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.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">Gestonorone caproate</caption><tbody><tr><td colspan="2" class="infobox-image"><a href="/wiki/File:Gestronol_caproate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cf/Gestronol_caproate.svg/250px-Gestronol_caproate.svg.png" decoding="async" width="250" height="117" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cf/Gestronol_caproate.svg/375px-Gestronol_caproate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cf/Gestronol_caproate.svg/500px-Gestronol_caproate.svg.png 2x" data-file-width="512" data-file-height="240" /></a></td></tr><tr><td colspan="2" class="infobox-image"><a href="/wiki/File:Gestonorone_caproate_molecule_ball.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c2/Gestonorone_caproate_molecule_ball.png/250px-Gestonorone_caproate_molecule_ball.png" decoding="async" width="250" height="150" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c2/Gestonorone_caproate_molecule_ball.png/375px-Gestonorone_caproate_molecule_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c2/Gestonorone_caproate_molecule_ball.png/500px-Gestonorone_caproate_molecule_ball.png 2x" data-file-width="3840" data-file-height="2305" /></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">Depostat, Primostat</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">Gestronol hexanoate; Norhydroxyprogesterone caproate; SH-582; SH-80582; NSC-84054; 17α-Hydroxy-19-norpregn-4-ene-3,20-dione hexanoate; 17α-Hydroxy-19-norprogesterone hexanoate</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/Intramuscular_injection" title="Intramuscular injection">Intramuscular injection</a><a href="#cite_note-Muller1998-1">[1]</a><a href="#cite_note-Aronson2009-2">[2]</a><a href="#cite_note-MortonHall2012-3">[3]</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>; <a href="/wiki/Progestogen_ester" title="Progestogen ester">Progestogen ester</a>; <a href="/wiki/Antigonadotropin" title="Antigonadotropin">Antigonadotropin</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">G03DA01</a> (<a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=G03DA01">WHO</a>) <a href="/wiki/ATC_code_L02" title="ATC code L02">L02AB03</a> (<a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=L02AB03">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">Oral: Low<a href="#cite_note-pmid4285463-4">[4]</a> <abbr title="Intramuscular injection">IM</abbr>: High<a href="#cite_note-BruchhausenDannhardt2013-5">[5]</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/Redox" title="Redox">Reduction</a> (at the C5, C3, and C20 positions)<a href="#cite_note-Springer2013-6">[6]</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">• 19-Norpregnanetriol<a href="#cite_note-Springer2013-6">[6]</a> • 19-Norpregnanediol-20-one<a href="#cite_note-Springer2013-6">[6]</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="Intramuscular injection">IM</abbr>: 7.5 ± 3.1 days<a href="#cite_note-BruchhausenDannhardt2013-5">[5]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Pharmacodynamics#Duration_of_action" title="Pharmacodynamics">Duration of action</a></th><td class="infobox-data"><abbr title="Intramuscular injection">IM</abbr>: ≥21 days<a href="#cite_note-BruchhausenDannhardt2013-5">[5]</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>: 28%<a href="#cite_note-BruchhausenDannhardt2013-5">[5]</a> <a href="/wiki/Feces" title="Feces">Feces</a>: 72%<a href="#cite_note-BruchhausenDannhardt2013-5">[5]</a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">[(8R,9S,10R,13S,14S,17R)-17-acetyl-13-methyl-3-oxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] hexanoate</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=1253-28-7">1253-28-7</a></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/443881">443881</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/DB14677">DB14677</a></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.391969.html">391969</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/U38E620NS6">U38E620NS6</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/D01159">D01159</a></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:31650">CHEBI:31650</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL2107389">ChEMBL2107389</a></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/DTXSID40871837">DTXSID40871837</a> <a href="https://www.wikidata.org/wiki/Q11320734#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/100.013.646">100.013.646</a> <a href="https://www.wikidata.org/wiki/Q11320734#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">C26H38O4</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">414.586 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=CCCCCC%28%3DO%29OC1%28CCC2C1%28CCC3C2CCC4%3DCC%28%3DO%29CCC34%29C%29C%28%3DO%29C">Interactive image</a></li></ul></div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">CCCCCC(=O)OC1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34)C)C(=O)C</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">InChI=1S/C26H38O4/c1-4-5-6-7-24(29)30-26(17(2)27)15-13-23-22-10-8-18-16-19(28)9-11-20(18)21(22)12-14-25(23,26)3/h16,20-23H,4-15H2,1-3H3/t20-,21+,22+,23-,25-,26-/m0/s1</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:XURCMZMFZXXQDJ-UKNJCJGYSA-N</div></li></ul> </div></td></tr></tbody></table> Gestonorone caproate, also known as gestronol hexanoate or norhydroxyprogesterone caproate and sold under the brand names Depostat and Primostat, is a <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestin</a> medication which is used in the treatment of <a href="/wiki/Benign_prostatic_hyperplasia" title="Benign prostatic hyperplasia">enlarged prostate</a> and <a href="/wiki/Endometrial_cancer" title="Endometrial cancer">cancer of the endometrium</a>.<a href="#cite_note-BruchhausenDannhardt2013-5">[5]</a><a href="#cite_note-MortonHall2012-3">[3]</a><a href="#cite_note-Publishing2013-7">[7]</a><a href="#cite_note-Muller1998-1">[1]</a><a href="#cite_note-Thurston2006-8">[8]</a> It is given by <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">injection into muscle</a> typically once a week.<a href="#cite_note-pmid4285463-4">[4]</a> <a href="/wiki/Side_effect" title="Side effect">Side effects</a> of gestonorone caproate include worsened <a href="/wiki/Glucose_tolerance" class="mw-redirect" title="Glucose tolerance">glucose tolerance</a>, <a href="/wiki/Decreased_libido" class="mw-redirect" title="Decreased libido">decreased libido</a> in men, and <a href="/wiki/Injection_site_reaction" title="Injection site reaction">injection site reactions</a>.<a href="#cite_note-BruchhausenDannhardt2013-5">[5]</a> Gestonorone caproate 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-Raspé2013-9">[9]</a><a href="#cite_note-SchooneesDe_Klerk1969-10">[10]</a> It has no other important <a href="/wiki/Hormonal_agent" class="mw-redirect" title="Hormonal agent">hormonal</a> activity.<a href="#cite_note-BruchhausenDannhardt2013-5">[5]</a><a href="#cite_note-HorskyPresl1981a-11">[11]</a><a href="#cite_note-Schering1968-12">[12]</a><a href="#cite_note-AubreyKhosla1971-13">[13]</a> Gestonorone caproate was discovered in 1960 and was introduced for medical use by 1973.<a href="#cite_note-Kaiser1960-14">[14]</a><a href="#cite_note-SubbiahMortensen1973-15">[15]</a> It has been used widely throughout <a href="/wiki/Europe" title="Europe">Europe</a>, including in the <a href="/wiki/United_Kingdom" title="United Kingdom">United Kingdom</a>, and has also been marketed in certain other countries such as <a href="/wiki/Japan" title="Japan">Japan</a>, <a href="/wiki/China" title="China">China</a>, and <a href="/wiki/Mexico" title="Mexico">Mexico</a>.<a href="#cite_note-Muller1998-1">[1]</a><a href="#cite_note-IndexNominum2000-16">[16]</a><a href="#cite_note-Drugs.com-17">[17]</a><a href="#cite_note-Micromedex-18">[18]</a> However, it has since mostly been discontinued, and it remains available today only in a handful of countries, including the <a href="/wiki/Czech_Republic" title="Czech Republic">Czech Republic</a>, Japan, Mexico, and <a href="/wiki/Russia" title="Russia">Russia</a>.<a href="#cite_note-Micromedex-18">[18]</a><a href="#cite_note-Martindale-19">[19]</a> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Medical_uses">Medical uses</h2>[<a href="/w/index.php?title=Gestonorone_caproate&action=edit&section=1" title="Edit section: Medical uses">edit</a>]</div> Gestonorone caproate is used in the <a href="/wiki/Palliation" class="mw-redirect" title="Palliation">palliative</a> treatment of <a href="/wiki/Benign_prostatic_hyperplasia" title="Benign prostatic hyperplasia">benign prostatic hyperplasia</a> and <a href="/wiki/Endometrial_cancer" title="Endometrial cancer">endometrial cancer</a>.<a href="#cite_note-BruchhausenDannhardt2013-5">[5]</a><a href="#cite_note-MortonHall2012-3">[3]</a><a href="#cite_note-SmithWilliams2005-20">[20]</a> It is used at a dose of 100 to 200 mg once a week by <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">intramuscular injection</a>.<a href="#cite_note-BruchhausenDannhardt2013-5">[5]</a> <div class="mw-heading mw-heading2"><h2 id="Side_effects">Side effects</h2>[<a href="/w/index.php?title=Gestonorone_caproate&action=edit&section=2" title="Edit section: Side effects">edit</a>]</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Progestin#Side_effects" class="mw-redirect" title="Progestin">Progestin § Side effects</a></div> <a href="/wiki/Side_effect" title="Side effect">Side effects</a> of gestonorone caproate have been reported to include worsened <a href="/wiki/Glucose_tolerance" class="mw-redirect" title="Glucose tolerance">glucose tolerance</a>, <a href="/wiki/Decreased_libido" class="mw-redirect" title="Decreased libido">decreased libido</a> in men, and local <a href="/wiki/Injection_site_reaction" title="Injection site reaction">injection site reactions</a> such as <a href="/wiki/Irritation" title="Irritation">irritation</a>.<a href="#cite_note-BruchhausenDannhardt2013-5">[5]</a> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2>[<a href="/w/index.php?title=Gestonorone_caproate&action=edit&section=3" title="Edit section: Pharmacology">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Pharmacodynamics">Pharmacodynamics</h3>[<a href="/w/index.php?title=Gestonorone_caproate&action=edit&section=4" title="Edit section: Pharmacodynamics">edit</a>]</div> Gestonorone caproate is a <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potent</a>, long-acting, and pure <a href="/wiki/Progestogen_(medication)" title="Progestogen (medication)">progestogen</a>,<a href="#cite_note-Raspé2013-9">[9]</a><a href="#cite_note-SchooneesDe_Klerk1969-10">[10]</a><a href="#cite_note-AubreyKhosla1971-13">[13]</a> possessing no <a href="/wiki/Androgen" title="Androgen">androgenic</a>, <a href="/wiki/Anabolic" class="mw-redirect" title="Anabolic">anabolic</a>, <a href="/wiki/Antiandrogen" title="Antiandrogen">antiandrogenic</a>, <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogenic</a>, <a href="/wiki/Antiestrogen" title="Antiestrogen">antiestrogenic</a>, <a href="/wiki/Glucocorticoid" title="Glucocorticoid">glucocorticoid</a>, <a href="/wiki/Mineralocorticoid" title="Mineralocorticoid">mineralocorticoid</a>, or <a href="/wiki/Teratogen" class="mw-redirect" title="Teratogen">teratogenic</a> effects.<a href="#cite_note-BruchhausenDannhardt2013-5">[5]</a><a href="#cite_note-HorskyPresl1981a-11">[11]</a><a href="#cite_note-Schering1968-12">[12]</a><a href="#cite_note-AubreyKhosla1971-13">[13]</a><a href="#cite_note-pmid102602-21">[21]</a> It is approximately 20 to 25 times more potent than <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a> or <a href="/wiki/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">hydroxyprogesterone caproate</a> in animal <a href="/wiki/Bioassay" title="Bioassay">bioassays</a> when all are given by <a href="/wiki/Subcutaneous_injection" class="mw-redirect" title="Subcutaneous injection">subcutaneous injection</a>.<a href="#cite_note-BruchhausenDannhardt2013-5">[5]</a><a href="#cite_note-AubreyKhosla1971-13">[13]</a><a href="#cite_note-pmid4555897-22">[22]</a> In humans, 100 or 200 mg intramuscular gestonorone caproate has been said to be equivalent to 1,000 mg intramuscular hydroxyprogesterone caproate.<a href="#cite_note-pmid5556820-23">[23]</a><a href="#cite_note-pmid4261828-24">[24]</a> Hence, gestonorone caproate is approximately 5- to 10-fold more potent than hydroxyprogesterone caproate in humans.<a href="#cite_note-HorskyPresl1981a-11">[11]</a><a href="#cite_note-pmid5556820-23">[23]</a><a href="#cite_note-pmid4261828-24">[24]</a> The <a href="/wiki/Biological_effect" class="mw-redirect" title="Biological effect">biological effects</a> of gestonorone caproate in women have been studied.<a href="#cite_note-JürgensenTaubert1969-25">[25]</a><a href="#cite_note-Ferin1972a-26">[26]</a> Like other potent progestins, gestonorone caproate possesses potent <a href="/wiki/Antigonadotropic" class="mw-redirect" title="Antigonadotropic">antigonadotropic</a> activity and is capable of markedly suppressing the <a href="/wiki/Gonad" title="Gonad">gonadal</a> production and circulating levels of sex hormones such as <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> and <a href="/wiki/Estradiol" title="Estradiol">estradiol</a>.<a href="#cite_note-AubreyKhosla1971-13">[13]</a><a href="#cite_note-RaspéBrosig2013-27">[27]</a><a href="#cite_note-MakrigiannisGaca1971-28">[28]</a> A clinical study found that 400 mg/week intramuscular gestonorone caproate suppressed testosterone levels by 75% in men, while <a href="/wiki/Orchiectomy" title="Orchiectomy">orchiectomy</a> as a comparator reduced testosterone levels by 91%.<a href="#cite_note-pmid694436-29">[29]</a><a href="#cite_note-pmid519881-30">[30]</a> Levels of <a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone">luteinizing hormone</a>, conversely, remained unchanged.<a href="#cite_note-pmid694436-29">[29]</a> In general, progestogens can maximally suppress testosterone levels by about 70 to 80%.<a href="#cite_note-WeinKavoussi2011-31">[31]</a><a href="#cite_note-pmid6237116-32">[32]</a><a href="#cite_note-pmid7000222-33">[33]</a><a href="#cite_note-pmid694436-29">[29]</a><a href="#cite_note-pmid519881-30">[30]</a> In accordance with its lack of glucocorticoid activity, gestonorone caproate has no <a href="/wiki/Anticorticotropic" class="mw-redirect" title="Anticorticotropic">anticorticotropic</a> effects, and does not influence the <a href="/wiki/Secretion" title="Secretion">secretion</a> of <a href="/wiki/Adrenocorticotropic_hormone" title="Adrenocorticotropic hormone">adrenocorticotropic hormone</a>.<a href="#cite_note-BruchhausenDannhardt2013-5">[5]</a> <a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone</a> has weak <a href="/wiki/Progestogen_(medication)" title="Progestogen (medication)">progestogenic</a> activity, but C17α <a href="/wiki/Esterification" class="mw-redirect" title="Esterification">esterification</a> results in higher progestogenic activity.<a href="#cite_note-Springer2013-6">[6]</a> Of a variety of different <a href="/wiki/Ester" title="Ester">esters</a>, the <a href="/wiki/Caproate" class="mw-redirect" title="Caproate">caproate</a> (hexanoate) ester was found to have the strongest progestogenic activity, and this formed the basis for the development of gestonorone caproate, as well as other caproate <a href="/wiki/Progestogen_ester" title="Progestogen ester">progestogen esters</a> such as hydroxyprogesterone caproate.<a href="#cite_note-Springer2013-6">[6]</a> Gestonorone caproate has been found to decrease the weights of the <a href="/wiki/Prostate_gland" class="mw-redirect" title="Prostate gland">prostate gland</a> and <a href="/wiki/Seminal_vesicle" class="mw-redirect" title="Seminal vesicle">seminal vesicles</a> by 40 to 70% in adult male rats.<a href="#cite_note-BruchhausenDannhardt2013-5">[5]</a> It has been shown in <a href="/wiki/Dog" title="Dog">canines</a> to mediate these effects both via its antigonadotropic effects and by direct actions in these tissues.<a href="#cite_note-BruchhausenDannhardt2013-5">[5]</a> Gestonorone caproate decreases the uptake of testosterone into the prostate gland.<a href="#cite_note-BruchhausenDannhardt2013-5">[5]</a> It has also been found to have direct <a href="/wiki/Antiproliferative" class="mw-redirect" title="Antiproliferative">antiproliferative</a> effects on human <a href="/wiki/Ovarian_cancer" title="Ovarian cancer">ovarian cancer</a> <a href="/wiki/Cell_(biology)" title="Cell (biology)">cells</a> <a href="/wiki/In_vitro" title="In vitro">in vitro</a>.<a href="#cite_note-BruchhausenDannhardt2013-5">[5]</a> Gestonorone caproate has been reported to act to some extent as a <a href="/wiki/5%CE%B1-reductase_inhibitor" class="mw-redirect" title="5α-reductase inhibitor">5α-reductase inhibitor</a>, similarly to progesterone.<a href="#cite_note-pmid64267-34">[34]</a><a href="#cite_note-pmid1177428-35">[35]</a> <table class="wikitable plainrowheaders floatright" style="font-size:small;"> <caption class="nowrap" style="font-size: 105%;"><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 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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: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-55">[a]</a><a href="#cite_note-56">[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-57">[c]</a> </th> <th scope="col" rowspan="2"><abbr title="Duration of action">DOA</abbr><a href="#cite_note-58">[d]</a> </th></tr> <tr> <th scope="col"><abbr title="Endometrial transformation dose">TFD</abbr><a href="#cite_note-59">[e]</a> </th> <th scope="col"><abbr title="Progestogen-only injectable contraceptive dose">POICD</abbr><a href="#cite_note-60">[f]</a> </th> <th scope="col"><abbr title="Combined injectable contraceptive dose">CICD</abbr><a href="#cite_note-61">[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>Gestonorone caproate</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-62">[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-63">[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-63">[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-55"><a href="#cite_ref-55">^</a> Sources: <a href="#cite_note-KnörrBeller2013-36">[36]</a><a href="#cite_note-KnörrKnörr-Gärtner2013y-37">[37]</a><a href="#cite_note-Labhart2012-38">[38]</a><a href="#cite_note-HorskyPresl1981-39">[39]</a><a href="#cite_note-Ufer1969-40">[40]</a><a href="#cite_note-Pschyrembel1968r-41">[41]</a><a href="#cite_note-Ferin1972-42">[42]</a><a href="#cite_note-HenzlEdwards1999u-43">[43]</a><a href="#cite_note-Brotherton1976-44">[44]</a><a href="#cite_note-pmid8013220-45">[45]</a><a href="#cite_note-pmid8013216-46">[46]</a><a href="#cite_note-Goebelsmann1986-47">[47]</a><a href="#cite_note-BeckerDüsterberg1980-48">[48]</a><a href="#cite_note-MoltzHaase2008-49">[49]</a><a href="#cite_note-WrightBurgess2012-50">[50]</a><a href="#cite_note-ChuLi1986-51">[51]</a><a href="#cite_note-RunnebaumRabe2012-52">[52]</a><a href="#cite_note-ArtiniGenazzani2001-53">[53]</a><a href="#cite_note-KingBrucker2013-54">[54]</a> </li> <li id="cite_note-56"><a href="#cite_ref-56">^</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-57"><a href="#cite_ref-57">^</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-58"><a href="#cite_ref-58">^</a> Duration of action in days. </li> <li id="cite_note-59"><a href="#cite_ref-59">^</a> Usually given for 14 days. </li> <li id="cite_note-60"><a href="#cite_ref-60">^</a> Usually dosed every two to three months. </li> <li id="cite_note-61"><a href="#cite_ref-61">^</a> Usually dosed once monthly. </li> <li id="cite_note-mark-62"><a href="#cite_ref-mark_62-0">^</a> Never marketed or approved by this route. </li> <li id="cite_note-div-63">^ <a href="#cite_ref-div_63-0">a</a> <a href="#cite_ref-div_63-1">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-heading3"><h3 id="Pharmacokinetics">Pharmacokinetics</h3>[<a href="/w/index.php?title=Gestonorone_caproate&action=edit&section=5" title="Edit section: Pharmacokinetics">edit</a>]</div> Like the closely related progestins hydroxyprogesterone caproate and <a href="/wiki/19-norprogesterone" class="mw-redirect" title="19-norprogesterone">19-norprogesterone</a>, gestonorone caproate shows poor activity <a href="/wiki/Oral_administration" title="Oral administration">orally</a> and must be administered <a href="/wiki/Parenteral" class="mw-redirect" title="Parenteral">parenterally</a>; specifically, via <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">intramuscular injection</a>.<a href="#cite_note-pmid4285463-4">[4]</a> Gestonorone caproate is administered by intramuscular injection, and acts as a long-lasting <a href="/wiki/Depot_injection" title="Depot injection">depot</a> by this route.<a href="#cite_note-BruchhausenDannhardt2013-5">[5]</a><a href="#cite_note-Denis2012-64">[55]</a><a href="#cite_note-RunnebaumRabe2012a-65">[56]</a><a href="#cite_note-PalancaJuco2008-66">[57]</a> After an intramuscular injection, gestonorone caproate is completely released from the local depot and is highly <a href="/wiki/Bioavailability" title="Bioavailability">bioavailable</a>.<a href="#cite_note-BruchhausenDannhardt2013-5">[5]</a> A single <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">intramuscular injection</a> of 25 to 50 mg gestonorone caproate in <a href="/wiki/Oil_solution" class="mw-redirect" title="Oil solution">oil solution</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 8 to 13 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-Ferin1972a-26">[26]</a><a href="#cite_note-Nevinny-Stickel1962-67">[58]</a><a href="#cite_note-HorskyPresl1981b-68">[59]</a> At high doses, the <a href="/wiki/Duration_of_action" class="mw-redirect" title="Duration of action">duration of action</a> of gestonorone caproate by intramuscular injection has been found to be at least 21 days.<a href="#cite_note-BruchhausenDannhardt2013-5">[5]</a> Clinical studies have found gestonorone caproate to be satisfactorily effective as a progestogen when injected once a month, whereas it was poorly effective as an injectable contraceptive when it was injected once every two months.<a href="#cite_note-pmid340117-69">[60]</a><a href="#cite_note-pmid865726-70">[61]</a> Following a single intramuscular injection of 200 mg <a href="/wiki/Radiolabel" class="mw-redirect" title="Radiolabel">radiolabeled</a> gestonorone caproate in 1 mL of <a href="/wiki/Solution_(chemistry)" title="Solution (chemistry)">solution</a> in men with prostate cancer, <a href="/wiki/Cmax_(pharmacology)" title="Cmax (pharmacology)">maximal</a> levels of gestonorone caproate occurred after 3 ± 1 days and were 420 ± 160 ng/mL.<a href="#cite_note-BruchhausenDannhardt2013-5">[5]</a> The <a href="/wiki/Elimination_half-life" class="mw-redirect" title="Elimination half-life">elimination half-life</a> of gestonorone caproate and its <a href="/wiki/Metabolite" title="Metabolite">metabolites</a> was 7.5 ± 3.1 days.<a href="#cite_note-BruchhausenDannhardt2013-5">[5]</a> Approximately 5% of the <a href="/wiki/Radioactivity" class="mw-redirect" title="Radioactivity">radioactive</a> <a href="/wiki/Steroid" title="Steroid">steroid</a> content in the blood was unchanged gestonorone caproate.<a href="#cite_note-BruchhausenDannhardt2013-5">[5]</a> No free <a href="/wiki/Gestonorone" class="mw-redirect" title="Gestonorone">gestonorone</a> was observed in <a href="/wiki/Circulatory_system" title="Circulatory system">circulation</a> or in <a href="/wiki/Urine" title="Urine">urine</a>.<a href="#cite_note-BruchhausenDannhardt2013-5">[5]</a> Gestonorone caproate and its metabolites were <a href="/wiki/Elimination_(pharmacology)" title="Elimination (pharmacology)">eliminated</a> 72% in <a href="/wiki/Feces" title="Feces">feces</a> and 28% in <a href="/wiki/Urine" title="Urine">urine</a>.<a href="#cite_note-BruchhausenDannhardt2013-5">[5]</a><a href="#cite_note-NagelKolb1973-71">[62]</a> Approximately 48 ± 18% of the injected dose had been eliminated after 14 days and approximately 85 ± 12% of the injected dose had been excreted after 30 days.<a href="#cite_note-BruchhausenDannhardt2013-5">[5]</a> The <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> of unesterified gestonorone (17α-hydroxy-19-norprogesterone) is analogous to that of <a href="/wiki/17%CE%B1-hydroxyprogesterone" class="mw-redirect" title="17α-hydroxyprogesterone">17α-hydroxyprogesterone</a>, with the corresponding <a href="/wiki/19-norpregnane" class="mw-redirect" title="19-norpregnane">19-norpregnane</a> <a href="/wiki/Metabolite" title="Metabolite">metabolites</a> produced.<a href="#cite_note-Springer2013-6">[6]</a> Gestonorone caproate has been found to undergo <a href="/wiki/5%CE%B1-reductase" class="mw-redirect" title="5α-reductase">5α-reduction</a> similarly to <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a>, 17α-hydroxyprogesterone, and gestonorone, and at a similar rate as these <a href="/wiki/Steroid" title="Steroid">steroids</a>.<a href="#cite_note-Springer2013-6">[6]</a> Conversely however, due to its caproate ester, <a href="/wiki/5%CE%B2-reductase" class="mw-redirect" title="5β-reductase">5β-reduction</a> of gestonorone caproate is decreased relative to these steroids.<a href="#cite_note-Springer2013-6">[6]</a> As progesterone is <a href="/wiki/Metabolism" title="Metabolism">metabolized</a> mainly into <a href="/wiki/5%CE%B2-pregnane" class="mw-redirect" title="5β-pregnane">5β-pregnanes</a>, decreased 5β-reduction of gestonorone caproate may be involved in its greater <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potency</a> compared to progesterone.<a href="#cite_note-Springer2013-6">[6]</a> The major <a href="/wiki/Metabolite" title="Metabolite">metabolites</a> of gestonorone caproate have been reported to be <a href="/wiki/Isomer" title="Isomer">isomers</a> of 19-norpregnanetriol and 19-norpregnanediol-20-one.<a href="#cite_note-Springer2013-6">[6]</a><a href="#cite_note-pmid102602-21">[21]</a> These metabolites indicate that gestonorone caproate is metabolized mainly by <a href="/wiki/Redox" title="Redox">reduction</a> at the C3, C5, and C20 positions.<a href="#cite_note-Springer2013-6">[6]</a> Following an intramuscular injection of 300 mg gestonorone caproate, only a slight increase in <a href="/wiki/Urine" title="Urine">urinary</a> <a href="/wiki/Pregnanetriol" title="Pregnanetriol">pregnanetriol</a> <a href="/wiki/Excretion" title="Excretion">excretion</a> has been observed.<a href="#cite_note-Springer2013-6">[6]</a> <a href="/wiki/Bond_cleavage" title="Bond cleavage">Cleavage</a> of the caproate ester of gestonorone caproate is minimal, which indicates that it is not a <a href="/wiki/Prodrug" title="Prodrug">prodrug</a> of the unesterified steroid.<a href="#cite_note-Springer2013-6">[6]</a> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2>[<a href="/w/index.php?title=Gestonorone_caproate&action=edit&section=6" title="Edit section: Chemistry">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/List_of_progestogens" title="List of progestogens">List of progestogens</a>, <a href="/wiki/Progestogen_ester" title="Progestogen ester">Progestogen ester</a>, and <a href="/wiki/List_of_progestogen_esters" title="List of progestogen esters">List of progestogen esters</a></div> Gestonorone caproate, also known as norhydroxyprogesterone caproate, 17α-hydroxy-19-norprogesterone 17α-hexanoate, or 17α-hydroxy-19-norpregn-4-ene-3,20-dione 17α-hexanoate, is a <a href="/wiki/Synthetic_compound" class="mw-redirect" title="Synthetic compound">synthetic</a> <a href="/wiki/Norpregnane" class="mw-redirect" title="Norpregnane">norpregnane</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" title="Progesterone">progesterone</a>.<a href="#cite_note-Elks2014-72">[63]</a><a href="#cite_note-IndexNominum2000-16">[16]</a> It is specifically a combined derivative of <a href="/wiki/17%CE%B1-hydroxyprogesterone" class="mw-redirect" title="17α-hydroxyprogesterone">17α-hydroxyprogesterone</a> and <a href="/wiki/19-norprogesterone" class="mw-redirect" title="19-norprogesterone">19-norprogesterone</a>, or of <a href="/wiki/Gestronol" title="Gestronol">gestronol</a> (17α-hydroxy-19-norprogesterone), with a <a href="/wiki/Hexanoate" class="mw-redirect" title="Hexanoate">hexanoate</a> (caproate) <a href="/wiki/Ester" title="Ester">ester</a> at the C17α position.<a href="#cite_note-Elks2014-72">[63]</a><a href="#cite_note-IndexNominum2000-16">[16]</a> <a href="/wiki/Structural_analogue" class="mw-redirect" title="Structural analogue">Analogues</a> and derivatives of gestonorone caproate include <a href="/wiki/Algestone_acetophenide" title="Algestone acetophenide">algestone acetophenide</a> (dihydroxyprogesterone acetophenide), <a href="/wiki/Demegestone" title="Demegestone">demegestone</a>, <a href="/wiki/Nomegestrol_acetate" title="Nomegestrol acetate">nomegestrol acetate</a>, <a href="/wiki/Norgestomet" title="Norgestomet">norgestomet</a>, and <a href="/wiki/Segesterone_acetate" title="Segesterone acetate">segesterone acetate</a>, as well as <a href="/wiki/18-methylsegesterone_acetate" class="mw-redirect" title="18-methylsegesterone acetate">18-methylsegesterone acetate</a> and the <a href="/wiki/Caproate" class="mw-redirect" title="Caproate">caproate</a> esters <a href="/wiki/Chlormadinone_caproate" title="Chlormadinone caproate">chlormadinone caproate</a>, <a href="/wiki/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">hydroxyprogesterone caproate</a>, <a href="/wiki/Medroxyprogesterone_caproate" title="Medroxyprogesterone caproate">medroxyprogesterone caproate</a>, <a href="/wiki/Megestrol_caproate" title="Megestrol caproate">megestrol caproate</a>, and <a href="/wiki/Methenmadinone_caproate" title="Methenmadinone caproate">methenmadinone caproate</a>.<a href="#cite_note-Elks2014-72">[63]</a><a href="#cite_note-IndexNominum2000-16">[16]</a> <div class="mw-heading mw-heading3"><h3 id="Synthesis">Synthesis</h3>[<a href="/w/index.php?title=Gestonorone_caproate&action=edit&section=7" title="Edit section: Synthesis">edit</a>]</div> <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">Chemical syntheses</a> of gestonorone caproate have been published.<a href="#cite_note-BruchhausenDannhardt2013-5">[5]</a><a href="#cite_note-Publishing2013-7">[7]</a><a href="#cite_note-KleemannEngel2001-73">[64]</a> <div class="mw-heading mw-heading2"><h2 id="History">History</h2>[<a href="/w/index.php?title=Gestonorone_caproate&action=edit&section=8" title="Edit section: History">edit</a>]</div> Gestonorone caproate was first described in 1960.<a href="#cite_note-Kaiser1960-14">[14]</a> It was developed by <a href="/wiki/Schering_AG" title="Schering AG">Schering</a> and has been marketed since at least 1968.<a href="#cite_note-Schering1968-12">[12]</a><a href="#cite_note-SubbiahMortensen1973-15">[15]</a> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2>[<a href="/w/index.php?title=Gestonorone_caproate&action=edit&section=9" 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=Gestonorone_caproate&action=edit&section=10" title="Edit section: Generic names">edit</a>]</div> Gestonorone caproate 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/Japanese_Accepted_Name" title="Japanese Accepted Name"><abbr title="Japanese Accepted Name">JAN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Japanese Accepted Name, while gestronol hexanoate is its <a href="/wiki/British_Approved_Name" title="British Approved Name"><abbr title="British Approved Name">BANM</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip British Approved Name.<a href="#cite_note-Elks2014-72">[63]</a><a href="#cite_note-IndexNominum2000-16">[16]</a> It has also been referred to as norhydroxyprogesterone caproate, and is also known by its former developmental code names SH-582 and SH-80582.<a href="#cite_note-Elks2014-72">[63]</a><a href="#cite_note-IndexNominum2000-16">[16]</a><a href="#cite_note-Drugs.com-17">[17]</a> <div class="mw-heading mw-heading3"><h3 id="Brand_names">Brand names</h3>[<a href="/w/index.php?title=Gestonorone_caproate&action=edit&section=11" title="Edit section: Brand names">edit</a>]</div> Gestonorone caproate has been marketed exclusively under the brand names Depostat and Primostat.<a href="#cite_note-Elks2014-72">[63]</a><a href="#cite_note-IndexNominum2000-16">[16]</a><a href="#cite_note-Drugs.com-17">[17]</a><a href="#cite_note-Micromedex-18">[18]</a><a href="#cite_note-Martindale-19">[19]</a> <div class="mw-heading mw-heading3"><h3 id="Availability">Availability</h3>[<a href="/w/index.php?title=Gestonorone_caproate&action=edit&section=12" title="Edit section: Availability">edit</a>]</div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Gestonorone_caproate_availability.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9f/Gestonorone_caproate_availability.png/300px-Gestonorone_caproate_availability.png" decoding="async" width="300" height="162" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9f/Gestonorone_caproate_availability.png/450px-Gestonorone_caproate_availability.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9f/Gestonorone_caproate_availability.png/600px-Gestonorone_caproate_availability.png 2x" data-file-width="4000" data-file-height="2155" /></a><figcaption>Availability of gestonorone caproate in countries throughout the world as of March 2018. Blue is currently marketed, green is formerly marketed.</figcaption></figure> Gestonorone caproate has been available widely in <a href="/wiki/Europe" title="Europe">Europe</a>, including in the <a href="/wiki/United_Kingdom" title="United Kingdom">United Kingdom</a>, and has also been marketed in <a href="/wiki/Japan" title="Japan">Japan</a>, <a href="/wiki/China" title="China">China</a>, <a href="/wiki/Mexico" title="Mexico">Mexico</a>, and certain other countries.<a href="#cite_note-Muller1998-1">[1]</a><a href="#cite_note-IndexNominum2000-16">[16]</a><a href="#cite_note-Drugs.com-17">[17]</a><a href="#cite_note-Micromedex-18">[18]</a> However, it has been discontinued in most countries and its availability is more limited today; it appears to remain marketed only in the <a href="/wiki/Czech_Republic" title="Czech Republic">Czech Republic</a>, Japan, Mexico, and <a href="/wiki/Russia" title="Russia">Russia</a>.<a href="#cite_note-Micromedex-18">[18]</a><a href="#cite_note-Martindale-19">[19]</a><a href="#cite_note-MHRA-74">[65]</a> It has not been marketed in the <a href="/wiki/United_States" title="United States">United States</a>, <a href="/wiki/Canada" title="Canada">Canada</a>, and many other countries.<a href="#cite_note-IndexNominum2000-16">[16]</a><a href="#cite_note-Drugs.com-17">[17]</a><a href="#cite_note-Micromedex-18">[18]</a><a href="#cite_note-Martindale-19">[19]</a> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2>[<a href="/w/index.php?title=Gestonorone_caproate&action=edit&section=13" title="Edit section: Research">edit</a>]</div> Gestonorone caproate was studied in the treatment of <a href="/wiki/Prostate_cancer" title="Prostate cancer">prostate cancer</a> in men at a dosage of 400 mg per week by intramuscular injection but, in contrast to the case of <a href="/wiki/Benign_prostatic_hyperplasia" title="Benign prostatic hyperplasia">benign prostatic hyperplasia</a>, was found to be ineffective.<a href="#cite_note-Smith2013-75">[66]</a><a href="#cite_note-SanderNissen-Meyer1977-76">[67]</a> <a href="/wiki/SH-834" class="mw-redirect" title="SH-834">SH-834</a> was a combination of 90 mg <a href="/wiki/Estradiol_valerate" title="Estradiol valerate">estradiol valerate</a> and 300 mg gestonorone caproate for weekly intramuscular injection that was developed by Schering in the 1960s and 1970s.<a href="#cite_note-NotterBerndt2009-77">[68]</a><a href="#cite_note-pmid4555897-22">[22]</a><a href="#cite_note-pmid5088730-78">[69]</a> It was investigated clinically as a treatment for <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a> and was found to be effective.<a href="#cite_note-NotterBerndt2009-77">[68]</a><a href="#cite_note-BerndtStender2009-79">[70]</a><a href="#cite_note-pmid5088730-78">[69]</a> However, its effectiveness was found to be no better than that of an <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogen</a> alone, and the combination was ultimately never marketed.<a href="#cite_note-pmid968923-80">[71]</a> Gestonorone caproate was studied by <a href="/wiki/Schering_AG" title="Schering AG">Schering</a> for use as a <a href="/wiki/Progestogen-only_injectable_contraceptive" title="Progestogen-only injectable contraceptive">progestogen-only injectable contraceptive</a> across a dose range of 2.5 to 200 mg once every one or two months but was never marketed.<a href="#cite_note-pmid865726-70">[61]</a><a href="#cite_note-Toppozada1983-81">[72]</a><a href="#cite_note-Kadam2007-82">[73]</a><a href="#cite_note-pmid12313080-83">[74]</a><a href="#cite_note-pmid4797435-84">[75]</a><a href="#cite_note-HurtadoKesseru1968-85">[76]</a><a href="#cite_note-pmid4732140-86">[77]</a><a href="#cite_note-Restrepo1969-87">[78]</a> There is very little clinical experience of gestonorone caproate for this indication.<a href="#cite_note-pmid865726-70">[61]</a> Gestonorone caproate has been studied in the treatment of <a href="/wiki/Ovarian_cancer" title="Ovarian cancer">ovarian cancer</a> (in combination with <a href="/wiki/Cyclophosphamide" title="Cyclophosphamide">cyclophosphamide</a>),<a href="#cite_note-BruchhausenDannhardt2013-5">[5]</a><a href="#cite_note-pmid4555897-22">[22]</a><a href="#cite_note-pmid476014-88">[79]</a><a href="#cite_note-pmid687544-89">[80]</a> <a href="/wiki/Menstrual_cycle" title="Menstrual cycle">menstrual cycle</a>-related <a href="/wiki/Mouth_ulcer" title="Mouth ulcer">mouth ulcers</a>,<a href="#cite_note-pmid102602-21">[21]</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-pmid340117-69">[60]</a> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2>[<a href="/w/index.php?title=Gestonorone_caproate&action=edit&section=14" title="Edit section: See also">edit</a>]</div> <ul><li><a href="/wiki/Estradiol_valerate/gestonorone_caproate" title="Estradiol valerate/gestonorone caproate">Estradiol valerate/gestonorone caproate</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2>[<a href="/w/index.php?title=Gestonorone_caproate&action=edit&section=15" 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-Muller1998-1">^ <a href="#cite_ref-Muller1998_1-0">a</a> <a href="#cite_ref-Muller1998_1-1">b</a> <a href="#cite_ref-Muller1998_1-2">c</a> <a href="#cite_ref-Muller1998_1-3">d</a> <style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFMuller1998" class="citation book cs1">Muller (19 June 1998). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=HiSdvzs2pPAC&pg=PA338">European Drug Index: European Drug Registrations</a> (Fourth ed.). CRC Press. pp. 338–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-7692-2114-5" title="Special:BookSources/978-3-7692-2114-5"><bdi>978-3-7692-2114-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=European+Drug+Index%3A+European+Drug+Registrations&rft.pages=338-&rft.edition=Fourth&rft.pub=CRC+Press&rft.date=1998-06-19&rft.isbn=978-3-7692-2114-5&rft.au=Muller&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DHiSdvzs2pPAC%26pg%3DPA338&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"> </li> <li id="cite_note-Aronson2009-2"><a href="#cite_ref-Aronson2009_2-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFAronson2009" class="citation book cs1">Aronson JK (21 February 2009). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=BWMeSwVwfTkC&pg=PA289">Meyler's Side Effects of Endocrine and Metabolic Drugs</a>. 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Acta Radiologica. 10 (2): 187–192. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3109%2F02841867109129755">10.3109/02841867109129755</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/5556820">5556820</a>. <q>The preparations used were Proluton Depot (17a-hydroxy-progesterone caproate) and in 3 patients SH 5132 (17a-hydroxy-19-norprogesterone caproate); 100 mg of the latter corresponds to 1000 mg of Proluton Depot.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Radiologica&rft.atitle=Progesterone+treatment+for+local+recurrence+and+metastases+in+carcinoma+corporis+uteri&rft.volume=10&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E187-%3C%2Fspan%3E192&rft.date=1971-04&rft_id=info%3Adoi%2F10.3109%2F02841867109129755&rft_id=info%3Apmid%2F5556820&rft.aulast=Karlstedt&rft.aufirst=K&rft_id=https%3A%2F%2Fdoi.org%2F10.3109%252F02841867109129755&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"> </li> <li id="cite_note-pmid4261828-24">^ <a href="#cite_ref-pmid4261828_24-0">a</a> <a href="#cite_ref-pmid4261828_24-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMoe1972" class="citation journal cs1">Moe N (1972). 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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%3AGestonorone+caproate" class="Z3988"> </li> <li id="cite_note-RaspéBrosig2013-27"><a href="#cite_ref-RaspéBrosig2013_27-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRaspéBrosig2013" class="citation book cs1">Raspé G, Brosig W (22 October 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=8RjLBAAAQBAJ&pg=PA169">International Symposium on the Treatment of Carcinoma of the Prostate, Berlin, November 13 to 15, 1969: Life Science Monographs</a>. Elsevier. p. 169. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4831-8711-2" title="Special:BookSources/978-1-4831-8711-2"><bdi>978-1-4831-8711-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=International+Symposium+on+the+Treatment+of+Carcinoma+of+the+Prostate%2C+Berlin%2C+November+13+to+15%2C+1969%3A+Life+Science+Monographs&rft.pages=169&rft.pub=Elsevier&rft.date=2013-10-22&rft.isbn=978-1-4831-8711-2&rft.aulast=Rasp%C3%A9&rft.aufirst=G&rft.au=Brosig%2C+W&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D8RjLBAAAQBAJ%26pg%3DPA169&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"> </li> <li id="cite_note-MakrigiannisGaca1971-28"><a href="#cite_ref-MakrigiannisGaca1971_28-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMakrigiannisGaca1971" class="citation journal cs1">Makrigiannis D, Gaca A (1971). 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Scandinavian Journal of Urology and Nephrology. 12 (2): 119–121. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3109%2F00365597809179977">10.3109/00365597809179977</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/694436">694436</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Scandinavian+Journal+of+Urology+and+Nephrology&rft.atitle=On+gestagen+treatment+of+advanced+prostatic+carcinoma&rft.volume=12&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E119-%3C%2Fspan%3E121&rft.date=1978&rft_id=info%3Adoi%2F10.3109%2F00365597809179977&rft_id=info%3Apmid%2F694436&rft.aulast=Sander&rft.aufirst=S&rft.au=Nissen-Meyer%2C+R&rft.au=Aakvaag%2C+A&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"> </li> <li id="cite_note-pmid519881-30">^ <a href="#cite_ref-pmid519881_30-0">a</a> <a href="#cite_ref-pmid519881_30-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKjeldPuahKaufmanLoizou1979" class="citation journal cs1">Kjeld JM, Puah CM, Kaufman B, Loizou S, Vlotides J, Gwee HM, et al. 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Clinical Endocrinology. 11 (5): 497–504. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1365-2265.1979.tb03102.x">10.1111/j.1365-2265.1979.tb03102.x</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/519881">519881</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:5836155">5836155</a>. <q>Another synthetic gestogen, 17-hydroxy-19-norprogesterone caproate (Depostat-Schering), 400 mg by i.m. weekly injections suppressed T levels to 25% of pretreatment values (Sander er al., 1978).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Clinical+Endocrinology&rft.atitle=Effects+of+norgestrel+and+ethinyloestradiol+ingestion+on+serum+levels+of+sex+hormones+and+gonadotrophins+in+men&rft.volume=11&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E497-%3C%2Fspan%3E504&rft.date=1979-11&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A5836155%23id-name%3DS2CID&rft_id=info%3Apmid%2F519881&rft_id=info%3Adoi%2F10.1111%2Fj.1365-2265.1979.tb03102.x&rft.aulast=Kjeld&rft.aufirst=JM&rft.au=Puah%2C+CM&rft.au=Kaufman%2C+B&rft.au=Loizou%2C+S&rft.au=Vlotides%2C+J&rft.au=Gwee%2C+HM&rft.au=Kahn%2C+F&rft.au=Sood%2C+R&rft.au=Joplin%2C+GF&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"> </li> <li id="cite_note-WeinKavoussi2011-31"><a href="#cite_ref-WeinKavoussi2011_31-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWeinKavoussiNovickPartin2011" class="citation book cs1">Wein AJ, Kavoussi LR, Novick AC, Partin AW, Peters CA (25 August 2011). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=fu3BBwAAQBAJ&pg=PA2938">Campbell-Walsh Urology: Expert Consult Premium Edition: Enhanced Online Features and Print, 4-Volume Set</a>. 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Springer-Verlag. pp. 583–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-95583-9" title="Special:BookSources/978-3-642-95583-9"><bdi>978-3-642-95583-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Geburtshilfe+und+Gyn%C3%A4kologie%3A+Physiologie+und+Pathologie+der+Reproduktion&rft.pages=583-&rft.pub=Springer-Verlag&rft.date=2013-03-08&rft.isbn=978-3-642-95583-9&rft.aulast=Kn%C3%B6rr&rft.aufirst=K&rft.au=Kn%C3%B6rr-G%C3%A4rtner%2C+H&rft.au=Beller%2C+FK&rft.au=Lauritzen%2C+C&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DtpmgBgAAQBAJ%26pg%3DPA583&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"> </li> <li id="cite_note-Labhart2012-38"><a href="#cite_ref-Labhart2012_38-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLabhart2012" class="citation book cs1">Labhart A (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=DAgJCAAAQBAJ&pg=PA554">Clinical Endocrinology: Theory and Practice</a>. 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%3AGestonorone+caproate" class="Z3988"> </li> <li id="cite_note-HorskyPresl1981-39"><a href="#cite_ref-HorskyPresl1981_39-0">^</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>. 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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%3AGestonorone+caproate" class="Z3988"> </li> <li id="cite_note-Pschyrembel1968r-41"><a href="#cite_ref-Pschyrembel1968r_41-0">^</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%3AGestonorone+caproate" class="Z3988"> </li> <li id="cite_note-Ferin1972-42"><a href="#cite_ref-Ferin1972_42-0">^</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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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%3AGestonorone+caproate" class="Z3988"> </li> <li id="cite_note-MoltzHaase2008-49"><a href="#cite_ref-MoltzHaase2008_49-0">^</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%3AGestonorone+caproate" class="Z3988"> </li> <li id="cite_note-WrightBurgess2012-50"><a href="#cite_ref-WrightBurgess2012_50-0">^</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%3AGestonorone+caproate" class="Z3988"> </li> <li id="cite_note-ChuLi1986-51"><a href="#cite_ref-ChuLi1986_51-0">^</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%3AGestonorone+caproate" class="Z3988"> </li> <li id="cite_note-RunnebaumRabe2012-52"><a href="#cite_ref-RunnebaumRabe2012_52-0">^</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%3AGestonorone+caproate" class="Z3988"> </li> <li id="cite_note-ArtiniGenazzani2001-53"><a href="#cite_ref-ArtiniGenazzani2001_53-0">^</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%3AGestonorone+caproate" class="Z3988"> </li> <li id="cite_note-KingBrucker2013-54"><a href="#cite_ref-KingBrucker2013_54-0">^</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%3AGestonorone+caproate" class="Z3988"> </li> <li id="cite_note-Denis2012-64"><a href="#cite_ref-Denis2012_64-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDenis2012" class="citation book cs1">Denis L (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=T78hBQAAQBAJ&pg=PT112">The Medical Management of Prostate Cancer</a>. Springer Science & Business Media. pp. 112–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-73238-6" title="Special:BookSources/978-3-642-73238-6"><bdi>978-3-642-73238-6</bdi></a>. <q>Gestonorone caproate, another progestational agent, was investigated at our institution. Eighteen patients with painful metastatic [prostate cancer] with objective relapse after orchiectomy were treated with 400 mg/week i.m.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Medical+Management+of+Prostate+Cancer&rft.pages=112-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-3-642-73238-6&rft.aulast=Denis&rft.aufirst=L&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DT78hBQAAQBAJ%26pg%3DPT112&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"> </li> <li id="cite_note-RunnebaumRabe2012a-65"><a href="#cite_ref-RunnebaumRabe2012a_65-0">^</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=GX2oBgAAQBAJ&pg=PA133">Future Aspects in Contraception: Proceeding of an International Symposium held in Heidelberg, 5–8 September 1984 Part 1 Male Contraception</a>. Springer Science & Business Media. pp. 133–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-94-009-4910-2" title="Special:BookSources/978-94-009-4910-2"><bdi>978-94-009-4910-2</bdi></a>. <q>Gestonorone [caproate] 100 or 200 mg/week i.m.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Future+Aspects+in+Contraception%3A+Proceeding+of+an+International+Symposium+held+in+Heidelberg%2C+5%E2%80%938+September+1984+Part+1+Male+Contraception&rft.pages=133-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-94-009-4910-2&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%3DGX2oBgAAQBAJ%26pg%3DPA133&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"> </li> <li id="cite_note-PalancaJuco2008-66"><a href="#cite_ref-PalancaJuco2008_66-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPalancaJuco2008" class="citation journal cs1">Palanca E, Juco W (2008). "Conservative treatment of benign prostatic hyperplasia". Current Medical Research and Opinion. 4 (7): 513–520. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1185%2F03007997709109342">10.1185/03007997709109342</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/66118">66118</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:31798723">31798723</a>. <q>A study was carried out in 30 male patients with benign prostate hyperplasia to assess the effectiveness of treatment with a progestational agent, gestonorone caproate (200 mg), given intramuscularly every 7 days over a period of 2 to 3 months.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Current+Medical+Research+and+Opinion&rft.atitle=Conservative+treatment+of+benign+prostatic+hyperplasia&rft.volume=4&rft.issue=7&rft.pages=%3Cspan+class%3D%22nowrap%22%3E513-%3C%2Fspan%3E520&rft.date=2008&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A31798723%23id-name%3DS2CID&rft_id=info%3Apmid%2F66118&rft_id=info%3Adoi%2F10.1185%2F03007997709109342&rft.aulast=Palanca&rft.aufirst=E&rft.au=Juco%2C+W&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"> </li> <li id="cite_note-Nevinny-Stickel1962-67"><a href="#cite_ref-Nevinny-Stickel1962_67-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFNevinny-Stickel1962" class="citation book cs1">Nevinny-Stickel J (1962). "Die gestagene Wirkung von Hydroxy-nor-Progesteronestern bei der Frau". Gewebs- und Neurohormone [The progestational effects of hydroxy-nor-progesterone esters in women]. Symposion der Deutschen Gesellschaft für Endokrinologie. Springer. pp. 248–255. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-3-642-86860-3_27">10.1007/978-3-642-86860-3_27</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-540-02909-0" title="Special:BookSources/978-3-540-02909-0"><bdi>978-3-540-02909-0</bdi></a>. <q>Das Hydroxy-nor-Progesteron-Capronat stand in öliger Lösung zm intramuskulären Injektion zur Verfügung. Die Wirkungsdauer betrug 10-13 Tage. Nach Verabreichung von 25 mg waren als beginnende Sekretionszeichen (1) an den geschlängelten Drüsen basale Vacuolen der Epithelien zu sehen. Eine volle Umwandlung der Schleimhaut erfolgte erst auf 50 mg des Capronsäureesters (Abb. l und 2).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Die+gestagene+Wirkung+von+Hydroxy-nor-Progesteronestern+bei+der+Frau&rft.btitle=Gewebs-+und+Neurohormone&rft.series=Symposion+der+Deutschen+Gesellschaft+f%C3%BCr+Endokrinologie&rft.pages=%3Cspan+class%3D%22nowrap%22%3E248-%3C%2Fspan%3E255&rft.pub=Springer&rft.date=1962&rft_id=info%3Adoi%2F10.1007%2F978-3-642-86860-3_27&rft.isbn=978-3-540-02909-0&rft.aulast=Nevinny-Stickel&rft.aufirst=J&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"> </li> <li id="cite_note-HorskyPresl1981b-68"><a href="#cite_ref-HorskyPresl1981b_68-0">^</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 J (eds.). Ovarian Function and its Disorders: Diagnosis and Therapy. Developments in Obstetrics and Gynecology. 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.series=Developments+in+Obstetrics+and+Gynecology&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%3AGestonorone+caproate" class="Z3988"> </li> <li id="cite_note-pmid340117-69">^ <a href="#cite_ref-pmid340117_69-0">a</a> <a href="#cite_ref-pmid340117_69-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLindsayHartPurdieFerguson1978" class="citation journal cs1">Lindsay R, Hart DM, Purdie D, Ferguson MM, Clark AS, Kraszewski A (February 1978). "Comparative effects of oestrogen and a progestogen on bone loss in postmenopausal women". Clinical Science and Molecular Medicine. 54 (2): 193–195. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1042%2Fcs0540193">10.1042/cs0540193</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/340117">340117</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:1799407">1799407</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Clinical+Science+and+Molecular+Medicine&rft.atitle=Comparative+effects+of+oestrogen+and+a+progestogen+on+bone+loss+in+postmenopausal+women&rft.volume=54&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E193-%3C%2Fspan%3E195&rft.date=1978-02&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A1799407%23id-name%3DS2CID&rft_id=info%3Apmid%2F340117&rft_id=info%3Adoi%2F10.1042%2Fcs0540193&rft.aulast=Lindsay&rft.aufirst=R&rft.au=Hart%2C+DM&rft.au=Purdie%2C+D&rft.au=Ferguson%2C+MM&rft.au=Clark%2C+AS&rft.au=Kraszewski%2C+A&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"> </li> <li id="cite_note-pmid865726-70">^ <a href="#cite_ref-pmid865726_70-0">a</a> <a href="#cite_ref-pmid865726_70-1">b</a> <a href="#cite_ref-pmid865726_70-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFToppozada1977" class="citation journal cs1">Toppozada M (June 1977). 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Revista Colombiana de Obstetricia y Ginecologia. 20: 247–255. Archived from <a rel="nofollow" class="external text" href="https://www.popline.org/node/479231">the original</a> on 2018-09-19.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Revista+Colombiana+de+Obstetricia+y+Ginecologia&rft.atitle=17-alpha-hydroxy+19+norprogesterone+capronate+as+a+prolonged-action+injectable+contraceptive+agent.&rft.volume=20&rft.pages=%3Cspan+class%3D%22nowrap%22%3E247-%3C%2Fspan%3E255&rft.date=1969&rft.aulast=Rodriguez-Restrepo&rft.aufirst=R&rft_id=https%3A%2F%2Fwww.popline.org%2Fnode%2F479231&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"> </li> <li id="cite_note-pmid476014-88"><a href="#cite_ref-pmid476014_88-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFGuthrie1979" class="citation journal cs1">Guthrie D (July 1979). 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British Journal of Obstetrics and Gynaecology. 86 (7): 497–500. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1471-0528.1979.tb10799.x">10.1111/j.1471-0528.1979.tb10799.x</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/476014">476014</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:31408925">31408925</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=British+Journal+of+Obstetrics+and+Gynaecology&rft.atitle=The+treatment+of+advanced+cystadenocarcinoma+of+the+ovary+with+gestronol+and+continuous+oral+cyclophosphamide&rft.volume=86&rft.issue=7&rft.pages=%3Cspan+class%3D%22nowrap%22%3E497-%3C%2Fspan%3E500&rft.date=1979-07&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A31408925%23id-name%3DS2CID&rft_id=info%3Apmid%2F476014&rft_id=info%3Adoi%2F10.1111%2Fj.1471-0528.1979.tb10799.x&rft.aulast=Guthrie&rft.aufirst=D&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"> </li> <li id="cite_note-pmid687544-89"><a href="#cite_ref-pmid687544_89-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDarwish1978" class="citation journal cs1">Darwish DH (August 1978). "The effect of sex steroids on the in vitro synthesis of DNA by malignant ovarian tumours". British Journal of Obstetrics and Gynaecology. 85 (8): 627–633. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1471-0528.1978.tb14933.x">10.1111/j.1471-0528.1978.tb14933.x</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/687544">687544</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:30816473">30816473</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=British+Journal+of+Obstetrics+and+Gynaecology&rft.atitle=The+effect+of+sex+steroids+on+the+in+vitro+synthesis+of+DNA+by+malignant+ovarian+tumours&rft.volume=85&rft.issue=8&rft.pages=%3Cspan+class%3D%22nowrap%22%3E627-%3C%2Fspan%3E633&rft.date=1978-08&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A30816473%23id-name%3DS2CID&rft_id=info%3Apmid%2F687544&rft_id=info%3Adoi%2F10.1111%2Fj.1471-0528.1978.tb14933.x&rft.aulast=Darwish&rft.aufirst=DH&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"> </li> </ol></div></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><style data-mw-deduplicate="TemplateStyles:r1236075235">.mw-parser-output .navbox{box-sizing:border-box;border:1px solid #a2a9b1;width:100%;clear:both;font-size:88%;text-align:center;padding:1px;margin:1em auto 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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 href="/wiki/Dydrogesterone" title="Dydrogesterone">Dydrogesterone</a></li> <li><a href="/wiki/Trengestone" title="Trengestone">Trengestone</a></li></ul> <ul><li>17α-Hydroxyprogesterone (and closely related) derivatives: 17α-Hydroxylated: <a href="/wiki/Acetomepregenol" title="Acetomepregenol">Acetomepregenol (mepregenol diacetate)</a></li> <li><a href="/wiki/Algestone_acetophenide" title="Algestone acetophenide">Algestone acetophenide (dihydroxyprogesterone acetophenide)</a></li> <li><a href="/wiki/Anagestone_acetate" title="Anagestone acetate">Anagestone acetate</a></li> <li><a href="/wiki/Chlormadinone_acetate" title="Chlormadinone acetate">Chlormadinone acetate</a></li> <li><a href="/wiki/Chlormethenmadinone_acetate" title="Chlormethenmadinone acetate">Chlormethenmadinone acetate</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Delmadinone_acetate" title="Delmadinone acetate">Delmadinone acetate</a></li> <li><a href="/wiki/Flugestone_acetate" title="Flugestone acetate">Flugestone acetate (flurogestone acetate)</a></li> <li><a href="/wiki/Flumedroxone_acetate" title="Flumedroxone acetate">Flumedroxone acetate</a></li> <li><a href="/wiki/Hydroxyprogesterone_acetate" title="Hydroxyprogesterone acetate">Hydroxyprogesterone acetate</a></li> <li><a href="/wiki/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">Hydroxyprogesterone caproate</a></li> <li><a href="/wiki/Hydroxyprogesterone_heptanoate" title="Hydroxyprogesterone heptanoate">Hydroxyprogesterone heptanoate</a></li> <li><a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">Medroxyprogesterone acetate</a>#</li> <li><a href="/wiki/Megestrol_acetate" title="Megestrol acetate">Megestrol acetate</a></li> <li><a href="/wiki/Melengestrol_acetate" title="Melengestrol acetate">Melengestrol acetate</a></li> <li><a href="/wiki/Methenmadinone_acetate" title="Methenmadinone acetate">Methenmadinone acetate</a></li> <li><a href="/wiki/Osaterone_acetate" title="Osaterone acetate">Osaterone acetate</a></li> <li><a href="/wiki/Pentagestrone_acetate" title="Pentagestrone acetate">Pentagestrone acetate</a></li> <li><a href="/wiki/Proligestone" title="Proligestone">Proligestone</a>; 17α-Methylated: <a href="/wiki/Medrogestone" title="Medrogestone">Medrogestone</a>; Others: <a href="/wiki/Haloprogesterone" title="Haloprogesterone">Haloprogesterone</a></li></ul> <ul><li>19-Norprogesterone derivatives: 17α-Hydroxylated: <a class="mw-selflink selflink">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="Drugs_used_in_benign_prostatic_hyperplasia_(G04C)191" 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:Drugs_used_in_benign_prostatic_hypertrophy" title="Template:Drugs used in benign prostatic hypertrophy"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Drugs_used_in_benign_prostatic_hypertrophy" title="Template talk:Drugs used in benign prostatic hypertrophy"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Drugs_used_in_benign_prostatic_hypertrophy" title="Special:EditPage/Template:Drugs used in benign prostatic hypertrophy"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Drugs_used_in_benign_prostatic_hyperplasia_(G04C)191" style="font-size:114%;margin:0 4em">Drugs used in <a href="/wiki/Benign_prostatic_hyperplasia" title="Benign prostatic hyperplasia">benign prostatic hyperplasia</a> (<a href="/wiki/ATC_code_G04#G04C" title="ATC code G04">G04C</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/5%CE%B1-Reductase_inhibitor" title="5α-Reductase inhibitor">5α-Reductase inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Dutasteride" title="Dutasteride">Dutasteride</a></li> <li><a href="/wiki/Epristeride" title="Epristeride">Epristeride</a></li> <li><a href="/wiki/Finasteride" title="Finasteride">Finasteride</a> (<a href="/wiki/Finasteride/tadalafil" title="Finasteride/tadalafil">+tadalafil</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Alpha-1_blocker" title="Alpha-1 blocker">Alpha-1 blockers</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alfuzosin" title="Alfuzosin">Alfuzosin</a></li> <li><a href="/wiki/Doxazosin" title="Doxazosin">Doxazosin</a></li> <li><a href="/wiki/Silodosin" title="Silodosin">Silodosin</a></li> <li><a href="/wiki/Tamsulosin" title="Tamsulosin">Tamsulosin</a></li> <li><a href="/wiki/Terazosin" title="Terazosin">Terazosin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Steroidal_antiandrogen" title="Steroidal antiandrogen">Steroidal antiandrogens</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Allylestrenol" title="Allylestrenol">Allylestrenol</a></li> <li><a href="/wiki/Delmadinone_acetate" title="Delmadinone acetate">Delmadinone acetate</a></li> <li><a class="mw-selflink selflink">Gestonorone caproate</a></li> <li><a href="/wiki/Osaterone_acetate" title="Osaterone acetate">Osaterone acetate</a></li> <li><a href="/wiki/Oxendolone" title="Oxendolone">Oxendolone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Herbal_medicine" title="Herbal medicine">Herbal products</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Pygeum_(herbal_remedy)" class="mw-redirect" title="Pygeum (herbal remedy)">Pygeum africanum</a></li> <li><a href="/wiki/Saw_palmetto_extract" title="Saw palmetto extract">Saw palmetto extract</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Mepartricin" title="Mepartricin">Mepartricin</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Progesterone_receptor_modulators1654" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Progesterone_receptor_modulators" title="Template:Progesterone receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Progesterone_receptor_modulators" title="Template talk:Progesterone receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Progesterone_receptor_modulators" title="Special:EditPage/Template:Progesterone receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Progesterone_receptor_modulators1654" style="font-size:114%;margin:0 4em"><a href="/wiki/Progesterone_receptor" title="Progesterone receptor">Progesterone receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Progesterone_receptor" title="Progesterone receptor"><abbr title="Progesterone receptor">PR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Progesterone receptor</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Progesterone derivatives: <a href="/wiki/3%CE%B2-Dihydroprogesterone" title="3β-Dihydroprogesterone">3β-Dihydroprogesterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">5α-Dihydroprogesterone</a></li> <li><a href="/wiki/6%CE%B1-Methylprogesterone" title="6α-Methylprogesterone">6α-Methylprogesterone</a></li> <li><a href="/wiki/9%CE%B1-Bromo-11-ketoprogesterone" class="mw-redirect" title="9α-Bromo-11-ketoprogesterone">9α-Bromo-11-ketoprogesterone</a></li> <li><a href="/wiki/11-Dehydroprogesterone" title="11-Dehydroprogesterone">11-Dehydroprogesterone</a></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyprogesterone" title="16α-Hydroxyprogesterone">16α-Hydroxyprogesterone</a></li> <li><a href="/w/index.php?title=17%CE%B1-Methyl-11-deoxycorticosterone_acetate&action=edit&redlink=1" class="new" title="17α-Methyl-11-deoxycorticosterone acetate (page does not exist)">17α-Methyl-11-deoxycorticosterone acetate</a></li> <li><a href="/wiki/20%CE%B1-Dihydroprogesterone" title="20α-Dihydroprogesterone">20α-Dihydroprogesterone</a></li> <li><a href="/wiki/20%CE%B2-Dihydroprogesterone" title="20β-Dihydroprogesterone">20β-Dihydroprogesterone</a></li> <li><a href="/wiki/Dimepregnen" title="Dimepregnen">Dimepregnen</a></li> <li><a href="/wiki/Diosgenin" title="Diosgenin">Diosgenin</a></li> <li><a href="/wiki/P1-185" title="P1-185">P1-185</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Progesterone_3-acetyl_enol_ether" title="Progesterone 3-acetyl enol ether">Progesterone 3-acetyl enol ether</a></li> <li><a href="/wiki/Quingestrone" title="Quingestrone">Quingestrone</a></li></ul> <ul><li>Retroprogesterone derivatives: <a href="/wiki/20%CE%B1-Dihydrodydrogesterone" title="20α-Dihydrodydrogesterone">20α-Dihydrodydrogesterone</a></li> <li><a href="/wiki/20%CE%B1-Dihydrotrengestone" title="20α-Dihydrotrengestone">20α-Dihydrotrengestone</a></li> <li><a href="/wiki/DU-41164" title="DU-41164">DU-41164</a></li> <li><a href="/wiki/DU-41165" title="DU-41165">DU-41165</a></li> <li><a href="/wiki/Dydrogesterone" title="Dydrogesterone">Dydrogesterone</a></li> <li><a href="/wiki/Retroprogesterone" title="Retroprogesterone">Retroprogesterone</a></li> <li><a href="/wiki/Ro_6-3129" title="Ro 6-3129">Ro 6-3129</a></li> <li><a href="/wiki/Trengestone" title="Trengestone">Trengestone</a></li></ul> <ul><li>17α-Substituted progesterone derivatives: <a href="/wiki/6%CE%B1-Methyl-17%CE%B1-bromoprogesterone" title="6α-Methyl-17α-bromoprogesterone">6α-Methyl-17α-bromoprogesterone</a></li> <li><a href="/wiki/15%CE%B2-Hydroxycyproterone_acetate" title="15β-Hydroxycyproterone acetate">15β-Hydroxycyproterone acetate</a></li> <li><a href="/wiki/16-Methylene-17%CE%B1-hydroxyprogesterone_acetate" title="16-Methylene-17α-hydroxyprogesterone acetate">16-Methylene-17α-hydroxyprogesterone acetate</a></li> <li><a href="/wiki/17%CE%B1-Bromoprogesterone" title="17α-Bromoprogesterone">17α-Bromoprogesterone</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone (hydroxyprogesterone)</a></li> <li><a href="/wiki/17%CE%B1-Methylprogesterone" title="17α-Methylprogesterone">17α-Methylprogesterone</a></li> <li><a href="/wiki/Acetomepregenol" title="Acetomepregenol">Acetomepregenol (mepregenol diacetate)</a></li> <li><a href="/wiki/Algestone" title="Algestone">Algestone</a></li> <li><a href="/wiki/Algestone_acetonide" title="Algestone acetonide">Algestone acetonide</a></li> <li><a href="/wiki/Algestone_acetophenide" title="Algestone acetophenide">Algestone acetophenide</a></li> <li><a href="/wiki/Anagestone" title="Anagestone">Anagestone</a></li> <li><a href="/wiki/Anagestone_acetate" title="Anagestone acetate">Anagestone acetate</a></li> <li><a href="/w/index.php?title=Bromethenmadinone&action=edit&redlink=1" class="new" title="Bromethenmadinone (page does not exist)">Bromethenmadinone</a></li> <li><a href="/wiki/Bromethenmadinone_acetate" title="Bromethenmadinone acetate">Bromethenmadinone acetate</a></li> <li><a href="/wiki/Butagest" title="Butagest">Butagest (buterol)</a></li> <li><a href="/wiki/Chlormadinone" title="Chlormadinone">Chlormadinone</a></li> <li><a href="/wiki/Chlormadinone_acetate" title="Chlormadinone acetate">Chlormadinone acetate</a></li> <li><a href="/wiki/Chlormadinone_caproate" title="Chlormadinone caproate">Chlormadinone caproate</a></li> <li><a href="/w/index.php?title=Chlormethenmadinone&action=edit&redlink=1" class="new" title="Chlormethenmadinone (page does not exist)">Chlormethenmadinone</a></li> <li><a href="/wiki/Chlormethenmadinone_acetate" title="Chlormethenmadinone acetate">Chlormethenmadinone acetate</a></li> <li><a href="/wiki/Cismadinone" title="Cismadinone">Cismadinone</a></li> <li><a href="/wiki/Cismadinone_acetate" title="Cismadinone acetate">Cismadinone acetate</a></li> <li><a href="/wiki/Clogestone" title="Clogestone">Clogestone</a></li> <li><a href="/wiki/Clogestone_acetate" title="Clogestone acetate">Clogestone acetate</a></li> <li><a href="/wiki/Clomegestone" title="Clomegestone">Clomegestone</a></li> <li><a href="/wiki/Clomegestone_acetate" title="Clomegestone acetate">Clomegestone acetate</a></li> <li><a href="/wiki/Cymegesolate" title="Cymegesolate">Cymegesolate</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Delmadinone" title="Delmadinone">Delmadinone</a></li> <li><a href="/wiki/Delmadinone_acetate" title="Delmadinone acetate">Delmadinone acetate</a></li> <li><a href="/wiki/Edogestrone" title="Edogestrone">Edogestrone</a></li> <li><a href="/wiki/Flugestone" title="Flugestone">Flugestone</a></li> <li><a href="/wiki/Flugestone_acetate" title="Flugestone acetate">Flugestone acetate</a></li> <li><a href="/wiki/Fluorometholone" title="Fluorometholone">Fluorometholone</a></li> <li><a href="/wiki/Fluorometholone_acetate" title="Fluorometholone acetate">Fluorometholone acetate</a></li> <li><a href="/wiki/Flumedroxone" title="Flumedroxone">Flumedroxone</a></li> <li><a href="/wiki/Flumedroxone_acetate" title="Flumedroxone acetate">Flumedroxone acetate</a></li> <li><a href="/wiki/Fluoromedroxyprogesterone_acetate" title="Fluoromedroxyprogesterone acetate">Fluoromedroxyprogesterone acetate</a></li> <li><a href="/wiki/Gestaclone" title="Gestaclone">Gestaclone</a></li> <li><a href="/w/index.php?title=Gestobutanoyl&action=edit&redlink=1" class="new" title="Gestobutanoyl (page does not exist)">Gestobutanoyl</a></li> <li><a href="/wiki/Haloprogesterone" title="Haloprogesterone">Haloprogesterone</a></li> <li><a href="/wiki/Hydromadinone" title="Hydromadinone">Hydromadinone</a></li> <li><a href="/wiki/Hydromadinone_acetate" title="Hydromadinone acetate">Hydromadinone acetate</a></li> <li><a href="/wiki/Hydroxyprogesterone_acetate" title="Hydroxyprogesterone acetate">Hydroxyprogesterone acetate</a></li> <li><a href="/wiki/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">Hydroxyprogesterone caproate (hydroxyprogesterone hexanoate)</a></li> <li><a href="/wiki/Hydroxyprogesterone_heptanoate" title="Hydroxyprogesterone heptanoate">Hydroxyprogesterone heptanoate (hydroxyprogesterone enanthate)</a></li> <li><a href="/wiki/Hydroxyprogesterone_heptanoate_benzilic_acid_hydrazone" title="Hydroxyprogesterone heptanoate benzilic acid hydrazone">Hydroxyprogesterone heptanoate benzilic acid hydrazone</a></li> <li><a href="/wiki/Mecigestone" title="Mecigestone">Mecigestone (pentarane B)</a></li> <li><a href="/wiki/Medrogestone" title="Medrogestone">Medrogestone</a></li> <li><a href="/wiki/Medroxyprogesterone" title="Medroxyprogesterone">Medroxyprogesterone</a></li> <li><a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">Medroxyprogesterone acetate</a></li> <li><a href="/wiki/Medroxyprogesterone_caproate" title="Medroxyprogesterone caproate">Medroxyprogesterone caproate</a></li> <li><a href="/wiki/Megestrol" title="Megestrol">Megestrol</a></li> <li><a href="/wiki/Megestrol_acetate" title="Megestrol acetate">Megestrol acetate</a></li> <li><a href="/wiki/Megestrol_caproate" title="Megestrol caproate">Megestrol caproate</a></li> <li><a href="/wiki/Melengestrol" title="Melengestrol">Melengestrol</a></li> <li><a href="/wiki/Melengestrol_acetate" title="Melengestrol acetate">Melengestrol acetate</a></li> <li><a href="/wiki/Methenmadinone" title="Methenmadinone">Methenmadinone</a></li> <li><a href="/wiki/Methenmadinone_acetate" title="Methenmadinone acetate">Methenmadinone acetate</a></li> <li><a href="/wiki/Methenmadinone_caproate" title="Methenmadinone caproate">Methenmadinone caproate</a></li> <li><a href="/wiki/Mometasone" title="Mometasone">Mometasone</a></li> <li><a href="/wiki/Mometasone_furoate" class="mw-redirect" title="Mometasone furoate">Mometasone furoate</a></li> <li><a href="/wiki/Osaterone" title="Osaterone">Osaterone</a></li> <li><a href="/wiki/Osaterone_acetate" title="Osaterone acetate">Osaterone acetate</a></li> <li><a href="/wiki/Pentagestrone" title="Pentagestrone">Pentagestrone</a></li> <li><a href="/wiki/Pentagestrone_acetate" title="Pentagestrone acetate">Pentagestrone acetate</a></li> <li><a href="/wiki/Pentarane_A" title="Pentarane A">Pentarane A</a></li> <li><a href="/wiki/Proligestone" title="Proligestone">Proligestone</a></li> <li><a href="/wiki/Triamcinolone_acetonide" title="Triamcinolone acetonide">Triamcinolone acetonide</a></li></ul> <ul><li>19-Norprogesterone derivatives: <a href="/wiki/17%CE%B1-Methyl-19-norprogesterone" title="17α-Methyl-19-norprogesterone">17α-Methyl-19-norprogesterone</a></li> <li><a href="/wiki/18-Methylsegesterone_acetate" title="18-Methylsegesterone acetate">18-Methylsegesterone acetate</a></li> <li><a href="/wiki/19-Norprogesterone" title="19-Norprogesterone">19-Norprogesterone</a></li> <li><a href="/wiki/Amadinone" title="Amadinone">Amadinone</a></li> <li><a href="/wiki/Amadinone_acetate" title="Amadinone acetate">Amadinone acetate</a></li> <li><a href="/wiki/Demegestone" title="Demegestone">Demegestone</a></li> <li><a href="/w/index.php?title=Fluoro_ethyl_norprogesterone&action=edit&redlink=1" class="new" title="Fluoro ethyl norprogesterone (page does not exist)">Fluoro ethyl norprogesterone</a></li> <li><a href="/w/index.php?title=Fluoro_furanyl_norprogesterone&action=edit&redlink=1" class="new" title="Fluoro furanyl norprogesterone (page does not exist)">Fluoro furanyl norprogesterone</a></li> <li><a href="/wiki/Gestadienol" title="Gestadienol">Gestadienol</a></li> <li><a href="/wiki/Gestadienol_acetate" title="Gestadienol acetate">Gestadienol acetate</a></li> <li><a href="/wiki/Gestonorone_acetate" title="Gestonorone acetate">Gestonorone acetate (gestronol acetate)</a></li> <li><a class="mw-selflink selflink">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><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=Gestonorone_caproate&oldid=1274159829">https://en.wikipedia.org/w/index.php?title=Gestonorone_caproate&oldid=1274159829</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:5%CE%B1-Reductase_inhibitors" title="Category:5α-Reductase inhibitors">5α-Reductase inhibitors</a></li><li><a href="/wiki/Category:Antigonadotropins" title="Category:Antigonadotropins">Antigonadotropins</a></li><li><a href="/wiki/Category:Caproate_esters" title="Category:Caproate esters">Caproate esters</a></li><li><a href="/wiki/Category:Diketones" title="Category:Diketones">Diketones</a></li><li><a href="/wiki/Category:Drugs_for_benign_prostatic_hyperplasia" title="Category:Drugs for benign prostatic hyperplasia">Drugs for benign prostatic hyperplasia</a></li><li><a href="/wiki/Category:Enantiopure_drugs" title="Category:Enantiopure drugs">Enantiopure drugs</a></li><li><a href="/wiki/Category:Hormonal_antineoplastic_drugs" title="Category:Hormonal antineoplastic drugs">Hormonal antineoplastic drugs</a></li><li><a href="/wiki/Category:Norpregnanes" title="Category:Norpregnanes">Norpregnanes</a></li><li><a href="/wiki/Category:Progestogen_esters" 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