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class="vector-toc-numb">2</span> <span>Side effects</span> </div> </a> <ul id="toc-Side_effects-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pharmacology" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Pharmacology"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Pharmacology</span> </div> </a> <ul id="toc-Pharmacology-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Chemistry" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Chemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Chemistry</span> </div> </a> <ul id="toc-Chemistry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> <span 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<li id="toc-Environmental_presence" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Environmental_presence"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Environmental presence</span> </div> </a> <ul id="toc-Environmental_presence-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc 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href="https://fa.wikipedia.org/wiki/%D9%85%D8%B3%D8%AA%D8%B1%D8%A7%D9%86%D9%88%D9%84" title="مسترانول – Persian" lang="fa" hreflang="fa" data-title="مسترانول" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Mestranol" title="Mestranol – Malay" lang="ms" hreflang="ms" data-title="Mestranol" 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-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Mestranol" title="Mestranol – Portuguese" lang="pt" hreflang="pt" data-title="Mestranol" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Mestranol" title="Mestranol – Serbian" lang="sr" hreflang="sr" data-title="Mestranol" 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/Mestranol" title="Mestranol – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Mestranol" 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-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Mestranol" title="Mestranol – Vietnamese" lang="vi" hreflang="vi" data-title="Mestranol" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link 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.infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Mestranol">Mestranol</span></caption><tbody><tr><td colspan="2" class="infobox-image"><span class="dark_mode_safe" typeof="mw:File"><a href="/wiki/File:Mestranol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7d/Mestranol.svg/225px-Mestranol.svg.png" decoding="async" width="225" height="151" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7d/Mestranol.svg/338px-Mestranol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7d/Mestranol.svg/450px-Mestranol.svg.png 2x" data-file-width="512" data-file-height="344" /></a></span></td></tr><tr><td colspan="2" class="infobox-image"><span class="dark_mode_safe" typeof="mw:File"><a href="/wiki/File:Mestranol_molecule_ball.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7e/Mestranol_molecule_ball.png/250px-Mestranol_molecule_ball.png" decoding="async" width="250" height="142" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7e/Mestranol_molecule_ball.png/375px-Mestranol_molecule_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7e/Mestranol_molecule_ball.png/500px-Mestranol_molecule_ball.png 2x" data-file-width="2560" data-file-height="1450" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Enovid, Norinyl, Ortho-Novum, others</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">Ethinylestradiol 3-methyl ether; EEME; EE3ME; CB-8027; L-33355; RS-1044; 17α-Ethynylestradiol 3-methyl ether; 17α-Ethynyl-3-methoxyestra-1,3,5(10)-trien-17β-ol; 3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17β-ol</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/American_Society_of_Health-System_Pharmacists" title="American Society of Health-System Pharmacists">AHFS</a>/<a href="/wiki/Drugs.com" title="Drugs.com">Drugs.com</a></th><td class="infobox-data"><span title="www.drugs.com"><a rel="nofollow" class="external text" href="https://www.drugs.com/international/mestranol.html">International Drug Names</a></span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/MedlinePlus" title="MedlinePlus">MedlinePlus</a></th><td class="infobox-data"><span title="medlineplus.gov"><a rel="nofollow" class="external text" href="https://medlineplus.gov/druginfo/meds/a601050.html">a601050</a></span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of<br />administration</a></th><td class="infobox-data"><a href="/wiki/Oral_administration" title="Oral administration">By mouth</a><sup id="cite_ref-MortonHall2012_1-0" class="reference"><a href="#cite_note-MortonHall2012-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_class" title="Drug class">Drug class</a></th><td class="infobox-data"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogen</a>; <a href="/wiki/Estrogen_ether" class="mw-redirect" title="Estrogen ether">Estrogen ether</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li>None</li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li>In general: ℞ (Prescription only)</li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Metabolite" title="Metabolite">Metabolites</a></th><td class="infobox-data"><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Biological_half-life" title="Biological half-life">Elimination <span class="nowrap">half-life</span></a></th><td class="infobox-data">Mestranol: 50 min<sup id="cite_ref-RunnebaumRabe2013_2-0" class="reference"><a href="#cite_note-RunnebaumRabe2013-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><br /><abbr title="Ethinylestradiol">EE</abbr>: 7–36 hours<sup id="cite_ref-HughesWaters2016_3-0" class="reference"><a href="#cite_note-HughesWaters2016-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid2256522_4-0" class="reference"><a href="#cite_note-pmid2256522-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid23375353_5-0" class="reference"><a href="#cite_note-pmid23375353-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Shellenberger1986_6-0" class="reference"><a href="#cite_note-Shellenberger1986-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">(8<i>R</i>,9<i>S</i>,13<i>S</i>,14<i>S</i>,17<i>R</i>)-17-ethynyl-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6<i>H</i>-cyclopenta[<i>a</i>]phenanthren-17-ol</div></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=72-33-3">72-33-3</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <span style="font-weight:normal"><abbr title="Compound ID">CID</abbr></span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/6291">6291</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Guide_to_Pharmacology" title="Guide to Pharmacology">IUPHAR/BPS</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=7087">7087</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB01357">DB01357</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.6054.html">6054</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/B2V233XGE7">B2V233XGE7</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/KEGG" title="KEGG">KEGG</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D00575">D00575</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6784">CHEBI:6784</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL1201151">ChEMBL1201151</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID0020814">DTXSID0020814</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q904308#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.707">100.000.707</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q904308#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data"><span title="Carbon">C</span><sub>21</sub><span title="Hydrogen">H</span><sub>26</sub><span title="Oxygen">O</span><sub>2</sub></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data"><span class="nowrap"><span data-sort-value="7002310437000000000♠"></span>310.437</span> g·mol<sup>−1</sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%28c1cc4c%28cc1%29%5BC%40H%5D3CC%5BC%40%5D2%28%5BC%40%40H%5D%28CC%5BC%40%5D2%28C%23C%29O%29%5BC%40%40H%5D3CC4%29C%29C">Interactive image</a></span></li></ul></div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">O(c1cc4c(cc1)[C@H]3CC[C@]2([C@@H](CC[C@]2(C#C)O)[C@@H]3CC4)C)C</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">InChI=1S/C21H26O2/c1-4-21(22)12-10-19-18-7-5-14-13-15(23-3)6-8-16(14)17(18)9-11-20(19,21)2/h1,6,8,13,17-19,22H,5,7,9-12H2,2-3H3/t17-,18-,19+,20+,21+/m1/s1<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:IMSSROKUHAOUJS-MJCUULBUSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-below"><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style><span class="nobold">  <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=462249106&page2=Mestranol">(verify)</a></span></span></td></tr></tbody></table> <p><b>Mestranol</b>, sold under the brand names <b>Enovid</b>, <b>Norinyl</b>, and <b>Ortho-Novum</b> among others, is an <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogen</a> medication which has been used in <a href="/wiki/Birth_control_pill" class="mw-redirect" title="Birth control pill">birth control pills</a>, <a href="/wiki/Menopausal_hormone_therapy" class="mw-redirect" title="Menopausal hormone therapy">menopausal hormone therapy</a>, and the treatment of <a href="/wiki/Menstrual_disorder" title="Menstrual disorder">menstrual disorders</a>.<sup id="cite_ref-MortonHall2012_1-1" class="reference"><a href="#cite_note-MortonHall2012-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Marks2010_7-0" class="reference"><a href="#cite_note-Marks2010-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Blum2013_8-0" class="reference"><a href="#cite_note-Blum2013-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Drugs.com_9-0" class="reference"><a href="#cite_note-Drugs.com-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> It is formulated in combination with a <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestin</a> and is not available alone.<sup id="cite_ref-Drugs.com_9-1" class="reference"><a href="#cite_note-Drugs.com-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> It is taken <a href="/wiki/Oral_administration" title="Oral administration">by mouth</a>.<sup id="cite_ref-MortonHall2012_1-2" class="reference"><a href="#cite_note-MortonHall2012-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Side_effect" title="Side effect">Side effects</a> of mestranol include <a href="/wiki/Nausea" title="Nausea">nausea</a>, <a href="/wiki/Breast_tension" title="Breast tension">breast tension</a>, <a href="/wiki/Edema" title="Edema">edema</a>, and <a href="/wiki/Breakthrough_bleeding" class="mw-redirect" title="Breakthrough bleeding">breakthrough bleeding</a> among others.<sup id="cite_ref-Wittlinger1980_10-0" class="reference"><a href="#cite_note-Wittlinger1980-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> It is an <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogen</a>, or an <a href="/wiki/Agonist" title="Agonist">agonist</a> of the <a href="/wiki/Estrogen_receptor" title="Estrogen receptor">estrogen receptors</a>, the <a href="/wiki/Biological_target" title="Biological target">biological target</a> of estrogens like <a href="/wiki/Estradiol" title="Estradiol">estradiol</a>.<sup id="cite_ref-Shoupe2007_11-0" class="reference"><a href="#cite_note-Shoupe2007-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Mestranol is a <a href="/wiki/Prodrug" title="Prodrug">prodrug</a> of <a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">ethinylestradiol</a> in the body.<sup id="cite_ref-Shoupe2007_11-1" class="reference"><a href="#cite_note-Shoupe2007-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>Mestranol was discovered in 1956 and was introduced for medical use in 1957.<sup id="cite_ref-Sneader2005_12-0" class="reference"><a href="#cite_note-Sneader2005-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-LentzLobo2012_13-0" class="reference"><a href="#cite_note-LentzLobo2012-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> It was the estrogen component in the first birth control pill.<sup id="cite_ref-Sneader2005_12-1" class="reference"><a href="#cite_note-Sneader2005-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-LentzLobo2012_13-1" class="reference"><a href="#cite_note-LentzLobo2012-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> In 1969, mestranol was replaced by ethinylestradiol in most birth control pills, although mestranol continues to be used in a few birth control pills even today.<sup id="cite_ref-Aronson2009_14-0" class="reference"><a href="#cite_note-Aronson2009-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Drugs.com_9-2" class="reference"><a href="#cite_note-Drugs.com-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Mestranol remains available only in a few countries, including the <a href="/wiki/United_States" title="United States">United States</a>, <a href="/wiki/United_Kingdom" title="United Kingdom">United Kingdom</a>, <a href="/wiki/Japan" title="Japan">Japan</a>, and <a href="/wiki/Chile" title="Chile">Chile</a>.<sup id="cite_ref-Drugs.com_9-3" class="reference"><a href="#cite_note-Drugs.com-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Medical_uses">Medical uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Mestranol&action=edit&section=1" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Mestranol was employed as the estrogen component in many of the first <a href="/wiki/Combined_oral_contraceptive_pill" title="Combined oral contraceptive pill">oral contraceptives</a>, such as <a href="/wiki/Mestranol/noretynodrel" title="Mestranol/noretynodrel">mestranol/noretynodrel</a> (brand name <i>Enovid</i>) and <a href="/wiki/Mestranol/norethisterone" title="Mestranol/norethisterone">mestranol/norethisterone</a> (brand names <i>Ortho-Novum</i>, <i>Norinyl</i>), and is still in use today.<sup id="cite_ref-Marks2010_7-1" class="reference"><a href="#cite_note-Marks2010-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Blum2013_8-1" class="reference"><a href="#cite_note-Blum2013-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Drugs.com_9-4" class="reference"><a href="#cite_note-Drugs.com-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> In addition to its use as an oral contraceptive, mestranol has been used as a component of <a href="/wiki/Menopausal_hormone_therapy" class="mw-redirect" title="Menopausal hormone therapy">menopausal hormone therapy</a> for the treatment of <a href="/wiki/Menopause" title="Menopause">menopausal</a> <a href="/wiki/Symptom" class="mw-redirect" title="Symptom">symptoms</a>.<sup id="cite_ref-MortonHall2012_1-3" class="reference"><a href="#cite_note-MortonHall2012-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Side_effects">Side effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Mestranol&action=edit&section=2" title="Edit section: Side effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Ethinylestradiol#Side_effects" title="Ethinylestradiol">Ethinylestradiol § Side effects</a>, and <a href="/wiki/Estrogen_(medication)#Side_effects" title="Estrogen (medication)">Estrogen (medication) § Side effects</a></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-Empty_section plainlinks metadata ambox mbox-small-left ambox-content" role="presentation"><tbody><tr><td class="mbox-image"><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></td><td class="mbox-text"><div class="mbox-text-span"><b>This section is empty.</b> You can help by <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Mestranol&action=edit&section=">adding to it</a>. <span class="date-container"><i>(<span class="date">December 2023</span>)</i></span></div></td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Mestranol&action=edit&section=3" title="Edit section: Pharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Ethinylestradiol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Ethinylestradiol.svg/225px-Ethinylestradiol.svg.png" decoding="async" width="225" height="155" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Ethinylestradiol.svg/338px-Ethinylestradiol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Ethinylestradiol.svg/450px-Ethinylestradiol.svg.png 2x" data-file-width="512" data-file-height="353" /></a><figcaption><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a> (EE), the <a href="/wiki/Active_metabolite" title="Active metabolite">active form</a> of mestranol.</figcaption></figure> <p>Mestranol is a biologically inactive <a href="/wiki/Prodrug" title="Prodrug">prodrug</a> of ethinylestradiol to which it is <a href="/wiki/Demethylation" title="Demethylation">demethylated</a> in the <a href="/wiki/Liver" title="Liver">liver</a> (via O-Dealkylation) with a conversion efficiency of 70% (50 μg of mestranol is <a href="/wiki/Pharmacokinetic" class="mw-redirect" title="Pharmacokinetic">pharmacokinetically</a> <a href="/wiki/Bioequivalent" class="mw-redirect" title="Bioequivalent">bioequivalent</a> to 35 μg of ethinylestradiol).<sup id="cite_ref-FaigleSchenkel1998_15-0" class="reference"><a href="#cite_note-FaigleSchenkel1998-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-FalconeHurd2007_16-0" class="reference"><a href="#cite_note-FalconeHurd2007-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Shoupe2007_11-2" class="reference"><a href="#cite_note-Shoupe2007-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> It has been found to possess 0.1 to 2.3% of the <a href="/wiki/Relative_binding_affinity" class="mw-redirect" title="Relative binding affinity">relative binding affinity</a> of <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a> (100%) for the <a href="/wiki/Estrogen_receptor" title="Estrogen receptor">estrogen receptor</a>, compared to 75 to 190% for <a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">ethinylestradiol</a>.<sup id="cite_ref-pmid10746941_17-0" class="reference"><a href="#cite_note-pmid10746941-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Ruenitz2010_18-0" class="reference"><a href="#cite_note-Ruenitz2010-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p><p>The <a href="/wiki/Elimination_half-life" class="mw-redirect" title="Elimination half-life">elimination half-life</a> of mestranol has been reported to be 50 minutes.<sup id="cite_ref-RunnebaumRabe2013_2-1" class="reference"><a href="#cite_note-RunnebaumRabe2013-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> The elimination half-life of the active form of mestranol, ethinylestradiol, is 7 to 36 hours.<sup id="cite_ref-HughesWaters2016_3-1" class="reference"><a href="#cite_note-HughesWaters2016-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid2256522_4-1" class="reference"><a href="#cite_note-pmid2256522-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid23375353_5-1" class="reference"><a href="#cite_note-pmid23375353-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Shellenberger1986_6-1" class="reference"><a href="#cite_note-Shellenberger1986-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>The effective <a href="/wiki/Ovulation" title="Ovulation">ovulation</a>-inhibiting dosage of mestranol has been studied in women.<sup id="cite_ref-pmid4568621_19-0" class="reference"><a href="#cite_note-pmid4568621-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Pincus2013_20-0" class="reference"><a href="#cite_note-Pincus2013-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Greenblatt1966a_21-0" class="reference"><a href="#cite_note-Greenblatt1966a-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> It has been reported to be about 98% effective at inhibiting ovulation at a dosage of 75 or 80 μg/day.<sup id="cite_ref-Elger1972_22-0" class="reference"><a href="#cite_note-Elger1972-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Greenblatt1966a_21-1" class="reference"><a href="#cite_note-Greenblatt1966a-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HerrRevesz1970a_23-0" class="reference"><a href="#cite_note-HerrRevesz1970a-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> In another study, the ovulation rate was 15.4% at 50 μg/day, 5.7% at 80 μg/day, and 1.1% at 100 μg/day.<sup id="cite_ref-pmid1146927_24-0" class="reference"><a href="#cite_note-pmid1146927-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable sortable mw-collapsible mw-collapsed" style="text-align:left; margin-left:auto; margin-right:auto; border:none;"> <caption class="nowrap"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist 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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:Affinities_and_estrogenic_potencies_of_estrogen_esters_and_ethers_at_the_estrogen_receptors" title="Template:Affinities and estrogenic potencies of estrogen esters and ethers at the estrogen receptors"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Affinities_and_estrogenic_potencies_of_estrogen_esters_and_ethers_at_the_estrogen_receptors" title="Template talk:Affinities and estrogenic potencies of estrogen esters and ethers at the estrogen receptors"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Affinities_and_estrogenic_potencies_of_estrogen_esters_and_ethers_at_the_estrogen_receptors" title="Special:EditPage/Template:Affinities and estrogenic potencies of estrogen esters and ethers at the estrogen receptors"><abbr title="Edit this template">e</abbr></a></li></ul></div> Affinities and estrogenic potencies of estrogen esters and ethers at the estrogen receptors </caption> <tbody><tr> <th rowspan="2"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogen</a> </th> <th rowspan="2" class="unsortable">Other names </th> <th><a href="/wiki/Relative_binding_affinity" class="mw-redirect" title="Relative binding affinity"><abbr title="Relative binding affinity">RBA</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 Relative binding affinity</span> (%)<sup>a</sup> </th> <th colspan="2"><a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)"><abbr title="Relative estrogenic potency">REP</abbr></a> (%)<sup>b</sup> </th></tr> <tr> <th><a href="/wiki/Estrogen_receptor" title="Estrogen receptor">ER</a> </th> <th><a href="/wiki/ER%CE%B1" class="mw-redirect" title="ERα">ERα</a> </th> <th><a href="/wiki/ER%CE%B2" class="mw-redirect" title="ERβ">ERβ</a> </th></tr> <tr> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a> </td> <td>E2 </td> <td>100 </td> <td>100 </td> <td>100 </td></tr> <tr> <td><a href="/wiki/Estradiol_3-sulfate" class="mw-redirect" title="Estradiol 3-sulfate">Estradiol 3-sulfate</a> </td> <td>E2S; E2-3S </td> <td>? </td> <td>0.02 </td> <td>0.04 </td></tr> <tr> <td><a href="/wiki/Estradiol_3-glucuronide" title="Estradiol 3-glucuronide">Estradiol 3-glucuronide</a> </td> <td>E2-3G </td> <td>? </td> <td>0.02 </td> <td>0.09 </td></tr> <tr> <td><a href="/wiki/Estradiol_17%CE%B2-glucuronide" class="mw-redirect" title="Estradiol 17β-glucuronide">Estradiol 17β-glucuronide</a> </td> <td>E2-17G </td> <td>? </td> <td>0.002 </td> <td>0.0002 </td></tr> <tr> <td><a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">Estradiol benzoate</a> </td> <td>EB; Estradiol 3-benzoate </td> <td>10 </td> <td>1.1 </td> <td>0.52 </td></tr> <tr> <td><a href="/wiki/Estradiol_17%CE%B2-acetate" title="Estradiol 17β-acetate">Estradiol 17β-acetate</a> </td> <td>E2-17A </td> <td>31–45 </td> <td>24 </td> <td>? </td></tr> <tr> <td><a href="/wiki/Estradiol_diacetate" title="Estradiol diacetate">Estradiol diacetate</a> </td> <td>EDA; Estradiol 3,17β-diacetate </td> <td>? </td> <td>0.79 </td> <td>? </td></tr> <tr> <td><a href="/wiki/Estradiol_17%CE%B2-propionate" class="mw-redirect" title="Estradiol 17β-propionate">Estradiol propionate</a> </td> <td>EP; Estradiol 17β-propionate </td> <td>19–26 </td> <td>2.6 </td> <td>? </td></tr> <tr> <td><a href="/wiki/Estradiol_valerate" title="Estradiol valerate">Estradiol valerate</a> </td> <td>EV; Estradiol 17β-valerate </td> <td>2–11 </td> <td>0.04–21 </td> <td>? </td></tr> <tr> <td><a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">Estradiol cypionate</a> </td> <td>EC; Estradiol 17β-cypionate </td> <td>?<sup>c</sup> </td> <td>4.0 </td> <td>? </td></tr> <tr> <td><a href="/wiki/Estradiol_palmitate" title="Estradiol palmitate">Estradiol palmitate</a> </td> <td>Estradiol 17β-palmitate </td> <td>0 </td> <td>? </td> <td>? </td></tr> <tr> <td><a href="/wiki/Estradiol_stearate" title="Estradiol stearate">Estradiol stearate</a> </td> <td>Estradiol 17β-stearate </td> <td>0 </td> <td>? </td> <td>? </td></tr> <tr> <td><a href="/wiki/Estrone_(medication)" title="Estrone (medication)">Estrone</a> </td> <td>E1; 17-Ketoestradiol </td> <td>11 </td> <td>5.3–38 </td> <td>14 </td></tr> <tr> <td><a href="/wiki/Estrone_sulfate" title="Estrone sulfate">Estrone sulfate</a> </td> <td>E1S; Estrone 3-sulfate </td> <td>2 </td> <td>0.004 </td> <td>0.002 </td></tr> <tr> <td><a href="/wiki/Estrone_glucuronide" title="Estrone glucuronide">Estrone glucuronide</a> </td> <td>E1G; Estrone 3-glucuronide </td> <td>? </td> <td><0.001 </td> <td>0.0006 </td></tr> <tr> <td><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a> </td> <td>EE; 17α-Ethynylestradiol </td> <td>100 </td> <td>17–150 </td> <td>129 </td></tr> <tr> <td>Mestranol </td> <td>EE 3-methyl ether </td> <td>1 </td> <td>1.3–8.2 </td> <td>0.16 </td></tr> <tr> <td><a href="/wiki/Quinestrol" title="Quinestrol">Quinestrol</a> </td> <td>EE 3-cyclopentyl ether </td> <td>? </td> <td>0.37 </td> <td>? </td></tr> <tr class="sortbottom"> <td colspan="7" style="width: 1px; background-color:#eaecf0; text-align: center;"><b>Footnotes:</b> <sup>a</sup> = <a href="/wiki/Relative_binding_affinity" class="mw-redirect" title="Relative binding affinity">Relative binding affinities</a> (RBAs) were determined via <i><a href="/wiki/In_vitro" title="In vitro">in-vitro</a></i> displacement of <a href="/wiki/Radiolabel" class="mw-redirect" title="Radiolabel">labeled</a> <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a> from <a href="/wiki/Estrogen_receptor" title="Estrogen receptor">estrogen receptors</a> (ERs) generally of <a href="/wiki/Rodent" title="Rodent">rodent</a> <a href="/wiki/Uterus" title="Uterus">uterine</a> <a href="/wiki/Cytosol" title="Cytosol">cytosol</a>. <a href="/wiki/Estrogen_ester" title="Estrogen ester">Estrogen esters</a> are variably <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolyzed</a> into estrogens in these systems (shorter ester chain length -> greater rate of hydrolysis) and the ER RBAs of the esters decrease strongly when hydrolysis is prevented. <sup>b</sup> = Relative estrogenic potencies (REPs) were calculated from <a href="/wiki/Half-maximal_effective_concentration" class="mw-redirect" title="Half-maximal effective concentration">half-maximal effective concentrations</a> (EC<sub>50</sub>) that were determined via <i>in-vitro</i> <a href="/wiki/%CE%92%E2%80%90galactosidase" class="mw-redirect" title="Β‐galactosidase">β‐galactosidase</a> (β-gal) and <a href="/wiki/Green_fluorescent_protein" title="Green fluorescent protein">green fluorescent protein</a> (GFP) <a href="/wiki/Biosynthesis" title="Biosynthesis">production</a> <a href="/wiki/Bioassay" title="Bioassay">assays</a> in <a href="/wiki/Yeast" title="Yeast">yeast</a> expressing human <a href="/wiki/ER%CE%B1" class="mw-redirect" title="ERα">ERα</a> and human <a href="/wiki/ER%CE%B2" class="mw-redirect" title="ERβ">ERβ</a>. Both <a href="/wiki/Mammal" title="Mammal">mammalian</a> <a href="/wiki/Cell_(biology)" title="Cell (biology)">cells</a> and yeast have the capacity to hydrolyze estrogen esters. <sup>c</sup> = The affinities of <a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">estradiol cypionate</a> for the ERs are similar to those of <a href="/wiki/Estradiol_valerate" title="Estradiol valerate">estradiol valerate</a> and <a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">estradiol benzoate</a> (<a href="/wiki/File:Inhibition_of_estradiol_binding_by_selected_estrogens,_antiestrogens,_and_estrogen_esters_to_human_aortic_tissue_in_vitro.png" title="File:Inhibition of estradiol binding by selected estrogens, antiestrogens, and estrogen esters to human aortic tissue in vitro.png">figure</a>). <b>Sources:</b> See template page. </td></tr></tbody></table> <table class="wikitable plainrowheaders floatright" style="font-size: small; margin: 1em auto;"> <caption class="nowrap" style="font-size: 105%"><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:Oral_potencies_of_estrogens" title="Template:Oral potencies of estrogens"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Oral_potencies_of_estrogens" title="Template talk:Oral potencies of estrogens"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Oral_potencies_of_estrogens" title="Special:EditPage/Template:Oral potencies of estrogens"><abbr title="Edit this template">e</abbr></a></li></ul></div> Potencies of oral estrogens<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>data sources 1<span class="cite-bracket">]</span></a></sup> </caption> <tbody><tr> <th scope="col" style="width=100px;" rowspan="2">Compound </th> <th scope="col" colspan="6">Dosage for specific uses (mg usually)<sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>a<span class="cite-bracket">]</span></a></sup> </th></tr> <tr> <th scope="col" style="width=100px;"><abbr title="Endometrial threshold dose">ETD</abbr><sup id="cite_ref-2-3_46-0" class="reference"><a href="#cite_note-2-3-46"><span class="cite-bracket">[</span>b<span class="cite-bracket">]</span></a></sup> </th> <th scope="col" style="width=100px;"><abbr title="Endometrial proliferation dose">EPD</abbr><sup id="cite_ref-2-3_46-1" class="reference"><a href="#cite_note-2-3-46"><span class="cite-bracket">[</span>b<span class="cite-bracket">]</span></a></sup> </th> <th scope="col" style="width=100px;"><abbr title="Menopausal substitution dose">MSD</abbr><sup id="cite_ref-2-3_46-2" class="reference"><a href="#cite_note-2-3-46"><span class="cite-bracket">[</span>b<span class="cite-bracket">]</span></a></sup> </th> <th scope="col" style="width=100px;"><abbr title="Menopausal substitution dose">MSD</abbr><sup id="cite_ref-daily_47-0" class="reference"><a href="#cite_note-daily-47"><span class="cite-bracket">[</span>c<span class="cite-bracket">]</span></a></sup> </th> <th scope="col" style="width=100px;"><abbr title="Ovulation-inhibiting dose">OID</abbr><sup id="cite_ref-daily_47-1" class="reference"><a href="#cite_note-daily-47"><span class="cite-bracket">[</span>c<span class="cite-bracket">]</span></a></sup> </th> <th scope="col" style="width=100px;"><abbr title="Testosterone suppression dose">TSD</abbr><sup id="cite_ref-daily_47-2" class="reference"><a href="#cite_note-daily-47"><span class="cite-bracket">[</span>c<span class="cite-bracket">]</span></a></sup> </th></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol (non-micronized)</a> </th> <td>30</td> <td>≥120–300</td> <td>120</td> <td>6</td> <td>-</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol (micronized)</a> </th> <td>6–12</td> <td>60–80</td> <td>14–42</td> <td>1–2</td> <td>>5</td> <td>>8 </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Estradiol_valerate" title="Estradiol valerate">Estradiol valerate</a> </th> <td>6–12</td> <td>60–80</td> <td>14–42</td> <td>1–2</td> <td>-</td> <td>>8 </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">Estradiol benzoate</a> </th> <td>-</td> <td>60–140</td> <td>-</td> <td>-</td> <td>-</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Estriol_(medication)" title="Estriol (medication)">Estriol</a> </th> <td>≥20</td> <td>120–150<sup id="cite_ref-div_48-0" class="reference"><a href="#cite_note-div-48"><span class="cite-bracket">[</span>d<span class="cite-bracket">]</span></a></sup></td> <td>28–126</td> <td>1–6</td> <td>>5</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Estriol_succinate" title="Estriol succinate">Estriol succinate</a> </th> <td>-</td> <td>140–150<sup id="cite_ref-div_48-1" class="reference"><a href="#cite_note-div-48"><span class="cite-bracket">[</span>d<span class="cite-bracket">]</span></a></sup></td> <td>28–126</td> <td>2–6</td> <td>-</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Estrone_sulfate_(medication)" title="Estrone sulfate (medication)">Estrone sulfate</a> </th> <td>12</td> <td>60</td> <td>42</td> <td>2</td> <td>-</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a> </th> <td>5–12</td> <td>60–80</td> <td>8.4–25</td> <td>0.625–1.25</td> <td>>3.75</td> <td>7.5 </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a> </th> <td>200 μg</td> <td>1–2</td> <td>280 μg</td> <td>20–40 μg</td> <td>100 μg</td> <td>100 μg </td></tr> <tr> <th scope="row" style="background: #f8f9fa;">Mestranol </th> <td>300 μg</td> <td>1.5–3.0</td> <td>300–600 μg</td> <td>25–30 μg</td> <td>>80 μg</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Quinestrol" title="Quinestrol">Quinestrol</a> </th> <td>300 μg</td> <td>2–4</td> <td>500 μg</td> <td>25–50 μg</td> <td>-</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Methylestradiol" title="Methylestradiol">Methylestradiol</a> </th> <td>-</td> <td>2</td> <td>-</td> <td>-</td> <td>-</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a> </th> <td>2.5</td> <td>20–30</td> <td>11</td> <td>0.5–2.0</td> <td>>5</td> <td>3 </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Diethylstilbestrol_dipropionate" title="Diethylstilbestrol dipropionate">DES dipropionate</a> </th> <td>-</td> <td>15–30</td> <td>-</td> <td>-</td> <td>-</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Dienestrol" title="Dienestrol">Dienestrol</a> </th> <td>5</td> <td>30–40</td> <td>42</td> <td>0.5–4.0</td> <td>-</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Dienestrol_diacetate" title="Dienestrol diacetate">Dienestrol diacetate</a> </th> <td>3–5</td> <td>30–60</td> <td>-</td> <td>-</td> <td>-</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Hexestrol" title="Hexestrol">Hexestrol</a> </th> <td>-</td> <td>70–110</td> <td>-</td> <td>-</td> <td>-</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Chlorotrianisene" title="Chlorotrianisene">Chlorotrianisene</a> </th> <td>-</td> <td>>100</td> <td>-</td> <td>-</td> <td>>48</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Methallenestril" title="Methallenestril">Methallenestril</a> </th> <td>-</td> <td>400</td> <td>-</td> <td>-</td> <td>-</td> <td>- </td></tr> <tr class="sortbottom"> <td colspan="8" style="width: 1px; background-color:#eaecf0; text-align: center;"><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;">Sources and footnotes:</div><div class="hidden-content mw-collapsible-content" style=""> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-44"><span class="mw-cite-backlink"><b><a href="#cite_ref-44">^</a></b></span> <span class="reference-text"><sup id="cite_ref-pmid2215269_25-0" class="reference"><a href="#cite_note-pmid2215269-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid559617_26-0" class="reference"><a href="#cite_note-pmid559617-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-WolfSchneider2013_27-0" class="reference"><a href="#cite_note-WolfSchneider2013-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-GöretzlehnerLauritzen2012_28-0" class="reference"><a href="#cite_note-GöretzlehnerLauritzen2012-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-KnörrBeller2013_29-0" class="reference"><a href="#cite_note-KnörrBeller2013-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HorskyPresl1981_30-0" class="reference"><a href="#cite_note-HorskyPresl1981-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> <sup id="cite_ref-Pschyrembel1968_31-0" class="reference"><a href="#cite_note-Pschyrembel1968-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid779393_32-0" class="reference"><a href="#cite_note-pmid779393-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Lauritzen1975_33-0" class="reference"><a href="#cite_note-Lauritzen1975-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Kopera1991_34-0" class="reference"><a href="#cite_note-Kopera1991-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> <sup id="cite_ref-pmid29603164_35-0" class="reference"><a href="#cite_note-pmid29603164-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid29756046_36-0" class="reference"><a href="#cite_note-pmid29756046-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Rydén1950_37-0" class="reference"><a href="#cite_note-Rydén1950-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid14902290_38-0" class="reference"><a href="#cite_note-pmid14902290-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Kottmeier1947_39-0" class="reference"><a href="#cite_note-Kottmeier1947-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-RietbrockStaib2013_40-0" class="reference"><a href="#cite_note-RietbrockStaib2013-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Greenblatt1966_41-0" class="reference"><a href="#cite_note-Greenblatt1966-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HerrRevesz1970_42-0" class="reference"><a href="#cite_note-HerrRevesz1970-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid13370006_43-0" class="reference"><a href="#cite_note-pmid13370006-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup></span> </li> </ol></div></div><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626"><div class="reflist reflist-lower-alpha"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-45"><span class="mw-cite-backlink"><b><a href="#cite_ref-45">^</a></b></span> <span class="reference-text">Dosages are given in milligrams unless otherwise noted.</span> </li> <li id="cite_note-2-3-46"><span class="mw-cite-backlink">^ <a href="#cite_ref-2-3_46-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-2-3_46-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-2-3_46-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text">Dosed every 2 to 3 weeks</span> </li> <li id="cite_note-daily-47"><span class="mw-cite-backlink">^ <a href="#cite_ref-daily_47-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-daily_47-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-daily_47-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text">Dosed daily</span> </li> <li id="cite_note-div-48"><span class="mw-cite-backlink">^ <a href="#cite_ref-div_48-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-div_48-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text">In divided doses, 3x/day; irregular and atypical proliferation.</span> </li> </ol></div></div></div></div> </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Mestranol&action=edit&section=4" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/List_of_estrogens" title="List of estrogens">List of estrogens</a> and <a href="/wiki/List_of_estrogen_esters#Ethers_of_steroidal_estrogens" title="List of estrogen esters">List of estrogen esters § Ethers of steroidal estrogens</a></div> <p>Mestranol, also known as ethinylestradiol 3-methyl ether (EEME) or as 17α-ethynyl-3-methoxyestra-1,3,5(10)-trien-17β-ol, is a <a href="/wiki/Synthetic_compound" class="mw-redirect" title="Synthetic compound">synthetic</a> <a href="/wiki/Estrane" title="Estrane">estrane</a> <a href="/wiki/Steroid" title="Steroid">steroid</a> and a <a href="/wiki/Chemical_derivative" class="mw-redirect" title="Chemical derivative">derivative</a> of <a href="/wiki/Estradiol" title="Estradiol">estradiol</a>.<sup id="cite_ref-Elks2014_49-0" class="reference"><a href="#cite_note-Elks2014-49"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-IndexNominum2000_50-0" class="reference"><a href="#cite_note-IndexNominum2000-50"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Labhart2012_51-0" class="reference"><a href="#cite_note-Labhart2012-51"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> It is specifically a derivative of <a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">ethinylestradiol</a> (17α-ethynylestradiol) with a <a href="/wiki/Methyl_group" title="Methyl group">methyl</a> <a href="/wiki/Ether" title="Ether">ether</a> at the C3 position.<sup id="cite_ref-Elks2014_49-1" class="reference"><a href="#cite_note-Elks2014-49"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-IndexNominum2000_50-1" class="reference"><a href="#cite_note-IndexNominum2000-50"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Mestranol&action=edit&section=5" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In April 1956, <a href="/wiki/Noretynodrel" title="Noretynodrel">noretynodrel</a> was investigated, in <a href="/wiki/Puerto_Rico" title="Puerto Rico">Puerto Rico</a>, in the first large-scale <a href="/wiki/Clinical_trial" title="Clinical trial">clinical trial</a> of a <a href="/wiki/Progestogen" title="Progestogen">progestogen</a> as an oral contraceptive.<sup id="cite_ref-Sneader2005_12-2" class="reference"><a href="#cite_note-Sneader2005-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-LentzLobo2012_13-2" class="reference"><a href="#cite_note-LentzLobo2012-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> The trial was conducted in Puerto Rico due to the high birth rate in the country and concerns of moral censure in the United States.<sup id="cite_ref-FilshieGuillebaud2013_52-0" class="reference"><a href="#cite_note-FilshieGuillebaud2013-52"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> It was discovered early into the study that the initial <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">chemical syntheses</a> of noretynodrel had been contaminated with small amounts (1–2%) of the 3-methyl ether of ethinylestradiol (noretynodrel having been synthesized from ethinylestradiol).<sup id="cite_ref-Sneader2005_12-3" class="reference"><a href="#cite_note-Sneader2005-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-LentzLobo2012_13-3" class="reference"><a href="#cite_note-LentzLobo2012-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> When this impurity was removed, higher rates of <a href="/wiki/Breakthrough_bleeding" class="mw-redirect" title="Breakthrough bleeding">breakthrough bleeding</a> occurred.<sup id="cite_ref-Sneader2005_12-4" class="reference"><a href="#cite_note-Sneader2005-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-LentzLobo2012_13-4" class="reference"><a href="#cite_note-LentzLobo2012-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> As a result, mestranol, that same year (1956),<sup id="cite_ref-pmid4884828_53-0" class="reference"><a href="#cite_note-pmid4884828-53"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> was developed and serendipitously identified as a very potent synthetic estrogen (and eventually as a prodrug of ethinylestradiol), given its name, and added back to the formulation.<sup id="cite_ref-Sneader2005_12-5" class="reference"><a href="#cite_note-Sneader2005-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-LentzLobo2012_13-5" class="reference"><a href="#cite_note-LentzLobo2012-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> This resulted in Enovid by <a href="/wiki/G.D._Searle,_LLC" title="G.D. Searle, LLC">G. D. Searle & Company</a>, the first oral contraceptive and a combination of 9.85 mg noretynodrel and 150 μg mestranol per pill.<sup id="cite_ref-Sneader2005_12-6" class="reference"><a href="#cite_note-Sneader2005-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-LentzLobo2012_13-6" class="reference"><a href="#cite_note-LentzLobo2012-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p><p>Around 1969, mestranol was replaced by ethinylestradiol in most combined oral contraceptives due to widespread panic about the recently uncovered increased risk of <a href="/wiki/Venous_thromboembolism" class="mw-redirect" title="Venous thromboembolism">venous thromboembolism</a> with estrogen-containing oral contraceptives.<sup id="cite_ref-Aronson2009_14-1" class="reference"><a href="#cite_note-Aronson2009-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> The rationale was that ethinylestradiol was approximately twice as potent by weight as mestranol and hence that the dose could be halved, which it was thought might result in a lower incidence of venous thromboembolism.<sup id="cite_ref-Aronson2009_14-2" class="reference"><a href="#cite_note-Aronson2009-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Whether this actually did result in a lower incidence of venous thromboembolism has never been assessed.<sup id="cite_ref-Aronson2009_14-3" class="reference"><a href="#cite_note-Aronson2009-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Mestranol&action=edit&section=6" title="Edit section: Society and culture"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Generic_names">Generic names</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Mestranol&action=edit&section=7" title="Edit section: Generic names"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><i>Mestranol</i> is the <a href="/wiki/Generic_term" class="mw-redirect" title="Generic term">generic name</a> of the drug and its <a href="/wiki/International_Nonproprietary_Name" class="mw-redirect" title="International Nonproprietary Name"><abbr title="International Nonproprietary Name">INN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip International Nonproprietary Name</span>, <a href="/wiki/United_States_Adopted_Name" title="United States Adopted Name"><abbr title="United States Adopted Name">USAN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip United States Adopted Name</span>, <a href="/wiki/United_States_Pharmacopeia" title="United States Pharmacopeia"><abbr title="United States Pharmacopeia">USP</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip United States Pharmacopeia</span>, <a href="/wiki/British_Approved_Name" title="British Approved Name"><abbr title="British Approved Name">BAN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip British Approved Name</span>, <a href="/wiki/D%C3%A9nomination_Commune_Fran%C3%A7aise" title="Dénomination Commune Française"><abbr title="Dénomination Commune Française">DCF</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Dénomination Commune Française</span>, and <a href="/wiki/Japanese_Accepted_Name" title="Japanese Accepted Name"><abbr title="Japanese Accepted Name">JAN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Japanese Accepted Name</span>, while <i>mestranolo</i> is its <a href="/wiki/Denominazione_Comune_Italiana" title="Denominazione Comune Italiana"><abbr title="Denominazione Comune Italiana">DCIT</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Denominazione Comune Italiana</span>.<sup id="cite_ref-Elks2014_49-2" class="reference"><a href="#cite_note-Elks2014-49"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-IndexNominum2000_50-2" class="reference"><a href="#cite_note-IndexNominum2000-50"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MortonHall2012_1-4" class="reference"><a href="#cite_note-MortonHall2012-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Drugs.com_9-5" class="reference"><a href="#cite_note-Drugs.com-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Brand_names">Brand names</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Mestranol&action=edit&section=8" title="Edit section: Brand names"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Mestranol has been marketed under a variety of brand names, mostly or exclusively in combination with progestins, including Devocin, Enavid, Enovid, Femigen, Mestranol, Norbiogest, Ortho-Novin, Ortho-Novum, Ovastol, and Tranel among others.<sup id="cite_ref-Marks2010_7-2" class="reference"><a href="#cite_note-Marks2010-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Elks2014_49-3" class="reference"><a href="#cite_note-Elks2014-49"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Publishing2013_54-0" class="reference"><a href="#cite_note-Publishing2013-54"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-IndexNominum2000_50-3" class="reference"><a href="#cite_note-IndexNominum2000-50"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> Today, it continues to be sold in combination with progestins under brand names including Lutedion, Necon, Norinyl, Ortho-Novum, and Sophia.<sup id="cite_ref-Drugs.com_9-6" class="reference"><a href="#cite_note-Drugs.com-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Availability">Availability</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Mestranol&action=edit&section=9" title="Edit section: Availability"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Mestranol remains available only in the <a href="/wiki/United_States" title="United States">United States</a>, the <a href="/wiki/United_Kingdom" title="United Kingdom">United Kingdom</a>, <a href="/wiki/Japan" title="Japan">Japan</a>, and <a href="/wiki/Chile" title="Chile">Chile</a>.<sup id="cite_ref-Drugs.com_9-7" class="reference"><a href="#cite_note-Drugs.com-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> It is only marketed in combination with <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestins</a>, such as <a href="/wiki/Norethisterone" title="Norethisterone">norethisterone</a>.<sup id="cite_ref-Drugs.com_9-8" class="reference"><a href="#cite_note-Drugs.com-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Mestranol&action=edit&section=10" title="Edit section: Research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Mestranol has been studied as a <a href="/wiki/Male_contraceptive" title="Male contraceptive">male contraceptive</a> and was found to be highly effective.<sup id="cite_ref-pmid6771777_55-0" class="reference"><a href="#cite_note-pmid6771777-55"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid776453_56-0" class="reference"><a href="#cite_note-pmid776453-56"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Oettel1999_57-0" class="reference"><a href="#cite_note-Oettel1999-57"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid14400846_58-0" class="reference"><a href="#cite_note-pmid14400846-58"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> At a dosage of 0.45 mg/day, it suppressed <a href="/wiki/Gonadotropin" title="Gonadotropin">gonadotropin</a> levels, reduced <a href="/wiki/Sperm_count" class="mw-redirect" title="Sperm count">sperm count</a> to zero within 4 to 6 weeks, and decreased <a href="/wiki/Libido" title="Libido">libido</a>, <a href="/wiki/Erectile_function" class="mw-redirect" title="Erectile function">erectile function</a>, and <a href="/wiki/Testicular_size" class="mw-redirect" title="Testicular size">testicular size</a>.<sup id="cite_ref-pmid6771777_55-1" class="reference"><a href="#cite_note-pmid6771777-55"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid776453_56-1" class="reference"><a href="#cite_note-pmid776453-56"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid14400846_58-1" class="reference"><a href="#cite_note-pmid14400846-58"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Oettel1999_57-1" class="reference"><a href="#cite_note-Oettel1999-57"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Gynecomastia" title="Gynecomastia">Gynecomastia</a> occurred in all of the men.<sup id="cite_ref-pmid6771777_55-2" class="reference"><a href="#cite_note-pmid6771777-55"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid776453_56-2" class="reference"><a href="#cite_note-pmid776453-56"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid14400846_58-2" class="reference"><a href="#cite_note-pmid14400846-58"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Oettel1999_57-2" class="reference"><a href="#cite_note-Oettel1999-57"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> These findings contributed to the conclusion that estrogens would be unacceptable as contraceptives for men.<sup id="cite_ref-pmid776453_56-3" class="reference"><a href="#cite_note-pmid776453-56"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Environmental_presence">Environmental presence</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Mestranol&action=edit&section=11" title="Edit section: Environmental presence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In 2021, mestranol was one of the 12 compounds identified in sludge samples taken from 12 <a href="/wiki/Wastewater_treatment" title="Wastewater treatment">wastewater treatment</a> plants in <a href="/wiki/California" title="California">California</a> that were collectively associated with <a href="/wiki/Estrogenic" class="mw-redirect" title="Estrogenic">estrogenic</a> activity in <a href="/wiki/In_vitro" title="In vitro">in vitro</a>. <sup id="cite_ref-Black2021_59-0" class="reference"><a href="#cite_note-Black2021-59"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Mestranol&action=edit&section=12" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626"><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-MortonHall2012-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-MortonHall2012_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-MortonHall2012_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-MortonHall2012_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-MortonHall2012_1-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-MortonHall2012_1-4"><sup><i><b>e</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="CITEREFMortonHall2012" class="citation book cs1">Morton IK, Hall JM (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA177"><i>Concise Dictionary of Pharmacological Agents: Properties and Synonyms</i></a>. Springer Science & Business Media. pp. 177–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-94-011-4439-1" title="Special:BookSources/978-94-011-4439-1"><bdi>978-94-011-4439-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Concise+Dictionary+of+Pharmacological+Agents%3A+Properties+and+Synonyms&rft.pages=177-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-94-011-4439-1&rft.aulast=Morton&rft.aufirst=IK&rft.au=Hall%2C+JM&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DtsjrCAAAQBAJ%26pg%3DPA177&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-RunnebaumRabe2013-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-RunnebaumRabe2013_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-RunnebaumRabe2013_2-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRunnebaumRabe2013" class="citation book cs1">Runnebaum B, Rabe T (17 April 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=mBF9BwAAQBAJ&pg=PA88"><i>Gynäkologische Endokrinologie und Fortpflanzungsmedizin: Band 1: Gynäkologische Endokrinologie</i></a>. Springer-Verlag. pp. 88–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-662-07635-4" title="Special:BookSources/978-3-662-07635-4"><bdi>978-3-662-07635-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Gyn%C3%A4kologische+Endokrinologie+und+Fortpflanzungsmedizin%3A+Band+1%3A+Gyn%C3%A4kologische+Endokrinologie&rft.pages=88-&rft.pub=Springer-Verlag&rft.date=2013-04-17&rft.isbn=978-3-662-07635-4&rft.aulast=Runnebaum&rft.aufirst=B&rft.au=Rabe%2C+T&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DmBF9BwAAQBAJ%26pg%3DPA88&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-HughesWaters2016-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-HughesWaters2016_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-HughesWaters2016_3-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHughesWaters2016" class="citation book cs1">Hughes CL, Waters MD (23 March 2016). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=5qPWCwAAQBAJ&pg=PA73"><i>Translational Toxicology: Defining a New Therapeutic Discipline</i></a>. Humana Press. pp. 73–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-319-27449-2" title="Special:BookSources/978-3-319-27449-2"><bdi>978-3-319-27449-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Translational+Toxicology%3A+Defining+a+New+Therapeutic+Discipline&rft.pages=73-&rft.pub=Humana+Press&rft.date=2016-03-23&rft.isbn=978-3-319-27449-2&rft.aulast=Hughes&rft.aufirst=CL&rft.au=Waters%2C+MD&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D5qPWCwAAQBAJ%26pg%3DPA73&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-pmid2256522-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid2256522_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid2256522_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 id="CITEREFGoldzieherBrody1990" class="citation journal cs1">Goldzieher JW, Brody SA (December 1990). "Pharmacokinetics of ethinyl estradiol and mestranol". <i>American Journal of Obstetrics and Gynecology</i>. <b>163</b> (6 Pt 2): <span class="nowrap">2114–</span>2119. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0002-9378%2890%2990550-Q">10.1016/0002-9378(90)90550-Q</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/2256522">2256522</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=American+Journal+of+Obstetrics+and+Gynecology&rft.atitle=Pharmacokinetics+of+ethinyl+estradiol+and+mestranol&rft.volume=163&rft.issue=6+Pt+2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E2114-%3C%2Fspan%3E2119&rft.date=1990-12&rft_id=info%3Adoi%2F10.1016%2F0002-9378%2890%2990550-Q&rft_id=info%3Apmid%2F2256522&rft.aulast=Goldzieher&rft.aufirst=JW&rft.au=Brody%2C+SA&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-pmid23375353-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid23375353_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid23375353_5-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFStanczykArcherBhavnani2013" class="citation journal cs1">Stanczyk FZ, Archer DF, Bhavnani BR (June 2013). "Ethinyl estradiol and 17β-estradiol in combined oral contraceptives: pharmacokinetics, pharmacodynamics and risk assessment". <i>Contraception</i>. <b>87</b> (6): <span class="nowrap">706–</span>727. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.contraception.2012.12.011">10.1016/j.contraception.2012.12.011</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/23375353">23375353</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Contraception&rft.atitle=Ethinyl+estradiol+and+17%CE%B2-estradiol+in+combined+oral+contraceptives%3A+pharmacokinetics%2C+pharmacodynamics+and+risk+assessment&rft.volume=87&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E706-%3C%2Fspan%3E727&rft.date=2013-06&rft_id=info%3Adoi%2F10.1016%2Fj.contraception.2012.12.011&rft_id=info%3Apmid%2F23375353&rft.aulast=Stanczyk&rft.aufirst=FZ&rft.au=Archer%2C+DF&rft.au=Bhavnani%2C+BR&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-Shellenberger1986-6"><span class="mw-cite-backlink">^ <a href="#cite_ref-Shellenberger1986_6-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Shellenberger1986_6-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFShellenberger1986" class="citation book cs1">Shellenberger TE (1986). "Pharmacology of estrogens". <i>The Climacteric in Perspective</i>. Springer. pp. <span class="nowrap">393–</span>410. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-94-009-4145-8_36">10.1007/978-94-009-4145-8_36</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-94-010-8339-3" title="Special:BookSources/978-94-010-8339-3"><bdi>978-94-010-8339-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Pharmacology+of+estrogens&rft.btitle=The+Climacteric+in+Perspective&rft.pages=%3Cspan+class%3D%22nowrap%22%3E393-%3C%2Fspan%3E410&rft.pub=Springer&rft.date=1986&rft_id=info%3Adoi%2F10.1007%2F978-94-009-4145-8_36&rft.isbn=978-94-010-8339-3&rft.aulast=Shellenberger&rft.aufirst=TE&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-Marks2010-7"><span class="mw-cite-backlink">^ <a href="#cite_ref-Marks2010_7-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Marks2010_7-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Marks2010_7-2"><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="CITEREFMarks2010" class="citation book cs1">Marks L (2010). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=_i-s4biQs7MC&pg=PA75"><i>Sexual Chemistry: A History of the Contraceptive Pill</i></a>. Yale University Press. pp. 75–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-300-16791-7" title="Special:BookSources/978-0-300-16791-7"><bdi>978-0-300-16791-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Sexual+Chemistry%3A+A+History+of+the+Contraceptive+Pill&rft.pages=75-&rft.pub=Yale+University+Press&rft.date=2010&rft.isbn=978-0-300-16791-7&rft.aulast=Marks&rft.aufirst=L&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D_i-s4biQs7MC%26pg%3DPA75&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-Blum2013-8"><span class="mw-cite-backlink">^ <a href="#cite_ref-Blum2013_8-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Blum2013_8-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBlum2013" class="citation book cs1">Blum RW (22 October 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=36PpAgAAQBAJ&pg=PA216"><i>Adolescent Health Care: Clinical Issues</i></a>. Elsevier Science. pp. 216–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4832-7738-7" title="Special:BookSources/978-1-4832-7738-7"><bdi>978-1-4832-7738-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Adolescent+Health+Care%3A+Clinical+Issues&rft.pages=216-&rft.pub=Elsevier+Science&rft.date=2013-10-22&rft.isbn=978-1-4832-7738-7&rft.aulast=Blum&rft.aufirst=RW&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D36PpAgAAQBAJ%26pg%3DPA216&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-Drugs.com-9"><span class="mw-cite-backlink">^ <a href="#cite_ref-Drugs.com_9-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Drugs.com_9-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Drugs.com_9-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Drugs.com_9-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Drugs.com_9-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-Drugs.com_9-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-Drugs.com_9-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-Drugs.com_9-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-Drugs.com_9-8"><sup><i><b>i</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/20171201042946/https://www.drugs.com/international/mestranol.html">"Mestranol and norethindrone Uses, Side Effects & Warnings"</a>. Archived from <a rel="nofollow" class="external text" href="https://www.drugs.com/international/mestranol.html">the original</a> on 2017-12-01<span class="reference-accessdate">. Retrieved <span class="nowrap">2017-11-24</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Mestranol+and+norethindrone+Uses%2C+Side+Effects+%26+Warnings&rft_id=https%3A%2F%2Fwww.drugs.com%2Finternational%2Fmestranol.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-Wittlinger1980-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-Wittlinger1980_10-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWittlinger1980" class="citation book cs1">Wittlinger H (1980). "Clinical Effects of Estrogens". <i>Functional Morphologic Changes in Female Sex Organs Induced by Exogenous Hormones</i>. Springer. pp. <span class="nowrap">67–</span>71. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-3-642-67568-3_10">10.1007/978-3-642-67568-3_10</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-67570-6" title="Special:BookSources/978-3-642-67570-6"><bdi>978-3-642-67570-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Clinical+Effects+of+Estrogens&rft.btitle=Functional+Morphologic+Changes+in+Female+Sex+Organs+Induced+by+Exogenous+Hormones&rft.pages=%3Cspan+class%3D%22nowrap%22%3E67-%3C%2Fspan%3E71&rft.pub=Springer&rft.date=1980&rft_id=info%3Adoi%2F10.1007%2F978-3-642-67568-3_10&rft.isbn=978-3-642-67570-6&rft.aulast=Wittlinger&rft.aufirst=H&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-Shoupe2007-11"><span class="mw-cite-backlink">^ <a href="#cite_ref-Shoupe2007_11-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Shoupe2007_11-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Shoupe2007_11-2"><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="CITEREFShoupe2007" class="citation book cs1">Shoupe D (7 November 2007). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=sczb0Tk_2IwC&pg=PA23"><i>The Handbook of Contraception: A Guide for Practical Management</i></a>. Springer Science & Business Media. pp. 23–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-59745-150-5" title="Special:BookSources/978-1-59745-150-5"><bdi>978-1-59745-150-5</bdi></a>. <q>EE is about 1.7 times as potent as the same weight of mestranol.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Handbook+of+Contraception%3A+A+Guide+for+Practical+Management&rft.pages=23-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2007-11-07&rft.isbn=978-1-59745-150-5&rft.aulast=Shoupe&rft.aufirst=D&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dsczb0Tk_2IwC%26pg%3DPA23&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-Sneader2005-12"><span class="mw-cite-backlink">^ <a href="#cite_ref-Sneader2005_12-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Sneader2005_12-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Sneader2005_12-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Sneader2005_12-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Sneader2005_12-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-Sneader2005_12-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-Sneader2005_12-6"><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="CITEREFSneader2005" class="citation book cs1">Sneader W (23 June 2005). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=Cb6BOkj9fK4C&pg=PA202"><i>Drug Discovery: A History</i></a>. John Wiley & Sons. pp. 202–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-89979-2" title="Special:BookSources/978-0-471-89979-2"><bdi>978-0-471-89979-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Drug+Discovery%3A+A+History&rft.pages=202-&rft.pub=John+Wiley+%26+Sons&rft.date=2005-06-23&rft.isbn=978-0-471-89979-2&rft.aulast=Sneader&rft.aufirst=W&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DCb6BOkj9fK4C%26pg%3DPA202&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-LentzLobo2012-13"><span class="mw-cite-backlink">^ <a href="#cite_ref-LentzLobo2012_13-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-LentzLobo2012_13-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-LentzLobo2012_13-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-LentzLobo2012_13-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-LentzLobo2012_13-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-LentzLobo2012_13-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-LentzLobo2012_13-6"><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="CITEREFLentzLoboGershensonKatz2012" class="citation book cs1">Lentz GM, Lobo RA, Gershenson DM, Katz VL (2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=OmpULog7A_QC&pg=PA224"><i>Comprehensive Gynecology</i></a>. Elsevier Health Sciences. pp. 224–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-323-06986-1" title="Special:BookSources/978-0-323-06986-1"><bdi>978-0-323-06986-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Comprehensive+Gynecology&rft.pages=224-&rft.pub=Elsevier+Health+Sciences&rft.date=2012&rft.isbn=978-0-323-06986-1&rft.aulast=Lentz&rft.aufirst=GM&rft.au=Lobo%2C+RA&rft.au=Gershenson%2C+DM&rft.au=Katz%2C+VL&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DOmpULog7A_QC%26pg%3DPA224&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-Aronson2009-14"><span class="mw-cite-backlink">^ <a href="#cite_ref-Aronson2009_14-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Aronson2009_14-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Aronson2009_14-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Aronson2009_14-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAronson2009" class="citation book cs1">Aronson JK (21 February 2009). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=BWMeSwVwfTkC&pg=PA224"><i>Meyler's Side Effects of Endocrine and Metabolic Drugs</i></a>. Elsevier. pp. 224–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-08-093292-7" title="Special:BookSources/978-0-08-093292-7"><bdi>978-0-08-093292-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Meyler%27s+Side+Effects+of+Endocrine+and+Metabolic+Drugs&rft.pages=224-&rft.pub=Elsevier&rft.date=2009-02-21&rft.isbn=978-0-08-093292-7&rft.aulast=Aronson&rft.aufirst=JK&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DBWMeSwVwfTkC%26pg%3DPA224&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-FaigleSchenkel1998-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-FaigleSchenkel1998_15-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFaigleSchenkel1998" class="citation book cs1">Faigle JW, Schenkel L (1998). "Pharmacokinetics of estrogens and progestogens". In Fraser IS, Whitehead MI, Jansen R, Lobo RA (eds.). <i>Estrogens and Progestogens in Clinical Practice</i>. London: Churchill Livingstone. pp. <span class="nowrap">273–</span>294. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-443-04706-5" title="Special:BookSources/0-443-04706-5"><bdi>0-443-04706-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Pharmacokinetics+of+estrogens+and+progestogens&rft.btitle=Estrogens+and+Progestogens+in+Clinical+Practice&rft.place=London&rft.pages=%3Cspan+class%3D%22nowrap%22%3E273-%3C%2Fspan%3E294&rft.pub=Churchill+Livingstone&rft.date=1998&rft.isbn=0-443-04706-5&rft.aulast=Faigle&rft.aufirst=JW&rft.au=Schenkel%2C+L&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-FalconeHurd2007-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-FalconeHurd2007_16-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFalconeHurd2007" class="citation book cs1">Falcone T, Hurd WW (2007). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=fOPtaEIKvcIC&pg=PA388"><i>Clinical Reproductive Medicine and Surgery</i></a>. Elsevier Health Sciences. pp. 388–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-323-03309-1" title="Special:BookSources/978-0-323-03309-1"><bdi>978-0-323-03309-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Clinical+Reproductive+Medicine+and+Surgery&rft.pages=388-&rft.pub=Elsevier+Health+Sciences&rft.date=2007&rft.isbn=978-0-323-03309-1&rft.aulast=Falcone&rft.aufirst=T&rft.au=Hurd%2C+WW&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DfOPtaEIKvcIC%26pg%3DPA388&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-pmid10746941-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid10746941_17-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBlairFangBranhamHass2000" class="citation journal cs1">Blair RM, Fang H, Branham WS, Hass BS, Dial SL, Moland CL, et al. (March 2000). <a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Ftoxsci%2F54.1.138">"The estrogen receptor relative binding affinities of 188 natural and xenochemicals: structural diversity of ligands"</a>. <i>Toxicological Sciences</i>. <b>54</b> (1): <span class="nowrap">138–</span>153. <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/10.1093%2Ftoxsci%2F54.1.138">10.1093/toxsci/54.1.138</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/10746941">10746941</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Toxicological+Sciences&rft.atitle=The+estrogen+receptor+relative+binding+affinities+of+188+natural+and+xenochemicals%3A+structural+diversity+of+ligands&rft.volume=54&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E138-%3C%2Fspan%3E153&rft.date=2000-03&rft_id=info%3Adoi%2F10.1093%2Ftoxsci%2F54.1.138&rft_id=info%3Apmid%2F10746941&rft.aulast=Blair&rft.aufirst=RM&rft.au=Fang%2C+H&rft.au=Branham%2C+WS&rft.au=Hass%2C+BS&rft.au=Dial%2C+SL&rft.au=Moland%2C+CL&rft.au=Tong%2C+W&rft.au=Shi%2C+L&rft.au=Perkins%2C+R&rft.au=Sheehan%2C+DM&rft_id=https%3A%2F%2Fdoi.org%2F10.1093%252Ftoxsci%252F54.1.138&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-Ruenitz2010-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-Ruenitz2010_18-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRuenitz2010" class="citation book cs1">Ruenitz PC (2010). "Female Sex Hormones, Contraceptives, And Fertility Drugs". <i>Burger's Medicinal Chemistry and Drug Discovery</i>. Wiley. pp. <span class="nowrap">219–</span>264. <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%2F0471266949.bmc054">10.1002/0471266949.bmc054</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-26694-5" title="Special:BookSources/978-0-471-26694-5"><bdi>978-0-471-26694-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Female+Sex+Hormones%2C+Contraceptives%2C+And+Fertility+Drugs&rft.btitle=Burger%27s+Medicinal+Chemistry+and+Drug+Discovery&rft.pages=%3Cspan+class%3D%22nowrap%22%3E219-%3C%2Fspan%3E264&rft.pub=Wiley&rft.date=2010&rft_id=info%3Adoi%2F10.1002%2F0471266949.bmc054&rft.isbn=978-0-471-26694-5&rft.aulast=Ruenitz&rft.aufirst=PC&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-pmid4568621-19"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid4568621_19-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBingelBenoit1973" class="citation journal cs1">Bingel AS, Benoit PS (February 1973). "Oral contraceptives: therapeutics versus adverse reactions, with an outlook for the future I". <i>Journal of Pharmaceutical Sciences</i>. <b>62</b> (2): <span class="nowrap">179–</span>200. <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%2Fjps.2600620202">10.1002/jps.2600620202</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/4568621">4568621</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+Pharmaceutical+Sciences&rft.atitle=Oral+contraceptives%3A+therapeutics+versus+adverse+reactions%2C+with+an+outlook+for+the+future+I&rft.volume=62&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E179-%3C%2Fspan%3E200&rft.date=1973-02&rft_id=info%3Adoi%2F10.1002%2Fjps.2600620202&rft_id=info%3Apmid%2F4568621&rft.aulast=Bingel&rft.aufirst=AS&rft.au=Benoit%2C+PS&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-Pincus2013-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-Pincus2013_20-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPincus2013" class="citation book cs1">Pincus G (3 September 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=ehQlBQAAQBAJ&pg=PA222"><i>The Control of Fertility</i></a>. Elsevier. pp. 222–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4832-7088-3" title="Special:BookSources/978-1-4832-7088-3"><bdi>978-1-4832-7088-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Control+of+Fertility&rft.pages=222-&rft.pub=Elsevier&rft.date=2013-09-03&rft.isbn=978-1-4832-7088-3&rft.aulast=Pincus&rft.aufirst=G&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DehQlBQAAQBAJ%26pg%3DPA222&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-Greenblatt1966a-21"><span class="mw-cite-backlink">^ <a href="#cite_ref-Greenblatt1966a_21-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Greenblatt1966a_21-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMartinez-ManautouRudel1966" class="citation book cs1">Martinez-Manautou J, Rudel HW (1966). "Antiovulatory Activity of Several Synthetic and Natural Estrogens". In Greenblatt BR (ed.). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=le1qAAAAMAAJ"><i>Ovulation: Stimulation, Suppression, and Detection</i></a>. Lippincott. pp. <span class="nowrap">243–</span>253. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-397-59010-0" title="Special:BookSources/978-0-397-59010-0"><bdi>978-0-397-59010-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Antiovulatory+Activity+of+Several+Synthetic+and+Natural+Estrogens&rft.btitle=Ovulation%3A+Stimulation%2C+Suppression%2C+and+Detection&rft.pages=%3Cspan+class%3D%22nowrap%22%3E243-%3C%2Fspan%3E253&rft.pub=Lippincott&rft.date=1966&rft.isbn=978-0-397-59010-0&rft.aulast=Martinez-Manautou&rft.aufirst=J&rft.au=Rudel%2C+HW&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dle1qAAAAMAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-Elger1972-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-Elger1972_22-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFElger1972" class="citation book cs1">Elger W (1972). "Physiology and pharmacology of female reproduction under the aspect of fertility control". <i>Reviews of Physiology Biochemistry and Experimental Pharmacology, Volume 67</i>. Ergebnisse der Physiologie Reviews of Physiology. Vol. 67. pp. <span class="nowrap">69–</span>168. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2FBFb0036328">10.1007/BFb0036328</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/3-540-05959-8" title="Special:BookSources/3-540-05959-8"><bdi>3-540-05959-8</bdi></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/4574573">4574573</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Physiology+and+pharmacology+of+female+reproduction+under+the+aspect+of+fertility+control&rft.btitle=Reviews+of+Physiology+Biochemistry+and+Experimental+Pharmacology%2C+Volume+67&rft.series=Ergebnisse+der+Physiologie+Reviews+of+Physiology&rft.pages=%3Cspan+class%3D%22nowrap%22%3E69-%3C%2Fspan%3E168&rft.date=1972&rft_id=info%3Apmid%2F4574573&rft_id=info%3Adoi%2F10.1007%2FBFb0036328&rft.isbn=3-540-05959-8&rft.aulast=Elger&rft.aufirst=W&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-HerrRevesz1970a-23"><span class="mw-cite-backlink"><b><a href="#cite_ref-HerrRevesz1970a_23-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHerrReveszMansonJewell1970" class="citation book cs1">Herr F, Revesz C, Manson AJ, Jewell JB (1970). "Biological Properties of Estrogen Sulfates". <i>Chemical and Biological Aspects of Steroid Conjugation</i>. Springer. pp. <span class="nowrap">368–</span>408. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-3-642-49793-3_8">10.1007/978-3-642-49793-3_8</a> (inactive 2024-11-02). <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-49506-9" title="Special:BookSources/978-3-642-49506-9"><bdi>978-3-642-49506-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Biological+Properties+of+Estrogen+Sulfates&rft.btitle=Chemical+and+Biological+Aspects+of+Steroid+Conjugation&rft.pages=%3Cspan+class%3D%22nowrap%22%3E368-%3C%2Fspan%3E408&rft.pub=Springer&rft.date=1970&rft_id=info%3Adoi%2F10.1007%2F978-3-642-49793-3_8&rft.isbn=978-3-642-49506-9&rft.aulast=Herr&rft.aufirst=F&rft.au=Revesz%2C+C&rft.au=Manson%2C+AJ&rft.au=Jewell%2C+JB&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_book" title="Template:Cite book">cite book</a>}}</code>: CS1 maint: DOI inactive as of November 2024 (<a href="/wiki/Category:CS1_maint:_DOI_inactive_as_of_November_2024" title="Category:CS1 maint: DOI inactive as of November 2024">link</a>)</span></span> </li> <li id="cite_note-pmid1146927-24"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid1146927_24-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGoldzieherPenaChenaultWoutersz1975" class="citation journal cs1">Goldzieher JW, Pena A, Chenault CB, Woutersz TB (July 1975). "Comparative studies of the ethynyl estrogens used in oral contraceptives. II. Antiovulatory potency". <i>American Journal of Obstetrics and Gynecology</i>. <b>122</b> (5): <span class="nowrap">619–</span>624. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0002-9378%2875%2990061-7">10.1016/0002-9378(75)90061-7</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/1146927">1146927</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=American+Journal+of+Obstetrics+and+Gynecology&rft.atitle=Comparative+studies+of+the+ethynyl+estrogens+used+in+oral+contraceptives.+II.+Antiovulatory+potency&rft.volume=122&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E619-%3C%2Fspan%3E624&rft.date=1975-07&rft_id=info%3Adoi%2F10.1016%2F0002-9378%2875%2990061-7&rft_id=info%3Apmid%2F1146927&rft.aulast=Goldzieher&rft.aufirst=JW&rft.au=Pena%2C+A&rft.au=Chenault%2C+CB&rft.au=Woutersz%2C+TB&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-pmid2215269-25"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid2215269_25-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLauritzen1990" class="citation journal cs1">Lauritzen C (September 1990). "Clinical use of oestrogens and progestogens". <i>Maturitas</i>. <b>12</b> (3): <span class="nowrap">199–</span>214. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0378-5122%2890%2990004-P">10.1016/0378-5122(90)90004-P</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/2215269">2215269</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Maturitas&rft.atitle=Clinical+use+of+oestrogens+and+progestogens&rft.volume=12&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E199-%3C%2Fspan%3E214&rft.date=1990-09&rft_id=info%3Adoi%2F10.1016%2F0378-5122%2890%2990004-P&rft_id=info%3Apmid%2F2215269&rft.aulast=Lauritzen&rft.aufirst=C&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-pmid559617-26"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid559617_26-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLauritzen1977" class="citation journal cs1 cs1-prop-foreign-lang-source">Lauritzen C (June 1977). "[Estrogen thearpy in practice. 3. Estrogen preparations and combination preparations]" [Estrogen therapy in practice. 3. Estrogen preparations and combination preparations]. <i>Fortschritte Der Medizin</i> (in German). <b>95</b> (21): <span class="nowrap">1388–</span>92. <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/559617">559617</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Fortschritte+Der+Medizin&rft.atitle=%5BEstrogen+thearpy+in+practice.+3.+Estrogen+preparations+and+combination+preparations%5D&rft.volume=95&rft.issue=21&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1388-%3C%2Fspan%3E92&rft.date=1977-06&rft_id=info%3Apmid%2F559617&rft.aulast=Lauritzen&rft.aufirst=C&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-WolfSchneider2013-27"><span class="mw-cite-backlink"><b><a href="#cite_ref-WolfSchneider2013_27-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWolfSchneider2013" class="citation book cs1">Wolf AS, Schneider HP (12 March 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books-id=IArLBgAAQBAJ&pg=PA78"><i>Östrogene in Diagnostik und Therapie</i></a>. Springer-Verlag. pp. 78–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-75101-1" title="Special:BookSources/978-3-642-75101-1"><bdi>978-3-642-75101-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=%C3%96strogene+in+Diagnostik+und+Therapie&rft.pages=78-&rft.pub=Springer-Verlag&rft.date=2013-03-12&rft.isbn=978-3-642-75101-1&rft.aulast=Wolf&rft.aufirst=AS&rft.au=Schneider%2C+HP&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks-id%3DIArLBgAAQBAJ%26pg%3DPA78&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-GöretzlehnerLauritzen2012-28"><span class="mw-cite-backlink"><b><a href="#cite_ref-GöretzlehnerLauritzen2012_28-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGöretzlehnerLauritzenRömerRossmanith2012" class="citation book cs1">Göretzlehner G, Lauritzen C, Römer T, Rossmanith W (1 January 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books-id=TIs2WhfYzZ4C&pg=PA44"><i>Praktische Hormontherapie in der Gynäkologie</i></a>. Walter de Gruyter. pp. 44–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-11-024568-4" title="Special:BookSources/978-3-11-024568-4"><bdi>978-3-11-024568-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Praktische+Hormontherapie+in+der+Gyn%C3%A4kologie&rft.pages=44-&rft.pub=Walter+de+Gruyter&rft.date=2012-01-01&rft.isbn=978-3-11-024568-4&rft.aulast=G%C3%B6retzlehner&rft.aufirst=G&rft.au=Lauritzen%2C+C&rft.au=R%C3%B6mer%2C+T&rft.au=Rossmanith%2C+W&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks-id%3DTIs2WhfYzZ4C%26pg%3DPA44&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-KnörrBeller2013-29"><span class="mw-cite-backlink"><b><a href="#cite_ref-KnörrBeller2013_29-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKnörrBellerLauritzen2013" class="citation book cs1">Knörr K, Beller FK, Lauritzen C (17 April 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books-id=ACybBwAAQBAJ&pg=PA212"><i>Lehrbuch der Gynäkologie</i></a>. Springer-Verlag. pp. <span class="nowrap">212–</span>213. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-662-00942-0" title="Special:BookSources/978-3-662-00942-0"><bdi>978-3-662-00942-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Lehrbuch+der+Gyn%C3%A4kologie&rft.pages=%3Cspan+class%3D%22nowrap%22%3E212-%3C%2Fspan%3E213&rft.pub=Springer-Verlag&rft.date=2013-04-17&rft.isbn=978-3-662-00942-0&rft.aulast=Kn%C3%B6rr&rft.aufirst=K&rft.au=Beller%2C+FK&rft.au=Lauritzen%2C+C&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks-id%3DACybBwAAQBAJ%26pg%3DPA212&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-HorskyPresl1981-30"><span class="mw-cite-backlink"><b><a href="#cite_ref-HorskyPresl1981_30-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHorskýPresl1981" class="citation book cs1">Horský J, Presl J (1981). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=7IrpCAAAQBAJ&pg=PA310">"Hormonal Treatment of Disorders of the Menstrual Cycle"</a>. In Horsky J, Presl J (eds.). <i>Ovarian Function and its Disorders: Diagnosis and Therapy</i>. Springer Science & Business Media. pp. <span class="nowrap">309–</span>332. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-94-009-8195-9_11">10.1007/978-94-009-8195-9_11</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-94-009-8195-9" title="Special:BookSources/978-94-009-8195-9"><bdi>978-94-009-8195-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Hormonal+Treatment+of+Disorders+of+the+Menstrual+Cycle&rft.btitle=Ovarian+Function+and+its+Disorders%3A+Diagnosis+and+Therapy&rft.pages=%3Cspan+class%3D%22nowrap%22%3E309-%3C%2Fspan%3E332&rft.pub=Springer+Science+%26+Business+Media&rft.date=1981&rft_id=info%3Adoi%2F10.1007%2F978-94-009-8195-9_11&rft.isbn=978-94-009-8195-9&rft.aulast=Horsk%C3%BD&rft.aufirst=J&rft.au=Presl%2C+J&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D7IrpCAAAQBAJ%26pg%3DPA310&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-Pschyrembel1968-31"><span class="mw-cite-backlink"><b><a href="#cite_ref-Pschyrembel1968_31-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPschyrembel1968" class="citation book cs1">Pschyrembel W (1968). <a rel="nofollow" class="external text" href="https://books.google.com/books-id=vVaTnHDFzZ0C&pg=PA598"><i>Praktische Gynäkologie: für Studierende und Ärzte</i></a>. Walter de Gruyter. pp. <span class="nowrap">598–</span>599. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-11-150424-7" title="Special:BookSources/978-3-11-150424-7"><bdi>978-3-11-150424-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Praktische+Gyn%C3%A4kologie%3A+f%C3%BCr+Studierende+und+%C3%84rzte&rft.pages=%3Cspan+class%3D%22nowrap%22%3E598-%3C%2Fspan%3E599&rft.pub=Walter+de+Gruyter&rft.date=1968&rft.isbn=978-3-11-150424-7&rft.aulast=Pschyrembel&rft.aufirst=W&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks-id%3DvVaTnHDFzZ0C%26pg%3DPA598&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-pmid779393-32"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid779393_32-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLauritzen1976" class="citation journal cs1">Lauritzen CH (January 1976). "The female climacteric syndrome: significance, problems, treatment". <i>Acta Obstetricia Et Gynecologica Scandinavica. Supplement</i>. <b>51</b>: <span class="nowrap">47–</span>61. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3109%2F00016347509156433">10.3109/00016347509156433</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/779393">779393</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Obstetricia+Et+Gynecologica+Scandinavica.+Supplement&rft.atitle=The+female+climacteric+syndrome%3A+significance%2C+problems%2C+treatment&rft.volume=51&rft.pages=%3Cspan+class%3D%22nowrap%22%3E47-%3C%2Fspan%3E61&rft.date=1976-01&rft_id=info%3Adoi%2F10.3109%2F00016347509156433&rft_id=info%3Apmid%2F779393&rft.aulast=Lauritzen&rft.aufirst=CH&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-Lauritzen1975-33"><span class="mw-cite-backlink"><b><a href="#cite_ref-Lauritzen1975_33-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLauritzen1975" class="citation journal cs1">Lauritzen C (1975). "The Female Climacteric Syndrome: Significance, Problems, Treatment". <i>Acta Obstetricia et Gynecologica Scandinavica</i>. <b>54</b> (s51): <span class="nowrap">48–</span>61. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3109%2F00016347509156433">10.3109/00016347509156433</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0001-6349">0001-6349</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Obstetricia+et+Gynecologica+Scandinavica&rft.atitle=The+Female+Climacteric+Syndrome%3A+Significance%2C+Problems%2C+Treatment&rft.volume=54&rft.issue=s51&rft.pages=%3Cspan+class%3D%22nowrap%22%3E48-%3C%2Fspan%3E61&rft.date=1975&rft_id=info%3Adoi%2F10.3109%2F00016347509156433&rft.issn=0001-6349&rft.aulast=Lauritzen&rft.aufirst=C&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-Kopera1991-34"><span class="mw-cite-backlink"><b><a href="#cite_ref-Kopera1991_34-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKopera1991" class="citation book cs1">Kopera H (1991). "Hormone der Gonaden". <i>Hormonelle Therapie für die Frau</i>. Kliniktaschenbücher. pp. <span class="nowrap">59–</span>124. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-3-642-95670-6_6">10.1007/978-3-642-95670-6_6</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-540-54554-5" title="Special:BookSources/978-3-540-54554-5"><bdi>978-3-540-54554-5</bdi></a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0172-777X">0172-777X</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Hormone+der+Gonaden&rft.btitle=Hormonelle+Therapie+f%C3%BCr+die+Frau&rft.series=Kliniktaschenb%C3%BCcher&rft.pages=%3Cspan+class%3D%22nowrap%22%3E59-%3C%2Fspan%3E124&rft.date=1991&rft.issn=0172-777X&rft_id=info%3Adoi%2F10.1007%2F978-3-642-95670-6_6&rft.isbn=978-3-540-54554-5&rft.aulast=Kopera&rft.aufirst=H&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-pmid29603164-35"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid29603164_35-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFScottMenonWalsh1980" class="citation journal cs1">Scott WW, Menon M, Walsh PC (April 1980). "Hormonal Therapy of Prostatic Cancer". <i>Cancer</i>. <b>45</b> (Suppl 7): <span class="nowrap">1929–</span>1936. <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%2Fcncr.1980.45.s7.1929">10.1002/cncr.1980.45.s7.1929</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/29603164">29603164</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Cancer&rft.atitle=Hormonal+Therapy+of+Prostatic+Cancer&rft.volume=45&rft.issue=Suppl+7&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1929-%3C%2Fspan%3E1936&rft.date=1980-04&rft_id=info%3Adoi%2F10.1002%2Fcncr.1980.45.s7.1929&rft_id=info%3Apmid%2F29603164&rft.aulast=Scott&rft.aufirst=WW&rft.au=Menon%2C+M&rft.au=Walsh%2C+PC&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-pmid29756046-36"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid29756046_36-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLeinungFeustelJoseph2018" class="citation journal cs1">Leinung MC, Feustel PJ, Joseph J (2018). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5944393">"Hormonal Treatment of Transgender Women with Oral Estradiol"</a>. <i>Transgender Health</i>. <b>3</b> (1): <span class="nowrap">74–</span>81. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1089%2Ftrgh.2017.0035">10.1089/trgh.2017.0035</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/PMC5944393">5944393</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/29756046">29756046</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Transgender+Health&rft.atitle=Hormonal+Treatment+of+Transgender+Women+with+Oral+Estradiol&rft.volume=3&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E74-%3C%2Fspan%3E81&rft.date=2018&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5944393%23id-name%3DPMC&rft_id=info%3Apmid%2F29756046&rft_id=info%3Adoi%2F10.1089%2Ftrgh.2017.0035&rft.aulast=Leinung&rft.aufirst=MC&rft.au=Feustel%2C+PJ&rft.au=Joseph%2C+J&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5944393&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-Rydén1950-37"><span class="mw-cite-backlink"><b><a href="#cite_ref-Rydén1950_37-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRyden1950" class="citation journal cs1">Ryden AB (1950). "Natural and synthetic oestrogenic substances; their relative effectiveness when administered orally". <i>Acta Endocrinologica</i>. <b>4</b> (2): <span class="nowrap">121–</span>39. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1530%2Facta.0.0040121">10.1530/acta.0.0040121</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/15432047">15432047</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Endocrinologica&rft.atitle=Natural+and+synthetic+oestrogenic+substances%3B+their+relative+effectiveness+when+administered+orally&rft.volume=4&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E121-%3C%2Fspan%3E39&rft.date=1950&rft_id=info%3Adoi%2F10.1530%2Facta.0.0040121&rft_id=info%3Apmid%2F15432047&rft.aulast=Ryden&rft.aufirst=AB&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-pmid14902290-38"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid14902290_38-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRyden1951" class="citation journal cs1">Ryden AB (1951). "The effectiveness of natural and synthetic oestrogenic substances in women". <i>Acta Endocrinologica</i>. <b>8</b> (2): <span class="nowrap">175–</span>91. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1530%2Facta.0.0080175">10.1530/acta.0.0080175</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/14902290">14902290</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Endocrinologica&rft.atitle=The+effectiveness+of+natural+and+synthetic+oestrogenic+substances+in+women&rft.volume=8&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E175-%3C%2Fspan%3E91&rft.date=1951&rft_id=info%3Adoi%2F10.1530%2Facta.0.0080175&rft_id=info%3Apmid%2F14902290&rft.aulast=Ryden&rft.aufirst=AB&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-Kottmeier1947-39"><span class="mw-cite-backlink"><b><a href="#cite_ref-Kottmeier1947_39-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKottmeier1947" class="citation journal cs1">Kottmeier HL (1947). "Ueber blutungen in der menopause: Speziell der klinischen bedeutung eines endometriums mit zeichen hormonaler beeinflussung: Part I". <i>Acta Obstetricia et Gynecologica Scandinavica</i>. <b>27</b> (s6): <span class="nowrap">1–</span>121. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3109%2F00016344709154486">10.3109/00016344709154486</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0001-6349">0001-6349</a>. <q>There is no doubt that the conversion of the endometrium with injections of both synthetic and native estrogenic hormone preparations succeeds, but the opinion whether native, orally administered preparations can produce a proliferation mucosa changes with different authors. PEDERSEN-BJERGAARD (1939) was able to show that 90% of the folliculin taken up in the blood of the vena portae is inactivated in the liver. Neither KAUFMANN (1933, 1935), RAUSCHER (1939, 1942) nor HERRNBERGER (1941) succeeded in bringing a castration endometrium into proliferation using large doses of orally administered preparations of estrone or estradiol. Other results are reported by NEUSTAEDTER (1939), LAUTERWEIN (1940) and FERIN (1941); they succeeded in converting an atrophic castration endometrium into an unambiguous proliferation mucosa with 120–300 oestradiol or with 380 oestrone.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Obstetricia+et+Gynecologica+Scandinavica&rft.atitle=Ueber+blutungen+in+der+menopause%3A+Speziell+der+klinischen+bedeutung+eines+endometriums+mit+zeichen+hormonaler+beeinflussung%3A+Part+I&rft.volume=27&rft.issue=s6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1-%3C%2Fspan%3E121&rft.date=1947&rft_id=info%3Adoi%2F10.3109%2F00016344709154486&rft.issn=0001-6349&rft.aulast=Kottmeier&rft.aufirst=HL&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-RietbrockStaib2013-40"><span class="mw-cite-backlink"><b><a href="#cite_ref-RietbrockStaib2013_40-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRietbrockStaibLoew2013" class="citation book cs1">Rietbrock N, Staib AH, Loew D (11 March 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books-id=FkwEBgAAQBAJ&pg=PA426"><i>Klinische Pharmakologie: Arzneitherapie</i></a>. Springer-Verlag. pp. 426–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-57636-2" title="Special:BookSources/978-3-642-57636-2"><bdi>978-3-642-57636-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Klinische+Pharmakologie%3A+Arzneitherapie&rft.pages=426-&rft.pub=Springer-Verlag&rft.date=2013-03-11&rft.isbn=978-3-642-57636-2&rft.aulast=Rietbrock&rft.aufirst=N&rft.au=Staib%2C+AH&rft.au=Loew%2C+D&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks-id%3DFkwEBgAAQBAJ%26pg%3DPA426&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-Greenblatt1966-41"><span class="mw-cite-backlink"><b><a href="#cite_ref-Greenblatt1966_41-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMartinez-ManautouRudel1966" class="citation book cs1">Martinez-Manautou J, Rudel HW (1966). "Antiovulatory Activity of Several Synthetic and Natural Estrogens". In Robert Benjamin Greenblatt (ed.). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=le1qAAAAMAAJ"><i>Ovulation: Stimulation, Suppression, and Detection</i></a>. Lippincott. pp. <span class="nowrap">243–</span>253.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Antiovulatory+Activity+of+Several+Synthetic+and+Natural+Estrogens&rft.btitle=Ovulation%3A+Stimulation%2C+Suppression%2C+and+Detection&rft.pages=%3Cspan+class%3D%22nowrap%22%3E243-%3C%2Fspan%3E253&rft.pub=Lippincott&rft.date=1966&rft.aulast=Martinez-Manautou&rft.aufirst=J&rft.au=Rudel%2C+HW&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dle1qAAAAMAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-HerrRevesz1970-42"><span class="mw-cite-backlink"><b><a href="#cite_ref-HerrRevesz1970_42-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHerrReveszMansonJewell1970" class="citation book cs1">Herr F, Revesz C, Manson AJ, Jewell JB (1970). "Biological Properties of Estrogen Sulfates". <i>Chemical and Biological Aspects of Steroid Conjugation</i>. pp. <span class="nowrap">368–</span>408. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-3-642-49793-3_8">10.1007/978-3-642-49793-3_8</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-49506-9" title="Special:BookSources/978-3-642-49506-9"><bdi>978-3-642-49506-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Biological+Properties+of+Estrogen+Sulfates&rft.btitle=Chemical+and+Biological+Aspects+of+Steroid+Conjugation&rft.pages=%3Cspan+class%3D%22nowrap%22%3E368-%3C%2Fspan%3E408&rft.date=1970&rft_id=info%3Adoi%2F10.1007%2F978-3-642-49793-3_8&rft.isbn=978-3-642-49506-9&rft.aulast=Herr&rft.aufirst=F&rft.au=Revesz%2C+C&rft.au=Manson%2C+AJ&rft.au=Jewell%2C+JB&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-pmid13370006-43"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid13370006_43-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDuncanKistnerMansell1956" class="citation journal cs1">Duncan CJ, Kistner RW, Mansell H (October 1956). <a rel="nofollow" class="external text" href="https://journals.lww.com/greenjournal/citation/1956/10000/suppression_of_ovulation_by_tri_p_anisyl.4.aspx">"Suppression of ovulation by trip-anisyl chloroethylene (TACE)"</a>. <i>Obstetrics and Gynecology</i>. <b>8</b> (4): <span class="nowrap">399–</span>407. <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/13370006">13370006</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Obstetrics+and+Gynecology&rft.atitle=Suppression+of+ovulation+by+trip-anisyl+chloroethylene+%28TACE%29&rft.volume=8&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E399-%3C%2Fspan%3E407&rft.date=1956-10&rft_id=info%3Apmid%2F13370006&rft.aulast=Duncan&rft.aufirst=CJ&rft.au=Kistner%2C+RW&rft.au=Mansell%2C+H&rft_id=https%3A%2F%2Fjournals.lww.com%2Fgreenjournal%2Fcitation%2F1956%2F10000%2Fsuppression_of_ovulation_by_tri_p_anisyl.4.aspx&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-Elks2014-49"><span class="mw-cite-backlink">^ <a href="#cite_ref-Elks2014_49-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Elks2014_49-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Elks2014_49-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Elks2014_49-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFElks2014" class="citation book cs1">Elks J (14 November 2014). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA775"><i>The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies</i></a>. Springer. pp. 775–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4757-2085-3" title="Special:BookSources/978-1-4757-2085-3"><bdi>978-1-4757-2085-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Dictionary+of+Drugs%3A+Chemical+Data%3A+Chemical+Data%2C+Structures+and+Bibliographies&rft.pages=775-&rft.pub=Springer&rft.date=2014-11-14&rft.isbn=978-1-4757-2085-3&rft.aulast=Elks&rft.aufirst=J&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D0vXTBwAAQBAJ%26pg%3DPA775&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-IndexNominum2000-50"><span class="mw-cite-backlink">^ <a href="#cite_ref-IndexNominum2000_50-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-IndexNominum2000_50-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-IndexNominum2000_50-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-IndexNominum2000_50-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1"><a rel="nofollow" class="external text" href="https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA656"><i>Index Nominum 2000: International Drug Directory</i></a>. Taylor & Francis. 2000. pp. 656–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-88763-075-1" title="Special:BookSources/978-3-88763-075-1"><bdi>978-3-88763-075-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Index+Nominum+2000%3A+International+Drug+Directory&rft.pages=656-&rft.pub=Taylor+%26+Francis&rft.date=2000&rft.isbn=978-3-88763-075-1&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D5GpcTQD_L2oC%26pg%3DPA656&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-Labhart2012-51"><span class="mw-cite-backlink"><b><a href="#cite_ref-Labhart2012_51-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLabhart2012" class="citation book cs1">Labhart A (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=DAgJCAAAQBAJ&pg=PA575"><i>Clinical Endocrinology: Theory and Practice</i></a>. Springer Science & Business Media. pp. 575–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-96158-8" title="Special:BookSources/978-3-642-96158-8"><bdi>978-3-642-96158-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Clinical+Endocrinology%3A+Theory+and+Practice&rft.pages=575-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-3-642-96158-8&rft.aulast=Labhart&rft.aufirst=A&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DDAgJCAAAQBAJ%26pg%3DPA575&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-FilshieGuillebaud2013-52"><span class="mw-cite-backlink"><b><a href="#cite_ref-FilshieGuillebaud2013_52-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFilshieGuillebaud2013" class="citation book cs1">Filshie M, Guillebaud J (22 October 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=Ug3-BAAAQBAJ&pg=PA12"><i>Contraception: Science and Practice</i></a>. Elsevier Science. pp. 12–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4831-6366-6" title="Special:BookSources/978-1-4831-6366-6"><bdi>978-1-4831-6366-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Contraception%3A+Science+and+Practice&rft.pages=12-&rft.pub=Elsevier+Science&rft.date=2013-10-22&rft.isbn=978-1-4831-6366-6&rft.aulast=Filshie&rft.aufirst=M&rft.au=Guillebaud%2C+J&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DUg3-BAAAQBAJ%26pg%3DPA12&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-pmid4884828-53"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid4884828_53-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBillingsley1969" class="citation journal cs1">Billingsley FS (February 1969). "Lactation suppression utilizing norethynodrel with mestranol". <i>The Journal of the Florida Medical Association</i>. <b>56</b> (2): <span class="nowrap">95–</span>97. <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/4884828">4884828</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+the+Florida+Medical+Association&rft.atitle=Lactation+suppression+utilizing+norethynodrel+with+mestranol&rft.volume=56&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E95-%3C%2Fspan%3E97&rft.date=1969-02&rft_id=info%3Apmid%2F4884828&rft.aulast=Billingsley&rft.aufirst=FS&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-Publishing2013-54"><span class="mw-cite-backlink"><b><a href="#cite_ref-Publishing2013_54-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1"><a rel="nofollow" class="external text" href="https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA2109-IA88"><i>Pharmaceutical Manufacturing Encyclopedia</i></a> (3rd ed.). Elsevier. 22 October 2013. pp. 2109–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-8155-1856-3" title="Special:BookSources/978-0-8155-1856-3"><bdi>978-0-8155-1856-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Pharmaceutical+Manufacturing+Encyclopedia&rft.pages=2109-&rft.edition=3rd&rft.pub=Elsevier&rft.date=2013-10-22&rft.isbn=978-0-8155-1856-3&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D_J2ti4EkYpkC%26pg%3DPA2109-IA88&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-pmid6771777-55"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid6771777_55-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid6771777_55-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-pmid6771777_55-2"><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="CITEREFDorfman1980" class="citation journal cs1">Dorfman RI (1980). "Pharmacology of estrogens-general". <i>Pharmacology & Therapeutics</i>. <b>9</b> (1): <span class="nowrap">107–</span>119. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0163-7258%2880%2990018-2">10.1016/0163-7258(80)90018-2</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/6771777">6771777</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pharmacology+%26+Therapeutics&rft.atitle=Pharmacology+of+estrogens-general&rft.volume=9&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E107-%3C%2Fspan%3E119&rft.date=1980&rft_id=info%3Adoi%2F10.1016%2F0163-7258%2880%2990018-2&rft_id=info%3Apmid%2F6771777&rft.aulast=Dorfman&rft.aufirst=RI&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-pmid776453-56"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid776453_56-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid776453_56-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-pmid776453_56-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-pmid776453_56-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJackson1975" class="citation journal cs1">Jackson H (November 1975). "Progress towards a male oral contraceptive". <i>Clinics in Endocrinology and Metabolism</i>. <b>4</b> (3): <span class="nowrap">643–</span>663. <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%2875%2980051-X">10.1016/S0300-595X(75)80051-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/776453">776453</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=Progress+towards+a+male+oral+contraceptive&rft.volume=4&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E643-%3C%2Fspan%3E663&rft.date=1975-11&rft_id=info%3Adoi%2F10.1016%2FS0300-595X%2875%2980051-X&rft_id=info%3Apmid%2F776453&rft.aulast=Jackson&rft.aufirst=H&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-Oettel1999-57"><span class="mw-cite-backlink">^ <a href="#cite_ref-Oettel1999_57-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Oettel1999_57-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Oettel1999_57-2"><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="CITEREFOettel1999" class="citation book cs1 cs1-prop-long-vol">Oettel M (1999). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=wBvyCAAAQBAJ&pg=PA538">"Estrogens and Antiestrogens in the Male"</a>. In Oettel M, Schillinger E (eds.). <i>Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen</i>. Handbook of Experimental Pharmacology. Vol. 135 / 2. Springer Science & Business Media. pp. <span class="nowrap">505–</span>571. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-3-642-60107-1_25">10.1007/978-3-642-60107-1_25</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-60107-1" title="Special:BookSources/978-3-642-60107-1"><bdi>978-3-642-60107-1</bdi></a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0171-2004">0171-2004</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Estrogens+and+Antiestrogens+in+the+Male&rft.btitle=Estrogens+and+Antiestrogens+II%3A+Pharmacology+and+Clinical+Application+of+Estrogens+and+Antiestrogen&rft.series=Handbook+of+Experimental+Pharmacology&rft.pages=%3Cspan+class%3D%22nowrap%22%3E505-%3C%2Fspan%3E571&rft.pub=Springer+Science+%26+Business+Media&rft.date=1999&rft.issn=0171-2004&rft_id=info%3Adoi%2F10.1007%2F978-3-642-60107-1_25&rft.isbn=978-3-642-60107-1&rft.aulast=Oettel&rft.aufirst=M&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DwBvyCAAAQBAJ%26pg%3DPA538&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-pmid14400846-58"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid14400846_58-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid14400846_58-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-pmid14400846_58-2"><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="CITEREFHellerMoorePaulsenNelson1959" class="citation journal cs1">Heller CG, Moore DJ, Paulsen CA, Nelson WO, Laidlaw WM (December 1959). <a rel="nofollow" class="external text" href="https://www.popline.org/node/472874">"Effects of progesterone and synthetic progestins on the reproductive physiology of normal men"</a>. <i>Federation Proceedings</i>. <b>18</b>: <span class="nowrap">1057–</span>1065. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/14400846">14400846</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Federation+Proceedings&rft.atitle=Effects+of+progesterone+and+synthetic+progestins+on+the+reproductive+physiology+of+normal+men&rft.volume=18&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1057-%3C%2Fspan%3E1065&rft.date=1959-12&rft_id=info%3Apmid%2F14400846&rft.aulast=Heller&rft.aufirst=CG&rft.au=Moore%2C+DJ&rft.au=Paulsen%2C+CA&rft.au=Nelson%2C+WO&rft.au=Laidlaw%2C+WM&rft_id=https%3A%2F%2Fwww.popline.org%2Fnode%2F472874&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> <li id="cite_note-Black2021-59"><span class="mw-cite-backlink"><b><a href="#cite_ref-Black2021_59-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBlackHeDenisonYoung2021" class="citation journal cs1">Black GP, He G, Denison MS, Young TM (May 2021). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8378343">"Using Estrogenic Activity and Nontargeted Chemical Analysis to Identify Contaminants in Sewage Sludge"</a>. <i>Environmental Science & Technology</i>. <b>55</b> (10): <span class="nowrap">6729–</span>6739. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2021EnST...55.6729B">2021EnST...55.6729B</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Facs.est.0c07846">10.1021/acs.est.0c07846</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/PMC8378343">8378343</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/33909413">33909413</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Environmental+Science+%26+Technology&rft.atitle=Using+Estrogenic+Activity+and+Nontargeted+Chemical+Analysis+to+Identify+Contaminants+in+Sewage+Sludge&rft.volume=55&rft.issue=10&rft.pages=%3Cspan+class%3D%22nowrap%22%3E6729-%3C%2Fspan%3E6739&rft.date=2021-05&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8378343%23id-name%3DPMC&rft_id=info%3Apmid%2F33909413&rft_id=info%3Adoi%2F10.1021%2Facs.est.0c07846&rft_id=info%3Abibcode%2F2021EnST...55.6729B&rft.aulast=Black&rft.aufirst=GP&rft.au=He%2C+G&rft.au=Denison%2C+MS&rft.au=Young%2C+TM&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8378343&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMestranol" class="Z3988"></span></span> </li> </ol></div></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 .navbox{margin-top:0}.mw-parser-output .navbox+.navbox,.mw-parser-output .navbox+.navbox-styles+.navbox{margin-top:-1px}.mw-parser-output .navbox-inner,.mw-parser-output .navbox-subgroup{width:100%}.mw-parser-output .navbox-group,.mw-parser-output .navbox-title,.mw-parser-output .navbox-abovebelow{padding:0.25em 1em;line-height:1.5em;text-align:center}.mw-parser-output .navbox-group{white-space:nowrap;text-align:right}.mw-parser-output .navbox,.mw-parser-output .navbox-subgroup{background-color:#fdfdfd}.mw-parser-output .navbox-list{line-height:1.5em;border-color:#fdfdfd}.mw-parser-output .navbox-list-with-group{text-align:left;border-left-width:2px;border-left-style:solid}.mw-parser-output tr+tr>.navbox-abovebelow,.mw-parser-output tr+tr>.navbox-group,.mw-parser-output tr+tr>.navbox-image,.mw-parser-output tr+tr>.navbox-list{border-top:2px solid #fdfdfd}.mw-parser-output .navbox-title{background-color:#ccf}.mw-parser-output .navbox-abovebelow,.mw-parser-output .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><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Estrogens_and_antiestrogens109" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Estrogens_and_antiestrogens" title="Template:Estrogens and antiestrogens"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Estrogens_and_antiestrogens" title="Template talk:Estrogens and antiestrogens"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Estrogens_and_antiestrogens" title="Special:EditPage/Template:Estrogens and antiestrogens"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Estrogens_and_antiestrogens109" style="font-size:114%;margin:0 4em"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogens</a> and <a href="/wiki/Antiestrogen" title="Antiestrogen">antiestrogens</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogens</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor</span> 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/Alfatradiol" title="Alfatradiol">Alfatradiol</a></li> <li>Certain <a href="/wiki/Androgen" title="Androgen">androgens</a>/<a href="/wiki/Anabolic_steroid" title="Anabolic steroid">anabolic steroids</a> (e.g., <a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">testosterone</a>, <a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">testosterone esters</a>, <a href="/wiki/Methyltestosterone" title="Methyltestosterone">methyltestosterone</a>, <a href="/wiki/Metandienone" title="Metandienone">metandienone</a>, <a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">nandrolone esters</a>) (via estrogenic metabolites)</li> <li>Certain <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestins</a> (e.g., <a href="/wiki/Norethisterone" title="Norethisterone">norethisterone</a>, <a href="/wiki/Noretynodrel" title="Noretynodrel">noretynodrel</a>, <a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">etynodiol diacetate</a>, <a href="/wiki/Tibolone" title="Tibolone">tibolone</a>)</li> <li><a href="/wiki/Clomestrone" title="Clomestrone">Clomestrone</a></li> <li><a href="/wiki/Cloxestradiol_acetate" title="Cloxestradiol acetate">Cloxestradiol acetate</a></li> <li><a href="/wiki/Conjugated_estriol" title="Conjugated estriol">Conjugated estriol</a></li> <li><a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a></li> <li><a href="/wiki/Epiestriol" title="Epiestriol">Epiestriol</a></li> <li><a href="/wiki/Epimestrol" title="Epimestrol">Epimestrol</a></li> <li><a href="/wiki/Esterified_estrogens" title="Esterified estrogens">Esterified estrogens</a></li> <li><a href="/wiki/Estetrol_(medication)" title="Estetrol (medication)">Estetrol</a><sup>†</sup></li> <li><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a></li> <li><a href="/wiki/List_of_estrogen_esters#Estradiol_esters" title="List of estrogen esters">Estradiol esters</a> (e.g., <a href="/wiki/Estradiol_acetate" title="Estradiol acetate">estradiol acetate</a>, <a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">estradiol benzoate</a>, <a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">estradiol cypionate</a>, <a href="/wiki/Estradiol_enanthate" class="mw-redirect" title="Estradiol enanthate">estradiol enanthate</a>, <a href="/wiki/Estradiol_undecylate" title="Estradiol undecylate">estradiol undecylate</a>, <a href="/wiki/Estradiol_valerate" title="Estradiol valerate">estradiol valerate</a>, <a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">polyestradiol phosphate</a>, <a href="/wiki/Estradiol_ester_mixture" class="mw-redirect" title="Estradiol ester mixture">estradiol ester mixtures</a> (<a href="/wiki/Climacteron" class="mw-redirect" title="Climacteron">Climacteron</a>))</li> <li><a href="/wiki/Estramustine_phosphate" title="Estramustine phosphate">Estramustine phosphate</a></li> <li><a href="/wiki/Estriol_(medication)" title="Estriol (medication)">Estriol</a></li> <li><a href="/wiki/List_of_estrogen_esters#Estriol_esters" title="List of estrogen esters">Estriol esters</a> (e.g., <a href="/wiki/Estriol_succinate" title="Estriol succinate">estriol succinate</a>, <a href="/wiki/Polyestriol_phosphate" title="Polyestriol phosphate">polyestriol phosphate</a>)</li> <li><a href="/wiki/Estrogenic_substances" title="Estrogenic substances">Estrogenic substances</a></li> <li><a href="/wiki/Estrone_(medication)" title="Estrone (medication)">Estrone</a></li> <li><a href="/wiki/List_of_estrogen_esters#Estrone_esters" title="List of estrogen esters">Estrone esters</a> <ul><li><a href="/wiki/Estrone_sulfate_(medication)" title="Estrone sulfate (medication)">Estrone sulfate</a></li> <li><a href="/wiki/Estropipate" title="Estropipate">Estropipate (piperazine estrone sulfate)</a></li></ul></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a><sup>#</sup> <ul><li><a href="/wiki/Ethinylestradiol_sulfonate" title="Ethinylestradiol sulfonate">Ethinylestradiol sulfonate</a></li></ul></li> <li><a href="/wiki/Hydroxyestrone_diacetate" title="Hydroxyestrone diacetate">Hydroxyestrone diacetate</a></li> <li><a class="mw-selflink selflink">Mestranol</a></li> <li><a href="/wiki/Methylestradiol" title="Methylestradiol">Methylestradiol</a></li> <li><a href="/wiki/Moxestrol" title="Moxestrol">Moxestrol</a></li> <li><a href="/wiki/Nilestriol" title="Nilestriol">Nilestriol</a></li> <li><a href="/wiki/Prasterone" title="Prasterone">Prasterone (dehydroepiandrosterone; DHEA)</a> <ul><li><a href="/wiki/Prasterone_enanthate" title="Prasterone enanthate">Prasterone enanthate</a></li> <li><a href="/wiki/Prasterone_sulfate" title="Prasterone sulfate">Prasterone sulfate</a></li></ul></li> <li><a href="/wiki/Promestriene" title="Promestriene">Promestriene</a></li> <li><a href="/wiki/Quinestradol" title="Quinestradol">Quinestradol</a></li> <li><a href="/wiki/Quinestrol" title="Quinestrol">Quinestrol</a></li></ul> <ul><li><i>Nonsteroidal:</i> <a href="/wiki/Benzestrol" title="Benzestrol">Benzestrol</a></li> <li><a href="/wiki/Bifluranol" title="Bifluranol">Bifluranol</a></li> <li><a href="/wiki/Chlorotrianisene" title="Chlorotrianisene">Chlorotrianisene</a></li> <li><a href="/wiki/Dienestrol" title="Dienestrol">Dienestrol</a> <ul><li><a href="/wiki/Dienestrol_diacetate" title="Dienestrol diacetate">Dienestrol diacetate</a></li></ul></li> <li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol (stilbestrol)</a></li> <li><a href="/wiki/List_of_estrogen_esters#Diethylstilbestrol_esters" title="List of estrogen esters">Diethylstilbestrol esters/ethers</a> <ul><li><a href="/wiki/Dimestrol" title="Dimestrol">Dimestrol (diethylstilbestrol dimethyl ether)</a></li> <li><a href="/wiki/Fosfestrol" title="Fosfestrol">Fosfestrol (diethylstilbestrol diphosphate)</a></li> <li><a href="/wiki/Mestilbol" title="Mestilbol">Mestilbol (diethylstilbestrol monomethyl ether)</a></li></ul></li> <li><a href="/wiki/Doisynoestrol" title="Doisynoestrol">Doisynoestrol (fenocycline)</a></li> <li><a href="/wiki/Hexestrol" title="Hexestrol">Hexestrol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Hexestrol_esters" title="List of estrogen esters">Hexestrol esters</a></li></ul></li> <li><a href="/wiki/Methallenestril" title="Methallenestril">Methallenestril</a></li> <li><a href="/wiki/Methestrol" title="Methestrol">Methestrol (promethestrol)</a> <ul><li><a href="/wiki/Methestrol_dipropionate" title="Methestrol dipropionate">Methestrol dipropionate (promethestrol dipropionate)</a></li></ul></li> <li><a href="/wiki/Paroxypropione" title="Paroxypropione">Paroxypropione</a></li> <li><a href="/wiki/Quadrosilan" title="Quadrosilan">Quadrosilan</a></li> <li><a href="/wiki/Triphenylbromoethylene" title="Triphenylbromoethylene">Triphenylbromoethylene</a></li> <li><a href="/wiki/Triphenylchloroethylene" title="Triphenylchloroethylene">Triphenylchloroethylene</a></li> <li><a href="/wiki/Zeranol" title="Zeranol">Zeranol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Progonadotropin" title="Progonadotropin">Progonadotropins</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Antiandrogen" title="Antiandrogen">Antiandrogens</a> (e.g., <a href="/wiki/Bicalutamide" title="Bicalutamide">bicalutamide</a>)</li> <li><a href="/wiki/GnRH_agonist" class="mw-redirect" title="GnRH agonist"><abbr title="gonadotropin-releasing hormone">GnRH</abbr> agonists</a> (e.g., <a href="/wiki/Gonadotropin-releasing_hormone" title="Gonadotropin-releasing hormone"><abbr title="gonadotropin-releasing hormone">GnRH</abbr> (gonadorelin)</a>, <a href="/wiki/Leuprorelin" title="Leuprorelin">leuprorelin</a>)</li> <li><a href="/wiki/Gonadotropin" title="Gonadotropin">Gonadotropins</a> (e.g., <a href="/wiki/Follicle-stimulating_hormone" title="Follicle-stimulating hormone"><abbr title="follicle-stimulating hormone">FSH</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip follicle-stimulating hormone</span>, <a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone"><abbr title="luteinizing hormone">LH</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip luteinizing hormone</span>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Antiestrogen" title="Antiestrogen">Antiestrogens</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor</span> antagonists<br />(incl. <a href="/wiki/Selective_estrogen_receptor_modulators" class="mw-redirect" title="Selective estrogen receptor modulators"><abbr title="selective estrogen receptor modulators">SERMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip selective estrogen receptor modulators</span>/<a href="/wiki/Selective_estrogen_receptor_downregulators" class="mw-redirect" title="Selective estrogen receptor downregulators"><abbr title="selective estrogen receptor downregulators">SERDs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip selective estrogen receptor downregulators</span>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acolbifene" title="Acolbifene">Acolbifene</a><sup>†</sup></li> <li><a href="/wiki/Anordrin" title="Anordrin">Anordrin</a></li> <li><a href="/wiki/Bazedoxifene" title="Bazedoxifene">Bazedoxifene</a></li> <li><a href="/wiki/Broparestrol" title="Broparestrol">Broparestrol</a></li> <li><a href="/wiki/Clomifene" title="Clomifene">Clomifene</a><sup>#</sup></li> <li><a href="/wiki/Cyclofenil" title="Cyclofenil">Cyclofenil</a></li> <li><a href="/wiki/Enclomifene" title="Enclomifene">Enclomifene</a><sup>†</sup></li> <li><a href="/wiki/Epitiostanol" title="Epitiostanol">Epitiostanol</a></li> <li><a href="/wiki/Lasofoxifene" title="Lasofoxifene">Lasofoxifene</a></li> <li><a href="/wiki/Mepitiostane" title="Mepitiostane">Mepitiostane</a></li> <li><a href="/wiki/Ormeloxifene" title="Ormeloxifene">Ormeloxifene</a></li> <li><a href="/wiki/Ospemifene" title="Ospemifene">Ospemifene</a></li> <li><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a><sup>#</sup></li> <li><a href="/wiki/Toremifene" title="Toremifene">Toremifene</a></li></ul> <ul><li><i>Exclusively antagonistic:</i> <a href="/wiki/Elacestrant" title="Elacestrant">Elacestrant</a></li> <li><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant</a></li></ul> <ul><li><i>Noncompetitive inhibitors:</i> <a href="/wiki/Trilostane" title="Trilostane">Trilostane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Aromatase_inhibitor" title="Aromatase inhibitor">Aromatase inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>First-generation:</i> <a href="/wiki/Aminoglutethimide" title="Aminoglutethimide">Aminoglutethimide</a></li> <li><a href="/wiki/Testolactone" title="Testolactone">Testolactone</a></li></ul> <ul><li><i>Second-generation:</i> <a href="/wiki/Fadrozole" title="Fadrozole">Fadrozole</a></li> <li><a href="/wiki/Formestane" title="Formestane">Formestane</a></li></ul> <ul><li><i>Third-generation:</i> <a href="/wiki/Anastrozole" title="Anastrozole">Anastrozole</a></li> <li><a href="/wiki/Exemestane" title="Exemestane">Exemestane</a></li> <li><a href="/wiki/Letrozole" title="Letrozole">Letrozole</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Antigonadotropin" title="Antigonadotropin">Antigonadotropins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Androgen" title="Androgen">Androgens</a>/<a href="/wiki/Anabolic_steroid" title="Anabolic steroid">anabolic steroids</a> (e.g., <a href="/wiki/Testosterone" title="Testosterone">testosterone</a>, <a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">testosterone esters</a>, <a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">nandrolone esters</a>, <a href="/wiki/Oxandrolone" title="Oxandrolone">oxandrolone</a>, <a href="/wiki/Fluoxymesterone" title="Fluoxymesterone">fluoxymesterone</a>)</li> <li><a href="/wiki/D2_receptor" class="mw-redirect" title="D2 receptor">D<sub>2</sub> receptor</a> <a href="/wiki/Dopamine_antagonist" title="Dopamine antagonist">antagonists</a> (<a href="/wiki/Prolactin" title="Prolactin">prolactin</a> releasers) (e.g., <a href="/wiki/Domperidone" title="Domperidone">domperidone</a>, <a href="/wiki/Metoclopramide" title="Metoclopramide">metoclopramide</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>, <a href="/wiki/Haloperidol" title="Haloperidol">haloperidol</a>, <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>, <a href="/wiki/Sulpiride" title="Sulpiride">sulpiride</a>)</li> <li><a href="/wiki/GnRH_agonist" class="mw-redirect" title="GnRH agonist"><abbr title="gonadotropin-releasing hormone">GnRH</abbr> agonists</a> (e.g., <a href="/wiki/Leuprorelin" title="Leuprorelin">leuprorelin</a>, <a href="/wiki/Goserelin" title="Goserelin">goserelin</a>)</li> <li><a href="/wiki/GnRH_antagonist" class="mw-redirect" title="GnRH antagonist"><abbr title="gonadotropin-releasing hormone">GnRH</abbr> antagonists</a> (e.g., <a href="/wiki/Cetrorelix" title="Cetrorelix">cetrorelix</a>, <a href="/wiki/Elagolix" title="Elagolix">elagolix</a>)</li> <li><a href="/wiki/Progestogen" title="Progestogen">Progestogens</a> (e.g., <a href="/wiki/Chlormadinone_acetate" title="Chlormadinone acetate">chlormadinone acetate</a>, <a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">cyproterone acetate</a>, <a href="/wiki/Gestonorone_caproate" title="Gestonorone caproate">gestonorone caproate</a>, <a href="/wiki/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">hydroxyprogesterone caproate</a>, <a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">medroxyprogesterone acetate</a>, <a href="/wiki/Megestrol_acetate" title="Megestrol acetate">megestrol acetate</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Mixed mechanism of action:</i> <a href="/wiki/Danazol" title="Danazol">Danazol</a></li> <li><a href="/wiki/Gestrinone" title="Gestrinone">Gestrinone</a></li></ul> <ul><li><i>Androstenedione immunogens:</i> <a href="/wiki/Androvax" title="Androvax">Androvax (androstenedione albumin)</a></li> <li><a href="/wiki/Ovandrotone_albumin" title="Ovandrotone albumin">Ovandrotone albumin (Fecundin)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators">Estrogen receptor modulators</a></dd> <dd><a href="/wiki/Template:Androgens_and_antiandrogens" title="Template:Androgens and antiandrogens">Androgens and antiandrogens</a></dd> <dd><a href="/wiki/Template:Progestogens_and_antiprogestogens" title="Template:Progestogens and antiprogestogens">Progestogens and antiprogestogens</a></dd> <dd><a href="/wiki/List_of_steroidal_estrogens" class="mw-redirect" title="List of steroidal estrogens">List of estrogens</a></dd></dl></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Estrogen_receptor_modulators1222" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Estrogen_receptor_modulators" title="Template talk:Estrogen receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Estrogen_receptor_modulators" title="Special:EditPage/Template:Estrogen receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Estrogen_receptor_modulators1222" style="font-size:114%;margin:0 4em"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor">Estrogen receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Steroidal:</i> <a href="/wiki/2-Hydroxyestradiol" title="2-Hydroxyestradiol">2-Hydroxyestradiol</a></li> <li><a href="/wiki/2-Hydroxyestrone" title="2-Hydroxyestrone">2-Hydroxyestrone</a></li> <li><a href="/wiki/3-Methyl-19-methyleneandrosta-3,5-dien-17%CE%B2-ol" title="3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol">3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol</a></li> <li><a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/w/index.php?title=3%CE%B1,5%CE%B1-Dihydrolevonorgestrel&action=edit&redlink=1" class="new" title="3α,5α-Dihydrolevonorgestrel (page does not exist)">3α,5α-Dihydrolevonorgestrel</a></li> <li><a href="/w/index.php?title=3%CE%B2,5%CE%B1-Dihydrolevonorgestrel&action=edit&redlink=1" class="new" title="3β,5α-Dihydrolevonorgestrel (page does not exist)">3β,5α-Dihydrolevonorgestrel</a></li> <li><a href="/wiki/3%CE%B1-Hydroxytibolone" title="3α-Hydroxytibolone">3α-Hydroxytibolone</a></li> <li><a href="/wiki/3%CE%B2-Hydroxytibolone" title="3β-Hydroxytibolone">3β-Hydroxytibolone</a></li> <li><a href="/wiki/3%CE%B2-Androstanediol" title="3β-Androstanediol">3β-Androstanediol</a></li> <li><a href="/wiki/4-Androstenediol" title="4-Androstenediol">4-Androstenediol</a></li> <li><a href="/wiki/4-Androstenedione" class="mw-redirect" title="4-Androstenedione">4-Androstenedione</a></li> <li><a href="/wiki/4-Fluoroestradiol" title="4-Fluoroestradiol">4-Fluoroestradiol</a></li> <li><a href="/wiki/4-Hydroxyestradiol" title="4-Hydroxyestradiol">4-Hydroxyestradiol</a></li> <li><a href="/wiki/4-Hydroxyestrone" title="4-Hydroxyestrone">4-Hydroxyestrone</a></li> <li><a href="/wiki/4-Methoxyestradiol" title="4-Methoxyestradiol">4-Methoxyestradiol</a></li> <li><a href="/wiki/4-Methoxyestrone" title="4-Methoxyestrone">4-Methoxyestrone</a></li> <li><a href="/wiki/5-Androstenediol" class="mw-redirect" title="5-Androstenediol">5-Androstenediol</a></li> <li><a href="/wiki/7-Keto-DHEA" title="7-Keto-DHEA">7-Oxo-DHEA</a></li> <li><a href="/wiki/7%CE%B1-Hydroxy-DHEA" title="7α-Hydroxy-DHEA">7α-Hydroxy-DHEA</a></li> <li><a href="/wiki/7%CE%B1-Methylestradiol" title="7α-Methylestradiol">7α-Methylestradiol</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/8,9-Dehydroestradiol" title="8,9-Dehydroestradiol">8,9-Dehydroestradiol</a></li> <li><a href="/wiki/8,9-Dehydroestrone" title="8,9-Dehydroestrone">8,9-Dehydroestrone</a></li> <li><a href="/wiki/8%CE%B2-VE2" title="8β-VE2">8β-VE2</a></li> <li><a href="/wiki/10%CE%B2,17%CE%B2-Dihydroxyestra-1,4-dien-3-one" title="10β,17β-Dihydroxyestra-1,4-dien-3-one">10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)</a></li> <li><a href="/wiki/11%CE%B2-Chloromethylestradiol" title="11β-Chloromethylestradiol">11β-Chloromethylestradiol</a></li> <li><a href="/wiki/11%CE%B2-Methoxyestradiol" title="11β-Methoxyestradiol">11β-Methoxyestradiol</a></li> <li><a href="/wiki/15%CE%B1-Hydroxyestradiol" title="15α-Hydroxyestradiol">15α-Hydroxyestradiol</a></li> <li><a href="/wiki/16-Ketoestradiol" title="16-Ketoestradiol">16-Ketoestradiol</a></li> <li><a href="/wiki/16-Ketoestrone" title="16-Ketoestrone">16-Ketoestrone</a></li> <li><a href="/wiki/16%CE%B1-Fluoroestradiol" class="mw-redirect" title="16α-Fluoroestradiol">16α-Fluoroestradiol</a></li> <li><a href="/wiki/16%CE%B1-Hydroxy-DHEA" title="16α-Hydroxy-DHEA">16α-Hydroxy-DHEA</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyestrone" title="16α-Hydroxyestrone">16α-Hydroxyestrone</a></li> <li><a href="/wiki/16%CE%B1-Iodoestradiol" class="mw-redirect" title="16α-Iodoestradiol">16α-Iodoestradiol</a></li> <li><a href="/wiki/16%CE%B1-LE2" title="16α-LE2">16α-LE2</a></li> <li><a href="/wiki/16%CE%B2-Hydroxyestrone" title="16β-Hydroxyestrone">16β-Hydroxyestrone</a></li> <li><a href="/wiki/16%CE%B2,17%CE%B1-Epiestriol" title="16β,17α-Epiestriol">16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)</a></li> <li><a href="/wiki/17%CE%B1-Estradiol" title="17α-Estradiol">17α-Estradiol</a> (<a href="/wiki/Alfatradiol" title="Alfatradiol">alfatradiol</a>)</li> <li><a href="/wiki/17%CE%B1-Dihydroequilenin" title="17α-Dihydroequilenin">17α-Dihydroequilenin</a></li> <li><a href="/wiki/17%CE%B1-Dihydroequilin" title="17α-Dihydroequilin">17α-Dihydroequilin</a></li> <li><a href="/wiki/17%CE%B1-Epiestriol" title="17α-Epiestriol">17α-Epiestriol (16α-hydroxy-17α-estradiol)</a></li> <li><a href="/wiki/17%CE%B1-Ethynyl-3%CE%B1-androstanediol" title="17α-Ethynyl-3α-androstanediol">17α-Ethynyl-3α-androstanediol</a></li> <li><a href="/wiki/17%CE%B1-Ethynyl-3%CE%B2-androstanediol" title="17α-Ethynyl-3β-androstanediol">17α-Ethynyl-3β-androstanediol</a></li> <li><a href="/wiki/17%CE%B2-Dihydroequilenin" title="17β-Dihydroequilenin">17β-Dihydroequilenin</a></li> <li><a href="/wiki/17%CE%B2-Dihydroequilin" title="17β-Dihydroequilin">17β-Dihydroequilin</a></li> <li><a href="/wiki/17%CE%B2-Methyl-17%CE%B1-dihydroequilenin" title="17β-Methyl-17α-dihydroequilenin">17β-Methyl-17α-dihydroequilenin</a></li> <li><a href="/wiki/Abiraterone" class="mw-redirect" title="Abiraterone">Abiraterone</a></li> <li><a href="/wiki/Abiraterone_acetate" title="Abiraterone acetate">Abiraterone acetate</a></li> <li><a href="/wiki/Alestramustine" title="Alestramustine">Alestramustine</a></li> <li><a href="/wiki/Almestrone" title="Almestrone">Almestrone</a></li> <li><a href="/wiki/Anabolic_steroid" title="Anabolic steroid">Anabolic steroids</a> (e.g., <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> and <a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">esters</a>, <a href="/wiki/Methyltestosterone" title="Methyltestosterone">methyltestosterone</a>, <a href="/wiki/Metandienone" title="Metandienone">metandienone (methandrostenolone)</a>, <a href="/wiki/Nandrolone" title="Nandrolone">nandrolone</a> and <a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">esters</a>, many others; via estrogenic metabolites)</li> <li><a href="/wiki/Atrimustine" title="Atrimustine">Atrimustine</a></li> <li><a href="/wiki/Bolandiol" title="Bolandiol">Bolandiol</a></li> <li><a href="/wiki/Bolandiol_dipropionate" title="Bolandiol dipropionate">Bolandiol dipropionate</a></li> <li><a href="/wiki/Butolame" title="Butolame">Butolame</a></li> <li><a href="/wiki/Clomestrone" title="Clomestrone">Clomestrone</a></li> <li><a href="/wiki/Cloxestradiol" title="Cloxestradiol">Cloxestradiol</a> <ul><li><a href="/wiki/Cloxestradiol_acetate" title="Cloxestradiol acetate">Cloxestradiol acetate</a></li></ul></li> <li><a href="/wiki/Conjugated_estriol" title="Conjugated estriol">Conjugated estriol</a></li> <li><a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a></li> <li><a href="/wiki/Cyclodiol" title="Cyclodiol">Cyclodiol</a></li> <li><a href="/wiki/Cyclotriol" title="Cyclotriol">Cyclotriol</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA-S</a></li> <li><a href="/wiki/Ent-Estradiol" title="Ent-Estradiol"><i>ent</i>-Estradiol</a></li> <li><a href="/wiki/Epiestriol" title="Epiestriol">Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)</a></li> <li><a href="/wiki/Epimestrol" title="Epimestrol">Epimestrol</a></li> <li><a href="/wiki/Equilenin" title="Equilenin">Equilenin</a></li> <li><a href="/wiki/Equilin" title="Equilin">Equilin</a></li> <li><a href="/wiki/ERA-63" title="ERA-63">ERA-63 (ORG-37663)</a></li> <li><a href="/wiki/Esterified_estrogens" title="Esterified estrogens">Esterified estrogens</a></li> <li><a href="/wiki/Estetrol" title="Estetrol">Estetrol</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estradiol_esters" title="List of estrogen esters">Estradiol esters</a></li> <li><a href="/wiki/Lipoidal_estradiol" title="Lipoidal estradiol">Lipoidal estradiol</a></li> <li><a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">Polyestradiol phosphate</a></li></ul></li> <li><a href="/wiki/Estramustine" title="Estramustine">Estramustine</a></li> <li><a href="/wiki/Estramustine_phosphate" title="Estramustine phosphate">Estramustine phosphate</a></li> <li><a href="/wiki/Estrapronicate" title="Estrapronicate">Estrapronicate</a></li> <li><a href="/wiki/Estrazinol" title="Estrazinol">Estrazinol</a></li> <li><a href="/wiki/Estriol" title="Estriol">Estriol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estriol_esters" title="List of estrogen esters">Estriol esters</a></li> <li><a href="/wiki/Polyestriol_phosphate" title="Polyestriol phosphate">Polyestriol phosphate</a></li></ul></li> <li><a href="/wiki/Estrofurate" title="Estrofurate">Estrofurate</a></li> <li><a href="/wiki/Estrogenic_substances" title="Estrogenic substances">Estrogenic substances</a></li> <li><a href="/wiki/Estromustine" title="Estromustine">Estromustine</a></li> <li><a href="/wiki/Estrone" title="Estrone">Estrone</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estrone_esters" title="List of estrogen esters">Estrone esters</a></li> <li><a href="/wiki/Estrone_methyl_ether" title="Estrone methyl ether">Estrone methyl ether</a></li> <li><a href="/wiki/Estropipate" title="Estropipate">Estropipate</a></li></ul></li> <li><a href="/wiki/Etamestrol" title="Etamestrol">Etamestrol (eptamestrol)</a></li> <li><a href="/wiki/Ethinylandrostenediol" title="Ethinylandrostenediol">Ethinylandrostenediol</a> <ul><li><a href="/wiki/Ethandrostate" title="Ethandrostate">Ethandrostate</a></li></ul></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a> <ul><li><a href="/wiki/Ethinylestradiol_3-benzoate" class="mw-redirect" title="Ethinylestradiol 3-benzoate">Ethinylestradiol 3-benzoate</a></li> <li><a href="/wiki/Ethinylestradiol_sulfonate" title="Ethinylestradiol sulfonate">Ethinylestradiol sulfonate</a></li></ul></li> <li><a href="/wiki/Ethinylestriol" title="Ethinylestriol">Ethinylestriol</a></li> <li><a href="/wiki/Ethylestradiol" title="Ethylestradiol">Ethylestradiol</a></li> <li><a href="/wiki/Etynodiol" title="Etynodiol">Etynodiol</a></li> <li><a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">Etynodiol diacetate</a></li> <li><a href="/wiki/Hexolame" title="Hexolame">Hexolame</a></li> <li><a href="/wiki/Hippulin" title="Hippulin">Hippulin</a></li> <li><a href="/wiki/Hydroxyestrone_diacetate" title="Hydroxyestrone diacetate">Hydroxyestrone diacetate</a></li> <li><a href="/wiki/Lynestrenol" title="Lynestrenol">Lynestrenol</a></li> <li><a href="/wiki/Lynestrenol_phenylpropionate" title="Lynestrenol phenylpropionate">Lynestrenol phenylpropionate</a></li> <li><a class="mw-selflink selflink">Mestranol</a></li> <li><a href="/wiki/Methylestradiol" title="Methylestradiol">Methylestradiol</a></li> <li><a href="/wiki/Moxestrol" title="Moxestrol">Moxestrol</a></li> <li><a href="/wiki/Mytatrienediol" title="Mytatrienediol">Mytatrienediol</a></li> <li><a href="/wiki/Nilestriol" title="Nilestriol">Nilestriol</a></li> <li><a href="/wiki/Norethisterone" title="Norethisterone">Norethisterone</a></li> <li><a href="/wiki/Noretynodrel" title="Noretynodrel">Noretynodrel</a></li> <li><a href="/wiki/Orestrate" title="Orestrate">Orestrate</a></li> <li><a href="/wiki/Pentolame" title="Pentolame">Pentolame</a></li> <li><a href="/wiki/Prodiame" title="Prodiame">Prodiame</a></li> <li><a href="/wiki/Prolame" title="Prolame">Prolame</a></li> <li><a href="/wiki/Promestriene" title="Promestriene">Promestriene</a></li> <li><a href="/wiki/RU-16117" title="RU-16117">RU-16117</a></li> <li><a href="/wiki/Quinestradol" title="Quinestradol">Quinestradol</a></li> <li><a href="/wiki/Quinestrol" title="Quinestrol">Quinestrol</a></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li></ul> <ul><li><i>Nonsteroidal:</i> <a href="/wiki/(R,R)-Tetrahydrochrysene" title="(R,R)-Tetrahydrochrysene">(R,R)-THC</a></li> <li><a href="/wiki/(S,S)-Tetrahydrochrysene" title="(S,S)-Tetrahydrochrysene">(S,S)-THC</a></li> <li><a href="/wiki/2,8-Dihydroxyhexahydrochrysene" title="2,8-Dihydroxyhexahydrochrysene">2,8-DHHHC</a></li> <li><a href="/w/index.php?title=%CE%92-LGND1&action=edit&redlink=1" class="new" title="Β-LGND1 (page does not exist)">β-LGND1</a></li> <li><a href="/wiki/%CE%92-LGND2" title="Β-LGND2">β-LGND2 (GTx-878)</a></li> <li><a href="/w/index.php?title=AC-186&action=edit&redlink=1" class="new" title="AC-186 (page does not exist)">AC-186</a></li> <li><a href="/wiki/Allenestrol" title="Allenestrol">Allenestrol</a></li> <li><a href="/wiki/Allenolic_acid" title="Allenolic acid">Allenolic acid</a></li> <li><a href="/wiki/Benzestrol" title="Benzestrol">Benzestrol</a></li> <li><a href="/wiki/Bifluranol" title="Bifluranol">Bifluranol</a></li> <li><a href="/wiki/Bisdehydrodoisynolic_acid" title="Bisdehydrodoisynolic acid">Bisdehydrodoisynolic acid</a></li> <li><a href="/wiki/Butestrol" title="Butestrol">Butestrol</a></li> <li><a href="/wiki/Carbestrol" title="Carbestrol">Carbestrol</a></li> <li><a href="/wiki/D-15414" title="D-15414">D-15414</a></li> <li><a href="/wiki/DCW234" title="DCW234">DCW234</a></li> <li><a href="/wiki/Diarylpropionitrile" title="Diarylpropionitrile">Diarylpropionitrile</a></li> <li><a href="/wiki/Dienestrol" title="Dienestrol">Dienestrol</a> <ul><li><a href="/wiki/Dienestrol_diacetate" title="Dienestrol diacetate">Dienestrol diacetate</a></li></ul></li> <li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Diethylstilbestrol_esters" title="List of estrogen esters">Diethylstilbestrol esters</a></li></ul></li> <li><a href="/wiki/Dimestrol" title="Dimestrol">Dimestrol (dianisylhexene)</a></li> <li><a href="/wiki/Dimethylstilbestrol" title="Dimethylstilbestrol">Dimethylstilbestrol</a></li> <li><a href="/wiki/Doisynoestrol" title="Doisynoestrol">Doisynoestrol (fenocycline)</a></li> <li><a href="/wiki/Doisynolic_acid" title="Doisynolic acid">Doisynolic acid</a></li> <li><a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Elacestrant" title="Elacestrant">Elacestrant</a></li> <li><a href="/wiki/ERB-196" title="ERB-196">ERB-196 (WAY-202196)</a></li> <li><a href="/wiki/Erteberel" title="Erteberel">Erteberel (SERBA-1, LY-500307)</a></li> <li><a href="/wiki/Estrobin" title="Estrobin">Estrobin (DBE)</a></li> <li><a href="/wiki/Fenestrel" title="Fenestrel">Fenestrel</a></li> <li><a href="/wiki/FERb_033" title="FERb 033">FERb 033</a></li> <li><a href="/wiki/Fosfestrol" title="Fosfestrol">Fosfestrol (diethylstilbestrol diphosphate)</a></li> <li><a href="/wiki/Furostilbestrol" title="Furostilbestrol">Furostilbestrol (diethylstilbestrol difuroate)</a></li> <li><a href="/wiki/GTx-758" title="GTx-758">GTx-758</a></li> <li><a href="/wiki/Hexestrol" title="Hexestrol">Hexestrol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Hexestrol_esters" title="List of estrogen esters">Hexestrol esters</a></li></ul></li> <li><a href="/wiki/ICI-85966" title="ICI-85966">ICI-85966 (Stilbostat)</a></li> <li><a href="/wiki/M2613" title="M2613">M2613</a></li> <li><a href="/wiki/Meso-Butestrol" title="Meso-Butestrol"><i>meso</i>-Butestrol</a></li> <li><a href="/wiki/Meso-Hexestrol" class="mw-redirect" title="Meso-Hexestrol"><i>meso</i>-Hexestrol</a></li> <li><a href="/wiki/Mestilbol" title="Mestilbol">Mestilbol</a></li> <li><a href="/wiki/Methallenestril" title="Methallenestril">Methallenestril</a></li> <li><a href="/wiki/Methestrol" title="Methestrol">Methestrol</a></li> <li><a href="/wiki/Methestrol_dipropionate" title="Methestrol dipropionate">Methestrol dipropionate</a></li> <li><a href="/wiki/Paroxypropione" title="Paroxypropione">Paroxypropione</a></li> <li><a href="/wiki/Pentafluranol" title="Pentafluranol">Pentafluranol</a></li> <li><a href="/wiki/Phenestrol" title="Phenestrol">Phenestrol</a></li> <li><a href="/wiki/Prinaberel" title="Prinaberel">Prinaberel (ERB-041, WAY-202041)</a></li> <li><a href="/wiki/Propylpyrazoletriol" title="Propylpyrazoletriol">Propylpyrazoletriol</a></li> <li><a href="/wiki/Quadrosilan" title="Quadrosilan">Quadrosilan</a></li> <li><a href="/w/index.php?title=SC-3296&action=edit&redlink=1" class="new" title="SC-3296 (page does not exist)">SC-3296</a></li> <li><a href="/wiki/SC-4289" title="SC-4289">SC-4289</a></li> <li><a href="/wiki/SERBA-2" title="SERBA-2">SERBA-2</a></li> <li><a href="/wiki/SKF-82,958" title="SKF-82,958">SKF-82,958</a></li> <li><a href="/wiki/Terfluranol" title="Terfluranol">Terfluranol</a></li> <li><a href="/wiki/Triphenylbromoethylene" title="Triphenylbromoethylene">Triphenylbromoethylene</a></li> <li><a href="/wiki/Triphenylchloroethylene" title="Triphenylchloroethylene">Triphenylchloroethylene</a></li> <li><a href="/wiki/Triphenyliodoethylene" title="Triphenyliodoethylene">Triphenyliodoethylene</a></li> <li><a href="/wiki/Triphenylmethylethylene" title="Triphenylmethylethylene">Triphenylmethylethylene (triphenylpropene)</a></li> <li><a href="/wiki/WAY-166818" title="WAY-166818">WAY-166818</a></li> <li><a href="/w/index.php?title=WAY-169916&action=edit&redlink=1" class="new" title="WAY-169916 (page does not exist)">WAY-169916</a></li> <li><a href="/wiki/WAY-200070" title="WAY-200070">WAY-200070</a></li> <li><a href="/wiki/WAY-204688" title="WAY-204688">WAY-204688 (SIM-688)</a></li> <li><a href="/wiki/WAY-214156" title="WAY-214156">WAY-214156</a></li></ul> <ul><li><i>Unknown/unsorted:</i> <a href="/wiki/ERB-26" title="ERB-26">ERB-26</a></li> <li><a href="/wiki/ERA-45" title="ERA-45">ERA-45</a></li> <li><a href="/wiki/ERB-79" title="ERB-79">ERB-79</a></li> <li><a href="/wiki/ZK-283197" title="ZK-283197">ZK-283197</a></li></ul> <ul><li><i>Xenoestrogens:</i> <a href="/wiki/Anise" title="Anise">Anise</a>-related (e.g., <a href="/wiki/Anethole" title="Anethole">anethole</a>, <a href="/wiki/Anol" title="Anol">anol</a>, <a href="/wiki/Dianethole" title="Dianethole">dianethole</a>, <a href="/wiki/Dianol" title="Dianol">dianol</a>, <a href="/wiki/Photoanethole" title="Photoanethole">photoanethole</a>)</li> <li><a href="/wiki/Chalconoid" title="Chalconoid">Chalconoids</a> (e.g., <a href="/wiki/Isoliquiritigenin" title="Isoliquiritigenin">isoliquiritigenin</a>, <a href="/wiki/Phloretin" title="Phloretin">phloretin</a>, <a href="/wiki/Phlorizin" title="Phlorizin">phlorizin (phloridzin)</a>, <a href="/wiki/Wedelolactone" title="Wedelolactone">wedelolactone</a>)</li> <li><a href="/wiki/Coumestan" title="Coumestan">Coumestans</a> (e.g., <a href="/wiki/Coumestrol" title="Coumestrol">coumestrol</a>, <a href="/wiki/Psoralidin" title="Psoralidin">psoralidin</a>)</li> <li><a href="/wiki/Flavonoid" title="Flavonoid">Flavonoids</a> (incl. <a href="/wiki/7,8-Dihydroxyflavone" class="mw-redirect" title="7,8-Dihydroxyflavone">7,8-DHF</a>, <a href="/wiki/8-Prenylnaringenin" title="8-Prenylnaringenin">8-prenylnaringenin</a>, <a href="/wiki/Apigenin" title="Apigenin">apigenin</a>, <a href="/wiki/Baicalein" title="Baicalein">baicalein</a>, <a href="/wiki/Baicalin" title="Baicalin">baicalin</a>, <a href="/wiki/Biochanin_A" title="Biochanin A">biochanin A</a>, <a href="/wiki/Calycosin" title="Calycosin">calycosin</a>, <a href="/wiki/Catechin" title="Catechin">catechin</a>, <a href="/wiki/Daidzein" title="Daidzein">daidzein</a>, <a href="/wiki/Daidzin" title="Daidzin">daidzin</a>, <a href="/wiki/Epicatechin_gallate" title="Epicatechin gallate">ECG</a>, <a href="/wiki/Epigallocatechin_gallate" title="Epigallocatechin gallate">EGCG</a>, <a href="/wiki/Epicatechin" class="mw-redirect" title="Epicatechin">epicatechin</a>, <a href="/wiki/Equol" title="Equol">equol</a>, <a href="/wiki/Formononetin" title="Formononetin">formononetin</a>, <a href="/wiki/Glabrene" title="Glabrene">glabrene</a>, <a href="/wiki/Glabridin" title="Glabridin">glabridin</a>, <a href="/wiki/Genistein" title="Genistein">genistein</a>, <a href="/wiki/Genistin" title="Genistin">genistin</a>, <a href="/wiki/Glycitein" title="Glycitein">glycitein</a>, <a href="/wiki/Kaempferol" title="Kaempferol">kaempferol</a>, <a href="/wiki/Liquiritigenin" title="Liquiritigenin">liquiritigenin</a>, <a href="/wiki/Mirificin" title="Mirificin">mirificin</a>, <a href="/wiki/Myricetin" title="Myricetin">myricetin</a>, <a href="/wiki/Naringenin" title="Naringenin">naringenin</a>, <a href="/w/index.php?title=Penduletin&action=edit&redlink=1" class="new" title="Penduletin (page does not exist)">penduletin</a>, <a href="/wiki/Pinocembrin" title="Pinocembrin">pinocembrin</a>, <a href="/wiki/Prunetin" title="Prunetin">prunetin</a>, <a href="/wiki/Puerarin" title="Puerarin">puerarin</a>, <a href="/wiki/Quercetin" title="Quercetin">quercetin</a>, <a href="/wiki/Tectoridin" title="Tectoridin">tectoridin</a>, <a href="/wiki/Tectorigenin" title="Tectorigenin">tectorigenin</a>)</li> <li><a href="/wiki/Lavender_oil" title="Lavender oil">Lavender oil</a></li> <li><a href="/wiki/Lignan" title="Lignan">Lignans</a> (e.g., <a href="/wiki/Enterodiol" title="Enterodiol">enterodiol</a>, <a href="/wiki/Enterolactone" title="Enterolactone">enterolactone</a>, <a href="/wiki/Nyasol" title="Nyasol">nyasol (<i>cis</i>-hinokiresinol)</a>)</li> <li><a href="/wiki/Metalloestrogen" title="Metalloestrogen">Metalloestrogens</a> (e.g., <a href="/wiki/Cadmium" title="Cadmium">cadmium</a>)</li> <li><a href="/wiki/Pesticide" title="Pesticide">Pesticides</a> (e.g., <a href="/wiki/Alternariol" title="Alternariol">alternariol</a>, <a href="/wiki/Dieldrin" title="Dieldrin">dieldrin</a>, <a href="/wiki/Endosulfan" title="Endosulfan">endosulfan</a>, <a href="/wiki/Fenarimol" title="Fenarimol">fenarimol</a>, <a href="/wiki/HPTE" title="HPTE">HPTE</a>, <a href="/wiki/Methiocarb" title="Methiocarb">methiocarb</a>, <a href="/wiki/Methoxychlor" title="Methoxychlor">methoxychlor</a>, <a href="/wiki/Triclocarban" title="Triclocarban">triclocarban</a>, <a href="/wiki/Triclosan" title="Triclosan">triclosan</a>)</li> <li><a href="/wiki/Phytosteroid" title="Phytosteroid">Phytosteroids</a> (e.g., <a href="/wiki/Digitoxin" title="Digitoxin">digitoxin</a> (<a href="/wiki/Digitalis" title="Digitalis">digitalis</a>), <a href="/wiki/Diosgenin" title="Diosgenin">diosgenin</a>, <a href="/wiki/Guggulsterone" title="Guggulsterone">guggulsterone</a>)</li> <li><a href="/wiki/Phytosterol" title="Phytosterol">Phytosterols</a> (e.g., <a href="/wiki/%CE%92-sitosterol" class="mw-redirect" title="Β-sitosterol">β-sitosterol</a>, <a href="/wiki/Campesterol" title="Campesterol">campesterol</a>, <a href="/wiki/Stigmasterol" title="Stigmasterol">stigmasterol</a>)</li> <li><a href="/wiki/Resorcylic_acid_lactone" title="Resorcylic acid lactone">Resorcylic acid lactones</a> (e.g., <a href="/wiki/Zearalanone" title="Zearalanone">zearalanone</a>, <a href="/wiki/%CE%91-zearalenol" class="mw-redirect" title="Α-zearalenol">α-zearalenol</a>, <a href="/wiki/%CE%92-zearalenol" class="mw-redirect" title="Β-zearalenol">β-zearalenol</a>, <a href="/wiki/Zearalenone" title="Zearalenone">zearalenone</a>, <a href="/wiki/Zeranol" title="Zeranol">zeranol (α-zearalanol)</a>, <a href="/wiki/Taleranol" title="Taleranol">taleranol (teranol, β-zearalanol)</a>)</li> <li><a href="/wiki/Steroid" title="Steroid">Steroid</a>-like (e.g., <a href="/wiki/Deoxymiroestrol" class="mw-redirect" title="Deoxymiroestrol">deoxymiroestrol</a>, <a href="/wiki/Miroestrol" title="Miroestrol">miroestrol</a>)</li> <li><a href="/wiki/Stilbenoid" title="Stilbenoid">Stilbenoids</a> (e.g., <a href="/wiki/Resveratrol" title="Resveratrol">resveratrol</a>, <a href="/wiki/Rhaponticin" title="Rhaponticin">rhaponticin</a>)</li> <li><a href="/wiki/Synthetic_xenoestrogen" class="mw-redirect" title="Synthetic xenoestrogen">Synthetic xenoestrogens</a> (e.g., <a href="/wiki/Alkylphenol" title="Alkylphenol">alkylphenols</a>, <a href="/wiki/Bisphenol" title="Bisphenol">bisphenols</a> (e.g., <a href="/wiki/Bisphenol_A" title="Bisphenol A">BPA</a>, <a href="/wiki/Bisphenol_F" title="Bisphenol F">BPF</a>, <a href="/wiki/Bisphenol_S" title="Bisphenol S">BPS</a>), <a href="/wiki/Dichlorodiphenyltrichloroethane" class="mw-redirect" title="Dichlorodiphenyltrichloroethane">DDT</a>, <a href="/wiki/Paraben" title="Paraben">parabens</a>, <a href="/wiki/Polybrominated_biphenyl" title="Polybrominated biphenyl">PBBs</a>, <a href="/wiki/4-hydroxybenzoic_acid" class="mw-redirect" title="4-hydroxybenzoic acid">PHBA</a>, <a href="/wiki/Phthalate" class="mw-redirect" title="Phthalate">phthalates</a>, <a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">PCBs</a>)</li> <li>Others (e.g., <a href="/wiki/Agnuside" title="Agnuside">agnuside</a>, <a href="/w/index.php?title=Rotundifuran&action=edit&redlink=1" class="new" title="Rotundifuran (page does not exist)">rotundifuran</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Mixed<br />(<a href="/wiki/Selective_estrogen_receptor_modulators" class="mw-redirect" title="Selective estrogen receptor modulators"><abbr title="Selective estrogen receptor modulators">SERMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Selective estrogen receptor modulators</span>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Phenylbenzofuran" title="2-Phenylbenzofuran">2-Phenylbenzofuran</a></li> <li><a href="/w/index.php?title=2-Phenylbenzothiophene&action=edit&redlink=1" class="new" title="2-Phenylbenzothiophene (page does not exist)">2-Phenylbenzothiophene</a></li> <li><a href="/wiki/4%27-Hydroxynorendoxifen" title="4'-Hydroxynorendoxifen">4'-Hydroxynorendoxifen</a></li> <li><a href="/wiki/27-Hydroxycholesterol" title="27-Hydroxycholesterol">27-Hydroxycholesterol</a></li> <li><a href="/wiki/Acefluranol" title="Acefluranol">Acefluranol</a></li> <li><a href="/wiki/Acolbifene" title="Acolbifene">Acolbifene</a></li> <li><a href="/wiki/Afimoxifene" title="Afimoxifene">Afimoxifene</a></li> <li><a href="/wiki/Anordiol" title="Anordiol">Anordiol</a></li> <li><a href="/wiki/Anordrin" title="Anordrin">Anordrin</a></li> <li><a href="/wiki/Arzoxifene" title="Arzoxifene">Arzoxifene</a></li> <li><a href="/wiki/Bazedoxifene" title="Bazedoxifene">Bazedoxifene</a></li> <li><a href="/wiki/Brilanestrant" title="Brilanestrant">Brilanestrant</a></li> <li><a href="/wiki/Broparestrol" title="Broparestrol">Broparestrol</a></li> <li><a href="/wiki/Camizestrant" title="Camizestrant">Camizestrant</a></li> <li><a href="/wiki/Chlorotrianisene" title="Chlorotrianisene">Chlorotrianisene</a></li> <li><a href="/wiki/Clomifene" title="Clomifene">Clomifene</a></li> <li><a href="/wiki/Clomifenoxide" title="Clomifenoxide">Clomifenoxide</a></li> <li><a href="/w/index.php?title=CN-55945-27&action=edit&redlink=1" class="new" title="CN-55945-27 (page does not exist)">CN-55945-27</a></li> <li><a href="/wiki/Cyclofenil" title="Cyclofenil">Cyclofenil</a></li> <li><a href="/w/index.php?title=D-15413&action=edit&redlink=1" class="new" title="D-15413 (page does not exist)">D-15413</a></li> <li><a href="/wiki/Desmethylchlorotrianisene" title="Desmethylchlorotrianisene">Desmethylchlorotrianisene</a></li> <li><a href="/wiki/Droloxifene" title="Droloxifene">Droloxifene</a></li> <li><a href="/wiki/Enclomifene" title="Enclomifene">Enclomifene</a></li> <li><a href="/wiki/Endoxifen" title="Endoxifen">Endoxifen</a></li> <li><a href="/wiki/Etacstil" title="Etacstil">Etacstil (GW-5638, DPC-974)</a></li> <li><a href="/wiki/Ethamoxytriphetol" title="Ethamoxytriphetol">Ethamoxytriphetol (MER-25)</a></li> <li><a href="/wiki/Femarelle" title="Femarelle">Femarelle</a></li> <li><a href="/wiki/Fispemifene" title="Fispemifene">Fispemifene</a></li> <li><a href="/w/index.php?title=GW-7604&action=edit&redlink=1" class="new" title="GW-7604 (page does not exist)">GW-7604</a></li> <li><a href="/wiki/ICI-55548" class="mw-redirect" title="ICI-55548">ICI-55548</a></li> <li><a href="/wiki/Idoxifene" title="Idoxifene">Idoxifene</a></li> <li><a href="/wiki/Lasofoxifene" title="Lasofoxifene">Lasofoxifene</a></li> <li><a href="/wiki/Levormeloxifene" title="Levormeloxifene">Levormeloxifene</a></li> <li><a href="/wiki/LN-1643" class="mw-redirect" title="LN-1643">LN-1643</a></li> <li><a href="/wiki/LN-2299" class="mw-redirect" title="LN-2299">LN-2299</a></li> <li><a href="/w/index.php?title=LY-117018&action=edit&redlink=1" class="new" title="LY-117018 (page does not exist)">LY-117018</a></li> <li><a href="/wiki/Menerba" title="Menerba">Menerba</a></li> <li><a href="/wiki/Miproxifene" title="Miproxifene">Miproxifene</a></li> <li><a href="/wiki/Miproxifene_phosphate" title="Miproxifene phosphate">Miproxifene phosphate</a></li> <li><a href="/w/index.php?title=MRL-37&action=edit&redlink=1" class="new" title="MRL-37 (page does not exist)">MRL-37</a></li> <li><a href="/wiki/Nafoxidine" title="Nafoxidine">Nafoxidine</a></li> <li><a href="/wiki/Nitromifene" title="Nitromifene">Nitromifene</a></li> <li><a href="/wiki/NNC_45-0095" title="NNC 45-0095">NNC 45-0095</a></li> <li><a href="/w/index.php?title=NNC_45-0320&action=edit&redlink=1" class="new" title="NNC 45-0320 (page does not exist)">NNC 45-0320</a></li> <li><a href="/w/index.php?title=NNC_45-0781&action=edit&redlink=1" class="new" title="NNC 45-0781 (page does not exist)">NNC 45-0781</a></li> <li><a href="/w/index.php?title=NNC_45-1506&action=edit&redlink=1" class="new" title="NNC 45-1506 (page does not exist)">NNC 45-1506</a></li> <li><a href="/wiki/Ormeloxifene" title="Ormeloxifene">Ormeloxifene</a></li> <li><a href="/wiki/Ospemifene" title="Ospemifene">Ospemifene</a></li> <li><a href="/wiki/Panomifene" title="Panomifene">Panomifene</a></li> <li><a href="/wiki/Pipendoxifene" title="Pipendoxifene">Pipendoxifene</a></li> <li><a href="/w/index.php?title=Promensil&action=edit&redlink=1" class="new" title="Promensil (page does not exist)">Promensil</a></li> <li><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></li> <li><a href="/wiki/Rimostil" title="Rimostil">Rimostil (P-081)</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/w/index.php?title=SS1010&action=edit&redlink=1" class="new" title="SS1010 (page does not exist)">SS1010</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a></li> <li><a href="/wiki/TAS-108" title="TAS-108">TAS-108 (SR-16234)</a></li> <li><a href="/wiki/Toremifene" title="Toremifene">Toremifene</a></li> <li><a href="/wiki/Trioxifene" title="Trioxifene">Trioxifene</a></li> <li><a href="/w/index.php?title=TZE-5323&action=edit&redlink=1" class="new" title="TZE-5323 (page does not exist)">TZE-5323</a></li> <li><a href="/w/index.php?title=U-11555A&action=edit&redlink=1" class="new" title="U-11555A (page does not exist)">U-11555A</a></li> <li><a href="/w/index.php?title=U-11634&action=edit&redlink=1" class="new" title="U-11634 (page does not exist)">U-11634</a></li> <li><a href="/w/index.php?title=Y-134&action=edit&redlink=1" class="new" title="Y-134 (page does not exist)">Y-134</a></li> <li><a href="/wiki/Zindoxifene" title="Zindoxifene">Zindoxifene</a></li> <li><a href="/wiki/Zuclomifene" title="Zuclomifene">Zuclomifene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/(R,R)-Tetrahydrochrysene" title="(R,R)-Tetrahydrochrysene">(R,R)-THC</a></li> <li><a href="/wiki/7%CE%B2-Hydroxy-DHEA" title="7β-Hydroxy-DHEA">7β-Hydroxy-DHEA</a></li> <li><a href="/w/index.php?title=Chloroindazole&action=edit&redlink=1" class="new" title="Chloroindazole (page does not exist)">Chloroindazole</a></li> <li><a href="/wiki/Cytestrol_acetate" title="Cytestrol acetate">Cytestrol acetate</a></li> <li><a href="/w/index.php?title=EM-800&action=edit&redlink=1" class="new" title="EM-800 (page does not exist)">EM-800 (SCH-57050)</a></li> <li><a href="/wiki/Epitiostanol" title="Epitiostanol">Epitiostanol</a></li> <li><a href="/w/index.php?title=ERA-90&action=edit&redlink=1" class="new" title="ERA-90 (page does not exist)">ERA-90</a></li> <li><a href="/w/index.php?title=ERB-88&action=edit&redlink=1" class="new" title="ERB-88 (page does not exist)">ERB-88</a></li> <li><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant (ICI-182780)</a></li> <li><a href="/wiki/Glyceollin" title="Glyceollin">Glyceollins</a> (<a href="/wiki/Glyceollin_I" title="Glyceollin I">I</a>, <a href="/w/index.php?title=Glyceollin_II&action=edit&redlink=1" class="new" title="Glyceollin II (page does not exist)">II</a>, <a href="/wiki/Glyceollin_III" title="Glyceollin III">III</a>, <a href="/w/index.php?title=Glyceollin_IV&action=edit&redlink=1" class="new" title="Glyceollin IV (page does not exist)">IV</a>)</li> <li><a href="/wiki/ICI-164384" title="ICI-164384">ICI-164384</a></li> <li><a href="/w/index.php?title=MDL-101906&action=edit&redlink=1" class="new" title="MDL-101906 (page does not exist)">MDL-101906</a></li> <li><a href="/wiki/Mepitiostane" title="Mepitiostane">Mepitiostane</a></li> <li><a href="/wiki/Methylepitiostanol" title="Methylepitiostanol">Methylepitiostanol</a></li> <li><a href="/wiki/Methylpiperidinopyrazole" title="Methylpiperidinopyrazole">Methylpiperidinopyrazole</a></li> <li><a href="/wiki/MIBE" title="MIBE">MIBE</a></li> <li><a href="/w/index.php?title=Oxabicycloheptene_sulfonate&action=edit&redlink=1" class="new" title="Oxabicycloheptene sulfonate (page does not exist)">Oxabicycloheptene sulfonate</a></li> <li><a href="/wiki/Phenytoin" title="Phenytoin">Phenytoin</a></li> <li><a href="/wiki/PHTPP" title="PHTPP">PHTPP</a></li> <li><a href="/wiki/Prochloraz" title="Prochloraz">Prochloraz</a></li> <li><a href="/w/index.php?title=RU-39411&action=edit&redlink=1" class="new" title="RU-39411 (page does not exist)">RU-39411</a></li> <li><a href="/w/index.php?title=RU-58668&action=edit&redlink=1" class="new" title="RU-58668 (page does not exist)">RU-58668</a></li> <li><a href="/w/index.php?title=SS1020&action=edit&redlink=1" class="new" title="SS1020 (page does not exist)">SS1020</a></li> <li><a href="/wiki/TAS-108" title="TAS-108">TAS-108 (SR-16234)</a></li> <li><a href="/wiki/ZB716" title="ZB716">ZB716</a></li> <li><a href="/w/index.php?title=ZK-164015&action=edit&redlink=1" class="new" title="ZK-164015 (page does not exist)">ZK-164015</a></li> <li><a href="/w/index.php?title=ZK-191703&action=edit&redlink=1" class="new" title="ZK-191703 (page does not exist)">ZK-191703</a></li></ul> <ul><li><i>Coregulator-binding modulators:</i> <a href="/wiki/ERX-11" title="ERX-11">ERX-11</a></li></ul> <ul><li><i>Noncompetitive inhibitors:</i> <a href="/wiki/Trilostane" title="Trilostane">Trilostane</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/G_protein-coupled_estrogen_receptor" class="mw-redirect" title="G protein-coupled estrogen receptor"><abbr title="G protein-coupled estrogen receptor">GPER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip G protein-coupled estrogen receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Methoxyestradiol" title="2-Methoxyestradiol">2-Methoxyestradiol</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/Afimoxifene" title="Afimoxifene">Afimoxifene (4-hydroxytamoxifen)</a></li> <li><a href="/wiki/Aldosterone" title="Aldosterone">Aldosterone</a></li> <li><a href="/wiki/Atrazine" title="Atrazine">Atrazine</a></li> <li><a href="/wiki/Bisphenol_A" title="Bisphenol A">Bisphenol A</a></li> <li><a href="/wiki/Daidzein" title="Daidzein">Daidzein</a></li> <li><a href="/wiki/DDT" title="DDT">DDT</a> (<a href="/wiki/P,p%27-DDT" class="mw-redirect" title="P,p'-DDT">p,p'-DDT</a>, <a href="/w/index.php?title=O%27,p%27-DDE&action=edit&redlink=1" class="new" title="O',p'-DDE (page does not exist)">o',p'-DDE</a>)</li> <li><a href="/wiki/Diarylpropionitrile" title="Diarylpropionitrile">Diarylpropionitrile</a></li> <li><a href="/wiki/Equol" title="Equol">Equol</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a></li> <li><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant (ICI-182780)</a></li> <li><a href="/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/Nicotinic_acid" title="Nicotinic acid">Nicotinic acid</a></li> <li><a href="/wiki/Nicotinamide" title="Nicotinamide">Nicotinamide</a></li> <li><a href="/wiki/Nonylphenol" title="Nonylphenol">Nonylphenol</a></li> <li><a href="/wiki/Oleuropein" title="Oleuropein">Oleuropein</a></li> <li><a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">PCBs</a> (<a href="/w/index.php?title=2,2%27,5%27-PCB-4-OH&action=edit&redlink=1" class="new" title="2,2',5'-PCB-4-OH (page does not exist)">2,2',5'-PCB-4-OH</a>)</li> <li><a href="/wiki/Propylpyrazoletriol" title="Propylpyrazoletriol">Propylpyrazoletriol</a></li> <li><a href="/wiki/Quercetin" title="Quercetin">Quercetin</a></li> <li><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></li> <li><a href="/wiki/Resveratrol" title="Resveratrol">Resveratrol</a></li> <li><a href="/w/index.php?title=STX_(drug)&action=edit&redlink=1" class="new" title="STX (drug) (page does not exist)">STX</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a></li> <li><a href="/wiki/Tectoridin" title="Tectoridin">Tectoridin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/CCL18" title="CCL18">CCL18</a></li> <li><a href="/wiki/Estriol" title="Estriol">Estriol</a></li> <li><a href="/w/index.php?title=G-15_(drug)&action=edit&redlink=1" class="new" title="G-15 (drug) (page does not exist)">G-15</a></li> <li><a href="/w/index.php?title=G-36_(drug)&action=edit&redlink=1" class="new" title="G-36 (drug) (page does not exist)">G-36</a></li> <li><a href="/wiki/MIBE" title="MIBE">MIBE</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Unknown</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a></li> <li><a href="/wiki/Zearalenone" title="Zearalenone">Zearalenone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Estrogens_and_antiestrogens" title="Template:Estrogens and antiestrogens">Estrogens and antiestrogens</a></dd> <dd><a href="/wiki/Template:Androgen_receptor_modulators" title="Template:Androgen receptor modulators">Androgen receptor modulators</a></dd> <dd><a href="/wiki/Template:Progesterone_receptor_modulators" title="Template:Progesterone receptor modulators">Progesterone receptor modulators</a></dd> <dd><a href="/wiki/List_of_steroidal_estrogens" class="mw-redirect" title="List of steroidal estrogens">List of estrogens</a></dd></dl> </div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" alt="" 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