991" class="citation book cs1">Rogozkin VA (14 June 1991). <a rel="nofollow" class="external text" href="https://books.auho.com/books?id=hRsnmJRF1WgC&pg=PA1">"Anabolic Androgenic Steroids: Structure, Nomenclature, and Classification, Biological Properties"</a>. <i>Metabolism of Anabolic-Androgenic Steroids</i>. CRC Press. pp. 1–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-8493-6415-0" title="Special:BookSources/978-0-8493-6415-0"><bdi>978-0-8493-6415-0</bdi></a>. <q>The steroid structural base is a steran nucleus, a polycyclic C17 steran skeleton consisting of three condensed cyclohexane rings in nonlinear or phenanthrene junction (A, B, and C), and a cyclopentane ring (D).1,2</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Anabolic+Androgenic+Steroids%3A+Structure%2C+Nomenclature%2C+and+Classification%2C+Biological+Properties&rft.btitle=Metabolism+of+Anabolic-Androgenic+Steroids&rft.pages=1-&rft.pub=CRC+Press&rft.date=1991-06-14&rft.isbn=978-0-8493-6415-0&rft.aulast=Rogozkin&rft.aufirst=VA&rft_id=https%3A%2F%2Fbooks.auho.com%2Fbooks%3Fid%3DhRsnmJRF1WgC%26pg%3DPA1&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span><sup class="noprint Inline-Template"><span style="white-space: nowrap;">[<i><a href="/wiki/Wikipedia:Link_rot" title="Wikipedia:Link rot"><span title=" Dead link tagged March 2024">permanent dead link</span></a></i><span style="visibility:hidden; color:transparent; padding-left:2px">‍</span>]</span></sup></span> </li> <li id="cite_note-Urich1994-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-Urich1994_12-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFUrich1994" class="citation book cs1">Urich K (16 September 1994). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=GLbcWyeaCGQC&pg=PA624">"Sterols and Steroids"</a>. <i>Comparative Animal Biochemistry</i>. Springer Science & Business Media. pp. 624–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-540-57420-0" title="Special:BookSources/978-3-540-57420-0"><bdi>978-3-540-57420-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Sterols+and+Steroids&rft.btitle=Comparative+Animal+Biochemistry&rft.pages=624-&rft.pub=Springer+Science+%26+Business+Media&rft.date=1994-09-16&rft.isbn=978-3-540-57420-0&rft.aulast=Urich&rft.aufirst=K&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DGLbcWyeaCGQC%26pg%3DPA624&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span></span> </li> <li id="cite_note-FOOTNOTEGreep2013-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-FOOTNOTEGreep2013_13-0">^</a></b></span> <span class="reference-text"><a href="#CITEREFGreep2013">Greep 2013</a>.</span> </li> <li id="cite_note-wj-14"><span class="mw-cite-backlink">^ <a href="#cite_ref-wj_14-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-wj_14-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-wj_14-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-wj_14-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-wj_14-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-wj_14-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-wj_14-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-wj_14-7"><sup><i><b>h</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMasiutinYadav2023" class="citation journal cs1">Masiutin MM, Yadav MK (3 April 2023). <a class="external text" href="https://upload.wikimedia.org/wikiversity/en/a/a7/Alternative_androgens_pathways.pdf">"Alternative androgen pathways"</a> <span class="cs1-format">(PDF)</span>. <i>WikiJournal of Medicine</i>. <b>10</b>: 29. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.15347%2FWJM%2F2023.003">10.15347/WJM/2023.003</a></span>. <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:257943362">257943362</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=WikiJournal+of+Medicine&rft.atitle=Alternative+androgen+pathways&rft.volume=10&rft.pages=29&rft.date=2023-04-03&rft_id=info%3Adoi%2F10.15347%2FWJM%2F2023.003&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A257943362%23id-name%3DS2CID&rft.aulast=Masiutin&rft.aufirst=MM&rft.au=Yadav%2C+MK&rft_id=https%3A%2F%2Fupload.wikimedia.org%2Fwikiversity%2Fen%2Fa%2Fa7%2FAlternative_androgens_pathways.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span><i><span typeof="mw:File"><a href="//creativecommons.org/licenses/by/4.0/" title="creativecommons:by/4.0/"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Creative_Commons_by_small.svg/80px-Creative_Commons_by_small.svg.png" decoding="async" width="80" height="15" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Creative_Commons_by_small.svg/120px-Creative_Commons_by_small.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/65/Creative_Commons_by_small.svg/160px-Creative_Commons_by_small.svg.png 2x" data-file-width="80" data-file-height="15" /></a></span> This article incorporates text from this source, which is available under the <a href="//creativecommons.org/licenses/by/4.0/" class="extiw" title="creativecommons:by/4.0/">CC BY 4.0</a> license.</i></span> </li> <li id="cite_note-pmid2606099-skeleton-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid2606099-skeleton_15-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation journal cs1">"IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN). The nomenclature of steroids. Recommendations 1989". <i>Eur J Biochem</i>. <b>186</b> (3): 430. 1989. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1432-1033.1989.tb15228.x">10.1111/j.1432-1033.1989.tb15228.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/2606099">2606099</a>. p. 430: <q>3S‐1.0. Definition of steroids and sterols. Steroids are compounds possessing the skeleton of cyclopenta[a]phenanthrene or a skeleton derived therefrom by one or more bond scissions or ring expansions or contractions. Methyl groups are normally present at C-10 and C-13. An alkyl side chain may also be present at C-17. Sterols are steroids carrying a hydroxyl group at C-3 and most of the skeleton of cholestane.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Eur+J+Biochem&rft.atitle=IUPAC-IUB+Joint+Commission+on+Biochemical+Nomenclature+%28JCBN%29.+The+nomenclature+of+steroids.+Recommendations+1989&rft.volume=186&rft.issue=3&rft.pages=430&rft.date=1989&rft_id=info%3Adoi%2F10.1111%2Fj.1432-1033.1989.tb15228.x&rft_id=info%3Apmid%2F2606099&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span></span> </li> <li id="cite_note-pmid2606099-parent-elisions-16"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid2606099-parent-elisions_16-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid2606099-parent-elisions_16-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation journal cs1">"IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN). The nomenclature of steroids. Recommendations 1989". <i>Eur J Biochem</i>. <b>186</b> (3): 429–458. 1989. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1432-1033.1989.tb15228.x">10.1111/j.1432-1033.1989.tb15228.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/2606099">2606099</a>. p. 441: <q>3S-4. FUNCTIONAL GROUPS. 3S-4.0. General. Nearly all biologically important steroids are derivatives of the parent hydrocarbons (cf. Table 1) carrying various functional groups. [...] Suffixes are added to the name of the saturated or unsaturated parent system (see 33-2.5), the terminal e of -ane, -ene, -yne, -adiene etc. being elided before a vowel (presence or absence of numerals has no effect on such elisions).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Eur+J+Biochem&rft.atitle=IUPAC-IUB+Joint+Commission+on+Biochemical+Nomenclature+%28JCBN%29.+The+nomenclature+of+steroids.+Recommendations+1989&rft.volume=186&rft.issue=3&rft.pages=429-458&rft.date=1989&rft_id=info%3Adoi%2F10.1111%2Fj.1432-1033.1989.tb15228.x&rft_id=info%3Apmid%2F2606099&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span></span> </li> <li id="cite_note-pmid2606099-trivial-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid2606099-trivial_17-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation journal cs1"><a rel="nofollow" class="external text" href="https://iupac.qmul.ac.uk/steroid/3S04b.html#3S49">"IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN). The nomenclature of steroids. Recommendations 1989, chapter 3S-4.9"</a>. <i>European Journal of Biochemistry</i>. <b>186</b> (3): 429–458. December 1989. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1432-1033.1989.tb15228.x">10.1111/j.1432-1033.1989.tb15228.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/2606099">2606099</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20240219010052/https://iupac.qmul.ac.uk/steroid/3S04b.html#3S49">Archived</a> from the original on 19 February 2024<span class="reference-accessdate">. Retrieved <span class="nowrap">19 February</span> 2024</span>. <q>3S‐4.9. Trivial names of important steroids Examples of trivial names retained for important steroid derivatives, these being mostly natural compounds of significant biological activity, are given in Table 2</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=European+Journal+of+Biochemistry&rft.atitle=IUPAC-IUB+Joint+Commission+on+Biochemical+Nomenclature+%28JCBN%29.+The+nomenclature+of+steroids.+Recommendations+1989%2C+chapter+3S-4.9&rft.volume=186&rft.issue=3&rft.pages=429-458&rft.date=1989-12&rft_id=info%3Adoi%2F10.1111%2Fj.1432-1033.1989.tb15228.x&rft_id=info%3Apmid%2F2606099&rft_id=https%3A%2F%2Fiupac.qmul.ac.uk%2Fsteroid%2F3S04b.html%233S49&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span></span> </li> <li id="cite_note-pmid2606099-rs-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid2606099-rs_18-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation journal cs1">"IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN). The nomenclature of steroids. Recommendations 1989, chapter 3S-1.4". <i>European Journal of Biochemistry</i>. <b>186</b> (3): 429–458. December 1989. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1432-1033.1989.tb15228.x">10.1111/j.1432-1033.1989.tb15228.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/2606099">2606099</a>. p. 431: <q>3S‐1.4. Orientation of projection formulae. When the rings of a steroid are denoted as projections onto the plane of the paper, the formula is normally to be oriented as in 2a. An atom or group attached to a ring depicted as in the orientation 2a is termed α (alpha) if it lies below the plane of the paper or β (beta) if it lies above the plane of the paper.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=European+Journal+of+Biochemistry&rft.atitle=IUPAC-IUB+Joint+Commission+on+Biochemical+Nomenclature+%28JCBN%29.+The+nomenclature+of+steroids.+Recommendations+1989%2C+chapter+3S-1.4&rft.volume=186&rft.issue=3&rft.pages=429-458&rft.date=1989-12&rft_id=info%3Adoi%2F10.1111%2Fj.1432-1033.1989.tb15228.x&rft_id=info%3Apmid%2F2606099&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span></span> </li> <li id="cite_note-norc-rs-19"><span class="mw-cite-backlink"><b><a href="#cite_ref-norc-rs_19-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFavrePowell2014" class="citation book cs1">Favre HA, Powell WH (2014). "P-91". <i>Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013</i>. The Royal Society of Chemistry. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2F9781849733069">10.1039/9781849733069</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-85404-182-4" title="Special:BookSources/978-0-85404-182-4"><bdi>978-0-85404-182-4</bdi></a>. p. 868: <q>P‐91.2.1.1 Cahn-Ingold-Prelog (CIP) stereodescriptors. Some stereodescriptors described in the Cahn-Ingold-Prelog (CIP) priority system, called 'CIP stereodescriptors', are recommended to specify the configuration of organic compounds, as described and exemplified in this Chapter and applied in Chapters P‐1 through P‐8, and in the nomenclature of natural products in Chapter P-10. The following stereodescriptors are used as preferred stereodescriptors (see P‐92.1.2): (a) 'R' and 'S', to designate the absolute configuration of tetracoordinate (quadriligant) chirality centers;</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=P-91&rft.btitle=Nomenclature+of+Organic+Chemistry+%E2%80%93+IUPAC+Recommendations+and+Preferred+Names+2013&rft.pages=868&rft.pub=The+Royal+Society+of+Chemistry&rft.date=2014&rft_id=info%3Adoi%2F10.1039%2F9781849733069&rft.isbn=978-0-85404-182-4&rft.aulast=Favre&rft.aufirst=HA&rft.au=Powell%2C+WH&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span></span> </li> <li id="cite_note-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-20">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_%28Soderberg%29/03%3A_Conformations_and_Stereochemistry/3.05%3A_Naming_chiral_centers-_the_R_and_S_system">"3.5: Naming chiral centers- the R and S system"</a>. 11 August 2018. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20231101155825/https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book:_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_(Soderberg)/03:_Conformations_and_Stereochemistry/3.05:_Naming_chiral_centers-_the_R_and_S_system">Archived</a> from the original on 1 November 2023<span class="reference-accessdate">. Retrieved <span class="nowrap">16 October</span> 2023</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=3.5%3A+Naming+chiral+centers-+the+R+and+S+system&rft.date=2018-08-11&rft_id=https%3A%2F%2Fchem.libretexts.org%2FBookshelves%2FOrganic_Chemistry%2FBook%253A_Organic_Chemistry_with_a_Biological_Emphasis_v2.0_%2528Soderberg%2529%2F03%253A_Conformations_and_Stereochemistry%2F3.05%253A_Naming_chiral_centers-_the_R_and_S_system&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span></span> </li> <li id="cite_note-norc-deoxy-21"><span class="mw-cite-backlink"><b><a href="#cite_ref-norc-deoxy_21-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFavrePowell2014" class="citation book cs1">Favre HA, Powell WH (2014). "P-13.8.1.1". <i>Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013</i>. The Royal Society of Chemistry. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2F9781849733069">10.1039/9781849733069</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-85404-182-4" title="Special:BookSources/978-0-85404-182-4"><bdi>978-0-85404-182-4</bdi></a>. p. 66: <q>P‐13.8.1.1 The prefix 'de' (not 'des'), followed by the name of a group or atom (other than hydrogen), denotes removal (or loss) of that group and addition of the necessary hydrogen atoms, i.e., exchange of that group with hydrogen atoms. As an exception, 'deoxy', when applied to hydroxy compounds, denotes the removal of an oxygen atom from an –OH group with the reconnection of the hydrogen atom. 'Deoxy' is extensively used as a subtractive prefix in carbohydrate nomenclature (see P‐102.5.3).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=P-13.8.1.1&rft.btitle=Nomenclature+of+Organic+Chemistry+%E2%80%93+IUPAC+Recommendations+and+Preferred+Names+2013&rft.pages=66&rft.pub=The+Royal+Society+of+Chemistry&rft.date=2014&rft_id=info%3Adoi%2F10.1039%2F9781849733069&rft.isbn=978-0-85404-182-4&rft.aulast=Favre&rft.aufirst=HA&rft.au=Powell%2C+WH&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span></span> </li> <li id="cite_note-pmid2606099-numbering-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid2606099-numbering_22-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation journal cs1">"IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN). The nomenclature of steroids. Recommendations 1989". <i>Eur J Biochem</i>. <b>186</b> (3): 430. 1989. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1432-1033.1989.tb15228.x">10.1111/j.1432-1033.1989.tb15228.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/2606099">2606099</a>. p. 430: <q>3S-1.1. Numbering and ring letters. Steroids are numbered and rings are lettered as in formula 1</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Eur+J+Biochem&rft.atitle=IUPAC-IUB+Joint+Commission+on+Biochemical+Nomenclature+%28JCBN%29.+The+nomenclature+of+steroids.+Recommendations+1989&rft.volume=186&rft.issue=3&rft.pages=430&rft.date=1989&rft_id=info%3Adoi%2F10.1111%2Fj.1432-1033.1989.tb15228.x&rft_id=info%3Apmid%2F2606099&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span></span> </li> <li id="cite_note-pmid2606099-unsaturation-23"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid2606099-unsaturation_23-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid2606099-unsaturation_23-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation journal cs1">"IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN). The nomenclature of steroids. Recommendations 1989". <i>Eur J Biochem</i>. <b>186</b> (3): 436–437. 1989. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1432-1033.1989.tb15228.x">10.1111/j.1432-1033.1989.tb15228.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/2606099">2606099</a>. p. 436-437: <q>3S‐2.5 Unsaturation. Unsaturation is indicated by changing -ane to -ene, -adiene, -yne etc., or -an- to -en-, -adien-, -yn- etc. Examples: Androst-5-ene, not 5-androstene; 5α-Cholest-6-ene; 5β-Cholesta-7,9(11)-diene; 5α-Cholest-6-en-3β-ol. Notes. 1) It is now recommended that the locant of a double bond is always adjacent to the syllable designating the unsaturation.[...] 3) The use of Δ (Greek capital delta) character is not recommended to designate unsaturation in individual names. It may be used, however, in generic terms, like 'Δ<sup>5</sup>-steroids'<span class="cs1-kern-right"></span></q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Eur+J+Biochem&rft.atitle=IUPAC-IUB+Joint+Commission+on+Biochemical+Nomenclature+%28JCBN%29.+The+nomenclature+of+steroids.+Recommendations+1989&rft.volume=186&rft.issue=3&rft.pages=436-437&rft.date=1989&rft_id=info%3Adoi%2F10.1111%2Fj.1432-1033.1989.tb15228.x&rft_id=info%3Apmid%2F2606099&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span></span> </li> <li id="cite_note-norc-24"><span class="mw-cite-backlink"><b><a href="#cite_ref-norc_24-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFavrePowell2014" class="citation book cs1">Favre HA, Powell WH (2014). "P-3". <i>Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013</i>. The Royal Society of Chemistry. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2F9781849733069">10.1039/9781849733069</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-85404-182-4" title="Special:BookSources/978-0-85404-182-4"><bdi>978-0-85404-182-4</bdi></a>. <q>P-31.2.2 General methodology. 'Hydro' and 'dehydro' prefixes are associated with hydrogenation and dehydrogenation, respectively, of a double bond; thus, multiplying prefixes of even values, as 'di', 'tetra', etc. are used to indicate the saturation of double bond(s), for example 'dihydro', 'tetrahydro'; or creation of double (or triple) bonds, as 'didehydro', etc. In names, they are placed immediately at the front of the name of the parent hydride and in front of any nondetachable prefixes. Indicated hydrogen atoms have priority over 'hydro' prefixes for low locants. If indicated hydrogen atoms are present in a name, the 'hydro' prefixes precede them.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=P-3&rft.btitle=Nomenclature+of+Organic+Chemistry+%E2%80%93+IUPAC+Recommendations+and+Preferred+Names+2013&rft.pub=The+Royal+Society+of+Chemistry&rft.date=2014&rft_id=info%3Adoi%2F10.1039%2F9781849733069&rft.isbn=978-0-85404-182-4&rft.aulast=Favre&rft.aufirst=HA&rft.au=Powell%2C+WH&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span></span> </li> <li id="cite_note-pmid21051590-25"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid21051590_25-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid21051590_25-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-pmid21051590_25-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-pmid21051590_25-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-pmid21051590_25-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-pmid21051590_25-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-pmid21051590_25-6"><sup><i><b>g</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMillerAuchus2011" class="citation journal cs1">Miller WL, Auchus RJ (February 2011). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3365799">"The molecular biology, biochemistry, and physiology of human steroidogenesis and its disorders"</a>. <i>Endocr Rev</i>. <b>32</b> (1): 81–151. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1210%2Fer.2010-0013">10.1210/er.2010-0013</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3365799">3365799</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/21051590">21051590</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Endocr+Rev&rft.atitle=The+molecular+biology%2C+biochemistry%2C+and+physiology+of+human+steroidogenesis+and+its+disorders&rft.volume=32&rft.issue=1&rft.pages=81-151&rft.date=2011-02&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3365799%23id-name%3DPMC&rft_id=info%3Apmid%2F21051590&rft_id=info%3Adoi%2F10.1210%2Fer.2010-0013&rft.aulast=Miller&rft.aufirst=WL&rft.au=Auchus%2C+RJ&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3365799&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span></span> </li> <li id="cite_note-google-pregnan17diol-26"><span class="mw-cite-backlink"><b><a href="#cite_ref-google-pregnan17diol_26-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://scholar.google.com/scholar?&q=%225%CE%B1-pregnan-17%CE%B1-diol-3%2C11%2C20-trione%22">"Google Scholar search results for "5α-pregnan-17α-diol-3,11,20-trione" that is an incorrect name"</a>. 2022. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20231006203706/https://scholar.google.com/scholar?&q=%225%CE%B1-pregnan-17%CE%B1-diol-3%2C11%2C20-trione%22">Archived</a> from the original on 6 October 2023<span class="reference-accessdate">. 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Retrieved <span class="nowrap">1 October</span> 2023</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Google+Scholar+search+results+for+%225%CE%B1-pregnane-17%CE%B1-ol-3%2C20-dione%22+that+is+an+incorrect+name&rft.date=2022&rft_id=https%3A%2F%2Fscholar.google.com%2Fscholar%3Fq%3D%25225%25CE%25B1-pregnane-17%25CE%25B1-ol-3%252C20-dione%2522&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span></span> </li> <li id="cite_note-chemster-28"><span class="mw-cite-backlink"><b><a href="#cite_ref-chemster_28-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMakinTrafford1972" class="citation journal cs1">Makin HL, Trafford DJ (1972). "The chemistry of the steroids". <i>Clinics in Endocrinology and Metabolism</i>. <b>1</b> (2): 333–360. <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%2FS0300-595X%2872%2980024-0">10.1016/S0300-595X(72)80024-0</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Clinics+in+Endocrinology+and+Metabolism&rft.atitle=The+chemistry+of+the+steroids&rft.volume=1&rft.issue=2&rft.pages=333-360&rft.date=1972&rft_id=info%3Adoi%2F10.1016%2FS0300-595X%2872%2980024-0&rft.aulast=Makin&rft.aufirst=HL&rft.au=Trafford%2C+DJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span></span> </li> <li id="cite_note-pmid13167092-29"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid13167092_29-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBongiovanniClayton1954" class="citation journal cs1">Bongiovanni AM, Clayton GW (March 1954). 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title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Molecular+Microbiology&rft.atitle=Steroid+biosynthesis+in+prokaryotes%3A+identification+of+myxobacterial+steroids+and+cloning+of+the+first+bacterial+2%2C3%28S%29-oxidosqualene+cyclase+from+the+myxobacterium+Stigmatella+aurantiaca&rft.volume=47&rft.issue=2&rft.pages=471-81&rft.date=2003-01&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A37959511%23id-name%3DS2CID&rft_id=info%3Apmid%2F12519197&rft_id=info%3Adoi%2F10.1046%2Fj.1365-2958.2003.03309.x&rft.aulast=Bode&rft.aufirst=HB&rft.au=Zeggel%2C+B&rft.au=Silakowski%2C+B&rft.au=Wenzel%2C+SC&rft.au=Reichenbach%2C+H&rft.au=M%C3%BCller%2C+R&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span></span> </li> <li id="cite_note-pmid20333205-43"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid20333205_43-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" 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href="https://pubmed.ncbi.nlm.nih.gov/20333205">20333205</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Genome+Biology+and+Evolution&rft.atitle=Phylogenomics+of+sterol+synthesis%3A+insights+into+the+origin%2C+evolution%2C+and+diversity+of+a+key+eukaryotic+feature&rft.volume=1&rft.pages=364-81&rft.date=2009&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2817430%23id-name%3DPMC&rft_id=info%3Apmid%2F20333205&rft_id=info%3Adoi%2F10.1093%2Fgbe%2Fevp036&rft.aulast=Desmond&rft.aufirst=E&rft.au=Gribaldo%2C+S&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2817430&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span></span> </li> <li id="cite_note-pmid21531832-44"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid21531832_44-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite 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KGaA. <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%2F14356007.a13_089">10.1002/14356007.a13_089</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-527-30673-2" title="Special:BookSources/978-3-527-30673-2"><bdi>978-3-527-30673-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Hormones&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.pub=Wiley-VCH+Verlag+GmbH+%26+Co.+KGaA&rft.date=2000&rft_id=info%3Adoi%2F10.1002%2F14356007.a13_089&rft.isbn=978-3-527-30673-2&rft.aulast=Sandow&rft.aufirst=J&rft.au=J%C3%BCrgen%2C+E&rft.au=Haring%2C+M&rft.au=Neef%2C+G&rft.au=Prezewowsky%2C+K&rft.au=Stache%2C+U&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span></span> </li> <li id="cite_note-Fried-1952-90"><span class="mw-cite-backlink"><b><a href="#cite_ref-Fried-1952_90-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFriedThomaGerkeHerz1952" class="citation journal cs1">Fried J, Thoma RW, Gerke JR, Herz JE, Donin MN, Perlman D (1952). "Microbiological Transformations of Steroids.1 I. Introduction of Oxygen at Carbon-11 of Progesterone". <i>Journal of the American Chemical Society</i>. <b>73</b> (23): 5933–5936. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja01143a033">10.1021/ja01143a033</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+American+Chemical+Society&rft.atitle=Microbiological+Transformations+of+Steroids.1+I.+Introduction+of+Oxygen+at+Carbon-11+of+Progesterone&rft.volume=73&rft.issue=23&rft.pages=5933-5936&rft.date=1952&rft_id=info%3Adoi%2F10.1021%2Fja01143a033&rft.aulast=Fried&rft.aufirst=J&rft.au=Thoma%2C+RW&rft.au=Gerke%2C+JR&rft.au=Herz%2C+JE&rft.au=Donin%2C+MN&rft.au=Perlman%2C+D&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span></span> </li> <li id="cite_note-Capek-1966-91"><span class="mw-cite-backlink"><b><a href="#cite_ref-Capek-1966_91-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCapekOldrichAlois1966" class="citation book cs1">Capek M, Oldrich H, Alois C (1966). <i>Microbial Transformations of Steroids</i>. 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"Sterols. LXXXI. 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The Nobel Foundation. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20121020171424/http://www.nobelprize.org/nobel_prizes/chemistry/laureates/1927/">Archived</a> from the original on 20 October 2012<span class="reference-accessdate">. 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Retrieved <span class="nowrap">1 December</span> 2013</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=The+Nobel+Prize+in+Chemistry+1965&rft.pub=The+Nobel+Foundation&rft_id=http%3A%2F%2Fnobelprize.org%2Fnobel_prizes%2Fchemistry%2Flaureates%2F1965%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span></span> </li> <li id="cite_note-Nobel_Prize_Chemistry_1969-98"><span class="mw-cite-backlink"><b><a href="#cite_ref-Nobel_Prize_Chemistry_1969_98-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://nobelprize.org/nobel_prizes/chemistry/laureates/1969/">"The Nobel Prize in Chemistry 1969"</a>. 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Retrieved <span class="nowrap">1 December</span> 2013</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=The+Nobel+Prize+in+Chemistry+1975&rft.pub=The+Nobel+Foundation&rft_id=http%3A%2F%2Fnobelprize.org%2Fnobel_prizes%2Fchemistry%2Flaureates%2F1975%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="Bibliography">Bibliography</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Steroid&action=edit&section=28" title="Edit section: Bibliography"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239549316">.mw-parser-output .refbegin{margin-bottom:0.5em}.mw-parser-output .refbegin-hanging-indents>ul{margin-left:0}.mw-parser-output .refbegin-hanging-indents>ul>li{margin-left:0;padding-left:3.2em;text-indent:-3.2em}.mw-parser-output .refbegin-hanging-indents ul,.mw-parser-output .refbegin-hanging-indents ul li{list-style:none}@media(max-width:720px){.mw-parser-output .refbegin-hanging-indents>ul>li{padding-left:1.6em;text-indent:-1.6em}}.mw-parser-output .refbegin-columns{margin-top:0.3em}.mw-parser-output .refbegin-columns ul{margin-top:0}.mw-parser-output .refbegin-columns li{page-break-inside:avoid;break-inside:avoid-column}@media screen{.mw-parser-output .refbegin{font-size:90%}}</style><div class="refbegin refbegin-columns references-column-width" style="column-width: 30em"> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRussel2005" class="citation book cs1">Russel CA (2005). "Organic Chemistry: Natural products, Steroids". In Russell CA, Roberts GK (eds.). <i>Chemical History: Reviews of the Recent Literature</i>. Cambridge: RSC Publ. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-85404-464-1" title="Special:BookSources/978-0-85404-464-1"><bdi>978-0-85404-464-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Organic+Chemistry%3A+Natural+products%2C+Steroids&rft.btitle=Chemical+History%3A+Reviews+of+the+Recent+Literature&rft.place=Cambridge&rft.pub=RSC+Publ.&rft.date=2005&rft.isbn=978-0-85404-464-1&rft.aulast=Russel&rft.aufirst=CA&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span></li> <li><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.acs.org/content/acs/en/education/whatischemistry/landmarks/progesteronesynthesis.html">"Russell Marker Creation of the Mexican Steroid Hormone Industry - Landmark -"</a>. American Chemical Society. 1999. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200212065359/https://www.acs.org/content/acs/en/education/whatischemistry/landmarks/progesteronesynthesis.html">Archived</a> from the original on 12 February 2020<span class="reference-accessdate">. Retrieved <span class="nowrap">10 May</span> 2014</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Russell+Marker+Creation+of+the+Mexican+Steroid+Hormone+Industry+-+Landmark+-&rft.pub=American+Chemical+Society&rft.date=1999&rft_id=https%3A%2F%2Fwww.acs.org%2Fcontent%2Facs%2Fen%2Feducation%2Fwhatischemistry%2Flandmarks%2Fprogesteronesynthesis.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLednicer2011" class="citation book cs1">Lednicer D (2011). <i>Steroid Chemistry at a Glance</i>. Hoboken: Wiley. <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%2F9780470973639">10.1002/9780470973639</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-470-66085-0" title="Special:BookSources/978-0-470-66085-0"><bdi>978-0-470-66085-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Steroid+Chemistry+at+a+Glance&rft.place=Hoboken&rft.pub=Wiley&rft.date=2011&rft_id=info%3Adoi%2F10.1002%2F9780470973639&rft.isbn=978-0-470-66085-0&rft.aulast=Lednicer&rft.aufirst=D&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span> A concise history of the study of steroids.</li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFYoderJohnston2005" class="citation journal cs1">Yoder RA, Johnston JN (December 2005). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2575671">"A case study in biomimetic total synthesis: polyolefin carbocyclizations to terpenes and steroids"</a>. <i>Chemical Reviews</i>. <b>105</b> (12): 4730–56. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fcr040623l">10.1021/cr040623l</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2575671">2575671</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16351060">16351060</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+Reviews&rft.atitle=A+case+study+in+biomimetic+total+synthesis%3A+polyolefin+carbocyclizations+to+terpenes+and+steroids&rft.volume=105&rft.issue=12&rft.pages=4730-56&rft.date=2005-12&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2575671%23id-name%3DPMC&rft_id=info%3Apmid%2F16351060&rft_id=info%3Adoi%2F10.1021%2Fcr040623l&rft.aulast=Yoder&rft.aufirst=RA&rft.au=Johnston%2C+JN&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2575671&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span> A review of the history of steroid synthesis, especially <a href="/wiki/Biomimetic" class="mw-redirect" title="Biomimetic">biomimetic</a>.</li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHanWalkerArltRoss2014" class="citation journal cs1">Han TS, Walker BR, Arlt W, Ross RJ (February 2014). "Treatment and health outcomes in adults with congenital adrenal hyperplasia". <i>Nature Reviews. Endocrinology</i>. <b>10</b> (2): 115–24. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fnrendo.2013.239">10.1038/nrendo.2013.239</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/24342885">24342885</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:6090764">6090764</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nature+Reviews.+Endocrinology&rft.atitle=Treatment+and+health+outcomes+in+adults+with+congenital+adrenal+hyperplasia&rft.volume=10&rft.issue=2&rft.pages=115-24&rft.date=2014-02&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A6090764%23id-name%3DS2CID&rft_id=info%3Apmid%2F24342885&rft_id=info%3Adoi%2F10.1038%2Fnrendo.2013.239&rft.aulast=Han&rft.aufirst=TS&rft.au=Walker%2C+BR&rft.au=Arlt%2C+W&rft.au=Ross%2C+RJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span> Adrenal steroidogenesis pathway.</li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGreep2013" class="citation book cs1">Greep RO, ed. (22 October 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=eXXAAgAAQBAJ">"Cortoic acids"</a>. <i>Recent Progress in Hormone Research: Proceedings of the 1979 Laurentian Hormone Conference</i>. <a href="/wiki/Elsevier_Science" class="mw-redirect" title="Elsevier Science">Elsevier Science</a>. pp. 345–391. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4832-1956-1" title="Special:BookSources/978-1-4832-1956-1"><bdi>978-1-4832-1956-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Cortoic+acids&rft.btitle=Recent+Progress+in+Hormone+Research%3A+Proceedings+of+the+1979+Laurentian+Hormone+Conference&rft.pages=345-391&rft.pub=Elsevier+Science&rft.date=2013-10-22&rft.isbn=978-1-4832-1956-1&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DeXXAAgAAQBAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBowen2001" class="citation web cs1">Bowen RA (20 October 2001). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20090228213018/http://arbl.cvmbs.colostate.edu/hbooks/pathphys/endocrine/basics/steroidogenesis.html">"Steroidogenesis"</a>. <i>Pathophysiology of the Endocrine System</i>. Colorado State University. Archived from <a rel="nofollow" class="external text" href="http://arbl.cvmbs.colostate.edu/hbooks/pathphys/endocrine/basics/steroidogenesis.html">the original</a> on 28 February 2009.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Pathophysiology+of+the+Endocrine+System&rft.atitle=Steroidogenesis&rft.date=2001-10-20&rft.aulast=Bowen&rft.aufirst=RA&rft_id=http%3A%2F%2Farbl.cvmbs.colostate.edu%2Fhbooks%2Fpathphys%2Fendocrine%2Fbasics%2Fsteroidogenesis.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASteroid" class="Z3988"></span></li></ul> </div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1236075235">.mw-parser-output .navbox{box-sizing:border-box;border:1px solid #a2a9b1;width:100%;clear:both;font-size:88%;text-align:center;padding:1px;margin:1em auto 0}.mw-parser-output .navbox 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.navbox-group,.mw-parser-output .navbox-subgroup .navbox-title{background-color:#ddf}.mw-parser-output .navbox-subgroup .navbox-group,.mw-parser-output .navbox-subgroup .navbox-abovebelow{background-color:#e6e6ff}.mw-parser-output .navbox-even{background-color:#f7f7f7}.mw-parser-output .navbox-odd{background-color:transparent}.mw-parser-output .navbox .hlist td dl,.mw-parser-output .navbox .hlist td ol,.mw-parser-output .navbox .hlist td ul,.mw-parser-output .navbox td.hlist dl,.mw-parser-output .navbox td.hlist ol,.mw-parser-output .navbox td.hlist ul{padding:0.125em 0}.mw-parser-output .navbox .navbar{display:block;font-size:100%}.mw-parser-output .navbox-title .navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style></div><div role="navigation" class="navbox" aria-labelledby="Steroid_classification" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Steroid_classification" title="Template:Steroid classification"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Steroid_classification" title="Template talk:Steroid classification"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Steroid_classification" title="Special:EditPage/Template:Steroid classification"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Steroid_classification" style="font-size:114%;margin:0 4em"><a class="mw-selflink selflink">Steroid</a> classification</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">C<sub>17</sub></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/Gonane" title="Gonane">Gonane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">C<sub>18</sub></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/Estrane" title="Estrane">Estrane</a>: <i>Dehydrogenated:</i> <a href="/wiki/Estrene" class="mw-redirect" title="Estrene">Estrene</a></li> <li><a href="/w/index.php?title=Estradiene&action=edit&redlink=1" class="new" title="Estradiene (page does not exist)">Estradiene</a></li> <li><a href="/wiki/Estratriene" class="mw-redirect" title="Estratriene">Estratriene</a>; <i>Substituted:</i> <a href="/wiki/Estratrienolone" class="mw-redirect" title="Estratrienolone">Estratrienolone</a></li> <li><a href="/wiki/Estratrienediol" class="mw-redirect" title="Estratrienediol">Estratrienediol</a></li> <li><a href="/wiki/Estratrienetriol" class="mw-redirect" title="Estratrienetriol">Estratrienetriol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">C<sub>19</sub></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/Androstane" title="Androstane">Androstane</a>: <i>Dehydrogenated:</i> <a href="/wiki/Androstene" class="mw-redirect" title="Androstene">Androstene</a></li> <li><a href="/wiki/Androstadiene" class="mw-redirect" title="Androstadiene">Androstadiene</a></li> <li><a href="/w/index.php?title=Androstatriene&action=edit&redlink=1" class="new" title="Androstatriene (page does not exist)">Androstatriene</a>; <i>Substituted:</i> <a href="/w/index.php?title=Androstanol&action=edit&redlink=1" class="new" title="Androstanol (page does not exist)">Androstanol</a></li> <li><a href="/wiki/Androstenol" title="Androstenol">Androstenol</a></li> <li><a href="/w/index.php?title=Androstanone&action=edit&redlink=1" class="new" title="Androstanone (page does not exist)">Androstanone</a></li> <li><a href="/wiki/Androstenone" title="Androstenone">Androstenone</a></li> <li><a href="/wiki/Androstanediol" title="Androstanediol">Androstanediol</a></li> <li><a href="/wiki/Androstenediol" title="Androstenediol">Androstenediol</a></li> <li><a href="/wiki/Androstanedione" title="Androstanedione">Androstanedione</a></li> <li><a href="/wiki/Androstenedione" title="Androstenedione">Androstenedione</a></li> <li><a href="/wiki/Androstenetrione" class="mw-redirect" title="Androstenetrione">Androstenetrione</a></li> <li><a href="/wiki/Androstanolone" title="Androstanolone">Androstanolone</a></li> <li><a href="/wiki/Androstenolone" title="Androstenolone">Androstenolone</a></li> <li><a href="/wiki/Androstadienol" title="Androstadienol">Androstadienol</a></li> <li><a href="/wiki/Androstadienone" title="Androstadienone">Androstadienone</a>; <a href="/wiki/Etiocholane" title="Etiocholane">Etiocholane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">C<sub>20</sub></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/19-Norpregnane" title="19-Norpregnane">19-Norpregnane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">C<sub>21</sub></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/Pregnane" title="Pregnane">Pregnane</a>: <i>Dehydrogenated:</i> <a href="/wiki/Pregnene" title="Pregnene">Pregnene</a></li> <li><a href="/wiki/Pregnadiene" title="Pregnadiene">Pregnadiene</a></li> <li><a href="/wiki/Pregnatriene" title="Pregnatriene">Pregnatriene</a>; <i>Substituted:</i> <a href="/wiki/Pregnanediol" title="Pregnanediol">Pregnanediol</a></li> <li><a href="/wiki/Pregnanetriol" title="Pregnanetriol">Pregnanetriol</a></li> <li><a href="/w/index.php?title=Pregnenediol&action=edit&redlink=1" class="new" title="Pregnenediol (page does not exist)">Pregnenediol</a></li> <li><a href="/wiki/Pregnanedione" title="Pregnanedione">Pregnanedione</a></li> <li><a href="/wiki/Pregnenedione" title="Pregnenedione">Pregnenedione</a></li> <li><a href="/wiki/5%CE%B1-Pregnane" class="mw-redirect" title="5α-Pregnane">5α-Pregnane</a></li> <li><a href="/wiki/5%CE%B2-Pregnane" title="5β-Pregnane">5β-Pregnane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">C<sub>23</sub></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/Cardanolide" title="Cardanolide">Cardanolide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">C<sub>24</sub></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/Cholane" title="Cholane">Cholane</a></li> <li><a href="/wiki/Bile_acid" title="Bile acid">Bile acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">C<sub>27</sub></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/Cholestane" title="Cholestane">Cholestane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Functional_group" title="Functional group">Functional group</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/17-Ketosteroid" class="mw-redirect" title="17-Ketosteroid">17-Ketosteroid</a></li> <li><a href="/wiki/Hydroxysteroid" title="Hydroxysteroid">Hydroxysteroid</a></li> <li><a href="/wiki/Halogenation" title="Halogenation">Halogenated steroid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Elements removed</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/Norsteroid" title="Norsteroid">Norsteroid</a></li> <li><a href="/wiki/Secosteroid" title="Secosteroid">Secosteroid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Elements replaced</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/Azasteroid" title="Azasteroid">Azasteroid</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Types_of_terpenes_and_terpenoids_(#_of_isoprene_units)" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Terpenoids" title="Template:Terpenoids"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Terpenoids" title="Template talk:Terpenoids"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Terpenoids" title="Special:EditPage/Template:Terpenoids"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Types_of_terpenes_and_terpenoids_(#_of_isoprene_units)" style="font-size:114%;margin:0 4em">Types of <a href="/wiki/Terpene" title="Terpene">terpenes</a> and <a href="/wiki/Terpenoid" title="Terpenoid">terpenoids</a> (# of <a href="/wiki/Isoprene" title="Isoprene">isoprene</a> units)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Basic forms:</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>Acyclic (linear, <i>cis</i> and <i>trans</i> forms)</li> <li>Monocyclic (single ring)</li> <li>Bicyclic (2 rings)</li> <li><a href="/wiki/Iridoid" title="Iridoid">Iridoids</a> (cyclopentane ring)</li> <li>Iridoid glycosides (iridoids bound to a sugar)</li> <li><a class="mw-selflink selflink">Steroids</a> (4 rings)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hemiterpenoid" class="mw-redirect" title="Hemiterpenoid">Hemiterpenoids</a> (1)</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/Isoprene" title="Isoprene">Isoprene</a> (C<sub>5</sub>H<sub>8</sub>)</li> <li><a href="/wiki/Prenol" title="Prenol">Prenol</a></li> <li><a href="/wiki/Isovaleric_acid" title="Isovaleric acid">Isovaleric acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Monoterpene" title="Monoterpene">Monoterpenes</a> <br />(C<sub>10</sub>H<sub>16</sub>)(2)</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%">Acyclic</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/Ocimene" title="Ocimene">Ocimene</a></li> <li><a href="/wiki/Myrcene" title="Myrcene">Myrcenes</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Monocyclic</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/Limonene" title="Limonene">Limonene</a></li> <li><a href="/wiki/Terpinene" title="Terpinene">Terpinene</a></li> <li><a href="/wiki/Phellandrene" title="Phellandrene">Phellandrene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Bicyclic</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/Pinene" title="Pinene">Pinene</a> (<a href="/wiki/Alpha-Pinene" class="mw-redirect" title="Alpha-Pinene">α</a> and <a href="/wiki/Beta-Pinene" class="mw-redirect" title="Beta-Pinene">β</a>)</li> <li><a href="/wiki/Camphene" title="Camphene">Camphene</a></li> <li><a href="/wiki/Thujene" title="Thujene">Thujene</a></li> <li><a href="/wiki/Sabinene" title="Sabinene">Sabinene</a></li> <li><a href="/wiki/Carene" class="mw-redirect" title="Carene">Carene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Monoterpenoids <br />(2,modified)</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%">Acyclic</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/Citronellal" title="Citronellal">Citronellal</a></li> <li><a href="/wiki/Citral" title="Citral">Citral</a></li> <li><a href="/wiki/Citronellol" title="Citronellol">Citronellol</a></li> <li><a href="/wiki/Geraniol" title="Geraniol">Geraniol</a></li> <li><a href="/wiki/Geranyl_pyrophosphate" title="Geranyl pyrophosphate">Geranyl pyrophosphate</a></li> <li><a href="/wiki/Halomon" title="Halomon">Halomon</a></li> <li><a href="/wiki/Linalool" title="Linalool">Linalool</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Monocyclic</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/Grapefruit_mercaptan" title="Grapefruit mercaptan">Grapefruit mercaptan</a></li> <li><a href="/wiki/Menthol" title="Menthol">Menthol</a></li> <li><a href="/wiki/P-Cymene" title="P-Cymene">p-Cymene</a></li> <li><a href="/wiki/Thujaplicin" title="Thujaplicin">Thujaplicins</a> (<a href="/wiki/Hinokitiol" title="Hinokitiol">Hinokitiol</a>)</li> <li><a href="/wiki/Thymol" title="Thymol">Thymol</a></li> <li><a href="/wiki/Perillyl_alcohol" title="Perillyl alcohol">Perillyl alcohol</a></li> <li><a href="/wiki/Carvacrol" title="Carvacrol">Carvacrol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Bicyclic</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/Camphor" title="Camphor">Camphor</a></li> <li><a href="/wiki/Borneol" title="Borneol">Borneol</a></li> <li><a href="/wiki/Bornyl_acetate" title="Bornyl acetate">Bornyl acetate</a></li> <li><a href="/wiki/Eucalyptol" title="Eucalyptol">Eucalyptol</a></li> <li><a href="/wiki/Ascaridole" title="Ascaridole">Ascaridole</a></li> <li><a href="/wiki/Umbellulone" title="Umbellulone">Umbellulone</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/Sesquiterpenoids" class="mw-redirect" title="Sesquiterpenoids">Sesquiterpenoids</a> (3)</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/Artemisinin" title="Artemisinin">Artemisinin</a></li> <li><a href="/wiki/Bisabolol" title="Bisabolol">Bisabolol</a></li> <li><a href="/wiki/Cadinene" class="mw-redirect" title="Cadinene">Cadinene</a></li> <li><a href="/wiki/Cadinol" title="Cadinol">Cadinol</a></li> <li><a href="/wiki/Cedrene" title="Cedrene">Cedrene</a></li> <li>Chanootin</li> <li><a href="/wiki/Farnesyl_pyrophosphate" title="Farnesyl pyrophosphate">Farnesyl pyrophosphate</a></li> <li>Juniperol</li> <li><a href="/wiki/Longifolene" title="Longifolene">Longifolene</a></li> <li>Muurolene</li> <li>Nootkatin</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Terpenoid" title="Terpenoid">Diterpenoids</a> (4)</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%">Acyclic</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/Phytol" title="Phytol">Phytol</a></li> <li><a href="/wiki/Geranylgeranyl_pyrophosphate" title="Geranylgeranyl pyrophosphate">Geranylgeranyl pyrophosphate</a></li> <li>Geranyl-linalool</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Monocyclic</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/Retinol" title="Retinol">Retinol</a></li> <li><a href="/wiki/Retinal" title="Retinal">Retinal</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Bicyclic</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>cis</i>-Abienol</li> <li>Epimanool</li> <li><a href="/wiki/Salvinorin_A" title="Salvinorin A">Salvinorin A</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Tricyclic</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/Cembrene" class="mw-redirect" title="Cembrene">Cembrene</a></li> <li><a href="/wiki/Forskolin" title="Forskolin">Forskolin</a></li> <li>Manoyl oxide</li> <li>Pimaral</li> <li>Pimarol</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Tetracyclic</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/Aphidicolin" title="Aphidicolin">Aphidicolin</a></li> <li><a href="/wiki/Gibberellin" title="Gibberellin">Gibberellin</a></li> <li><a href="/wiki/Paclitaxel" title="Paclitaxel">Paclitaxel</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Resin_acid" title="Resin acid">Resin acids</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/Abietic_acid" title="Abietic acid">Abietic acid</a></li> <li>Communic acid</li> <li>Dehydroabietic acid</li> <li><a href="/wiki/Isopimaric_acid" title="Isopimaric acid">Isopimaric acid</a></li> <li>Lambertianic acid</li> <li><a href="/wiki/Levopimaric_acid" title="Levopimaric acid">Levopimaric acid</a></li> <li>Mercusic acid</li> <li>Neoabietic acid</li> <li><a href="/wiki/Pimaric_acid" title="Pimaric acid">Pimaric acid</a></li> <li>Sandaracopimaric acid</li> <li>Secodehydroabietic acid</li> <li>Palustric acid</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sesterterpenoid" class="mw-redirect" title="Sesterterpenoid">Sesterterpenoids</a> (5)</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>Geranylfarnesol</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Triterpenoid" class="mw-redirect" title="Triterpenoid">Triterpenoids</a> (6)</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 class="mw-selflink selflink">Steroids</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/Phytosterol" title="Phytosterol">Phytosterols</a> <ul><li><a href="/wiki/Campesterol" title="Campesterol">Campesterol</a></li> <li>Citrostadienol</li> <li><a href="/wiki/Cycloartenol" title="Cycloartenol">Cycloartenol</a></li> <li><a href="/wiki/Sitostanol" class="mw-redirect" title="Sitostanol">Sitostanol</a></li> <li><a href="/wiki/Sitosterol" class="mw-redirect" title="Sitosterol">Sitosterol</a></li> <li><a href="/wiki/Stigmasterol" title="Stigmasterol">Stigmasterol</a></li></ul></li> <li><a href="/wiki/Tocopherol" title="Tocopherol">Tocopherols</a></li> <li><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></li> <li><a href="/wiki/Testosterone" title="Testosterone">Testosterone</a></li> <li><a href="/wiki/Cholecalciferol" title="Cholecalciferol">Cholecalciferol</a></li> <li><a href="/wiki/Ecdysone" title="Ecdysone">Ecdysones</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Betulin" title="Betulin">Betulin</a></li> <li><a href="/wiki/Lanosterol" title="Lanosterol">Lanosterol</a></li> <li><a href="/wiki/Saponin" title="Saponin">Saponins</a></li> <li>Serratenediol</li> <li><a href="/wiki/Squalane" title="Squalane">Squalane</a></li> <li>Acids <ul><li><a href="/wiki/Oleanolic_acid" title="Oleanolic acid">Oleanolic acid</a></li> <li><a href="/wiki/Ursolic_acid" title="Ursolic acid">Ursolic acid</a></li> <li><a href="/wiki/Betulinic_acid" title="Betulinic acid">Betulinic acid</a></li> <li><a href="/wiki/Moronic_acid" title="Moronic acid">Moronic acid</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Sesquarterpenes/oids (7)</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>Ferrugicadiol</li> <li>Tetraprenylcurcumene</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tetraterpenoid" class="mw-redirect" title="Tetraterpenoid">Tetraterpenoids</a><br />(<a href="/wiki/Carotenoid" title="Carotenoid">Carotenoids</a>) (8)</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/Carotene" title="Carotene">Carotenes</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/Alpha-Carotene" class="mw-redirect" title="Alpha-Carotene">Alpha-Carotene</a></li> <li><a href="/wiki/Beta-Carotene" class="mw-redirect" title="Beta-Carotene">Beta-Carotene</a></li> <li><a href="/wiki/Gamma-Carotene" class="mw-redirect" title="Gamma-Carotene">Gamma-Carotene</a></li> <li><a href="/wiki/Delta-Carotene" class="mw-redirect" title="Delta-Carotene">Delta-Carotene</a></li> <li><a href="/wiki/Lycopene" title="Lycopene">Lycopene</a></li> <li><a href="/wiki/Neurosporene" title="Neurosporene">Neurosporene</a></li> <li><a href="/wiki/Phytofluene" title="Phytofluene">Phytofluene</a></li> <li><a href="/wiki/Phytoene" title="Phytoene">Phytoene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Xanthophyll" title="Xanthophyll">Xanthophylls</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/Canthaxanthin" title="Canthaxanthin">Canthaxanthin</a></li> <li><a href="/wiki/Cryptoxanthin" class="mw-redirect" title="Cryptoxanthin">Cryptoxanthin</a></li> <li><a href="/wiki/Zeaxanthin" title="Zeaxanthin">Zeaxanthin</a></li> <li><a href="/wiki/Astaxanthin" title="Astaxanthin">Astaxanthin</a></li> <li><a href="/wiki/Lutein" title="Lutein">Lutein</a></li> <li><a href="/wiki/Rubixanthin" title="Rubixanthin">Rubixanthin</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/Polyterpenoid" class="mw-redirect" title="Polyterpenoid">Polyterpenoids</a> (many)</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/Natural_rubber" title="Natural rubber">Natural rubber</a></li> <li><a href="/wiki/Gutta_percha" class="mw-redirect" title="Gutta percha">Gutta percha</a></li> <li>Gutta-balatá</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Norisoprenoids (modified)</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>3-oxo-α-ionol</li> <li>7,8-dihydroionone</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Synthesis</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>Terpene synthase enzymes (many), having in common a <a href="/wiki/Terpene_synthase_N_terminal_domain" title="Terpene synthase N terminal domain">terpene synthase N terminal domain</a> (<a href="/wiki/Protein_domain" title="Protein domain">protein domain</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Activated isoprene forms</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/Isopentenyl_pyrophosphate" title="Isopentenyl pyrophosphate">Isopentenyl pyrophosphate</a> (IPP)</li> <li><a href="/wiki/Dimethylallyl_pyrophosphate" title="Dimethylallyl pyrophosphate">Dimethylallyl pyrophosphate</a> (DMAPP)</li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Cholesterol_and_steroid_metabolic_intermediates" 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:Cholesterol_and_steroid_intermediates" title="Template:Cholesterol and steroid intermediates"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Cholesterol_and_steroid_intermediates" title="Template talk:Cholesterol and steroid intermediates"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Cholesterol_and_steroid_intermediates" title="Special:EditPage/Template:Cholesterol and steroid intermediates"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Cholesterol_and_steroid_metabolic_intermediates" style="font-size:114%;margin:0 4em"><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a> and <a class="mw-selflink selflink">steroid</a> <a href="/wiki/Metabolic_intermediate" title="Metabolic intermediate">metabolic intermediates</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Mevalonate_pathway" title="Mevalonate pathway">Mevalonate pathway</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%">to <a href="/wiki/HMG-CoA" title="HMG-CoA">HMG-CoA</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">Acetyl-CoA</a></li> <li><a href="/wiki/Acetoacetyl-CoA" title="Acetoacetyl-CoA">Acetoacetyl-CoA</a></li> <li><a href="/wiki/Beta-Hydroxy_beta-methylbutyric_acid" class="mw-redirect" title="Beta-Hydroxy beta-methylbutyric acid">HMB</a></li> <li><a href="/wiki/Beta-Hydroxy_beta-methylbutyryl-CoA" class="mw-redirect" title="Beta-Hydroxy beta-methylbutyryl-CoA">HMB-CoA</a></li> <li><a href="/wiki/HMG-CoA" title="HMG-CoA">HMG-CoA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ketone_bodies" title="Ketone bodies">Ketone bodies</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/Acetone" title="Acetone">Acetone</a></li> <li><a href="/wiki/Acetoacetic_acid" title="Acetoacetic acid">Acetoacetic acid</a></li> <li><a href="/wiki/Beta-Hydroxybutyric_acid" class="mw-redirect" title="Beta-Hydroxybutyric acid">β-Hydroxybutyric acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">to <a href="/wiki/Dimethylallyl_pyrophosphate" title="Dimethylallyl pyrophosphate">DMAPP</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/Mevalonic_acid" title="Mevalonic acid">Mevalonic acid</a></li> <li><a href="/wiki/Phosphomevalonic_acid" title="Phosphomevalonic acid">Phosphomevalonic acid</a></li> <li><a href="/wiki/5-Diphosphomevalonic_acid" title="5-Diphosphomevalonic acid">5-Diphosphomevalonic acid</a></li> <li><a href="/wiki/Isopentenyl_pyrophosphate" title="Isopentenyl pyrophosphate">Isopentenyl pyrophosphate</a></li> <li><a href="/wiki/Dimethylallyl_pyrophosphate" title="Dimethylallyl pyrophosphate">Dimethylallyl pyrophosphate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Geranyl-</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/Geranyl_pyrophosphate" title="Geranyl pyrophosphate">Geranyl pyrophosphate</a></li> <li><a href="/wiki/Geranylgeranyl_pyrophosphate" title="Geranylgeranyl pyrophosphate">Geranylgeranyl pyrophosphate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carotenoid" title="Carotenoid">Carotenoid</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/Prephytoene_diphosphate" title="Prephytoene diphosphate">Prephytoene diphosphate</a></li> <li><a href="/wiki/Phytoene" title="Phytoene">Phytoene</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/Non-mevalonate_pathway" title="Non-mevalonate pathway">Non-mevalonate pathway</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><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1-Deoxy-D-xylulose_5-phosphate" title="1-Deoxy-D-xylulose 5-phosphate">DOXP</a></li> <li><a href="/wiki/2-C-methylerythritol_4-phosphate" class="mw-redirect" title="2-C-methylerythritol 4-phosphate">MEP</a></li> <li><a href="/wiki/4-diphosphocytidyl-2-C-methylerythritol" class="mw-redirect" title="4-diphosphocytidyl-2-C-methylerythritol">CDP-ME</a></li> <li><a href="/wiki/4-diphosphocytidyl-2-C-methyl-D-erythritol_2-phosphate" class="mw-redirect" title="4-diphosphocytidyl-2-C-methyl-D-erythritol 2-phosphate">CDP-MEP</a></li> <li><a href="/wiki/2-C-methyl-D-erythritol_2,4-cyclopyrophosphate" class="mw-redirect" title="2-C-methyl-D-erythritol 2,4-cyclopyrophosphate">MEcPP</a></li> <li><a href="/wiki/(E)-4-Hydroxy-3-methyl-but-2-enyl_pyrophosphate" title="(E)-4-Hydroxy-3-methyl-but-2-enyl pyrophosphate">HMB-PP</a></li> <li><a href="/wiki/Isopentenyl_pyrophosphate" title="Isopentenyl pyrophosphate">IPP</a></li> <li><a href="/wiki/Dimethylallyl_pyrophosphate" title="Dimethylallyl pyrophosphate">DMAPP</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">To <a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</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/Farnesyl_pyrophosphate" title="Farnesyl pyrophosphate">Farnesyl pyrophosphate</a></li> <li><a href="/wiki/Squalene" title="Squalene">Squalene</a></li> <li><a href="/wiki/2,3-Oxidosqualene" title="2,3-Oxidosqualene">2,3-Oxidosqualene</a></li> <li><a href="/wiki/Lanosterol" title="Lanosterol">Lanosterol</a></li></ul> <ul><li><a href="/wiki/Lanosterol" title="Lanosterol">Lanosterol</a></li> <li><a href="/w/index.php?title=14-demethyllanosterol&action=edit&redlink=1" class="new" title="14-demethyllanosterol (page does not exist)">14-demethyllanosterol</a></li> <li><a href="/w/index.php?title=4alpha-Methylzymosterol&action=edit&redlink=1" class="new" title="4alpha-Methylzymosterol (page does not exist)">4alpha-Methylzymosterol</a></li> <li><a href="/w/index.php?title=Zymosterone&action=edit&redlink=1" class="new" title="Zymosterone (page does not exist)">Zymosterone</a></li> <li><a href="/wiki/Zymosterol" title="Zymosterol">Zymosterol</a></li></ul> <ul><li><a href="/wiki/Zymosterol" title="Zymosterol">Zymosterol</a></li> <li><a href="/w/index.php?title=Zymostenol&action=edit&redlink=1" class="new" title="Zymostenol (page does not exist)">Zymostenol</a></li> <li><a href="/wiki/Lathosterol" title="Lathosterol">Lathosterol</a></li> <li><a href="/wiki/7-Dehydrocholesterol" title="7-Dehydrocholesterol">7-Dehydrocholesterol</a></li> <li><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></li></ul> <ul><li><a href="/wiki/Zymosterol" title="Zymosterol">Zymosterol</a></li> <li><a href="/w/index.php?title=Cholesta-7,24-dien-3-ol&action=edit&redlink=1" class="new" title="Cholesta-7,24-dien-3-ol (page does not exist)">Cholesta-7,24-dien-3-ol</a></li> <li><a href="/wiki/7-Dehydrodesmosterol" title="7-Dehydrodesmosterol">7-Dehydrodesmosterol</a></li> <li><a href="/wiki/Desmosterol" title="Desmosterol">Desmosterol</a></li> <li><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">From <a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a> <br />to <a class="mw-selflink selflink">Steroid hormones</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/22R-Hydroxycholesterol" title="22R-Hydroxycholesterol">22<i>R</i>-Hydroxycholesterol</a></li> <li><a href="/wiki/20%CE%B1,22R-Dihydroxycholesterol" title="20α,22R-Dihydroxycholesterol">20α,22<i>R</i>-Dihydroxycholesterol</a></li> <li>See <a href="/wiki/Template:Steroid_hormones" title="Template:Steroid hormones">here</a> instead.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Nonhuman</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%">To <a href="/wiki/Sitosterol" class="mw-redirect" title="Sitosterol">Sitosterol</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/Cycloartenol" title="Cycloartenol">Cycloartenol</a></li> <li><a href="/w/index.php?title=Cycloeucalenol&action=edit&redlink=1" class="new" title="Cycloeucalenol (page does not exist)">Cycloeucalenol</a></li> <li><a href="/wiki/Obtusifoliol" title="Obtusifoliol">Obtusifoliol</a></li> <li><a href="/wiki/4%CE%B1-methylfecosterol" class="mw-redirect" title="4α-methylfecosterol">4α-methylfecosterol</a></li> <li><a href="/wiki/Isofucosterol" title="Isofucosterol">Isofucosterol</a></li> <li><a href="/wiki/24-Methylenelophenol" title="24-Methylenelophenol">24-Methylenelophenol</a></li> <li><a href="/wiki/Sitosterol" class="mw-redirect" title="Sitosterol">Sitosterol</a></li> <li>More <a href="/wiki/Phytosterol" title="Phytosterol">Phytosterols</a> see <a href="/wiki/Template:Steroid_hormones" title="Template:Steroid hormones">here</a> instead.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">To <a href="/wiki/Ergocalciferol" title="Ergocalciferol">Ergocalciferol</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/Fecosterol" title="Fecosterol">Fecosterol</a></li> <li><a href="/wiki/Episterol" title="Episterol">Episterol</a></li> <li><a href="/wiki/Ergostatrienol" class="mw-redirect" title="Ergostatrienol">Ergostatrienol</a></li> <li><a href="/w/index.php?title=Ergostatetraenol&action=edit&redlink=1" class="new" title="Ergostatetraenol (page does not exist)">Ergostatetraenol</a></li> <li><a href="/wiki/Ergosterol" title="Ergosterol">Ergosterol</a></li> <li><a href="/wiki/Ergocalciferol" title="Ergocalciferol">Ergocalciferol</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Endogenous_steroids" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Steroid_hormones" title="Template:Steroid hormones"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Steroid_hormones" title="Template talk:Steroid hormones"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Steroid_hormones" title="Special:EditPage/Template:Steroid hormones"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Endogenous_steroids" style="font-size:114%;margin:0 4em"><a href="/wiki/Endogenous" class="mw-redirect" title="Endogenous">Endogenous</a> <a class="mw-selflink selflink">steroids</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">Precursors</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></li> <li><a href="/wiki/22R-Hydroxycholesterol" title="22R-Hydroxycholesterol">22<i>R</i>-Hydroxycholesterol</a></li> <li><a href="/wiki/20%CE%B1,22R-Dihydroxycholesterol" title="20α,22R-Dihydroxycholesterol">20α,22<i>R</i>-Dihydroxycholesterol</a></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a></li> <li><a href="/w/index.php?title=11%CE%B2-Hydroxypregnenolone&action=edit&redlink=1" class="new" title="11β-Hydroxypregnenolone (page does not exist)">11β-Hydroxypregnenolone</a></li> <li><a href="/wiki/17%CE%B1-Hydroxypregnenolone" title="17α-Hydroxypregnenolone">17α-Hydroxypregnenolone</a></li> <li><a href="/wiki/21-Hydroxypregnenolone" title="21-Hydroxypregnenolone">21-Hydroxypregnenolone</a></li> <li><a href="/w/index.php?title=17%CE%B1,21-Dihydroxypregnenolone&action=edit&redlink=1" class="new" title="17α,21-Dihydroxypregnenolone (page does not exist)">17α,21-Dihydroxypregnenolone</a></li> <li><a href="/w/index.php?title=11%CE%B2,17%CE%B1,21-Trihydroxypregnenolone&action=edit&redlink=1" class="new" title="11β,17α,21-Trihydroxypregnenolone (page does not exist)">11β,17α,21-Trihydroxypregnenolone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Corticosteroid" title="Corticosteroid">Corticosteroids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Glucocorticoid" title="Glucocorticoid">Glucocorticoids</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Tetrahydrocorticosterone" title="Tetrahydrocorticosterone">3α,5α-Tetrahydrocorticosterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydrocorticosterone" title="5α-Dihydrocorticosterone">5α-Dihydrocorticosterone</a></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone</a></li> <li><a href="/wiki/11-Deoxycortisol" title="11-Deoxycortisol">11-Deoxycortisol</a></li> <li><a href="/wiki/11-Ketoprogesterone" title="11-Ketoprogesterone">11-Ketoprogesterone</a></li> <li><a href="/wiki/21-Deoxycortisol" title="21-Deoxycortisol">21-Deoxycortisol</a></li> <li><a href="/wiki/21-Deoxycortisone" title="21-Deoxycortisone">21-Deoxycortisone</a></li> <li><a href="/wiki/Corticosterone" title="Corticosterone">Corticosterone</a></li> <li><a href="/wiki/Cortisol" title="Cortisol">Cortisol</a></li> <li><a href="/wiki/Cortisone" title="Cortisone">Cortisone</a></li> <li><a href="/wiki/17%CE%B1-Hydroxypregnenolone" title="17α-Hydroxypregnenolone">17α-Hydroxypregnenolone</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone</a></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li></ul> <ul><li><i>Metabolites:</i> <a href="/wiki/5%CE%B1-Dihydrocortisol" title="5α-Dihydrocortisol">5α-Dihydrocortisol</a></li> <li><a href="/w/index.php?title=3%CE%B1,5%CE%B1-Tetrahydrocortisol&action=edit&redlink=1" class="new" title="3α,5α-Tetrahydrocortisol (page does not exist)">3α,5α-Tetrahydrocortisol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Mineralocorticoid" title="Mineralocorticoid">Mineralocorticoids</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/5%CE%B1-Dihydroaldosterone" title="5α-Dihydroaldosterone">5α-Dihydroaldosterone</a></li> <li><a href="/wiki/11-Dehydrocorticosterone" title="11-Dehydrocorticosterone">11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone)</a></li> <li><a href="/wiki/11-Deoxycortisol" title="11-Deoxycortisol">11-Deoxycortisol</a></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone</a></li> <li><a href="/wiki/11%CE%B2-Hydroxyprogesterone" title="11β-Hydroxyprogesterone">11β-Hydroxyprogesterone (21-deoxycorticosterone)</a></li> <li><a href="/wiki/18-Hydroxy-11-deoxycorticosterone" title="18-Hydroxy-11-deoxycorticosterone">18-Hydroxy-11-deoxycorticosterone</a></li> <li><a href="/wiki/18-Hydroxycorticosterone" title="18-Hydroxycorticosterone">18-Hydroxycorticosterone</a></li> <li><a href="/w/index.php?title=18-Hydroxyprogesterone&action=edit&redlink=1" class="new" title="18-Hydroxyprogesterone (page does not exist)">18-Hydroxyprogesterone</a></li> <li><a href="/wiki/Aldosterone" title="Aldosterone">Aldosterone</a></li> <li><a href="/wiki/Corticosterone" title="Corticosterone">Corticosterone</a></li> <li><a href="/wiki/Cortisol" title="Cortisol">Cortisol</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sex_steroid" class="mw-redirect" title="Sex steroid">Sex steroids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Androgen" title="Androgen">Androgens</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/11-Ketodihydrotestosterone" title="11-Ketodihydrotestosterone">11-Ketodihydrotestosterone</a></li> <li><a href="/wiki/11-Ketotestosterone" title="11-Ketotestosterone">11-Ketotestosterone</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/11%CE%B2-Hydroxyandrostenedione" title="11β-Hydroxyandrostenedione">11β-Hydroxyandrostenedione</a></li> <li><a href="/wiki/Adrenosterone" title="Adrenosterone">Adrenosterone (11-ketoandrostenedione)</a></li> <li><a href="/wiki/Androstenediol" title="Androstenediol">Androstenediol</a></li> <li><a href="/wiki/Androstenedione" title="Androstenedione">Androstenedione</a></li> <li><a href="/wiki/Androsterone" title="Androsterone">Androsterone</a></li> <li><a href="/wiki/Dehydroandrosterone" title="Dehydroandrosterone">Dehydroandrosterone</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA sulfate</a></li> <li><a href="/wiki/Dihydrotestosterone" title="Dihydrotestosterone">Dihydrotestosterone</a></li> <li><a href="/wiki/Epiandrosterone" title="Epiandrosterone">Epiandrosterone</a></li> <li><a href="/wiki/Epitestosterone" title="Epitestosterone">Epitestosterone</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyandrostenedione" title="16α-Hydroxyandrostenedione">16α-Hydroxyandrostenedione</a></li> <li><a href="/wiki/16-Hydroxydehydroepiandrosterone" class="mw-redirect" title="16-Hydroxydehydroepiandrosterone">16α-Hydroxy-DHEA</a></li> <li><a href="/wiki/16-Hydroxydehydroepiandrosterone_sulfate" class="mw-redirect" title="16-Hydroxydehydroepiandrosterone sulfate">16α-Hydroxy-DHEA sulfate</a></li> <li><a href="/wiki/Testosterone" title="Testosterone">Testosterone</a></li></ul> <ul><li><i>Metabolites:</i> <a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/wiki/3%CE%B1-Androstanediol_glucuronide" class="mw-redirect" title="3α-Androstanediol glucuronide">3α-Androstanediol glucuronide</a></li> <li><a href="/wiki/3%CE%B2-Androstanediol" title="3β-Androstanediol">3β-Androstanediol</a></li> <li><a href="/wiki/5%CE%B2-Dihydrotestosterone" title="5β-Dihydrotestosterone">5β-Dihydrotestosterone</a></li> <li><a href="/wiki/3%CE%B1-Etiocholanediol" title="3α-Etiocholanediol">3α-Etiocholanediol</a></li> <li><a href="/wiki/3%CE%B2-Etiocholanediol" title="3β-Etiocholanediol">3β-Etiocholanediol</a></li> <li><a href="/w/index.php?title=Androstanetriol&action=edit&redlink=1" class="new" title="Androstanetriol (page does not exist)">Androstanetriols</a></li> <li><a href="/wiki/Androstenediol_sulfate" title="Androstenediol sulfate">Androstenediol sulfate</a></li> <li><a href="/wiki/Androstenetriol" title="Androstenetriol">Androstenetriol</a></li> <li><a href="/wiki/Androsterone_glucuronide" title="Androsterone glucuronide">Androsterone glucuronide</a></li> <li><a href="/wiki/Androsterone_sulfate" title="Androsterone sulfate">Androsterone sulfate</a></li> <li><a href="/w/index.php?title=Dihydrotestosterone_glucuronide&action=edit&redlink=1" class="new" title="Dihydrotestosterone glucuronide (page does not exist)">Dihydrotestosterone glucuronide</a></li> <li><a href="/w/index.php?title=Dihydrotestosterone_sulfate&action=edit&redlink=1" class="new" title="Dihydrotestosterone sulfate (page does not exist)">Dihydrotestosterone sulfate</a></li> <li><a href="/wiki/Etiocholanedione" title="Etiocholanedione">Etiocholanedione</a></li> <li><a href="/wiki/Etiocholanolone" title="Etiocholanolone">Etiocholanolone</a></li> <li><a href="/wiki/Etiocholanolone_glucuronide" title="Etiocholanolone glucuronide">Etiocholanolone glucuronide</a></li> <li><a href="/wiki/Epietiocholanolone" title="Epietiocholanolone">Epietiocholanolone</a></li> <li><a href="/wiki/Testosterone_glucuronide" title="Testosterone glucuronide">Testosterone glucuronide</a></li> <li><a href="/wiki/Testosterone_sulfate" title="Testosterone sulfate">Testosterone sulfate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Estrogen" title="Estrogen">Estrogens</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Estranes:</i> <a href="/wiki/Estetrol" title="Estetrol">Estetrol</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/wiki/Estrone" title="Estrone">Estrone</a></li> <li><a href="/wiki/Estriol" title="Estriol">Estriol</a></li> <li><a href="/wiki/17%CE%B1-Estradiol" title="17α-Estradiol">17α-Estradiol</a></li> <li><a href="/wiki/Epiestriol" title="Epiestriol">16β-Epiestriol (16β-hydroxyestradiol)</a></li> <li><a href="/wiki/17%CE%B1-Epiestriol" title="17α-Epiestriol">17α-Epiestriol (16α-hydroxy-17α-estradiol)</a></li> <li><a href="/wiki/16%CE%B2,17%CE%B1-Epiestriol" title="16β,17α-Epiestriol">16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)</a></li> <li><a href="/wiki/2-Hydroxyestradiol" title="2-Hydroxyestradiol">2-Hydroxyestradiol</a></li> <li><a href="/wiki/2-Hydroxyestriol" title="2-Hydroxyestriol">2-Hydroxyestriol</a></li> <li><a href="/wiki/2-Hydroxyestrone" title="2-Hydroxyestrone">2-Hydroxyestrone</a></li> <li><a href="/wiki/4-Hydroxyestradiol" title="4-Hydroxyestradiol">4-Hydroxyestradiol</a></li> <li><a href="/wiki/4-Hydroxyestriol" title="4-Hydroxyestriol">4-Hydroxyestriol</a></li> <li><a href="/wiki/4-Hydroxyestrone" title="4-Hydroxyestrone">4-Hydroxyestrone</a></li> <li><a href="/wiki/4-Methoxyestradiol" title="4-Methoxyestradiol">4-Methoxyestradiol</a></li> <li><a href="/wiki/4-Methoxyestrone" title="4-Methoxyestrone">4-Methoxyestrone</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyestrone" title="16α-Hydroxyestrone">16α-Hydroxyestrone</a></li> <li><a href="/wiki/16%CE%B2-Hydroxyestrone" title="16β-Hydroxyestrone">16β-Hydroxyestrone</a></li> <li><a href="/wiki/16-Ketoestradiol" title="16-Ketoestradiol">16-Ketoestradiol</a></li> <li><a href="/wiki/16-Ketoestrone" title="16-Ketoestrone">16-Ketoestrone</a></li></ul> <ul><li><i>Others:</i> <a href="/wiki/27-Hydroxycholesterol" title="27-Hydroxycholesterol">27-Hydroxycholesterol</a></li> <li><a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/wiki/3%CE%B2-Androstanediol" title="3β-Androstanediol">3β-Androstanediol</a></li> <li><a href="/wiki/4-Androstenedione" class="mw-redirect" title="4-Androstenedione">4-Androstenedione</a></li> <li><a href="/wiki/5-Androstenediol" class="mw-redirect" title="5-Androstenediol">5-Androstenediol</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA sulfate</a></li> <li><a href="/wiki/7-Keto-DHEA" title="7-Keto-DHEA">7-Keto-DHEA</a></li> <li><a href="/wiki/7%CE%B1-Hydroxy-DHEA" title="7α-Hydroxy-DHEA">7α-Hydroxy-DHEA</a></li> <li><a href="/wiki/16-Hydroxydehydroepiandrosterone" class="mw-redirect" title="16-Hydroxydehydroepiandrosterone">16α-Hydroxy-DHEA</a></li></ul> <ul><li><i>Metabolites:</i> <a href="/wiki/2-Methoxyestradiol" title="2-Methoxyestradiol">2-Methoxyestradiol</a></li> <li><a href="/wiki/2-Methoxyestrone" title="2-Methoxyestrone">2-Methoxyestrone</a></li> <li><a href="/wiki/2-Methoxyestriol" title="2-Methoxyestriol">2-Methoxyestriol</a></li> <li><a href="/wiki/4-Methoxyestriol" title="4-Methoxyestriol">4-Methoxyestriol</a></li> <li><a href="/wiki/Estradiol_disulfate" title="Estradiol disulfate">Estradiol disulfate</a></li> <li><a href="/wiki/Estradiol_glucuronide" title="Estradiol glucuronide">Estradiol glucuronide</a></li> <li><a href="/wiki/Estradiol_3-glucuronide" title="Estradiol 3-glucuronide">Estradiol 3-glucuronide</a></li> <li><a href="/wiki/Estradiol_3-glucuronide_17%CE%B2-sulfate" title="Estradiol 3-glucuronide 17β-sulfate">Estradiol 3-glucuronide 17β-sulfate</a></li> <li><a href="/wiki/Estradiol_sulfate" title="Estradiol sulfate">Estradiol sulfate</a></li> <li><a href="/wiki/Estradiol_17%CE%B2-sulfate" title="Estradiol 17β-sulfate">Estradiol 17β-sulfate</a></li> <li><a href="/wiki/Estrone_glucuronide" title="Estrone glucuronide">Estrone glucuronide</a></li> <li><a href="/wiki/Estrone_sulfate" title="Estrone sulfate">Estrone sulfate</a></li> <li><a href="/wiki/Estriol_glucuronide" title="Estriol glucuronide">Estriol glucuronide</a></li> <li><a href="/wiki/Estriol_sulfate" title="Estriol sulfate">Estriol sulfate</a></li> <li><a href="/wiki/Lipoidal_estradiol" title="Lipoidal estradiol">Lipoidal estradiol</a> (e.g., <a href="/wiki/Estradiol_stearate" title="Estradiol stearate">estradiol stearate</a>, <a href="/wiki/Estradiol_palmitate" title="Estradiol palmitate">estradiol palmitate</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Progestogen" title="Progestogen">Progestogens</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyprogesterone" title="16α-Hydroxyprogesterone">16α-Hydroxyprogesterone</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone</a></li> <li><a href="/wiki/20%CE%B1-Dihydroprogesterone" title="20α-Dihydroprogesterone">20α-Dihydroprogesterone</a></li> <li><a href="/wiki/20%CE%B2-Dihydroprogesterone" title="20β-Dihydroprogesterone">20β-Dihydroprogesterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">5α-Dihydroprogesterone</a></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone</a></li> <li><a href="/wiki/Dihydrodeoxycorticosterone" title="Dihydrodeoxycorticosterone">5α-DHDOC</a></li></ul> <ul><li><i>Metabolites:</i> <a href="/wiki/Allopregnanediol" title="Allopregnanediol">Allopregnanediol</a></li> <li><a href="/wiki/Pregnanediol" title="Pregnanediol">Pregnanediol</a></li> <li><a href="/wiki/Pregnanediol_glucuronide" title="Pregnanediol glucuronide">Pregnanediol glucuronide</a></li> <li><a href="/wiki/Pregnanetriol" title="Pregnanetriol">Pregnanetriol</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Neuroactive_steroid" class="mw-redirect" title="Neuroactive steroid">Neurosteroids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Cholestanes:</i> <a href="/wiki/24S-hydroxycholesterol" class="mw-redirect" title="24S-hydroxycholesterol">24<i>S</i>-Hydroxycholesterol</a></li> <li><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></li></ul> <ul><li><i>Pregnanes:</i> <a href="/wiki/3%CE%B1-Dihydroprogesterone" title="3α-Dihydroprogesterone">3α-Dihydroprogesterone</a></li> <li><a href="/wiki/3%CE%B2-Dihydroprogesterone" title="3β-Dihydroprogesterone">3β-Dihydroprogesterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydrocorticosterone" title="5α-Dihydrocorticosterone">5α-Dihydrocorticosterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">5α-Dihydroprogesterone</a></li> <li><a href="/wiki/5%CE%B2-Dihydroprogesterone" title="5β-Dihydroprogesterone">5β-Dihydroprogesterone</a></li> <li><a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone</a></li> <li><a href="/wiki/Corticosterone" title="Corticosterone">Corticosterone</a></li> <li><a href="/wiki/Dihydrocorticosterone" class="mw-redirect" title="Dihydrocorticosterone">DHC</a></li> <li><a href="/wiki/Dihydrodeoxycorticosterone" title="Dihydrodeoxycorticosterone">DHDOC</a></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone</a></li> <li><a href="/wiki/Epipregnanolone" title="Epipregnanolone">Epipregnanolone</a></li> <li><a href="/wiki/Isopregnanolone" title="Isopregnanolone">Isopregnanolone</a></li> <li><a href="/wiki/Pregnanolone" title="Pregnanolone">Pregnanolone</a></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a></li> <li><a href="/wiki/Pregnenolone_sulfate" title="Pregnenolone sulfate">Pregnenolone sulfate</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Tetrahydrocorticosterone" title="Tetrahydrocorticosterone">THB</a></li> <li><a href="/wiki/Tetrahydrodeoxycorticosterone" title="Tetrahydrodeoxycorticosterone">THDOC</a></li></ul> <ul><li><i>Androstanes:</i> <a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/wiki/3%CE%B1-Androstenol" class="mw-redirect" title="3α-Androstenol">3α-Androstenol</a></li> <li><a href="/wiki/7-Keto-DHEA" title="7-Keto-DHEA">7-Keto-DHEA</a></li> <li><a href="/wiki/7%CE%B1-Hydroxy-DHEA" title="7α-Hydroxy-DHEA">7α-Hydroxy-DHEA</a></li> <li><a href="/wiki/7%CE%B2-Hydroxy-DHEA" title="7β-Hydroxy-DHEA">7β-Hydroxy-DHEA</a></li> <li><a href="/wiki/7%CE%B1-Hydroxyepiandrosterone" title="7α-Hydroxyepiandrosterone">7α-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/Androsterone" title="Androsterone">Androsterone</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA sulfate</a></li> <li><a href="/wiki/Etiocholanolone" title="Etiocholanolone">Etiocholanolone</a></li></ul> <ul><li><b><a href="/wiki/Pheromone" title="Pheromone">Pheromones</a>:</b> <a href="/wiki/3%CE%B1-Androstenol" class="mw-redirect" title="3α-Androstenol">3α-Androstenol</a></li> <li><a href="/wiki/3%CE%B2-Androstenol" title="3β-Androstenol">3β-Androstenol</a></li> <li><a href="/wiki/Androstadienol" title="Androstadienol">Androstadienol</a></li> <li><a href="/wiki/Androstadienone" title="Androstadienone">Androstadienone</a></li> <li><a href="/wiki/Androstenone" title="Androstenone">Androstenone</a></li> <li><a href="/wiki/Androsterone" title="Androsterone">Androsterone</a></li> <li><a href="/wiki/Estratetraenol" title="Estratetraenol">Estratetraenol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b><a href="/wiki/Vitamin_D" title="Vitamin D">Vitamin D</a>:</b> <a href="/wiki/7-Dehydrocholesterol" title="7-Dehydrocholesterol">7-Dehydrocholesterol</a></li> <li><a href="/wiki/Calcifediol" title="Calcifediol">Calcidiol/Calcifediol</a></li> <li><a href="/wiki/Calcitriol" title="Calcitriol">Calcitriol</a></li> <li><a href="/wiki/Cholecalciferol" title="Cholecalciferol">Cholecalciferol</a></li></ul> <ul><li><b>Others:</b> <a href="/wiki/7%CE%B1-Hydroxycholesterol" title="7α-Hydroxycholesterol">7α-Hydroxycholesterol</a></li> <li><a href="/wiki/11%CE%B1-Hydroxyprogesterone" title="11α-Hydroxyprogesterone">11α-Hydroxyprogesterone</a></li> <li><a href="/wiki/11%CE%B2-Hydroxyprogesterone" title="11β-Hydroxyprogesterone">11β-Hydroxyprogesterone</a></li> <li><a href="/wiki/Cholesterol_sulfate" title="Cholesterol sulfate">Cholesterol sulfate</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Metabolism,_catabolism,_anabolism" style="padding:3px"><table class="nowraplinks hlist 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:Metabolism" title="Template:Metabolism"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Metabolism" title="Template talk:Metabolism"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Metabolism" title="Special:EditPage/Template:Metabolism"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Metabolism,_catabolism,_anabolism" style="font-size:114%;margin:0 4em"><a href="/wiki/Metabolism" title="Metabolism">Metabolism</a>, <a href="/wiki/Catabolism" title="Catabolism">catabolism</a>, <a href="/wiki/Anabolism" title="Anabolism">anabolism</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">General</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/Metabolic_pathway" title="Metabolic pathway">Metabolic pathway</a></li> <li><a href="/wiki/Metabolic_network" title="Metabolic network">Metabolic network</a></li> <li><a href="/wiki/Primary_nutritional_groups" title="Primary nutritional groups">Primary nutritional groups</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Bioenergetics" title="Bioenergetics">Energy<br /> metabolism</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Aerobic_respiration" class="mw-redirect" title="Aerobic respiration">Aerobic respiration</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/Glycolysis" title="Glycolysis">Glycolysis</a> → <a href="/wiki/Pyruvate_dehydrogenase" title="Pyruvate dehydrogenase">Pyruvate decarboxylation</a> → <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">Citric acid cycle</a> → <a href="/wiki/Oxidative_phosphorylation" title="Oxidative phosphorylation">Oxidative phosphorylation</a> (<span style="font-size:85%;"><a href="/wiki/Electron_transport_chain" title="Electron transport chain">electron transport chain</a> + <a href="/wiki/ATP_synthase" title="ATP synthase">ATP synthase</a></span>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Anaerobic_respiration" title="Anaerobic respiration">Anaerobic respiration</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>Electron acceptors other than oxygen</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Fermentation" title="Fermentation">Fermentation</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/Glycolysis" title="Glycolysis">Glycolysis</a> → <a href="/wiki/Substrate-level_phosphorylation" title="Substrate-level phosphorylation">Substrate-level phosphorylation</a> <ul><li><a href="/wiki/Acetone%E2%80%93butanol%E2%80%93ethanol_fermentation" title="Acetone–butanol–ethanol fermentation">ABE</a></li> <li><a href="/wiki/Ethanol_fermentation" title="Ethanol fermentation">Ethanol</a></li> <li><a href="/wiki/Lactic_acid_fermentation" title="Lactic acid fermentation">Lactic acid</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Specific<br /> paths</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Protein_metabolism" title="Protein metabolism">Protein metabolism</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/Protein_biosynthesis" title="Protein biosynthesis">Protein synthesis</a></li> <li><a href="/wiki/Protein_catabolism" title="Protein catabolism">Catabolism</a> (protein→peptide→amino acid)</li></ul> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Amino_acid" title="Amino acid">Amino acid</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/Amino_acid_synthesis" title="Amino acid synthesis">Amino acid synthesis</a></li> <li><a href="/wiki/Protein_catabolism#Amino_acid_degradation" title="Protein catabolism">Amino acid degradation</a> (amino acid→pyruvate, acetyl CoA, or TCA intermediate)</li> <li><a href="/wiki/Urea_cycle" title="Urea cycle">Urea cycle</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nucleic_acid_metabolism" title="Nucleic acid metabolism">Nucleotide<br /> metabolism</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/Purine_metabolism" title="Purine metabolism">Purine metabolism</a></li> <li><a href="/wiki/Nucleotide_salvage" title="Nucleotide salvage">Nucleotide salvage</a></li> <li><a href="/wiki/Pyrimidine_metabolism" title="Pyrimidine metabolism">Pyrimidine metabolism</a></li> <li><a href="/wiki/Purine_nucleotide_cycle" title="Purine nucleotide cycle">Purine nucleotide cycle</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/Carbohydrate_metabolism" title="Carbohydrate metabolism">Carbohydrate metabolism</a><br />(<a href="/wiki/Carbohydrate_catabolism" title="Carbohydrate catabolism">carbohydrate catabolism</a><br />and <a href="/wiki/Anabolism" title="Anabolism">anabolism</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Human</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><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Glycolysis" title="Glycolysis">Glycolysis</a> ⇄ <a href="/wiki/Gluconeogenesis" title="Gluconeogenesis">Gluconeogenesis</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Glycogenolysis" title="Glycogenolysis">Glycogenolysis</a> ⇄ <a href="/wiki/Glycogenesis" title="Glycogenesis">Glycogenesis</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Pentose_phosphate_pathway" title="Pentose phosphate pathway">Pentose phosphate pathway</a></li> <li><a href="/wiki/Fructolysis" title="Fructolysis">Fructolysis</a> <ul><li><a href="/wiki/Polyol_pathway" title="Polyol pathway">Polyol pathway</a></li></ul></li> <li><a href="/wiki/Galactolysis" title="Galactolysis">Galactolysis</a> <ul><li><a href="/wiki/Leloir_pathway" title="Leloir pathway">Leloir pathway</a></li></ul></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Glycosylation" title="Glycosylation">Glycosylation</a> <ul><li><a href="/wiki/N-linked_glycosylation" title="N-linked glycosylation">N-linked</a></li> <li><a href="/wiki/O-linked_glycosylation" title="O-linked glycosylation">O-linked</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Nonhuman</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><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Photosynthesis" title="Photosynthesis">Photosynthesis</a></li> <li><a href="/wiki/Anoxygenic_photosynthesis" title="Anoxygenic photosynthesis">Anoxygenic photosynthesis</a></li> <li><a href="/wiki/Chemosynthesis" title="Chemosynthesis">Chemosynthesis</a></li> <li><a href="/wiki/Carbon_fixation" class="mw-redirect" title="Carbon fixation">Carbon fixation</a></li> <li><a href="/w/index.php?title=DeLey-Doudoroff_pathway&action=edit&redlink=1" class="new" title="DeLey-Doudoroff pathway (page does not exist)">DeLey-Doudoroff pathway</a></li> <li><a href="/wiki/Entner-Doudoroff_pathway" class="mw-redirect" title="Entner-Doudoroff pathway">Entner-Doudoroff pathway</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Xylose_metabolism" title="Xylose metabolism">Xylose metabolism</a></li> <li><a href="/wiki/Radiotrophic_fungus" title="Radiotrophic fungus">Radiotrophism</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Lipid_metabolism" title="Lipid metabolism">Lipid metabolism</a> <br />(<a href="/wiki/Lipolysis" title="Lipolysis">lipolysis</a>, <a href="/wiki/Lipogenesis" title="Lipogenesis">lipogenesis</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Fatty_acid_metabolism" title="Fatty acid metabolism">Fatty acid metabolism</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/Fatty_acid_degradation" title="Fatty acid degradation">Fatty acid degradation</a> (<a href="/wiki/Beta_oxidation" title="Beta oxidation">Beta oxidation</a>)</li> <li><a href="/wiki/Fatty_acid_synthesis" title="Fatty acid synthesis">Fatty acid synthesis</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink selflink">Steroid metabolism</a></li> <li><a href="/wiki/Sphingolipid_metabolism" class="mw-redirect" title="Sphingolipid metabolism">Sphingolipid metabolism</a></li> <li><a href="/wiki/Eicosanoid_metabolism" class="mw-redirect" title="Eicosanoid metabolism">Eicosanoid metabolism</a></li> <li><a href="/wiki/Ketosis" title="Ketosis">Ketosis</a></li> <li><a href="/wiki/Reverse_cholesterol_transport" title="Reverse cholesterol transport">Reverse cholesterol transport</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Bioinorganic_chemistry" title="Bioinorganic chemistry">Metal metabolism</a> <ul><li><a href="/wiki/Human_iron_metabolism" title="Human iron metabolism">Iron metabolism</a></li></ul></li> <li><a href="/wiki/Ethanol_metabolism" class="mw-redirect" title="Ethanol metabolism">Ethanol metabolism</a></li> <li><a href="/wiki/Phosphagen" title="Phosphagen">Phospagen system (ATP-PCr)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Metabolism_map" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2" style="background:#E0E0E0"><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:MetabolismMap" title="Template:MetabolismMap"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:MetabolismMap" title="Template talk:MetabolismMap"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:MetabolismMap" title="Special:EditPage/Template:MetabolismMap"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Metabolism_map" style="font-size:114%;margin:0 4em"><a href="/wiki/Metabolism" title="Metabolism">Metabolism</a> map</div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"><div style="border:solid #ccc 1px;width:810px;margin: 0 auto"> <table role="presentation" cellpadding="0" style="border-spacing:0; margin-left: auto; margin-right: auto; border: none;"> <tbody><tr> <td><div class="thumb center" style="margin: 1em auto;"> <div class="thumbinner" style="width:802px;border:0px;background-color:#fff"> <div style="position:relative; width:800px; height:600px; overflow:hidden; border:0px; background-color:white;"> <div style="left:0px; top:0px; width:800px; position:absolute"> <span typeof="mw:File"><a href="/wiki/File:Metabolic_Metro_Map.svg" title="File:Metabolic Metro Map.svg"><img alt="Metro-style map of major metabolic pathways" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/41/Metabolic_Metro_Map_%28no_legends%29.svg/800px-Metabolic_Metro_Map_%28no_legends%29.svg.png" decoding="async" width="800" height="600" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/41/Metabolic_Metro_Map_%28no_legends%29.svg/1200px-Metabolic_Metro_Map_%28no_legends%29.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/41/Metabolic_Metro_Map_%28no_legends%29.svg/1600px-Metabolic_Metro_Map_%28no_legends%29.svg.png 2x" data-file-width="1260" data-file-height="945" /></a></span> </div> <div style="text-align:center; font-size:8px; line-height:110%"> <div style="background-color:transparent; color:black"><div id="annotation_225x150" style="position:absolute; left:225px; top:150px; font-size:15px; font-size:15; line-height:17px;"><span style="background-color:; color:inherit;"> <i><a href="/wiki/Carbon_fixation" class="mw-redirect" title="Carbon fixation"><span style="color:#bc00bc;">Carbon<br />fixation</span></a></i> </span></div> <div id="annotation_135x185" style="position:absolute; left:135px; top:185px; font-size:15px; font-size:15; line-height:17px;"><span style="background-color:; color:inherit;"> <i><a href="/wiki/Photorespiration" title="Photorespiration"><span style="color:#5400a9;">Photo-<br />respiration</span></a></i> </span></div> <div id="annotation_395x140" style="position:absolute; left:395px; top:140px; font-size:15px; font-size:15; line-height:17px;"><span style="background-color:; color:inherit;"> <i><a href="/wiki/Pentose_phosphate_pathway" title="Pentose phosphate pathway"><span style="color:#bc00bc;">Pentose<br />phosphate<br />pathway</span></a></i> </span></div> <div id="annotation_215x340" style="position:absolute; left:215px; top:340px; font-size:15px; font-size:15; line-height:17px;"><span style="background-color:; color:inherit;"> <i><a href="/wiki/Citric_acid_cycle" title="Citric acid cycle"><span style="color:#edb500;">Citric<br />acid cycle</span></a></i> </span></div> <div id="annotation_365x505" style="position:absolute; left:365px; top:505px; font-size:15px; font-size:15; line-height:17px;"><span style="background-color:; color:inherit;"> <i><a href="/wiki/Glyoxylate_cycle" title="Glyoxylate cycle"><span style="color:#edb500;">Glyoxylate<br />cycle</span></a></i> </span></div> <div id="annotation_125x398" style="position:absolute; left:125px; top:398px; font-size:15px; font-size:15; line-height:17px;"><span style="background-color:; color:inherit;"> <i><a href="/wiki/Urea_cycle" title="Urea cycle"><span style="color:#89dd00;">Urea<br />cycle</span></a></i> </span></div> <div id="annotation_495x260" style="position:absolute; left:495px; top:260px; font-size:15px; font-size:15; line-height:17px;"><span style="background-color:; color:inherit;"> <i><a href="/wiki/Fatty_acid_synthesis" title="Fatty acid synthesis"><span style="color:#00d300;">Fatty<br />acid<br />synthesis</span></a></i> </span></div> <div id="annotation_495x335" style="position:absolute; left:495px; top:335px; font-size:15px; font-size:15; line-height:17px;"><span style="background-color:; color:inherit;"> <i><a href="/wiki/Fatty_acid_synthesis" title="Fatty acid synthesis"><span style="color:#00d300;">Fatty<br />acid<br />elongation</span></a></i> </span></div> <div id="annotation_497x425" style="position:absolute; left:497px; top:425px; font-size:15px; font-size:15; line-height:17px;"><span style="background-color:; color:inherit;"> <i><a href="/wiki/Beta_oxidation" title="Beta oxidation"><span style="color:#ff66cc;">Beta<br />oxidation</span></a></i> </span></div> <div id="annotation_495x495" style="position:absolute; left:495px; top:495px; font-size:12px; font-size:12; line-height:14px;"><span style="background-color:; color:inherit;"> <i><a href="/wiki/Beta_oxidation#Peroxisomal_beta-oxidation" title="Beta oxidation"><span style="color:#ff66cc;">Peroxisomal</span></a></i> </span></div> <div id="annotation_497x510" style="position:absolute; left:497px; top:510px; font-size:15px; font-size:15; line-height:17px;"><span style="background-color:; color:inherit;"> <i><a href="/wiki/Beta_oxidation#Peroxisomal_beta-oxidation" title="Beta oxidation"><span style="color:#ff66cc;">beta<br />oxidation</span></a></i> </span></div> <p><br /> </p> <div id="annotation_295x42" style="position:absolute; left:295px; top:42px; font-size:9px; font-size:9; line-height:11px; text-align:right;"><span style="background-color:; color:inherit;"> <i><b><a href="/wiki/Glycogenolysis" title="Glycogenolysis"><span style="color:#8a2c2c;">Glyco-<br />genolysis</span></a></b></i> </span></div> <div id="annotation_280x80" style="position:absolute; left:280px; top:80px; font-size:9px; font-size:9; line-height:11px; text-align:left;"><span style="background-color:; color:inherit;"> <i><b><a href="/wiki/Glycogenesis" title="Glycogenesis"><span style="color:#2e427e;">Glyco-<br />genesis</span></a></b></i> </span></div> <div id="annotation_360x160" style="position:absolute; left:360px; top:160px; font-size:9px; font-size:9; line-height:11px; text-align:left;"><span style="background-color:; color:inherit;"> <i><b><a href="/wiki/Glycolysis" title="Glycolysis"><span style="color:#ea0000;">Glyco-<br />lysis</span></a></b></i> </span></div> <div id="annotation_300x160" style="position:absolute; left:300px; top:160px; font-size:9px; font-size:9; line-height:11px; text-align:right;"><span style="background-color:; color:inherit;"> <i><b><a href="/wiki/Gluconeogenesis" title="Gluconeogenesis"><span style="color:#0033cc;">Gluconeo-<br />genesis</span></a></b></i> </span></div> <div id="annotation_310x332" style="position:absolute; left:310px; top:332px; font-size:9px; font-size:9; line-height:11px; text-align:right;"><span style="background-color:; color:inherit;"> <i><b><a href="/wiki/Pyruvate_dehydrogenase" title="Pyruvate dehydrogenase"><span style="color:#ea6000;">Pyruvate<br />decarb-<br />oxylation</span></a></b></i> </span></div> <div id="annotation_365x335" style="position:absolute; left:365px; top:335px; font-size:9px; font-size:9; line-height:11px;"><span style="background-color:; color:inherit;"> <i><b><a href="/wiki/Lactic_acid_fermentation" title="Lactic acid fermentation"><span style="color:#d47ff0;">Fermentation</span></a></b></i> </span></div> <div id="annotation_325x430" style="position:absolute; left:325px; top:430px; font-size:9px; font-size:9; line-height:11px; text-align:right;"><span style="background-color:; color:inherit;"> <i><b><a href="/wiki/Ketone_bodies" title="Ketone bodies"><span style="color:#e06c1f;">Keto-<br />lysis</span></a></b></i> </span></div> <div id="annotation_365x430" style="position:absolute; left:365px; top:430px; font-size:9px; font-size:9; line-height:11px; text-align:left;"><span style="background-color:; color:inherit;"> <i><b><a href="/wiki/Ketogenesis" title="Ketogenesis"><span style="color:#5f8216;">Keto-<br />genesis</span></a></b></i> </span></div> <div id="annotation_195x470" style="position:absolute; left:195px; top:470px; font-size:9px; font-size:9; line-height:11px; text-align:left;"><span style="background-color:; color:inherit;"> <i><b><a href="/wiki/Gluconeogenesis" title="Gluconeogenesis"><span style="color:#0033cc;">feeders to<br />gluconeo-<br />genesis</span></a></b></i> </span></div> <div id="annotation_225x230" style="position:absolute; left:225px; top:230px; font-size:9px; font-size:9; line-height:11px; text-align:right;"><span style="background-color:; color:inherit;"> <i><b><a href="/wiki/Carbon_fixation#Carbon_concentrating_mechanisms" class="mw-redirect" title="Carbon fixation"><span style="color:#9373d3;">Direct / C4 / CAM<br />carbon intake</span></a></b></i> </span></div> <div id="annotation_125x143" style="position:absolute; left:125px; top:143px; font-size:9px; font-size:9; line-height:11px;"><span style="background-color:; color:inherit;"> <i><b><a href="/wiki/Light-dependent_reactions" title="Light-dependent reactions"><span style="color:#9373d3;">Light reaction</span></a></b></i> </span></div> <div id="annotation_115x355" style="position:absolute; left:115px; top:355px; font-size:9px; font-size:9; line-height:11px;"><span style="background-color:; color:inherit;"> <i><b><a href="/wiki/Oxidative_phosphorylation" title="Oxidative phosphorylation"><span style="color:#c34747;">Oxidative<br />phosphorylation</span></a></b></i> </span></div> <div id="annotation_25x415" style="position:absolute; left:25px; top:415px; font-size:9px; font-size:9; line-height:11px;"><span style="background-color:; color:inherit;"> <i><b><a href="/wiki/Deamination" title="Deamination"><span style="color:#4999c2;">Amino acid<br />deamination</span></a></b></i> </span></div> <div id="annotation_315x288" style="position:absolute; left:315px; top:288px; font-size:9px; font-size:9; line-height:11px;"><span style="background-color:; color:inherit;"> <i><b><a href="/wiki/Fatty_acid_synthesis#Glycolytic_end_products_are_used_in_the_conversion_of_carbohydrates_into_fatty_acids" title="Fatty acid synthesis"><span style="color:#00d300;">Citrate<br />shuttle</span></a></b></i> </span></div> <div id="annotation_590x415" style="position:absolute; left:590px; top:415px; font-size:9px; font-size:9; line-height:11px; text-align:left;"><span style="background-color:; color:inherit;"> <i><b><a href="/wiki/Lipogenesis" title="Lipogenesis"><span style="color:#00d300;">Lipogenesis</span></a></b></i> </span></div> <div id="annotation_590x455" style="position:absolute; left:590px; top:455px; font-size:9px; font-size:9; line-height:11px; text-align:left;"><span style="background-color:; color:inherit;"> <i><b><a href="/wiki/Lipolysis" title="Lipolysis"><span style="color:#ff66cc;">Lipolysis</span></a></b></i> </span></div> <div id="annotation_585x260" style="position:absolute; left:585px; top:260px; font-size:9px; font-size:9; line-height:11px;"><span style="background-color:; color:inherit;"> <i><b><a class="mw-selflink-fragment" href="#Steroidogenesis"><span style="color:#0099cc;">Steroidogenesis</span></a></b></i> </span></div> <div id="annotation_470x235" style="position:absolute; left:470px; top:235px; font-size:9px; font-size:9; line-height:11px;"><span style="background-color:; color:inherit;"> <i><b><a href="/wiki/Mevalonate_pathway" title="Mevalonate pathway"><span style="color:#0099cc;">MVA pathway</span></a></b></i> </span></div> <div id="annotation_460x210" style="position:absolute; left:460px; top:210px; font-size:9px; font-size:9; line-height:11px;"><span style="background-color:; color:inherit;"> <i><b><a href="/wiki/Non-mevalonate_pathway" title="Non-mevalonate pathway"><span style="color:#af753a;">MEP pathway</span></a></b></i> </span></div> <div id="annotation_487x153" style="position:absolute; left:487px; top:153px; font-size:9px; font-size:9; line-height:11px;"><span style="background-color:; color:inherit;"> <i><b><a href="/wiki/Shikimate_pathway" title="Shikimate pathway"><span style="color:#00cc99;">Shikimate<br />pathway</span></a></b></i> </span></div> <div id="annotation_555x105" style="position:absolute; left:555px; top:105px; font-size:9px; font-size:9; line-height:11px;"><span style="background-color:; color:inherit;"> <i><b><a href="/wiki/Transcription_(genetics)" class="mw-redirect" title="Transcription (genetics)"><span style="color:#79793d;">Transcription &</span></a><br /><a href="/wiki/DNA_replication" title="DNA replication"><span style="color:#79793d;">replication</span></a></b></i> </span></div> <div id="annotation_600x83" style="position:absolute; left:600px; top:83px; font-size:9px; font-size:9; line-height:11px;"><span style="background-color:; color:inherit;"> <i><b><a href="/wiki/Translation_(biology)" title="Translation (biology)"><span style="color:#79793d;">Translation</span></a></b></i> </span></div> <div id="annotation_600x57" style="position:absolute; left:600px; top:57px; font-size:9px; font-size:9; line-height:11px;"><span style="background-color:; color:inherit;"> <i><b><a href="/wiki/Proteolysis" title="Proteolysis"><span style="color:#6666cc;">Proteolysis</span></a></b></i> </span></div> <div id="annotation_687x55" style="position:absolute; left:687px; top:55px; font-size:9px; font-size:9; line-height:11px;"><span style="background-color:; color:inherit;"> <i><b><a href="/wiki/Glycosylation" title="Glycosylation"><span style="color:#79793d;">Glycosyl-<br />ation</span></a></b></i> </span></div> <p><br /> </p> <div id="annotation_210x38" style="position:absolute; left:210px; top:38px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Sugar_acid" title="Sugar acid">Sugar<br />acids</a> </span></div> <div id="annotation_240x38" style="position:absolute; left:240px; top:38px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Disaccharide" title="Disaccharide">Double</a>/<a href="/wiki/Polysaccharide" title="Polysaccharide">multiple<br />sugars</a> & <a href="/wiki/Glycan" title="Glycan">glycans</a> </span></div> <div id="annotation_340x38" style="position:absolute; left:340px; top:38px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Monosaccharide" title="Monosaccharide">Simple<br />sugars</a> </span></div> <div id="annotation_380x45" style="position:absolute; left:380px; top:45px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Inositol_phosphate" title="Inositol phosphate">Inositol-P</a> </span></div> <div id="annotation_160x90" style="position:absolute; left:160px; top:90px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Amino_sugar" title="Amino sugar">Amino sugars</a><br />& <a href="/wiki/Sialic_acid" title="Sialic acid">sialic acids</a> </span></div> <div id="annotation_245x120" style="position:absolute; left:245px; top:120px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Nucleotide_sugar" title="Nucleotide sugar">Nucleotide sugars</a> </span></div> <div id="annotation_365x105" style="position:absolute; left:365px; top:105px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Glucose_6-phosphate" title="Glucose 6-phosphate">Hexose-P</a> </span></div> <div id="annotation_315x180" style="position:absolute; left:315px; top:180px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Glyceraldehyde_3-phosphate" title="Glyceraldehyde 3-phosphate">Triose-P</a> </span></div> <div id="annotation_305x240" style="position:absolute; left:305px; top:240px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Glycerol" title="Glycerol">Glycerol</a> </span></div> <div id="annotation_300x260" style="position:absolute; left:300px; top:260px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Phosphoglycerate" title="Phosphoglycerate">P-glycerates</a> </span></div> <div id="annotation_425x110" style="position:absolute; left:425px; top:110px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Ribose_5-phosphate" title="Ribose 5-phosphate">Pentose-P</a> </span></div> <div id="annotation_470x190" style="position:absolute; left:470px; top:190px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Erythrose_4-phosphate" title="Erythrose 4-phosphate">Tetrose-P</a> </span></div> <div id="annotation_410x440" style="position:absolute; left:410px; top:440px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Propionyl-CoA" title="Propionyl-CoA">Propionyl<br />-CoA</a> </span></div> <div id="annotation_310x495" style="position:absolute; left:310px; top:495px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Succinic_acid" title="Succinic acid">Succinate</a> </span></div> <div id="annotation_455x530" style="position:absolute; left:455px; top:530px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">Acetyl<br />-CoA</a> </span></div> <div id="annotation_150x155" style="position:absolute; left:150px; top:155px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Ribose_5-phosphate" title="Ribose 5-phosphate">Pentose-P</a> </span></div> <div id="annotation_230x210" style="position:absolute; left:230px; top:210px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Phosphoglycerate" title="Phosphoglycerate">P-glycerates</a> </span></div> <div id="annotation_85x180" style="position:absolute; left:85px; top:180px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Glyoxylic_acid" title="Glyoxylic acid">Glyoxylate</a> </span></div> <div id="annotation_65x152" style="position:absolute; left:65px; top:152px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Photosystem" title="Photosystem">Photosystems</a> </span></div> <div id="annotation_320x310" style="position:absolute; left:320px; top:310px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Pyruvic_acid" title="Pyruvic acid">Pyruvate</a> </span></div> <div id="annotation_410x308" style="position:absolute; left:410px; top:308px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Lactic_acid" title="Lactic acid">Lactate</a> </span></div> <div id="annotation_365x345" style="position:absolute; left:365px; top:345px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">Acetyl<br />-CoA</a> </span></div> <div id="annotation_295x380" style="position:absolute; left:295px; top:380px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Citric_acid" title="Citric acid">Citrate</a> </span></div> <div id="annotation_270x300" style="position:absolute; left:270px; top:300px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Oxaloacetic_acid" title="Oxaloacetic acid">Oxalo-<br />acetate</a> </span></div> <div id="annotation_200x310" style="position:absolute; left:200px; top:310px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Malic_acid" title="Malic acid">Malate</a> </span></div> <div id="annotation_195x405" style="position:absolute; left:195px; top:405px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Succinyl-CoA" title="Succinyl-CoA">Succinyl<br />-CoA</a> </span></div> <div id="annotation_275x405" style="position:absolute; left:275px; top:405px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Alpha-Ketoglutaric_acid" class="mw-redirect" title="Alpha-Ketoglutaric acid">α-Keto-<br />glutarate</a> </span></div> <div id="annotation_370x455" style="position:absolute; left:370px; top:455px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Ketone_bodies" title="Ketone bodies">Ketone<br />bodies</a> </span></div> <div id="annotation_70x365" style="position:absolute; left:70px; top:365px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Electron_transport_chain" title="Electron transport chain">Respiratory<br />chain</a> </span></div> <div id="annotation_370x265" style="position:absolute; left:370px; top:265px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Serine" title="Serine">Serine group</a> </span></div> <div id="annotation_395x290" style="position:absolute; left:395px; top:290px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Alanine" title="Alanine">Alanine</a> </span></div> <div id="annotation_415x345" style="position:absolute; left:415px; top:345px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Branched-chain_amino_acid" title="Branched-chain amino acid">Branched-chain<br />amino acids</a> </span></div> <div id="annotation_275x275" style="position:absolute; left:275px; top:275px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Aspartic_acid" title="Aspartic acid">Aspartate<br />group</a> </span></div> <div id="annotation_180x250" style="position:absolute; left:180px; top:250px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Homoserine" title="Homoserine">Homoserine<br />group</a><br />& <a href="/wiki/Lysine" title="Lysine">lysine</a> </span></div> <div id="annotation_280x445" style="position:absolute; left:280px; top:445px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Glutamic_acid" title="Glutamic acid">Glutamate<br />group</a><br />& <a href="/wiki/Proline" title="Proline">proline</a> </span></div> <div id="annotation_105x465" style="position:absolute; left:105px; top:465px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Arginine" title="Arginine">Arginine</a> </span></div> <div id="annotation_40x465" style="position:absolute; left:40px; top:465px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Creatine" title="Creatine">Creatine</a><br />& <a href="/wiki/Polyamine" title="Polyamine">polyamines</a> </span></div> <div id="annotation_415x385" style="position:absolute; left:415px; top:385px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Ketogenic_amino_acid" title="Ketogenic amino acid">Ketogenic</a> &<br /><a href="/wiki/Glucogenic_amino_acid" title="Glucogenic amino acid">glucogenic<br />amino acids</a> </span></div> <div id="annotation_550x85" style="position:absolute; left:550px; top:85px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Amino_acid" title="Amino acid">Amino acids</a> </span></div> <div id="annotation_520x190" style="position:absolute; left:520px; top:190px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Shikimic_acid" title="Shikimic acid">Shikimate</a> </span></div> <div id="annotation_635x165" style="position:absolute; left:635px; top:165px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Aromatic_amino_acid" title="Aromatic amino acid">Aromatic amino<br />acids</a> & <a href="/wiki/Histidine" title="Histidine">histidine</a> </span></div> <div id="annotation_158x38" style="position:absolute; left:158px; top:38px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Ascorbate" class="mw-redirect" title="Ascorbate">Ascorbate</a><br />(<a href="/wiki/Vitamin_C" title="Vitamin C">vitamin C</a>) </span></div> <div id="annotation_275x490" style="position:absolute; left:275px; top:490px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Aminolevulinic_acid" title="Aminolevulinic acid">δ-ALA</a> </span></div> <div id="annotation_155x510" style="position:absolute; left:155px; top:510px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Bile_pigment" class="mw-redirect" title="Bile pigment">Bile<br />pigments</a> </span></div> <div id="annotation_210x520" style="position:absolute; left:210px; top:520px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Heme" title="Heme">Hemes</a> </span></div> <div id="annotation_245x585" style="position:absolute; left:245px; top:585px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Cobalamin" class="mw-redirect" title="Cobalamin">Cobalamins</a> (<a href="/wiki/Vitamin_B" class="mw-redirect" title="Vitamin B">vitamin B<sub>12</sub></a>) </span></div> <div id="annotation_425x45" style="position:absolute; left:425px; top:45px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Vitamin_B" class="mw-redirect" title="Vitamin B">Various<br />vitamin Bs</a> </span></div> <div id="annotation_625x300" style="position:absolute; left:625px; top:300px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Calciferol" class="mw-redirect" title="Calciferol">Calciferols</a><br />(<a href="/wiki/Vitamin_D" title="Vitamin D">vitamin D</a>) </span></div> <div id="annotation_725x235" style="position:absolute; left:725px; top:235px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Retinoid" title="Retinoid">Retinoids</a><br />(<a href="/wiki/Vitamin_A" title="Vitamin A">vitamin A</a>) </span></div> <div id="annotation_590x190" style="position:absolute; left:590px; top:190px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Quinone" title="Quinone">Quinones</a> (<a href="/wiki/Vitamin_K" title="Vitamin K">vitamin K</a>)<br />& <a href="/wiki/Tocopherol" title="Tocopherol">tocopherols</a> (<a href="/wiki/Vitamin_E" title="Vitamin E">vitamin E</a>) </span></div> <div id="annotation_665x140" style="position:absolute; left:665px; top:140px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Cofactor_(biochemistry)" title="Cofactor (biochemistry)">Cofactors</a> </span></div> <div id="annotation_745x140" style="position:absolute; left:745px; top:140px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Vitamin" title="Vitamin">Vitamins</a><br />& <a href="/wiki/Metalloprotein" title="Metalloprotein">minerals</a> </span></div> <div id="annotation_720x185" style="position:absolute; left:720px; top:185px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Antioxidant" title="Antioxidant">Antioxidants</a> </span></div> <div id="annotation_490x140" style="position:absolute; left:490px; top:140px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Phosphoribosyl_pyrophosphate" title="Phosphoribosyl pyrophosphate">PRPP</a> </span></div> <div id="annotation_535x140" style="position:absolute; left:535px; top:140px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Nucleotide" title="Nucleotide">Nucleotides</a> </span></div> <div id="annotation_610x140" style="position:absolute; left:610px; top:140px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Nucleic_acid" title="Nucleic acid">Nucleic<br />acids</a> </span></div> <div id="annotation_665x87" style="position:absolute; left:665px; top:87px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Protein" title="Protein">Proteins</a> </span></div> <div id="annotation_710x87" style="position:absolute; left:710px; top:87px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Glycoprotein" title="Glycoprotein">Glycoproteins</a><br />& <a href="/wiki/Proteoglycan" title="Proteoglycan">proteoglycans</a> </span></div> <div id="annotation_280x520" style="position:absolute; left:280px; top:520px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Chlorophyll" title="Chlorophyll">Chlorophylls</a> </span></div> <div id="annotation_410x235" style="position:absolute; left:410px; top:235px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Methylerythritol_phosphate" class="mw-redirect" title="Methylerythritol phosphate">MEP</a> </span></div> <div id="annotation_420x245" style="position:absolute; left:420px; top:245px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Mevalonic_acid" title="Mevalonic acid">MVA</a> </span></div> <div id="annotation_420x260" style="position:absolute; left:420px; top:260px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">Acetyl<br />-CoA</a> </span></div> <div id="annotation_440x330" style="position:absolute; left:440px; top:330px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Polyketide" title="Polyketide">Polyketides</a> </span></div> <div id="annotation_555x230" style="position:absolute; left:555px; top:230px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Isopentenyl_pyrophosphate" title="Isopentenyl pyrophosphate">Terpenoid<br />backbones</a> </span></div> <div id="annotation_625x235" style="position:absolute; left:625px; top:235px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Terpenoid" title="Terpenoid">Terpenoids</a><br />& <a href="/wiki/Carotenoid" title="Carotenoid">carotenoids</a> (<a href="/wiki/Vitamin_A" title="Vitamin A">vitamin A</a>) </span></div> <div id="annotation_640x287" style="position:absolute; left:640px; top:287px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a> </span></div> <div id="annotation_720x287" style="position:absolute; left:720px; top:287px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Bile_acid" title="Bile acid">Bile acids</a> </span></div> <div id="annotation_640x330" style="position:absolute; left:640px; top:330px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Glycerophospholipid" title="Glycerophospholipid">Glycero-<br />phospholipids</a> </span></div> <div id="annotation_600x397" style="position:absolute; left:600px; top:397px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Glycerolipid" class="mw-redirect" title="Glycerolipid">Glycerolipids</a> </span></div> <div id="annotation_620x430" style="position:absolute; left:620px; top:430px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Acyl-CoA" title="Acyl-CoA">Acyl-CoA</a> </span></div> <div id="annotation_630x500" style="position:absolute; left:630px; top:500px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Fatty_acid" title="Fatty acid">Fatty<br />acids</a> </span></div> <div id="annotation_720x350" style="position:absolute; left:720px; top:350px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Glycosphingolipid" title="Glycosphingolipid">Glyco-<br />sphingolipids</a> </span></div> <div id="annotation_720x397" style="position:absolute; left:720px; top:397px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Sphingolipid" title="Sphingolipid">Sphingolipids</a> </span></div> <div id="annotation_720x440" style="position:absolute; left:720px; top:440px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Wax" title="Wax">Waxes</a> </span></div> <div id="annotation_680x497" style="position:absolute; left:680px; top:497px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Polyunsaturated_fatty_acid" class="mw-redirect" title="Polyunsaturated fatty acid">Polyunsaturated<br />fatty acids</a> </span></div> <div id="annotation_470x45" style="position:absolute; left:470px; top:45px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Neurotransmitters" class="mw-redirect" title="Neurotransmitters">Neurotransmitters</a><br />& <a href="/wiki/Thyroid_hormone" class="mw-redirect" title="Thyroid hormone">thyroid hormones</a> </span></div> <div id="annotation_705x305" style="position:absolute; left:705px; top:305px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a class="mw-selflink selflink">Steroids</a> </span></div> <div id="annotation_587x330" style="position:absolute; left:587px; top:330px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Endocannabinoid_system" title="Endocannabinoid system">Endo-<br />cannabinoids</a> </span></div> <div id="annotation_735x465" style="position:absolute; left:735px; top:465px; line-height:110%;"><span style="background-color:transparent; color:inherit;"> <a href="/wiki/Eicosanoid" title="Eicosanoid">Eicosanoids</a> </span></div></div> </div> </div> </div> </div> </td></tr></tbody></table></div><div class="thumbcaption"><div style="float:left;margin-right:0.5em"><span typeof="mw:File"><span title="The image above contains clickable links"><img alt="The image above contains clickable links" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/18px-Interactive_icon.svg.png" decoding="async" width="18" height="27" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/27px-Interactive_icon.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/36px-Interactive_icon.svg.png 2x" data-file-width="133" data-file-height="200" /></span></span></div> Major <a href="/wiki/Metabolic_pathway" title="Metabolic pathway">metabolic pathways</a> in <a href="/wiki/Transit_map" title="Transit map">metro-style map</a>. Click any text (name of pathway or metabolites) to link to the corresponding article.<br />Single lines: pathways common to most lifeforms. Double lines: pathways not in humans (occurs in e.g. plants, fungi, prokaryotes). <span class="nowrap"><span typeof="mw:File"><span><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a0/Metabolic_metro_orange.svg/15px-Metabolic_metro_orange.svg.png" decoding="async" width="15" height="17" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a0/Metabolic_metro_orange.svg/23px-Metabolic_metro_orange.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a0/Metabolic_metro_orange.svg/30px-Metabolic_metro_orange.svg.png 2x" data-file-width="30" data-file-height="34" /></span></span> Orange nodes: <a href="/wiki/Carbohydrate_metabolism" title="Carbohydrate metabolism">carbohydrate metabolism</a>.</span> <span class="nowrap"><span typeof="mw:File"><span><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e7/Metabolic_metro_purple.svg/15px-Metabolic_metro_purple.svg.png" decoding="async" width="15" height="17" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e7/Metabolic_metro_purple.svg/23px-Metabolic_metro_purple.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e7/Metabolic_metro_purple.svg/30px-Metabolic_metro_purple.svg.png 2x" data-file-width="30" data-file-height="34" /></span></span> Violet nodes: <a href="/wiki/Photosynthesis" title="Photosynthesis">photosynthesis</a>.</span> <span class="nowrap"><span typeof="mw:File"><span><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/ba/Metabolic_metro_red.svg/15px-Metabolic_metro_red.svg.png" decoding="async" width="15" height="17" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/ba/Metabolic_metro_red.svg/23px-Metabolic_metro_red.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/ba/Metabolic_metro_red.svg/30px-Metabolic_metro_red.svg.png 2x" data-file-width="30" data-file-height="34" /></span></span> Red nodes: <a href="/wiki/Cellular_respiration" title="Cellular respiration">cellular respiration</a>.</span> <span class="nowrap"><span typeof="mw:File"><span><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/db/Metabolic_metro_pink.svg/15px-Metabolic_metro_pink.svg.png" decoding="async" width="15" height="17" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/db/Metabolic_metro_pink.svg/23px-Metabolic_metro_pink.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/db/Metabolic_metro_pink.svg/30px-Metabolic_metro_pink.svg.png 2x" data-file-width="30" data-file-height="34" /></span></span> Pink nodes: <a href="/wiki/Cell_signaling" title="Cell signaling">cell signaling</a>.</span> <span class="nowrap"><span typeof="mw:File"><span><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Metabolic_metro_blue.svg/15px-Metabolic_metro_blue.svg.png" decoding="async" width="15" height="17" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Metabolic_metro_blue.svg/23px-Metabolic_metro_blue.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Metabolic_metro_blue.svg/30px-Metabolic_metro_blue.svg.png 2x" data-file-width="30" data-file-height="34" /></span></span> Blue nodes: <a href="/wiki/Amino_acid_metabolism" class="mw-redirect" title="Amino acid metabolism">amino acid metabolism</a>.</span> <span class="nowrap"><span typeof="mw:File"><span><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c8/Metabolic_metro_grey.svg/15px-Metabolic_metro_grey.svg.png" decoding="async" width="15" height="17" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c8/Metabolic_metro_grey.svg/23px-Metabolic_metro_grey.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c8/Metabolic_metro_grey.svg/30px-Metabolic_metro_grey.svg.png 2x" data-file-width="30" data-file-height="34" /></span></span> Grey nodes: <a href="/wiki/Vitamin" title="Vitamin">vitamin</a> and <a href="/wiki/Cofactor_(biochemistry)" title="Cofactor (biochemistry)">cofactor</a> metabolism.</span> <span class="nowrap"><span typeof="mw:File"><span><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Metabolic_metro_brown.svg/15px-Metabolic_metro_brown.svg.png" decoding="async" width="15" height="17" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Metabolic_metro_brown.svg/23px-Metabolic_metro_brown.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/99/Metabolic_metro_brown.svg/30px-Metabolic_metro_brown.svg.png 2x" data-file-width="30" data-file-height="34" /></span></span> Brown nodes: <a href="/wiki/Nucleic_acid_metabolism" title="Nucleic acid metabolism">nucleotide</a> and <a href="/wiki/Protein_metabolism" title="Protein metabolism">protein</a> metabolism.</span> <span class="nowrap"><span typeof="mw:File"><span><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/97/Metabolic_metro_green.svg/15px-Metabolic_metro_green.svg.png" decoding="async" width="15" height="17" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/97/Metabolic_metro_green.svg/23px-Metabolic_metro_green.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/97/Metabolic_metro_green.svg/30px-Metabolic_metro_green.svg.png 2x" data-file-width="30" data-file-height="34" /></span></span> Green nodes: <a href="/wiki/Lipid_metabolism" title="Lipid metabolism">lipid metabolism</a>.</span></div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Steroid_signaling" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2" style="background:#e8e8ff;"><div id="Steroid_signaling" style="font-size:114%;margin:0 4em">Steroid signaling</div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;font-size:114%"><div style="padding:0px"> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Androgen_receptor_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Androgen_receptor_modulators" title="Template:Androgen receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Androgen_receptor_modulators" title="Template talk:Androgen receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Androgen_receptor_modulators" title="Special:EditPage/Template:Androgen receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Androgen_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Androgen_receptor" title="Androgen receptor">Androgen receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Androgen_receptor" title="Androgen receptor"><abbr title="Androgen receptor">AR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Androgen receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Testosterone derivatives:</i> <a href="/wiki/4-Androstenediol" title="4-Androstenediol">4-Androstenediol</a></li> <li><a href="/wiki/4-Dehydroepiandrosterone" title="4-Dehydroepiandrosterone">4-Dehydroepiandrosterone (4-DHEA)</a></li> <li><a href="/wiki/4-Hydroxytestosterone" title="4-Hydroxytestosterone">4-Hydroxytestosterone</a></li> <li><a href="/w/index.php?title=4,17%CE%B1-Dimethyltestosterone&action=edit&redlink=1" class="new" title="4,17α-Dimethyltestosterone (page does not exist)">4,17α-Dimethyltestosterone</a></li> <li><a href="/wiki/5-Androstenedione" title="5-Androstenedione">5-Androstenedione</a></li> <li><a href="/wiki/11-Ketotestosterone" title="11-Ketotestosterone">11-Ketotestosterone</a></li> <li><a href="/wiki/11%CE%B2-Hydroxyandrostenedione" title="11β-Hydroxyandrostenedione">11β-Hydroxyandrostenedione</a></li> <li><a href="/wiki/Adrenosterone" title="Adrenosterone">Adrenosterone (11-ketoandrostenedione, 11-oxoandrostenedione)</a></li> <li><a href="/wiki/5-Androstenediol" class="mw-redirect" title="5-Androstenediol">Androstenediol (5-androstenediol)</a> <ul><li><a href="/wiki/Androstenediol_3%CE%B2-acetate" title="Androstenediol 3β-acetate">Androstenediol 3β-acetate</a></li> <li><a href="/wiki/Androstenediol_17%CE%B2-acetate" title="Androstenediol 17β-acetate">Androstenediol 17β-acetate</a></li> <li><a href="/wiki/Androstenediol_diacetate" title="Androstenediol diacetate">Androstenediol diacetate</a></li> <li><a href="/wiki/Androstenediol_dipropionate" title="Androstenediol dipropionate">Androstenediol dipropionate</a></li></ul></li> <li><a href="/wiki/4-Androstenedione" class="mw-redirect" title="4-Androstenedione">Androstenedione (4-androstenedione)</a></li> <li><a href="/wiki/Atamestane" title="Atamestane">Atamestane</a></li> <li><a href="/wiki/Boldenone" title="Boldenone">Boldenone</a> <ul><li><a href="/wiki/Boldenone_undecylenate" title="Boldenone undecylenate">Boldenone undecylenate</a></li></ul></li> <li><a href="/wiki/Boldione" title="Boldione">Boldione (1,4-androstadienedione)</a></li> <li><a href="/wiki/Clostebol" title="Clostebol">Clostebol</a> <ul><li><a href="/wiki/Clostebol_acetate" title="Clostebol acetate">Clostebol acetate</a></li> <li><a href="/wiki/Clostebol_caproate" title="Clostebol caproate">Clostebol caproate</a></li> <li><a href="/wiki/Clostebol_propionate" title="Clostebol propionate">Clostebol propionate</a></li></ul></li> <li><a href="/wiki/Cloxotestosterone" title="Cloxotestosterone">Cloxotestosterone</a> <ul><li><a href="/wiki/Cloxotestosterone_acetate" title="Cloxotestosterone acetate">Cloxotestosterone acetate</a></li></ul></li> <li><a href="/wiki/Dehydroandrosterone" title="Dehydroandrosterone">Dehydroandrosterone</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA (androstenolone, prasterone; 5-DHEA)</a> <ul><li><a href="/wiki/Prasterone_enanthate" title="Prasterone enanthate">DHEA enanthate (prasterone enanthate)</a></li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA sulfate</a></li></ul></li> <li><a href="/wiki/Exemestane" title="Exemestane">Exemestane</a></li> <li><a href="/wiki/Formestane" title="Formestane">Formestane</a></li> <li><a href="/wiki/Plomestane" title="Plomestane">Plomestane</a></li> <li><a href="/wiki/Quinbolone" title="Quinbolone">Quinbolone</a></li> <li><a href="/wiki/Silandrone" title="Silandrone">Silandrone</a></li> <li><a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">Testosterone</a><sup>#</sup> (<a href="/wiki/Testosterone/dutasteride" title="Testosterone/dutasteride">+dutasteride</a>) <ul><li><a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">Testosterone esters</a></li> <li><a href="/wiki/Polytestosterone_phloretin_phosphate" title="Polytestosterone phloretin phosphate">Polytestosterone phloretin phosphate</a></li></ul></li></ul> <ul><li><i>5α-Dihydrotestosterone derivatives:</i> <a href="/wiki/1-Androstenediol" title="1-Androstenediol">1-Androstenediol</a></li> <li><a href="/wiki/1-Androstenedione" title="1-Androstenedione">1-Androstenedione</a></li> <li><a href="/wiki/1-Androsterone" title="1-Androsterone">1-Androsterone (1-andro, 1-DHEA)</a></li> <li><a href="/wiki/1-Testosterone" title="1-Testosterone">1-Testosterone</a></li> <li><a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/wiki/5%CE%B1-Androst-2-en-17-one" class="mw-redirect" title="5α-Androst-2-en-17-one">5α-Androst-2-en-17-one</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/11-Ketodihydrotestosterone" title="11-Ketodihydrotestosterone">11-Ketodihydrotestosterone</a></li> <li><a href="/wiki/Androsterone" title="Androsterone">Androsterone</a></li> <li><a href="/wiki/Bolazine" title="Bolazine">Bolazine</a> <ul><li><a href="/wiki/Bolazine_capronate" title="Bolazine capronate">Bolazine capronate</a></li></ul></li> <li><a href="/w/index.php?title=Dihydroethyltestosterone&action=edit&redlink=1" class="new" title="Dihydroethyltestosterone (page does not exist)">Dihydroethyltestosterone</a></li> <li><a href="/wiki/Dihydrofluoxymesterone" title="Dihydrofluoxymesterone">Dihydrofluoxymesterone</a></li> <li><a href="/w/index.php?title=Dihydromethylandrostenediol&action=edit&redlink=1" class="new" title="Dihydromethylandrostenediol (page does not exist)">Dihydromethylandrostenediol</a></li> <li><a href="/wiki/Dihydrotestosterone" title="Dihydrotestosterone">Dihydrotestosterone (DHT)</a> (<a href="/wiki/Androstanolone" title="Androstanolone">androstanolone, stanolone</a>) <ul><li><a href="/wiki/List_of_androgen_esters#Dihydrotestosterone_esters" title="List of androgen esters">Dihydrotestosterone esters</a></li></ul></li> <li><a href="/wiki/Drostanolone" title="Drostanolone">Drostanolone</a> <ul><li><a href="/wiki/Drostanolone_propionate" title="Drostanolone propionate">Drostanolone propionate</a></li></ul></li> <li><a href="/wiki/Epiandrosterone" title="Epiandrosterone">Epiandrosterone</a></li> <li><a href="/wiki/Epitiostanol" title="Epitiostanol">Epitiostanol</a></li> <li><a href="/wiki/Mepitiostane" title="Mepitiostane">Mepitiostane</a></li> <li><a href="/wiki/Mesabolone" title="Mesabolone">Mesabolone</a></li> <li><a href="/wiki/Mesterolone" title="Mesterolone">Mesterolone</a> <ul><li><a href="/wiki/Mesterolone_cipionate" title="Mesterolone cipionate">Mesterolone cipionate</a></li></ul></li> <li><a href="/wiki/Methyldiazinol" title="Methyldiazinol">Methyldiazinol</a></li> <li><a href="/wiki/Nisterime" title="Nisterime">Nisterime</a> <ul><li><a href="/wiki/Nisterime_acetate" title="Nisterime acetate">Nisterime acetate</a></li></ul></li> <li><a href="/wiki/Prostanozol" title="Prostanozol">Prostanozol</a></li> <li><a href="/wiki/Stenbolone" title="Stenbolone">Stenbolone</a> <ul><li><a href="/wiki/Stenbolone_acetate" title="Stenbolone acetate">Stenbolone acetate</a></li></ul></li> <li><a href="/wiki/Testifenon" title="Testifenon">Testifenon (testiphenon, testiphenone)</a></li></ul> <ul><li><i>19-Nortestosterone derivatives:</i> <a href="/wiki/7%CE%B1-Methyl-19-norandrostenedione" title="7α-Methyl-19-norandrostenedione">7α-Methyl-19-norandrostenedione (MENT dione, trestione)</a></li> <li><a href="/wiki/11%CE%B2-Methyl-19-nortestosterone" title="11β-Methyl-19-nortestosterone">11β-Methyl-19-nortestosterone</a> <ul><li><a href="/wiki/11%CE%B2-Methyl-19-nortestosterone_dodecylcarbonate" title="11β-Methyl-19-nortestosterone dodecylcarbonate">11β-Methyl-19-nortestosterone dodecylcarbonate</a></li></ul></li> <li><a href="/wiki/19-Nor-5-androstenediol" title="19-Nor-5-androstenediol">19-Nor-5-androstenediol</a></li> <li><a href="/wiki/19-Nor-5-androstenedione" title="19-Nor-5-androstenedione">19-Nor-5-androstenedione</a></li> <li><a href="/wiki/19-Nordehydroepiandrosterone" title="19-Nordehydroepiandrosterone">19-Nordehydroepiandrosterone</a></li> <li><a href="/wiki/Bolandiol" title="Bolandiol">Bolandiol</a> <ul><li><a href="/wiki/Bolandiol_dipropionate" title="Bolandiol dipropionate">Bolandiol dipropionate</a></li></ul></li> <li><a href="/wiki/Bolandione" title="Bolandione">Bolandione (19-nor-4-androstenedione)</a></li> <li><a href="/wiki/Bolmantalate" title="Bolmantalate">Bolmantalate (nandrolone adamantoate)</a></li> <li><a href="/wiki/Dienedione" title="Dienedione">Dienedione</a></li> <li><a href="/wiki/Dienolone" title="Dienolone">Dienolone</a></li> <li><a href="/wiki/Dimethandrolone" title="Dimethandrolone">Dimethandrolone</a> <ul><li><a href="/wiki/Dimethandrolone_buciclate" title="Dimethandrolone buciclate">Dimethandrolone buciclate</a></li> <li><a href="/wiki/Dimethandrolone_dodecylcarbonate" title="Dimethandrolone dodecylcarbonate">Dimethandrolone dodecylcarbonate</a></li> <li><a href="/wiki/Dimethandrolone_undecanoate" title="Dimethandrolone undecanoate">Dimethandrolone undecanoate</a></li></ul></li> <li><a href="/wiki/LS-1727" title="LS-1727">LS-1727 (nandrolone 17β-<i>N</i>-(2-chloroethyl)-<i>N</i>-nitrosocarbamate)</a></li> <li><a href="/wiki/Methoxydienone" title="Methoxydienone">Methoxydienone (methoxygonadiene)</a></li> <li><a href="/wiki/Nandrolone" title="Nandrolone">Nandrolone</a> <ul><li><a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">Nandrolone esters</a></li></ul></li> <li><a href="/wiki/Norclostebol" title="Norclostebol">Norclostebol</a> <ul><li><a href="/wiki/Norclostebol_acetate" title="Norclostebol acetate">Norclostebol acetate</a></li></ul></li> <li><a href="/wiki/Normethandrone" title="Normethandrone">Normethandrone (methylestrenolone, normethisterone)</a></li> <li><a href="/wiki/Oxabolone" title="Oxabolone">Oxabolone</a> <ul><li><a href="/wiki/Oxabolone_cipionate" title="Oxabolone cipionate">Oxabolone cipionate (oxabolone cypionate)</a></li></ul></li> <li><a href="/wiki/Trenbolone" title="Trenbolone">Trenbolone</a> <ul><li><a href="/wiki/Trenbolone_acetate" title="Trenbolone acetate">Trenbolone acetate</a></li> <li><a href="/wiki/Trenbolone_enanthate" title="Trenbolone enanthate">Trenbolone enanthate</a></li> <li><a href="/wiki/Trenbolone_hexahydrobenzylcarbonate" title="Trenbolone hexahydrobenzylcarbonate">Trenbolone hexahydrobenzylcarbonate</a></li> <li><a href="/wiki/Trenbolone_undecanoate" title="Trenbolone undecanoate">Trenbolone undecanoate</a></li></ul></li> <li><a href="/wiki/Trendione" title="Trendione">Trendione</a></li> <li><a href="/wiki/Trestolone" title="Trestolone">Trestolone (MENT)</a> <ul><li><a href="/wiki/Trestolone_acetate" title="Trestolone acetate">Trestolone acetate</a></li> <li><a href="/wiki/Trestolone_enanthate" title="Trestolone enanthate">Trestolone enanthate</a></li></ul></li></ul> <ul><li><i>5α-Dihydro-19-nortestosterone derivatives:</i> <a href="/wiki/5%CE%B1-Dihydronandrolone" title="5α-Dihydronandrolone">5α-Dihydronandrolone</a></li> <li><a href="/w/index.php?title=5%CE%B1-Dihydrotrestolone&action=edit&redlink=1" class="new" title="5α-Dihydrotrestolone (page does not exist)">5α-Dihydrotrestolone</a></li> <li><a href="/wiki/19-Norandrosterone" title="19-Norandrosterone">19-Norandrosterone</a></li></ul> <ul><li><i>17α-Alkylated testosterone derivatives:</i> <a href="/wiki/Bolasterone" title="Bolasterone">Bolasterone</a></li> <li><a href="/wiki/Calusterone" title="Calusterone">Calusterone</a></li> <li><a href="/wiki/Chlorodehydromethylandrostenediol" title="Chlorodehydromethylandrostenediol">Chlorodehydromethylandrostenediol (CDMA)</a></li> <li><a href="/wiki/Chlorodehydromethyltestosterone" title="Chlorodehydromethyltestosterone">Chlorodehydromethyltestosterone (CDMT)</a></li> <li><a href="/wiki/Chloromethylandrostenediol" title="Chloromethylandrostenediol">Chloromethylandrostenediol (CMA)</a></li> <li><a href="/wiki/Enestebol" title="Enestebol">Enestebol</a></li> <li><a href="/wiki/Ethyltestosterone" title="Ethyltestosterone">Ethyltestosterone</a></li> <li><a href="/wiki/Fluoxymesterone" title="Fluoxymesterone">Fluoxymesterone</a></li> <li><a href="/wiki/Formebolone" title="Formebolone">Formebolone</a></li> <li><a href="/wiki/Hydroxystenozole" title="Hydroxystenozole">Hydroxystenozole</a></li> <li><a href="/wiki/Metandienone" title="Metandienone">Metandienone (methandrostenolone)</a></li> <li><a href="/wiki/Methandriol" title="Methandriol">Methandriol (methylandrostenediol)</a> <ul><li><a href="/wiki/Methandriol_bisenanthoyl_acetate" title="Methandriol bisenanthoyl acetate">Methandriol bisenanthoyl acetate</a></li> <li><a href="/wiki/Methandriol_diacetate" title="Methandriol diacetate">Methandriol diacetate</a></li> <li><a href="/wiki/Methandriol_dipropionate" title="Methandriol dipropionate">Methandriol dipropionate</a></li> <li><a href="/wiki/Methandriol_propionate" title="Methandriol propionate">Methandriol propionate</a></li></ul></li> <li><a href="/wiki/Methylclostebol" title="Methylclostebol">Methylclostebol (chloromethyltestosterone)</a></li> <li><a href="/wiki/Methyltestosterone" title="Methyltestosterone">Methyltestosterone</a> (<a href="/wiki/Esterified_estrogens/methyltestosterone" title="Esterified estrogens/methyltestosterone">+esterified estrogens</a>) <ul><li><a href="/wiki/Methyltestosterone_3-hexyl_ether" title="Methyltestosterone 3-hexyl ether">Methyltestosterone 3-hexyl ether</a></li></ul></li> <li><a href="/wiki/Oxymesterone" title="Oxymesterone">Oxymesterone</a></li> <li><a href="/wiki/Penmesterol" title="Penmesterol">Penmesterol</a></li> <li><a href="/wiki/Tiomesterone" title="Tiomesterone">Tiomesterone</a></li></ul> <ul><li><i>17α-Alkylated 5α-dihydrotestosterone derivatives:</i> <a href="/wiki/Androisoxazole" title="Androisoxazole">Androisoxazole</a></li> <li><a href="/wiki/Desoxymethyltestosterone" title="Desoxymethyltestosterone">Desoxymethyltestosterone</a></li> <li><a href="/wiki/Furazabol" title="Furazabol">Furazabol</a></li> <li><a href="/wiki/Mebolazine" title="Mebolazine">Mebolazine (dimethazine)</a></li> <li><a href="/wiki/Mestanolone" title="Mestanolone">Mestanolone</a></li> <li><a href="/wiki/Metenolone" title="Metenolone">Metenolone</a> <ul><li><a href="/wiki/Metenolone_acetate" title="Metenolone acetate">Metenolone acetate</a></li> <li><a href="/wiki/Metenolone_enanthate" title="Metenolone enanthate">Metenolone enanthate</a></li></ul></li> <li><a href="/wiki/Methasterone" title="Methasterone">Methasterone</a></li> <li><a href="/wiki/Methyl-1-testosterone" title="Methyl-1-testosterone">Methyl-1-testosterone</a></li> <li><a href="/wiki/Methylepitiostanol" title="Methylepitiostanol">Methylepitiostanol</a></li> <li><a href="/wiki/Methylstenbolone" title="Methylstenbolone">Methylstenbolone</a></li> <li><a href="/wiki/Oxandrolone" title="Oxandrolone">Oxandrolone</a></li> <li><a href="/wiki/Oxymetholone" title="Oxymetholone">Oxymetholone</a></li> <li><a href="/wiki/Stanozolol" title="Stanozolol">Stanozolol</a></li></ul> <ul><li><i>17α-Alkylated 19-nortestosterone derivatives:</i> <a href="/wiki/Bolenol" title="Bolenol">Bolenol</a></li> <li><a href="/wiki/Dimethyldienolone" title="Dimethyldienolone">Dimethyldienolone</a></li> <li><a href="/wiki/Dimethyltrienolone" title="Dimethyltrienolone">Dimethyltrienolone</a></li> <li><a href="/wiki/Ethyldienolone" title="Ethyldienolone">Ethyldienolone</a></li> <li><a href="/wiki/Ethylestrenol" title="Ethylestrenol">Ethylestrenol</a></li> <li><a href="/wiki/Methyldienolone" title="Methyldienolone">Methyldienolone</a></li> <li><a href="/wiki/Methylhydroxynandrolone" title="Methylhydroxynandrolone">Methylhydroxynandrolone (MOHN, MHN)</a></li> <li><a href="/wiki/Metribolone" title="Metribolone">Metribolone</a></li> <li><a href="/wiki/Mibolerone" title="Mibolerone">Mibolerone</a></li> <li><a href="/wiki/Norboletone" title="Norboletone">Norboletone</a></li> <li><a href="/wiki/Norethandrolone" title="Norethandrolone">Norethandrolone</a></li> <li><a href="/wiki/Propetandrol" title="Propetandrol">Propetandrol</a></li> <li><a href="/wiki/RU-2309" title="RU-2309">RU-2309</a></li> <li><a href="/wiki/Tetrahydrogestrinone" title="Tetrahydrogestrinone">Tetrahydrogestrinone</a></li></ul> <ul><li><i>17α-Alkylated 5α-dihydro-19-nortestosterone derivatives:</i> <a href="/wiki/5%CE%B1-Dihydronorethandrolone" title="5α-Dihydronorethandrolone">5α-Dihydronorethandrolone</a></li> <li><a href="/wiki/5%CE%B1-Dihydronormethandrone" title="5α-Dihydronormethandrone">5α-Dihydronormethandrone</a></li></ul> <ul><li><i>17α-Vinyltestosterone derivatives:</i> <a href="/wiki/Norvinisterone" title="Norvinisterone">Norvinisterone (vinylnortestosterone)</a></li></ul> <ul><li><i>17α-Vinyl-19-nortestosterone derivatives:</i> <a href="/wiki/Vinyltestosterone" title="Vinyltestosterone">Vinyltestosterone</a></li></ul> <ul><li><i>17α-Ethynyltestosterone derivatives:</i> <a 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><i>5α-Dihydro-17α-ethynyltestosterone derivatives:</i> <a href="/wiki/17%CE%B1-Ethynyl-3%CE%B1-androstanediol" title="17α-Ethynyl-3α-androstanediol">17α-Ethynyl-3α-androstanediol</a></li> <li><a href="/wiki/17%CE%B1-Ethynyl-3%CE%B2-androstanediol" title="17α-Ethynyl-3β-androstanediol">17α-Ethynyl-3β-androstanediol</a></li> <li><a href="/wiki/Dihydroethisterone" class="mw-redirect" title="Dihydroethisterone">Dihydroethisterone</a></li></ul> <ul><li><i>17α-Ethynyl-19-nortestosterone derivatives:</i> <a href="/wiki/%CE%944-Tibolone" title="Δ4-Tibolone">Δ<sup>4</sup>-Tibolone</a></li> <li><a href="/wiki/Desogestrel" title="Desogestrel">Desogestrel</a></li> <li><a href="/wiki/Etonogestrel" title="Etonogestrel">Etonogestrel</a></li> <li><a href="/wiki/Etynodiol" title="Etynodiol">Etynodiol</a> <ul><li><a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">Etynodiol diacetate</a></li></ul></li> <li><a href="/wiki/Gestodene" title="Gestodene">Gestodene</a></li> <li><a href="/wiki/Gestrinone" title="Gestrinone">Gestrinone</a></li> <li><a href="/wiki/Levonorgestrel" title="Levonorgestrel">Levonorgestrel</a></li> <li><a href="/wiki/Levonorgestrel_ester" class="mw-redirect" title="Levonorgestrel ester">Levonorgestrel esters</a> (e.g., <a href="/wiki/Levonorgestrel_butanoate" title="Levonorgestrel butanoate">levonorgestrel butanoate</a>)</li> <li><a href="/wiki/Lynestrenol" title="Lynestrenol">Lynestrenol</a> <ul><li><a href="/wiki/Lynestrenol_phenylpropionate" title="Lynestrenol phenylpropionate">Lynestrenol phenylpropionate</a></li></ul></li> <li><a href="/wiki/Norethisterone" title="Norethisterone">Norethisterone</a></li> <li><a href="/wiki/Norethisterone_ester" class="mw-redirect" title="Norethisterone ester">Norethisterone esters</a> (e.g., <a href="/wiki/Norethisterone_acetate" title="Norethisterone acetate">norethisterone acetate</a>, <a href="/wiki/Norethisterone_enanthate" title="Norethisterone enanthate">norethisterone enanthate</a>)</li> <li><a href="/wiki/Norgestrel" title="Norgestrel">Norgestrel</a></li> <li><a href="/wiki/Norgestrienone" title="Norgestrienone">Norgestrienone</a></li> <li><a href="/wiki/Quingestanol" title="Quingestanol">Quingestanol</a> <ul><li><a href="/wiki/Quingestanol_acetate" title="Quingestanol acetate">Quingestanol acetate</a></li></ul></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li></ul> <ul><li><i>5α-Dihydro-17α-ethynyl-19-nortestosterone derivatives:</i> <a href="/wiki/5%CE%B1-Dihydrolevonorgestrel" title="5α-Dihydrolevonorgestrel">5α-Dihydrolevonorgestrel</a></li> <li><a href="/wiki/5%CE%B1-Dihydronorethisterone" title="5α-Dihydronorethisterone">5α-Dihydronorethisterone</a></li></ul> <ul><li><i>Progesterone derivatives:</i> <a href="/wiki/6%CE%B1-Methylprogesterone" title="6α-Methylprogesterone">6α-Methylprogesterone</a></li> <li><a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">Medroxyprogesterone acetate</a></li> <li><a href="/wiki/Megestrol_acetate" title="Megestrol acetate">Megestrol acetate</a></li></ul> <ul><li><i>Others/unsorted:</i> <a href="/wiki/3-Keto-5%CE%B1-abiraterone" title="3-Keto-5α-abiraterone">3-Keto-5α-abiraterone</a></li> <li><a href="/wiki/5%CE%B1-Androstane" class="mw-redirect" title="5α-Androstane">5α-Androstane</a></li> <li><a href="/wiki/Alternariol" title="Alternariol">Alternariol</a></li> <li><a href="/wiki/Cl-4AS-1" title="Cl-4AS-1">Cl-4AS-1</a></li> <li><a href="/wiki/Drupanol" title="Drupanol">Drupanol</a></li> <li><a href="/wiki/Trilostane" title="Trilostane">Trilostane</a></li> <li><a href="/wiki/ZM-182345" title="ZM-182345">ZM-182345</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center"><a href="/wiki/Selective_androgen_receptor_modulator" title="Selective androgen receptor modulator"><abbr title="Selective androgen receptor modulator">SARMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Selective androgen receptor modulator</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Nonsteroidal:</i> <a href="/w/index.php?title=198RL26&action=edit&redlink=1" class="new" title="198RL26 (page does not exist)">198RL26</a></li> <li><a href="/wiki/ACP-105" title="ACP-105">ACP-105</a></li> <li><a href="/wiki/AC-262,536" title="AC-262,536">AC-262,536</a></li> <li><a href="/wiki/Acetothiolutamide" title="Acetothiolutamide">Acetothiolutamide</a></li> <li><a href="/wiki/Acetoxolutamide" title="Acetoxolutamide">Acetoxolutamide</a></li> <li><a href="/wiki/Andarine" title="Andarine">Andarine (acetamidoxolutamide, androxolutamide, GTx-007, S-4)</a></li> <li><a href="/wiki/BMS-564,929" title="BMS-564,929">BMS-564,929</a></li> <li><a href="/w/index.php?title=DTIB&action=edit&redlink=1" class="new" title="DTIB (page does not exist)">DTIB</a></li> <li><a href="/wiki/Enobosarm" title="Enobosarm">Enobosarm (ostarine, MK-2866, GTx-024, S-22)</a></li> <li><a href="/w/index.php?title=FTBU-1&action=edit&redlink=1" class="new" title="FTBU-1 (page does not exist)">FTBU-1</a></li> <li><a href="/wiki/GLPG-0492" title="GLPG-0492">GLPG-0492</a></li> <li><a href="/wiki/GSK2881078" title="GSK2881078">GSK2881078</a></li> <li><a href="/wiki/GSK-4336A" title="GSK-4336A">GSK-4336A</a></li> <li><a href="/w/index.php?title=GSK-8698&action=edit&redlink=1" class="new" title="GSK-8698 (page does not exist)">GSK-8698</a></li> <li><a href="/wiki/LG121071" title="LG121071">LG121071 (LGD-121071)</a></li> <li><a href="/wiki/LGD-2226" title="LGD-2226">LGD-2226</a></li> <li><a href="/wiki/LGD-2941" title="LGD-2941">LGD-2941 (LGD-122941)</a></li> <li><a href="/wiki/LGD-3303" title="LGD-3303">LGD-3303</a></li> <li><a href="/wiki/LGD-4033" class="mw-redirect" title="LGD-4033">LGD-4033</a></li> <li><a href="/wiki/LY305" title="LY305">LY305</a></li> <li><a href="/wiki/JNJ-26146900" title="JNJ-26146900">JNJ-26146900</a></li> <li><a href="/wiki/JNJ-28330835" title="JNJ-28330835">JNJ-28330835</a></li> <li><a href="/wiki/JNJ-37654032" title="JNJ-37654032">JNJ-37654032</a></li> <li><a href="/wiki/OPK-88004" title="OPK-88004">OPK-88004 (LY-2452473, TT-701)</a></li> <li><a href="/w/index.php?title=ORM-11984&action=edit&redlink=1" class="new" title="ORM-11984 (page does not exist)">ORM-11984</a></li> <li><a href="/wiki/PF-06260414" title="PF-06260414">PF-06260414</a></li> <li><a href="/w/index.php?title=R-1_(drug)&action=edit&redlink=1" class="new" title="R-1 (drug) (page does not exist)">R-1</a></li> <li><a href="/wiki/RU-59063" title="RU-59063">RU-59063</a></li> <li><a href="/w/index.php?title=S-1_(drug)&action=edit&redlink=1" class="new" title="S-1 (drug) (page does not exist)">S-1</a></li> <li><a href="/wiki/S-23_(drug)" title="S-23 (drug)">S-23</a></li> <li><a href="/wiki/S-40503" title="S-40503">S-40503</a></li> <li><a href="/w/index.php?title=S-101479&action=edit&redlink=1" class="new" title="S-101479 (page does not exist)">S-101479</a></li> <li><a href="/wiki/Vosilasarm" title="Vosilasarm">Vosilasarm</a></li></ul> <ul><li><i>Steroidal:</i> <a href="/w/index.php?title=EM-9017&action=edit&redlink=1" class="new" title="EM-9017 (page does not exist)">EM-9017</a></li> <li><a href="/wiki/MK-0773" title="MK-0773">MK-0773</a></li> <li><a href="/wiki/TFM-4AS-1" title="TFM-4AS-1">TFM-4AS-1</a></li> <li><a href="/wiki/YK-11" title="YK-11">YK-11</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Steroidal:</i> <a href="/wiki/7%CE%B1-Thioprogesterone" title="7α-Thioprogesterone">7α-Thioprogesterone</a></li> <li><a href="/wiki/7%CE%B1-Thiospironolactone" title="7α-Thiospironolactone">7α-Thiospironolactone</a></li> <li><a href="/wiki/7%CE%B1-Thiomethylspironolactone" title="7α-Thiomethylspironolactone">7α-Thiomethylspironolactone</a></li> <li><a href="/wiki/11%CE%B1-Hydroxyprogesterone" title="11α-Hydroxyprogesterone">11α-Hydroxyprogesterone</a></li> <li><a href="/wiki/15%CE%B2-Hydroxycyproterone_acetate" title="15β-Hydroxycyproterone acetate">15β-Hydroxycyproterone acetate</a></li> <li><a href="/wiki/Abiraterone" class="mw-redirect" title="Abiraterone">Abiraterone</a></li> <li><a href="/wiki/Abiraterone_acetate" title="Abiraterone acetate">Abiraterone acetate</a></li> <li><a href="/wiki/Allyltestosterone" title="Allyltestosterone">Allyltestosterone</a></li> <li><a href="/wiki/Benorterone" title="Benorterone">Benorterone</a></li> <li><a href="/wiki/BOMT" title="BOMT">BOMT</a></li> <li><a href="/wiki/Canrenoic_acid" title="Canrenoic acid">Canrenoic acid</a></li> <li><a href="/wiki/Canrenone" title="Canrenone">Canrenone</a></li> <li><a href="/wiki/Chlormadinone_acetate" title="Chlormadinone acetate">Chlormadinone acetate</a></li> <li><a href="/wiki/Clascoterone" title="Clascoterone">Clascoterone</a></li> <li><a href="/wiki/Clometerone" title="Clometerone">Clometerone</a></li> <li><a href="/wiki/Cyproheptadine" title="Cyproheptadine">Cyproheptadine</a></li> <li><a href="/wiki/Cyproterone" title="Cyproterone">Cyproterone</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Delanterone" title="Delanterone">Delanterone</a></li> <li><a href="/wiki/Delmadinone_acetate" title="Delmadinone acetate">Delmadinone acetate</a></li> <li><a href="/wiki/Dicirenone" title="Dicirenone">Dicirenone</a></li> <li><a href="/wiki/Dienogest" title="Dienogest">Dienogest</a></li> <li><a href="/wiki/Drospirenone" title="Drospirenone">Drospirenone</a></li> <li><a href="/wiki/DU-41165" title="DU-41165">DU-41165</a></li> <li><a href="/wiki/Edogestrone" title="Edogestrone">Edogestrone</a></li> <li><a href="/w/index.php?title=EM-4350&action=edit&redlink=1" class="new" title="EM-4350 (page does not exist)">EM-4350</a></li> <li><a href="/wiki/EM-5854" title="EM-5854">EM-5854</a></li> <li><a href="/w/index.php?title=EM-5855&action=edit&redlink=1" class="new" title="EM-5855 (page does not exist)">EM-5855</a></li> <li><a href="/w/index.php?title=EM-6537&action=edit&redlink=1" class="new" title="EM-6537 (page does not exist)">EM-6537</a></li> <li><a href="/wiki/Epitestosterone" title="Epitestosterone">Epitestosterone</a></li> <li><a href="/wiki/Galeterone" title="Galeterone">Galeterone</a></li> <li><a href="/wiki/Guggulsterone" title="Guggulsterone">Guggulsterone</a></li> <li><a href="/w/index.php?title=Ludaterone&action=edit&redlink=1" class="new" title="Ludaterone (page does not exist)">Ludaterone</a></li> <li><a href="/wiki/Medrogestone" title="Medrogestone">Medrogestone</a></li> <li><a href="/wiki/Megestrol_acetate" title="Megestrol acetate">Megestrol acetate</a></li> <li><a href="/wiki/Mespirenone" title="Mespirenone">Mespirenone</a></li> <li><a href="/wiki/Metogest" title="Metogest">Metogest</a></li> <li><a href="/wiki/Mexrenone" title="Mexrenone">Mexrenone</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li> <li><a href="/wiki/Nomegestrol_acetate" title="Nomegestrol acetate">Nomegestrol acetate</a></li> <li><a href="/wiki/Nordinone" title="Nordinone">Nordinone</a></li> <li><a href="/wiki/Osaterone" title="Osaterone">Osaterone</a></li> <li><a href="/wiki/Osaterone_acetate" title="Osaterone acetate">Osaterone acetate</a></li> <li><a href="/wiki/Oxendolone" title="Oxendolone">Oxendolone</a></li> <li><a href="/wiki/Potassium_canrenoate" title="Potassium canrenoate">Potassium canrenoate</a></li> <li><a href="/wiki/Promegestone" title="Promegestone">Promegestone</a></li> <li><a href="/wiki/Prorenone" title="Prorenone">Prorenone</a></li> <li><a href="/wiki/Rosterolone" title="Rosterolone">Rosterolone</a></li> <li><a href="/w/index.php?title=RU-15328&action=edit&redlink=1" class="new" title="RU-15328 (page does not exist)">RU-15328</a></li> <li><a href="/wiki/SC-5233" title="SC-5233">SC-5233 (spirolactone)</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/wiki/Spirorenone" title="Spirorenone">Spirorenone</a></li> <li><a href="/wiki/Spiroxasone" title="Spiroxasone">Spiroxasone</a></li> <li><a href="/wiki/Topterone" title="Topterone">Topterone</a></li> <li><a href="/wiki/Trimegestone" title="Trimegestone">Trimegestone</a></li> <li><a href="/wiki/Trimethyltrienolone" title="Trimethyltrienolone">Trimethyltrienolone (R-2956)</a></li> <li><a href="/wiki/Zanoterone" title="Zanoterone">Zanoterone</a></li></ul> <ul><li><i>Nonsteroidal:</i> <a href="/wiki/5N-Bicalutamide" title="5N-Bicalutamide">5<i>N</i>-Bicalutamide</a></li> <li><a href="/wiki/AA560" title="AA560">AA560</a></li> <li><a href="/w/index.php?title=Antarlide&action=edit&redlink=1" class="new" title="Antarlide (page does not exist)">Antarlides</a></li> <li><a href="/w/index.php?title=Arabilin&action=edit&redlink=1" class="new" title="Arabilin (page does not exist)">Arabilin</a></li> <li><a href="/wiki/Apalutamide" title="Apalutamide">Apalutamide</a></li> <li><a href="/wiki/Atraric_acid" title="Atraric acid">Atraric acid</a></li> <li><a href="/w/index.php?title=AZD-3514&action=edit&redlink=1" class="new" title="AZD-3514 (page does not exist)">AZD-3514</a></li> <li><a href="/wiki/Bakuchiol" title="Bakuchiol">Bakuchiol</a></li> <li><a href="/wiki/Bavdegalutamide" title="Bavdegalutamide">Bavdegalutamide</a></li> <li><a href="/w/index.php?title=BAY-1024767&action=edit&redlink=1" class="new" title="BAY-1024767 (page does not exist)">BAY-1024767</a></li> <li><a href="/wiki/Bicalutamide" title="Bicalutamide">Bicalutamide</a></li> <li><a href="/wiki/Bisphenol" title="Bisphenol">Bisphenols</a> (e.g., <a href="/wiki/Bisphenol_A_diglycidyl_ether" title="Bisphenol A diglycidyl ether">BADGE</a>, <a href="/w/index.php?title=Bisphenol_F_diglycidyl_ether&action=edit&redlink=1" class="new" title="Bisphenol F diglycidyl ether (page does not exist)">BFDGE</a>, <a href="/wiki/Bisphenol_A" title="Bisphenol A">bisphenol A</a>, <a href="/wiki/Bisphenol_F" title="Bisphenol F">bisphenol F</a>, <a href="/wiki/Bisphenol_S" title="Bisphenol S">bisphenol S</a>)</li> <li><a href="/w/index.php?title=BMS-501949&action=edit&redlink=1" class="new" title="BMS-501949 (page does not exist)">BMS-501949</a></li> <li><a href="/w/index.php?title=BMS-570511&action=edit&redlink=1" class="new" title="BMS-570511 (page does not exist)">BMS-570511</a></li> <li><a href="/wiki/BMS-641988" title="BMS-641988">BMS-641988</a></li> <li><a href="/w/index.php?title=CH5137291&action=edit&redlink=1" class="new" title="CH5137291 (page does not exist)">CH5137291</a></li> <li><a href="/wiki/Cimetidine" title="Cimetidine">Cimetidine</a></li> <li><a href="/wiki/Cioteronel" title="Cioteronel">Cioteronel</a></li> <li><a href="/wiki/Cyanonilutamide" title="Cyanonilutamide">Cyanonilutamide</a></li> <li><a href="/wiki/Darolutamide" title="Darolutamide">Darolutamide</a></li> <li><a href="/wiki/DDT" title="DDT">DDT</a> (via metabolite <a href="/wiki/Dichlorodiphenyldichloroethylene" title="Dichlorodiphenyldichloroethylene">p,p’-DDE</a>)</li> <li><a href="/wiki/Dieldrin" title="Dieldrin">Dieldrin</a></li> <li><a href="/wiki/DIMP_(antiandrogen)" title="DIMP (antiandrogen)">DIMP</a></li> <li><a href="/wiki/Endosulfan" title="Endosulfan">Endosulfan</a></li> <li><a href="/wiki/Enzalutamide" title="Enzalutamide">Enzalutamide</a></li> <li><a href="/wiki/EPI-001" title="EPI-001">EPI-001</a></li> <li><a href="/wiki/Fenarimol" title="Fenarimol">Fenarimol</a></li> <li><a href="/wiki/Flutamide" title="Flutamide">Flutamide</a></li> <li><a href="/wiki/Hydroxyflutamide" title="Hydroxyflutamide">Hydroxyflutamide</a></li> <li><a href="/wiki/Inocoterone" title="Inocoterone">Inocoterone</a></li> <li><a href="/wiki/Inocoterone_acetate" title="Inocoterone acetate">Inocoterone acetate</a></li> <li><a href="/wiki/Ketoconazole" title="Ketoconazole">Ketoconazole</a></li> <li><a href="/wiki/Ketodarolutamide" title="Ketodarolutamide">Ketodarolutamide</a></li> <li><a href="/wiki/Lavender_oil" title="Lavender oil">Lavender oil</a></li> <li><a href="/w/index.php?title=LG-105&action=edit&redlink=1" class="new" title="LG-105 (page does not exist)">LG-105</a></li> <li><a href="/wiki/LG-120907" title="LG-120907">LG-120907</a></li> <li><a href="/w/index.php?title=LGD-1331&action=edit&redlink=1" class="new" title="LGD-1331 (page does not exist)">LGD-1331</a></li> <li><a href="/wiki/Linuron" title="Linuron">Linuron</a></li> <li><a href="/wiki/Masofaniten" title="Masofaniten">Masofaniten</a></li> <li><a href="/wiki/Methiocarb" title="Methiocarb">Methiocarb</a></li> <li><a href="/w/index.php?title=N-Butylbenzenesulfonamide&action=edit&redlink=1" class="new" title="N-Butylbenzenesulfonamide (page does not exist)"><i>N</i>-Butylbenzenesulfonamide</a></li> <li><a href="/wiki/N-Desmethylapalutamide" title="N-Desmethylapalutamide"><i>N</i>-Desmethylapalutamide</a></li> <li><a href="/wiki/N-Desmethylenzalutamide" title="N-Desmethylenzalutamide"><i>N</i>-Desmethylenzalutamide</a></li> <li><a href="/wiki/Nilutamide" title="Nilutamide">Nilutamide</a></li> <li><a href="/w/index.php?title=ONC1-13B&action=edit&redlink=1" class="new" title="ONC1-13B (page does not exist)">ONC1-13B</a></li> <li><a href="/wiki/Pentomone" title="Pentomone">Pentomone</a></li> <li><a href="/w/index.php?title=PF-998425&action=edit&redlink=1" class="new" title="PF-998425 (page does not exist)">PF-998425</a></li> <li><a href="/wiki/Phenothrin" title="Phenothrin">Phenothrin</a></li> <li><a href="/wiki/Prochloraz" title="Prochloraz">Prochloraz</a></li> <li><a href="/wiki/Procymidone" title="Procymidone">Procymidone</a></li> <li><a href="/wiki/Proxalutamide" title="Proxalutamide">Proxalutamide</a></li> <li><a href="/wiki/Pyrilutamide" title="Pyrilutamide">Pyrilutamide</a></li> <li><a href="/wiki/Ralaniten" title="Ralaniten">Ralaniten (EPI-002)</a></li> <li><a href="/wiki/Ralaniten_acetate" title="Ralaniten acetate">Ralaniten acetate (EPI-506)</a></li> <li><a href="/wiki/RD-162" title="RD-162">RD-162</a></li> <li><a href="/wiki/Rezvilutamide" title="Rezvilutamide">Rezvilutamide</a></li> <li><a href="/w/index.php?title=Ro_2-7239&action=edit&redlink=1" class="new" title="Ro 2-7239 (page does not exist)">Ro 2-7239</a></li> <li><a href="/w/index.php?title=Ro_5-2537&action=edit&redlink=1" class="new" title="Ro 5-2537 (page does not exist)">Ro 5-2537</a></li> <li><a href="/wiki/RU-22930" title="RU-22930">RU-22930</a></li> <li><a href="/wiki/RU-56187" title="RU-56187">RU-56187</a></li> <li><a href="/wiki/RU-57073" title="RU-57073">RU-57073</a></li> <li><a href="/wiki/RU-58642" title="RU-58642">RU-58642</a></li> <li><a href="/wiki/RU-58841" title="RU-58841">RU-58841</a></li> <li><a href="/wiki/Seviteronel" title="Seviteronel">Seviteronel</a></li> <li><a href="/wiki/Thalidomide" title="Thalidomide">Thalidomide</a></li> <li><a href="/wiki/Topilutamide" title="Topilutamide">Topilutamide (fluridil)</a></li> <li><a href="/wiki/Valproic_acid" class="mw-redirect" title="Valproic acid">Valproic acid</a></li> <li><a href="/wiki/Vinclozolin" title="Vinclozolin">Vinclozolin</a></li> <li><a href="/w/index.php?title=YM-580&action=edit&redlink=1" class="new" title="YM-580 (page does not exist)">YM-580</a></li> <li><a href="/w/index.php?title=YM-92088&action=edit&redlink=1" class="new" title="YM-92088 (page does not exist)">YM-92088</a></li> <li><a href="/w/index.php?title=YM-175735&action=edit&redlink=1" class="new" title="YM-175735 (page does not exist)">YM-175735</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/GPRC6A" title="GPRC6A">GPRC6A</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;">Agonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cation" class="mw-redirect" title="Cation">Cations</a> (incl. <a href="/wiki/Aluminium" title="Aluminium">aluminium</a>, <a href="/wiki/Calcium" title="Calcium">calcium</a>, <a href="/wiki/Gadolinium" title="Gadolinium">gadolinium</a>, <a href="/wiki/Magnesium" title="Magnesium">magnesium</a>, <a href="/wiki/Strontium" title="Strontium">strontium</a>, <a href="/wiki/Zinc" title="Zinc">zinc</a>)</li> <li><a href="/wiki/Dehydroandrosterone" title="Dehydroandrosterone">Dehydroandrosterone</a></li> <li><a href="/wiki/Dihydrotestosterone" title="Dihydrotestosterone">Dihydrotestosterone</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/wiki/Amino_acid" title="Amino acid"><small>L</small>-α-Amino acids</a> (incl. <a href="/wiki/Arginine" title="Arginine"><small>L</small>-arginine</a>, <a href="/wiki/Lysine" title="Lysine"><small>L</small>-lysine</a>, <a href="/wiki/Ornithine" title="Ornithine"><small>L</small>-ornithine</a>)</li> <li><a href="/wiki/Osteocalcin" title="Osteocalcin">Osteocalcin</a></li> <li><a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin"><abbr title="Sex hormone-binding globulin">SHBG</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Sex hormone-binding globulin</span></li> <li><a href="/wiki/Testosterone" title="Testosterone">Testosterone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Androgens_and_antiandrogens" title="Template:Androgens and antiandrogens">Androgens and antiandrogens</a></dd> <dd><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators">Estrogen receptor modulators</a></dd> <dd><a href="/wiki/Template:Progesterone_receptor_modulators" title="Template:Progesterone receptor modulators">Progesterone receptor modulators</a></dd> <dd><a href="/wiki/List_of_androgens_and_anabolic_steroids" title="List of androgens and anabolic steroids">List of androgens and anabolic steroids</a></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Estrogen_receptor_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Estrogen_receptor_modulators" title="Template talk:Estrogen receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Estrogen_receptor_modulators" title="Special:EditPage/Template:Estrogen receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Estrogen_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor">Estrogen receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Steroidal:</i> <a href="/wiki/2-Hydroxyestradiol" title="2-Hydroxyestradiol">2-Hydroxyestradiol</a></li> <li><a href="/wiki/2-Hydroxyestrone" title="2-Hydroxyestrone">2-Hydroxyestrone</a></li> <li><a href="/wiki/3-Methyl-19-methyleneandrosta-3,5-dien-17%CE%B2-ol" title="3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol">3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol</a></li> <li><a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/w/index.php?title=3%CE%B1,5%CE%B1-Dihydrolevonorgestrel&action=edit&redlink=1" class="new" title="3α,5α-Dihydrolevonorgestrel (page does not exist)">3α,5α-Dihydrolevonorgestrel</a></li> <li><a href="/w/index.php?title=3%CE%B2,5%CE%B1-Dihydrolevonorgestrel&action=edit&redlink=1" class="new" title="3β,5α-Dihydrolevonorgestrel (page does not exist)">3β,5α-Dihydrolevonorgestrel</a></li> <li><a href="/wiki/3%CE%B1-Hydroxytibolone" title="3α-Hydroxytibolone">3α-Hydroxytibolone</a></li> <li><a href="/wiki/3%CE%B2-Hydroxytibolone" title="3β-Hydroxytibolone">3β-Hydroxytibolone</a></li> <li><a href="/wiki/3%CE%B2-Androstanediol" title="3β-Androstanediol">3β-Androstanediol</a></li> <li><a href="/wiki/4-Androstenediol" title="4-Androstenediol">4-Androstenediol</a></li> <li><a href="/wiki/4-Androstenedione" class="mw-redirect" title="4-Androstenedione">4-Androstenedione</a></li> <li><a href="/wiki/4-Fluoroestradiol" title="4-Fluoroestradiol">4-Fluoroestradiol</a></li> <li><a href="/wiki/4-Hydroxyestradiol" title="4-Hydroxyestradiol">4-Hydroxyestradiol</a></li> <li><a href="/wiki/4-Hydroxyestrone" title="4-Hydroxyestrone">4-Hydroxyestrone</a></li> <li><a href="/wiki/4-Methoxyestradiol" title="4-Methoxyestradiol">4-Methoxyestradiol</a></li> <li><a href="/wiki/4-Methoxyestrone" title="4-Methoxyestrone">4-Methoxyestrone</a></li> <li><a href="/wiki/5-Androstenediol" class="mw-redirect" title="5-Androstenediol">5-Androstenediol</a></li> <li><a href="/wiki/7-Keto-DHEA" title="7-Keto-DHEA">7-Oxo-DHEA</a></li> <li><a href="/wiki/7%CE%B1-Hydroxy-DHEA" title="7α-Hydroxy-DHEA">7α-Hydroxy-DHEA</a></li> <li><a href="/wiki/7%CE%B1-Methylestradiol" title="7α-Methylestradiol">7α-Methylestradiol</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/8,9-Dehydroestradiol" title="8,9-Dehydroestradiol">8,9-Dehydroestradiol</a></li> <li><a href="/wiki/8,9-Dehydroestrone" title="8,9-Dehydroestrone">8,9-Dehydroestrone</a></li> <li><a href="/wiki/8%CE%B2-VE2" title="8β-VE2">8β-VE2</a></li> <li><a href="/wiki/10%CE%B2,17%CE%B2-Dihydroxyestra-1,4-dien-3-one" title="10β,17β-Dihydroxyestra-1,4-dien-3-one">10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)</a></li> <li><a href="/wiki/11%CE%B2-Chloromethylestradiol" title="11β-Chloromethylestradiol">11β-Chloromethylestradiol</a></li> <li><a href="/wiki/11%CE%B2-Methoxyestradiol" title="11β-Methoxyestradiol">11β-Methoxyestradiol</a></li> <li><a href="/wiki/15%CE%B1-Hydroxyestradiol" title="15α-Hydroxyestradiol">15α-Hydroxyestradiol</a></li> <li><a href="/wiki/16-Ketoestradiol" title="16-Ketoestradiol">16-Ketoestradiol</a></li> <li><a href="/wiki/16-Ketoestrone" title="16-Ketoestrone">16-Ketoestrone</a></li> <li><a href="/wiki/16%CE%B1-Fluoroestradiol" class="mw-redirect" title="16α-Fluoroestradiol">16α-Fluoroestradiol</a></li> <li><a href="/wiki/16%CE%B1-Hydroxy-DHEA" title="16α-Hydroxy-DHEA">16α-Hydroxy-DHEA</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyestrone" title="16α-Hydroxyestrone">16α-Hydroxyestrone</a></li> <li><a href="/wiki/16%CE%B1-Iodoestradiol" class="mw-redirect" title="16α-Iodoestradiol">16α-Iodoestradiol</a></li> <li><a href="/wiki/16%CE%B1-LE2" title="16α-LE2">16α-LE2</a></li> <li><a href="/wiki/16%CE%B2-Hydroxyestrone" title="16β-Hydroxyestrone">16β-Hydroxyestrone</a></li> <li><a href="/wiki/16%CE%B2,17%CE%B1-Epiestriol" title="16β,17α-Epiestriol">16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)</a></li> <li><a href="/wiki/17%CE%B1-Estradiol" title="17α-Estradiol">17α-Estradiol</a> (<a href="/wiki/Alfatradiol" title="Alfatradiol">alfatradiol</a>)</li> <li><a href="/wiki/17%CE%B1-Dihydroequilenin" title="17α-Dihydroequilenin">17α-Dihydroequilenin</a></li> <li><a href="/wiki/17%CE%B1-Dihydroequilin" title="17α-Dihydroequilin">17α-Dihydroequilin</a></li> <li><a href="/wiki/17%CE%B1-Epiestriol" title="17α-Epiestriol">17α-Epiestriol (16α-hydroxy-17α-estradiol)</a></li> <li><a href="/wiki/17%CE%B1-Ethynyl-3%CE%B1-androstanediol" title="17α-Ethynyl-3α-androstanediol">17α-Ethynyl-3α-androstanediol</a></li> <li><a href="/wiki/17%CE%B1-Ethynyl-3%CE%B2-androstanediol" title="17α-Ethynyl-3β-androstanediol">17α-Ethynyl-3β-androstanediol</a></li> <li><a href="/wiki/17%CE%B2-Dihydroequilenin" title="17β-Dihydroequilenin">17β-Dihydroequilenin</a></li> <li><a href="/wiki/17%CE%B2-Dihydroequilin" title="17β-Dihydroequilin">17β-Dihydroequilin</a></li> <li><a href="/wiki/17%CE%B2-Methyl-17%CE%B1-dihydroequilenin" title="17β-Methyl-17α-dihydroequilenin">17β-Methyl-17α-dihydroequilenin</a></li> <li><a href="/wiki/Abiraterone" class="mw-redirect" title="Abiraterone">Abiraterone</a></li> <li><a href="/wiki/Abiraterone_acetate" title="Abiraterone acetate">Abiraterone acetate</a></li> <li><a href="/wiki/Alestramustine" title="Alestramustine">Alestramustine</a></li> <li><a href="/wiki/Almestrone" title="Almestrone">Almestrone</a></li> <li><a href="/wiki/Anabolic_steroid" title="Anabolic steroid">Anabolic steroids</a> (e.g., <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> and <a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">esters</a>, <a href="/wiki/Methyltestosterone" title="Methyltestosterone">methyltestosterone</a>, <a href="/wiki/Metandienone" title="Metandienone">metandienone (methandrostenolone)</a>, <a href="/wiki/Nandrolone" title="Nandrolone">nandrolone</a> and <a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">esters</a>, many others; via estrogenic metabolites)</li> <li><a href="/wiki/Atrimustine" title="Atrimustine">Atrimustine</a></li> <li><a href="/wiki/Bolandiol" title="Bolandiol">Bolandiol</a></li> <li><a href="/wiki/Bolandiol_dipropionate" title="Bolandiol dipropionate">Bolandiol dipropionate</a></li> <li><a href="/wiki/Butolame" title="Butolame">Butolame</a></li> <li><a href="/wiki/Clomestrone" title="Clomestrone">Clomestrone</a></li> <li><a href="/wiki/Cloxestradiol" title="Cloxestradiol">Cloxestradiol</a> <ul><li><a href="/wiki/Cloxestradiol_acetate" title="Cloxestradiol acetate">Cloxestradiol acetate</a></li></ul></li> <li><a href="/wiki/Conjugated_estriol" title="Conjugated estriol">Conjugated estriol</a></li> <li><a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a></li> <li><a href="/wiki/Cyclodiol" title="Cyclodiol">Cyclodiol</a></li> <li><a href="/wiki/Cyclotriol" title="Cyclotriol">Cyclotriol</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA-S</a></li> <li><a href="/wiki/Ent-Estradiol" title="Ent-Estradiol"><i>ent</i>-Estradiol</a></li> <li><a href="/wiki/Epiestriol" title="Epiestriol">Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)</a></li> <li><a href="/wiki/Epimestrol" title="Epimestrol">Epimestrol</a></li> <li><a href="/wiki/Equilenin" title="Equilenin">Equilenin</a></li> <li><a href="/wiki/Equilin" title="Equilin">Equilin</a></li> <li><a href="/wiki/ERA-63" title="ERA-63">ERA-63 (ORG-37663)</a></li> <li><a href="/wiki/Esterified_estrogens" title="Esterified estrogens">Esterified estrogens</a></li> <li><a href="/wiki/Estetrol" title="Estetrol">Estetrol</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estradiol_esters" title="List of estrogen esters">Estradiol esters</a></li> <li><a href="/wiki/Lipoidal_estradiol" title="Lipoidal estradiol">Lipoidal estradiol</a></li> <li><a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">Polyestradiol phosphate</a></li></ul></li> <li><a href="/wiki/Estramustine" title="Estramustine">Estramustine</a></li> <li><a href="/wiki/Estramustine_phosphate" title="Estramustine phosphate">Estramustine phosphate</a></li> <li><a href="/wiki/Estrapronicate" title="Estrapronicate">Estrapronicate</a></li> <li><a href="/wiki/Estrazinol" title="Estrazinol">Estrazinol</a></li> <li><a href="/wiki/Estriol" title="Estriol">Estriol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estriol_esters" title="List of estrogen esters">Estriol esters</a></li> <li><a href="/wiki/Polyestriol_phosphate" title="Polyestriol phosphate">Polyestriol phosphate</a></li></ul></li> <li><a href="/wiki/Estrofurate" title="Estrofurate">Estrofurate</a></li> <li><a href="/wiki/Estrogenic_substances" title="Estrogenic substances">Estrogenic substances</a></li> <li><a href="/wiki/Estromustine" title="Estromustine">Estromustine</a></li> <li><a href="/wiki/Estrone" title="Estrone">Estrone</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estrone_esters" title="List of estrogen esters">Estrone esters</a></li> <li><a href="/wiki/Estrone_methyl_ether" title="Estrone methyl ether">Estrone methyl ether</a></li> <li><a href="/wiki/Estropipate" title="Estropipate">Estropipate</a></li></ul></li> <li><a href="/wiki/Etamestrol" title="Etamestrol">Etamestrol (eptamestrol)</a></li> <li><a href="/wiki/Ethinylandrostenediol" title="Ethinylandrostenediol">Ethinylandrostenediol</a> <ul><li><a href="/wiki/Ethandrostate" title="Ethandrostate">Ethandrostate</a></li></ul></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a> <ul><li><a href="/wiki/Ethinylestradiol_3-benzoate" class="mw-redirect" title="Ethinylestradiol 3-benzoate">Ethinylestradiol 3-benzoate</a></li> <li><a href="/wiki/Ethinylestradiol_sulfonate" title="Ethinylestradiol sulfonate">Ethinylestradiol sulfonate</a></li></ul></li> <li><a href="/wiki/Ethinylestriol" title="Ethinylestriol">Ethinylestriol</a></li> <li><a href="/wiki/Ethylestradiol" title="Ethylestradiol">Ethylestradiol</a></li> <li><a href="/wiki/Etynodiol" title="Etynodiol">Etynodiol</a></li> <li><a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">Etynodiol diacetate</a></li> <li><a href="/wiki/Hexolame" title="Hexolame">Hexolame</a></li> <li><a href="/wiki/Hippulin" title="Hippulin">Hippulin</a></li> <li><a href="/wiki/Hydroxyestrone_diacetate" title="Hydroxyestrone diacetate">Hydroxyestrone diacetate</a></li> <li><a href="/wiki/Lynestrenol" title="Lynestrenol">Lynestrenol</a></li> <li><a href="/wiki/Lynestrenol_phenylpropionate" title="Lynestrenol phenylpropionate">Lynestrenol phenylpropionate</a></li> <li><a href="/wiki/Mestranol" title="Mestranol">Mestranol</a></li> <li><a href="/wiki/Methylestradiol" title="Methylestradiol">Methylestradiol</a></li> <li><a href="/wiki/Moxestrol" title="Moxestrol">Moxestrol</a></li> <li><a href="/wiki/Mytatrienediol" title="Mytatrienediol">Mytatrienediol</a></li> <li><a href="/wiki/Nilestriol" title="Nilestriol">Nilestriol</a></li> <li><a href="/wiki/Norethisterone" title="Norethisterone">Norethisterone</a></li> <li><a href="/wiki/Noretynodrel" title="Noretynodrel">Noretynodrel</a></li> <li><a href="/wiki/Orestrate" title="Orestrate">Orestrate</a></li> <li><a href="/wiki/Pentolame" title="Pentolame">Pentolame</a></li> <li><a href="/wiki/Prodiame" title="Prodiame">Prodiame</a></li> <li><a href="/wiki/Prolame" title="Prolame">Prolame</a></li> <li><a href="/wiki/Promestriene" title="Promestriene">Promestriene</a></li> <li><a href="/wiki/RU-16117" title="RU-16117">RU-16117</a></li> <li><a href="/wiki/Quinestradol" title="Quinestradol">Quinestradol</a></li> <li><a href="/wiki/Quinestrol" title="Quinestrol">Quinestrol</a></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li></ul> <ul><li><i>Nonsteroidal:</i> <a href="/wiki/(R,R)-Tetrahydrochrysene" title="(R,R)-Tetrahydrochrysene">(R,R)-THC</a></li> <li><a href="/wiki/(S,S)-Tetrahydrochrysene" title="(S,S)-Tetrahydrochrysene">(S,S)-THC</a></li> <li><a href="/wiki/2,8-Dihydroxyhexahydrochrysene" title="2,8-Dihydroxyhexahydrochrysene">2,8-DHHHC</a></li> <li><a href="/w/index.php?title=%CE%92-LGND1&action=edit&redlink=1" class="new" title="Β-LGND1 (page does not exist)">β-LGND1</a></li> <li><a href="/wiki/%CE%92-LGND2" title="Β-LGND2">β-LGND2 (GTx-878)</a></li> <li><a href="/w/index.php?title=AC-186&action=edit&redlink=1" class="new" title="AC-186 (page does not exist)">AC-186</a></li> <li><a href="/wiki/Allenestrol" title="Allenestrol">Allenestrol</a></li> <li><a href="/wiki/Allenolic_acid" title="Allenolic acid">Allenolic acid</a></li> <li><a href="/wiki/Benzestrol" title="Benzestrol">Benzestrol</a></li> <li><a href="/wiki/Bifluranol" title="Bifluranol">Bifluranol</a></li> <li><a href="/wiki/Bisdehydrodoisynolic_acid" title="Bisdehydrodoisynolic acid">Bisdehydrodoisynolic acid</a></li> <li><a href="/wiki/Butestrol" title="Butestrol">Butestrol</a></li> <li><a href="/wiki/Carbestrol" title="Carbestrol">Carbestrol</a></li> <li><a href="/wiki/D-15414" title="D-15414">D-15414</a></li> <li><a href="/wiki/DCW234" title="DCW234">DCW234</a></li> <li><a href="/wiki/Diarylpropionitrile" title="Diarylpropionitrile">Diarylpropionitrile</a></li> <li><a href="/wiki/Dienestrol" title="Dienestrol">Dienestrol</a> <ul><li><a href="/wiki/Dienestrol_diacetate" title="Dienestrol diacetate">Dienestrol diacetate</a></li></ul></li> <li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Diethylstilbestrol_esters" title="List of estrogen esters">Diethylstilbestrol esters</a></li></ul></li> <li><a href="/wiki/Dimestrol" title="Dimestrol">Dimestrol (dianisylhexene)</a></li> <li><a href="/wiki/Dimethylstilbestrol" title="Dimethylstilbestrol">Dimethylstilbestrol</a></li> <li><a href="/wiki/Doisynoestrol" title="Doisynoestrol">Doisynoestrol (fenocycline)</a></li> <li><a href="/wiki/Doisynolic_acid" title="Doisynolic acid">Doisynolic acid</a></li> <li><a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Elacestrant" title="Elacestrant">Elacestrant</a></li> <li><a href="/wiki/ERB-196" title="ERB-196">ERB-196 (WAY-202196)</a></li> <li><a href="/wiki/Erteberel" title="Erteberel">Erteberel (SERBA-1, LY-500307)</a></li> <li><a href="/wiki/Estrobin" title="Estrobin">Estrobin (DBE)</a></li> <li><a href="/wiki/Fenestrel" title="Fenestrel">Fenestrel</a></li> <li><a href="/wiki/FERb_033" title="FERb 033">FERb 033</a></li> <li><a href="/wiki/Fosfestrol" title="Fosfestrol">Fosfestrol (diethylstilbestrol diphosphate)</a></li> <li><a href="/wiki/Furostilbestrol" title="Furostilbestrol">Furostilbestrol (diethylstilbestrol difuroate)</a></li> <li><a href="/wiki/GTx-758" title="GTx-758">GTx-758</a></li> <li><a href="/wiki/Hexestrol" title="Hexestrol">Hexestrol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Hexestrol_esters" title="List of estrogen esters">Hexestrol esters</a></li></ul></li> <li><a href="/wiki/ICI-85966" title="ICI-85966">ICI-85966 (Stilbostat)</a></li> <li><a href="/wiki/M2613" title="M2613">M2613</a></li> <li><a href="/wiki/Meso-Butestrol" title="Meso-Butestrol"><i>meso</i>-Butestrol</a></li> <li><a href="/wiki/Meso-Hexestrol" class="mw-redirect" title="Meso-Hexestrol"><i>meso</i>-Hexestrol</a></li> <li><a href="/wiki/Mestilbol" title="Mestilbol">Mestilbol</a></li> <li><a href="/wiki/Methallenestril" title="Methallenestril">Methallenestril</a></li> <li><a href="/wiki/Methestrol" title="Methestrol">Methestrol</a></li> <li><a href="/wiki/Methestrol_dipropionate" title="Methestrol dipropionate">Methestrol dipropionate</a></li> <li><a href="/wiki/Paroxypropione" title="Paroxypropione">Paroxypropione</a></li> <li><a href="/wiki/Pentafluranol" title="Pentafluranol">Pentafluranol</a></li> <li><a href="/wiki/Phenestrol" title="Phenestrol">Phenestrol</a></li> <li><a href="/wiki/Prinaberel" title="Prinaberel">Prinaberel (ERB-041, WAY-202041)</a></li> <li><a href="/wiki/Propylpyrazoletriol" title="Propylpyrazoletriol">Propylpyrazoletriol</a></li> <li><a href="/wiki/Quadrosilan" title="Quadrosilan">Quadrosilan</a></li> <li><a href="/w/index.php?title=SC-3296&action=edit&redlink=1" class="new" title="SC-3296 (page does not exist)">SC-3296</a></li> <li><a href="/wiki/SC-4289" title="SC-4289">SC-4289</a></li> <li><a href="/wiki/SERBA-2" title="SERBA-2">SERBA-2</a></li> <li><a href="/wiki/SKF-82,958" title="SKF-82,958">SKF-82,958</a></li> <li><a href="/wiki/Terfluranol" title="Terfluranol">Terfluranol</a></li> <li><a href="/wiki/Triphenylbromoethylene" title="Triphenylbromoethylene">Triphenylbromoethylene</a></li> <li><a href="/wiki/Triphenylchloroethylene" title="Triphenylchloroethylene">Triphenylchloroethylene</a></li> <li><a href="/wiki/Triphenyliodoethylene" title="Triphenyliodoethylene">Triphenyliodoethylene</a></li> <li><a href="/wiki/Triphenylmethylethylene" title="Triphenylmethylethylene">Triphenylmethylethylene (triphenylpropene)</a></li> <li><a href="/wiki/WAY-166818" title="WAY-166818">WAY-166818</a></li> <li><a href="/w/index.php?title=WAY-169916&action=edit&redlink=1" class="new" title="WAY-169916 (page does not exist)">WAY-169916</a></li> <li><a href="/wiki/WAY-200070" title="WAY-200070">WAY-200070</a></li> <li><a href="/wiki/WAY-204688" title="WAY-204688">WAY-204688 (SIM-688)</a></li> <li><a href="/wiki/WAY-214156" title="WAY-214156">WAY-214156</a></li></ul> <ul><li><i>Unknown/unsorted:</i> <a href="/wiki/ERB-26" title="ERB-26">ERB-26</a></li> <li><a href="/wiki/ERA-45" title="ERA-45">ERA-45</a></li> <li><a href="/wiki/ERB-79" title="ERB-79">ERB-79</a></li> <li><a href="/wiki/ZK-283197" title="ZK-283197">ZK-283197</a></li></ul> <ul><li><i>Xenoestrogens:</i> <a href="/wiki/Anise" title="Anise">Anise</a>-related (e.g., <a href="/wiki/Anethole" title="Anethole">anethole</a>, <a href="/wiki/Anol" title="Anol">anol</a>, <a href="/wiki/Dianethole" title="Dianethole">dianethole</a>, <a href="/wiki/Dianol" title="Dianol">dianol</a>, <a href="/wiki/Photoanethole" title="Photoanethole">photoanethole</a>)</li> <li><a href="/wiki/Chalconoid" title="Chalconoid">Chalconoids</a> (e.g., <a href="/wiki/Isoliquiritigenin" title="Isoliquiritigenin">isoliquiritigenin</a>, <a href="/wiki/Phloretin" title="Phloretin">phloretin</a>, <a href="/wiki/Phlorizin" title="Phlorizin">phlorizin (phloridzin)</a>, <a href="/wiki/Wedelolactone" title="Wedelolactone">wedelolactone</a>)</li> <li><a href="/wiki/Coumestan" title="Coumestan">Coumestans</a> (e.g., <a href="/wiki/Coumestrol" title="Coumestrol">coumestrol</a>, <a href="/wiki/Psoralidin" title="Psoralidin">psoralidin</a>)</li> <li><a href="/wiki/Flavonoid" title="Flavonoid">Flavonoids</a> (incl. <a href="/wiki/7,8-Dihydroxyflavone" class="mw-redirect" title="7,8-Dihydroxyflavone">7,8-DHF</a>, <a href="/wiki/8-Prenylnaringenin" title="8-Prenylnaringenin">8-prenylnaringenin</a>, <a href="/wiki/Apigenin" title="Apigenin">apigenin</a>, <a href="/wiki/Baicalein" title="Baicalein">baicalein</a>, <a href="/wiki/Baicalin" title="Baicalin">baicalin</a>, <a href="/wiki/Biochanin_A" title="Biochanin A">biochanin A</a>, <a href="/wiki/Calycosin" title="Calycosin">calycosin</a>, <a href="/wiki/Catechin" title="Catechin">catechin</a>, <a href="/wiki/Daidzein" title="Daidzein">daidzein</a>, <a href="/wiki/Daidzin" title="Daidzin">daidzin</a>, <a href="/wiki/Epicatechin_gallate" title="Epicatechin gallate">ECG</a>, <a href="/wiki/Epigallocatechin_gallate" title="Epigallocatechin gallate">EGCG</a>, <a href="/wiki/Epicatechin" class="mw-redirect" title="Epicatechin">epicatechin</a>, <a href="/wiki/Equol" title="Equol">equol</a>, <a href="/wiki/Formononetin" title="Formononetin">formononetin</a>, <a href="/wiki/Glabrene" title="Glabrene">glabrene</a>, <a href="/wiki/Glabridin" title="Glabridin">glabridin</a>, <a href="/wiki/Genistein" title="Genistein">genistein</a>, <a href="/wiki/Genistin" title="Genistin">genistin</a>, <a href="/wiki/Glycitein" title="Glycitein">glycitein</a>, <a href="/wiki/Kaempferol" title="Kaempferol">kaempferol</a>, <a href="/wiki/Liquiritigenin" title="Liquiritigenin">liquiritigenin</a>, <a href="/wiki/Mirificin" title="Mirificin">mirificin</a>, <a href="/wiki/Myricetin" title="Myricetin">myricetin</a>, <a href="/wiki/Naringenin" title="Naringenin">naringenin</a>, <a href="/w/index.php?title=Penduletin&action=edit&redlink=1" class="new" title="Penduletin (page does not exist)">penduletin</a>, <a href="/wiki/Pinocembrin" title="Pinocembrin">pinocembrin</a>, <a href="/wiki/Prunetin" title="Prunetin">prunetin</a>, <a href="/wiki/Puerarin" title="Puerarin">puerarin</a>, <a href="/wiki/Quercetin" title="Quercetin">quercetin</a>, <a href="/wiki/Tectoridin" title="Tectoridin">tectoridin</a>, <a href="/wiki/Tectorigenin" title="Tectorigenin">tectorigenin</a>)</li> <li><a href="/wiki/Lavender_oil" title="Lavender oil">Lavender oil</a></li> <li><a href="/wiki/Lignan" title="Lignan">Lignans</a> (e.g., <a href="/wiki/Enterodiol" title="Enterodiol">enterodiol</a>, <a href="/wiki/Enterolactone" title="Enterolactone">enterolactone</a>, <a href="/wiki/Nyasol" title="Nyasol">nyasol (<i>cis</i>-hinokiresinol)</a>)</li> <li><a href="/wiki/Metalloestrogen" title="Metalloestrogen">Metalloestrogens</a> (e.g., <a href="/wiki/Cadmium" title="Cadmium">cadmium</a>)</li> <li><a href="/wiki/Pesticide" title="Pesticide">Pesticides</a> (e.g., <a href="/wiki/Alternariol" title="Alternariol">alternariol</a>, <a href="/wiki/Dieldrin" title="Dieldrin">dieldrin</a>, <a href="/wiki/Endosulfan" title="Endosulfan">endosulfan</a>, <a href="/wiki/Fenarimol" title="Fenarimol">fenarimol</a>, <a href="/wiki/HPTE" title="HPTE">HPTE</a>, <a href="/wiki/Methiocarb" title="Methiocarb">methiocarb</a>, <a href="/wiki/Methoxychlor" title="Methoxychlor">methoxychlor</a>, <a href="/wiki/Triclocarban" title="Triclocarban">triclocarban</a>, <a href="/wiki/Triclosan" title="Triclosan">triclosan</a>)</li> <li><a href="/wiki/Phytosteroid" title="Phytosteroid">Phytosteroids</a> (e.g., <a href="/wiki/Digitoxin" title="Digitoxin">digitoxin</a> (<a href="/wiki/Digitalis" title="Digitalis">digitalis</a>), <a href="/wiki/Diosgenin" title="Diosgenin">diosgenin</a>, <a href="/wiki/Guggulsterone" title="Guggulsterone">guggulsterone</a>)</li> <li><a href="/wiki/Phytosterol" title="Phytosterol">Phytosterols</a> (e.g., <a href="/wiki/%CE%92-sitosterol" class="mw-redirect" title="Β-sitosterol">β-sitosterol</a>, <a href="/wiki/Campesterol" title="Campesterol">campesterol</a>, <a href="/wiki/Stigmasterol" title="Stigmasterol">stigmasterol</a>)</li> <li><a href="/wiki/Resorcylic_acid_lactone" title="Resorcylic acid lactone">Resorcylic acid lactones</a> (e.g., <a href="/wiki/Zearalanone" title="Zearalanone">zearalanone</a>, <a href="/wiki/%CE%91-zearalenol" class="mw-redirect" title="Α-zearalenol">α-zearalenol</a>, <a href="/wiki/%CE%92-zearalenol" class="mw-redirect" title="Β-zearalenol">β-zearalenol</a>, <a href="/wiki/Zearalenone" title="Zearalenone">zearalenone</a>, <a href="/wiki/Zeranol" title="Zeranol">zeranol (α-zearalanol)</a>, <a href="/wiki/Taleranol" title="Taleranol">taleranol (teranol, β-zearalanol)</a>)</li> <li><a class="mw-selflink selflink">Steroid</a>-like (e.g., <a href="/wiki/Deoxymiroestrol" class="mw-redirect" title="Deoxymiroestrol">deoxymiroestrol</a>, <a href="/wiki/Miroestrol" title="Miroestrol">miroestrol</a>)</li> <li><a href="/wiki/Stilbenoid" title="Stilbenoid">Stilbenoids</a> (e.g., <a href="/wiki/Resveratrol" title="Resveratrol">resveratrol</a>, <a href="/wiki/Rhaponticin" title="Rhaponticin">rhaponticin</a>)</li> <li><a href="/wiki/Synthetic_xenoestrogen" class="mw-redirect" title="Synthetic xenoestrogen">Synthetic xenoestrogens</a> (e.g., <a href="/wiki/Alkylphenol" title="Alkylphenol">alkylphenols</a>, <a href="/wiki/Bisphenol" title="Bisphenol">bisphenols</a> (e.g., <a href="/wiki/Bisphenol_A" title="Bisphenol A">BPA</a>, <a href="/wiki/Bisphenol_F" title="Bisphenol F">BPF</a>, <a href="/wiki/Bisphenol_S" title="Bisphenol S">BPS</a>), <a href="/wiki/Dichlorodiphenyltrichloroethane" class="mw-redirect" title="Dichlorodiphenyltrichloroethane">DDT</a>, <a href="/wiki/Paraben" title="Paraben">parabens</a>, <a href="/wiki/Polybrominated_biphenyl" title="Polybrominated biphenyl">PBBs</a>, <a href="/wiki/4-hydroxybenzoic_acid" class="mw-redirect" title="4-hydroxybenzoic acid">PHBA</a>, <a href="/wiki/Phthalate" class="mw-redirect" title="Phthalate">phthalates</a>, <a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">PCBs</a>)</li> <li>Others (e.g., <a href="/wiki/Agnuside" title="Agnuside">agnuside</a>, <a href="/w/index.php?title=Rotundifuran&action=edit&redlink=1" class="new" title="Rotundifuran (page does not exist)">rotundifuran</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Mixed<br />(<a href="/wiki/Selective_estrogen_receptor_modulators" class="mw-redirect" title="Selective estrogen receptor modulators"><abbr title="Selective estrogen receptor modulators">SERMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Selective estrogen receptor modulators</span>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Phenylbenzofuran" title="2-Phenylbenzofuran">2-Phenylbenzofuran</a></li> <li><a href="/w/index.php?title=2-Phenylbenzothiophene&action=edit&redlink=1" class="new" title="2-Phenylbenzothiophene (page does not exist)">2-Phenylbenzothiophene</a></li> <li><a href="/wiki/4%27-Hydroxynorendoxifen" title="4'-Hydroxynorendoxifen">4'-Hydroxynorendoxifen</a></li> <li><a href="/wiki/27-Hydroxycholesterol" title="27-Hydroxycholesterol">27-Hydroxycholesterol</a></li> <li><a href="/wiki/Acefluranol" title="Acefluranol">Acefluranol</a></li> <li><a href="/wiki/Acolbifene" title="Acolbifene">Acolbifene</a></li> <li><a href="/wiki/Afimoxifene" title="Afimoxifene">Afimoxifene</a></li> <li><a href="/wiki/Anordiol" title="Anordiol">Anordiol</a></li> <li><a href="/wiki/Anordrin" title="Anordrin">Anordrin</a></li> <li><a href="/wiki/Arzoxifene" title="Arzoxifene">Arzoxifene</a></li> <li><a href="/wiki/Bazedoxifene" title="Bazedoxifene">Bazedoxifene</a></li> <li><a href="/wiki/Brilanestrant" title="Brilanestrant">Brilanestrant</a></li> <li><a href="/wiki/Broparestrol" title="Broparestrol">Broparestrol</a></li> <li><a href="/wiki/Camizestrant" title="Camizestrant">Camizestrant</a></li> <li><a href="/wiki/Chlorotrianisene" title="Chlorotrianisene">Chlorotrianisene</a></li> <li><a href="/wiki/Clomifene" title="Clomifene">Clomifene</a></li> <li><a href="/wiki/Clomifenoxide" title="Clomifenoxide">Clomifenoxide</a></li> <li><a href="/w/index.php?title=CN-55945-27&action=edit&redlink=1" class="new" title="CN-55945-27 (page does not exist)">CN-55945-27</a></li> <li><a href="/wiki/Cyclofenil" title="Cyclofenil">Cyclofenil</a></li> <li><a href="/w/index.php?title=D-15413&action=edit&redlink=1" class="new" title="D-15413 (page does not exist)">D-15413</a></li> <li><a href="/wiki/Desmethylchlorotrianisene" title="Desmethylchlorotrianisene">Desmethylchlorotrianisene</a></li> <li><a href="/wiki/Droloxifene" title="Droloxifene">Droloxifene</a></li> <li><a href="/wiki/Enclomifene" title="Enclomifene">Enclomifene</a></li> <li><a href="/wiki/Endoxifen" title="Endoxifen">Endoxifen</a></li> <li><a href="/wiki/Etacstil" title="Etacstil">Etacstil (GW-5638, DPC-974)</a></li> <li><a href="/wiki/Ethamoxytriphetol" title="Ethamoxytriphetol">Ethamoxytriphetol (MER-25)</a></li> <li><a href="/wiki/Femarelle" title="Femarelle">Femarelle</a></li> <li><a href="/wiki/Fispemifene" title="Fispemifene">Fispemifene</a></li> <li><a href="/w/index.php?title=GW-7604&action=edit&redlink=1" class="new" title="GW-7604 (page does not exist)">GW-7604</a></li> <li><a href="/wiki/ICI-55548" class="mw-redirect" title="ICI-55548">ICI-55548</a></li> <li><a href="/wiki/Idoxifene" title="Idoxifene">Idoxifene</a></li> <li><a href="/wiki/Lasofoxifene" title="Lasofoxifene">Lasofoxifene</a></li> <li><a href="/wiki/Levormeloxifene" title="Levormeloxifene">Levormeloxifene</a></li> <li><a href="/wiki/LN-1643" class="mw-redirect" title="LN-1643">LN-1643</a></li> <li><a href="/wiki/LN-2299" class="mw-redirect" title="LN-2299">LN-2299</a></li> <li><a href="/w/index.php?title=LY-117018&action=edit&redlink=1" class="new" title="LY-117018 (page does not exist)">LY-117018</a></li> <li><a href="/wiki/Menerba" title="Menerba">Menerba</a></li> <li><a href="/wiki/Miproxifene" title="Miproxifene">Miproxifene</a></li> <li><a href="/wiki/Miproxifene_phosphate" title="Miproxifene phosphate">Miproxifene phosphate</a></li> <li><a href="/w/index.php?title=MRL-37&action=edit&redlink=1" class="new" title="MRL-37 (page does not exist)">MRL-37</a></li> <li><a href="/wiki/Nafoxidine" title="Nafoxidine">Nafoxidine</a></li> <li><a href="/wiki/Nitromifene" title="Nitromifene">Nitromifene</a></li> <li><a href="/wiki/NNC_45-0095" title="NNC 45-0095">NNC 45-0095</a></li> <li><a href="/w/index.php?title=NNC_45-0320&action=edit&redlink=1" class="new" title="NNC 45-0320 (page does not exist)">NNC 45-0320</a></li> <li><a href="/w/index.php?title=NNC_45-0781&action=edit&redlink=1" class="new" title="NNC 45-0781 (page does not exist)">NNC 45-0781</a></li> <li><a href="/w/index.php?title=NNC_45-1506&action=edit&redlink=1" class="new" title="NNC 45-1506 (page does not exist)">NNC 45-1506</a></li> <li><a href="/wiki/Ormeloxifene" title="Ormeloxifene">Ormeloxifene</a></li> <li><a href="/wiki/Ospemifene" title="Ospemifene">Ospemifene</a></li> <li><a href="/wiki/Panomifene" title="Panomifene">Panomifene</a></li> <li><a href="/wiki/Pipendoxifene" title="Pipendoxifene">Pipendoxifene</a></li> <li><a href="/w/index.php?title=Promensil&action=edit&redlink=1" class="new" title="Promensil (page does not exist)">Promensil</a></li> <li><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></li> <li><a href="/wiki/Rimostil" title="Rimostil">Rimostil (P-081)</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/w/index.php?title=SS1010&action=edit&redlink=1" class="new" title="SS1010 (page does not exist)">SS1010</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a></li> <li><a href="/wiki/TAS-108" title="TAS-108">TAS-108 (SR-16234)</a></li> <li><a href="/wiki/Toremifene" title="Toremifene">Toremifene</a></li> <li><a href="/wiki/Trioxifene" title="Trioxifene">Trioxifene</a></li> <li><a href="/w/index.php?title=TZE-5323&action=edit&redlink=1" class="new" title="TZE-5323 (page does not exist)">TZE-5323</a></li> <li><a href="/w/index.php?title=U-11555A&action=edit&redlink=1" class="new" title="U-11555A (page does not exist)">U-11555A</a></li> <li><a href="/w/index.php?title=U-11634&action=edit&redlink=1" class="new" title="U-11634 (page does not exist)">U-11634</a></li> <li><a href="/w/index.php?title=Y-134&action=edit&redlink=1" class="new" title="Y-134 (page does not exist)">Y-134</a></li> <li><a href="/wiki/Zindoxifene" title="Zindoxifene">Zindoxifene</a></li> <li><a href="/wiki/Zuclomifene" title="Zuclomifene">Zuclomifene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/(R,R)-Tetrahydrochrysene" title="(R,R)-Tetrahydrochrysene">(R,R)-THC</a></li> <li><a href="/wiki/7%CE%B2-Hydroxy-DHEA" title="7β-Hydroxy-DHEA">7β-Hydroxy-DHEA</a></li> <li><a href="/w/index.php?title=Chloroindazole&action=edit&redlink=1" class="new" title="Chloroindazole (page does not exist)">Chloroindazole</a></li> <li><a href="/wiki/Cytestrol_acetate" title="Cytestrol acetate">Cytestrol acetate</a></li> <li><a href="/w/index.php?title=EM-800&action=edit&redlink=1" class="new" title="EM-800 (page does not exist)">EM-800 (SCH-57050)</a></li> <li><a href="/wiki/Epitiostanol" title="Epitiostanol">Epitiostanol</a></li> <li><a href="/w/index.php?title=ERA-90&action=edit&redlink=1" class="new" title="ERA-90 (page does not exist)">ERA-90</a></li> <li><a href="/w/index.php?title=ERB-88&action=edit&redlink=1" class="new" title="ERB-88 (page does not exist)">ERB-88</a></li> <li><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant (ICI-182780)</a></li> <li><a href="/wiki/Glyceollin" title="Glyceollin">Glyceollins</a> (<a href="/wiki/Glyceollin_I" title="Glyceollin I">I</a>, <a href="/w/index.php?title=Glyceollin_II&action=edit&redlink=1" class="new" title="Glyceollin II (page does not exist)">II</a>, <a href="/wiki/Glyceollin_III" title="Glyceollin III">III</a>, <a href="/w/index.php?title=Glyceollin_IV&action=edit&redlink=1" class="new" title="Glyceollin IV (page does not exist)">IV</a>)</li> <li><a href="/wiki/ICI-164384" title="ICI-164384">ICI-164384</a></li> <li><a href="/w/index.php?title=MDL-101906&action=edit&redlink=1" class="new" title="MDL-101906 (page does not exist)">MDL-101906</a></li> <li><a href="/wiki/Mepitiostane" title="Mepitiostane">Mepitiostane</a></li> <li><a href="/wiki/Methylepitiostanol" title="Methylepitiostanol">Methylepitiostanol</a></li> <li><a href="/wiki/Methylpiperidinopyrazole" title="Methylpiperidinopyrazole">Methylpiperidinopyrazole</a></li> <li><a href="/wiki/MIBE" title="MIBE">MIBE</a></li> <li><a href="/w/index.php?title=Oxabicycloheptene_sulfonate&action=edit&redlink=1" class="new" title="Oxabicycloheptene sulfonate (page does not exist)">Oxabicycloheptene sulfonate</a></li> <li><a href="/wiki/Phenytoin" title="Phenytoin">Phenytoin</a></li> <li><a href="/wiki/PHTPP" title="PHTPP">PHTPP</a></li> <li><a href="/wiki/Prochloraz" title="Prochloraz">Prochloraz</a></li> <li><a href="/w/index.php?title=RU-39411&action=edit&redlink=1" class="new" title="RU-39411 (page does not exist)">RU-39411</a></li> <li><a href="/w/index.php?title=RU-58668&action=edit&redlink=1" class="new" title="RU-58668 (page does not exist)">RU-58668</a></li> <li><a href="/w/index.php?title=SS1020&action=edit&redlink=1" class="new" title="SS1020 (page does not exist)">SS1020</a></li> <li><a href="/wiki/TAS-108" title="TAS-108">TAS-108 (SR-16234)</a></li> <li><a href="/wiki/ZB716" title="ZB716">ZB716</a></li> <li><a href="/w/index.php?title=ZK-164015&action=edit&redlink=1" class="new" title="ZK-164015 (page does not exist)">ZK-164015</a></li> <li><a href="/w/index.php?title=ZK-191703&action=edit&redlink=1" class="new" title="ZK-191703 (page does not exist)">ZK-191703</a></li></ul> <ul><li><i>Coregulator-binding modulators:</i> <a href="/wiki/ERX-11" title="ERX-11">ERX-11</a></li></ul> <ul><li><i>Noncompetitive inhibitors:</i> <a href="/wiki/Trilostane" title="Trilostane">Trilostane</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/G_protein-coupled_estrogen_receptor" class="mw-redirect" title="G protein-coupled estrogen receptor"><abbr title="G protein-coupled estrogen receptor">GPER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip G protein-coupled estrogen receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Methoxyestradiol" title="2-Methoxyestradiol">2-Methoxyestradiol</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/Afimoxifene" title="Afimoxifene">Afimoxifene (4-hydroxytamoxifen)</a></li> <li><a href="/wiki/Aldosterone" title="Aldosterone">Aldosterone</a></li> <li><a href="/wiki/Atrazine" title="Atrazine">Atrazine</a></li> <li><a href="/wiki/Bisphenol_A" title="Bisphenol A">Bisphenol A</a></li> <li><a href="/wiki/Daidzein" title="Daidzein">Daidzein</a></li> <li><a href="/wiki/DDT" title="DDT">DDT</a> (<a href="/wiki/P,p%27-DDT" class="mw-redirect" title="P,p'-DDT">p,p'-DDT</a>, <a href="/w/index.php?title=O%27,p%27-DDE&action=edit&redlink=1" class="new" title="O',p'-DDE (page does not exist)">o',p'-DDE</a>)</li> <li><a href="/wiki/Diarylpropionitrile" title="Diarylpropionitrile">Diarylpropionitrile</a></li> <li><a href="/wiki/Equol" title="Equol">Equol</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a></li> <li><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant (ICI-182780)</a></li> <li><a href="/w/index.php?title=G-1_(drug)&action=edit&redlink=1" class="new" title="G-1 (drug) (page does not exist)">G-1</a></li> <li><a href="/wiki/Genistein" title="Genistein">Genistein</a></li> <li><a href="/w/index.php?title=GPER-L1&action=edit&redlink=1" class="new" title="GPER-L1 (page does not exist)">GPER-L1</a></li> <li><a href="/w/index.php?title=GPER-L2&action=edit&redlink=1" class="new" title="GPER-L2 (page does not exist)">GPER-L2</a></li> <li><a href="/wiki/Hydroxytyrosol" title="Hydroxytyrosol">Hydroxytyrosol</a></li> <li><a href="/wiki/Kepone" class="mw-redirect" title="Kepone">Kepone</a></li> <li><a href="/wiki/Niacin" title="Niacin">Niacin</a></li> <li><a href="/wiki/Niacinamide" class="mw-redirect" title="Niacinamide">Niacinamide</a></li> <li><a href="/wiki/Nonylphenol" title="Nonylphenol">Nonylphenol</a></li> <li><a href="/wiki/Oleuropein" title="Oleuropein">Oleuropein</a></li> <li><a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">PCBs</a> (<a href="/w/index.php?title=2,2%27,5%27-PCB-4-OH&action=edit&redlink=1" class="new" title="2,2',5'-PCB-4-OH (page does not exist)">2,2',5'-PCB-4-OH</a>)</li> <li><a href="/wiki/Propylpyrazoletriol" title="Propylpyrazoletriol">Propylpyrazoletriol</a></li> <li><a href="/wiki/Quercetin" title="Quercetin">Quercetin</a></li> <li><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></li> <li><a href="/wiki/Resveratrol" title="Resveratrol">Resveratrol</a></li> <li><a href="/w/index.php?title=STX_(drug)&action=edit&redlink=1" class="new" title="STX (drug) (page does not exist)">STX</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a></li> <li><a href="/wiki/Tectoridin" title="Tectoridin">Tectoridin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/CCL18" title="CCL18">CCL18</a></li> <li><a href="/wiki/Estriol" title="Estriol">Estriol</a></li> <li><a href="/w/index.php?title=G-15_(drug)&action=edit&redlink=1" class="new" title="G-15 (drug) (page does not exist)">G-15</a></li> <li><a href="/w/index.php?title=G-36_(drug)&action=edit&redlink=1" class="new" title="G-36 (drug) (page does not exist)">G-36</a></li> <li><a href="/wiki/MIBE" title="MIBE">MIBE</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Unknown</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a></li> <li><a href="/wiki/Zearalenone" title="Zearalenone">Zearalenone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Estrogens_and_antiestrogens" title="Template:Estrogens and antiestrogens">Estrogens and antiestrogens</a></dd> <dd><a href="/wiki/Template:Androgen_receptor_modulators" title="Template:Androgen receptor modulators">Androgen receptor modulators</a></dd> <dd><a href="/wiki/Template:Progesterone_receptor_modulators" title="Template:Progesterone receptor modulators">Progesterone receptor modulators</a></dd> <dd><a href="/wiki/List_of_steroidal_estrogens" class="mw-redirect" title="List of steroidal estrogens">List of estrogens</a></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Glucocorticoid_receptor_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Glucocorticoid_receptor_modulators" title="Template:Glucocorticoid receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Glucocorticoid_receptor_modulators" title="Template talk:Glucocorticoid receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Glucocorticoid_receptor_modulators" title="Special:EditPage/Template:Glucocorticoid receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Glucocorticoid_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Glucocorticoid_receptor" title="Glucocorticoid receptor">Glucocorticoid receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Glucocorticoid_receptor" title="Glucocorticoid receptor"><abbr title="Glucocorticoid receptor">GR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Glucocorticoid receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center"><a href="/wiki/Glucocorticoid" title="Glucocorticoid">Agonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Cortisol-like and related (16-unsubstituted):</i> <a href="/wiki/Tetrahydrocorticosterone" title="Tetrahydrocorticosterone">3α,5α-Tetrahydrocorticosterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydrocorticosterone" title="5α-Dihydrocorticosterone">5α-Dihydrocorticosterone</a></li> <li><a href="/wiki/9%CE%B1-Fluorocortisone" title="9α-Fluorocortisone">9α-Fluorocortisone (alfluorone)</a></li> <li><a href="/wiki/11-Dehydrocorticosterone" title="11-Dehydrocorticosterone">11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone)</a> <ul><li><a href="/w/index.php?title=11-Dehydrocorticosterone_acetate&action=edit&redlink=1" class="new" title="11-Dehydrocorticosterone acetate (page does not exist)">11-Dehydrocorticosterone acetate</a></li></ul></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone (desoxycortone, deoxycortone, desoxycorticosterone)</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Desoxycortone_esters" title="List of corticosteroid esters">Desoxycortone esters</a></li></ul></li> <li><a href="/wiki/11-Deoxycortisol" title="11-Deoxycortisol">11-Deoxycortisol (cortodoxone, cortexolone)</a> <ul><li><a href="/wiki/Cortifen" title="Cortifen">Cortifen (cortiphen, kortifen)</a></li> <li><a href="/w/index.php?title=Cortodoxone_acetate&action=edit&redlink=1" class="new" title="Cortodoxone acetate (page does not exist)">Cortodoxone acetate</a></li></ul></li> <li><a href="/wiki/21-Deoxycortisol" title="21-Deoxycortisol">21-Deoxycortisol</a></li> <li><a href="/wiki/%CE%947-Prednisolone" title="Δ7-Prednisolone">Δ<sup>7</sup>-Prednisolone</a> <ul><li><a href="/w/index.php?title=%CE%947-Prednisolone_21-acetate&action=edit&redlink=1" class="new" title="Δ7-Prednisolone 21-acetate (page does not exist)">Δ<sup>7</sup>-Prednisolone 21-acetate</a></li></ul></li> <li><a href="/wiki/Amebucort" title="Amebucort">Amebucort</a></li> <li><a href="/wiki/Chloroprednisone" title="Chloroprednisone">Chloroprednisone</a> <ul><li><a href="/wiki/Chloroprednisone_acetate" title="Chloroprednisone acetate">Chloroprednisone acetate</a></li></ul></li> <li><a href="/wiki/Cloprednol" title="Cloprednol">Cloprednol</a> <ul><li><a href="/w/index.php?title=Cloprednol_acetate&action=edit&redlink=1" class="new" title="Cloprednol acetate (page does not exist)">Cloprednol acetate</a></li></ul></li> <li><a href="/wiki/Corticosterone" title="Corticosterone">Corticosterone</a> <ul><li><a href="/w/index.php?title=Corticosterone_acetate&action=edit&redlink=1" class="new" title="Corticosterone acetate (page does not exist)">Corticosterone acetate</a></li> <li><a href="/w/index.php?title=Corticosterone_benzoate&action=edit&redlink=1" class="new" title="Corticosterone benzoate (page does not exist)">Corticosterone benzoate</a></li></ul></li> <li><a href="/wiki/Cortisol" title="Cortisol">Cortisol</a> (<a href="/wiki/Hydrocortisone" title="Hydrocortisone">hydrocortisone</a>) <ul><li><a href="/wiki/Benzodrocortisone" title="Benzodrocortisone">Benzodrocortisone (hydrocortisone benzoate)</a></li> <li><a href="/wiki/Hydrocortamate" title="Hydrocortamate">Hydrocortamate (hydrocortisone diethylaminoacetate)</a></li> <li><a href="/wiki/List_of_corticosteroid_esters#Hydrocortisone_esters" title="List of corticosteroid esters">Hydrocortisone esters</a></li></ul></li> <li><a href="/wiki/Cortisone" title="Cortisone">Cortisone</a> <ul><li><a href="/wiki/Cortisone_acetate" title="Cortisone acetate">Cortisone acetate</a></li></ul></li> <li><a href="/wiki/Deprodone" title="Deprodone">Deprodone</a> <ul><li><a href="/w/index.php?title=Deprodone_propionate&action=edit&redlink=1" class="new" title="Deprodone propionate (page does not exist)">Deprodone propionate</a></li></ul></li> <li><a href="/wiki/Dichlorisone" title="Dichlorisone">Dichlorisone</a> <ul><li><a href="/w/index.php?title=Dichlorisone_acetate&action=edit&redlink=1" class="new" title="Dichlorisone acetate (page does not exist)">Dichlorisone acetate</a></li> <li><a href="/w/index.php?title=Dichlorisone_diacetate&action=edit&redlink=1" class="new" title="Dichlorisone diacetate (page does not exist)">Dichlorisone diacetate</a></li></ul></li> <li><a href="/wiki/Difluprednate" title="Difluprednate">Difluprednate</a></li> <li><a href="/wiki/Endrisone" title="Endrisone">Endrisone (endrysone)</a></li> <li><a href="/wiki/Etiprednol" title="Etiprednol">Etiprednol</a> <ul><li><a href="/w/index.php?title=Etiprednol_dicloacetate&action=edit&redlink=1" class="new" title="Etiprednol dicloacetate (page does not exist)">Etiprednol dicloacetate (etiprednol dichloroacetate)</a></li></ul></li> <li><a href="/wiki/Fludrocortisone" title="Fludrocortisone">Fludrocortisone (fludrocortone)</a> <ul><li><a href="/wiki/Fludrocortisone_acetate" class="mw-redirect" title="Fludrocortisone acetate">Fludrocortisone acetate</a></li></ul></li> <li><a href="/wiki/Fluorometholone" title="Fluorometholone">Fluorometholone</a> <ul><li><a href="/wiki/Fluorometholone_acetate" title="Fluorometholone acetate">Fluorometholone acetate</a></li></ul></li> <li><a href="/wiki/Fluperolone" title="Fluperolone">Fluperolone</a> <ul><li><a href="/wiki/Fluperolone_acetate" title="Fluperolone acetate">Fluperolone acetate</a></li></ul></li> <li><a href="/wiki/Fluprednisolone" title="Fluprednisolone">Fluprednisolone</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Fluprednisolone_esters" title="List of corticosteroid esters">Fluprednisolone esters</a></li></ul></li> <li><a href="/wiki/Halopredone" title="Halopredone">Halopredone</a> <ul><li><a href="/w/index.php?title=Halopredone_acetate&action=edit&redlink=1" class="new" title="Halopredone acetate (page does not exist)">Halopredone acetate (halopredone diacetate)</a></li></ul></li> <li><a href="/wiki/Isoflupredone" title="Isoflupredone">Isoflupredone (9α-fluoroprednisolone)</a> <ul><li><a href="/w/index.php?title=Isoflupredone_acetate&action=edit&redlink=1" class="new" title="Isoflupredone acetate (page does not exist)">Isoflupredone acetate</a></li></ul></li> <li><a href="/wiki/Loteprednol" title="Loteprednol">Loteprednol</a></li> <li><a href="/wiki/Mazipredone" title="Mazipredone">Mazipredone (depersolone)</a></li> <li><a href="/wiki/Medrysone" title="Medrysone">Medrysone</a></li> <li><a href="/wiki/Methylprednisolone" title="Methylprednisolone">Methylprednisolone</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Methylprednisolone_esters" title="List of corticosteroid esters">Methylprednisolone esters</a></li></ul></li> <li><a href="/wiki/Prebediolone" class="mw-redirect" title="Prebediolone">Prebediolone</a> <ul><li><a href="/wiki/Prebediolone_acetate" title="Prebediolone acetate">Prebediolone acetate</a></li></ul></li> <li><a href="/wiki/Prednisolone" title="Prednisolone">Prednisolone</a> <ul><li><a href="/wiki/Prednazate" title="Prednazate">Prednazate</a></li> <li><a href="/wiki/Prednazoline" title="Prednazoline">Prednazoline</a></li> <li><a href="/wiki/Prednicarbate" title="Prednicarbate">Prednicarbate (prednisolone ethylcarbonate propionate)</a></li> <li><a href="/wiki/Prednimustine" title="Prednimustine">Prednimustine</a></li> <li><a href="/wiki/Prednisolamate" title="Prednisolamate">Prednisolamate (prednisolone diethylaminoacetate)</a></li> <li><a href="/wiki/List_of_corticosteroid_esters#Prednisolone_esters" title="List of corticosteroid esters">Prednisolone esters</a></li></ul></li> <li><a href="/wiki/Prednisone" title="Prednisone">Prednisone</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Prednisone_esters" title="List of corticosteroid esters">Prednisone esters</a></li></ul></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a> <ul><li><a href="/wiki/Pregnenolone_acetate" title="Pregnenolone acetate">Pregnenolone acetate</a></li> <li><a href="/wiki/Pregnenolone_succinate" title="Pregnenolone succinate">Pregnenolone succinate (pregnenolone hemisuccinate)</a></li></ul></li> <li><a href="/wiki/Resocortol" title="Resocortol">Resocortol</a></li> <li><a href="/wiki/Tipredane" title="Tipredane">Tipredane</a></li> <li><a href="/wiki/Tixocortol" title="Tixocortol">Tixocortol</a> <ul><li><a href="/wiki/Butixocort" title="Butixocort">Butixocort (tixocortol butyrate)</a> <ul><li><a href="/w/index.php?title=Butixocort_propionate&action=edit&redlink=1" class="new" title="Butixocort propionate (page does not exist)">Butixocort propionate</a></li></ul></li> <li><a href="/wiki/Tixocortol_pivalate" title="Tixocortol pivalate">Tixocortol pivalate</a></li></ul></li></ul> <ul><li><i>Methasones and related (16-substituted):</i> <a href="/wiki/16%CE%B1-Methyl-11-oxoprednisolone" title="16α-Methyl-11-oxoprednisolone">16α-Methyl-11-oxoprednisolone</a></li> <li><a href="/wiki/Alclometasone" title="Alclometasone">Alclometasone</a> <ul><li><a href="/wiki/Alclometasone_dipropionate" title="Alclometasone dipropionate">Alclometasone dipropionate</a></li></ul></li> <li><a href="/wiki/Amelometasone" title="Amelometasone">Amelometasone</a></li> <li><a href="/wiki/Beclometasone" title="Beclometasone">Beclometasone (beclomethasone)</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Beclometasone_esters" title="List of corticosteroid esters">Beclometasone esters</a></li></ul></li> <li><a href="/wiki/Betamethasone" title="Betamethasone">Betamethasone (betametasone)</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Betamethasone_esters" title="List of corticosteroid esters">Betamethasone esters</a></li> <li><a href="/wiki/Cortobenzolone" title="Cortobenzolone">Cortobenzolone (betamethasone salicylate)</a></li></ul></li> <li><a href="/wiki/Ciclometasone" title="Ciclometasone">Ciclometasone (ciclomethasone, cyclomethasone)</a></li> <li><a href="/wiki/Clobetasol" title="Clobetasol">Clobetasol</a> <ul><li><a href="/wiki/Clobetasol_propionate" title="Clobetasol propionate">Clobetasol propionate</a></li></ul></li> <li><a href="/wiki/Clobetasone" title="Clobetasone">Clobetasone</a> <ul><li><a href="/wiki/Clobetasone_butyrate" title="Clobetasone butyrate">Clobetasone butyrate</a></li></ul></li> <li><a href="/wiki/Clocortolone" title="Clocortolone">Clocortolone</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Clocortolone_esters" title="List of corticosteroid esters">Clocortolone esters</a></li></ul></li> <li><a href="/wiki/Cloticasone" title="Cloticasone">Cloticasone</a> <ul><li><a href="/w/index.php?title=Cloticasone_propionate&action=edit&redlink=1" class="new" title="Cloticasone propionate (page does not exist)">Cloticasone propionate</a></li></ul></li> <li><a href="/wiki/Cormetasone" title="Cormetasone">Cormetasone (cormethasone)</a> <ul><li><a href="/w/index.php?title=Cormetasone_acetate&action=edit&redlink=1" class="new" title="Cormetasone acetate (page does not exist)">Cormetasone acetate</a></li></ul></li> <li><a href="/wiki/Descinolone" title="Descinolone">Descinolone</a></li> <li><a href="/wiki/Desoximetasone" title="Desoximetasone">Desoximetasone (desoxymethasone)</a></li> <li><a href="/wiki/Dexamethasone" title="Dexamethasone">Dexamethasone (dexametasone)</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Dexamethasone_esters" title="List of corticosteroid esters">Dexamethasone esters</a></li></ul></li> <li><a href="/wiki/Diflorasone" title="Diflorasone">Diflorasone</a> <ul><li><a href="/wiki/Diflorasone_diacetate" title="Diflorasone diacetate">Diflorasone diacetate</a></li></ul></li> <li><a href="/wiki/Diflucortolone" title="Diflucortolone">Diflucortolone</a> <ul><li><a href="/w/index.php?title=Diflucortolone_pivalate&action=edit&redlink=1" class="new" title="Diflucortolone pivalate (page does not exist)">Diflucortolone pivalate</a></li> <li><a href="/wiki/Diflucortolone_valerate" title="Diflucortolone valerate">Diflucortolone valerate</a></li></ul></li> <li><a href="/wiki/Dimesone" title="Dimesone">Dimesone</a> <ul><li><a href="/w/index.php?title=Dimesone_acetate&action=edit&redlink=1" class="new" title="Dimesone acetate (page does not exist)">Dimesone acetate</a></li></ul></li> <li><a href="/wiki/Doxibetasol" title="Doxibetasol">Doxibetasol (doxybetasol)</a></li> <li><a href="/wiki/Fluclorolone" title="Fluclorolone">Fluclorolone</a></li> <li><a href="/wiki/Flumetasone" title="Flumetasone">Flumetasone (flumethasone)</a> <ul><li><a href="/w/index.php?title=Flumetasone_acetate&action=edit&redlink=1" class="new" title="Flumetasone acetate (page does not exist)">Flumetasone acetate</a></li> <li><a href="/wiki/Flumetasone_pivalate" title="Flumetasone pivalate">Flumetasone pivalate</a></li></ul></li> <li><a href="/wiki/Fluocinolone" title="Fluocinolone">Fluocinolone</a></li> <li><a href="/wiki/Fluocortin" title="Fluocortin">Fluocortin</a> <ul><li><a href="/wiki/Fluocortin_butyl" title="Fluocortin butyl">Fluocortin butyl (fluocortin butylate)</a></li></ul></li> <li><a href="/wiki/Fluocortolone" title="Fluocortolone">Fluocortolone</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Fluocortolone_esters" title="List of corticosteroid esters">Fluocortolone esters</a></li></ul></li> <li><a href="/wiki/Fluprednidene" title="Fluprednidene">Fluprednidene (fluprednylidene)</a> <ul><li><a href="/wiki/Fluprednidene_acetate" title="Fluprednidene acetate">Fluprednidene acetate</a></li></ul></li> <li>Fluticasone <ul><li><a href="/wiki/Fluticasone_furoate" title="Fluticasone furoate">Fluticasone furoate</a></li> <li><a href="/wiki/Fluticasone_propionate" title="Fluticasone propionate">Fluticasone propionate</a></li></ul></li> <li><a href="/wiki/Halocortolone" title="Halocortolone">Halocortolone</a></li> <li><a href="/wiki/Halometasone" title="Halometasone">Halometasone</a></li> <li><a href="/wiki/Icometasone" title="Icometasone">Icometasone</a> <ul><li><a href="/w/index.php?title=Icometasone_enbutate&action=edit&redlink=1" class="new" title="Icometasone enbutate (page does not exist)">Icometasone enbutate (icometasone butyrate acetate)</a></li></ul></li> <li><a href="/wiki/Isoprednidene" title="Isoprednidene">Isoprednidene</a></li> <li><a href="/wiki/Locicortolone" title="Locicortolone">Locicortolone (locicortone)</a> <ul><li><a href="/w/index.php?title=Locicortolone_dicibate&action=edit&redlink=1" class="new" title="Locicortolone dicibate (page does not exist)">Locicortolone dicibate (locicortone dicibate)</a></li></ul></li> <li><a href="/wiki/Meclorisone" title="Meclorisone">Meclorisone</a> <ul><li><a href="/w/index.php?title=Meclorisone_dibutyrate&action=edit&redlink=1" class="new" title="Meclorisone dibutyrate (page does not exist)">Meclorisone dibutyrate</a></li></ul></li> <li><a href="/wiki/Meprednisone" title="Meprednisone">Meprednisone (methylprednisone)</a> <ul><li><a href="/w/index.php?title=Meprednisone_acetate&action=edit&redlink=1" class="new" title="Meprednisone acetate (page does not exist)">Meprednisone acetate</a></li> <li><a href="/w/index.php?title=Meprednisone_hydrogen_succinate&action=edit&redlink=1" class="new" title="Meprednisone hydrogen succinate (page does not exist)">Meprednisone hydrogen succinate (methylprednisone hemisuccinate)</a></li></ul></li> <li><a href="/wiki/Mometasone" title="Mometasone">Mometasone</a> <ul><li><a href="/wiki/Mometasone_furoate" class="mw-redirect" title="Mometasone furoate">Mometasone furoate</a></li></ul></li> <li><a href="/wiki/Paramethasone" title="Paramethasone">Paramethasone</a> <ul><li><a href="/wiki/Paramethasone_acetate" title="Paramethasone acetate">Paramethasone acetate</a></li> <li><a href="/w/index.php?title=Paramethasone_disodium_phosphate&action=edit&redlink=1" class="new" title="Paramethasone disodium phosphate (page does not exist)">Paramethasone disodium phosphate</a></li> <li><a href="/w/index.php?title=Paramethasone_phosphate&action=edit&redlink=1" class="new" title="Paramethasone phosphate (page does not exist)">Paramethasone phosphate</a></li></ul></li> <li><a href="/wiki/Prednylidene" title="Prednylidene">Prednylidene</a> <ul><li><a href="/w/index.php?title=Prednylidene_diethylaminoacetate&action=edit&redlink=1" class="new" title="Prednylidene diethylaminoacetate (page does not exist)">Prednylidene diethylaminoacetate</a></li></ul></li> <li><a href="/wiki/Rimexolone" title="Rimexolone">Rimexolone</a></li> <li><a href="/wiki/Ticabesone" title="Ticabesone">Ticabesone</a> <ul><li><a href="/w/index.php?title=Ticabesone_propionate&action=edit&redlink=1" class="new" title="Ticabesone propionate (page does not exist)">Ticabesone propionate</a></li></ul></li> <li><a href="/wiki/Timobesone" title="Timobesone">Timobesone</a> <ul><li><a href="/w/index.php?title=Timobesone_acetate&action=edit&redlink=1" class="new" title="Timobesone acetate (page does not exist)">Timobesone acetate</a></li></ul></li> <li><a href="/wiki/Triamcinolone" title="Triamcinolone">Triamcinolone</a> <ul><li><a href="/wiki/Triamcinolone_diacetate" title="Triamcinolone diacetate">Triamcinolone diacetate</a></li></ul></li> <li><a href="/wiki/Ulobetasol" title="Ulobetasol">Ulobetasol (halobetasol)</a> <ul><li><a href="/wiki/Ulobetasol_propionate" title="Ulobetasol propionate">Ulobetasol propionate</a></li></ul></li> <li><a href="/wiki/Vamorolone" title="Vamorolone">Vamorolone</a></li></ul> <ul><li><i>Cyclic ketals (16,17-cyclized):</i> <a href="/wiki/Acrocinonide" title="Acrocinonide">Acrocinonide (triamcinolone acroleinide)</a></li> <li><a href="/wiki/Amcinafal" title="Amcinafal">Amcinafal (triamcinolone pentanonide)</a></li> <li><a href="/wiki/Amcinafide" title="Amcinafide">Amcinafide (triamcinolone acetophenide)</a></li> <li><a href="/wiki/Amcinonide" title="Amcinonide">Amcinonide (triamcinolone acetate cyclopentanonide)</a></li> <li><a href="/wiki/Budesonide" title="Budesonide">Budesonide</a></li> <li><a href="/wiki/Ciclesonide" title="Ciclesonide">Ciclesonide</a></li> <li><a href="/wiki/Cicortonide" title="Cicortonide">Cicortonide</a></li> <li><a href="/wiki/Deflazacort" title="Deflazacort">Deflazacort (azacort)</a></li> <li><a href="/wiki/Descinolone_acetonide" title="Descinolone acetonide">Descinolone acetonide</a></li> <li><a href="/wiki/Desonide" title="Desonide">Desonide (hydroxyprednisolone acetonide)</a> <ul><li><a href="/w/index.php?title=Desonide_disodium_phosphate&action=edit&redlink=1" class="new" title="Desonide disodium phosphate (page does not exist)">Desonide disodium phosphate</a></li> <li><a href="/w/index.php?title=Desonide_pivalate&action=edit&redlink=1" class="new" title="Desonide pivalate (page does not exist)">Desonide pivalate</a></li></ul></li> <li><a href="/wiki/Dexbudesonide" title="Dexbudesonide">Dexbudesonide</a></li> <li><a href="/wiki/Drocinonide" title="Drocinonide">Drocinonide</a> <ul><li><a href="/w/index.php?title=Drocinonide_phosphate&action=edit&redlink=1" class="new" title="Drocinonide phosphate (page does not exist)">Drocinonide phosphate</a></li></ul></li> <li><a href="/wiki/Fluazacort" title="Fluazacort">Fluazacort</a></li> <li><a href="/wiki/Fluclorolone_acetonide" title="Fluclorolone acetonide">Fluclorolone acetonide (flucloronide)</a></li> <li><a href="/wiki/Fludroxycortide" title="Fludroxycortide">Fludroxycortide (flurandrenolone, flurandrenolide)</a></li> <li><a href="/wiki/Flumoxonide" title="Flumoxonide">Flumoxonide</a></li> <li><a href="/wiki/Flunisolide" title="Flunisolide">Flunisolide</a> <ul><li><a href="/w/index.php?title=Flunisolide_acetate&action=edit&redlink=1" class="new" title="Flunisolide acetate (page does not exist)">Flunisolide acetate</a></li></ul></li> <li><a href="/wiki/Fluocinolone_acetonide" title="Fluocinolone acetonide">Fluocinolone acetonide</a> <ul><li><a href="/wiki/Ciprocinonide" title="Ciprocinonide">Ciprocinonide (fluocinolone acetonide cyclopropylcarboxylate)</a></li> <li><a href="/wiki/Fluocinonide" title="Fluocinonide">Fluocinonide (fluocinolide, fluocinolone acetonide acetate)</a></li> <li><a href="/wiki/Procinonide" title="Procinonide">Procinonide (fluocinolone acetonide propionate)</a></li></ul></li> <li><a href="/wiki/Formocortal" title="Formocortal">Formocortal</a></li> <li><a href="/wiki/Halcinonide" title="Halcinonide">Halcinonide</a></li> <li><a href="/wiki/Itrocinonide" title="Itrocinonide">Itrocinonide</a></li> <li><a href="/wiki/Rofleponide" title="Rofleponide">Rofleponide</a> <ul><li><a href="/wiki/Rofleponide_palmitate" class="mw-redirect" title="Rofleponide palmitate">Rofleponide palmitate</a></li></ul></li> <li><a href="/wiki/Tralonide" title="Tralonide">Tralonide</a></li> <li><a href="/wiki/Triamcinolone_acetonide" title="Triamcinolone acetonide">Triamcinolone acetonide</a> <ul><li><a href="/wiki/Flupamesone" title="Flupamesone">Flupamesone (triamcinolone acetonide metembonate)</a></li> <li><a href="/wiki/List_of_corticosteroid_esters#Triamcinolone_acetonide_esters" title="List of corticosteroid esters">Triamcinolone acetonide esters</a></li></ul></li> <li><a href="/wiki/Triamcinolone_aminobenzal_benzamidoisobutyrate" title="Triamcinolone aminobenzal benzamidoisobutyrate">Triamcinolone aminobenzal benzamidoisobutyrate (TBI-PAB)</a></li> <li><a href="/wiki/Triclonide" title="Triclonide">Triclonide</a></li></ul> <ul><li><i>Others/atypical (other expanded steroid ring systems, homosteroids, and non-pregnane steroids):</i> <a href="/wiki/Cortisuzol" title="Cortisuzol">Cortisuzol</a></li> <li><a href="/wiki/Cortivazol" title="Cortivazol">Cortivazol</a></li> <li><a href="/wiki/Domoprednate" title="Domoprednate">Domoprednate</a></li> <li><a href="/wiki/Naflocort" title="Naflocort">Naflocort</a></li> <li><a href="/wiki/Nicocortonide" title="Nicocortonide">Nicocortonide</a> <ul><li><a href="/w/index.php?title=Nicocortonide_acetate&action=edit&redlink=1" class="new" title="Nicocortonide acetate (page does not exist)">Nicocortonide acetate</a></li></ul></li> <li><a href="/wiki/Nivacortol" title="Nivacortol">Nivacortol (nivazol)</a></li> <li><a href="/wiki/Oxisopred" title="Oxisopred">Oxisopred</a></li> <li><a href="/w/index.php?title=RU-26988&action=edit&redlink=1" class="new" title="RU-26988 (page does not exist)">RU-26988</a></li> <li><a href="/wiki/RU-28362" title="RU-28362">RU-28362</a></li></ul> <ul><li><i>Non-corticosteroids with some glucocorticoid activity:</i> <a href="/wiki/15%CE%B2-Hydroxycyproterone_acetate" title="15β-Hydroxycyproterone acetate">15β-Hydroxycyproterone acetate</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone</a></li> <li><a href="/wiki/Bromoketoprogesterone" title="Bromoketoprogesterone">Bromoketoprogesterone</a></li> <li><a href="/wiki/Chlormadinone_acetate" title="Chlormadinone acetate">Chlormadinone acetate</a></li> <li><a href="/wiki/Cyproterone" title="Cyproterone">Cyproterone</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Danazol" title="Danazol">Danazol</a></li> <li><a href="/wiki/Delmadinone_acetate" title="Delmadinone acetate">Delmadinone acetate</a></li> <li><a href="/wiki/Desogestrel" title="Desogestrel">Desogestrel</a></li> <li><a href="/wiki/DU-41165" title="DU-41165">DU-41165</a></li> <li><a href="/wiki/Etonogestrel" title="Etonogestrel">Etonogestrel</a></li> <li><a href="/wiki/Flugestone" title="Flugestone">Flugestone</a></li> <li><a href="/wiki/Flugestone_acetate" title="Flugestone acetate">Flugestone acetate (flurogestone acetate)</a></li> <li><a href="/wiki/Fluoromedroxyprogesterone_acetate" title="Fluoromedroxyprogesterone acetate">Fluoromedroxyprogesterone acetate</a></li> <li><a href="/wiki/Fluoxymesterone" title="Fluoxymesterone">Fluoxymesterone</a></li> <li><a href="/wiki/Gestodene" title="Gestodene">Gestodene</a></li> <li><a href="/wiki/Medrogestone" title="Medrogestone">Medrogestone</a></li> <li><a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">Medroxyprogesterone acetate</a></li> <li><a href="/wiki/Megestrol_acetate" title="Megestrol acetate">Megestrol acetate</a></li> <li><a href="/wiki/Metribolone" title="Metribolone">Metribolone</a></li> <li><a href="/wiki/Norgestomet" title="Norgestomet">Norgestomet</a></li> <li><a href="/wiki/Osaterone_acetate" title="Osaterone acetate">Osaterone acetate</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Promegestone" title="Promegestone">Promegestone</a></li> <li><a href="/wiki/RU-2309" title="RU-2309">RU-2309</a></li> <li><a href="/wiki/Quingestrone" title="Quingestrone">Quingestrone</a></li> <li><a href="/wiki/Segesterone_acetate" title="Segesterone acetate">Segesterone acetate (nestorone)</a></li> <li><a href="/wiki/Tetrahydrogestrinone" title="Tetrahydrogestrinone">Tetrahydrogestrinone</a></li></ul> <ul><li><i>Nonsteroidal glucocorticoids:</i> <a href="/wiki/AZD-5423" title="AZD-5423">AZD-5423</a></li> <li><a href="/w/index.php?title=GSK-9027&action=edit&redlink=1" class="new" title="GSK-9027 (page does not exist)">GSK-9027</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Mixed<br />(<a href="/wiki/Selective_glucocorticoid_receptor_agonists" class="mw-redirect" title="Selective glucocorticoid receptor agonists"><abbr title="Selective glucocorticoid receptor agonists">SEGRMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Selective glucocorticoid receptor agonists</span>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Dagrocorat" title="Dagrocorat">Dagrocorat</a></li> <li><a href="/wiki/Fosdagrocorat" title="Fosdagrocorat">Fosdagrocorat</a></li> <li><a href="/wiki/Mapracorat" title="Mapracorat">Mapracorat</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center"><a href="/wiki/Antiglucocorticoid" title="Antiglucocorticoid">Antagonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/7%CE%B1-Hydroxy-DHEA" title="7α-Hydroxy-DHEA">7α-Hydroxy-DHEA</a></li> <li><a href="/wiki/17%CE%B1-Methylprogesterone" title="17α-Methylprogesterone">17α-Methylprogesterone</a></li> <li><a href="/wiki/Aglepristone" title="Aglepristone">Aglepristone</a></li> <li><a href="/wiki/Asoprisnil" title="Asoprisnil">Asoprisnil</a></li> <li><a href="/wiki/Asoprisnil_ecamate" title="Asoprisnil ecamate">Asoprisnil ecamate</a></li> <li><a href="/w/index.php?title=C108297&action=edit&redlink=1" class="new" title="C108297 (page does not exist)">C108297</a></li> <li><a href="/w/index.php?title=C113176&action=edit&redlink=1" class="new" title="C113176 (page does not exist)">C113176</a></li> <li><a href="/w/index.php?title=CORT-108297&action=edit&redlink=1" class="new" title="CORT-108297 (page does not exist)">CORT-108297</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/w/index.php?title=Dazucorilant&action=edit&redlink=1" class="new" title="Dazucorilant (page does not exist)">Dazucorilant</a></li> <li><a href="/w/index.php?title=Exicorilant&action=edit&redlink=1" class="new" title="Exicorilant (page does not exist)">Exicorilant (CORT-125281)</a></li> <li><a href="/wiki/Guggulsterone" title="Guggulsterone">Guggulsterone</a></li> <li><a href="/wiki/Ketoconazole" title="Ketoconazole">Ketoconazole</a></li> <li><a href="/wiki/Lilopristone" title="Lilopristone">Lilopristone</a></li> <li><a href="/w/index.php?title=LLY-2707&action=edit&redlink=1" class="new" title="LLY-2707 (page does not exist)">LLY-2707</a></li> <li><a href="/wiki/Metapristone" title="Metapristone">Metapristone (RU-42633)</a></li> <li><a href="/wiki/Miconazole" title="Miconazole">Miconazole</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone (RU-486)</a></li> <li><a href="/wiki/Miricorilant" title="Miricorilant">Miricorilant (CORT-118335)</a></li> <li><a href="/wiki/Onapristone" title="Onapristone">Onapristone</a></li> <li><a href="/w/index.php?title=ORG-34116&action=edit&redlink=1" class="new" title="ORG-34116 (page does not exist)">ORG-34116</a></li> <li><a href="/w/index.php?title=ORG-34517&action=edit&redlink=1" class="new" title="ORG-34517 (page does not exist)">ORG-34517 (SCH-900636)</a></li> <li><a href="/w/index.php?title=Org_34850&action=edit&redlink=1" class="new" title="Org 34850 (page does not exist)">ORG-34850</a></li> <li><a href="/wiki/Pregnenolone_16%CE%B1-carbonitrile" title="Pregnenolone 16α-carbonitrile">Pregnenolone 16α-carbonitrile</a></li> <li><a href="/wiki/Relacorilant" title="Relacorilant">Relacorilant (CORT-125134)</a></li> <li><a href="/wiki/RTI_3021%E2%80%93012" class="mw-redirect" title="RTI 3021–012">RTI 3021–012</a></li> <li><a href="/w/index.php?title=RTI_3021%E2%80%93022&action=edit&redlink=1" class="new" title="RTI 3021–022 (page does not exist)">RTI 3021–022</a></li> <li><a href="/wiki/Telapristone" title="Telapristone">Telapristone</a></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li> <li><a href="/wiki/Toripristone" title="Toripristone">Toripristone</a></li> <li><a href="/wiki/Ulipristal_acetate" title="Ulipristal acetate">Ulipristal acetate</a></li> <li><a href="/w/index.php?title=Zavacorilant&action=edit&redlink=1" class="new" title="Zavacorilant (page does not exist)">Zavacorilant</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Others</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Antisense oligonucleotides:</i> <a href="/wiki/IONIS-GCCRRx" title="IONIS-GCCRRx">IONIS-GCCR<sub>Rx</sub> (ISIS-426115)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Glucocorticoids_and_antiglucocorticoids" title="Template:Glucocorticoids and antiglucocorticoids">Glucocorticoids and antiglucocorticoids</a></dd> <dd><a href="/wiki/Template:Mineralocorticoid_receptor_modulators" title="Template:Mineralocorticoid receptor modulators">Mineralocorticoid receptor modulators</a></dd> <dd><a href="/wiki/List_of_corticosteroids" title="List of corticosteroids">List of corticosteroids</a></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Mineralocorticoid_receptor_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Mineralocorticoid_receptor_modulators" title="Template:Mineralocorticoid receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Mineralocorticoid_receptor_modulators" title="Template talk:Mineralocorticoid receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Mineralocorticoid_receptor_modulators" title="Special:EditPage/Template:Mineralocorticoid receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Mineralocorticoid_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Mineralocorticoid_receptor" title="Mineralocorticoid receptor">Mineralocorticoid receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Mineralocorticoid_receptor" title="Mineralocorticoid receptor"><abbr title="Mineralocorticoid receptor">MR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Mineralocorticoid receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/11-Dehydrocorticosterone" title="11-Dehydrocorticosterone">11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone)</a> <ul><li><a href="/w/index.php?title=11-Dehydrocorticosterone_acetate&action=edit&redlink=1" class="new" title="11-Dehydrocorticosterone acetate (page does not exist)">11-Dehydrocorticosterone acetate</a></li></ul></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone (desoxycortone, deoxycortone, desoxycorticosterone)</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Desoxycortone_esters" title="List of corticosteroid esters">Desoxycortone esters</a></li></ul></li> <li><a href="/wiki/11-Deoxycortisol" title="11-Deoxycortisol">11-Deoxycortisol (cortodoxone, cortexolone)</a> <ul><li><a href="/wiki/Cortifen" title="Cortifen">Cortifen (cortiphen, kortifen)</a></li> <li><a href="/w/index.php?title=Cortodoxone_acetate&action=edit&redlink=1" class="new" title="Cortodoxone acetate (page does not exist)">Cortodoxone acetate</a></li></ul></li> <li><a href="/wiki/11%CE%B2-Hydroxyprogesterone" title="11β-Hydroxyprogesterone">11β-Hydroxyprogesterone</a></li> <li><a href="/w/index.php?title=16%CE%B1,18-Dihydroxy-11-deoxycorticosterone&action=edit&redlink=1" class="new" title="16α,18-Dihydroxy-11-deoxycorticosterone (page does not exist)">16α,18-Dihydroxy-11-deoxycorticosterone</a></li> <li><a href="/w/index.php?title=17%CE%B1-Hydroxyaldosterone&action=edit&redlink=1" class="new" title="17α-Hydroxyaldosterone (page does not exist)">17α-Hydroxyaldosterone</a></li> <li><a href="/wiki/18-Hydroxy-11-deoxycorticosterone" title="18-Hydroxy-11-deoxycorticosterone">18-Hydroxy-11-deoxycorticosterone</a></li> <li><a href="/wiki/19-Norprogesterone" title="19-Norprogesterone">19-Norprogesterone</a></li> <li><a href="/wiki/Aldosterone" title="Aldosterone">Aldosterone</a></li> <li><a href="/wiki/Corticosterone" title="Corticosterone">Corticosterone</a> <ul><li><a href="/w/index.php?title=Corticosterone_acetate&action=edit&redlink=1" class="new" title="Corticosterone acetate (page does not exist)">Corticosterone acetate</a></li> <li><a href="/w/index.php?title=Corticosterone_benzoate&action=edit&redlink=1" class="new" title="Corticosterone benzoate (page does not exist)">Corticosterone benzoate</a></li></ul></li> <li><a href="/wiki/Cortisol" title="Cortisol">Cortisol</a> (<a href="/wiki/Hydrocortisone" title="Hydrocortisone">hydrocortisone</a>) <ul><li><a href="/wiki/Benzodrocortisone" title="Benzodrocortisone">Benzodrocortisone (hydrocortisone benzoate)</a></li> <li><a href="/wiki/Hydrocortamate" title="Hydrocortamate">Hydrocortamate (hydrocortisone diethylaminoacetate)</a></li> <li><a href="/wiki/List_of_corticosteroid_esters#Hydrocortisone_esters" title="List of corticosteroid esters">Hydrocortisone esters</a></li></ul></li> <li><a href="/wiki/Cortisone" title="Cortisone">Cortisone</a> <ul><li><a href="/wiki/Cortisone_acetate" title="Cortisone acetate">Cortisone acetate</a></li></ul></li> <li><a href="/wiki/Fludrocortisone" title="Fludrocortisone">Fludrocortisone (fludrocortone)</a> <ul><li><a href="/wiki/Fludrocortisone_acetate" class="mw-redirect" title="Fludrocortisone acetate">Fludrocortisone acetate</a></li></ul></li> <li><a href="/wiki/Mometasone" title="Mometasone">Mometasone</a> <ul><li><a href="/wiki/Mometasone_furoate" class="mw-redirect" title="Mometasone furoate">Mometasone furoate</a></li></ul></li> <li><a href="/wiki/Prednisolone" title="Prednisolone">Prednisolone</a> <ul><li><a href="/wiki/Prednazate" title="Prednazate">Prednazate</a></li> <li><a href="/wiki/Prednazoline" title="Prednazoline">Prednazoline</a></li> <li><a href="/wiki/Prednicarbate" title="Prednicarbate">Prednicarbate (prednisolone ethylcarbonate propionate)</a></li> <li><a href="/wiki/Prednimustine" title="Prednimustine">Prednimustine</a></li> <li><a href="/wiki/Prednisolamate" title="Prednisolamate">Prednisolamate (prednisolone diethylaminoacetate)</a></li> <li><a href="/wiki/List_of_corticosteroid_esters#Prednisolone_esters" title="List of corticosteroid esters">Prednisolone esters</a></li></ul></li> <li><a href="/wiki/Prednisone" title="Prednisone">Prednisone</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Prednisone_esters" title="List of corticosteroid esters">Prednisone esters</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Steroidal:</i> <a href="/wiki/6%CE%B2-Hydroxy-7%CE%B1-thiomethylspironolactone" title="6β-Hydroxy-7α-thiomethylspironolactone">6β-Hydroxy-7α-thiomethylspironolactone</a></li> <li><a href="/w/index.php?title=7%CE%B1-Acetylthio-17%CE%B1-hydroxyprogesterone&action=edit&redlink=1" class="new" title="7α-Acetylthio-17α-hydroxyprogesterone (page does not exist)">7α-Acetylthio-17α-hydroxyprogesterone</a></li> <li><a href="/wiki/7%CE%B1-Thiomethylspironolactone" title="7α-Thiomethylspironolactone">7α-Thiomethylspironolactone (SC-26519)</a></li> <li><a href="/wiki/7%CE%B1-Thioprogesterone" title="7α-Thioprogesterone">7α-Thioprogesterone (SC-8365)</a></li> <li><a href="/wiki/7%CE%B1-Thiospironolactone" title="7α-Thiospironolactone">7α-Thiospironolactone (SC-24813)</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyprogesterone" title="16α-Hydroxyprogesterone">16α-Hydroxyprogesterone</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone (hydroxyprogesterone)</a></li> <li><a href="/wiki/18-Deoxyaldosterone" title="18-Deoxyaldosterone">18-Deoxyaldosterone</a></li> <li><a href="/w/index.php?title=18,19-Dinorprogesterone&action=edit&redlink=1" class="new" title="18,19-Dinorprogesterone (page does not exist)">18,19-Dinorprogesterone</a></li> <li><a href="/wiki/Potassium_canrenoate" title="Potassium canrenoate">Canrenoate potassium (potassium canrenoate)</a></li> <li><a href="/wiki/Canrenoic_acid" title="Canrenoic acid">Canrenoic acid (canrenoate)</a></li> <li><a href="/wiki/Canrenone" title="Canrenone">Canrenone (canrenoate y-lactone)</a></li> <li><a href="/wiki/Dicirenone" title="Dicirenone">Dicirenone</a></li> <li><a href="/wiki/Dimethisterone" title="Dimethisterone">Dimethisterone</a></li> <li><a href="/wiki/Drospirenone" title="Drospirenone">Drospirenone</a></li> <li><a href="/wiki/Dydrogesterone" title="Dydrogesterone">Dydrogesterone</a></li> <li><a href="/wiki/Eplerenone" title="Eplerenone">Eplerenone</a></li> <li><a href="/wiki/Gestodene" title="Gestodene">Gestodene</a></li> <li><a href="/wiki/Guggulsterone" title="Guggulsterone">Guggulsterone</a></li> <li><a href="/wiki/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">Hydroxyprogesterone caproate</a></li> <li><a href="/wiki/Medrogestone" title="Medrogestone">Medrogestone</a></li> <li><a href="/wiki/Mespirenone" title="Mespirenone">Mespirenone</a></li> <li><a href="/wiki/Metribolone" title="Metribolone">Metribolone</a></li> <li><a href="/wiki/Mexrenoate_potassium" title="Mexrenoate potassium">Mexrenoate potassium</a></li> <li><a href="/wiki/Mexrenoic_acid" title="Mexrenoic acid">Mexrenoic acid (mexrenoate)</a></li> <li><a href="/wiki/Mexrenone" title="Mexrenone">Mexrenone</a></li> <li><a href="/wiki/Oxprenoic_acid" title="Oxprenoic acid">Oxprenoic acid (oxprenoate)</a></li> <li><a href="/wiki/Oxprenoate_potassium" title="Oxprenoate potassium">Oxprenoate potassium (RU-28318)</a></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Prorenoate_potassium" title="Prorenoate potassium">Prorenoate potassium</a></li> <li><a href="/wiki/Prorenoic_acid" title="Prorenoic acid">Prorenoic acid (prorenoate)</a></li> <li><a href="/wiki/Prorenone" title="Prorenone">Prorenone</a></li> <li><a href="/w/index.php?title=RO-14-9012&action=edit&redlink=1" class="new" title="RO-14-9012 (page does not exist)">RO-14-9012</a></li> <li><a href="/w/index.php?title=RU-26752&action=edit&redlink=1" class="new" title="RU-26752 (page does not exist)">RU-26752</a></li> <li><a href="/wiki/SC-5233" title="SC-5233">SC-5233 (spirolactone)</a></li> <li><a href="/wiki/SC-8109" title="SC-8109">SC-8109</a></li> <li><a href="/w/index.php?title=SC-11927&action=edit&redlink=1" class="new" title="SC-11927 (page does not exist)">SC-11927 (CS-1)</a></li> <li><a href="/w/index.php?title=SC-19886&action=edit&redlink=1" class="new" title="SC-19886 (page does not exist)">SC-19886</a></li> <li><a href="/w/index.php?title=SC-27169&action=edit&redlink=1" class="new" title="SC-27169 (page does not exist)">SC-27169</a></li> <li><a href="/wiki/Spirorenone" title="Spirorenone">Spirorenone</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/wiki/Spiroxasone" title="Spiroxasone">Spiroxasone</a></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li> <li><a href="/wiki/Trimegestone" title="Trimegestone">Trimegestone</a></li> <li><a href="/wiki/Vamorolone" title="Vamorolone">Vamorolone</a></li> <li><a href="/w/index.php?title=ZK-91587&action=edit&redlink=1" class="new" title="ZK-91587 (page does not exist)">ZK-91587</a></li> <li><a href="/w/index.php?title=ZK-97894&action=edit&redlink=1" class="new" title="ZK-97894 (page does not exist)">ZK-97894</a></li></ul> <ul><li><i>Nonsteroidal:</i> <a href="/wiki/Amlodipine" title="Amlodipine">Amlodipine</a></li> <li><a href="/wiki/Apararenone" title="Apararenone">Apararenone</a></li> <li><a href="/wiki/Benidipine" title="Benidipine">Benidipine</a></li> <li><a href="/w/index.php?title=BR-4628&action=edit&redlink=1" class="new" title="BR-4628 (page does not exist)">BR-4628</a></li> <li><a href="/wiki/Esaxerenone" title="Esaxerenone">Esaxerenone</a></li> <li><a href="/wiki/Felodipine" title="Felodipine">Felodipine</a></li> <li><a href="/wiki/Finerenone" title="Finerenone">Finerenone</a></li> <li><a href="/wiki/Miricorilant" title="Miricorilant">Miricorilant (CORT-118335)</a></li> <li><a href="/wiki/Nifedipine" title="Nifedipine">Nifedipine</a></li> <li><a href="/wiki/Nimodipine" title="Nimodipine">Nimodipine</a></li> <li><a href="/wiki/Nitrendipine" title="Nitrendipine">Nitrendipine</a></li> <li><a href="/wiki/Ocedurenone" title="Ocedurenone">Ocedurenone</a></li> <li><a href="/w/index.php?title=PF-03882845&action=edit&redlink=1" class="new" title="PF-03882845 (page does not exist)">PF-03882845</a></li> <li><a href="/w/index.php?title=SM-368229&action=edit&redlink=1" class="new" title="SM-368229 (page does not exist)">SM-368229</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Mineralocorticoids_and_antimineralocorticoids" title="Template:Mineralocorticoids and antimineralocorticoids">Mineralocorticoids and antimineralocorticoids</a></dd> <dd><a href="/wiki/Template:Glucocorticoid_receptor_modulators" title="Template:Glucocorticoid receptor modulators">Glucocorticoid receptor modulators</a></dd> <dd><a href="/wiki/List_of_corticosteroids" title="List of corticosteroids">List of corticosteroids</a></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Progesterone_receptor_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Progesterone_receptor_modulators" title="Template:Progesterone receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Progesterone_receptor_modulators" title="Template talk:Progesterone receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Progesterone_receptor_modulators" title="Special:EditPage/Template:Progesterone receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Progesterone_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Progesterone_receptor" title="Progesterone receptor">Progesterone receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Progesterone_receptor" title="Progesterone receptor"><abbr title="Progesterone receptor">PR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Progesterone receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Progesterone derivatives:</i> <a href="/wiki/3%CE%B2-Dihydroprogesterone" title="3β-Dihydroprogesterone">3β-Dihydroprogesterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">5α-Dihydroprogesterone</a></li> <li><a href="/wiki/6%CE%B1-Methylprogesterone" title="6α-Methylprogesterone">6α-Methylprogesterone</a></li> <li><a href="/wiki/9%CE%B1-Bromo-11-ketoprogesterone" class="mw-redirect" title="9α-Bromo-11-ketoprogesterone">9α-Bromo-11-ketoprogesterone</a></li> <li><a href="/wiki/11-Dehydroprogesterone" title="11-Dehydroprogesterone">11-Dehydroprogesterone</a></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyprogesterone" title="16α-Hydroxyprogesterone">16α-Hydroxyprogesterone</a></li> <li><a href="/w/index.php?title=17%CE%B1-Methyl-11-deoxycorticosterone_acetate&action=edit&redlink=1" class="new" title="17α-Methyl-11-deoxycorticosterone acetate (page does not exist)">17α-Methyl-11-deoxycorticosterone acetate</a></li> <li><a href="/wiki/20%CE%B1-Dihydroprogesterone" title="20α-Dihydroprogesterone">20α-Dihydroprogesterone</a></li> <li><a href="/wiki/20%CE%B2-Dihydroprogesterone" title="20β-Dihydroprogesterone">20β-Dihydroprogesterone</a></li> <li><a href="/wiki/Dimepregnen" title="Dimepregnen">Dimepregnen</a></li> <li><a href="/wiki/Diosgenin" title="Diosgenin">Diosgenin</a></li> <li><a href="/wiki/P1-185" title="P1-185">P1-185</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Progesterone_3-acetyl_enol_ether" title="Progesterone 3-acetyl enol ether">Progesterone 3-acetyl enol ether</a></li> <li><a href="/wiki/Quingestrone" title="Quingestrone">Quingestrone</a></li></ul> <ul><li><i>Retroprogesterone derivatives:</i> <a href="/wiki/20%CE%B1-Dihydrodydrogesterone" title="20α-Dihydrodydrogesterone">20α-Dihydrodydrogesterone</a></li> <li><a href="/wiki/20%CE%B1-Dihydrotrengestone" title="20α-Dihydrotrengestone">20α-Dihydrotrengestone</a></li> <li><a href="/wiki/DU-41164" title="DU-41164">DU-41164</a></li> <li><a href="/wiki/DU-41165" title="DU-41165">DU-41165</a></li> <li><a href="/wiki/Dydrogesterone" title="Dydrogesterone">Dydrogesterone</a></li> <li><a href="/wiki/Retroprogesterone" title="Retroprogesterone">Retroprogesterone</a></li> <li><a href="/wiki/Ro_6-3129" title="Ro 6-3129">Ro 6-3129</a></li> <li><a href="/wiki/Trengestone" title="Trengestone">Trengestone</a></li></ul> <ul><li><i>17α-Substituted progesterone derivatives:</i> <a href="/wiki/6%CE%B1-Methyl-17%CE%B1-bromoprogesterone" title="6α-Methyl-17α-bromoprogesterone">6α-Methyl-17α-bromoprogesterone</a></li> <li><a href="/wiki/15%CE%B2-Hydroxycyproterone_acetate" title="15β-Hydroxycyproterone acetate">15β-Hydroxycyproterone acetate</a></li> <li><a href="/wiki/16-Methylene-17%CE%B1-hydroxyprogesterone_acetate" title="16-Methylene-17α-hydroxyprogesterone acetate">16-Methylene-17α-hydroxyprogesterone acetate</a></li> <li><a href="/wiki/17%CE%B1-Bromoprogesterone" title="17α-Bromoprogesterone">17α-Bromoprogesterone</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone (hydroxyprogesterone)</a></li> <li><a href="/wiki/17%CE%B1-Methylprogesterone" title="17α-Methylprogesterone">17α-Methylprogesterone</a></li> <li><a href="/wiki/Acetomepregenol" title="Acetomepregenol">Acetomepregenol (mepregenol diacetate)</a></li> <li><a href="/wiki/Algestone" title="Algestone">Algestone</a></li> <li><a href="/wiki/Algestone_acetonide" title="Algestone acetonide">Algestone acetonide</a></li> <li><a href="/wiki/Algestone_acetophenide" title="Algestone acetophenide">Algestone acetophenide</a></li> <li><a href="/wiki/Anagestone" title="Anagestone">Anagestone</a></li> <li><a href="/wiki/Anagestone_acetate" title="Anagestone acetate">Anagestone acetate</a></li> <li><a href="/w/index.php?title=Bromethenmadinone&action=edit&redlink=1" class="new" title="Bromethenmadinone (page does not exist)">Bromethenmadinone</a></li> <li><a href="/wiki/Bromethenmadinone_acetate" title="Bromethenmadinone acetate">Bromethenmadinone acetate</a></li> <li><a href="/wiki/Butagest" title="Butagest">Butagest (buterol)</a></li> <li><a href="/wiki/Chlormadinone" title="Chlormadinone">Chlormadinone</a></li> <li><a href="/wiki/Chlormadinone_acetate" title="Chlormadinone acetate">Chlormadinone acetate</a></li> <li><a href="/wiki/Chlormadinone_caproate" title="Chlormadinone caproate">Chlormadinone caproate</a></li> <li><a href="/w/index.php?title=Chlormethenmadinone&action=edit&redlink=1" class="new" title="Chlormethenmadinone (page does not exist)">Chlormethenmadinone</a></li> <li><a href="/wiki/Chlormethenmadinone_acetate" title="Chlormethenmadinone acetate">Chlormethenmadinone acetate</a></li> <li><a href="/wiki/Cismadinone" title="Cismadinone">Cismadinone</a></li> <li><a href="/wiki/Cismadinone_acetate" title="Cismadinone acetate">Cismadinone acetate</a></li> <li><a href="/wiki/Clogestone" title="Clogestone">Clogestone</a></li> <li><a href="/wiki/Clogestone_acetate" title="Clogestone acetate">Clogestone acetate</a></li> <li><a href="/wiki/Clomegestone" title="Clomegestone">Clomegestone</a></li> <li><a href="/wiki/Clomegestone_acetate" title="Clomegestone acetate">Clomegestone acetate</a></li> <li><a href="/wiki/Cymegesolate" title="Cymegesolate">Cymegesolate</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Delmadinone" title="Delmadinone">Delmadinone</a></li> <li><a href="/wiki/Delmadinone_acetate" title="Delmadinone acetate">Delmadinone acetate</a></li> <li><a href="/wiki/Edogestrone" title="Edogestrone">Edogestrone</a></li> <li><a href="/wiki/Flugestone" title="Flugestone">Flugestone</a></li> <li><a href="/wiki/Flugestone_acetate" title="Flugestone acetate">Flugestone acetate</a></li> <li><a href="/wiki/Fluorometholone" title="Fluorometholone">Fluorometholone</a></li> <li><a href="/wiki/Fluorometholone_acetate" title="Fluorometholone acetate">Fluorometholone acetate</a></li> <li><a href="/wiki/Flumedroxone" title="Flumedroxone">Flumedroxone</a></li> <li><a href="/wiki/Flumedroxone_acetate" title="Flumedroxone acetate">Flumedroxone acetate</a></li> <li><a href="/wiki/Fluoromedroxyprogesterone_acetate" title="Fluoromedroxyprogesterone acetate">Fluoromedroxyprogesterone acetate</a></li> <li><a href="/wiki/Gestaclone" title="Gestaclone">Gestaclone</a></li> <li><a href="/w/index.php?title=Gestobutanoyl&action=edit&redlink=1" class="new" title="Gestobutanoyl (page does not exist)">Gestobutanoyl</a></li> <li><a href="/wiki/Haloprogesterone" title="Haloprogesterone">Haloprogesterone</a></li> <li><a href="/wiki/Hydromadinone" title="Hydromadinone">Hydromadinone</a></li> <li><a href="/wiki/Hydromadinone_acetate" title="Hydromadinone acetate">Hydromadinone acetate</a></li> <li><a href="/wiki/Hydroxyprogesterone_acetate" title="Hydroxyprogesterone acetate">Hydroxyprogesterone acetate</a></li> <li><a href="/wiki/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">Hydroxyprogesterone caproate (hydroxyprogesterone hexanoate)</a></li> <li><a href="/wiki/Hydroxyprogesterone_heptanoate" title="Hydroxyprogesterone heptanoate">Hydroxyprogesterone heptanoate (hydroxyprogesterone enanthate)</a></li> <li><a href="/wiki/Hydroxyprogesterone_heptanoate_benzilic_acid_hydrazone" title="Hydroxyprogesterone heptanoate benzilic acid hydrazone">Hydroxyprogesterone heptanoate benzilic acid hydrazone</a></li> <li><a href="/wiki/Mecigestone" title="Mecigestone">Mecigestone (pentarane B)</a></li> <li><a href="/wiki/Medrogestone" title="Medrogestone">Medrogestone</a></li> <li><a href="/wiki/Medroxyprogesterone" title="Medroxyprogesterone">Medroxyprogesterone</a></li> <li><a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">Medroxyprogesterone acetate</a></li> <li><a href="/wiki/Medroxyprogesterone_caproate" title="Medroxyprogesterone caproate">Medroxyprogesterone caproate</a></li> <li><a href="/wiki/Megestrol" title="Megestrol">Megestrol</a></li> <li><a href="/wiki/Megestrol_acetate" title="Megestrol acetate">Megestrol acetate</a></li> <li><a href="/wiki/Megestrol_caproate" title="Megestrol caproate">Megestrol caproate</a></li> <li><a href="/wiki/Melengestrol" title="Melengestrol">Melengestrol</a></li> <li><a href="/wiki/Melengestrol_acetate" title="Melengestrol acetate">Melengestrol acetate</a></li> <li><a href="/wiki/Methenmadinone" title="Methenmadinone">Methenmadinone</a></li> <li><a href="/wiki/Methenmadinone_acetate" title="Methenmadinone acetate">Methenmadinone acetate</a></li> <li><a href="/wiki/Methenmadinone_caproate" title="Methenmadinone caproate">Methenmadinone caproate</a></li> <li><a href="/wiki/Mometasone" title="Mometasone">Mometasone</a></li> <li><a href="/wiki/Mometasone_furoate" class="mw-redirect" title="Mometasone furoate">Mometasone furoate</a></li> <li><a href="/wiki/Osaterone" title="Osaterone">Osaterone</a></li> <li><a href="/wiki/Osaterone_acetate" title="Osaterone acetate">Osaterone acetate</a></li> <li><a href="/wiki/Pentagestrone" title="Pentagestrone">Pentagestrone</a></li> <li><a href="/wiki/Pentagestrone_acetate" title="Pentagestrone acetate">Pentagestrone acetate</a></li> <li><a href="/wiki/Pentarane_A" title="Pentarane A">Pentarane A</a></li> <li><a href="/wiki/Proligestone" title="Proligestone">Proligestone</a></li> <li><a href="/wiki/Triamcinolone_acetonide" title="Triamcinolone acetonide">Triamcinolone acetonide</a></li></ul> <ul><li><i>19-Norprogesterone derivatives:</i> <a href="/wiki/17%CE%B1-Methyl-19-norprogesterone" title="17α-Methyl-19-norprogesterone">17α-Methyl-19-norprogesterone</a></li> <li><a href="/wiki/18-Methylsegesterone_acetate" title="18-Methylsegesterone acetate">18-Methylsegesterone acetate</a></li> <li><a href="/wiki/19-Norprogesterone" title="19-Norprogesterone">19-Norprogesterone</a></li> <li><a href="/wiki/Amadinone" title="Amadinone">Amadinone</a></li> <li><a href="/wiki/Amadinone_acetate" title="Amadinone acetate">Amadinone acetate</a></li> <li><a href="/wiki/Demegestone" title="Demegestone">Demegestone</a></li> <li><a href="/w/index.php?title=Fluoro_ethyl_norprogesterone&action=edit&redlink=1" class="new" title="Fluoro ethyl norprogesterone (page does not exist)">Fluoro ethyl norprogesterone</a></li> <li><a href="/w/index.php?title=Fluoro_furanyl_norprogesterone&action=edit&redlink=1" class="new" title="Fluoro furanyl norprogesterone (page does not exist)">Fluoro furanyl norprogesterone</a></li> <li><a href="/wiki/Gestadienol" title="Gestadienol">Gestadienol</a></li> <li><a href="/wiki/Gestadienol_acetate" title="Gestadienol acetate">Gestadienol acetate</a></li> <li><a href="/wiki/Gestonorone_acetate" title="Gestonorone acetate">Gestonorone acetate (gestronol acetate)</a></li> <li><a href="/wiki/Gestonorone_caproate" title="Gestonorone caproate">Gestonorone caproate (gestronol hexanoate)</a></li> <li><a href="/wiki/Gestronol" title="Gestronol">Gestronol (gestonorone)</a></li> <li><a href="/wiki/Nomegestrol" title="Nomegestrol">Nomegestrol</a></li> <li><a href="/wiki/Nomegestrol_acetate" title="Nomegestrol acetate">Nomegestrol acetate</a></li> <li><a href="/wiki/Norgestomet" title="Norgestomet">Norgestomet</a></li> <li><a href="/wiki/ORG-2058" title="ORG-2058">ORG-2058</a></li> <li><a href="/wiki/Oxogestone" title="Oxogestone">Oxogestone</a></li> <li><a href="/wiki/Oxogestone_phenpropionate" title="Oxogestone phenpropionate">Oxogestone phenpropionate (xinogestone)</a></li> <li><a href="/wiki/Promegestone" title="Promegestone">Promegestone</a></li> <li><a href="/wiki/Segesterone" title="Segesterone">Segesterone</a></li> <li><a href="/wiki/Nestorone" class="mw-redirect" title="Nestorone">Segesterone acetate (nestorone)</a></li> <li><a href="/wiki/Trimegestone" title="Trimegestone">Trimegestone</a></li></ul> <ul><li><i>Testosterone derivatives:</i> Progestins: <a href="/wiki/6,6-Difluoronorethisterone" title="6,6-Difluoronorethisterone">6,6-Difluoronorethisterone</a></li> <li><a href="/wiki/6,6-Difluoronorethisterone_acetate" title="6,6-Difluoronorethisterone acetate">6,6-Difluoronorethisterone acetate</a></li> <li><a href="/wiki/17%CE%B1-Allyl-19-nortestosterone" title="17α-Allyl-19-nortestosterone">17α-Allyl-19-nortestosterone</a></li> <li><a href="/wiki/Allylestrenol" title="Allylestrenol">Allylestrenol</a></li> <li><a href="/wiki/Altrenogest" title="Altrenogest">Altrenogest</a></li> <li><a href="/wiki/Chloroethynylnorgestrel" title="Chloroethynylnorgestrel">Chloroethynylnorgestrel</a></li> <li><a href="/wiki/Cingestol" title="Cingestol">Cingestol</a></li> <li><a href="/wiki/Danazol" title="Danazol">Danazol</a></li> <li><a href="/wiki/Desogestrel" title="Desogestrel">Desogestrel</a></li> <li><a href="/wiki/Dienogest" title="Dienogest">Dienogest</a></li> <li><a href="/wiki/Ethinylandrostenediol" title="Ethinylandrostenediol">Ethinylandrostenediol</a> <ul><li><a href="/wiki/Ethandrostate" title="Ethandrostate">Ethandrostate</a></li></ul></li> <li><a href="/wiki/Ethisterone" title="Ethisterone">Ethisterone</a></li> <li><a href="/wiki/Ethynerone" title="Ethynerone">Ethynerone</a></li> <li><a href="/wiki/Etonogestrel" title="Etonogestrel">Etonogestrel</a></li> <li><a href="/wiki/Etynodiol" title="Etynodiol">Etynodiol</a></li> <li><a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">Etynodiol diacetate</a></li> <li><a href="/wiki/Gestodene" title="Gestodene">Gestodene</a></li> <li><a href="/wiki/Gestrinone" title="Gestrinone">Gestrinone</a></li> <li><a href="/wiki/Levonorgestrel" title="Levonorgestrel">Levonorgestrel</a></li> <li><a href="/wiki/Levonorgestrel_ester" class="mw-redirect" title="Levonorgestrel ester">Levonorgestrel esters</a> (e.g., <a href="/wiki/Levonorgestrel_butanoate" title="Levonorgestrel butanoate">levonorgestrel butanoate</a>)</li> <li><a href="/wiki/Lynestrenol" title="Lynestrenol">Lynestrenol</a></li> <li><a href="/wiki/Lynestrenol_phenylpropionate" title="Lynestrenol phenylpropionate">Lynestrenol phenylpropionate</a></li> <li><a href="/wiki/Metynodiol" title="Metynodiol">Metynodiol</a></li> <li><a href="/wiki/Metynodiol_diacetate" title="Metynodiol diacetate">Metynodiol diacetate</a></li> <li><a href="/wiki/Norelgestromin" title="Norelgestromin">Norelgestromin</a></li> <li><a href="/wiki/Norethisterone" title="Norethisterone">Norethisterone (norethindrone)</a></li> <li><a href="/wiki/Norethisterone_ester" class="mw-redirect" title="Norethisterone ester">Norethisterone esters</a> (e.g., <a href="/wiki/Norethisterone_acetate" title="Norethisterone acetate">norethisterone acetate</a>, <a href="/wiki/Norethisterone_enanthate" title="Norethisterone enanthate">norethisterone enanthate</a>)</li> <li><a href="/wiki/Noretynodrel" title="Noretynodrel">Noretynodrel</a></li> <li><a href="/wiki/Norgesterone" title="Norgesterone">Norgesterone</a></li> <li><a href="/wiki/Norgestimate" title="Norgestimate">Norgestimate</a></li> <li><a href="/wiki/Norgestrel" title="Norgestrel">Norgestrel</a></li> <li><a href="/wiki/Norgestrienone" title="Norgestrienone">Norgestrienone</a></li> <li><a href="/wiki/Norvinisterone" title="Norvinisterone">Norvinisterone</a></li> <li><a href="/wiki/Oxendolone" title="Oxendolone">Oxendolone</a></li> <li><a href="/wiki/Quingestanol" title="Quingestanol">Quingestanol</a></li> <li><a href="/wiki/Quingestanol_acetate" title="Quingestanol acetate">Quingestanol acetate</a></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li> <li><a href="/wiki/Tigestol" title="Tigestol">Tigestol</a></li> <li><a href="/wiki/Tosagestin" title="Tosagestin">Tosagestin</a>; Anabolic–androgenic steroids: <a href="/wiki/11%CE%B2-Methyl-19-nortestosterone" title="11β-Methyl-19-nortestosterone">11β-Methyl-19-nortestosterone</a></li> <li><a href="/wiki/11%CE%B2-Methyl-19-nortestosterone_dodecylcarbonate" title="11β-Methyl-19-nortestosterone dodecylcarbonate">11β-Methyl-19-nortestosterone dodecylcarbonate</a></li> <li><a href="/wiki/19-Nor-5-androstenediol" title="19-Nor-5-androstenediol">19-Nor-5-androstenediol</a></li> <li><a href="/wiki/19-Nor-5-androstenedione" title="19-Nor-5-androstenedione">19-Nor-5-androstenedione</a></li> <li><a href="/wiki/19-Nordehydroepiandrosterone" title="19-Nordehydroepiandrosterone">19-Nordehydroepiandrosterone</a></li> <li><a href="/wiki/Bolandiol" title="Bolandiol">Bolandiol</a></li> <li><a href="/wiki/Bolandiol_dipropionate" title="Bolandiol dipropionate">Bolandiol dipropionate</a></li> <li><a href="/wiki/Bolandione" title="Bolandione">Bolandione</a></li> <li><a href="/wiki/Dimethisterone" title="Dimethisterone">Dimethisterone</a></li> <li><a href="/wiki/Dienedione" title="Dienedione">Dienedione</a></li> <li><a href="/wiki/Dienolone" title="Dienolone">Dienolone</a></li> <li><a href="/wiki/Dimethandrolone" title="Dimethandrolone">Dimethandrolone</a></li> <li><a href="/wiki/Dimethandrolone_buciclate" title="Dimethandrolone buciclate">Dimethandrolone buciclate</a></li> <li><a href="/wiki/Dimethandrolone_dodecylcarbonate" title="Dimethandrolone dodecylcarbonate">Dimethandrolone dodecylcarbonate</a></li> <li><a href="/wiki/Dimethandrolone_undecanoate" title="Dimethandrolone undecanoate">Dimethandrolone undecanoate</a></li> <li><a href="/wiki/Dimethyldienolone" title="Dimethyldienolone">Dimethyldienolone</a></li> <li><a href="/wiki/Dimethyltrienolone" title="Dimethyltrienolone">Dimethyltrienolone</a></li> <li><a href="/wiki/Ethyldienolone" title="Ethyldienolone">Ethyldienolone</a></li> <li><a href="/wiki/Ethylestrenol" title="Ethylestrenol">Ethylestrenol (ethylnandrol)</a></li> <li><a href="/wiki/Methyldienolone" title="Methyldienolone">Methyldienolone</a></li> <li><a href="/wiki/Metribolone" title="Metribolone">Metribolone (R-1881)</a></li> <li><a href="/wiki/Methoxydienone" title="Methoxydienone">Methoxydienone (methoxygonadiene)</a></li> <li><a href="/wiki/Mibolerone" title="Mibolerone">Mibolerone</a></li> <li><a href="/wiki/Nandrolone" title="Nandrolone">Nandrolone</a></li> <li><a href="/wiki/Nandrolone_ester" class="mw-redirect" title="Nandrolone ester">Nandrolone esters</a> (e.g., <a href="/wiki/Nandrolone_decanoate" title="Nandrolone decanoate">nandrolone decanoate</a>, <a href="/wiki/Nandrolone_phenylpropionate" title="Nandrolone phenylpropionate">nandrolone phenylpropionate</a>)</li> <li><a href="/wiki/Norethandrolone" title="Norethandrolone">Norethandrolone</a></li> <li><a href="/wiki/Normethandrone" title="Normethandrone">Normethandrone (methylestrenolone, normethandrolone, normethisterone)</a></li> <li><a href="/wiki/RU-2309" title="RU-2309">RU-2309</a></li> <li><a href="/wiki/Tetrahydrogestrinone" title="Tetrahydrogestrinone">Tetrahydrogestrinone</a></li> <li><a href="/wiki/Trenbolone" title="Trenbolone">Trenbolone (trienolone)</a></li> <li><a href="/wiki/Trenbolone_ester" class="mw-redirect" title="Trenbolone ester">Trenbolone esters</a> (e.g., <a href="/wiki/Trenbolone_acetate" title="Trenbolone acetate">trenbolone acetate</a>, <a href="/wiki/Trenbolone_enanthate" title="Trenbolone enanthate">trenbolone enanthate</a>)</li> <li><a href="/wiki/Trendione" title="Trendione">Trendione</a></li> <li><a href="/wiki/Trestolone" title="Trestolone">Trestolone</a></li> <li><a href="/wiki/Trestolone_acetate" title="Trestolone acetate">Trestolone acetate</a></li></ul> <ul><li><i>Spirolactone derivatives:</i> <a href="/wiki/Canrenoic_acid" title="Canrenoic acid">Canrenoic acid</a></li> <li><a href="/wiki/Canrenone" title="Canrenone">Canrenone</a></li> <li><a href="/wiki/Drospirenone" title="Drospirenone">Drospirenone</a></li> <li><a href="/wiki/Mespirenone" title="Mespirenone">Mespirenone</a></li> <li><a href="/wiki/Potassium_canrenoate" title="Potassium canrenoate">Potassium canrenoate</a></li> <li><a href="/wiki/Prorenone" title="Prorenone">Prorenone</a></li> <li><a href="/wiki/SC-5233" title="SC-5233">SC-5233 (spirolactone)</a></li> <li><a href="/wiki/SC-8109" title="SC-8109">SC-8109</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/wiki/Spirorenone" title="Spirorenone">Spirorenone</a></li></ul> <ul><li><i>Nonsteroidal:</i> <a href="/wiki/3,8-Dihydrodiligustilide" title="3,8-Dihydrodiligustilide">3,8-Dihydrodiligustilide</a></li> <li><a href="/wiki/LG-2527" title="LG-2527">LG-2527</a></li> <li><a href="/w/index.php?title=LG-100128&action=edit&redlink=1" class="new" title="LG-100128 (page does not exist)">LG-100128</a></li> <li><a href="/wiki/Riligustilide" title="Riligustilide">Riligustilide</a></li> <li><a href="/w/index.php?title=RWJ-26819&action=edit&redlink=1" class="new" title="RWJ-26819 (page does not exist)">RWJ-26819</a></li> <li><a href="/w/index.php?title=RWJ-49853&action=edit&redlink=1" class="new" title="RWJ-49853 (page does not exist)">RWJ-49853</a></li> <li><a href="/w/index.php?title=RWJ-60130&action=edit&redlink=1" class="new" title="RWJ-60130 (page does not exist)">RWJ-60130</a></li> <li><a href="/wiki/Tanaproget" title="Tanaproget">Tanaproget</a></li> <li><a href="/wiki/ZM-182345" title="ZM-182345">ZM-182345</a></li></ul> <ul><li><i>Unknown:</i> <a href="/wiki/ORG-47241" title="ORG-47241">ORG-47241</a></li> <li><a href="/wiki/ORG-201745" title="ORG-201745">ORG-201745</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Mixed<br />(<a href="/wiki/Selective_progesterone_receptor_modulators" class="mw-redirect" title="Selective progesterone receptor modulators"><abbr title="Selective progesterone receptor modulators">SPRMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Selective progesterone receptor modulators</span>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Steroidal:</i> <a href="/wiki/Dihydroethisterone" class="mw-redirect" title="Dihydroethisterone">Dihydroethisterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydrolevonorgestrel" title="5α-Dihydrolevonorgestrel">5α-Dihydrolevonorgestrel</a></li> <li><a href="/wiki/5%CE%B1-Dihydronorethisterone" title="5α-Dihydronorethisterone">5α-Dihydronorethisterone</a></li> <li><a href="/wiki/Asoprisnil" title="Asoprisnil">Asoprisnil</a></li> <li><a href="/wiki/Asoprisnil_ecamate" title="Asoprisnil ecamate">Asoprisnil ecamate</a></li> <li><a href="/wiki/Guggulsterone" title="Guggulsterone">Guggulsterone</a></li> <li><a href="/w/index.php?title=J1042&action=edit&redlink=1" class="new" title="J1042 (page does not exist)">J1042</a></li> <li><a href="/w/index.php?title=LG-120838&action=edit&redlink=1" class="new" title="LG-120838 (page does not exist)">LG-120838</a></li> <li><a href="/wiki/Metapristone" title="Metapristone">Metapristone (RU-42633)</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone (RU-486)</a></li> <li><a href="/w/index.php?title=ORF-9371&action=edit&redlink=1" class="new" title="ORF-9371 (page does not exist)">ORF-9371</a></li> <li><a href="/wiki/ORF-9326" class="mw-redirect" title="ORF-9326">ORF-9326</a></li> <li><a href="/w/index.php?title=ORG-31710&action=edit&redlink=1" class="new" title="ORG-31710 (page does not exist)">ORG-31710</a></li> <li><a href="/w/index.php?title=ORG-33628&action=edit&redlink=1" class="new" title="ORG-33628 (page does not exist)">ORG-33628</a></li> <li><a href="/w/index.php?title=RMI-12936&action=edit&redlink=1" class="new" title="RMI-12936 (page does not exist)">RMI-12936</a></li> <li><a href="/wiki/Telapristone" title="Telapristone">Telapristone</a></li> <li><a href="/wiki/Ulipristal_acetate" title="Ulipristal acetate">Ulipristal acetate</a></li> <li><a href="/wiki/Vilaprisan" title="Vilaprisan">Vilaprisan</a></li> <li><a href="/w/index.php?title=ZK-137316&action=edit&redlink=1" class="new" title="ZK-137316 (page does not exist)">ZK-137316</a></li></ul> <ul><li><i>Nonsteroidal:</i> <a href="/wiki/Apigenin" title="Apigenin">Apigenin</a></li> <li><a href="/wiki/Kaempferol" title="Kaempferol">Kaempferol</a></li> <li><a href="/w/index.php?title=LG-120920&action=edit&redlink=1" class="new" title="LG-120920 (page does not exist)">LG-120920</a></li> <li><a href="/wiki/Naringenin" title="Naringenin">Naringenin</a></li> <li><a href="/w/index.php?title=PRA-910&action=edit&redlink=1" class="new" title="PRA-910 (page does not exist)">PRA-910</a></li> <li><a href="/wiki/Syringic_acid" title="Syringic acid">Syringic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Steroidal:</i> <a href="/wiki/Aglepristone" title="Aglepristone">Aglepristone</a></li> <li><a href="/wiki/Lilopristone" title="Lilopristone">Lilopristone</a></li> <li><a href="/wiki/Lonaprisan" title="Lonaprisan">Lonaprisan</a></li> <li><a href="/wiki/Onapristone" title="Onapristone">Onapristone</a></li> <li><a href="/w/index.php?title=ORG-31710&action=edit&redlink=1" class="new" title="ORG-31710 (page does not exist)">ORG-31710</a></li> <li><a href="/w/index.php?title=ORG-31806&action=edit&redlink=1" class="new" title="ORG-31806 (page does not exist)">ORG-31806</a></li> <li><a href="/w/index.php?title=ORG-33628&action=edit&redlink=1" class="new" title="ORG-33628 (page does not exist)">ORG-33628</a></li> <li><a href="/w/index.php?title=RTI_3021%E2%80%93022&action=edit&redlink=1" class="new" title="RTI 3021–022 (page does not exist)">RTI 3021–022</a></li> <li><a href="/wiki/Toripristone" title="Toripristone">Toripristone</a></li> <li><a href="/wiki/Zanoterone" title="Zanoterone">Zanoterone</a></li></ul> <ul><li><i>Nonsteroidal:</i> <a href="/wiki/Darolutamide" title="Darolutamide">Darolutamide</a></li> <li><a href="/w/index.php?title=LG-001447&action=edit&redlink=1" class="new" title="LG-001447 (page does not exist)">LG-001447</a></li> <li><a href="/w/index.php?title=LG-100127&action=edit&redlink=1" class="new" title="LG-100127 (page does not exist)">LG-100127</a></li> <li><a href="/w/index.php?title=LG-100128&action=edit&redlink=1" class="new" title="LG-100128 (page does not exist)">LG-100128</a></li> <li><a href="/w/index.php?title=LG-120830&action=edit&redlink=1" class="new" title="LG-120830 (page does not exist)">LG-120830</a></li> <li><a href="/w/index.php?title=LG-121046&action=edit&redlink=1" class="new" title="LG-121046 (page does not exist)">LG-121046</a></li> <li><a href="/wiki/Valproic_acid" class="mw-redirect" title="Valproic acid">Valproic acid</a></li> <li><a href="/w/index.php?title=ZM-150271&action=edit&redlink=1" class="new" title="ZM-150271 (page does not exist)">ZM-150271</a></li> <li><a href="/w/index.php?title=ZM-172406&action=edit&redlink=1" class="new" title="ZM-172406 (page does not exist)">ZM-172406</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Membrane_progesterone_receptor" title="Membrane progesterone receptor"><abbr title="Membrane progesterone receptor">mPR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Membrane progesterone receptor</span><br />(<a href="/wiki/Progestin_and_adipoQ_receptor" title="Progestin and adipoQ receptor"><abbr title="Progestin and adipoQ receptor">PAQR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Progestin and adipoQ receptor</span>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">5α-Dihydroprogesterone</a></li> <li><a href="/wiki/5%CE%B2-Dihydroprogesterone" title="5β-Dihydroprogesterone">5β-Dihydroprogesterone</a></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycortisone (21-hydroxyprogesterone)</a></li> <li><a href="/wiki/11-Deoxycortisol" title="11-Deoxycortisol">11-Deoxycortisol (17α,21-dihydroxyprogesterone)</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone</a></li> <li><a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Progestogens_and_antiprogestogens" title="Template:Progestogens and antiprogestogens">Progestogens and antiprogestogens</a></dd> <dd><a href="/wiki/Template:Androgen_receptor_modulators" title="Template:Androgen receptor modulators">Androgen receptor modulators</a></dd> <dd><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators">Estrogen receptor modulators</a></dd> <dd><a href="/wiki/List_of_steroidal_progestogens" class="mw-redirect" title="List of steroidal progestogens">List of progestogens</a></dd></dl> </div></td></tr></tbody></table></div></div></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"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"></div><div role="navigation" class="navbox authority-control" aria-label="Navbox" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Help:Authority_control" title="Help:Authority control">Authority control databases</a>: National <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q177911#identifiers" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"><ul><li><span class="uid"><a rel="nofollow" class="external text" href="https://d-nb.info/gnd/4057379-5">Germany</a></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="https://id.loc.gov/authorities/sh85128057">United States</a></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Stéroïdes"><a rel="nofollow" class="external text" href="https://catalogue.bnf.fr/ark:/12148/cb11933319f">France</a></span></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Stéroïdes"><a rel="nofollow" class="external text" href="https://data.bnf.fr/ark:/12148/cb11933319f">BnF data</a></span></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="https://id.ndl.go.jp/auth/ndlna/00571767">Japan</a></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="steroidy"><a rel="nofollow" class="external text" href="https://aleph.nkp.cz/F/?func=find-c&local_base=aut&ccl_term=ica=ph249410&CON_LNG=ENG">Czech Republic</a></span></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="http://olduli.nli.org.il/F/?func=find-b&local_base=NLX10&find_code=UID&request=987007536308705171">Israel</a></span></li></ul></div></td></tr></tbody></table></div></div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Steroid&oldid=1258098712">https://en.wikipedia.org/w/index.php?title=Steroid&oldid=1258098712</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" 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