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vector-toc-level-1"> <a class="vector-toc-link" href="#Contraindications"> <div class="vector-toc-text"> 2 Contraindications </div> </a> <ul id="toc-Contraindications-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Side_effects" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Side_effects"> <div class="vector-toc-text"> 3 Side effects </div> </a> <ul id="toc-Side_effects-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Overdose" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Overdose"> <div class="vector-toc-text"> 4 Overdose </div> </a> <ul id="toc-Overdose-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Interactions" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Interactions"> <div class="vector-toc-text"> 5 Interactions </div> </a> <ul id="toc-Interactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pharmacology" 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</nav> <h1 id="firstHeading" class="firstHeading mw-first-heading">Dydrogesterone</h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. 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hreflang="azb" data-title="دیدروژسترون" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target">تۆرکجه</a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%AF%DB%8C%D8%AF%D8%B1%D9%88%DA%98%D8%B3%D8%AA%D8%B1%D9%88%D9%86" title="دیدروژسترون – Persian" lang="fa" hreflang="fa" data-title="دیدروژسترون" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target">فارسی</a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%94%D0%B8%D0%B4%D1%80%D0%BE%D0%B3%D0%B5%D1%81%D1%82%D0%B5%D1%80%D0%BE%D0%BD" title="Дидрогестерон – Russian" lang="ru" hreflang="ru" data-title="Дидрогестерон" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target">Русский</a></li><li class="interlanguage-link interwiki-ckb mw-list-item"><a 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searchaux" style="display:none">Chemical compound</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Retroprogesterone" title="Retroprogesterone">Retroprogesterone</a>.</div> <div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Pharmaceutical compound</div> <style data-mw-deduplicate="TemplateStyles:r1269284339">@media screen{html.skin-theme-clientpref-night .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}</style> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title">Dydrogesterone</caption><tbody><tr><td colspan="2" class="infobox-image"><a href="/wiki/File:Dydrogesterone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/27/Dydrogesterone.svg/225px-Dydrogesterone.svg.png" decoding="async" width="225" height="166" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/27/Dydrogesterone.svg/338px-Dydrogesterone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/27/Dydrogesterone.svg/450px-Dydrogesterone.svg.png 2x" data-file-width="512" data-file-height="377" /></a></td></tr><tr><td colspan="2" class="infobox-image"><a href="/wiki/File:Dydrogesterone_molecule_ball.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/32/Dydrogesterone_molecule_ball.png/235px-Dydrogesterone_molecule_ball.png" decoding="async" width="235" height="197" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/32/Dydrogesterone_molecule_ball.png/353px-Dydrogesterone_molecule_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/32/Dydrogesterone_molecule_ball.png/470px-Dydrogesterone_molecule_ball.png 2x" data-file-width="2320" data-file-height="1943" /></a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Duphaston, others<a href="#cite_note-brands-1">[1]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">Isopregnenone; Dehydroprogesterone; Didrogesteron; 6-Dehydroretroprogesterone; 9β,10α-Pregna-4,6-diene-3,20-dione; NSC-92336<a href="#cite_note-Elks2014-2">[2]</a><a href="#cite_note-IndexNominum2000-3">[3]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/American_Society_of_Health-System_Pharmacists" title="American Society of Health-System Pharmacists">AHFS</a>/<a href="/wiki/Drugs.com" title="Drugs.com">Drugs.com</a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://www.drugs.com/international/dydrogesterone.html">International Drug Names</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of administration</a></th><td class="infobox-data"><a href="/wiki/Oral_administration" title="Oral administration">By mouth</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_class" title="Drug class">Drug class</a></th><td class="infobox-data"><a href="/wiki/Progestogen_(medication)" title="Progestogen (medication)">Progestogen</a>; <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">Progestin</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><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><a href="/wiki/ATC_code_G03" title="ATC code G03">G03DB01</a> (<a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=G03DB01">WHO</a>) </li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"> <ul><li>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/Bioavailability" title="Bioavailability">Bioavailability</a></th><td class="infobox-data">28%<a href="#cite_note-Femoston-Label-4">[4]</a><a href="#cite_note-Schindler2015-5">[5]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">Protein binding</a></th><td class="infobox-data">? (probably to <a href="/wiki/Human_serum_albumin" title="Human serum albumin">albumin</a>)<a href="#cite_note-FRCOG2015-6">[6]</a><a href="#cite_note-pmid16112947-7">[7]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_metabolism" title="Drug metabolism">Metabolism</a></th><td class="infobox-data"><a href="/wiki/Liver" title="Liver">Hepatic</a>: <a href="/wiki/AKR1C1" title="AKR1C1">AKR1C1</a>, <a href="/wiki/AKR1C3" title="AKR1C3">AKR1C3</a>, <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a><a href="#cite_note-OlbrichWeigl2016-10">[10]</a><a href="#cite_note-BeraničGobec2011-8">[8]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Metabolite" title="Metabolite">Metabolites</a></th><td class="infobox-data"><a href="/wiki/20%CE%B1-Dihydrodydrogesterone" title="20α-Dihydrodydrogesterone"><abbr title="20α-Dihydrodydrogesterone">20α-DHD</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 20α-Dihydrodydrogesterone (exclusively via AKR1C1 and AKRC13)<a href="#cite_note-BeraničGobec2011-8">[8]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Biological_half-life" title="Biological half-life">Elimination half-life</a></th><td class="infobox-data"><abbr title="Dydrogesterone">Parent</abbr>: 5–7 hours<a href="#cite_note-BińkowskaWoroń2015-9">[9]</a> <abbr title="20α-Dihydrodydrogesterone">Metabolite</abbr>: 14–17 hours<a href="#cite_note-BińkowskaWoroń2015-9">[9]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Excretion" title="Excretion">Excretion</a></th><td class="infobox-data"><a href="/wiki/Urine" title="Urine">Urine</a></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%;">(8S,9R,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one</div></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=152-62-5">152-62-5</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/9051">9051</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB00378">DB00378</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.8699.html">8699</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/90I02KLE8K">90I02KLE8K</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/KEGG" title="KEGG">KEGG</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D01217">D01217</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:31527">CHEBI:31527</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> (<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID1022974">DTXSID1022974</a> <a href="https://www.wikidata.org/wiki/Q4161380#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard">ECHA InfoCard</a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.005.280">100.005.280</a> <a href="https://www.wikidata.org/wiki/Q4161380#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data">C21H28O2</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data">312.453 g·mol−1</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC4%5CC%3DC3%5CC%3DC%2F%5BC%40%40H%5D1%5BC%40%40H%5D%28CC%5BC%40%40%5D2%28%5BC%40%40H%5D%28C%28%3DO%29C%29CC%5BC%40%40H%5D12%29C%29%5BC%40%5D3%28C%29CC4">Interactive image</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Melting_point" title="Melting point">Melting point</a></th><td class="infobox-data">144 °C (291 °F)</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a></th><td class="infobox-data">463 °C (865 °F)</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></th><td class="infobox-data">Insoluble mg/mL (20 °C)</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=C4\C=C3\C=C/[C@@H]1[C@@H](CC[C@@]2([C@@H](C(=O)C)CC[C@@H]12)C)[C@]3(C)CC4</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">InChI=1S/C21H28O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4-5,12,16-19H,6-11H2,1-3H3/t16-,17+,18-,19+,20+,21+/m0/s1 <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</div></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:JGMOKGBVKVMRFX-HQZYFCCVSA-N <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-below"><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style>  <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=461091780&page2=Dydrogesterone">(verify)</a></td></tr></tbody></table> Dydrogesterone, sold under the brand name Duphaston among others,<a href="#cite_note-brands-1">[1]</a> is a <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestin</a> <a href="/wiki/Drug" title="Drug">medication</a> which is used for a variety of indications, including <a href="/wiki/Miscarriage" title="Miscarriage">threatened</a> or <a href="/wiki/Recurrent_miscarriage" title="Recurrent miscarriage">recurrent miscarriage</a> during <a href="/wiki/Pregnancy" title="Pregnancy">pregnancy</a>, <a href="/wiki/Dysfunctional_bleeding" class="mw-redirect" title="Dysfunctional bleeding">dysfunctional bleeding</a>, <a href="/wiki/Infertility" title="Infertility">infertility</a> due to <a href="/wiki/Luteal_insufficiency" class="mw-redirect" title="Luteal insufficiency">luteal insufficiency</a>, <a href="/wiki/Dysmenorrhea" title="Dysmenorrhea">dysmenorrhea</a>, <a href="/wiki/Endometriosis" title="Endometriosis">endometriosis</a>, secondary <a href="/wiki/Amenorrhea" title="Amenorrhea">amenorrhea</a>, <a href="/wiki/Irregular_menstruation" title="Irregular menstruation">irregular cycles</a>, <a href="/wiki/Premenstrual_syndrome" title="Premenstrual syndrome">premenstrual syndrome</a>, and as a component of <a href="/wiki/Menopausal_hormone_therapy" class="mw-redirect" title="Menopausal hormone therapy">menopausal hormone therapy</a>.<a href="#cite_note-pmid16112947-7">[7]</a> It is taken <a href="/wiki/Oral_administration" title="Oral administration">by mouth</a>.<a href="#cite_note-pmid16112947-7">[7]</a> <a href="/wiki/Side_effect" title="Side effect">Side effects</a> of dydrogesterone include <a href="/wiki/Menstrual_irregularities" class="mw-redirect" title="Menstrual irregularities">menstrual irregularities</a>, <a href="/wiki/Headache" title="Headache">headache</a>, <a href="/wiki/Nausea" title="Nausea">nausea</a>, <a href="/wiki/Breast_tenderness" class="mw-redirect" title="Breast tenderness">breast tenderness</a>, and others.<a href="#cite_note-MishellKirschbaum1990-11">[11]</a><a href="#cite_note-Femoston-NHS-12">[12]</a> Dydrogesterone is a progestin, or a <a href="/wiki/Synthetic_compound" class="mw-redirect" title="Synthetic compound">synthetic</a> <a href="/wiki/Progestogen_(medication)" title="Progestogen (medication)">progestogen</a>, and hence is an <a href="/wiki/Agonist" title="Agonist">agonist</a> of the <a href="/wiki/Progesterone_receptor" title="Progesterone receptor">progesterone receptor</a>, the <a href="/wiki/Biological_target" title="Biological target">biological target</a> of progestogens like <a href="/wiki/Progesterone" title="Progesterone">progesterone</a>.<a href="#cite_note-pmid16112947-7">[7]</a><a href="#cite_note-Schindler2009-13">[13]</a> The medication is an atypical progestogen and does not inhibit <a href="/wiki/Ovulation" title="Ovulation">ovulation</a>.<a href="#cite_note-pmid16112947-7">[7]</a><a href="#cite_note-Tausk1972-14">[14]</a> It has weak <a href="/wiki/Antimineralocorticoid" class="mw-redirect" title="Antimineralocorticoid">antimineralocorticoid</a> activity and no other important <a href="/wiki/Hormonal_agent" class="mw-redirect" title="Hormonal agent">hormonal</a> activity.<a href="#cite_note-pmid16112947-7">[7]</a><a href="#cite_note-Schindler2009-13">[13]</a> Dydrogesterone was developed in the 1950s and introduced for medical use in 1961.<a href="#cite_note-Publishing2013-15">[15]</a> It is available widely throughout <a href="/wiki/Europe" title="Europe">Europe</a>, no longer available in the <a href="/wiki/United_Kingdom" title="United Kingdom">United Kingdom</a>, since 2008 and is also marketed in <a href="/wiki/Australia" title="Australia">Australia</a> and elsewhere in the world.<a href="#cite_note-IndexNominum2000-3">[3]</a><a href="#cite_note-Publishing2013-15">[15]</a> The medication was previously available in the <a href="/wiki/United_States" title="United States">United States</a>,<a href="#cite_note-Publishing2013-15">[15]</a> but it has been discontinued in that country.<a href="#cite_note-Manu2000-16">[16]</a> <style data-mw-deduplicate="TemplateStyles:r886046785">.mw-parser-output .toclimit-2 .toclevel-1 ul,.mw-parser-output .toclimit-3 .toclevel-2 ul,.mw-parser-output .toclimit-4 .toclevel-3 ul,.mw-parser-output .toclimit-5 .toclevel-4 ul,.mw-parser-output .toclimit-6 .toclevel-5 ul,.mw-parser-output .toclimit-7 .toclevel-6 ul{display:none}</style><div class="toclimit-3"><meta property="mw:PageProp/toc" /></div> <div class="mw-heading mw-heading2"><h2 id="Medical_uses">Medical uses</h2>[<a href="/w/index.php?title=Dydrogesterone&action=edit&section=1" title="Edit section: Medical uses">edit</a>]</div> Dydrogesterone has proven effective in a variety of conditions associated with progesterone deficiency,<a href="#cite_note-pmid14667985-17">[17]</a> <a href="/wiki/Infertility" title="Infertility">Infertility</a> due to <a href="/wiki/Luteal_insufficiency" class="mw-redirect" title="Luteal insufficiency">luteal insufficiency</a><a href="#cite_note-18">[18]</a><a href="#cite_note-19">[19]</a> including threatened <a href="/wiki/Miscarriage" title="Miscarriage">miscarriage</a>,<a href="#cite_note-pmid20005647-20">[20]</a> habitual or recurrent miscarriage,<a href="#cite_note-:0-21">[21]</a> <a href="/wiki/Menstruation" title="Menstruation">Menstrual</a> disorders<a href="#cite_note-22">[22]</a> premenstrual syndrome,<a href="#cite_note-ReferenceA-23">[23]</a> and endometriosis.<a href="#cite_note-24">[24]</a> Dydrogesterone has also been registered as a component of <a href="/wiki/Menopausal_hormone_therapy" class="mw-redirect" title="Menopausal hormone therapy">menopausal hormone therapy</a><a href="#cite_note-25">[25]</a> to counteract the effects of unopposed <a href="/wiki/Estrogen" title="Estrogen">estrogen</a> on the endometrium in persons with an intact uterus. <div class="mw-heading mw-heading3"><h3 id="Gynecological_disorders">Gynecological disorders</h3>[<a href="/w/index.php?title=Dydrogesterone&action=edit&section=2" title="Edit section: Gynecological disorders">edit</a>]</div> Primary or essential dysmenorrhea is a very common gynecological phenomenon experienced by women during their reproductive years. Clinical studies have shown symptom relief and a reduction in pain with dydrogesterone treatment for dysmenorrhea.<a href="#cite_note-pmid17943543-26">[26]</a> Secondary amenorrhea is not a specific disease, but is instead a symptom. Dydrogesterone has been found to adequately induce bleeding within a sufficiently estrogen-primed endometrium. When <a href="/wiki/Estradiol" title="Estradiol">estradiol</a> levels are found to be low, dydrogesterone treatment is more effective when supplemented with <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogens</a>.<a href="#cite_note-27">[27]</a> Endometriosis is a chronic disease which can cause severe, progressive, and at times, incapacitating dysmenorrhea, <a href="/wiki/Pelvic_pain" title="Pelvic pain">pelvic pain</a>, <a href="/wiki/Dyspareunia" title="Dyspareunia">dyspareunia</a> and <a href="/wiki/Infertility" title="Infertility">infertility</a>. Dydrogesterone relieves pain without inhibiting ovulation, so that patients are able to become pregnant during treatment. Dydrogesterone is particularly suitable in cases where the woman desires to become pregnant and to prevent bleeding problems.<a href="#cite_note-pmid19945806-28">[28]</a> Dydrogesterone results in statistically significant reductions in the symptoms pelvic pain, dysmenorrhea and dyspareunia after the first treatment cycle for the treatment of post-laparoscopic <a href="/wiki/Endometriosis_and_infertility" title="Endometriosis and infertility">endometriosis</a>.<a href="#cite_note-pmid17943543-26">[26]</a> The amount and duration of menstrual bleeding is also significantly reduced, and from the end of the third month onwards, bleeding was considered normal in the majority of patients. Improvement of endometriosis was observed in 71% of patients. Dydrogesterone has shown reasonable efficacy in relieving a number of premenstrual syndrome symptoms like <a href="/wiki/Mood_swing" title="Mood swing">mood swings</a> and physical symptoms.<a href="#cite_note-ReferenceA-23">[23]</a> Cyclic treatment with low-dose (10 mg/day) dydrogesterone has been found to be effective in the treatment of <a href="/wiki/Fibrocystic_breast_changes" title="Fibrocystic breast changes">fibrocystic breast changes</a> and associated <a href="/wiki/Mastodynia" class="mw-redirect" title="Mastodynia">breast pain</a>.<a href="#cite_note-pmid12227885-29">[29]</a> <div class="mw-heading mw-heading3"><h3 id="Infertility_and_miscarriage">Infertility and miscarriage</h3>[<a href="/w/index.php?title=Dydrogesterone&action=edit&section=3" title="Edit section: Infertility and miscarriage">edit</a>]</div> Oral dydrogesterone is an effective medication, well tolerated and accepted among patients, and can be considered for routine <a href="/wiki/Luteal_support" title="Luteal support">luteal support</a>. Advantage of dydrogesterone is oral administration, easy to use and better patient <a href="/wiki/Compliance_(medicine)" class="mw-redirect" title="Compliance (medicine)">compliance</a> which results in high satisfaction score of oral dydrogesterone in luteal support of <a href="/wiki/In_vitro_fertilisation" title="In vitro fertilisation">IVF</a>/<a href="/wiki/Intracytoplasmic_sperm_injection" title="Intracytoplasmic sperm injection">ICSI</a> cycles.<a href="#cite_note-pmid25622239-30">[30]</a> Oral administration of progestins dydrogesterone at least similar <a href="/wiki/Live_birth_rate" class="mw-redirect" title="Live birth rate">live birth rate</a> than vaginal progesterone capsules when used for luteal support in <a href="/wiki/Embryo_transfer" title="Embryo transfer">embryo transfer</a>, with no evidence of increased risk of <a href="/wiki/Miscarriage" title="Miscarriage">miscarriage</a>.<a href="#cite_note-BarbosaValadares2018-31">[31]</a><a href="#cite_note-GriesingerBlockeel2018-32">[32]</a> Threatened <a href="/wiki/Miscarriage" title="Miscarriage">miscarriage</a> is defined as bleeding during the first 20 weeks of pregnancy while the cervix is closed. It is the most common complication in pregnancy, occurring in 20% of all pregnancies. <a href="/wiki/Recurrent_miscarriage" title="Recurrent miscarriage">Recurrent abortion</a> is defined as the loss of three or more consecutive pregnancies. Dydrogesterone is associated with approximately two-fold significant reduction in the miscarriage rate as compared to standard care in threatened and recurrent miscarriages with minimal side effects.<a href="#cite_note-:0-21">[21]</a><a href="#cite_note-pmid22794306-33">[33]</a> <div class="mw-heading mw-heading3"><h3 id="Hormone_therapy">Hormone therapy</h3>[<a href="/w/index.php?title=Dydrogesterone&action=edit&section=4" title="Edit section: Hormone therapy">edit</a>]</div> The objective behind <a href="/wiki/Menopausal_hormone_therapy" class="mw-redirect" title="Menopausal hormone therapy">menopausal hormone therapy</a> is to actively increase the circulating levels of estrogen to control <a href="/wiki/Hot_flash" title="Hot flash">hot flashes</a> and to prevent the long-term effects of the <a href="/wiki/Menopause" title="Menopause">menopause</a>, such as <a href="/wiki/Bone_resorption" title="Bone resorption">bone resorption</a> and unfavourable changes in <a href="/wiki/Blood_lipids" title="Blood lipids">blood lipids</a>. The administration of <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a> halts, or reverses <a href="/wiki/Atrophy" title="Atrophy">atrophic</a> changes that occur due to the loss of endogenous estradiol during the menopause.<a href="#cite_note-34">[34]</a> Estrogen promotes endometrial cell growth and in <a href="/wiki/Menopause#Postmenopause" title="Menopause">postmenopausal</a> women with an intact uterus, estrogen <a href="/wiki/Combination_therapy" title="Combination therapy">monotherapy</a> results in continued endometrial development without the physiological secretory changes normally brought on by progesterone. This action is associated with an increased incidence of endometrial <a href="/wiki/Hyperplasia" title="Hyperplasia">hyperplasia</a> and <a href="/wiki/Carcinoma" title="Carcinoma">carcinoma</a>. Additional protection with progestogens is therefore important in patients with an intact uterus who receive estrogen therapy. Dydrogesterone counters the <a href="/wiki/Cell_growth" title="Cell growth">proliferative</a> effect of estrogens on the endometrium and ensures the transition to a secretory pattern and cyclical shedding of the endometrium in serial menopausal hormone therapy regimes. Dydrogesterone effectively protects against the <a href="/wiki/Ontogeny" title="Ontogeny">ontogenesis</a> of endometrial hyperplasia. Unlike androgenic progestogens, dydrogesterone does not reverse the benefits brought on by estradiol on lipid profiles and carbohydrate metabolism. In a continuous, combined menopausal hormone therapy regimen, dydrogesterone retards the proliferation of the endometrium so that it remains atrophic or inactive.<a href="#cite_note-35">[35]</a> <div class="mw-heading mw-heading3"><h3 id="Available_forms">Available forms</h3>[<a href="/w/index.php?title=Dydrogesterone&action=edit&section=5" title="Edit section: Available forms">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Estradiol/dydrogesterone" title="Estradiol/dydrogesterone">Estradiol/dydrogesterone</a></div> Dydrogesterone is available in the form of 10 mg <a href="/wiki/Oral_administration" title="Oral administration">oral</a> <a href="/wiki/Tablet_(pharmacy)" title="Tablet (pharmacy)">tablets</a> both alone and in combination with <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a>.<a href="#cite_note-Muller1998-36">[36]</a><a href="#cite_note-ChyeTeng2014-37">[37]</a> <div class="mw-heading mw-heading2"><h2 id="Contraindications">Contraindications</h2>[<a href="/w/index.php?title=Dydrogesterone&action=edit&section=6" title="Edit section: Contraindications">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Progestin#Contraindications" class="mw-redirect" title="Progestin">Progestin § Contraindications</a></div> <div class="mw-heading mw-heading2"><h2 id="Side_effects">Side effects</h2>[<a href="/w/index.php?title=Dydrogesterone&action=edit&section=7" title="Edit section: Side effects">edit</a>]</div> The most commonly reported medication-related adverse reactions in people taking dydrogesterone without an estrogen in clinical trials of indications have included <a href="/wiki/Menstrual_irregularities" class="mw-redirect" title="Menstrual irregularities">menstrual irregularities</a>, <a href="/wiki/Headaches" class="mw-redirect" title="Headaches">headaches</a>, <a href="/wiki/Migraine" title="Migraine">migraines</a>, <a href="/wiki/Nausea" title="Nausea">nausea</a>, <a href="/wiki/Breast_tenderness" class="mw-redirect" title="Breast tenderness">breast tenderness</a>, <a href="/wiki/Bloating" title="Bloating">bloating</a>, and <a href="/wiki/Weight_gain" title="Weight gain">weight gain</a>.<a href="#cite_note-MishellKirschbaum1990-11">[11]</a><a href="#cite_note-Femoston-NHS-12">[12]</a> The use of progestins, in particular <a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">medroxyprogesterone acetate</a>, in treating postmenopausal symptoms have been associated with increased risk of <a href="/wiki/Thrombus" title="Thrombus">blood clots</a><a href="#cite_note-38">[38]</a> and <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a> in a study carried out by the <a href="/wiki/Women%27s_Health_Initiative" title="Women's Health Initiative">Women's Health Initiative</a>. While the study did not involve dydrogesterone, it is possible, but not certain, that it too increases these risks.<a href="#cite_note-39">[39]</a> Dydrogesterone has been <a href="/wiki/Medical_prescription" title="Medical prescription">prescribed</a> and used in over 10 million pregnancies worldwide. There have been no harmful effects exhibited due to the use of dydrogesterone while pregnant. Dydrogesterone is safe to use during pregnancy only when prescribed and indicated by a <a href="/wiki/Health_professional" title="Health professional">medical practitioner</a>.<a href="#cite_note-DYDROBOON_10mg_Film-Coated_Tablets-40">[40]</a> Studies have not shown any incidence of decreased fertility due to dydrogesterone at therapeutic dose.<a href="#cite_note-DYDROBOON_10mg_Film-Coated_Tablets-40">[40]</a> The <a href="/wiki/Ames_test" title="Ames test">Ames test</a> found no evidence of any potential <a href="/wiki/Mutagen" title="Mutagen">mutagenic</a> or toxicity properties.<a href="#cite_note-41">[41]</a> <table class="wikitable sortable mw-collapsible mw-collapsed" style="margin: 1em auto;"> <caption class="nowrap"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul ul{display:inline}.mw-parser-output .hlist .mw-empty-li{display:none}.mw-parser-output .hlist dt::after{content:": "}.mw-parser-output .hlist dd::after,.mw-parser-output .hlist li::after{content:" · ";font-weight:bold}.mw-parser-output .hlist dd:last-child::after,.mw-parser-output .hlist dt:last-child::after,.mw-parser-output .hlist li:last-child::after{content:none}.mw-parser-output .hlist dd dd:first-child::before,.mw-parser-output .hlist dd dt:first-child::before,.mw-parser-output .hlist dd li:first-child::before,.mw-parser-output .hlist dt dd:first-child::before,.mw-parser-output .hlist dt dt:first-child::before,.mw-parser-output .hlist dt li:first-child::before,.mw-parser-output .hlist li dd:first-child::before,.mw-parser-output .hlist li dt:first-child::before,.mw-parser-output .hlist li li:first-child::before{content:" (";font-weight:normal}.mw-parser-output .hlist dd dd:last-child::after,.mw-parser-output .hlist dd dt:last-child::after,.mw-parser-output .hlist dd li:last-child::after,.mw-parser-output .hlist dt dd:last-child::after,.mw-parser-output .hlist dt dt:last-child::after,.mw-parser-output .hlist dt li:last-child::after,.mw-parser-output .hlist li dd:last-child::after,.mw-parser-output .hlist li dt:last-child::after,.mw-parser-output .hlist li li:last-child::after{content:")";font-weight:normal}.mw-parser-output .hlist ol{counter-reset:listitem}.mw-parser-output .hlist ol>li{counter-increment:listitem}.mw-parser-output .hlist ol>li::before{content:" "counter(listitem)"\a0 "}.mw-parser-output .hlist dd ol>li:first-child::before,.mw-parser-output .hlist dt ol>li:first-child::before,.mw-parser-output .hlist li ol>li:first-child::before{content:" ("counter(listitem)"\a0 "}</style><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Risk_of_breast_cancer_with_menopausal_hormone_therapy_in_large_observational_studies" title="Template:Risk of breast cancer with menopausal hormone therapy in large observational studies"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Risk_of_breast_cancer_with_menopausal_hormone_therapy_in_large_observational_studies" title="Template talk:Risk of breast cancer with menopausal hormone therapy in large observational studies"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Risk_of_breast_cancer_with_menopausal_hormone_therapy_in_large_observational_studies" title="Special:EditPage/Template:Risk of breast cancer with menopausal hormone therapy in large observational studies"><abbr title="Edit this template">e</abbr></a></li></ul></div> Risk of breast cancer with menopausal hormone therapy in large observational studies (Mirkin, 2018) </caption> <tbody><tr> <th class="unsortable">Study</th> <th class="unsortable">Therapy</th> <th class="unsortable"><a href="/wiki/Hazard_ratio" title="Hazard ratio">Hazard ratio</a> (95% <a href="/wiki/Confidence_interval" title="Confidence interval"><abbr title="confidence interval">CI</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 confidence interval) </th></tr> <tr> <td rowspan="3">E3N-EPIC: Fournier et al. (2005)</td> <td>Estrogen alone</td> <td>1.1 (0.8–1.6) </td></tr> <tr> <td>Estrogen plus <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a>     Transdermal estrogen     Oral estrogen</td> <td>0.9 (0.7–1.2) 0.9 (0.7–1.2) No events </td></tr> <tr> <td>Estrogen plus progestin     Transdermal estrogen     Oral estrogen</td> <td>1.4 (1.2–1.7) 1.4 (1.2–1.7) 1.5 (1.1–1.9) </td></tr> <tr> <td rowspan="4">E3N-EPIC: Fournier et al. (2008)</td> <td>Oral estrogen alone</td> <td>1.32 (0.76–2.29) </td></tr> <tr> <td>Oral estrogen plus progestogen     <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">Progesterone</a>     Dydrogesterone     <a href="/wiki/Medrogestone" title="Medrogestone">Medrogestone</a>     <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/Promegestone" title="Promegestone">Promegestone</a>     <a href="/wiki/Nomegestrol_acetate" title="Nomegestrol acetate">Nomegestrol acetate</a>     <a href="/wiki/Norethisterone_acetate" title="Norethisterone acetate">Norethisterone acetate</a>     <a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">Medroxyprogesterone acetate</a></td> <td> Not analyzeda 0.77 (0.36–1.62) 2.74 (1.42–5.29) 2.02 (1.00–4.06) 2.57 (1.81–3.65) 1.62 (0.94–2.82) 1.10 (0.55–2.21) 2.11 (1.56–2.86) 1.48 (1.02–2.16) </td></tr> <tr> <td>Transdermal estrogen alone</td> <td>1.28 (0.98–1.69) </td></tr> <tr> <td>Transdermal estrogen plus progestogen     <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">Progesterone</a>     Dydrogesterone     <a href="/wiki/Medrogestone" title="Medrogestone">Medrogestone</a>     <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/Promegestone" title="Promegestone">Promegestone</a>     <a href="/wiki/Nomegestrol_acetate" title="Nomegestrol acetate">Nomegestrol acetate</a>     <a href="/wiki/Norethisterone_acetate" title="Norethisterone acetate">Norethisterone acetate</a>     <a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">Medroxyprogesterone acetate</a></td> <td> 1.08 (0.89–1.31) 1.18 (0.95–1.48) 2.03 (1.39–2.97) 1.48 (1.05–2.09) Not analyzeda 1.52 (1.19–1.96) 1.60 (1.28–2.01) Not analyzeda Not analyzeda </td></tr> <tr> <td rowspan="3">E3N-EPIC: Fournier et al. (2014)</td> <td>Estrogen alone</td> <td>1.17 (0.99–1.38) </td></tr> <tr> <td>Estrogen plus <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a> or dydrogesterone</td> <td>1.22 (1.11–1.35) </td></tr> <tr> <td>Estrogen plus progestin</td> <td>1.87 (1.71–2.04) </td></tr> <tr> <td rowspan="2">CECILE: Cordina-Duverger et al. (2013)</td> <td>Estrogen alone</td> <td>1.19 (0.69–2.04) </td></tr> <tr> <td>Estrogen plus progestogen     <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">Progesterone</a>     Progestins         Progesterone derivatives         Testosterone derivatives</td> <td>1.33 (0.92–1.92) 0.80 (0.44–1.43) 1.72 (1.11–2.65) 1.57 (0.99–2.49) 3.35 (1.07–10.4) </td></tr> <tr class="sortbottom"> <td colspan="3" style="width: 1px; background-color:#eaecf0; text-align: center;">Footnotes: a = Not analyzed, fewer than 5 cases. Sources: See template. </td></tr></tbody></table> <table class="wikitable sortable mw-collapsible mw-collapsed" style="margin: 1em auto;"> <caption class="nowrap"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Risk_of_breast_cancer_with_menopausal_hormone_therapy_by_duration_in_large_observational_studies" title="Template:Risk of breast cancer with menopausal hormone therapy by duration in large observational studies"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Risk_of_breast_cancer_with_menopausal_hormone_therapy_by_duration_in_large_observational_studies" title="Template talk:Risk of breast cancer with menopausal hormone therapy by duration in large observational studies"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Risk_of_breast_cancer_with_menopausal_hormone_therapy_by_duration_in_large_observational_studies" title="Special:EditPage/Template:Risk of breast cancer with menopausal hormone therapy by duration in large observational studies"><abbr title="Edit this template">e</abbr></a></li></ul></div> Risk of breast cancer with menopausal hormone therapy by duration in large observational studies (Mirkin, 2018) </caption> <tbody><tr> <th class="unsortable">Study</th> <th class="unsortable">Therapy</th> <th class="unsortable"><a href="/wiki/Hazard_ratio" title="Hazard ratio">Hazard ratio</a> (95% <a href="/wiki/Confidence_interval" title="Confidence interval"><abbr title="confidence interval">CI</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 confidence interval) </th></tr> <tr> <td rowspan="3">E3N-EPIC: Fournier et al. (2005)a</td> <td>Transdermal estrogen plus <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a>     <2 years     2–4 years     ≥4 years</td> <td> 0.9 (0.6–1.4) 0.7 (0.4–1.2) 1.2 (0.7–2.0) </td></tr> <tr> <td>Transdermal estrogen plus progestin     <2 years     2–4 years     ≥4 years</td> <td> 1.6 (1.3–2.0) 1.4 (1.0–1.8) 1.2 (0.8–1.7) </td></tr> <tr> <td>Oral estrogen plus progestin     <2 years     2–4 years     ≥4 years</td> <td> 1.2 (0.9–1.8) 1.6 (1.1–2.3) 1.9 (1.2–3.2) </td></tr> <tr> <td rowspan="3">E3N-EPIC: Fournier et al. (2008)</td> <td>Estrogen plus <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a>     <2 years     2–4 years     4–6 years     ≥6 years</td> <td> 0.71 (0.44–1.14) 0.95 (0.67–1.36) 1.26 (0.87–1.82) 1.22 (0.89–1.67) </td></tr> <tr> <td>Estrogen plus dydrogesterone     <2 years     2–4 years     4–6 years     ≥6 years</td> <td> 0.84 (0.51–1.38) 1.16 (0.79–1.71) 1.28 (0.83–1.99) 1.32 (0.93–1.86) </td></tr> <tr> <td>Estrogen plus other progestogens     <2 years     2–4 years     4–6 years     ≥6 years</td> <td> 1.36 (1.07–1.72) 1.59 (1.30–1.94) 1.79 (1.44–2.23) 1.95 (1.62–2.35) </td></tr> <tr> <td rowspan="2">E3N-EPIC: Fournier et al. (2014)</td> <td>Estrogens plus <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a> or dydrogesterone     <5 years     ≥5 years</td> <td> 1.13 (0.99–1.29) 1.31 (1.15–1.48) </td></tr> <tr> <td>Estrogen plus other progestogens     <5 years     ≥5 years</td> <td> 1.70 (1.50–1.91) 2.02 (1.81–2.26) </td></tr> <tr class="sortbottom"> <td colspan="3" style="width: 1px; background-color:#eaecf0; text-align: center;">Footnotes: a = Oral estrogen plus progesterone was not analyzed because there was a low number of women who used this therapy. Sources: See template. </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Overdose">Overdose</h2>[<a href="/w/index.php?title=Dydrogesterone&action=edit&section=8" title="Edit section: Overdose">edit</a>]</div> There is not enough clinical data to support <a href="/wiki/Overdose" class="mw-redirect" title="Overdose">overdose</a> in humans. The maximum dose of dydrogesterone administered to humans to date was 360 mg orally, and the medication was found to be well tolerated at this dose.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] There are no <a href="/wiki/Antidote" title="Antidote">antidotes</a> to overdose, and treatment should be based on <a href="/wiki/Symptom" class="mw-redirect" title="Symptom">symptoms</a>.<a href="#cite_note-DYDROBOON_10mg_Film-Coated_Tablets-40">[40]</a> In acute toxicity trials, the LD50 doses in rats were in excess of 4,640 mg/kg orally.<a href="#cite_note-DrugBank-42">[42]</a><a href="#cite_note-43">[43]</a> <div class="mw-heading mw-heading2"><h2 id="Interactions">Interactions</h2>[<a href="/w/index.php?title=Dydrogesterone&action=edit&section=9" title="Edit section: Interactions">edit</a>]</div> In menopausal hormone therapy, dydrogesterone is administered together with an estrogen. Therefore, the interaction between dydrogesterone and estrogens has been assessed, and no clinically significant interaction has been observed.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2>[<a href="/w/index.php?title=Dydrogesterone&action=edit&section=10" title="Edit section: Pharmacology">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Pharmacodynamics">Pharmacodynamics</h3>[<a href="/w/index.php?title=Dydrogesterone&action=edit&section=11" title="Edit section: Pharmacodynamics">edit</a>]</div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:20%CE%B1-Dihydrodydrogesterone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7c/20%CE%B1-Dihydrodydrogesterone.svg/225px-20%CE%B1-Dihydrodydrogesterone.svg.png" decoding="async" width="225" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7c/20%CE%B1-Dihydrodydrogesterone.svg/338px-20%CE%B1-Dihydrodydrogesterone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7c/20%CE%B1-Dihydrodydrogesterone.svg/450px-20%CE%B1-Dihydrodydrogesterone.svg.png 2x" data-file-width="1085" data-file-height="795" /></a><figcaption><a href="/wiki/20%CE%B1-Dihydrodydrogesterone" title="20α-Dihydrodydrogesterone">20α-Dihydrodydrogesterone</a> (20α-DHD), the main <a href="/wiki/Active_metabolite" title="Active metabolite">active form</a> of dydrogesterone.</figcaption></figure> Dydrogesterone is a highly <a href="/wiki/Binding_selectivity" title="Binding selectivity">selective</a> <a href="/wiki/Progestogen_(medication)" title="Progestogen (medication)">progestogen</a>, and due to its unique structure, unlike <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a> and many other <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestins</a>, binds almost exclusively to the <a href="/wiki/Progesterone_receptor" title="Progesterone receptor">progesterone receptor</a> (PR).<a href="#cite_note-SchindlerCampagnoli2003-44">[44]</a> The <a href="/wiki/Affinity_(pharmacology)" class="mw-redirect" title="Affinity (pharmacology)">affinity</a> of dydrogesterone for the PR is relatively low at about 16% of that of progesterone.<a href="#cite_note-pmid21376746-45">[45]</a><a href="#cite_note-CabezaHeuze2014-46">[46]</a> However, <a href="/wiki/In_vivo" title="In vivo">in vivo</a>, dydrogesterone is comparatively much more potent by the <a href="/wiki/Oral_administration" title="Oral administration">oral</a> <a href="/wiki/Route_of_administration" title="Route of administration">route</a>, with an equivalent dose, in terms of <a href="/wiki/Endometrium" title="Endometrium">endometrial</a> <a href="/wiki/Cell_proliferation" title="Cell proliferation">proliferation</a>, that is 10 to 20 times lower than that of progesterone.<a href="#cite_note-ColomboFerraboschi2006-47">[47]</a> This is due to <a href="/wiki/Pharmacokinetic" class="mw-redirect" title="Pharmacokinetic">pharmacokinetic</a> differences between the two medications, namely improved <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> and <a href="/wiki/Metabolic_stability" class="mw-redirect" title="Metabolic stability">metabolic stability</a> with dydrogesterone as well as additional progestogenic activity of its <a href="/wiki/Metabolite" title="Metabolite">metabolites</a>.<a href="#cite_note-Schindler2009-13">[13]</a> Dydrogesterone binds to and activates both of the major <a href="/wiki/Isoform" class="mw-redirect" title="Isoform">isoforms</a> of the PR, the <a href="/wiki/PR-A" class="mw-redirect" title="PR-A">PR-A</a> and <a href="/wiki/PR-B" class="mw-redirect" title="PR-B">PR-B</a>, with a similar selectivity ratio between the two receptors as that of progesterone and with lower <a href="/wiki/Efficacy" title="Efficacy">efficacy</a> at the receptors relative to progesterone.<a href="#cite_note-pmid21376746-45">[45]</a> The major <a href="/wiki/Active_metabolite" title="Active metabolite">active metabolite</a> of dydrogesterone, <a href="/wiki/20%CE%B1-dihydrodydrogesterone" class="mw-redirect" title="20α-dihydrodydrogesterone">20α-dihydrodydrogesterone</a> (20α-DHD), has progestogenic activity as well but with greatly decreased potency relative to dydrogesterone.<a href="#cite_note-pmid21376746-45">[45]</a> As with other progestogens, dydrogesterone has functional <a href="/wiki/Antiestrogen" title="Antiestrogen">antiestrogenic</a> effects in certain <a href="/wiki/Tissue_(biology)" title="Tissue (biology)">tissues</a>, for instance in the <a href="/wiki/Endometrium" title="Endometrium">endometrium</a>, and induces <a href="/wiki/Endometrial_secretory_transformation" class="mw-redirect" title="Endometrial secretory transformation">endometrial secretory transformation</a>.<a href="#cite_note-pmid16112947-7">[7]</a> Dydrogesterone does not bind importantly to the <a href="/wiki/Androgen_receptor" title="Androgen receptor">androgen</a>, <a href="/wiki/Estrogen_receptor" title="Estrogen receptor">estrogen</a>, or <a href="/wiki/Glucocorticoid_receptor" title="Glucocorticoid receptor">glucocorticoid receptor</a>.<a href="#cite_note-CabezaHeuze2014-46">[46]</a><a href="#cite_note-pmid21376746-45">[45]</a> As such, it is devoid of <a href="/wiki/Androgen" title="Androgen">androgenic</a> or <a href="/wiki/Antiandrogen" title="Antiandrogen">antiandrogenic</a>, <a href="/wiki/Estrogen" title="Estrogen">estrogenic</a> or <a href="/wiki/Antiestrogen" title="Antiestrogen">antiestrogenic</a>, and <a href="/wiki/Glucocorticoid" title="Glucocorticoid">glucocorticoid</a> or <a href="/wiki/Antiglucocorticoid" title="Antiglucocorticoid">antiglucocorticoid</a> activity.<a href="#cite_note-SchindlerCampagnoli2003-44">[44]</a><a href="#cite_note-pmid16112947-7">[7]</a><a href="#cite_note-pmid21376746-45">[45]</a> Similarly to progesterone however, dydrogesterone binds to the <a href="/wiki/Mineralocorticoid_receptor" title="Mineralocorticoid receptor">mineralocorticoid receptor</a> and possesses <a href="/wiki/Antimineralocorticoid" class="mw-redirect" title="Antimineralocorticoid">antimineralocorticoid</a> activity, but only weakly so.<a href="#cite_note-pmid16112947-7">[7]</a><a href="#cite_note-pmid21376746-45">[45]</a> Like other progestins but unlike progesterone, which forms <a href="/wiki/Sedation" title="Sedation">sedative</a> <a href="/wiki/Neurosteroid" title="Neurosteroid">neurosteroid</a> metabolites, dydrogesterone is not able to be metabolized in a similar way, and for this reason, is non-sedative.<a href="#cite_note-pmid16112947-7">[7]</a> The medication and 20α-DHD do not <a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibit</a> <a href="/wiki/5%CE%B1-reductase" class="mw-redirect" title="5α-reductase">5α-reductase</a>.<a href="#cite_note-pmid21376746-45">[45]</a> Dydrogesterone has been found to inhibit <a href="/wiki/Myometrium" title="Myometrium">myometrium</a> <a href="/wiki/Contractility" title="Contractility">contractility</a> via an undefined progesterone receptor-independent mechanism <a href="/wiki/In_vivo" title="In vivo">in vivo</a> in <a href="/wiki/Pregnancy" title="Pregnancy">pregnant</a> rats and <a href="/wiki/In_vitro" title="In vitro">in vitro</a> in human <a href="/wiki/Tissue_(biology)" title="Tissue (biology)">tissue</a> at concentrations at which progesterone and other progestogens do not.<a href="#cite_note-pmid29981319-48">[48]</a> <div class="mw-heading mw-heading4"><h4 id="Atypical_progestogenic_profile">Atypical progestogenic profile</h4>[<a href="/w/index.php?title=Dydrogesterone&action=edit&section=12" title="Edit section: Atypical progestogenic profile">edit</a>]</div> Due to its progestogenic activity, dydrogesterone can produce <a href="/wiki/Antigonadotropic" class="mw-redirect" title="Antigonadotropic">antigonadotropic</a> effects at sufficient doses in animals.<a href="#cite_note-BorisStevenson1966-49">[49]</a> However, it does not suppress secretion of the <a href="/wiki/Gonadotropin" title="Gonadotropin">gonadotropins</a>, <a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone">luteinizing hormone</a> (LH) and <a href="/wiki/Follicle-stimulating_hormone" title="Follicle-stimulating hormone">follicle-stimulating hormone</a> (FSH), or inhibit <a href="/wiki/Ovulation" title="Ovulation">ovulation</a> at typical clinical dosages in humans.<a href="#cite_note-pmid16112947-7">[7]</a><a href="#cite_note-Tausk1972-14">[14]</a><a href="#cite_note-Mittal2013-50">[50]</a> Oral doses of dydrogesterone of 5 to 40 mg/day on days 5 to 25 of the cycle fail to suppress ovulation (assessed by <a href="/wiki/Urine" title="Urine">urinary</a> <a href="/wiki/Pregnanediol" title="Pregnanediol">pregnanediol</a> and <a href="/wiki/Laparotomy" title="Laparotomy">laparotomy</a>), and one study found that ovulation persisted even in women treated with an oral dosage of as great as 400 mg/day (assessed by visual inspection of the <a href="/wiki/Ovary" title="Ovary">ovaries</a>).<a href="#cite_note-pmid22078182-51">[51]</a><a href="#cite_note-Tausk1972-14">[14]</a> Likewise, an <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">intramuscular injection</a> of 100 mg dydrogesterone in <a href="/wiki/Microcrystalline" title="Microcrystalline">microcrystalline</a> <a href="/wiki/Aqueous_suspension" class="mw-redirect" title="Aqueous suspension">aqueous suspension</a> on the first to third day of the cycle did not interfere with the development of an ovulatory pattern of spontaneous uterine contractions in women.<a href="#cite_note-Tausk1972-14">[14]</a><a href="#cite_note-EskesHein1970-52">[52]</a> A couple of conflicting studies exist on the issue of ovulation inhibition by dydrogesterone however, with findings of partial or full inhibition of ovulation by oral dydrogesterone.<a href="#cite_note-Tausk1972-14">[14]</a> This included prevention of the mid-cycle LH and FSH peaks and the luteal-phase rise in <a href="/wiki/Body_temperature" class="mw-redirect" title="Body temperature">body temperature</a> and pregnanediol <a href="/wiki/Excretion" title="Excretion">excretion</a>.<a href="#cite_note-Tausk1972-14">[14]</a> Nonetheless, the overall consensus among researchers seems to be that dydrogesterone does not inhibit ovulation in women.<a href="#cite_note-Tausk1972-14">[14]</a> The apparent inability of dydrogesterone to prevent ovulation is in contrast to all other clinically used progestogens except <a href="/wiki/Trengestone" title="Trengestone">trengestone</a>, which is closely related to dydrogesterone.<a href="#cite_note-pmid22078182-51">[51]</a><a href="#cite_note-HorskyPresl2012-53">[53]</a> Similarly to trengestone but also unlike all other clinically used progestogens, dydrogesterone does not have a <a href="/wiki/Hyperthermia" title="Hyperthermia">hyperthermic</a> effect in humans (i.e., it does not increase <a href="/wiki/Body_temperature" class="mw-redirect" title="Body temperature">body temperature</a>).<a href="#cite_note-pmid16112947-7">[7]</a><a href="#cite_note-HorskyPresl2012-53">[53]</a><a href="#cite_note-pmid679688-54">[54]</a> It has been said that the lack of ovulation inhibition and hyperthermic effect with retroprogesterone derivatives like dydrogesterone may represent a dissociation of peripheral and <a href="/wiki/Central_nervous_system" title="Central nervous system">central</a> progestogenic activity.<a href="#cite_note-Henzl1978-55">[55]</a><a href="#cite_note-Lauritzen1988-56">[56]</a> However, a related retroprogesterone derivative, trengestone, likewise does not inhibit ovulation or produce a hyperthermic effect but rather has an <a href="/wiki/Ovulation_stimulant" class="mw-redirect" title="Ovulation stimulant">inducing effect on ovulation</a>.<a href="#cite_note-HorskyPresl2012-53">[53]</a> Whereas all other assessed progestins are associated with an increased risk of <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a> when combined with an estrogen in postmenopausal women, neither oral progesterone nor dydrogesterone are associated with a significantly increased risk of breast cancer (although the risk of breast cancer is non-significantly higher with dydrogesterone).<a href="#cite_note-pmid27898258-57">[57]</a><a href="#cite_note-pmid23651281-58">[58]</a><a href="#cite_note-pmid29852797-59">[59]</a> Similarly, like oral progesterone but in contrast to other progestins, dydrogesterone does not appear to further increase the risk of <a href="/wiki/Venous_thromboembolism" class="mw-redirect" title="Venous thromboembolism">venous thromboembolism</a> when used in combination with an oral estrogen.<a href="#cite_note-pmid23835005-60">[60]</a><a href="#cite_note-pmid19565370-61">[61]</a> Dydrogesterone may also provide inferior <a href="/wiki/Endometrium" title="Endometrium">endometrial protection</a> relative to other progestins such as <a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">medroxyprogesterone acetate</a> and <a href="/wiki/Norethisterone_acetate" title="Norethisterone acetate">norethisterone acetate</a>, with a significantly increased risk of <a href="/wiki/Endometrial_cancer" title="Endometrial cancer">endometrial cancer</a> in combination with an estrogen with long-term therapy (>5 years).<a href="#cite_note-pmid26512775-62">[62]</a><a href="#cite_note-SayeghAwwad2017-63">[63]</a><a href="#cite_note-pmid19935019-64">[64]</a> <div class="mw-heading mw-heading4"><h4 id="Other_activity">Other activity</h4>[<a href="/w/index.php?title=Dydrogesterone&action=edit&section=13" title="Edit section: Other activity">edit</a>]</div> Dydrogesterone weakly stimulates the <a href="/wiki/Cell_proliferation" title="Cell proliferation">proliferation</a> of <a href="/wiki/MCF-7" title="MCF-7">MCF-7</a> <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a> <a href="/wiki/Cell_(biology)" title="Cell (biology)">cells</a> <a href="/wiki/In_vitro" title="In vitro">in vitro</a>, an action that is independent of the classical PRs and is instead mediated via the <a href="/wiki/Progesterone_receptor_membrane_component-1" class="mw-redirect" title="Progesterone receptor membrane component-1">progesterone receptor membrane component-1</a> (PGRMC1).<a href="#cite_note-pmid23758160-65">[65]</a> Certain other progestins are also active in this assay, whereas <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a> acts neutrally.<a href="#cite_note-pmid23758160-65">[65]</a> It is unclear if these findings may explain the different risks of breast cancer observed with progesterone, dydrogesterone, and other progestins such as <a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">medroxyprogesterone acetate</a> and <a href="/wiki/Norethisterone" title="Norethisterone">norethisterone</a> in <a href="/wiki/Clinical_trial" title="Clinical trial">clinical studies</a>.<a href="#cite_note-pmid31512725-66">[66]</a> <div class="mw-heading mw-heading3"><h3 id="Pharmacokinetics">Pharmacokinetics</h3>[<a href="/w/index.php?title=Dydrogesterone&action=edit&section=14" title="Edit section: Pharmacokinetics">edit</a>]</div> <div class="mw-heading mw-heading4"><h4 id="Absorption">Absorption</h4>[<a href="/w/index.php?title=Dydrogesterone&action=edit&section=15" title="Edit section: Absorption">edit</a>]</div> Dydrogesterone and its major <a href="/wiki/Metabolite" title="Metabolite">metabolite</a>, 20α-DHD, have predictable <a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">pharmacokinetics</a>. The single-dose kinetics are linear in the oral dose range of 2.5 to 10 mg. The pharmacokinetics do not change during repeated administration of up to 20 mg dydrogesterone once daily. Dydrogesterone is readily <a href="/wiki/Absorption_(pharmacokinetics)" class="mw-redirect" title="Absorption (pharmacokinetics)">absorbed</a> with <a href="/wiki/Oral_administration" title="Oral administration">oral administration</a>. The <a href="/wiki/Absolute_bioavailability" class="mw-redirect" title="Absolute bioavailability">absolute bioavailability</a> of dydrogesterone is on average 28%.<a href="#cite_note-Femoston-Label-4">[4]</a> <a href="/wiki/Transport_maximum" title="Transport maximum">Tmax</a> values vary between 0.5 and 2.5 hours.<a href="#cite_note-:2-67">[67]</a> <a href="/wiki/Steady_state#Physiology" title="Steady state">Steady state</a> is attained after 3 days of treatment.<a href="#cite_note-DYDROBOON_10mg_Film-Coated_Tablets-40">[40]</a> The levels of 20α-DHD, which is the main active metabolite, are also found to peak about 1.5 hours post-dose.<a href="#cite_note-DYDROBOON_10mg_Film-Coated_Tablets-40">[40]</a> A single <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">intramuscular injection</a> of 100 mg dydrogesterone in <a href="/wiki/Microcrystalline" title="Microcrystalline">microcrystalline</a> <a href="/wiki/Aqueous_suspension" class="mw-redirect" title="Aqueous suspension">aqueous suspension</a> has been found to have a <a href="/wiki/Duration_of_action" class="mw-redirect" title="Duration of action">duration of action</a> of 16 to 38 days in terms of clinical <a href="/wiki/Biological_effect" class="mw-redirect" title="Biological effect">biological effect</a> in the <a href="/wiki/Uterus" title="Uterus">uterus</a> in women.<a href="#cite_note-Tausk1972-14">[14]</a> This was specifically the time until the onset of <a href="/wiki/Withdrawal_bleeding" class="mw-redirect" title="Withdrawal bleeding">withdrawal bleeding</a> in estrogen-treated amenorrheic women.<a href="#cite_note-Tausk1972-14">[14]</a> <table class="wikitable plainrowheaders floatright" style="font-size:small;"> <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:Parenteral_potencies_and_durations_of_progestogens" title="Template:Parenteral potencies and durations of progestogens"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Parenteral_potencies_and_durations_of_progestogens" title="Template talk:Parenteral potencies and durations of progestogens"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Parenteral_potencies_and_durations_of_progestogens" title="Special:EditPage/Template:Parenteral potencies and durations of progestogens"><abbr title="Edit this template">e</abbr></a></li></ul></div> Parenteral potencies and durations of progestogens<a href="#cite_note-87">[a]</a><a href="#cite_note-88">[b]</a> </caption> <tbody><tr> <th scope="col" rowspan="2">Compound </th> <th scope="col" rowspan="2">Form </th> <th scope="col" colspan="3">Dose for specific uses (mg)<a href="#cite_note-89">[c]</a> </th> <th scope="col" rowspan="2"><abbr title="Duration of action">DOA</abbr><a href="#cite_note-90">[d]</a> </th></tr> <tr> <th scope="col"><abbr title="Endometrial transformation dose">TFD</abbr><a href="#cite_note-91">[e]</a> </th> <th scope="col"><abbr title="Progestogen-only injectable contraceptive dose">POICD</abbr><a href="#cite_note-92">[f]</a> </th> <th scope="col"><abbr title="Combined injectable contraceptive dose">CICD</abbr><a href="#cite_note-93">[g]</a> </th></tr> <tr> <td><a href="/wiki/Algestone_acetophenide" title="Algestone acetophenide">Algestone acetophenide</a></td> <td>Oil soln.</td> <td>–</td> <td>–</td> <td>75–150</td> <td>14–32 d </td></tr> <tr> <td><a href="/wiki/Gestonorone_caproate" title="Gestonorone caproate">Gestonorone caproate</a></td> <td>Oil soln.</td> <td>25–50</td> <td>–</td> <td>–</td> <td>8–13 d </td></tr> <tr> <td><a href="/wiki/Hydroxyprogesterone_acetate" title="Hydroxyprogesterone acetate">Hydroxyprogest. acetate</a><a href="#cite_note-mark-94">[h]</a></td> <td>Aq. susp.</td> <td>350</td> <td>–</td> <td>–</td> <td>9–16 d </td></tr> <tr> <td><a href="/wiki/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">Hydroxyprogest. caproate</a></td> <td>Oil soln.</td> <td>250–500<a href="#cite_note-div-95">[i]</a></td> <td>–</td> <td>250–500</td> <td>5–21 d </td></tr> <tr> <td><a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">Medroxyprog. acetate</a></td> <td>Aq. susp.</td> <td>50–100</td> <td>150</td> <td>25</td> <td>14–50+ d </td></tr> <tr> <td><a href="/wiki/Megestrol_acetate" title="Megestrol acetate">Megestrol acetate</a></td> <td>Aq. susp.</td> <td>–</td> <td>–</td> <td>25</td> <td>>14 d </td></tr> <tr> <td><a href="/wiki/Norethisterone_enanthate" title="Norethisterone enanthate">Norethisterone enanthate</a></td> <td>Oil soln.</td> <td>100–200</td> <td>200</td> <td>50</td> <td>11–52 d </td></tr> <tr> <td rowspan="3"><a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">Progesterone</a></td> <td>Oil soln.</td> <td>200<a href="#cite_note-div-95">[i]</a></td> <td>–</td> <td>–</td> <td>2–6 d </td></tr> <tr> <td>Aq. soln.</td> <td>?</td> <td>–</td> <td>–</td> <td>1–2 d </td></tr> <tr> <td>Aq. susp.</td> <td>50–200</td> <td>–</td> <td>–</td> <td>7–14 d </td></tr> <tr class="sortbottom"> <td colspan="7" style="width: 1px; background-color:#eaecf0; background-color:#eaecf0; text-align: center;"> <style data-mw-deduplicate="TemplateStyles:r1214851843">.mw-parser-output .hidden-begin{box-sizing:border-box;width:100%;padding:5px;border:none;font-size:95%}.mw-parser-output .hidden-title{font-weight:bold;line-height:1.6;text-align:left}.mw-parser-output .hidden-content{text-align:left}@media all and (max-width:500px){.mw-parser-output .hidden-begin{width:auto!important;clear:none!important;float:none!important}}</style><div class="hidden-begin mw-collapsible mw-collapsed" style=""><div class="hidden-title skin-nightmode-reset-color" style="text-align:center;">Notes and sources:</div><div class="hidden-content mw-collapsible-content" style=""> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-lower-alpha"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-87"><a href="#cite_ref-87">^</a> Sources: <a href="#cite_note-KnörrBeller2013-68">[68]</a><a href="#cite_note-KnörrKnörr-Gärtner2013y-69">[69]</a><a href="#cite_note-Labhart2012-70">[70]</a><a href="#cite_note-HorskyPresl1981-71">[71]</a><a href="#cite_note-Ufer1969-72">[72]</a><a href="#cite_note-Pschyrembel1968r-73">[73]</a><a href="#cite_note-Ferin1972-74">[74]</a><a href="#cite_note-HenzlEdwards1999u-75">[75]</a><a href="#cite_note-Brotherton1976-76">[76]</a><a href="#cite_note-pmid8013220-77">[77]</a><a href="#cite_note-pmid8013216-78">[78]</a><a href="#cite_note-Goebelsmann1986-79">[79]</a><a href="#cite_note-BeckerDüsterberg1980-80">[80]</a><a href="#cite_note-MoltzHaase2008-81">[81]</a><a href="#cite_note-WrightBurgess2012-82">[82]</a><a href="#cite_note-ChuLi1986-83">[83]</a><a href="#cite_note-RunnebaumRabe2012-84">[84]</a><a href="#cite_note-ArtiniGenazzani2001-85">[85]</a><a href="#cite_note-KingBrucker2013-86">[86]</a> </li> <li id="cite_note-88"><a href="#cite_ref-88">^</a> All given by <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">intramuscular</a> or <a href="/wiki/Subcutaneous_injection" class="mw-redirect" title="Subcutaneous injection">subcutaneous injection</a>. </li> <li id="cite_note-89"><a href="#cite_ref-89">^</a> Progesterone production during the <a href="/wiki/Luteal_phase" title="Luteal phase">luteal phase</a> is ~25 (15–50) mg/day. The <a href="/wiki/Ovulation-inhibiting_dose" class="mw-redirect" title="Ovulation-inhibiting dose"><abbr title="ovulation-inhibiting dose">OID</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 ovulation-inhibiting dose of OHPC is 250 to 500 mg/month. </li> <li id="cite_note-90"><a href="#cite_ref-90">^</a> Duration of action in days. </li> <li id="cite_note-91"><a href="#cite_ref-91">^</a> Usually given for 14 days. </li> <li id="cite_note-92"><a href="#cite_ref-92">^</a> Usually dosed every two to three months. </li> <li id="cite_note-93"><a href="#cite_ref-93">^</a> Usually dosed once monthly. </li> <li id="cite_note-mark-94"><a href="#cite_ref-mark_94-0">^</a> Never marketed or approved by this route. </li> <li id="cite_note-div-95">^ <a href="#cite_ref-div_95-0">a</a> <a href="#cite_ref-div_95-1">b</a> In divided doses (2 × 125 or 250 mg for <abbr title="hydroxyprogesterone caproate">OHPC</abbr>, 10 × 20 mg for <abbr title="progesterone">P4</abbr>). </li> </ol></div></div></div></div> </td></tr></tbody></table> <div class="mw-heading mw-heading4"><h4 id="Distribution">Distribution</h4>[<a href="/w/index.php?title=Dydrogesterone&action=edit&section=16" title="Edit section: Distribution">edit</a>]</div> The <a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">plasma protein binding</a> of dydrogesterone and 20α-DHD are unknown. Based on the plasma protein binding of other progestins however, they are probably bound to <a href="/wiki/Human_serum_albumin" title="Human serum albumin">albumin</a> and not to <a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin">sex hormone-binding globulin</a> or <a href="/wiki/Corticosteroid-binding_globulin" class="mw-redirect" title="Corticosteroid-binding globulin">corticosteroid-binding globulin</a>.<a href="#cite_note-FRCOG2015-6">[6]</a><a href="#cite_note-pmid16112947-7">[7]</a> <div class="mw-heading mw-heading4"><h4 id="Metabolism">Metabolism</h4>[<a href="/w/index.php?title=Dydrogesterone&action=edit&section=17" title="Edit section: Metabolism">edit</a>]</div> The <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> of dydrogesterone occurs in the <a href="/wiki/Liver" title="Liver">liver</a>.<a href="#cite_note-Carp2015-96">[87]</a> It is virtually completely metabolized.<a href="#cite_note-Carp2015-96">[87]</a> The primary metabolic pathway is the <a href="/wiki/Hydrogenation" title="Hydrogenation">hydrogenation</a> of the 20-<a href="/wiki/Ketone" title="Ketone">keto group</a> mainly by <a href="/wiki/AKR1C1" title="AKR1C1">AKR1C1</a> and to a lesser extent <a href="/wiki/AKR1C3" title="AKR1C3">AKR1C3</a>, resulting in 20α-DHD. This active metabolite is a progestogen similarly to dydrogesterone, albeit with much lower potency.<a href="#cite_note-BeraničGobec2011-8">[8]</a> With oral administration of dydrogesterone, circulating levels of 20α-DHD are substantially higher than those of dydrogesterone.<a href="#cite_note-pmid21376746-45">[45]</a> The ratios of 20α-DHD to dydrogesterone in terms of <a href="/wiki/Cmax_(pharmacology)" title="Cmax (pharmacology)">peak</a> levels and <a href="/wiki/Area_under_the_curve_(pharmacokinetics)" title="Area under the curve (pharmacokinetics)">area-under-the-curve</a> (AUC) levels have been found to be 25:1 and 40:1, respectively.<a href="#cite_note-pmid21376746-45">[45]</a> For these reasons, despite the lower relative progestogenic potency of 20α-DHD, dydrogesterone may act as a <a href="/wiki/Prodrug" title="Prodrug">prodrug</a> of this metabolite.<a href="#cite_note-pmid21376746-45">[45]</a> The metabolism of dydrogesterone differs from progesterone.<a href="#cite_note-Tausk1972-14">[14]</a> Whereas the major <a href="/wiki/Metabolite" title="Metabolite">metabolite</a> of progesterone is <a href="/wiki/Pregnanediol" title="Pregnanediol">pregnanediol</a>, the corresponding derivative of dydrogesterone, retropregnanediol, cannot be detected in <a href="/wiki/Urine" title="Urine">urine</a> with oral administration of dydrogesterone.<a href="#cite_note-Tausk1972-14">[14]</a> All of the metabolites of dydrogesterone retain the 4,6-diene-3-one structure and are metabolically stable. As such, similarly to progesterone, dydrogesterone does not undergo <a href="/wiki/Aromatization" title="Aromatization">aromatization</a>. The mean <a href="/wiki/Biological_half-life" title="Biological half-life">elimination half-lives</a> of dydrogesterone and 20α-DHD are in the ranges of 5 to 7 hours and 14 to 17 hours, respectively.<a href="#cite_note-BińkowskaWoroń2015-9">[9]</a> <div class="mw-heading mw-heading4"><h4 id="Excretion">Excretion</h4>[<a href="/w/index.php?title=Dydrogesterone&action=edit&section=18" title="Edit section: Excretion">edit</a>]</div> Dydrogesterone and its metabolites are <a href="/wiki/Excretion" title="Excretion">excreted</a> predominantly in <a href="/wiki/Urine" title="Urine">urine</a>. Total clearance of plasma is at a rate of 6.4 L/min. Within 72 hours, excretion is virtually complete. 20α-DHD is preponderantly present in the urine as a conjugate of <a href="/wiki/Glucuronic_acid" title="Glucuronic acid">glucuronic acid</a>. Approximately 85% of the oral dose is successfully removed from the body within 24 hours. Around 90% of excreted material is 20α-DHD.<a href="#cite_note-Tausk1972-14">[14]</a> <div class="mw-heading mw-heading4"><h4 id="Miscellaneous">Miscellaneous</h4>[<a href="/w/index.php?title=Dydrogesterone&action=edit&section=19" title="Edit section: Miscellaneous">edit</a>]</div> The <a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">pharmacokinetics</a> of dydrogesterone have been reviewed.<a href="#cite_note-pmid16112947-7">[7]</a><a href="#cite_note-Springer2013-97">[88]</a> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2>[<a href="/w/index.php?title=Dydrogesterone&action=edit&section=20" title="Edit section: Chemistry">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Retroprogesterone" title="Retroprogesterone">Retroprogesterone</a> and <a href="/wiki/List_of_progestogens#Retroprogesterone_derivatives" title="List of progestogens">List of progestogens § Retroprogesterone derivatives</a></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Progesterone_and_dydrogesterone_3D_chemical_structures_comparison.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d7/Progesterone_and_dydrogesterone_3D_chemical_structures_comparison.png/250px-Progesterone_and_dydrogesterone_3D_chemical_structures_comparison.png" decoding="async" width="225" height="364" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d7/Progesterone_and_dydrogesterone_3D_chemical_structures_comparison.png/500px-Progesterone_and_dydrogesterone_3D_chemical_structures_comparison.png 1.5x" data-file-width="1733" data-file-height="2800" /></a><figcaption>A 3D schematic representation of the chemical structures of progesterone (top) and dydrogesterone (bottom), showing the retrosteroid spatial configuration of dydrogesterone.<a href="#cite_note-pmid16112947-7">[7]</a><a href="#cite_note-SchindlerCampagnoli2003-44">[44]</a></figcaption></figure> Dydrogesterone, also known as 6-dehydro-9β,10α-progesterone or as 9β,10α-pregna-4,6-diene-3,20-dione, is a <a href="/wiki/Synthetic_compound" class="mw-redirect" title="Synthetic compound">synthetic</a> <a href="/wiki/Pregnane" title="Pregnane">pregnane</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/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a> and <a href="/wiki/Retroprogesterone" title="Retroprogesterone">retroprogesterone</a> (9β,10α-progesterone).<a href="#cite_note-Elks2014-2">[2]</a><a href="#cite_note-IndexNominum2000-3">[3]</a> Retroprogesterone derivatives like dydrogesterone are <a href="/wiki/Structural_analog" title="Structural analog">analogues</a> of progesterone in which the <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> atom at the 9th carbon has been switched from the α-position (below the plane) to the β-position (above the plane) and the <a href="/wiki/Methyl_group" title="Methyl group">methyl group</a> at the 10th carbon has been switched from the β-position to the α-position.<a href="#cite_note-HorskyPresl2012-53">[53]</a> This reversed configuration in dydrogesterone results in a "bent" spatial geometry in which the plane of rings A and B is orientated at a 60° angle below the rings C and D.<a href="#cite_note-pmid16112947-7">[7]</a> Dydrogesterone also has an additional <a href="/wiki/Double_bond" title="Double bond">double bond</a> between the C6 and C7 positions (4,6-dien-3-one configuration).<a href="#cite_note-Elks2014-2">[2]</a><a href="#cite_note-IndexNominum2000-3">[3]</a> While its chemical structure is close to that of progesterone, these changes result in dydrogesterone having improved oral activity and metabolic stability, among other differences, in comparison to progesterone.<a href="#cite_note-pmid16112947-7">[7]</a><a href="#cite_note-SchindlerCampagnoli2003-44">[44]</a> <div class="mw-heading mw-heading3"><h3 id="Analogues">Analogues</h3>[<a href="/w/index.php?title=Dydrogesterone&action=edit&section=21" title="Edit section: Analogues">edit</a>]</div> Other retroprogesterone derivatives, and analogues of dydrogesterone, include <a href="/wiki/Trengestone" title="Trengestone">trengestone</a> (1,6-didehydro-6-chlororetroprogesterone) and <a href="/wiki/Ro_6-3129" title="Ro 6-3129">Ro 6-3129</a> (16α-ethylthio-6-dehydroretroprogesterone).<a href="#cite_note-Elks2014-2">[2]</a><a href="#cite_note-IndexNominum2000-3">[3]</a> <div class="mw-heading mw-heading3"><h3 id="Synthesis">Synthesis</h3>[<a href="/w/index.php?title=Dydrogesterone&action=edit&section=22" title="Edit section: Synthesis">edit</a>]</div> Dydrogesterone is synthesized and manufactured by treatment of progesterone with <a href="/wiki/Ultraviolet" title="Ultraviolet">ultraviolet light</a> exposure.<a href="#cite_note-SchindlerCampagnoli2003-44">[44]</a> <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">Chemical syntheses</a> of dydrogesterone have been published.<a href="#cite_note-Springer2013-97">[88]</a> <div class="mw-heading mw-heading2"><h2 id="History">History</h2>[<a href="/w/index.php?title=Dydrogesterone&action=edit&section=23" title="Edit section: History">edit</a>]</div> Dydrogesterone is a progestin which was first synthesized by Duphar in the 1950s and was first introduced to the market in 1961. It is unique, being the only retrosteroid that is commercially available and its molecular structure is closely related to that of natural progesterone,<a href="#cite_note-Schindler2009-13">[13]</a> but it has enhanced oral <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a>. It is estimated that during the period from 1977 to 2005<a href="#cite_note-98">[89]</a> around 38 million women were treated with dydrogesterone and that <a href="/wiki/Fetuses" class="mw-redirect" title="Fetuses">fetuses</a> were exposed to dydrogesterone <a href="/wiki/Uterus" title="Uterus">in utero</a> in more than 10 million pregnancies. It has been approved in more than 100 countries worldwide. It is commercially marketed under the brand name Dydroboon and manufactured by <a href="/wiki/Mankind_Pharma" title="Mankind Pharma">Mankind Pharma</a>. Dydrogesterone was first introduced, by Duphar, as Duphaston in the <a href="/wiki/United_Kingdom" title="United Kingdom">United Kingdom</a> in 1961.<a href="#cite_note-Publishing2013-15">[15]</a> Subsequently, it was introduced in the <a href="/wiki/United_States" title="United States">United States</a> as Duphaston and Gynorest in 1962 and 1968, respectively.<a href="#cite_note-Publishing2013-15">[15]</a> Duphaston was removed from the United States market in 1979,<a href="#cite_note-Freedman1986-99">[90]</a> and Gynorest is also no longer available in the United States.<a href="#cite_note-FDA-100">[91]</a> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2>[<a href="/w/index.php?title=Dydrogesterone&action=edit&section=24" title="Edit section: Society and culture">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Generic_names">Generic names</h3>[<a href="/w/index.php?title=Dydrogesterone&action=edit&section=25" title="Edit section: Generic names">edit</a>]</div> Dydrogesterone is the <a href="/wiki/Generic_term" class="mw-redirect" title="Generic term">generic name</a> of the drug and its <a href="/wiki/International_Nonproprietary_Name" class="mw-redirect" title="International Nonproprietary Name"><abbr title="International Nonproprietary Name">INN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip International Nonproprietary Name, <a href="/wiki/United_States_Adopted_Name" title="United States Adopted Name"><abbr title="United States Adopted Name">USAN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip United States Adopted Name, and <a href="/wiki/British_Approved_Name" title="British Approved Name"><abbr title="British Approved Name">BAN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip British Approved Name, while dydrogestérone is its <a href="/wiki/D%C3%A9nomination_Commune_Fran%C3%A7aise" title="Dénomination Commune Française"><abbr title="Dénomination Commune Française">DCF</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Dénomination Commune Française and didrogesterone 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.<a href="#cite_note-Elks2014-2">[2]</a><a href="#cite_note-IndexNominum2000-3">[3]</a><a href="#cite_note-Publishing2013-15">[15]</a><a href="#cite_note-Drugs.com-101">[92]</a> It was also originally known as isopregnenone.<a href="#cite_note-Elks2014-2">[2]</a><a href="#cite_note-IndexNominum2000-3">[3]</a><a href="#cite_note-Publishing2013-15">[15]</a><a href="#cite_note-Drugs.com-101">[92]</a> Dydrogesterone has also been referred to as retroprogesterone, but should not be confused with <a href="/wiki/Retroprogesterone" title="Retroprogesterone">retroprogesterone</a>.<a href="#cite_note-GöretzlehnerLauritzen2012-102">[93]</a> <div class="mw-heading mw-heading3"><h3 id="Brand_names">Brand names</h3>[<a href="/w/index.php?title=Dydrogesterone&action=edit&section=26" title="Edit section: Brand names">edit</a>]</div> Dydrogesterone is marketed mainly under the brand names Duphaston (alone) and Femoston (in combination with <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a>).<a href="#cite_note-Drugs.com-101">[92]</a><a href="#cite_note-IndexNominum2000-3">[3]</a> It also is or has been marketed alone under the brand names Dabroston, Divatrone, Dufaston, Duvaron, Dydrofem, Femoston, Gestatron, Gynorest, Prodel, Retrone, Terolut and Zuviston and in combination with estradiol under the brand names Climaston, Femaston, and Femphascyl.<a href="#cite_note-brands-1">[1]</a><a href="#cite_note-IndexNominum2000-3">[3]</a><a href="#cite_note-Elks2014-2">[2]</a><a href="#cite_note-Publishing2013-15">[15]</a> <div class="mw-heading mw-heading3"><h3 id="Availability">Availability</h3>[<a href="/w/index.php?title=Dydrogesterone&action=edit&section=27" title="Edit section: Availability">edit</a>]</div> Dydrogesterone is available widely throughout the world.<a href="#cite_note-Drugs.com-101">[92]</a><a href="#cite_note-IndexNominum2000-3">[3]</a> It is marketed in the <a href="/wiki/United_Kingdom" title="United Kingdom">United Kingdom</a>, <a href="/wiki/India" title="India">India</a>, <a href="/wiki/Ireland" title="Ireland">Ireland</a>, <a href="/wiki/South_Africa" title="South Africa">South Africa</a>, and <a href="/wiki/Australia" title="Australia">Australia</a>, but not in the <a href="/wiki/United_States" title="United States">United States</a>, <a href="/wiki/Canada" title="Canada">Canada</a>, or <a href="/wiki/New_Zealand" title="New Zealand">New Zealand</a>.<a href="#cite_note-Drugs.com-101">[92]</a><a href="#cite_note-IndexNominum2000-3">[3]</a> The medication was previously available in the United States,<a href="#cite_note-Publishing2013-15">[15]</a> but has since been discontinued in this country.<a href="#cite_note-Manu2000-16">[16]</a> Dydrogesterone is also available in elsewhere in <a href="/wiki/Europe" title="Europe">Europe</a>, as well as in <a href="/wiki/Central_America" title="Central America">Central</a> and <a href="/wiki/South_America" title="South America">South America</a>, <a href="/wiki/Asia" title="Asia">Asia</a>, and <a href="/wiki/North_Africa" title="North Africa">North Africa</a>.<a href="#cite_note-Drugs.com-101">[92]</a><a href="#cite_note-IndexNominum2000-3">[3]</a> <div class="mw-heading mw-heading2"><h2 id="References">References</h2>[<a href="/w/index.php?title=Dydrogesterone&action=edit&section=28" title="Edit section: References">edit</a>]</div> <ul><li><a href="/wiki/Estradiol/dydrogesterone" title="Estradiol/dydrogesterone">Estradiol/dydrogesterone</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References_2">References</h2>[<a href="/w/index.php?title=Dydrogesterone&action=edit&section=29" title="Edit section: References">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626" /><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-brands-1">^ <a href="#cite_ref-brands_1-0">a</a> <a href="#cite_ref-brands_1-1">b</a> <a href="#cite_ref-brands_1-2">c</a> <style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output 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"Oral estradiol and dydrogesterone combination therapy in postmenopausal women: review of efficacy and safety". Maturitas. 76 (1): 10–21. <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.maturitas.2013.05.018">10.1016/j.maturitas.2013.05.018</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/23835005">23835005</a>. <q>Dydrogesterone did not increase the risk of VTE associated with oral estrogen (odds ratio (OR) 0.9, 95% CI 0.4–2.3). Other progestogens (OR 3.9, 95% CI 1.5–10.0) were found to further increase the risk of VTE associated with oral estrogen (OR 4.2, 95% CI 1.5–11.6).</q></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=Oral+estradiol+and+dydrogesterone+combination+therapy+in+postmenopausal+women%3A+review+of+efficacy+and+safety&rft.volume=76&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E10-%3C%2Fspan%3E21&rft.date=2013-09&rft_id=info%3Adoi%2F10.1016%2Fj.maturitas.2013.05.018&rft_id=info%3Apmid%2F23835005&rft.aulast=Stevenson&rft.aufirst=JC&rft.au=Panay%2C+N&rft.au=Pexman-Fieth%2C+C&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADydrogesterone" class="Z3988"> </li> <li id="cite_note-pmid19565370-61"><a href="#cite_ref-pmid19565370_61-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSchneiderJickMeier2009" class="citation journal cs1">Schneider C, Jick SS, Meier CR (October 2009). 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Springer Science & Business Media. pp. 554–. <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=554-&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%3DPA554&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADydrogesterone" class="Z3988"> </li> <li id="cite_note-HorskyPresl1981-71"><a href="#cite_ref-HorskyPresl1981_71-0">^</a> <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=PA313">"Hormonal Treatment of Disorders of the Menstrual Cycle"</a>. In Horsky J, Presl K (eds.). Ovarian Function and its Disorders: Diagnosis and Therapy. Springer Science & Business Media. pp. 309–332. <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%3DPA313&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADydrogesterone" class="Z3988"> </li> <li id="cite_note-Ufer1969-72"><a href="#cite_ref-Ufer1969_72-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFUfer1969" class="citation book cs1">Ufer J (1969). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=G8VsAAAAMAAJ">The Principles and Practice of Hormone Therapy in Gynaecology and Obstetrics</a>. de Gruyter. p. 49. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9783110006148" title="Special:BookSources/9783110006148"><bdi>9783110006148</bdi></a>. <q>17α-Hydroxyprogesterone caproate is a depot progestogen which is entirely free of side actions. The dose required to induce secretory changes in primed endometrium is about 250 mg. per menstrual cycle.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Principles+and+Practice+of+Hormone+Therapy+in+Gynaecology+and+Obstetrics&rft.pages=49&rft.pub=de+Gruyter&rft.date=1969&rft.isbn=9783110006148&rft.aulast=Ufer&rft.aufirst=J&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DG8VsAAAAMAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADydrogesterone" class="Z3988"> </li> <li id="cite_note-Pschyrembel1968r-73"><a href="#cite_ref-Pschyrembel1968r_73-0">^</a> <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">Praktische Gynäkologie: für Studierende und Ärzte</a>. Walter de Gruyter. pp. 598, 601. <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=598%2C+601&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%3Fid%3DvVaTnHDFzZ0C%26pg%3DPA598&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADydrogesterone" class="Z3988"> </li> <li id="cite_note-Ferin1972-74"><a href="#cite_ref-Ferin1972_74-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFerin1972" class="citation book cs1">Ferin J (September 1972). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=Nv5sAAAAMAAJ">"Effects, Duration of Action and Metabolism in Man"</a>. 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Pergamon Press. pp. 13–24. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0080168128" title="Special:BookSources/978-0080168128"><bdi>978-0080168128</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/278011135">278011135</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Effects%2C+Duration+of+Action+and+Metabolism+in+Man&rft.btitle=Pharmacology+of+the+Endocrine+System+and+Related+Drugs%3A+Progesterone%2C+Progestational+Drugs+and+Antifertility+Agents&rft.pages=%3Cspan+class%3D%22nowrap%22%3E13-%3C%2Fspan%3E24&rft.pub=Pergamon+Press&rft.date=1972-09&rft_id=info%3Aoclcnum%2F278011135&rft.isbn=978-0080168128&rft.aulast=Ferin&rft.aufirst=J&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DNv5sAAAAMAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADydrogesterone" class="Z3988"> </li> <li id="cite_note-HenzlEdwards1999u-75"><a href="#cite_ref-HenzlEdwards1999u_75-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHenzlEdwards1999" class="citation book cs1">Henzl MR, Edwards JA (10 November 1999). "Pharmacology of Progestins: 17α-Hydroxyprogesterone Derivatives and Progestins of the First and Second Generation". In Sitruk-Ware R, Mishell DR (eds.). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=vGJJHsJASekC">Progestins and Antiprogestins in Clinical Practice</a>. Taylor & Francis. pp. 101–132. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-8247-8291-7" title="Special:BookSources/978-0-8247-8291-7"><bdi>978-0-8247-8291-7</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+Progestins%3A+17%CE%B1-Hydroxyprogesterone+Derivatives+and+Progestins+of+the+First+and+Second+Generation&rft.btitle=Progestins+and+Antiprogestins+in+Clinical+Practice&rft.pages=%3Cspan+class%3D%22nowrap%22%3E101-%3C%2Fspan%3E132&rft.pub=Taylor+%26+Francis&rft.date=1999-11-10&rft.isbn=978-0-8247-8291-7&rft.aulast=Henzl&rft.aufirst=MR&rft.au=Edwards%2C+JA&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DvGJJHsJASekC&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADydrogesterone" class="Z3988"> </li> <li id="cite_note-Brotherton1976-76"><a href="#cite_ref-Brotherton1976_76-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBrotherton1976" class="citation book cs1">Brotherton J (1976). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=zt5sAAAAMAAJ">Sex Hormone Pharmacology</a>. Academic Press. p. 114. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-12-137250-7" title="Special:BookSources/978-0-12-137250-7"><bdi>978-0-12-137250-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Sex+Hormone+Pharmacology&rft.pages=114&rft.pub=Academic+Press&rft.date=1976&rft.isbn=978-0-12-137250-7&rft.aulast=Brotherton&rft.aufirst=J&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dzt5sAAAAMAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADydrogesterone" class="Z3988"> </li> <li id="cite_note-pmid8013220-77"><a href="#cite_ref-pmid8013220_77-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSang1994" class="citation journal cs1">Sang GW (April 1994). "Pharmacodynamic effects of once-a-month combined injectable contraceptives". Contraception. 49 (4): 361–385. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0010-7824%2894%2990033-7">10.1016/0010-7824(94)90033-7</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/8013220">8013220</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=Pharmacodynamic+effects+of+once-a-month+combined+injectable+contraceptives&rft.volume=49&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E361-%3C%2Fspan%3E385&rft.date=1994-04&rft_id=info%3Adoi%2F10.1016%2F0010-7824%2894%2990033-7&rft_id=info%3Apmid%2F8013220&rft.aulast=Sang&rft.aufirst=GW&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADydrogesterone" class="Z3988"> </li> <li id="cite_note-pmid8013216-78"><a href="#cite_ref-pmid8013216_78-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFToppozada1994" class="citation journal cs1">Toppozada MK (April 1994). 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In Gregoire AT, Blye RP (eds.). Contraceptive Steroids: Pharmacology and Safety. Springer Science & Business Media. pp. 67–111. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-1-4613-2241-2_4">10.1007/978-1-4613-2241-2_4</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4613-2241-2" title="Special:BookSources/978-1-4613-2241-2"><bdi>978-1-4613-2241-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Pharmacokinetics+of+Contraceptive+Steroids+in+Humans&rft.btitle=Contraceptive+Steroids%3A+Pharmacology+and+Safety&rft.pages=%3Cspan+class%3D%22nowrap%22%3E67-%3C%2Fspan%3E111&rft.pub=Springer+Science+%26+Business+Media&rft.date=1986&rft_id=info%3Adoi%2F10.1007%2F978-1-4613-2241-2_4&rft.isbn=978-1-4613-2241-2&rft.aulast=Goebelsmann&rft.aufirst=U&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D7dnTBwAAQBAJ%26pg%3DPA67&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADydrogesterone" class="Z3988"> </li> <li id="cite_note-BeckerDüsterberg1980-80"><a href="#cite_ref-BeckerDüsterberg1980_80-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBeckerDüsterbergKlosterhalfen1980" class="citation journal cs1">Becker H, Düsterberg B, Klosterhalfen H (1980). "[Bioavailability of cyproterone acetate after oral and intramuscular application in men (author's transl)]" [Bioavailability of Cyproterone Acetate after Oral and Intramuscular Application in Men]. Urologia Internationalis. 35 (6): 381–385. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1159%2F000280353">10.1159/000280353</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/6452729">6452729</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Urologia+Internationalis&rft.atitle=%5BBioavailability+of+cyproterone+acetate+after+oral+and+intramuscular+application+in+men+%28author%27s+transl%29%5D&rft.volume=35&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E381-%3C%2Fspan%3E385&rft.date=1980&rft_id=info%3Adoi%2F10.1159%2F000280353&rft_id=info%3Apmid%2F6452729&rft.aulast=Becker&rft.aufirst=H&rft.au=D%C3%BCsterberg%2C+B&rft.au=Klosterhalfen%2C+H&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADydrogesterone" class="Z3988"> </li> <li id="cite_note-MoltzHaase2008-81"><a href="#cite_ref-MoltzHaase2008_81-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMoltzHaaseSchwartzHammerstein1983" class="citation journal cs1">Moltz L, Haase F, Schwartz U, Hammerstein J (May 1983). "[Treatment of virilized women with intramuscular administration of cyproterone acetate]" [Efficacy of Intra muscularly Applied Cyproterone Acetate in Hyperandrogenism]. Geburtshilfe und Frauenheilkunde. 43 (5): 281–287. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1055%2Fs-2008-1036893">10.1055/s-2008-1036893</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/6223851">6223851</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Geburtshilfe+und+Frauenheilkunde&rft.atitle=%5BTreatment+of+virilized+women+with+intramuscular+administration+of+cyproterone+acetate%5D&rft.volume=43&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E281-%3C%2Fspan%3E287&rft.date=1983-05&rft_id=info%3Adoi%2F10.1055%2Fs-2008-1036893&rft_id=info%3Apmid%2F6223851&rft.aulast=Moltz&rft.aufirst=L&rft.au=Haase%2C+F&rft.au=Schwartz%2C+U&rft.au=Hammerstein%2C+J&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADydrogesterone" class="Z3988"> </li> <li id="cite_note-WrightBurgess2012-82"><a href="#cite_ref-WrightBurgess2012_82-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWrightBurgess2012" class="citation book cs1">Wright JC, Burgess DJ (29 January 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=36nkGjEGEToC&pg=PA114">Long Acting Injections and Implants</a>. Springer Science & Business Media. pp. 114–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4614-0554-2" title="Special:BookSources/978-1-4614-0554-2"><bdi>978-1-4614-0554-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Long+Acting+Injections+and+Implants&rft.pages=114-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-01-29&rft.isbn=978-1-4614-0554-2&rft.aulast=Wright&rft.aufirst=JC&rft.au=Burgess%2C+DJ&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D36nkGjEGEToC%26pg%3DPA114&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADydrogesterone" class="Z3988"> </li> <li id="cite_note-ChuLi1986-83"><a href="#cite_ref-ChuLi1986_83-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFChuLiZhao1986" class="citation journal cs1">Chu YH, Li Q, Zhao ZF (April 1986). <a rel="nofollow" class="external text" href="http://en.cnki.com.cn/Article_en/CJFDTOTAL-GLYZ198604003.htm">"Pharmacokinetics of megestrol acetate in women receiving IM injection of estradiol-megestrol long-acting injectable contraceptive"</a>. The Chinese Journal of Clinical Pharmacology. <q>The results showed that after injection the concentration of plasma MA increased rapidly. The meantime of peak plasma MA level was 3rd day, there was a linear relationship between log of plasma MA concentration and time (day) after administration in all subjects, elimination phase half-life t1/2β = 14.35 ± 9.1 days.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Chinese+Journal+of+Clinical+Pharmacology&rft.atitle=Pharmacokinetics+of+megestrol+acetate+in+women+receiving+IM+injection+of+estradiol-megestrol+long-acting+injectable+contraceptive&rft.date=1986-04&rft.aulast=Chu&rft.aufirst=YH&rft.au=Li%2C+Q&rft.au=Zhao%2C+ZF&rft_id=http%3A%2F%2Fen.cnki.com.cn%2FArticle_en%2FCJFDTOTAL-GLYZ198604003.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADydrogesterone" class="Z3988"> </li> <li id="cite_note-RunnebaumRabe2012-84"><a href="#cite_ref-RunnebaumRabe2012_84-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRunnebaumRabeKiesel2012" class="citation book cs1">Runnebaum BC, Rabe T, Kiesel L (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=LtT6CAAAQBAJ&pg=PA429">Female Contraception: Update and Trends</a>. Springer Science & Business Media. pp. 429–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-73790-9" title="Special:BookSources/978-3-642-73790-9"><bdi>978-3-642-73790-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Female+Contraception%3A+Update+and+Trends&rft.pages=429-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-3-642-73790-9&rft.aulast=Runnebaum&rft.aufirst=BC&rft.au=Rabe%2C+T&rft.au=Kiesel%2C+L&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DLtT6CAAAQBAJ%26pg%3DPA429&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADydrogesterone" class="Z3988"> </li> <li id="cite_note-ArtiniGenazzani2001-85"><a href="#cite_ref-ArtiniGenazzani2001_85-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFArtiniGenazzaniPetraglia2001" class="citation book cs1">Artini PG, Genazzani AR, Petraglia F (11 December 2001). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=dknDdAonzlUC&pg=PA105">Advances in Gynecological Endocrinology</a>. CRC Press. pp. 105–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-84214-071-0" title="Special:BookSources/978-1-84214-071-0"><bdi>978-1-84214-071-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Advances+in+Gynecological+Endocrinology&rft.pages=105-&rft.pub=CRC+Press&rft.date=2001-12-11&rft.isbn=978-1-84214-071-0&rft.aulast=Artini&rft.aufirst=PG&rft.au=Genazzani%2C+AR&rft.au=Petraglia%2C+F&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DdknDdAonzlUC%26pg%3DPA105&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADydrogesterone" class="Z3988"> </li> <li id="cite_note-KingBrucker2013-86"><a href="#cite_ref-KingBrucker2013_86-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKingBruckerKriebsFahey2013" class="citation book cs1">King TL, Brucker MC, Kriebs JM, Fahey JO (21 October 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=dbaNAQAAQBAJ&pg=PA495">Varney's Midwifery</a>. Jones & Bartlett Publishers. pp. 495–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-284-02542-2" title="Special:BookSources/978-1-284-02542-2"><bdi>978-1-284-02542-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Varney%27s+Midwifery&rft.pages=495-&rft.pub=Jones+%26+Bartlett+Publishers&rft.date=2013-10-21&rft.isbn=978-1-284-02542-2&rft.aulast=King&rft.aufirst=TL&rft.au=Brucker%2C+MC&rft.au=Kriebs%2C+JM&rft.au=Fahey%2C+JO&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DdbaNAQAAQBAJ%26pg%3DPA495&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADydrogesterone" class="Z3988"> </li> <li id="cite_note-Carp2015-96">^ <a href="#cite_ref-Carp2015_96-0">a</a> <a href="#cite_ref-Carp2015_96-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCarp2015" class="citation journal cs1">Carp HJ (2015). 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Springer-Verlag. 27 November 2013. pp. 10–, 275–276. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-99941-3" title="Special:BookSources/978-3-642-99941-3"><bdi>978-3-642-99941-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Die+Gestagene&rft.pages=10-%2C+%3Cspan+class%3D%22nowrap%22%3E275-%3C%2Fspan%3E276&rft.pub=Springer-Verlag&rft.date=2013-11-27&rft.isbn=978-3-642-99941-3&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dt8GpBgAAQBAJ%26pg%3DPA10&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADydrogesterone" class="Z3988"> </li> <li id="cite_note-98"><a href="#cite_ref-98">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFQueisser-Luft2009" class="citation journal cs1">Queisser-Luft A (June 2009). "Dydrogesterone use during pregnancy: overview of birth defects reported since 1977". Early Human Development. 85 (6): 375–7. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.earlhumdev.2008.12.016">10.1016/j.earlhumdev.2008.12.016</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/19193503">19193503</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Early+Human+Development&rft.atitle=Dydrogesterone+use+during+pregnancy%3A+overview+of+birth+defects+reported+since+1977&rft.volume=85&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E375-%3C%2Fspan%3E7&rft.date=2009-06&rft_id=info%3Adoi%2F10.1016%2Fj.earlhumdev.2008.12.016&rft_id=info%3Apmid%2F19193503&rft.aulast=Queisser-Luft&rft.aufirst=A&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADydrogesterone" class="Z3988"> </li> <li id="cite_note-Freedman1986-99"><a href="#cite_ref-Freedman1986_99-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFreedman1986" class="citation book cs1">Freedman W (1986). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=k85WAAAAIAAJ">International Products Liability</a>. Kluwer Law Book Publishers. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-930273-10-1" title="Special:BookSources/978-0-930273-10-1"><bdi>978-0-930273-10-1</bdi></a>. <q>Duphaston was removed from the market in 1979 or about two years after the FDA required the defendant to place warnings on the product.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=International+Products+Liability&rft.pub=Kluwer+Law+Book+Publishers&rft.date=1986&rft.isbn=978-0-930273-10-1&rft.aulast=Freedman&rft.aufirst=W&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dk85WAAAAIAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADydrogesterone" class="Z3988"> </li> <li id="cite_note-FDA-100"><a href="#cite_ref-FDA_100-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=017388">"FDA Approved Drugs"</a>. U.S. Food & Drug Administration.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=U.S.+Food+%26+Drug+Administration&rft.atitle=FDA+Approved+Drugs&rft_id=https%3A%2F%2Fwww.accessdata.fda.gov%2Fscripts%2Fcder%2Fdaf%2Findex.cfm%3Fevent%3Doverview.process%26ApplNo%3D017388&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADydrogesterone" class="Z3988"> </li> <li id="cite_note-Drugs.com-101">^ <a href="#cite_ref-Drugs.com_101-0">a</a> <a href="#cite_ref-Drugs.com_101-1">b</a> <a href="#cite_ref-Drugs.com_101-2">c</a> <a href="#cite_ref-Drugs.com_101-3">d</a> <a href="#cite_ref-Drugs.com_101-4">e</a> <a href="#cite_ref-Drugs.com_101-5">f</a> <a rel="nofollow" class="external text" href="https://www.drugs.com/international/dydrogesterone.html">Dydrogesterone – Drugs.com</a> </li> <li id="cite_note-GöretzlehnerLauritzen2012-102"><a href="#cite_ref-GöretzlehnerLauritzen2012_102-0">^</a> <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=PA148">Praktische Hormontherapie in der Gynäkologie</a>. Walter de Gruyter. pp. 148–. <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=148-&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%3Fid%3DTIs2WhfYzZ4C%26pg%3DPA148&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADydrogesterone" class="Z3988"> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2>[<a href="/w/index.php?title=Dydrogesterone&action=edit&section=30" title="Edit section: Further reading">edit</a>]</div> <style data-mw-deduplicate="TemplateStyles:r1239549316">.mw-parser-output .refbegin{margin-bottom:0.5em}.mw-parser-output .refbegin-hanging-indents>ul{margin-left:0}.mw-parser-output .refbegin-hanging-indents>ul>li{margin-left:0;padding-left:3.2em;text-indent:-3.2em}.mw-parser-output .refbegin-hanging-indents ul,.mw-parser-output .refbegin-hanging-indents ul li{list-style:none}@media(max-width:720px){.mw-parser-output .refbegin-hanging-indents>ul>li{padding-left:1.6em;text-indent:-1.6em}}.mw-parser-output .refbegin-columns{margin-top:0.3em}.mw-parser-output .refbegin-columns ul{margin-top:0}.mw-parser-output .refbegin-columns li{page-break-inside:avoid;break-inside:avoid-column}@media screen{.mw-parser-output .refbegin{font-size:90%}}</style><div class="refbegin refbegin-columns references-column-width" style="column-width: 30em"> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFosterBalfour1997" class="citation journal cs1">Foster RH, Balfour JA (October 1997). "Estradiol and dydrogesterone. A review of their combined use as hormone replacement therapy in postmenopausal women". Drugs & Aging. 11 (4): 309–32. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.2165%2F00002512-199711040-00006">10.2165/00002512-199711040-00006</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/9342560">9342560</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:1733575">1733575</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Drugs+%26+Aging&rft.atitle=Estradiol+and+dydrogesterone.+A+review+of+their+combined+use+as+hormone+replacement+therapy+in+postmenopausal+women&rft.volume=11&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E309-%3C%2Fspan%3E32&rft.date=1997-10&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A1733575%23id-name%3DS2CID&rft_id=info%3Apmid%2F9342560&rft_id=info%3Adoi%2F10.2165%2F00002512-199711040-00006&rft.aulast=Foster&rft.aufirst=RH&rft.au=Balfour%2C+JA&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADydrogesterone" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFGruberHuber2005" class="citation journal cs1">Gruber CJ, Huber JC (December 2005). "The role of dydrogesterone in recurrent (habitual) abortion". The Journal of Steroid Biochemistry and Molecular Biology. 97 (5): 426–30. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.jsbmb.2005.08.009">10.1016/j.jsbmb.2005.08.009</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16188436">16188436</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:25237037">25237037</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Steroid+Biochemistry+and+Molecular+Biology&rft.atitle=The+role+of+dydrogesterone+in+recurrent+%28habitual%29+abortion&rft.volume=97&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E426-%3C%2Fspan%3E30&rft.date=2005-12&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A25237037%23id-name%3DS2CID&rft_id=info%3Apmid%2F16188436&rft_id=info%3Adoi%2F10.1016%2Fj.jsbmb.2005.08.009&rft.aulast=Gruber&rft.aufirst=CJ&rft.au=Huber%2C+JC&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADydrogesterone" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSeegerMueck2007" class="citation journal cs1">Seeger H, Mueck AO (October 2007). "Effects of dydrogesterone on the vascular system". Gynecological Endocrinology. 23 (Suppl 1): 2–8. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F09513590701584998">10.1080/09513590701584998</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/17943533">17943533</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:13380251">13380251</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Gynecological+Endocrinology&rft.atitle=Effects+of+dydrogesterone+on+the+vascular+system&rft.volume=23&rft.issue=Suppl+1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E2-%3C%2Fspan%3E8&rft.date=2007-10&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A13380251%23id-name%3DS2CID&rft_id=info%3Apmid%2F17943533&rft_id=info%3Adoi%2F10.1080%2F09513590701584998&rft.aulast=Seeger&rft.aufirst=H&rft.au=Mueck%2C+AO&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADydrogesterone" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSimonciniMannellaPluchinoGenazzani2007" class="citation journal cs1">Simoncini T, Mannella P, Pluchino N, Genazzani AR (October 2007). "Comparative effects of dydrogesterone and medroxyprogesterone acetate in critical areas: the brain and the vessels". 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Hormone Molecular Biology and Clinical Investigation. 27 (2): 49–53. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1515%2Fhmbci-2016-0028">10.1515/hmbci-2016-0028</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/27662647">27662647</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:23101112">23101112</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Hormone+Molecular+Biology+and+Clinical+Investigation&rft.atitle=Present+and+future+aspects+of+dydrogesterone+in+prevention+or+treatment+of+pregnancy+disorders%3A+an+outlook&rft.volume=27&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E49-%3C%2Fspan%3E53&rft.date=2016-08&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A23101112%23id-name%3DS2CID&rft_id=info%3Apmid%2F27662647&rft_id=info%3Adoi%2F10.1515%2Fhmbci-2016-0028&rft.aulast=Schindler&rft.aufirst=AE&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADydrogesterone" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLeeParkKimNorwitz2017" class="citation journal cs1">Lee HJ, Park TC, Kim JH, Norwitz E, Lee B (2017). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5748117">"The Influence of Oral Dydrogesterone and Vaginal Progesterone on Threatened Abortion: A Systematic Review and Meta-Analysis"</a>. BioMed Research International. 2017: 3616875. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1155%2F2017%2F3616875">10.1155/2017/3616875</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5748117">5748117</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/29392134">29392134</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=BioMed+Research+International&rft.atitle=The+Influence+of+Oral+Dydrogesterone+and+Vaginal+Progesterone+on+Threatened+Abortion%3A+A+Systematic+Review+and+Meta-Analysis&rft.volume=2017&rft.pages=3616875&rft.date=2017&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5748117%23id-name%3DPMC&rft_id=info%3Apmid%2F29392134&rft_id=info%3Adoi%2F10.1155%2F2017%2F3616875&rft.aulast=Lee&rft.aufirst=HJ&rft.au=Park%2C+TC&rft.au=Kim%2C+JH&rft.au=Norwitz%2C+E&rft.au=Lee%2C+B&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5748117&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADydrogesterone" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFGriesingerBlockeelTournaye2018" class="citation journal cs1">Griesinger G, Blockeel C, Tournaye H (May 2018). <a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.fertnstert.2018.03.034">"Oral dydrogesterone for luteal phase support in fresh in vitro fertilization cycles: a new standard?"</a>. Fertility and Sterility. 109 (5): 756–762. <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.fertnstert.2018.03.034">10.1016/j.fertnstert.2018.03.034</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/29778368">29778368</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Fertility+and+Sterility&rft.atitle=Oral+dydrogesterone+for+luteal+phase+support+in+fresh+in+vitro+fertilization+cycles%3A+a+new+standard%3F&rft.volume=109&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E756-%3C%2Fspan%3E762&rft.date=2018-05&rft_id=info%3Adoi%2F10.1016%2Fj.fertnstert.2018.03.034&rft_id=info%3Apmid%2F29778368&rft.aulast=Griesinger&rft.aufirst=G&rft.au=Blockeel%2C+C&rft.au=Tournaye%2C+H&rft_id=https%3A%2F%2Fdoi.org%2F10.1016%252Fj.fertnstert.2018.03.034&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADydrogesterone" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFGriesingerTournayeMacklonPetraglia2019" class="citation journal cs1">Griesinger G, Tournaye H, Macklon N, Petraglia F, Arck P, Blockeel C, et al. (February 2019). <a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.rbmo.2018.11.017">"Dydrogesterone: pharmacological profile and mechanism of action as luteal phase support in assisted reproduction"</a>. Reproductive Biomedicine Online. 38 (2): 249–259. <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.rbmo.2018.11.017">10.1016/j.rbmo.2018.11.017</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/30595525">30595525</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Reproductive+Biomedicine+Online&rft.atitle=Dydrogesterone%3A+pharmacological+profile+and+mechanism+of+action+as+luteal+phase+support+in+assisted+reproduction&rft.volume=38&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E249-%3C%2Fspan%3E259&rft.date=2019-02&rft_id=info%3Adoi%2F10.1016%2Fj.rbmo.2018.11.017&rft_id=info%3Apmid%2F30595525&rft.aulast=Griesinger&rft.aufirst=G&rft.au=Tournaye%2C+H&rft.au=Macklon%2C+N&rft.au=Petraglia%2C+F&rft.au=Arck%2C+P&rft.au=Blockeel%2C+C&rft.au=van+Amsterdam%2C+P&rft.au=Pexman-Fieth%2C+C&rft.au=Fauser%2C+BC&rft_id=https%3A%2F%2Fdoi.org%2F10.1016%252Fj.rbmo.2018.11.017&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADydrogesterone" class="Z3988"></li></ul> </div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><style data-mw-deduplicate="TemplateStyles:r1236075235">.mw-parser-output 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.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="Progestogens_and_antiprogestogens153" 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:Progestogens_and_antiprogestogens" title="Template:Progestogens and antiprogestogens"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Progestogens_and_antiprogestogens" title="Template talk:Progestogens and antiprogestogens"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Progestogens_and_antiprogestogens" title="Special:EditPage/Template:Progestogens and antiprogestogens"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Progestogens_and_antiprogestogens153" style="font-size:114%;margin:0 4em"><a href="/wiki/Progestogen_(medication)" title="Progestogen (medication)">Progestogens</a> and <a href="/wiki/Antiprogestogen" title="Antiprogestogen">antiprogestogens</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Progestogen_(medication)" title="Progestogen (medication)">Progestogens</a> (and <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestins</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="PRTooltip_Progesterone_receptor_agonists408" scope="row" class="navbox-group" style="width:8em;;text-align:center;"><a href="/wiki/Progesterone_receptor" title="Progesterone receptor"><abbr title="Progesterone receptor">PR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Progesterone receptor <a href="/wiki/Agonist" title="Agonist">agonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Progesterone derivatives: <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">Progesterone</a></li> <li><a href="/wiki/Quingestrone" title="Quingestrone">Quingestrone</a></li></ul> <ul><li>Retroprogesterone derivatives: <a class="mw-selflink selflink">Dydrogesterone</a></li> <li><a href="/wiki/Trengestone" title="Trengestone">Trengestone</a></li></ul> <ul><li>17α-Hydroxyprogesterone (and closely related) derivatives: 17α-Hydroxylated: <a href="/wiki/Acetomepregenol" title="Acetomepregenol">Acetomepregenol (mepregenol diacetate)</a></li> <li><a href="/wiki/Algestone_acetophenide" title="Algestone acetophenide">Algestone acetophenide (dihydroxyprogesterone acetophenide)</a></li> <li><a href="/wiki/Anagestone_acetate" title="Anagestone acetate">Anagestone acetate</a></li> <li><a href="/wiki/Chlormadinone_acetate" title="Chlormadinone acetate">Chlormadinone acetate</a></li> <li><a href="/wiki/Chlormethenmadinone_acetate" title="Chlormethenmadinone acetate">Chlormethenmadinone acetate</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Delmadinone_acetate" title="Delmadinone acetate">Delmadinone acetate</a></li> <li><a href="/wiki/Flugestone_acetate" title="Flugestone acetate">Flugestone acetate (flurogestone acetate)</a></li> <li><a href="/wiki/Flumedroxone_acetate" title="Flumedroxone acetate">Flumedroxone acetate</a></li> <li><a href="/wiki/Hydroxyprogesterone_acetate" title="Hydroxyprogesterone acetate">Hydroxyprogesterone acetate</a></li> <li><a href="/wiki/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">Hydroxyprogesterone caproate</a></li> <li><a href="/wiki/Hydroxyprogesterone_heptanoate" title="Hydroxyprogesterone heptanoate">Hydroxyprogesterone heptanoate</a></li> <li><a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">Medroxyprogesterone acetate</a>#</li> <li><a href="/wiki/Megestrol_acetate" title="Megestrol acetate">Megestrol acetate</a></li> <li><a href="/wiki/Melengestrol_acetate" title="Melengestrol acetate">Melengestrol acetate</a></li> <li><a href="/wiki/Methenmadinone_acetate" title="Methenmadinone acetate">Methenmadinone acetate</a></li> <li><a href="/wiki/Osaterone_acetate" title="Osaterone acetate">Osaterone acetate</a></li> <li><a href="/wiki/Pentagestrone_acetate" title="Pentagestrone acetate">Pentagestrone acetate</a></li> <li><a href="/wiki/Proligestone" title="Proligestone">Proligestone</a>; 17α-Methylated: <a href="/wiki/Medrogestone" title="Medrogestone">Medrogestone</a>; Others: <a href="/wiki/Haloprogesterone" title="Haloprogesterone">Haloprogesterone</a></li></ul> <ul><li>19-Norprogesterone derivatives: 17α-Hydroxylated: <a href="/wiki/Gestonorone_caproate" title="Gestonorone caproate">Gestonorone caproate (gestronol hexanoate)</a></li> <li><a href="/wiki/Nomegestrol_acetate" title="Nomegestrol acetate">Nomegestrol acetate</a></li> <li><a href="/wiki/Norgestomet" title="Norgestomet">Norgestomet</a></li> <li><a href="/wiki/Segesterone_acetate" title="Segesterone acetate">Segesterone acetate (nestorone, elcometrine)</a>; 17α-Methylated: <a href="/wiki/Demegestone" title="Demegestone">Demegestone</a></li> <li><a href="/wiki/Promegestone" title="Promegestone">Promegestone</a></li> <li><a href="/wiki/Trimegestone" title="Trimegestone">Trimegestone</a></li></ul> <ul><li>Testosterone derivatives: Estranes: <a href="/wiki/Danazol" title="Danazol">Danazol</a></li> <li><a href="/wiki/Dimethisterone" title="Dimethisterone">Dimethisterone</a></li> <li><a href="/wiki/Ethisterone" title="Ethisterone">Ethisterone</a></li></ul> <ul><li>19-Nortestosterone derivatives: Estranes: <a href="/wiki/Allylestrenol" title="Allylestrenol">Allylestrenol</a></li> <li><a href="/wiki/Altrenogest" title="Altrenogest">Altrenogest</a></li> <li><a href="/wiki/Dienogest" title="Dienogest">Dienogest</a></li> <li><a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">Etynodiol diacetate</a></li> <li><a href="/wiki/Lynestrenol" title="Lynestrenol">Lynestrenol</a></li> <li><a href="/wiki/Norethisterone" title="Norethisterone">Norethisterone (norethindrone)</a>#</li> <li><a href="/wiki/Norethisterone_acetate" title="Norethisterone acetate">Norethisterone acetate</a></li> <li><a href="/wiki/Norethisterone_enanthate" title="Norethisterone enanthate">Norethisterone enanthate</a></li> <li><a href="/wiki/Noretynodrel" title="Noretynodrel">Noretynodrel</a></li> <li><a href="/wiki/Norgesterone" title="Norgesterone">Norgesterone</a></li> <li><a href="/wiki/Norgestrienone" title="Norgestrienone">Norgestrienone</a></li> <li><a href="/wiki/Normethandrone" title="Normethandrone">Normethandrone (methylestrenolone)</a></li> <li><a href="/wiki/Norvinisterone" title="Norvinisterone">Norvinisterone</a></li> <li><a href="/wiki/Oxendolone" title="Oxendolone">Oxendolone</a></li> <li><a href="/wiki/Quingestanol_acetate" title="Quingestanol acetate">Quingestanol acetate</a></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a>; Gonanes: <a href="/wiki/Desogestrel" title="Desogestrel">Desogestrel</a></li> <li><a href="/wiki/Etonogestrel" title="Etonogestrel">Etonogestrel</a></li> <li><a href="/wiki/Gestodene" title="Gestodene">Gestodene</a></li> <li><a href="/wiki/Gestrinone" title="Gestrinone">Gestrinone</a></li> <li><a href="/wiki/Levonorgestrel" title="Levonorgestrel">Levonorgestrel</a>#</li> <li><a href="/wiki/Norelgestromin" title="Norelgestromin">Norelgestromin</a></li> <li><a href="/wiki/Norgestimate" title="Norgestimate">Norgestimate</a></li> <li><a href="/wiki/Norgestrel" title="Norgestrel">Norgestrel</a></li></ul> <ul><li>Spirolactone derivatives: <a href="/wiki/Drospirenone" title="Drospirenone">Drospirenone</a></li></ul> <ul><li>Others: <a href="/wiki/Anabolic%E2%80%93androgenic_steroid" class="mw-redirect" title="Anabolic–androgenic steroid">Anabolic–androgenic steroids</a> (e.g., <a href="/wiki/Nandrolone" title="Nandrolone">nandrolone</a> and <a href="/wiki/Nandrolone_ester" class="mw-redirect" title="Nandrolone ester">esters</a>, <a href="/wiki/Trenbolone" title="Trenbolone">trenbolone</a> and <a href="/wiki/Trenbolone_ester" class="mw-redirect" title="Trenbolone ester">esters</a>, <a href="/wiki/Ethylestrenol" title="Ethylestrenol">ethylestrenol</a>, <a href="/wiki/Norethandrolone" title="Norethandrolone">norethandrolone</a>, others)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Antiprogestogen" title="Antiprogestogen">Antiprogestogens</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8em;;text-align:center;"><a href="/wiki/Selective_progesterone_receptor_modulators" class="mw-redirect" title="Selective progesterone receptor modulators"><abbr title="Selective progesterone receptor modulators">SPRMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Selective progesterone receptor modulators</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Telapristone" title="Telapristone">Telapristone</a>§</li> <li><a href="/wiki/Ulipristal_acetate" title="Ulipristal acetate">Ulipristal acetate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8em;;text-align:center;"><a href="/wiki/Progesterone_receptor" title="Progesterone receptor"><abbr title="Progesterone receptor">PR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Progesterone receptor <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aglepristone" title="Aglepristone">Aglepristone</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td colspan="2" class="navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><div class="hlist"> <ul><li>#<a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li>‡<a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li>†<a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li>§Never to phase III</li></ul></li></ul> </div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Progesterone_receptor_modulators" title="Template:Progesterone receptor modulators">Progesterone receptor modulators</a></dd> <dd><a href="/wiki/Template:Androgens_and_antiandrogens" title="Template:Androgens and antiandrogens">Androgens and antiandrogens</a></dd> <dd><a href="/wiki/Template:Estrogens_and_antiestrogens" title="Template:Estrogens and antiestrogens">Estrogens and antiestrogens</a></dd> <dd><a href="/wiki/List_of_steroidal_progestogens" class="mw-redirect" title="List of steroidal progestogens">List of progestogens</a></dd></dl></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Progesterone_receptor_modulators1654" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Progesterone_receptor_modulators" title="Template:Progesterone receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Progesterone_receptor_modulators" title="Template talk:Progesterone receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Progesterone_receptor_modulators" title="Special:EditPage/Template:Progesterone receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Progesterone_receptor_modulators1654" style="font-size:114%;margin:0 4em"><a href="/wiki/Progesterone_receptor" title="Progesterone receptor">Progesterone receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Progesterone_receptor" title="Progesterone receptor"><abbr title="Progesterone receptor">PR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Progesterone receptor</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Progesterone derivatives: <a href="/wiki/3%CE%B2-Dihydroprogesterone" title="3β-Dihydroprogesterone">3β-Dihydroprogesterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">5α-Dihydroprogesterone</a></li> <li><a href="/wiki/6%CE%B1-Methylprogesterone" title="6α-Methylprogesterone">6α-Methylprogesterone</a></li> <li><a href="/wiki/9%CE%B1-Bromo-11-ketoprogesterone" class="mw-redirect" title="9α-Bromo-11-ketoprogesterone">9α-Bromo-11-ketoprogesterone</a></li> <li><a href="/wiki/11-Dehydroprogesterone" title="11-Dehydroprogesterone">11-Dehydroprogesterone</a></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyprogesterone" title="16α-Hydroxyprogesterone">16α-Hydroxyprogesterone</a></li> <li><a href="/w/index.php?title=17%CE%B1-Methyl-11-deoxycorticosterone_acetate&action=edit&redlink=1" class="new" title="17α-Methyl-11-deoxycorticosterone acetate (page does not exist)">17α-Methyl-11-deoxycorticosterone acetate</a></li> <li><a href="/wiki/20%CE%B1-Dihydroprogesterone" title="20α-Dihydroprogesterone">20α-Dihydroprogesterone</a></li> <li><a href="/wiki/20%CE%B2-Dihydroprogesterone" title="20β-Dihydroprogesterone">20β-Dihydroprogesterone</a></li> <li><a href="/wiki/Dimepregnen" title="Dimepregnen">Dimepregnen</a></li> <li><a href="/wiki/Diosgenin" title="Diosgenin">Diosgenin</a></li> <li><a href="/wiki/P1-185" title="P1-185">P1-185</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Progesterone_3-acetyl_enol_ether" title="Progesterone 3-acetyl enol ether">Progesterone 3-acetyl enol ether</a></li> <li><a href="/wiki/Quingestrone" title="Quingestrone">Quingestrone</a></li></ul> <ul><li>Retroprogesterone derivatives: <a href="/wiki/20%CE%B1-Dihydrodydrogesterone" title="20α-Dihydrodydrogesterone">20α-Dihydrodydrogesterone</a></li> <li><a href="/wiki/20%CE%B1-Dihydrotrengestone" title="20α-Dihydrotrengestone">20α-Dihydrotrengestone</a></li> <li><a href="/wiki/DU-41164" title="DU-41164">DU-41164</a></li> <li><a href="/wiki/DU-41165" title="DU-41165">DU-41165</a></li> <li><a class="mw-selflink selflink">Dydrogesterone</a></li> <li><a href="/wiki/Retroprogesterone" title="Retroprogesterone">Retroprogesterone</a></li> <li><a href="/wiki/Ro_6-3129" title="Ro 6-3129">Ro 6-3129</a></li> <li><a href="/wiki/Trengestone" title="Trengestone">Trengestone</a></li></ul> <ul><li>17α-Substituted progesterone derivatives: <a href="/wiki/6%CE%B1-Methyl-17%CE%B1-bromoprogesterone" title="6α-Methyl-17α-bromoprogesterone">6α-Methyl-17α-bromoprogesterone</a></li> <li><a href="/wiki/15%CE%B2-Hydroxycyproterone_acetate" title="15β-Hydroxycyproterone acetate">15β-Hydroxycyproterone acetate</a></li> <li><a href="/wiki/16-Methylene-17%CE%B1-hydroxyprogesterone_acetate" title="16-Methylene-17α-hydroxyprogesterone acetate">16-Methylene-17α-hydroxyprogesterone acetate</a></li> <li><a href="/wiki/17%CE%B1-Bromoprogesterone" title="17α-Bromoprogesterone">17α-Bromoprogesterone</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone (hydroxyprogesterone)</a></li> <li><a href="/wiki/17%CE%B1-Methylprogesterone" title="17α-Methylprogesterone">17α-Methylprogesterone</a></li> <li><a href="/wiki/Acetomepregenol" title="Acetomepregenol">Acetomepregenol (mepregenol diacetate)</a></li> <li><a href="/wiki/Algestone" title="Algestone">Algestone</a></li> <li><a href="/wiki/Algestone_acetonide" title="Algestone acetonide">Algestone acetonide</a></li> <li><a href="/wiki/Algestone_acetophenide" title="Algestone acetophenide">Algestone acetophenide</a></li> <li><a href="/wiki/Anagestone" title="Anagestone">Anagestone</a></li> <li><a href="/wiki/Anagestone_acetate" title="Anagestone acetate">Anagestone acetate</a></li> <li><a href="/w/index.php?title=Bromethenmadinone&action=edit&redlink=1" class="new" title="Bromethenmadinone (page does not exist)">Bromethenmadinone</a></li> <li><a href="/wiki/Bromethenmadinone_acetate" title="Bromethenmadinone acetate">Bromethenmadinone acetate</a></li> <li><a href="/wiki/Butagest" title="Butagest">Butagest (buterol)</a></li> <li><a href="/wiki/Chlormadinone" title="Chlormadinone">Chlormadinone</a></li> <li><a href="/wiki/Chlormadinone_acetate" title="Chlormadinone acetate">Chlormadinone acetate</a></li> <li><a href="/wiki/Chlormadinone_caproate" title="Chlormadinone caproate">Chlormadinone caproate</a></li> <li><a href="/w/index.php?title=Chlormethenmadinone&action=edit&redlink=1" class="new" title="Chlormethenmadinone (page does not exist)">Chlormethenmadinone</a></li> <li><a href="/wiki/Chlormethenmadinone_acetate" title="Chlormethenmadinone acetate">Chlormethenmadinone acetate</a></li> <li><a href="/wiki/Cismadinone" title="Cismadinone">Cismadinone</a></li> <li><a href="/wiki/Cismadinone_acetate" title="Cismadinone acetate">Cismadinone acetate</a></li> <li><a href="/wiki/Clogestone" title="Clogestone">Clogestone</a></li> <li><a href="/wiki/Clogestone_acetate" title="Clogestone acetate">Clogestone acetate</a></li> <li><a href="/wiki/Clomegestone" title="Clomegestone">Clomegestone</a></li> <li><a href="/wiki/Clomegestone_acetate" title="Clomegestone acetate">Clomegestone acetate</a></li> <li><a href="/wiki/Cymegesolate" title="Cymegesolate">Cymegesolate</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Delmadinone" title="Delmadinone">Delmadinone</a></li> <li><a href="/wiki/Delmadinone_acetate" title="Delmadinone acetate">Delmadinone acetate</a></li> <li><a href="/wiki/Edogestrone" title="Edogestrone">Edogestrone</a></li> <li><a href="/wiki/Flugestone" title="Flugestone">Flugestone</a></li> <li><a href="/wiki/Flugestone_acetate" title="Flugestone acetate">Flugestone acetate</a></li> <li><a href="/wiki/Fluorometholone" title="Fluorometholone">Fluorometholone</a></li> <li><a href="/wiki/Fluorometholone_acetate" title="Fluorometholone acetate">Fluorometholone acetate</a></li> <li><a href="/wiki/Flumedroxone" title="Flumedroxone">Flumedroxone</a></li> <li><a href="/wiki/Flumedroxone_acetate" title="Flumedroxone acetate">Flumedroxone acetate</a></li> <li><a href="/wiki/Fluoromedroxyprogesterone_acetate" title="Fluoromedroxyprogesterone acetate">Fluoromedroxyprogesterone acetate</a></li> <li><a href="/wiki/Gestaclone" title="Gestaclone">Gestaclone</a></li> <li><a href="/w/index.php?title=Gestobutanoyl&action=edit&redlink=1" class="new" title="Gestobutanoyl (page does not exist)">Gestobutanoyl</a></li> <li><a href="/wiki/Haloprogesterone" title="Haloprogesterone">Haloprogesterone</a></li> <li><a href="/wiki/Hydromadinone" title="Hydromadinone">Hydromadinone</a></li> <li><a href="/wiki/Hydromadinone_acetate" title="Hydromadinone acetate">Hydromadinone acetate</a></li> <li><a href="/wiki/Hydroxyprogesterone_acetate" title="Hydroxyprogesterone acetate">Hydroxyprogesterone acetate</a></li> <li><a href="/wiki/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">Hydroxyprogesterone caproate (hydroxyprogesterone hexanoate)</a></li> <li><a href="/wiki/Hydroxyprogesterone_heptanoate" title="Hydroxyprogesterone heptanoate">Hydroxyprogesterone heptanoate (hydroxyprogesterone enanthate)</a></li> <li><a href="/wiki/Hydroxyprogesterone_heptanoate_benzilic_acid_hydrazone" title="Hydroxyprogesterone heptanoate benzilic acid hydrazone">Hydroxyprogesterone heptanoate benzilic acid hydrazone</a></li> <li><a href="/wiki/Mecigestone" title="Mecigestone">Mecigestone (pentarane B)</a></li> <li><a href="/wiki/Medrogestone" title="Medrogestone">Medrogestone</a></li> <li><a href="/wiki/Medroxyprogesterone" title="Medroxyprogesterone">Medroxyprogesterone</a></li> <li><a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">Medroxyprogesterone acetate</a></li> <li><a href="/wiki/Medroxyprogesterone_caproate" title="Medroxyprogesterone caproate">Medroxyprogesterone caproate</a></li> <li><a href="/wiki/Megestrol" title="Megestrol">Megestrol</a></li> <li><a href="/wiki/Megestrol_acetate" title="Megestrol acetate">Megestrol acetate</a></li> <li><a href="/wiki/Megestrol_caproate" title="Megestrol caproate">Megestrol caproate</a></li> <li><a href="/wiki/Melengestrol" title="Melengestrol">Melengestrol</a></li> <li><a href="/wiki/Melengestrol_acetate" title="Melengestrol acetate">Melengestrol acetate</a></li> <li><a href="/wiki/Methenmadinone" title="Methenmadinone">Methenmadinone</a></li> <li><a href="/wiki/Methenmadinone_acetate" title="Methenmadinone acetate">Methenmadinone acetate</a></li> <li><a href="/wiki/Methenmadinone_caproate" title="Methenmadinone caproate">Methenmadinone caproate</a></li> <li><a href="/wiki/Mometasone" title="Mometasone">Mometasone</a></li> <li><a href="/wiki/Mometasone_furoate" class="mw-redirect" title="Mometasone furoate">Mometasone furoate</a></li> <li><a href="/wiki/Osaterone" title="Osaterone">Osaterone</a></li> <li><a href="/wiki/Osaterone_acetate" title="Osaterone acetate">Osaterone acetate</a></li> <li><a href="/wiki/Pentagestrone" title="Pentagestrone">Pentagestrone</a></li> <li><a href="/wiki/Pentagestrone_acetate" title="Pentagestrone acetate">Pentagestrone acetate</a></li> <li><a href="/wiki/Pentarane_A" title="Pentarane A">Pentarane A</a></li> <li><a href="/wiki/Proligestone" title="Proligestone">Proligestone</a></li> <li><a href="/wiki/Triamcinolone_acetonide" title="Triamcinolone acetonide">Triamcinolone acetonide</a></li></ul> <ul><li>19-Norprogesterone derivatives: <a href="/wiki/17%CE%B1-Methyl-19-norprogesterone" title="17α-Methyl-19-norprogesterone">17α-Methyl-19-norprogesterone</a></li> <li><a href="/wiki/18-Methylsegesterone_acetate" title="18-Methylsegesterone acetate">18-Methylsegesterone acetate</a></li> <li><a href="/wiki/19-Norprogesterone" title="19-Norprogesterone">19-Norprogesterone</a></li> <li><a href="/wiki/Amadinone" title="Amadinone">Amadinone</a></li> <li><a href="/wiki/Amadinone_acetate" title="Amadinone acetate">Amadinone acetate</a></li> <li><a href="/wiki/Demegestone" title="Demegestone">Demegestone</a></li> <li><a href="/w/index.php?title=Fluoro_ethyl_norprogesterone&action=edit&redlink=1" class="new" title="Fluoro ethyl norprogesterone (page does not exist)">Fluoro ethyl norprogesterone</a></li> <li><a href="/w/index.php?title=Fluoro_furanyl_norprogesterone&action=edit&redlink=1" class="new" title="Fluoro furanyl norprogesterone (page does not exist)">Fluoro furanyl norprogesterone</a></li> <li><a href="/wiki/Gestadienol" title="Gestadienol">Gestadienol</a></li> <li><a href="/wiki/Gestadienol_acetate" title="Gestadienol acetate">Gestadienol acetate</a></li> <li><a href="/wiki/Gestonorone_acetate" title="Gestonorone acetate">Gestonorone acetate (gestronol acetate)</a></li> <li><a href="/wiki/Gestonorone_caproate" title="Gestonorone caproate">Gestonorone caproate (gestronol hexanoate)</a></li> <li><a href="/wiki/Gestronol" title="Gestronol">Gestronol (gestonorone)</a></li> <li><a href="/wiki/Nomegestrol" title="Nomegestrol">Nomegestrol</a></li> <li><a href="/wiki/Nomegestrol_acetate" title="Nomegestrol acetate">Nomegestrol acetate</a></li> <li><a href="/wiki/Norgestomet" title="Norgestomet">Norgestomet</a></li> <li><a href="/wiki/ORG-2058" title="ORG-2058">ORG-2058</a></li> <li><a href="/wiki/Oxogestone" title="Oxogestone">Oxogestone</a></li> <li><a href="/wiki/Oxogestone_phenpropionate" title="Oxogestone phenpropionate">Oxogestone phenpropionate (xinogestone)</a></li> <li><a href="/wiki/Promegestone" title="Promegestone">Promegestone</a></li> <li><a href="/wiki/Segesterone" title="Segesterone">Segesterone</a></li> <li><a href="/wiki/Nestorone" class="mw-redirect" title="Nestorone">Segesterone acetate (nestorone)</a></li> <li><a href="/wiki/Trimegestone" title="Trimegestone">Trimegestone</a></li></ul> <ul><li>Testosterone derivatives: Progestins: <a href="/wiki/6,6-Difluoronorethisterone" title="6,6-Difluoronorethisterone">6,6-Difluoronorethisterone</a></li> <li><a href="/wiki/6,6-Difluoronorethisterone_acetate" title="6,6-Difluoronorethisterone acetate">6,6-Difluoronorethisterone acetate</a></li> <li><a href="/wiki/17%CE%B1-Allyl-19-nortestosterone" title="17α-Allyl-19-nortestosterone">17α-Allyl-19-nortestosterone</a></li> <li><a href="/wiki/Allylestrenol" title="Allylestrenol">Allylestrenol</a></li> <li><a href="/wiki/Altrenogest" title="Altrenogest">Altrenogest</a></li> <li><a href="/wiki/Chloroethynylnorgestrel" title="Chloroethynylnorgestrel">Chloroethynylnorgestrel</a></li> <li><a href="/wiki/Cingestol" title="Cingestol">Cingestol</a></li> <li><a href="/wiki/Danazol" title="Danazol">Danazol</a></li> <li><a href="/wiki/Desogestrel" title="Desogestrel">Desogestrel</a></li> <li><a href="/wiki/Dienogest" title="Dienogest">Dienogest</a></li> <li><a href="/wiki/Ethinylandrostenediol" title="Ethinylandrostenediol">Ethinylandrostenediol</a> <ul><li><a href="/wiki/Ethandrostate" title="Ethandrostate">Ethandrostate</a></li></ul></li> <li><a href="/wiki/Ethisterone" title="Ethisterone">Ethisterone</a></li> <li><a href="/wiki/Ethynerone" title="Ethynerone">Ethynerone</a></li> <li><a href="/wiki/Etonogestrel" title="Etonogestrel">Etonogestrel</a></li> <li><a href="/wiki/Etynodiol" title="Etynodiol">Etynodiol</a></li> <li><a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">Etynodiol diacetate</a></li> <li><a href="/wiki/Gestodene" title="Gestodene">Gestodene</a></li> <li><a href="/wiki/Gestrinone" title="Gestrinone">Gestrinone</a></li> <li><a href="/wiki/Levonorgestrel" title="Levonorgestrel">Levonorgestrel</a></li> <li><a href="/wiki/Levonorgestrel_ester" class="mw-redirect" title="Levonorgestrel ester">Levonorgestrel esters</a> (e.g., <a href="/wiki/Levonorgestrel_butanoate" title="Levonorgestrel butanoate">levonorgestrel butanoate</a>)</li> <li><a href="/wiki/Lynestrenol" title="Lynestrenol">Lynestrenol</a></li> <li><a href="/wiki/Lynestrenol_phenylpropionate" title="Lynestrenol phenylpropionate">Lynestrenol phenylpropionate</a></li> <li><a href="/wiki/Metynodiol" title="Metynodiol">Metynodiol</a></li> <li><a href="/wiki/Metynodiol_diacetate" title="Metynodiol diacetate">Metynodiol diacetate</a></li> <li><a href="/wiki/Norelgestromin" title="Norelgestromin">Norelgestromin</a></li> <li><a href="/wiki/Norethisterone" title="Norethisterone">Norethisterone (norethindrone)</a></li> <li><a href="/wiki/Norethisterone_ester" class="mw-redirect" title="Norethisterone ester">Norethisterone esters</a> (e.g., <a href="/wiki/Norethisterone_acetate" title="Norethisterone acetate">norethisterone acetate</a>, <a href="/wiki/Norethisterone_enanthate" title="Norethisterone enanthate">norethisterone enanthate</a>)</li> <li><a href="/wiki/Noretynodrel" title="Noretynodrel">Noretynodrel</a></li> <li><a href="/wiki/Norgesterone" title="Norgesterone">Norgesterone</a></li> <li><a href="/wiki/Norgestimate" title="Norgestimate">Norgestimate</a></li> <li><a href="/wiki/Norgestrel" title="Norgestrel">Norgestrel</a></li> <li><a href="/wiki/Norgestrienone" title="Norgestrienone">Norgestrienone</a></li> <li><a href="/wiki/Norvinisterone" title="Norvinisterone">Norvinisterone</a></li> <li><a href="/wiki/Oxendolone" title="Oxendolone">Oxendolone</a></li> <li><a href="/wiki/Quingestanol" title="Quingestanol">Quingestanol</a></li> <li><a href="/wiki/Quingestanol_acetate" title="Quingestanol acetate">Quingestanol acetate</a></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li> <li><a href="/wiki/Tigestol" title="Tigestol">Tigestol</a></li> <li><a href="/wiki/Tosagestin" title="Tosagestin">Tosagestin</a>; Anabolic–androgenic steroids: <a href="/wiki/11%CE%B2-Methyl-19-nortestosterone" title="11β-Methyl-19-nortestosterone">11β-Methyl-19-nortestosterone</a></li> <li><a href="/wiki/11%CE%B2-Methyl-19-nortestosterone_dodecylcarbonate" title="11β-Methyl-19-nortestosterone dodecylcarbonate">11β-Methyl-19-nortestosterone dodecylcarbonate</a></li> <li><a href="/wiki/19-Nor-5-androstenediol" title="19-Nor-5-androstenediol">19-Nor-5-androstenediol</a></li> <li><a href="/wiki/19-Nor-5-androstenedione" title="19-Nor-5-androstenedione">19-Nor-5-androstenedione</a></li> <li><a href="/wiki/19-Nordehydroepiandrosterone" title="19-Nordehydroepiandrosterone">19-Nordehydroepiandrosterone</a></li> <li><a href="/wiki/Bolandiol" title="Bolandiol">Bolandiol</a></li> <li><a href="/wiki/Bolandiol_dipropionate" title="Bolandiol dipropionate">Bolandiol dipropionate</a></li> <li><a href="/wiki/Bolandione" title="Bolandione">Bolandione</a></li> <li><a href="/wiki/Dimethisterone" title="Dimethisterone">Dimethisterone</a></li> <li><a href="/wiki/Dienedione" title="Dienedione">Dienedione</a></li> <li><a href="/wiki/Dienolone" title="Dienolone">Dienolone</a></li> <li><a href="/wiki/Dimethandrolone" title="Dimethandrolone">Dimethandrolone</a></li> <li><a href="/wiki/Dimethandrolone_buciclate" title="Dimethandrolone buciclate">Dimethandrolone buciclate</a></li> <li><a href="/wiki/Dimethandrolone_dodecylcarbonate" title="Dimethandrolone dodecylcarbonate">Dimethandrolone dodecylcarbonate</a></li> <li><a href="/wiki/Dimethandrolone_undecanoate" title="Dimethandrolone undecanoate">Dimethandrolone undecanoate</a></li> <li><a href="/wiki/Dimethyldienolone" title="Dimethyldienolone">Dimethyldienolone</a></li> <li><a href="/wiki/Dimethyltrienolone" title="Dimethyltrienolone">Dimethyltrienolone</a></li> <li><a href="/wiki/Ethyldienolone" title="Ethyldienolone">Ethyldienolone</a></li> <li><a href="/wiki/Ethylestrenol" title="Ethylestrenol">Ethylestrenol (ethylnandrol)</a></li> <li><a href="/wiki/Methyldienolone" title="Methyldienolone">Methyldienolone</a></li> <li><a href="/wiki/Metribolone" title="Metribolone">Metribolone (R-1881)</a></li> <li><a href="/wiki/Methoxydienone" title="Methoxydienone">Methoxydienone (methoxygonadiene)</a></li> <li><a href="/wiki/Mibolerone" title="Mibolerone">Mibolerone</a></li> <li><a href="/wiki/Nandrolone" title="Nandrolone">Nandrolone</a></li> <li><a href="/wiki/Nandrolone_ester" class="mw-redirect" title="Nandrolone ester">Nandrolone esters</a> (e.g., <a href="/wiki/Nandrolone_decanoate" title="Nandrolone decanoate">nandrolone decanoate</a>, <a href="/wiki/Nandrolone_phenylpropionate" title="Nandrolone phenylpropionate">nandrolone phenylpropionate</a>)</li> <li><a href="/wiki/Norethandrolone" title="Norethandrolone">Norethandrolone</a></li> <li><a href="/wiki/Normethandrone" title="Normethandrone">Normethandrone (methylestrenolone, normethandrolone, normethisterone)</a></li> <li><a href="/wiki/RU-2309" title="RU-2309">RU-2309</a></li> <li><a href="/wiki/Tetrahydrogestrinone" title="Tetrahydrogestrinone">Tetrahydrogestrinone</a></li> <li><a href="/wiki/Trenbolone" title="Trenbolone">Trenbolone (trienolone)</a></li> <li><a href="/wiki/Trenbolone_ester" class="mw-redirect" title="Trenbolone ester">Trenbolone esters</a> (e.g., <a href="/wiki/Trenbolone_acetate" title="Trenbolone acetate">trenbolone acetate</a>, <a href="/wiki/Trenbolone_enanthate" title="Trenbolone enanthate">trenbolone enanthate</a>)</li> <li><a href="/wiki/Trendione" title="Trendione">Trendione</a></li> <li><a href="/wiki/Trestolone" title="Trestolone">Trestolone</a></li> <li><a href="/wiki/Trestolone_acetate" title="Trestolone acetate">Trestolone acetate</a></li></ul> <ul><li>Spirolactone derivatives: <a href="/wiki/Canrenoic_acid" title="Canrenoic acid">Canrenoic acid</a></li> <li><a href="/wiki/Canrenone" title="Canrenone">Canrenone</a></li> <li><a href="/wiki/Drospirenone" title="Drospirenone">Drospirenone</a></li> <li><a href="/wiki/Mespirenone" title="Mespirenone">Mespirenone</a></li> <li><a href="/wiki/Potassium_canrenoate" title="Potassium canrenoate">Potassium canrenoate</a></li> <li><a href="/wiki/Prorenone" title="Prorenone">Prorenone</a></li> <li><a href="/wiki/SC-5233" title="SC-5233">SC-5233 (spirolactone)</a></li> <li><a href="/wiki/SC-8109" title="SC-8109">SC-8109</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/wiki/Spirorenone" title="Spirorenone">Spirorenone</a></li></ul> <ul><li>Nonsteroidal: <a href="/wiki/3,8-Dihydrodiligustilide" title="3,8-Dihydrodiligustilide">3,8-Dihydrodiligustilide</a></li> <li><a href="/wiki/LG-2527" title="LG-2527">LG-2527</a></li> <li><a href="/w/index.php?title=LG-100128&action=edit&redlink=1" class="new" title="LG-100128 (page does not exist)">LG-100128</a></li> <li><a href="/wiki/Riligustilide" title="Riligustilide">Riligustilide</a></li> <li><a href="/w/index.php?title=RWJ-26819&action=edit&redlink=1" class="new" title="RWJ-26819 (page does not exist)">RWJ-26819</a></li> <li><a href="/w/index.php?title=RWJ-49853&action=edit&redlink=1" class="new" title="RWJ-49853 (page does not exist)">RWJ-49853</a></li> <li><a href="/w/index.php?title=RWJ-60130&action=edit&redlink=1" class="new" title="RWJ-60130 (page does not exist)">RWJ-60130</a></li> <li><a href="/wiki/Tanaproget" title="Tanaproget">Tanaproget</a></li> <li><a href="/wiki/ZM-182345" title="ZM-182345">ZM-182345</a></li></ul> <ul><li>Unknown: <a href="/wiki/ORG-47241" title="ORG-47241">ORG-47241</a></li> <li><a href="/wiki/ORG-201745" title="ORG-201745">ORG-201745</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Mixed (<a href="/wiki/Selective_progesterone_receptor_modulators" class="mw-redirect" title="Selective progesterone receptor modulators"><abbr title="Selective progesterone receptor modulators">SPRMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Selective progesterone receptor modulators)</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Steroidal: <a href="/wiki/Dihydroethisterone" class="mw-redirect" title="Dihydroethisterone">Dihydroethisterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydrolevonorgestrel" title="5α-Dihydrolevonorgestrel">5α-Dihydrolevonorgestrel</a></li> <li><a href="/wiki/5%CE%B1-Dihydronorethisterone" title="5α-Dihydronorethisterone">5α-Dihydronorethisterone</a></li> <li><a href="/wiki/Asoprisnil" title="Asoprisnil">Asoprisnil</a></li> <li><a href="/wiki/Asoprisnil_ecamate" title="Asoprisnil ecamate">Asoprisnil ecamate</a></li> <li><a href="/wiki/Guggulsterone" title="Guggulsterone">Guggulsterone</a></li> <li><a href="/w/index.php?title=J1042&action=edit&redlink=1" class="new" title="J1042 (page does not exist)">J1042</a></li> <li><a href="/w/index.php?title=LG-120838&action=edit&redlink=1" class="new" title="LG-120838 (page does not exist)">LG-120838</a></li> <li><a href="/wiki/Metapristone" title="Metapristone">Metapristone (RU-42633)</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone (RU-486)</a></li> <li><a href="/w/index.php?title=ORF-9371&action=edit&redlink=1" class="new" title="ORF-9371 (page does not exist)">ORF-9371</a></li> <li><a href="/wiki/ORF-9326" class="mw-redirect" title="ORF-9326">ORF-9326</a></li> <li><a href="/w/index.php?title=ORG-31710&action=edit&redlink=1" class="new" title="ORG-31710 (page does not exist)">ORG-31710</a></li> <li><a href="/w/index.php?title=ORG-33628&action=edit&redlink=1" class="new" title="ORG-33628 (page does not exist)">ORG-33628</a></li> <li><a href="/w/index.php?title=RMI-12936&action=edit&redlink=1" class="new" title="RMI-12936 (page does not exist)">RMI-12936</a></li> <li><a href="/wiki/Telapristone" title="Telapristone">Telapristone</a></li> <li><a href="/wiki/Ulipristal_acetate" title="Ulipristal acetate">Ulipristal acetate</a></li> <li><a href="/wiki/Vilaprisan" title="Vilaprisan">Vilaprisan</a></li> <li><a href="/w/index.php?title=ZK-137316&action=edit&redlink=1" class="new" title="ZK-137316 (page does not exist)">ZK-137316</a></li></ul> <ul><li>Nonsteroidal: <a href="/wiki/Apigenin" title="Apigenin">Apigenin</a></li> <li><a href="/wiki/Kaempferol" title="Kaempferol">Kaempferol</a></li> <li><a href="/w/index.php?title=LG-120920&action=edit&redlink=1" class="new" title="LG-120920 (page does not exist)">LG-120920</a></li> <li><a href="/wiki/Naringenin" title="Naringenin">Naringenin</a></li> <li><a href="/w/index.php?title=PRA-910&action=edit&redlink=1" class="new" title="PRA-910 (page does not exist)">PRA-910</a></li> <li><a href="/wiki/Syringic_acid" title="Syringic acid">Syringic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Steroidal: <a href="/wiki/Aglepristone" title="Aglepristone">Aglepristone</a></li> <li><a href="/wiki/Lilopristone" title="Lilopristone">Lilopristone</a></li> <li><a href="/wiki/Lonaprisan" title="Lonaprisan">Lonaprisan</a></li> <li><a href="/wiki/Onapristone" title="Onapristone">Onapristone</a></li> <li><a href="/w/index.php?title=ORG-31710&action=edit&redlink=1" class="new" title="ORG-31710 (page does not exist)">ORG-31710</a></li> <li><a href="/w/index.php?title=ORG-31806&action=edit&redlink=1" class="new" title="ORG-31806 (page does not exist)">ORG-31806</a></li> <li><a href="/w/index.php?title=ORG-33628&action=edit&redlink=1" class="new" title="ORG-33628 (page does not exist)">ORG-33628</a></li> <li><a href="/w/index.php?title=RTI_3021%E2%80%93022&action=edit&redlink=1" class="new" title="RTI 3021–022 (page does not exist)">RTI 3021–022</a></li> <li><a href="/wiki/Toripristone" title="Toripristone">Toripristone</a></li> <li><a href="/wiki/Zanoterone" title="Zanoterone">Zanoterone</a></li></ul> <ul><li>Nonsteroidal: <a href="/wiki/Darolutamide" title="Darolutamide">Darolutamide</a></li> <li><a href="/w/index.php?title=LG-001447&action=edit&redlink=1" class="new" title="LG-001447 (page does not exist)">LG-001447</a></li> <li><a href="/w/index.php?title=LG-100127&action=edit&redlink=1" class="new" title="LG-100127 (page does not exist)">LG-100127</a></li> <li><a href="/w/index.php?title=LG-100128&action=edit&redlink=1" class="new" title="LG-100128 (page does not exist)">LG-100128</a></li> <li><a href="/w/index.php?title=LG-120830&action=edit&redlink=1" class="new" title="LG-120830 (page does not exist)">LG-120830</a></li> <li><a href="/w/index.php?title=LG-121046&action=edit&redlink=1" class="new" title="LG-121046 (page does not exist)">LG-121046</a></li> <li><a href="/wiki/Valproic_acid" class="mw-redirect" title="Valproic acid">Valproic acid</a></li> <li><a href="/w/index.php?title=ZM-150271&action=edit&redlink=1" class="new" title="ZM-150271 (page does not exist)">ZM-150271</a></li> <li><a href="/w/index.php?title=ZM-172406&action=edit&redlink=1" class="new" title="ZM-172406 (page does not exist)">ZM-172406</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Membrane_progesterone_receptor" title="Membrane progesterone receptor"><abbr title="Membrane progesterone receptor">mPR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Membrane progesterone receptor (<a href="/wiki/Progestin_and_adipoQ_receptor" title="Progestin and adipoQ receptor"><abbr title="Progestin and adipoQ receptor">PAQR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Progestin and adipoQ receptor)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">5α-Dihydroprogesterone</a></li> <li><a href="/wiki/5%CE%B2-Dihydroprogesterone" title="5β-Dihydroprogesterone">5β-Dihydroprogesterone</a></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycortisone (21-hydroxyprogesterone)</a></li> <li><a href="/wiki/11-Deoxycortisol" title="11-Deoxycortisol">11-Deoxycortisol (17α,21-dihydroxyprogesterone)</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone</a></li> <li><a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Progestogens_and_antiprogestogens" title="Template:Progestogens and antiprogestogens">Progestogens and antiprogestogens</a></dd> <dd><a href="/wiki/Template:Androgen_receptor_modulators" title="Template:Androgen receptor modulators">Androgen receptor modulators</a></dd> <dd><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators">Estrogen receptor modulators</a></dd> <dd><a href="/wiki/List_of_steroidal_progestogens" class="mw-redirect" title="List of steroidal progestogens">List of progestogens</a></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Mineralocorticoid_receptor_modulators767" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Mineralocorticoid_receptor_modulators" title="Template:Mineralocorticoid receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Mineralocorticoid_receptor_modulators" title="Template talk:Mineralocorticoid receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Mineralocorticoid_receptor_modulators" title="Special:EditPage/Template:Mineralocorticoid receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Mineralocorticoid_receptor_modulators767" style="font-size:114%;margin:0 4em"><a href="/wiki/Mineralocorticoid_receptor" title="Mineralocorticoid receptor">Mineralocorticoid receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Mineralocorticoid_receptor" title="Mineralocorticoid receptor"><abbr title="Mineralocorticoid receptor">MR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Mineralocorticoid receptor</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/11-Dehydrocorticosterone" title="11-Dehydrocorticosterone">11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone)</a> <ul><li><a href="/w/index.php?title=11-Dehydrocorticosterone_acetate&action=edit&redlink=1" class="new" title="11-Dehydrocorticosterone acetate (page does not exist)">11-Dehydrocorticosterone acetate</a></li></ul></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone (desoxycortone, deoxycortone, desoxycorticosterone)</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Desoxycortone_esters" title="List of corticosteroid esters">Desoxycortone esters</a></li></ul></li> <li><a href="/wiki/11-Deoxycortisol" title="11-Deoxycortisol">11-Deoxycortisol (cortodoxone, cortexolone)</a> <ul><li><a href="/wiki/Cortifen" title="Cortifen">Cortifen (cortiphen, kortifen)</a></li> <li><a href="/w/index.php?title=Cortodoxone_acetate&action=edit&redlink=1" class="new" title="Cortodoxone acetate (page does not exist)">Cortodoxone acetate</a></li></ul></li> <li><a href="/wiki/11%CE%B2-Hydroxyprogesterone" title="11β-Hydroxyprogesterone">11β-Hydroxyprogesterone</a></li> <li><a href="/w/index.php?title=16%CE%B1,18-Dihydroxy-11-deoxycorticosterone&action=edit&redlink=1" class="new" title="16α,18-Dihydroxy-11-deoxycorticosterone (page does not exist)">16α,18-Dihydroxy-11-deoxycorticosterone</a></li> <li><a href="/w/index.php?title=17%CE%B1-Hydroxyaldosterone&action=edit&redlink=1" class="new" title="17α-Hydroxyaldosterone (page does not exist)">17α-Hydroxyaldosterone</a></li> <li><a href="/wiki/18-Hydroxy-11-deoxycorticosterone" title="18-Hydroxy-11-deoxycorticosterone">18-Hydroxy-11-deoxycorticosterone</a></li> <li><a href="/wiki/19-Norprogesterone" title="19-Norprogesterone">19-Norprogesterone</a></li> <li><a href="/wiki/Aldosterone" title="Aldosterone">Aldosterone</a></li> <li><a href="/wiki/Corticosterone" title="Corticosterone">Corticosterone</a> <ul><li><a href="/w/index.php?title=Corticosterone_acetate&action=edit&redlink=1" class="new" title="Corticosterone acetate (page does not exist)">Corticosterone acetate</a></li> <li><a href="/w/index.php?title=Corticosterone_benzoate&action=edit&redlink=1" class="new" title="Corticosterone benzoate (page does not exist)">Corticosterone benzoate</a></li></ul></li> <li><a href="/wiki/Cortisol" title="Cortisol">Cortisol</a> (<a href="/wiki/Hydrocortisone" title="Hydrocortisone">hydrocortisone</a>) <ul><li><a href="/wiki/Benzodrocortisone" title="Benzodrocortisone">Benzodrocortisone (hydrocortisone benzoate)</a></li> <li><a href="/wiki/Hydrocortamate" title="Hydrocortamate">Hydrocortamate (hydrocortisone diethylaminoacetate)</a></li> <li><a href="/wiki/List_of_corticosteroid_esters#Hydrocortisone_esters" title="List of corticosteroid esters">Hydrocortisone esters</a></li></ul></li> <li><a href="/wiki/Cortisone" title="Cortisone">Cortisone</a> <ul><li><a href="/wiki/Cortisone_acetate" title="Cortisone acetate">Cortisone acetate</a></li></ul></li> <li><a href="/wiki/Fludrocortisone" title="Fludrocortisone">Fludrocortisone (fludrocortone)</a> <ul><li><a href="/wiki/Fludrocortisone_acetate" class="mw-redirect" title="Fludrocortisone acetate">Fludrocortisone acetate</a></li></ul></li> <li><a href="/wiki/Mometasone" title="Mometasone">Mometasone</a> <ul><li><a href="/wiki/Mometasone_furoate" class="mw-redirect" title="Mometasone furoate">Mometasone furoate</a></li></ul></li> <li><a href="/wiki/Prednisolone" title="Prednisolone">Prednisolone</a> <ul><li><a href="/wiki/Prednazate" title="Prednazate">Prednazate</a></li> <li><a href="/wiki/Prednazoline" title="Prednazoline">Prednazoline</a></li> <li><a href="/wiki/Prednicarbate" title="Prednicarbate">Prednicarbate (prednisolone ethylcarbonate propionate)</a></li> <li><a href="/wiki/Prednimustine" title="Prednimustine">Prednimustine</a></li> <li><a href="/wiki/Prednisolamate" title="Prednisolamate">Prednisolamate (prednisolone diethylaminoacetate)</a></li> <li><a href="/wiki/List_of_corticosteroid_esters#Prednisolone_esters" title="List of corticosteroid esters">Prednisolone esters</a></li></ul></li> <li><a href="/wiki/Prednisone" title="Prednisone">Prednisone</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Prednisone_esters" title="List of corticosteroid esters">Prednisone esters</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Steroidal: <a href="/wiki/6%CE%B2-Hydroxy-7%CE%B1-thiomethylspironolactone" title="6β-Hydroxy-7α-thiomethylspironolactone">6β-Hydroxy-7α-thiomethylspironolactone</a></li> <li><a href="/w/index.php?title=7%CE%B1-Acetylthio-17%CE%B1-hydroxyprogesterone&action=edit&redlink=1" class="new" title="7α-Acetylthio-17α-hydroxyprogesterone (page does not exist)">7α-Acetylthio-17α-hydroxyprogesterone</a></li> <li><a href="/wiki/7%CE%B1-Thiomethylspironolactone" title="7α-Thiomethylspironolactone">7α-Thiomethylspironolactone (SC-26519)</a></li> <li><a href="/wiki/7%CE%B1-Thioprogesterone" title="7α-Thioprogesterone">7α-Thioprogesterone (SC-8365)</a></li> <li><a href="/wiki/7%CE%B1-Thiospironolactone" title="7α-Thiospironolactone">7α-Thiospironolactone (SC-24813)</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyprogesterone" title="16α-Hydroxyprogesterone">16α-Hydroxyprogesterone</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone (hydroxyprogesterone)</a></li> <li><a href="/wiki/18-Deoxyaldosterone" title="18-Deoxyaldosterone">18-Deoxyaldosterone</a></li> <li><a href="/w/index.php?title=18,19-Dinorprogesterone&action=edit&redlink=1" class="new" title="18,19-Dinorprogesterone (page does not exist)">18,19-Dinorprogesterone</a></li> <li><a href="/wiki/Potassium_canrenoate" title="Potassium canrenoate">Canrenoate potassium (potassium canrenoate)</a></li> <li><a href="/wiki/Canrenoic_acid" title="Canrenoic acid">Canrenoic acid (canrenoate)</a></li> <li><a href="/wiki/Canrenone" title="Canrenone">Canrenone (canrenoate y-lactone)</a></li> <li><a href="/wiki/Dicirenone" title="Dicirenone">Dicirenone</a></li> <li><a href="/wiki/Dimethisterone" title="Dimethisterone">Dimethisterone</a></li> <li><a href="/wiki/Drospirenone" title="Drospirenone">Drospirenone</a></li> <li><a class="mw-selflink selflink">Dydrogesterone</a></li> <li><a href="/wiki/Eplerenone" title="Eplerenone">Eplerenone</a></li> <li><a href="/wiki/Gestodene" title="Gestodene">Gestodene</a></li> <li><a href="/wiki/Guggulsterone" title="Guggulsterone">Guggulsterone</a></li> <li><a href="/wiki/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">Hydroxyprogesterone caproate</a></li> <li><a href="/wiki/Medrogestone" title="Medrogestone">Medrogestone</a></li> <li><a href="/wiki/Mespirenone" title="Mespirenone">Mespirenone</a></li> <li><a href="/wiki/Metribolone" title="Metribolone">Metribolone</a></li> <li><a href="/wiki/Mexrenoate_potassium" title="Mexrenoate potassium">Mexrenoate potassium</a></li> <li><a href="/wiki/Mexrenoic_acid" title="Mexrenoic acid">Mexrenoic acid (mexrenoate)</a></li> <li><a href="/wiki/Mexrenone" title="Mexrenone">Mexrenone</a></li> <li><a href="/wiki/Oxprenoic_acid" title="Oxprenoic acid">Oxprenoic acid (oxprenoate)</a></li> <li><a href="/wiki/Oxprenoate_potassium" title="Oxprenoate potassium">Oxprenoate potassium (RU-28318)</a></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Prorenoate_potassium" title="Prorenoate potassium">Prorenoate potassium</a></li> <li><a href="/wiki/Prorenoic_acid" title="Prorenoic acid">Prorenoic acid (prorenoate)</a></li> <li><a href="/wiki/Prorenone" title="Prorenone">Prorenone</a></li> <li><a href="/w/index.php?title=RO-14-9012&action=edit&redlink=1" class="new" title="RO-14-9012 (page does not exist)">RO-14-9012</a></li> <li><a href="/w/index.php?title=RU-26752&action=edit&redlink=1" class="new" title="RU-26752 (page does not exist)">RU-26752</a></li> <li><a href="/wiki/SC-5233" title="SC-5233">SC-5233 (spirolactone)</a></li> <li><a href="/wiki/SC-8109" title="SC-8109">SC-8109</a></li> <li><a href="/w/index.php?title=SC-11927&action=edit&redlink=1" class="new" title="SC-11927 (page does not exist)">SC-11927 (CS-1)</a></li> <li><a href="/w/index.php?title=SC-19886&action=edit&redlink=1" class="new" title="SC-19886 (page does not exist)">SC-19886</a></li> <li><a href="/w/index.php?title=SC-27169&action=edit&redlink=1" class="new" title="SC-27169 (page does not exist)">SC-27169</a></li> <li><a href="/wiki/Spirorenone" title="Spirorenone">Spirorenone</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/wiki/Spiroxasone" title="Spiroxasone">Spiroxasone</a></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li> <li><a href="/wiki/Trimegestone" title="Trimegestone">Trimegestone</a></li> <li><a href="/wiki/Vamorolone" title="Vamorolone">Vamorolone</a></li> <li><a href="/w/index.php?title=ZK-91587&action=edit&redlink=1" class="new" title="ZK-91587 (page does not exist)">ZK-91587</a></li> <li><a href="/w/index.php?title=ZK-97894&action=edit&redlink=1" class="new" title="ZK-97894 (page does not exist)">ZK-97894</a></li></ul> <ul><li>Nonsteroidal: <a href="/wiki/Amlodipine" title="Amlodipine">Amlodipine</a></li> <li><a href="/wiki/Apararenone" title="Apararenone">Apararenone</a></li> <li><a href="/wiki/Benidipine" title="Benidipine">Benidipine</a></li> <li><a href="/w/index.php?title=BR-4628&action=edit&redlink=1" class="new" title="BR-4628 (page does not exist)">BR-4628</a></li> <li><a href="/wiki/Esaxerenone" title="Esaxerenone">Esaxerenone</a></li> <li><a href="/wiki/Felodipine" title="Felodipine">Felodipine</a></li> <li><a href="/wiki/Finerenone" title="Finerenone">Finerenone</a></li> <li><a href="/wiki/Miricorilant" title="Miricorilant">Miricorilant (CORT-118335)</a></li> <li><a href="/wiki/Nifedipine" title="Nifedipine">Nifedipine</a></li> <li><a href="/wiki/Nimodipine" title="Nimodipine">Nimodipine</a></li> <li><a href="/wiki/Nitrendipine" title="Nitrendipine">Nitrendipine</a></li> <li><a href="/wiki/Ocedurenone" title="Ocedurenone">Ocedurenone</a></li> <li><a href="/w/index.php?title=PF-03882845&action=edit&redlink=1" class="new" title="PF-03882845 (page does not exist)">PF-03882845</a></li> <li><a href="/w/index.php?title=SM-368229&action=edit&redlink=1" class="new" title="SM-368229 (page does not exist)">SM-368229</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Mineralocorticoids_and_antimineralocorticoids" title="Template:Mineralocorticoids and antimineralocorticoids">Mineralocorticoids and antimineralocorticoids</a></dd> <dd><a href="/wiki/Template:Glucocorticoid_receptor_modulators" title="Template:Glucocorticoid receptor modulators">Glucocorticoid receptor modulators</a></dd> <dd><a href="/wiki/List_of_corticosteroids" title="List of corticosteroids">List of corticosteroids</a></dd></dl> </div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Dydrogesterone&oldid=1267820373">https://en.wikipedia.org/w/index.php?title=Dydrogesterone&oldid=1267820373</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Antimineralocorticoids" title="Category:Antimineralocorticoids">Antimineralocorticoids</a></li><li><a href="/wiki/Category:Conjugated_dienes" 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