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Gestonorone caproate - Wikipedia

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.mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Gestonorone caproate">Gestonorone caproate</span></caption><tbody><tr><td colspan="2" class="infobox-image"><span class="dark_mode_safe" typeof="mw:File"><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></span></td></tr><tr><td colspan="2" class="infobox-image"><span class="dark_mode_safe" typeof="mw:File"><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></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">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; Norhydroxy&#173;progesterone 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<br />administration</a></th><td class="infobox-data"><a href="/wiki/Intramuscular_injection" title="Intramuscular injection">Intramuscular injection</a><sup id="cite_ref-Muller1998_1-0" class="reference"><a href="#cite_note-Muller1998-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Aronson2009_2-0" class="reference"><a href="#cite_note-Aronson2009-2"><span class="cite-bracket">&#91;</span>2<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-MortonHall2012_3-0" class="reference"><a href="#cite_note-MortonHall2012-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_class" title="Drug class">Drug class</a></th><td class="infobox-data"><a href="/wiki/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>&#x20;(<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=G03DA01">WHO</a></span>)&#x20;<br /><a href="/wiki/ATC_code_L02" title="ATC code L02">L02AB03</a>&#x20;(<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=L02AB03">WHO</a></span>)</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&#160;general: ℞&#160;(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<sup id="cite_ref-pmid4285463_4-0" class="reference"><a href="#cite_note-pmid4285463-4"><span class="cite-bracket">&#91;</span>4<span class="cite-bracket">&#93;</span></a></sup><br /><abbr title="Intramuscular injection">IM</abbr>: High<sup id="cite_ref-BruchhausenDannhardt2013_5-0" class="reference"><a href="#cite_note-BruchhausenDannhardt2013-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup></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)<sup id="cite_ref-Springer2013_6-2" class="reference"><a href="#cite_note-Springer2013-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup></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<sup id="cite_ref-Springer2013_6-0" class="reference"><a href="#cite_note-Springer2013-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup><br /><span style="font-size:99%;">• 19-Norpregnanediol-20-one<sup id="cite_ref-Springer2013_6-1" class="reference"><a href="#cite_note-Springer2013-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup></span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Biological_half-life" title="Biological half-life">Elimination <span class="nowrap">half-life</span></a></th><td class="infobox-data"><abbr title="Intramuscular injection">IM</abbr>: 7.5 ± 3.1&#160;days<sup id="cite_ref-BruchhausenDannhardt2013_5-1" class="reference"><a href="#cite_note-BruchhausenDannhardt2013-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup></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&#160;days<sup id="cite_ref-BruchhausenDannhardt2013_5-2" class="reference"><a href="#cite_note-BruchhausenDannhardt2013-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup></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%<sup id="cite_ref-BruchhausenDannhardt2013_5-3" class="reference"><a href="#cite_note-BruchhausenDannhardt2013-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup><br /><a href="/wiki/Feces" title="Feces">Feces</a>: 72%<sup id="cite_ref-BruchhausenDannhardt2013_5-4" class="reference"><a href="#cite_note-BruchhausenDannhardt2013-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">[(8<i>R</i>,9<i>S</i>,10<i>R</i>,13<i>S</i>,14<i>S</i>,17<i>R</i>)-17-acetyl-13-methyl-3-oxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[<i>a</i>]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><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=1253-28-7">1253-28-7</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <span style="font-weight:normal"><abbr title="Compound ID">CID</abbr></span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/443881">443881</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB14677">DB14677</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.391969.html">391969</a></span><sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/U38E620NS6">U38E620NS6</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/KEGG" title="KEGG">KEGG</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D01159">D01159</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:31650">CHEBI:31650</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL2107389">ChEMBL2107389</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID40871837">DTXSID40871837</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><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></span></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.013.646">100.013.646</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><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></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data"><span title="Carbon">C</span><sub>26</sub><span title="Hydrogen">H</span><sub>38</sub><span title="Oxygen">O</span><sub>4</sub></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data"><span class="nowrap"><span data-sort-value="7002414586000000000♠"></span>414.586</span>&#160;g·mol<sup>−1</sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CCCCCC%28%3DO%29OC1%28CCC2C1%28CCC3C2CCC4%3DCC%28%3DO%29CCC34%29C%29C%28%3DO%29C">Interactive image</a></span></li></ul></div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">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> <p><b>Gestonorone caproate</b>, also known as <b>gestronol hexanoate</b> or <b>norhydroxyprogesterone caproate</b> and sold under the brand names <b>Depostat</b> and <b>Primostat</b>, 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>.<sup id="cite_ref-BruchhausenDannhardt2013_5-5" class="reference"><a href="#cite_note-BruchhausenDannhardt2013-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-MortonHall2012_3-1" class="reference"><a href="#cite_note-MortonHall2012-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Publishing2013_7-0" class="reference"><a href="#cite_note-Publishing2013-7"><span class="cite-bracket">&#91;</span>7<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Muller1998_1-1" class="reference"><a href="#cite_note-Muller1998-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Thurston2006_8-0" class="reference"><a href="#cite_note-Thurston2006-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup> It is given by <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">injection into muscle</a> typically once a week.<sup id="cite_ref-pmid4285463_4-1" class="reference"><a href="#cite_note-pmid4285463-4"><span class="cite-bracket">&#91;</span>4<span class="cite-bracket">&#93;</span></a></sup> </p><p><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>.<sup id="cite_ref-BruchhausenDannhardt2013_5-6" class="reference"><a href="#cite_note-BruchhausenDannhardt2013-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> 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>.<sup id="cite_ref-Raspé2013_9-0" class="reference"><a href="#cite_note-Raspé2013-9"><span class="cite-bracket">&#91;</span>9<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-SchooneesDe_Klerk1969_10-0" class="reference"><a href="#cite_note-SchooneesDe_Klerk1969-10"><span class="cite-bracket">&#91;</span>10<span class="cite-bracket">&#93;</span></a></sup> It has no other important <a href="/wiki/Hormonal_agent" class="mw-redirect" title="Hormonal agent">hormonal</a> activity.<sup id="cite_ref-BruchhausenDannhardt2013_5-7" class="reference"><a href="#cite_note-BruchhausenDannhardt2013-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-HorskyPresl1981a_11-0" class="reference"><a href="#cite_note-HorskyPresl1981a-11"><span class="cite-bracket">&#91;</span>11<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Schering1968_12-0" class="reference"><a href="#cite_note-Schering1968-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-AubreyKhosla1971_13-0" class="reference"><a href="#cite_note-AubreyKhosla1971-13"><span class="cite-bracket">&#91;</span>13<span class="cite-bracket">&#93;</span></a></sup> </p><p>Gestonorone caproate was discovered in 1960 and was introduced for medical use by 1973.<sup id="cite_ref-Kaiser1960_14-0" class="reference"><a href="#cite_note-Kaiser1960-14"><span class="cite-bracket">&#91;</span>14<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-SubbiahMortensen1973_15-0" class="reference"><a href="#cite_note-SubbiahMortensen1973-15"><span class="cite-bracket">&#91;</span>15<span class="cite-bracket">&#93;</span></a></sup> 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>.<sup id="cite_ref-Muller1998_1-2" class="reference"><a href="#cite_note-Muller1998-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-IndexNominum2000_16-0" class="reference"><a href="#cite_note-IndexNominum2000-16"><span class="cite-bracket">&#91;</span>16<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Drugs.com_17-0" class="reference"><a href="#cite_note-Drugs.com-17"><span class="cite-bracket">&#91;</span>17<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Micromedex_18-0" class="reference"><a href="#cite_note-Micromedex-18"><span class="cite-bracket">&#91;</span>18<span class="cite-bracket">&#93;</span></a></sup> 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>.<sup id="cite_ref-Micromedex_18-1" class="reference"><a href="#cite_note-Micromedex-18"><span class="cite-bracket">&#91;</span>18<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Martindale_19-0" class="reference"><a href="#cite_note-Martindale-19"><span class="cite-bracket">&#91;</span>19<span class="cite-bracket">&#93;</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Medical_uses">Medical uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Gestonorone_caproate&amp;action=edit&amp;section=1" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>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>.<sup id="cite_ref-BruchhausenDannhardt2013_5-8" class="reference"><a href="#cite_note-BruchhausenDannhardt2013-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-MortonHall2012_3-2" class="reference"><a href="#cite_note-MortonHall2012-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-SmithWilliams2005_20-0" class="reference"><a href="#cite_note-SmithWilliams2005-20"><span class="cite-bracket">&#91;</span>20<span class="cite-bracket">&#93;</span></a></sup> It is used at a dose of 100 to 200&#160;mg once a week by <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">intramuscular injection</a>.<sup id="cite_ref-BruchhausenDannhardt2013_5-9" class="reference"><a href="#cite_note-BruchhausenDannhardt2013-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Side_effects">Side effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Gestonorone_caproate&amp;action=edit&amp;section=2" title="Edit section: Side effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Progestin#Side_effects" class="mw-redirect" title="Progestin">Progestin §&#160;Side effects</a></div> <p><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>.<sup id="cite_ref-BruchhausenDannhardt2013_5-10" class="reference"><a href="#cite_note-BruchhausenDannhardt2013-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Gestonorone_caproate&amp;action=edit&amp;section=3" title="Edit section: Pharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Pharmacodynamics">Pharmacodynamics</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Gestonorone_caproate&amp;action=edit&amp;section=4" title="Edit section: Pharmacodynamics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>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>,<sup id="cite_ref-Raspé2013_9-1" class="reference"><a href="#cite_note-Raspé2013-9"><span class="cite-bracket">&#91;</span>9<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-SchooneesDe_Klerk1969_10-1" class="reference"><a href="#cite_note-SchooneesDe_Klerk1969-10"><span class="cite-bracket">&#91;</span>10<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-AubreyKhosla1971_13-1" class="reference"><a href="#cite_note-AubreyKhosla1971-13"><span class="cite-bracket">&#91;</span>13<span class="cite-bracket">&#93;</span></a></sup> 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.<sup id="cite_ref-BruchhausenDannhardt2013_5-11" class="reference"><a href="#cite_note-BruchhausenDannhardt2013-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-HorskyPresl1981a_11-1" class="reference"><a href="#cite_note-HorskyPresl1981a-11"><span class="cite-bracket">&#91;</span>11<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Schering1968_12-1" class="reference"><a href="#cite_note-Schering1968-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-AubreyKhosla1971_13-2" class="reference"><a href="#cite_note-AubreyKhosla1971-13"><span class="cite-bracket">&#91;</span>13<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid102602_21-0" class="reference"><a href="#cite_note-pmid102602-21"><span class="cite-bracket">&#91;</span>21<span class="cite-bracket">&#93;</span></a></sup> It is approximately 20 to 25&#160;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>.<sup id="cite_ref-BruchhausenDannhardt2013_5-12" class="reference"><a href="#cite_note-BruchhausenDannhardt2013-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-AubreyKhosla1971_13-3" class="reference"><a href="#cite_note-AubreyKhosla1971-13"><span class="cite-bracket">&#91;</span>13<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid4555897_22-0" class="reference"><a href="#cite_note-pmid4555897-22"><span class="cite-bracket">&#91;</span>22<span class="cite-bracket">&#93;</span></a></sup> In humans, 100 or 200&#160;mg intramuscular gestonorone caproate has been said to be equivalent to 1,000&#160;mg intramuscular hydroxyprogesterone caproate.<sup id="cite_ref-pmid5556820_23-0" class="reference"><a href="#cite_note-pmid5556820-23"><span class="cite-bracket">&#91;</span>23<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid4261828_24-0" class="reference"><a href="#cite_note-pmid4261828-24"><span class="cite-bracket">&#91;</span>24<span class="cite-bracket">&#93;</span></a></sup> Hence, gestonorone caproate is approximately 5- to 10-fold more potent than hydroxyprogesterone caproate in humans.<sup id="cite_ref-HorskyPresl1981a_11-2" class="reference"><a href="#cite_note-HorskyPresl1981a-11"><span class="cite-bracket">&#91;</span>11<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid5556820_23-1" class="reference"><a href="#cite_note-pmid5556820-23"><span class="cite-bracket">&#91;</span>23<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid4261828_24-1" class="reference"><a href="#cite_note-pmid4261828-24"><span class="cite-bracket">&#91;</span>24<span class="cite-bracket">&#93;</span></a></sup> The <a href="/wiki/Biological_effect" class="mw-redirect" title="Biological effect">biological effects</a> of gestonorone caproate in women have been studied.<sup id="cite_ref-JürgensenTaubert1969_25-0" class="reference"><a href="#cite_note-JürgensenTaubert1969-25"><span class="cite-bracket">&#91;</span>25<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Ferin1972a_26-0" class="reference"><a href="#cite_note-Ferin1972a-26"><span class="cite-bracket">&#91;</span>26<span class="cite-bracket">&#93;</span></a></sup> </p><p>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>.<sup id="cite_ref-AubreyKhosla1971_13-4" class="reference"><a href="#cite_note-AubreyKhosla1971-13"><span class="cite-bracket">&#91;</span>13<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-RaspéBrosig2013_27-0" class="reference"><a href="#cite_note-RaspéBrosig2013-27"><span class="cite-bracket">&#91;</span>27<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-MakrigiannisGaca1971_28-0" class="reference"><a href="#cite_note-MakrigiannisGaca1971-28"><span class="cite-bracket">&#91;</span>28<span class="cite-bracket">&#93;</span></a></sup> A clinical study found that 400&#160;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%.<sup id="cite_ref-pmid694436_29-0" class="reference"><a href="#cite_note-pmid694436-29"><span class="cite-bracket">&#91;</span>29<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid519881_30-0" class="reference"><a href="#cite_note-pmid519881-30"><span class="cite-bracket">&#91;</span>30<span class="cite-bracket">&#93;</span></a></sup> Levels of <a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone">luteinizing hormone</a>, conversely, remained unchanged.<sup id="cite_ref-pmid694436_29-1" class="reference"><a href="#cite_note-pmid694436-29"><span class="cite-bracket">&#91;</span>29<span class="cite-bracket">&#93;</span></a></sup> In general, progestogens can maximally suppress testosterone levels by about 70 to 80%.<sup id="cite_ref-WeinKavoussi2011_31-0" class="reference"><a href="#cite_note-WeinKavoussi2011-31"><span class="cite-bracket">&#91;</span>31<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid6237116_32-0" class="reference"><a href="#cite_note-pmid6237116-32"><span class="cite-bracket">&#91;</span>32<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid7000222_33-0" class="reference"><a href="#cite_note-pmid7000222-33"><span class="cite-bracket">&#91;</span>33<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid694436_29-2" class="reference"><a href="#cite_note-pmid694436-29"><span class="cite-bracket">&#91;</span>29<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid519881_30-1" class="reference"><a href="#cite_note-pmid519881-30"><span class="cite-bracket">&#91;</span>30<span class="cite-bracket">&#93;</span></a></sup> 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>.<sup id="cite_ref-BruchhausenDannhardt2013_5-13" class="reference"><a href="#cite_note-BruchhausenDannhardt2013-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> </p><p><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.<sup id="cite_ref-Springer2013_6-3" class="reference"><a href="#cite_note-Springer2013-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup> 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.<sup id="cite_ref-Springer2013_6-4" class="reference"><a href="#cite_note-Springer2013-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup> </p><p>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.<sup id="cite_ref-BruchhausenDannhardt2013_5-14" class="reference"><a href="#cite_note-BruchhausenDannhardt2013-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> 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.<sup id="cite_ref-BruchhausenDannhardt2013_5-15" class="reference"><a href="#cite_note-BruchhausenDannhardt2013-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> Gestonorone caproate decreases the uptake of testosterone into the prostate gland.<sup id="cite_ref-BruchhausenDannhardt2013_5-16" class="reference"><a href="#cite_note-BruchhausenDannhardt2013-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> 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> <i><a href="/wiki/In_vitro" title="In vitro">in vitro</a></i>.<sup id="cite_ref-BruchhausenDannhardt2013_5-17" class="reference"><a href="#cite_note-BruchhausenDannhardt2013-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> </p><p>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.<sup id="cite_ref-pmid64267_34-0" class="reference"><a href="#cite_note-pmid64267-34"><span class="cite-bracket">&#91;</span>34<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid1177428_35-0" class="reference"><a href="#cite_note-pmid1177428-35"><span class="cite-bracket">&#91;</span>35<span class="cite-bracket">&#93;</span></a></sup> </p> <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 dd,.mw-parser-output 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"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<sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">&#91;</span>a<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-56" class="reference"><a href="#cite_note-56"><span class="cite-bracket">&#91;</span>b<span class="cite-bracket">&#93;</span></a></sup> </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)<sup id="cite_ref-57" class="reference"><a href="#cite_note-57"><span class="cite-bracket">&#91;</span>c<span class="cite-bracket">&#93;</span></a></sup> </th> <th scope="col" rowspan="2"><abbr title="Duration of action">DOA</abbr><sup id="cite_ref-58" class="reference"><a href="#cite_note-58"><span class="cite-bracket">&#91;</span>d<span class="cite-bracket">&#93;</span></a></sup> </th></tr> <tr> <th scope="col"><abbr title="Endometrial transformation dose">TFD</abbr><sup id="cite_ref-59" class="reference"><a href="#cite_note-59"><span class="cite-bracket">&#91;</span>e<span class="cite-bracket">&#93;</span></a></sup> </th> <th scope="col"><abbr title="Progestogen-only injectable contraceptive dose">POICD</abbr><sup id="cite_ref-60" class="reference"><a href="#cite_note-60"><span class="cite-bracket">&#91;</span>f<span class="cite-bracket">&#93;</span></a></sup> </th> <th scope="col"><abbr title="Combined injectable contraceptive dose">CICD</abbr><sup id="cite_ref-61" class="reference"><a href="#cite_note-61"><span class="cite-bracket">&#91;</span>g<span class="cite-bracket">&#93;</span></a></sup> </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><sup id="cite_ref-mark_62-0" class="reference"><a href="#cite_note-mark-62"><span class="cite-bracket">&#91;</span>h<span class="cite-bracket">&#93;</span></a></sup></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<sup id="cite_ref-div_63-0" class="reference"><a href="#cite_note-div-63"><span class="cite-bracket">&#91;</span>i<span class="cite-bracket">&#93;</span></a></sup></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>&gt;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<sup id="cite_ref-div_63-1" class="reference"><a href="#cite_note-div-63"><span class="cite-bracket">&#91;</span>i<span class="cite-bracket">&#93;</span></a></sup></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"><span class="mw-cite-backlink"><b><a href="#cite_ref-55">^</a></b></span> <span class="reference-text"><b>Sources:</b> <sup id="cite_ref-KnörrBeller2013_36-0" class="reference"><a href="#cite_note-KnörrBeller2013-36"><span class="cite-bracket">&#91;</span>36<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-KnörrKnörr-Gärtner2013y_37-0" class="reference"><a href="#cite_note-KnörrKnörr-Gärtner2013y-37"><span class="cite-bracket">&#91;</span>37<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Labhart2012_38-0" class="reference"><a href="#cite_note-Labhart2012-38"><span class="cite-bracket">&#91;</span>38<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-HorskyPresl1981_39-0" class="reference"><a href="#cite_note-HorskyPresl1981-39"><span class="cite-bracket">&#91;</span>39<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Ufer1969_40-0" class="reference"><a href="#cite_note-Ufer1969-40"><span class="cite-bracket">&#91;</span>40<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Pschyrembel1968r_41-0" class="reference"><a href="#cite_note-Pschyrembel1968r-41"><span class="cite-bracket">&#91;</span>41<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Ferin1972_42-0" class="reference"><a href="#cite_note-Ferin1972-42"><span class="cite-bracket">&#91;</span>42<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-HenzlEdwards1999u_43-0" class="reference"><a href="#cite_note-HenzlEdwards1999u-43"><span class="cite-bracket">&#91;</span>43<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Brotherton1976_44-0" class="reference"><a href="#cite_note-Brotherton1976-44"><span class="cite-bracket">&#91;</span>44<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid8013220_45-0" class="reference"><a href="#cite_note-pmid8013220-45"><span class="cite-bracket">&#91;</span>45<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid8013216_46-0" class="reference"><a href="#cite_note-pmid8013216-46"><span class="cite-bracket">&#91;</span>46<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Goebelsmann1986_47-0" class="reference"><a href="#cite_note-Goebelsmann1986-47"><span class="cite-bracket">&#91;</span>47<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-BeckerDüsterberg1980_48-0" class="reference"><a href="#cite_note-BeckerDüsterberg1980-48"><span class="cite-bracket">&#91;</span>48<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-MoltzHaase2008_49-0" class="reference"><a href="#cite_note-MoltzHaase2008-49"><span class="cite-bracket">&#91;</span>49<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-WrightBurgess2012_50-0" class="reference"><a href="#cite_note-WrightBurgess2012-50"><span class="cite-bracket">&#91;</span>50<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-ChuLi1986_51-0" class="reference"><a href="#cite_note-ChuLi1986-51"><span class="cite-bracket">&#91;</span>51<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-RunnebaumRabe2012_52-0" class="reference"><a href="#cite_note-RunnebaumRabe2012-52"><span class="cite-bracket">&#91;</span>52<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-ArtiniGenazzani2001_53-0" class="reference"><a href="#cite_note-ArtiniGenazzani2001-53"><span class="cite-bracket">&#91;</span>53<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-KingBrucker2013_54-0" class="reference"><a href="#cite_note-KingBrucker2013-54"><span class="cite-bracket">&#91;</span>54<span class="cite-bracket">&#93;</span></a></sup></span> </li> <li id="cite_note-56"><span class="mw-cite-backlink"><b><a href="#cite_ref-56">^</a></b></span> <span class="reference-text">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>.</span> </li> <li id="cite_note-57"><span class="mw-cite-backlink"><b><a href="#cite_ref-57">^</a></b></span> <span class="reference-text">Progesterone production during the <a href="/wiki/Luteal_phase" title="Luteal phase">luteal phase</a> is ~25&#160;(15–50)&#160;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</span> of OHPC is 250 to 500&#160;mg/month.</span> </li> <li id="cite_note-58"><span class="mw-cite-backlink"><b><a href="#cite_ref-58">^</a></b></span> <span class="reference-text">Duration of action in days.</span> </li> <li id="cite_note-59"><span class="mw-cite-backlink"><b><a href="#cite_ref-59">^</a></b></span> <span class="reference-text">Usually given for 14 days.</span> </li> <li id="cite_note-60"><span class="mw-cite-backlink"><b><a href="#cite_ref-60">^</a></b></span> <span class="reference-text">Usually dosed every two to three months.</span> </li> <li id="cite_note-61"><span class="mw-cite-backlink"><b><a href="#cite_ref-61">^</a></b></span> <span class="reference-text">Usually dosed once monthly.</span> </li> <li id="cite_note-mark-62"><span class="mw-cite-backlink"><b><a href="#cite_ref-mark_62-0">^</a></b></span> <span class="reference-text">Never marketed or approved by this route.</span> </li> <li id="cite_note-div-63"><span class="mw-cite-backlink">^ <a href="#cite_ref-div_63-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-div_63-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text">In divided doses (2 × 125 or 250&#160;mg for <abbr title="hydroxyprogesterone caproate">OHPC</abbr>, 10 × 20&#160;mg for <abbr title="progesterone">P4</abbr>).</span> </li> </ol></div></div></div></div> </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Pharmacokinetics">Pharmacokinetics</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Gestonorone_caproate&amp;action=edit&amp;section=5" title="Edit section: Pharmacokinetics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>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>.<sup id="cite_ref-pmid4285463_4-2" class="reference"><a href="#cite_note-pmid4285463-4"><span class="cite-bracket">&#91;</span>4<span class="cite-bracket">&#93;</span></a></sup> 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.<sup id="cite_ref-BruchhausenDannhardt2013_5-18" class="reference"><a href="#cite_note-BruchhausenDannhardt2013-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Denis2012_64-0" class="reference"><a href="#cite_note-Denis2012-64"><span class="cite-bracket">&#91;</span>55<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-RunnebaumRabe2012a_65-0" class="reference"><a href="#cite_note-RunnebaumRabe2012a-65"><span class="cite-bracket">&#91;</span>56<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-PalancaJuco2008_66-0" class="reference"><a href="#cite_note-PalancaJuco2008-66"><span class="cite-bracket">&#91;</span>57<span class="cite-bracket">&#93;</span></a></sup> After an intramuscular injection, gestonorone caproate is completely released from the local depot and is highly <a href="/wiki/Bioavailability" title="Bioavailability">bioavailable</a>.<sup id="cite_ref-BruchhausenDannhardt2013_5-19" class="reference"><a href="#cite_note-BruchhausenDannhardt2013-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> A single <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">intramuscular injection</a> of 25 to 50&#160;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&#160;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.<sup id="cite_ref-Ferin1972a_26-1" class="reference"><a href="#cite_note-Ferin1972a-26"><span class="cite-bracket">&#91;</span>26<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Nevinny-Stickel1962_67-0" class="reference"><a href="#cite_note-Nevinny-Stickel1962-67"><span class="cite-bracket">&#91;</span>58<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-HorskyPresl1981b_68-0" class="reference"><a href="#cite_note-HorskyPresl1981b-68"><span class="cite-bracket">&#91;</span>59<span class="cite-bracket">&#93;</span></a></sup> 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&#160;days.<sup id="cite_ref-BruchhausenDannhardt2013_5-20" class="reference"><a href="#cite_note-BruchhausenDannhardt2013-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> 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.<sup id="cite_ref-pmid340117_69-0" class="reference"><a href="#cite_note-pmid340117-69"><span class="cite-bracket">&#91;</span>60<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid865726_70-0" class="reference"><a href="#cite_note-pmid865726-70"><span class="cite-bracket">&#91;</span>61<span class="cite-bracket">&#93;</span></a></sup> </p><p>Following a single intramuscular injection of 200&#160;mg <a href="/wiki/Radiolabel" class="mw-redirect" title="Radiolabel">radiolabeled</a> gestonorone caproate in 1&#160;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&#160;days and were 420 ± 160&#160;ng/mL.<sup id="cite_ref-BruchhausenDannhardt2013_5-21" class="reference"><a href="#cite_note-BruchhausenDannhardt2013-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> 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&#160;days.<sup id="cite_ref-BruchhausenDannhardt2013_5-22" class="reference"><a href="#cite_note-BruchhausenDannhardt2013-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> 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.<sup id="cite_ref-BruchhausenDannhardt2013_5-23" class="reference"><a href="#cite_note-BruchhausenDannhardt2013-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> 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>.<sup id="cite_ref-BruchhausenDannhardt2013_5-24" class="reference"><a href="#cite_note-BruchhausenDannhardt2013-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> 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>.<sup id="cite_ref-BruchhausenDannhardt2013_5-25" class="reference"><a href="#cite_note-BruchhausenDannhardt2013-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-NagelKolb1973_71-0" class="reference"><a href="#cite_note-NagelKolb1973-71"><span class="cite-bracket">&#91;</span>62<span class="cite-bracket">&#93;</span></a></sup> Approximately 48 ± 18% of the injected dose had been eliminated after 14&#160;days and approximately 85 ± 12% of the injected dose had been excreted after 30&#160;days.<sup id="cite_ref-BruchhausenDannhardt2013_5-26" class="reference"><a href="#cite_note-BruchhausenDannhardt2013-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> </p><p>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.<sup id="cite_ref-Springer2013_6-5" class="reference"><a href="#cite_note-Springer2013-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup> 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>.<sup id="cite_ref-Springer2013_6-6" class="reference"><a href="#cite_note-Springer2013-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup> 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.<sup id="cite_ref-Springer2013_6-7" class="reference"><a href="#cite_note-Springer2013-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup> 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.<sup id="cite_ref-Springer2013_6-8" class="reference"><a href="#cite_note-Springer2013-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup> 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.<sup id="cite_ref-Springer2013_6-9" class="reference"><a href="#cite_note-Springer2013-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid102602_21-1" class="reference"><a href="#cite_note-pmid102602-21"><span class="cite-bracket">&#91;</span>21<span class="cite-bracket">&#93;</span></a></sup> 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.<sup id="cite_ref-Springer2013_6-10" class="reference"><a href="#cite_note-Springer2013-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup> Following an intramuscular injection of 300&#160;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.<sup id="cite_ref-Springer2013_6-11" class="reference"><a href="#cite_note-Springer2013-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup> <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.<sup id="cite_ref-Springer2013_6-12" class="reference"><a href="#cite_note-Springer2013-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Gestonorone_caproate&amp;action=edit&amp;section=6" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/List_of_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> <p>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>.<sup id="cite_ref-Elks2014_72-0" class="reference"><a href="#cite_note-Elks2014-72"><span class="cite-bracket">&#91;</span>63<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-IndexNominum2000_16-1" class="reference"><a href="#cite_note-IndexNominum2000-16"><span class="cite-bracket">&#91;</span>16<span class="cite-bracket">&#93;</span></a></sup> 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.<sup id="cite_ref-Elks2014_72-1" class="reference"><a href="#cite_note-Elks2014-72"><span class="cite-bracket">&#91;</span>63<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-IndexNominum2000_16-2" class="reference"><a href="#cite_note-IndexNominum2000-16"><span class="cite-bracket">&#91;</span>16<span class="cite-bracket">&#93;</span></a></sup> <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>.<sup id="cite_ref-Elks2014_72-2" class="reference"><a href="#cite_note-Elks2014-72"><span class="cite-bracket">&#91;</span>63<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-IndexNominum2000_16-3" class="reference"><a href="#cite_note-IndexNominum2000-16"><span class="cite-bracket">&#91;</span>16<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Synthesis">Synthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Gestonorone_caproate&amp;action=edit&amp;section=7" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Chemical_synthesis" title="Chemical synthesis">Chemical syntheses</a> of gestonorone caproate have been published.<sup id="cite_ref-BruchhausenDannhardt2013_5-27" class="reference"><a href="#cite_note-BruchhausenDannhardt2013-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Publishing2013_7-1" class="reference"><a href="#cite_note-Publishing2013-7"><span class="cite-bracket">&#91;</span>7<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-KleemannEngel2001_73-0" class="reference"><a href="#cite_note-KleemannEngel2001-73"><span class="cite-bracket">&#91;</span>64<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Gestonorone_caproate&amp;action=edit&amp;section=8" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Gestonorone caproate was first described in 1960.<sup id="cite_ref-Kaiser1960_14-1" class="reference"><a href="#cite_note-Kaiser1960-14"><span class="cite-bracket">&#91;</span>14<span class="cite-bracket">&#93;</span></a></sup> It was developed by <a href="/wiki/Schering_AG" title="Schering AG">Schering</a> and has been marketed since at least 1968.<sup id="cite_ref-Schering1968_12-2" class="reference"><a href="#cite_note-Schering1968-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-SubbiahMortensen1973_15-1" class="reference"><a href="#cite_note-SubbiahMortensen1973-15"><span class="cite-bracket">&#91;</span>15<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Gestonorone_caproate&amp;action=edit&amp;section=9" title="Edit section: Society and culture"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Generic_names">Generic names</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Gestonorone_caproate&amp;action=edit&amp;section=10" title="Edit section: Generic names"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><i>Gestonorone caproate</i> is the <a href="/wiki/Generic_term" class="mw-redirect" title="Generic term">generic name</a> of the drug and its <a href="/wiki/International_Nonproprietary_Name" class="mw-redirect" title="International Nonproprietary Name"><abbr title="International Nonproprietary Name">INN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip International Nonproprietary Name</span>, <a href="/wiki/United_States_Adopted_Name" title="United States Adopted Name"><abbr title="United States Adopted Name">USAN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip United States Adopted Name</span>, and <a href="/wiki/Japanese_Accepted_Name" title="Japanese Accepted Name"><abbr title="Japanese Accepted Name">JAN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Japanese Accepted Name</span>, while <i>gestronol hexanoate</i> 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</span>.<sup id="cite_ref-Elks2014_72-3" class="reference"><a href="#cite_note-Elks2014-72"><span class="cite-bracket">&#91;</span>63<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-IndexNominum2000_16-4" class="reference"><a href="#cite_note-IndexNominum2000-16"><span class="cite-bracket">&#91;</span>16<span class="cite-bracket">&#93;</span></a></sup> It has also been referred to as <i>norhydroxyprogesterone caproate</i>, and is also known by its former developmental code names <i>SH-582</i> and <i>SH-80582</i>.<sup id="cite_ref-Elks2014_72-4" class="reference"><a href="#cite_note-Elks2014-72"><span class="cite-bracket">&#91;</span>63<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-IndexNominum2000_16-5" class="reference"><a href="#cite_note-IndexNominum2000-16"><span class="cite-bracket">&#91;</span>16<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Drugs.com_17-1" class="reference"><a href="#cite_note-Drugs.com-17"><span class="cite-bracket">&#91;</span>17<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Brand_names">Brand names</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Gestonorone_caproate&amp;action=edit&amp;section=11" title="Edit section: Brand names"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Gestonorone caproate has been marketed exclusively under the brand names Depostat and Primostat.<sup id="cite_ref-Elks2014_72-5" class="reference"><a href="#cite_note-Elks2014-72"><span class="cite-bracket">&#91;</span>63<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-IndexNominum2000_16-6" class="reference"><a href="#cite_note-IndexNominum2000-16"><span class="cite-bracket">&#91;</span>16<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Drugs.com_17-2" class="reference"><a href="#cite_note-Drugs.com-17"><span class="cite-bracket">&#91;</span>17<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Micromedex_18-2" class="reference"><a href="#cite_note-Micromedex-18"><span class="cite-bracket">&#91;</span>18<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Martindale_19-1" class="reference"><a href="#cite_note-Martindale-19"><span class="cite-bracket">&#91;</span>19<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Availability">Availability</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Gestonorone_caproate&amp;action=edit&amp;section=12" title="Edit section: Availability"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File: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> <p>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.<sup id="cite_ref-Muller1998_1-3" class="reference"><a href="#cite_note-Muller1998-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-IndexNominum2000_16-7" class="reference"><a href="#cite_note-IndexNominum2000-16"><span class="cite-bracket">&#91;</span>16<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Drugs.com_17-3" class="reference"><a href="#cite_note-Drugs.com-17"><span class="cite-bracket">&#91;</span>17<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Micromedex_18-3" class="reference"><a href="#cite_note-Micromedex-18"><span class="cite-bracket">&#91;</span>18<span class="cite-bracket">&#93;</span></a></sup> 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>.<sup id="cite_ref-Micromedex_18-4" class="reference"><a href="#cite_note-Micromedex-18"><span class="cite-bracket">&#91;</span>18<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Martindale_19-2" class="reference"><a href="#cite_note-Martindale-19"><span class="cite-bracket">&#91;</span>19<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-MHRA_74-0" class="reference"><a href="#cite_note-MHRA-74"><span class="cite-bracket">&#91;</span>65<span class="cite-bracket">&#93;</span></a></sup> 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.<sup id="cite_ref-IndexNominum2000_16-8" class="reference"><a href="#cite_note-IndexNominum2000-16"><span class="cite-bracket">&#91;</span>16<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Drugs.com_17-4" class="reference"><a href="#cite_note-Drugs.com-17"><span class="cite-bracket">&#91;</span>17<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Micromedex_18-5" class="reference"><a href="#cite_note-Micromedex-18"><span class="cite-bracket">&#91;</span>18<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Martindale_19-3" class="reference"><a href="#cite_note-Martindale-19"><span class="cite-bracket">&#91;</span>19<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Gestonorone_caproate&amp;action=edit&amp;section=13" title="Edit section: Research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>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&#160;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.<sup id="cite_ref-Smith2013_75-0" class="reference"><a href="#cite_note-Smith2013-75"><span class="cite-bracket">&#91;</span>66<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-SanderNissen-Meyer1977_76-0" class="reference"><a href="#cite_note-SanderNissen-Meyer1977-76"><span class="cite-bracket">&#91;</span>67<span class="cite-bracket">&#93;</span></a></sup> </p><p><a href="/wiki/SH-834" class="mw-redirect" title="SH-834">SH-834</a> was a combination of 90&#160;mg <a href="/wiki/Estradiol_valerate" title="Estradiol valerate">estradiol valerate</a> and 300&#160;mg gestonorone caproate for weekly intramuscular injection that was developed by Schering in the 1960s and 1970s.<sup id="cite_ref-NotterBerndt2009_77-0" class="reference"><a href="#cite_note-NotterBerndt2009-77"><span class="cite-bracket">&#91;</span>68<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid4555897_22-1" class="reference"><a href="#cite_note-pmid4555897-22"><span class="cite-bracket">&#91;</span>22<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid5088730_78-0" class="reference"><a href="#cite_note-pmid5088730-78"><span class="cite-bracket">&#91;</span>69<span class="cite-bracket">&#93;</span></a></sup> 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.<sup id="cite_ref-NotterBerndt2009_77-1" class="reference"><a href="#cite_note-NotterBerndt2009-77"><span class="cite-bracket">&#91;</span>68<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-BerndtStender2009_79-0" class="reference"><a href="#cite_note-BerndtStender2009-79"><span class="cite-bracket">&#91;</span>70<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid5088730_78-1" class="reference"><a href="#cite_note-pmid5088730-78"><span class="cite-bracket">&#91;</span>69<span class="cite-bracket">&#93;</span></a></sup> 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.<sup id="cite_ref-pmid968923_80-0" class="reference"><a href="#cite_note-pmid968923-80"><span class="cite-bracket">&#91;</span>71<span class="cite-bracket">&#93;</span></a></sup> </p><p>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&#160;mg once every one or two months but was never marketed.<sup id="cite_ref-pmid865726_70-1" class="reference"><a href="#cite_note-pmid865726-70"><span class="cite-bracket">&#91;</span>61<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Toppozada1983_81-0" class="reference"><a href="#cite_note-Toppozada1983-81"><span class="cite-bracket">&#91;</span>72<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Kadam2007_82-0" class="reference"><a href="#cite_note-Kadam2007-82"><span class="cite-bracket">&#91;</span>73<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid12313080_83-0" class="reference"><a href="#cite_note-pmid12313080-83"><span class="cite-bracket">&#91;</span>74<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid4797435_84-0" class="reference"><a href="#cite_note-pmid4797435-84"><span class="cite-bracket">&#91;</span>75<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-HurtadoKesseru1968_85-0" class="reference"><a href="#cite_note-HurtadoKesseru1968-85"><span class="cite-bracket">&#91;</span>76<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid4732140_86-0" class="reference"><a href="#cite_note-pmid4732140-86"><span class="cite-bracket">&#91;</span>77<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Restrepo1969_87-0" class="reference"><a href="#cite_note-Restrepo1969-87"><span class="cite-bracket">&#91;</span>78<span class="cite-bracket">&#93;</span></a></sup> There is very little clinical experience of gestonorone caproate for this indication.<sup id="cite_ref-pmid865726_70-2" class="reference"><a href="#cite_note-pmid865726-70"><span class="cite-bracket">&#91;</span>61<span class="cite-bracket">&#93;</span></a></sup> </p><p>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>),<sup id="cite_ref-BruchhausenDannhardt2013_5-28" class="reference"><a href="#cite_note-BruchhausenDannhardt2013-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid4555897_22-2" class="reference"><a href="#cite_note-pmid4555897-22"><span class="cite-bracket">&#91;</span>22<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid476014_88-0" class="reference"><a href="#cite_note-pmid476014-88"><span class="cite-bracket">&#91;</span>79<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid687544_89-0" class="reference"><a href="#cite_note-pmid687544-89"><span class="cite-bracket">&#91;</span>80<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Menstrual_cycle" title="Menstrual cycle">menstrual cycle</a>-related <a href="/wiki/Mouth_ulcer" title="Mouth ulcer">mouth ulcers</a>,<sup id="cite_ref-pmid102602_21-2" class="reference"><a href="#cite_note-pmid102602-21"><span class="cite-bracket">&#91;</span>21<span class="cite-bracket">&#93;</span></a></sup> and as a component of <a href="/wiki/Menopausal_hormone_therapy" class="mw-redirect" title="Menopausal hormone therapy">menopausal hormone therapy</a>.<sup id="cite_ref-pmid340117_69-1" class="reference"><a href="#cite_note-pmid340117-69"><span class="cite-bracket">&#91;</span>60<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Gestonorone_caproate&amp;action=edit&amp;section=14" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></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><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Gestonorone_caproate&amp;action=edit&amp;section=15" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626" /><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-Muller1998-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Muller1998_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Muller1998_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Muller1998_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Muller1998_1-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFMuller1998" class="citation book cs1">Muller (19 June 1998). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=HiSdvzs2pPAC&amp;pg=PA338"><i>European Drug Index: European Drug Registrations</i></a> (Fourth&#160;ed.). CRC Press. pp.&#160;338–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<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&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=European+Drug+Index%3A+European+Drug+Registrations&amp;rft.pages=338-&amp;rft.edition=Fourth&amp;rft.pub=CRC+Press&amp;rft.date=1998-06-19&amp;rft.isbn=978-3-7692-2114-5&amp;rft.au=Muller&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DHiSdvzs2pPAC%26pg%3DPA338&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-Aronson2009-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-Aronson2009_2-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFAronson2009" class="citation book cs1">Aronson JK (21 February 2009). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=BWMeSwVwfTkC&amp;pg=PA289"><i>Meyler's Side Effects of Endocrine and Metabolic Drugs</i></a>. Elsevier. pp.&#160;289–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-0-08-093292-7" title="Special:BookSources/978-0-08-093292-7"><bdi>978-0-08-093292-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Meyler%27s+Side+Effects+of+Endocrine+and+Metabolic+Drugs&amp;rft.pages=289-&amp;rft.pub=Elsevier&amp;rft.date=2009-02-21&amp;rft.isbn=978-0-08-093292-7&amp;rft.aulast=Aronson&amp;rft.aufirst=JK&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DBWMeSwVwfTkC%26pg%3DPA289&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-MortonHall2012-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-MortonHall2012_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-MortonHall2012_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-MortonHall2012_3-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMortonHall2012" class="citation book cs1">Morton IK, Hall JM (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=tsjrCAAAQBAJ&amp;pg=PA132"><i>Concise Dictionary of Pharmacological Agents: Properties and Synonyms</i></a>. Springer Science &amp; Business Media. pp.&#160;132–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-94-011-4439-1" title="Special:BookSources/978-94-011-4439-1"><bdi>978-94-011-4439-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Concise+Dictionary+of+Pharmacological+Agents%3A+Properties+and+Synonyms&amp;rft.pages=132-&amp;rft.pub=Springer+Science+%26+Business+Media&amp;rft.date=2012-12-06&amp;rft.isbn=978-94-011-4439-1&amp;rft.aulast=Morton&amp;rft.aufirst=IK&amp;rft.au=Hall%2C+JM&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DtsjrCAAAQBAJ%26pg%3DPA132&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-pmid4285463-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid4285463_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid4285463_4-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-pmid4285463_4-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBreuerLisboa1966" class="citation journal cs1 cs1-prop-foreign-lang-source">Breuer H, Lisboa BP (January 1966). "[Studies on the metabolism of 17-alpha-hydroxy-19-norprogesterone caproate by humans in vivo and of 17-alpha-hydroxy-19-norprogesterone by rats in vitro]" &#91;Studies on the metabolism of 17-alpha-hydroxy-19-norprogesterone caproate by humans in vivo and of 17-alpha-hydroxy-19-norprogesterone by rats in vitro&#93;. <i>Acta Endocrinologica</i> (in German). <b>51</b> (1): <span class="nowrap">114–</span>130. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1530%2Facta.0.0510114">10.1530/acta.0.0510114</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/4285463">4285463</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Acta+Endocrinologica&amp;rft.atitle=%5BStudies+on+the+metabolism+of+17-alpha-hydroxy-19-norprogesterone+caproate+by+humans+in+vivo+and+of+17-alpha-hydroxy-19-norprogesterone+by+rats+in+vitro%5D&amp;rft.volume=51&amp;rft.issue=1&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E114-%3C%2Fspan%3E130&amp;rft.date=1966-01&amp;rft_id=info%3Adoi%2F10.1530%2Facta.0.0510114&amp;rft_id=info%3Apmid%2F4285463&amp;rft.aulast=Breuer&amp;rft.aufirst=H&amp;rft.au=Lisboa%2C+BP&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-BruchhausenDannhardt2013-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-BruchhausenDannhardt2013_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-BruchhausenDannhardt2013_5-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-BruchhausenDannhardt2013_5-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-BruchhausenDannhardt2013_5-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-BruchhausenDannhardt2013_5-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-BruchhausenDannhardt2013_5-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-BruchhausenDannhardt2013_5-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-BruchhausenDannhardt2013_5-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-BruchhausenDannhardt2013_5-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-BruchhausenDannhardt2013_5-9"><sup><i><b>j</b></i></sup></a> <a href="#cite_ref-BruchhausenDannhardt2013_5-10"><sup><i><b>k</b></i></sup></a> <a href="#cite_ref-BruchhausenDannhardt2013_5-11"><sup><i><b>l</b></i></sup></a> <a href="#cite_ref-BruchhausenDannhardt2013_5-12"><sup><i><b>m</b></i></sup></a> <a href="#cite_ref-BruchhausenDannhardt2013_5-13"><sup><i><b>n</b></i></sup></a> <a href="#cite_ref-BruchhausenDannhardt2013_5-14"><sup><i><b>o</b></i></sup></a> <a href="#cite_ref-BruchhausenDannhardt2013_5-15"><sup><i><b>p</b></i></sup></a> <a href="#cite_ref-BruchhausenDannhardt2013_5-16"><sup><i><b>q</b></i></sup></a> <a href="#cite_ref-BruchhausenDannhardt2013_5-17"><sup><i><b>r</b></i></sup></a> <a href="#cite_ref-BruchhausenDannhardt2013_5-18"><sup><i><b>s</b></i></sup></a> <a href="#cite_ref-BruchhausenDannhardt2013_5-19"><sup><i><b>t</b></i></sup></a> <a href="#cite_ref-BruchhausenDannhardt2013_5-20"><sup><i><b>u</b></i></sup></a> <a href="#cite_ref-BruchhausenDannhardt2013_5-21"><sup><i><b>v</b></i></sup></a> <a href="#cite_ref-BruchhausenDannhardt2013_5-22"><sup><i><b>w</b></i></sup></a> <a href="#cite_ref-BruchhausenDannhardt2013_5-23"><sup><i><b>x</b></i></sup></a> <a href="#cite_ref-BruchhausenDannhardt2013_5-24"><sup><i><b>y</b></i></sup></a> <a href="#cite_ref-BruchhausenDannhardt2013_5-25"><sup><i><b>z</b></i></sup></a> <a href="#cite_ref-BruchhausenDannhardt2013_5-26"><sup><i><b>aa</b></i></sup></a> <a href="#cite_ref-BruchhausenDannhardt2013_5-27"><sup><i><b>ab</b></i></sup></a> <a href="#cite_ref-BruchhausenDannhardt2013_5-28"><sup><i><b>ac</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFvon_BruchhausenDannhardtEbelFrahm2013" class="citation book cs1">von Bruchhausen F, Dannhardt G, Ebel S, Frahm AW, Hackenthal E, Holzgrabe U (2 July 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=8vSjBgAAQBAJ&amp;pg=PA343"><i>Hagers Handbuch der Pharmazeutischen Praxis: Band 8: Stoffe E-O</i></a>. Springer-Verlag. pp.&#160;343–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-3-642-57994-3" title="Special:BookSources/978-3-642-57994-3"><bdi>978-3-642-57994-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Hagers+Handbuch+der+Pharmazeutischen+Praxis%3A+Band+8%3A+Stoffe+E-O&amp;rft.pages=343-&amp;rft.pub=Springer-Verlag&amp;rft.date=2013-07-02&amp;rft.isbn=978-3-642-57994-3&amp;rft.aulast=von+Bruchhausen&amp;rft.aufirst=F&amp;rft.au=Dannhardt%2C+G&amp;rft.au=Ebel%2C+S&amp;rft.au=Frahm%2C+AW&amp;rft.au=Hackenthal%2C+E&amp;rft.au=Holzgrabe%2C+U&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D8vSjBgAAQBAJ%26pg%3DPA343&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-Springer2013-6"><span class="mw-cite-backlink">^ <a href="#cite_ref-Springer2013_6-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Springer2013_6-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Springer2013_6-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Springer2013_6-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Springer2013_6-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-Springer2013_6-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-Springer2013_6-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-Springer2013_6-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-Springer2013_6-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-Springer2013_6-9"><sup><i><b>j</b></i></sup></a> <a href="#cite_ref-Springer2013_6-10"><sup><i><b>k</b></i></sup></a> <a href="#cite_ref-Springer2013_6-11"><sup><i><b>l</b></i></sup></a> <a href="#cite_ref-Springer2013_6-12"><sup><i><b>m</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation book cs1"><a rel="nofollow" class="external text" href="https://books.google.com/books?id=t8GpBgAAQBAJ&amp;pg=PA6"><i>Die Gestagene</i></a>. 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Histological, histochemical and hormonal studies". <i>Acta Obstetricia et Gynecologica Scandinavica</i>. <b>51</b> (1): <span class="nowrap">55–</span>62. <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%2F00016347209154968">10.3109/00016347209154968</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/4261828">4261828</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a>&#160;<a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:7181971">7181971</a>. <q>Thirteen patients with primary adenocarcinoma of the uterine corpus were treated for 21 days with 17alpha-hydroxy-progesterone-caproate (Primolut Depot®, Schering), 1000 mg daily, or 17alpha-hydroxy-19-nor-progesterone-caproate (Depostat®, Schering), 200 mg daily. These doses can be considered as equivalent.</q></cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Acta+Obstetricia+et+Gynecologica+Scandinavica&amp;rft.atitle=Short-term+progestogen+treatment+of+endometrial+carcinoma.+Histological%2C+histochemical+and+hormonal+studies&amp;rft.volume=51&amp;rft.issue=1&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E55-%3C%2Fspan%3E62&amp;rft.date=1972&amp;rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A7181971%23id-name%3DS2CID&amp;rft_id=info%3Apmid%2F4261828&amp;rft_id=info%3Adoi%2F10.3109%2F00016347209154968&amp;rft.aulast=Moe&amp;rft.aufirst=N&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-JürgensenTaubert1969-25"><span class="mw-cite-backlink"><b><a href="#cite_ref-JürgensenTaubert1969_25-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFJürgensenTaubert1969" class="citation journal cs1">Jürgensen O, Taubert HD (February 1969). "[Clinical observations on the effect of depot gestagen 17 alpha-hydroxy-19-nor-progesterone caproate in women with eumenorrhea]" &#91;Clinical observations on the effect of the depot gestagen 17α-hydroxy-19-nor-progesterone capronate in women with eumenorrhea&#93;. <i>Klinische Wochenschrift</i>. <b>47</b> (3): <span class="nowrap">162–</span>165. <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%2FBF01746052">10.1007/BF01746052</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/5369019">5369019</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a>&#160;<a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:41105630">41105630</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Klinische+Wochenschrift&amp;rft.atitle=%5BClinical+observations+on+the+effect+of+depot+gestagen+17+alpha-hydroxy-19-nor-progesterone+caproate+in+women+with+eumenorrhea%5D&amp;rft.volume=47&amp;rft.issue=3&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E162-%3C%2Fspan%3E165&amp;rft.date=1969-02&amp;rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A41105630%23id-name%3DS2CID&amp;rft_id=info%3Apmid%2F5369019&amp;rft_id=info%3Adoi%2F10.1007%2FBF01746052&amp;rft.aulast=J%C3%BCrgensen&amp;rft.aufirst=O&amp;rft.au=Taubert%2C+HD&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-Ferin1972a-26"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ferin1972a_26-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ferin1972a_26-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFerin1972" class="citation book cs1">Ferin J (September 1972). "Effects, Duration of Action and Metabolism in Man". In Tausk M (ed.). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=Nv5sAAAAMAAJ"><i>Pharmacology of the Endocrine System and Related Drugs: Progesterone, Progestational Drugs and Antifertility Agents</i></a>. Vol.&#160;II. Pergamon Press. pp.&#160;<span class="nowrap">13–</span>24. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<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>&#160;<a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/278011135">278011135</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=bookitem&amp;rft.atitle=Effects%2C+Duration+of+Action+and+Metabolism+in+Man&amp;rft.btitle=Pharmacology+of+the+Endocrine+System+and+Related+Drugs%3A+Progesterone%2C+Progestational+Drugs+and+Antifertility+Agents&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E13-%3C%2Fspan%3E24&amp;rft.pub=Pergamon+Press&amp;rft.date=1972-09&amp;rft_id=info%3Aoclcnum%2F278011135&amp;rft.isbn=978-0080168128&amp;rft.aulast=Ferin&amp;rft.aufirst=J&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DNv5sAAAAMAAJ&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-RaspéBrosig2013-27"><span class="mw-cite-backlink"><b><a href="#cite_ref-RaspéBrosig2013_27-0">^</a></b></span> <span class="reference-text"><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&amp;pg=PA169"><i>International Symposium on the Treatment of Carcinoma of the Prostate, Berlin, November 13 to 15, 1969: Life Science Monographs</i></a>. Elsevier. p.&#160;169. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<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&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;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&amp;rft.pages=169&amp;rft.pub=Elsevier&amp;rft.date=2013-10-22&amp;rft.isbn=978-1-4831-8711-2&amp;rft.aulast=Rasp%C3%A9&amp;rft.aufirst=G&amp;rft.au=Brosig%2C+W&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D8RjLBAAAQBAJ%26pg%3DPA169&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-MakrigiannisGaca1971-28"><span class="mw-cite-backlink"><b><a href="#cite_ref-MakrigiannisGaca1971_28-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMakrigiannisGaca1971" class="citation journal cs1">Makrigiannis D, Gaca A (1971). "Evaluation of Depostat in prostatic adenoma on the ground of clinical and sphincterotonometric studies". <i>International Urology and Nephrology</i>. <b>3</b> (1): <span class="nowrap">21–</span>29. <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%2FBF02081794">10.1007/BF02081794</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/4117491">4117491</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a>&#160;<a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:7679705">7679705</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=International+Urology+and+Nephrology&amp;rft.atitle=Evaluation+of+Depostat+in+prostatic+adenoma+on+the+ground+of+clinical+and+sphincterotonometric+studies&amp;rft.volume=3&amp;rft.issue=1&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E21-%3C%2Fspan%3E29&amp;rft.date=1971&amp;rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A7679705%23id-name%3DS2CID&amp;rft_id=info%3Apmid%2F4117491&amp;rft_id=info%3Adoi%2F10.1007%2FBF02081794&amp;rft.aulast=Makrigiannis&amp;rft.aufirst=D&amp;rft.au=Gaca%2C+A&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-pmid694436-29"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid694436_29-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid694436_29-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-pmid694436_29-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSanderNissen-MeyerAakvaag1978" class="citation journal cs1">Sander S, Nissen-Meyer R, Aakvaag A (1978). "On gestagen treatment of advanced prostatic carcinoma". <i>Scandinavian Journal of Urology and Nephrology</i>. <b>12</b> (2): <span class="nowrap">119–</span>121. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3109%2F00365597809179977">10.3109/00365597809179977</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/694436">694436</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Scandinavian+Journal+of+Urology+and+Nephrology&amp;rft.atitle=On+gestagen+treatment+of+advanced+prostatic+carcinoma&amp;rft.volume=12&amp;rft.issue=2&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E119-%3C%2Fspan%3E121&amp;rft.date=1978&amp;rft_id=info%3Adoi%2F10.3109%2F00365597809179977&amp;rft_id=info%3Apmid%2F694436&amp;rft.aulast=Sander&amp;rft.aufirst=S&amp;rft.au=Nissen-Meyer%2C+R&amp;rft.au=Aakvaag%2C+A&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-pmid519881-30"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid519881_30-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid519881_30-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKjeldPuahKaufmanLoizou1979" class="citation journal cs1">Kjeld JM, Puah CM, Kaufman B, Loizou S, Vlotides J, Gwee HM, et&#160;al. (November 1979). "Effects of norgestrel and ethinyloestradiol ingestion on serum levels of sex hormones and gonadotrophins in men". <i>Clinical Endocrinology</i>. <b>11</b> (5): <span class="nowrap">497–</span>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>&#160;<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>&#160;<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&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Clinical+Endocrinology&amp;rft.atitle=Effects+of+norgestrel+and+ethinyloestradiol+ingestion+on+serum+levels+of+sex+hormones+and+gonadotrophins+in+men&amp;rft.volume=11&amp;rft.issue=5&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E497-%3C%2Fspan%3E504&amp;rft.date=1979-11&amp;rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A5836155%23id-name%3DS2CID&amp;rft_id=info%3Apmid%2F519881&amp;rft_id=info%3Adoi%2F10.1111%2Fj.1365-2265.1979.tb03102.x&amp;rft.aulast=Kjeld&amp;rft.aufirst=JM&amp;rft.au=Puah%2C+CM&amp;rft.au=Kaufman%2C+B&amp;rft.au=Loizou%2C+S&amp;rft.au=Vlotides%2C+J&amp;rft.au=Gwee%2C+HM&amp;rft.au=Kahn%2C+F&amp;rft.au=Sood%2C+R&amp;rft.au=Joplin%2C+GF&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-WeinKavoussi2011-31"><span class="mw-cite-backlink"><b><a href="#cite_ref-WeinKavoussi2011_31-0">^</a></b></span> <span class="reference-text"><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&amp;pg=PA2938"><i>Campbell-Walsh Urology: Expert Consult Premium Edition: Enhanced Online Features and Print, 4-Volume Set</i></a>. 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"Testosterone metabolism in benign prostatic hypertrophy: in vivo studies of gestonorone caproate and cyproterone acetate". <i>British Journal of Urology</i>. <b>48</b> (6): <span class="nowrap">485–</span>491. <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.1464-410X.1976.tb06687.x">10.1111/j.1464-410X.1976.tb06687.x</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/64267">64267</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=British+Journal+of+Urology&amp;rft.atitle=Testosterone+metabolism+in+benign+prostatic+hypertrophy%3A+in+vivo+studies+of+gestonorone+caproate+and+cyproterone+acetate&amp;rft.volume=48&amp;rft.issue=6&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E485-%3C%2Fspan%3E491&amp;rft.date=1976-12&amp;rft_id=info%3Adoi%2F10.1111%2Fj.1464-410X.1976.tb06687.x&amp;rft_id=info%3Apmid%2F64267&amp;rft.aulast=Orestano&amp;rft.aufirst=F&amp;rft.au=Altwein%2C+JE&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-pmid1177428-35"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid1177428_35-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFOrestanoAltweinKnapsteinBandhauer1975" class="citation journal cs1">Orestano F, Altwein JE, Knapstein P, Bandhauer K (June 1975). "Mode of action of progesterone, gestonorone capronate (Depostat) and cyproterone acetate (Androcur) on the metabolism of testosterone in human prostatic adenoma: in vitro and in vivo investigations". <i>Journal of Steroid Biochemistry</i>. <b>6</b> (6): <span class="nowrap">845–</span>851. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0022-4731%2875%2990313-1">10.1016/0022-4731(75)90313-1</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/1177428">1177428</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Journal+of+Steroid+Biochemistry&amp;rft.atitle=Mode+of+action+of+progesterone%2C+gestonorone+capronate+%28Depostat%29+and+cyproterone+acetate+%28Androcur%29+on+the+metabolism+of+testosterone+in+human+prostatic+adenoma%3A+in+vitro+and+in+vivo+investigations&amp;rft.volume=6&amp;rft.issue=6&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E845-%3C%2Fspan%3E851&amp;rft.date=1975-06&amp;rft_id=info%3Adoi%2F10.1016%2F0022-4731%2875%2990313-1&amp;rft_id=info%3Apmid%2F1177428&amp;rft.aulast=Orestano&amp;rft.aufirst=F&amp;rft.au=Altwein%2C+JE&amp;rft.au=Knapstein%2C+P&amp;rft.au=Bandhauer%2C+K&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-KnörrBeller2013-36"><span class="mw-cite-backlink"><b><a href="#cite_ref-KnörrBeller2013_36-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKnörrBellerLauritzen2013" class="citation book cs1">Knörr K, Beller FK, Lauritzen C (17 April 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=ACybBwAAQBAJ&amp;pg=PA214"><i>Lehrbuch der Gynäkologie</i></a>. Springer-Verlag. pp.&#160;214–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-3-662-00942-0" title="Special:BookSources/978-3-662-00942-0"><bdi>978-3-662-00942-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Lehrbuch+der+Gyn%C3%A4kologie&amp;rft.pages=214-&amp;rft.pub=Springer-Verlag&amp;rft.date=2013-04-17&amp;rft.isbn=978-3-662-00942-0&amp;rft.aulast=Kn%C3%B6rr&amp;rft.aufirst=K&amp;rft.au=Beller%2C+FK&amp;rft.au=Lauritzen%2C+C&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DACybBwAAQBAJ%26pg%3DPA214&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-KnörrKnörr-Gärtner2013y-37"><span class="mw-cite-backlink"><b><a href="#cite_ref-KnörrKnörr-Gärtner2013y_37-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKnörrKnörr-GärtnerBellerLauritzen2013" class="citation book cs1">Knörr K, Knörr-Gärtner H, Beller FK, Lauritzen C (8 March 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=tpmgBgAAQBAJ&amp;pg=PA583"><i>Geburtshilfe und Gynäkologie: Physiologie und Pathologie der Reproduktion</i></a>. Springer-Verlag. pp.&#160;583–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<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&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Geburtshilfe+und+Gyn%C3%A4kologie%3A+Physiologie+und+Pathologie+der+Reproduktion&amp;rft.pages=583-&amp;rft.pub=Springer-Verlag&amp;rft.date=2013-03-08&amp;rft.isbn=978-3-642-95583-9&amp;rft.aulast=Kn%C3%B6rr&amp;rft.aufirst=K&amp;rft.au=Kn%C3%B6rr-G%C3%A4rtner%2C+H&amp;rft.au=Beller%2C+FK&amp;rft.au=Lauritzen%2C+C&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DtpmgBgAAQBAJ%26pg%3DPA583&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-Labhart2012-38"><span class="mw-cite-backlink"><b><a href="#cite_ref-Labhart2012_38-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLabhart2012" class="citation book cs1">Labhart A (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=DAgJCAAAQBAJ&amp;pg=PA554"><i>Clinical Endocrinology: Theory and Practice</i></a>. Springer Science &amp; Business Media. pp.&#160;554–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<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&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Clinical+Endocrinology%3A+Theory+and+Practice&amp;rft.pages=554-&amp;rft.pub=Springer+Science+%26+Business+Media&amp;rft.date=2012-12-06&amp;rft.isbn=978-3-642-96158-8&amp;rft.aulast=Labhart&amp;rft.aufirst=A&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DDAgJCAAAQBAJ%26pg%3DPA554&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-HorskyPresl1981-39"><span class="mw-cite-backlink"><b><a href="#cite_ref-HorskyPresl1981_39-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHorskýPresl1981" class="citation book cs1">Horský J, Presl J (1981). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=7IrpCAAAQBAJ&amp;pg=PA313">"Hormonal Treatment of Disorders of the Menstrual Cycle"</a>. In Horsky J, Presl K (eds.). <i>Ovarian Function and its Disorders: Diagnosis and Therapy</i>. Springer Science &amp; Business Media. pp.&#160;<span class="nowrap">309–</span>332. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-94-009-8195-9_11">10.1007/978-94-009-8195-9_11</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<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&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=bookitem&amp;rft.atitle=Hormonal+Treatment+of+Disorders+of+the+Menstrual+Cycle&amp;rft.btitle=Ovarian+Function+and+its+Disorders%3A+Diagnosis+and+Therapy&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E309-%3C%2Fspan%3E332&amp;rft.pub=Springer+Science+%26+Business+Media&amp;rft.date=1981&amp;rft_id=info%3Adoi%2F10.1007%2F978-94-009-8195-9_11&amp;rft.isbn=978-94-009-8195-9&amp;rft.aulast=Horsk%C3%BD&amp;rft.aufirst=J&amp;rft.au=Presl%2C+J&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D7IrpCAAAQBAJ%26pg%3DPA313&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-Ufer1969-40"><span class="mw-cite-backlink"><b><a href="#cite_ref-Ufer1969_40-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFUfer1969" class="citation book cs1">Ufer J (1969). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=G8VsAAAAMAAJ"><i>The Principles and Practice of Hormone Therapy in Gynaecology and Obstetrics</i></a>. de Gruyter. p.&#160;49. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/9783110006148" title="Special:BookSources/9783110006148"><bdi>9783110006148</bdi></a>. <q>17α-Hydroxyprogesterone caproate is a depot progestogen which is entirely free of side actions. The dose required to induce secretory changes in primed endometrium is about 250 mg. per menstrual cycle.</q></cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=The+Principles+and+Practice+of+Hormone+Therapy+in+Gynaecology+and+Obstetrics&amp;rft.pages=49&amp;rft.pub=de+Gruyter&amp;rft.date=1969&amp;rft.isbn=9783110006148&amp;rft.aulast=Ufer&amp;rft.aufirst=J&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DG8VsAAAAMAAJ&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-Pschyrembel1968r-41"><span class="mw-cite-backlink"><b><a href="#cite_ref-Pschyrembel1968r_41-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPschyrembel1968" class="citation book cs1">Pschyrembel W (1968). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=vVaTnHDFzZ0C&amp;pg=PA598"><i>Praktische Gynäkologie: für Studierende und Ärzte</i></a>. Walter de Gruyter. pp.&#160;598, 601. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<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&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Praktische+Gyn%C3%A4kologie%3A+f%C3%BCr+Studierende+und+%C3%84rzte&amp;rft.pages=598%2C+601&amp;rft.pub=Walter+de+Gruyter&amp;rft.date=1968&amp;rft.isbn=978-3-11-150424-7&amp;rft.aulast=Pschyrembel&amp;rft.aufirst=W&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DvVaTnHDFzZ0C%26pg%3DPA598&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-Ferin1972-42"><span class="mw-cite-backlink"><b><a href="#cite_ref-Ferin1972_42-0">^</a></b></span> <span class="reference-text"><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>. In Tausk M (ed.). <i>Pharmacology of the Endocrine System and Related Drugs: Progesterone, Progestational Drugs and Antifertility Agents</i>. Vol.&#160;II. 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Taylor &amp; Francis. pp.&#160;<span class="nowrap">101–</span>132. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-0-8247-8291-7" title="Special:BookSources/978-0-8247-8291-7"><bdi>978-0-8247-8291-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=bookitem&amp;rft.atitle=Pharmacology+of+Progestins%3A+17%CE%B1-Hydroxyprogesterone+Derivatives+and+Progestins+of+the+First+and+Second+Generation&amp;rft.btitle=Progestins+and+Antiprogestins+in+Clinical+Practice&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E101-%3C%2Fspan%3E132&amp;rft.pub=Taylor+%26+Francis&amp;rft.date=1999-11-10&amp;rft.isbn=978-0-8247-8291-7&amp;rft.aulast=Henzl&amp;rft.aufirst=MR&amp;rft.au=Edwards%2C+JA&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DvGJJHsJASekC&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-Brotherton1976-44"><span class="mw-cite-backlink"><b><a href="#cite_ref-Brotherton1976_44-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBrotherton1976" class="citation book cs1">Brotherton J (1976). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=zt5sAAAAMAAJ"><i>Sex Hormone Pharmacology</i></a>. Academic Press. p.&#160;114. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-0-12-137250-7" title="Special:BookSources/978-0-12-137250-7"><bdi>978-0-12-137250-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Sex+Hormone+Pharmacology&amp;rft.pages=114&amp;rft.pub=Academic+Press&amp;rft.date=1976&amp;rft.isbn=978-0-12-137250-7&amp;rft.aulast=Brotherton&amp;rft.aufirst=J&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dzt5sAAAAMAAJ&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-pmid8013220-45"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid8013220_45-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSang1994" class="citation journal cs1">Sang GW (April 1994). "Pharmacodynamic effects of once-a-month combined injectable contraceptives". <i>Contraception</i>. <b>49</b> (4): <span class="nowrap">361–</span>385. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0010-7824%2894%2990033-7">10.1016/0010-7824(94)90033-7</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/8013220">8013220</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Contraception&amp;rft.atitle=Pharmacodynamic+effects+of+once-a-month+combined+injectable+contraceptives&amp;rft.volume=49&amp;rft.issue=4&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E361-%3C%2Fspan%3E385&amp;rft.date=1994-04&amp;rft_id=info%3Adoi%2F10.1016%2F0010-7824%2894%2990033-7&amp;rft_id=info%3Apmid%2F8013220&amp;rft.aulast=Sang&amp;rft.aufirst=GW&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-pmid8013216-46"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid8013216_46-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFToppozada1994" class="citation journal cs1">Toppozada MK (April 1994). "Existing once-a-month combined injectable contraceptives". <i>Contraception</i>. <b>49</b> (4): <span class="nowrap">293–</span>301. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0010-7824%2894%2990029-9">10.1016/0010-7824(94)90029-9</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/8013216">8013216</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Contraception&amp;rft.atitle=Existing+once-a-month+combined+injectable+contraceptives&amp;rft.volume=49&amp;rft.issue=4&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E293-%3C%2Fspan%3E301&amp;rft.date=1994-04&amp;rft_id=info%3Adoi%2F10.1016%2F0010-7824%2894%2990029-9&amp;rft_id=info%3Apmid%2F8013216&amp;rft.aulast=Toppozada&amp;rft.aufirst=MK&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-Goebelsmann1986-47"><span class="mw-cite-backlink"><b><a href="#cite_ref-Goebelsmann1986_47-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFGoebelsmann1986" class="citation book cs1">Goebelsmann U (1986). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=7dnTBwAAQBAJ&amp;pg=PA67">"Pharmacokinetics of Contraceptive Steroids in Humans"</a>. In Gregoire AT, Blye RP (eds.). <i>Contraceptive Steroids: Pharmacology and Safety</i>. Springer Science &amp; Business Media. pp.&#160;<span class="nowrap">67–</span>111. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-1-4613-2241-2_4">10.1007/978-1-4613-2241-2_4</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-1-4613-2241-2" title="Special:BookSources/978-1-4613-2241-2"><bdi>978-1-4613-2241-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=bookitem&amp;rft.atitle=Pharmacokinetics+of+Contraceptive+Steroids+in+Humans&amp;rft.btitle=Contraceptive+Steroids%3A+Pharmacology+and+Safety&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E67-%3C%2Fspan%3E111&amp;rft.pub=Springer+Science+%26+Business+Media&amp;rft.date=1986&amp;rft_id=info%3Adoi%2F10.1007%2F978-1-4613-2241-2_4&amp;rft.isbn=978-1-4613-2241-2&amp;rft.aulast=Goebelsmann&amp;rft.aufirst=U&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D7dnTBwAAQBAJ%26pg%3DPA67&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-BeckerDüsterberg1980-48"><span class="mw-cite-backlink"><b><a href="#cite_ref-BeckerDüsterberg1980_48-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBeckerDüsterbergKlosterhalfen1980" class="citation journal cs1">Becker H, Düsterberg B, Klosterhalfen H (1980). "[Bioavailability of cyproterone acetate after oral and intramuscular application in men (author's transl)]" &#91;Bioavailability of Cyproterone Acetate after Oral and Intramuscular Application in Men&#93;. <i>Urologia Internationalis</i>. <b>35</b> (6): <span class="nowrap">381–</span>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>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/6452729">6452729</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Urologia+Internationalis&amp;rft.atitle=%5BBioavailability+of+cyproterone+acetate+after+oral+and+intramuscular+application+in+men+%28author%27s+transl%29%5D&amp;rft.volume=35&amp;rft.issue=6&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E381-%3C%2Fspan%3E385&amp;rft.date=1980&amp;rft_id=info%3Adoi%2F10.1159%2F000280353&amp;rft_id=info%3Apmid%2F6452729&amp;rft.aulast=Becker&amp;rft.aufirst=H&amp;rft.au=D%C3%BCsterberg%2C+B&amp;rft.au=Klosterhalfen%2C+H&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-MoltzHaase2008-49"><span class="mw-cite-backlink"><b><a href="#cite_ref-MoltzHaase2008_49-0">^</a></b></span> <span class="reference-text"><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]" &#91;Efficacy of Intra muscularly Applied Cyproterone Acetate in Hyperandrogenism&#93;. <i>Geburtshilfe und Frauenheilkunde</i>. <b>43</b> (5): <span class="nowrap">281–</span>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>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/6223851">6223851</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Geburtshilfe+und+Frauenheilkunde&amp;rft.atitle=%5BTreatment+of+virilized+women+with+intramuscular+administration+of+cyproterone+acetate%5D&amp;rft.volume=43&amp;rft.issue=5&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E281-%3C%2Fspan%3E287&amp;rft.date=1983-05&amp;rft_id=info%3Adoi%2F10.1055%2Fs-2008-1036893&amp;rft_id=info%3Apmid%2F6223851&amp;rft.aulast=Moltz&amp;rft.aufirst=L&amp;rft.au=Haase%2C+F&amp;rft.au=Schwartz%2C+U&amp;rft.au=Hammerstein%2C+J&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-WrightBurgess2012-50"><span class="mw-cite-backlink"><b><a href="#cite_ref-WrightBurgess2012_50-0">^</a></b></span> <span class="reference-text"><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&amp;pg=PA114"><i>Long Acting Injections and Implants</i></a>. Springer Science &amp; Business Media. pp.&#160;114–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<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&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Long+Acting+Injections+and+Implants&amp;rft.pages=114-&amp;rft.pub=Springer+Science+%26+Business+Media&amp;rft.date=2012-01-29&amp;rft.isbn=978-1-4614-0554-2&amp;rft.aulast=Wright&amp;rft.aufirst=JC&amp;rft.au=Burgess%2C+DJ&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D36nkGjEGEToC%26pg%3DPA114&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-ChuLi1986-51"><span class="mw-cite-backlink"><b><a href="#cite_ref-ChuLi1986_51-0">^</a></b></span> <span class="reference-text"><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>. <i>The Chinese Journal of Clinical Pharmacology</i>. <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&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=The+Chinese+Journal+of+Clinical+Pharmacology&amp;rft.atitle=Pharmacokinetics+of+megestrol+acetate+in+women+receiving+IM+injection+of+estradiol-megestrol+long-acting+injectable+contraceptive&amp;rft.date=1986-04&amp;rft.aulast=Chu&amp;rft.aufirst=YH&amp;rft.au=Li%2C+Q&amp;rft.au=Zhao%2C+ZF&amp;rft_id=http%3A%2F%2Fen.cnki.com.cn%2FArticle_en%2FCJFDTOTAL-GLYZ198604003.htm&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-RunnebaumRabe2012-52"><span class="mw-cite-backlink"><b><a href="#cite_ref-RunnebaumRabe2012_52-0">^</a></b></span> <span class="reference-text"><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&amp;pg=PA429"><i>Female Contraception: Update and Trends</i></a>. Springer Science &amp; Business Media. pp.&#160;429–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<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&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Female+Contraception%3A+Update+and+Trends&amp;rft.pages=429-&amp;rft.pub=Springer+Science+%26+Business+Media&amp;rft.date=2012-12-06&amp;rft.isbn=978-3-642-73790-9&amp;rft.aulast=Runnebaum&amp;rft.aufirst=BC&amp;rft.au=Rabe%2C+T&amp;rft.au=Kiesel%2C+L&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DLtT6CAAAQBAJ%26pg%3DPA429&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-ArtiniGenazzani2001-53"><span class="mw-cite-backlink"><b><a href="#cite_ref-ArtiniGenazzani2001_53-0">^</a></b></span> <span class="reference-text"><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&amp;pg=PA105"><i>Advances in Gynecological Endocrinology</i></a>. CRC Press. pp.&#160;105–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<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&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Advances+in+Gynecological+Endocrinology&amp;rft.pages=105-&amp;rft.pub=CRC+Press&amp;rft.date=2001-12-11&amp;rft.isbn=978-1-84214-071-0&amp;rft.aulast=Artini&amp;rft.aufirst=PG&amp;rft.au=Genazzani%2C+AR&amp;rft.au=Petraglia%2C+F&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DdknDdAonzlUC%26pg%3DPA105&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-KingBrucker2013-54"><span class="mw-cite-backlink"><b><a href="#cite_ref-KingBrucker2013_54-0">^</a></b></span> <span class="reference-text"><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&amp;pg=PA495"><i>Varney's Midwifery</i></a>. Jones &amp; Bartlett Publishers. pp.&#160;495–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<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&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Varney%27s+Midwifery&amp;rft.pages=495-&amp;rft.pub=Jones+%26+Bartlett+Publishers&amp;rft.date=2013-10-21&amp;rft.isbn=978-1-284-02542-2&amp;rft.aulast=King&amp;rft.aufirst=TL&amp;rft.au=Brucker%2C+MC&amp;rft.au=Kriebs%2C+JM&amp;rft.au=Fahey%2C+JO&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DdbaNAQAAQBAJ%26pg%3DPA495&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-Denis2012-64"><span class="mw-cite-backlink"><b><a href="#cite_ref-Denis2012_64-0">^</a></b></span> <span class="reference-text"><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&amp;pg=PT112"><i>The Medical Management of Prostate Cancer</i></a>. Springer Science &amp; Business Media. pp.&#160;112–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<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&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=The+Medical+Management+of+Prostate+Cancer&amp;rft.pages=112-&amp;rft.pub=Springer+Science+%26+Business+Media&amp;rft.date=2012-12-06&amp;rft.isbn=978-3-642-73238-6&amp;rft.aulast=Denis&amp;rft.aufirst=L&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DT78hBQAAQBAJ%26pg%3DPT112&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-RunnebaumRabe2012a-65"><span class="mw-cite-backlink"><b><a href="#cite_ref-RunnebaumRabe2012a_65-0">^</a></b></span> <span class="reference-text"><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&amp;pg=PA133"><i>Future Aspects in Contraception: Proceeding of an International Symposium held in Heidelberg, 5–8 September 1984 Part 1 Male Contraception</i></a>. Springer Science &amp; Business Media. pp.&#160;133–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<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&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;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&amp;rft.pages=133-&amp;rft.pub=Springer+Science+%26+Business+Media&amp;rft.date=2012-12-06&amp;rft.isbn=978-94-009-4910-2&amp;rft.aulast=Runnebaum&amp;rft.aufirst=BC&amp;rft.au=Rabe%2C+T&amp;rft.au=Kiesel%2C+L&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DGX2oBgAAQBAJ%26pg%3DPA133&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-PalancaJuco2008-66"><span class="mw-cite-backlink"><b><a href="#cite_ref-PalancaJuco2008_66-0">^</a></b></span> <span class="reference-text"><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". <i>Current Medical Research and Opinion</i>. <b>4</b> (7): <span class="nowrap">513–</span>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>&#160;<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>&#160;<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&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Current+Medical+Research+and+Opinion&amp;rft.atitle=Conservative+treatment+of+benign+prostatic+hyperplasia&amp;rft.volume=4&amp;rft.issue=7&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E513-%3C%2Fspan%3E520&amp;rft.date=2008&amp;rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A31798723%23id-name%3DS2CID&amp;rft_id=info%3Apmid%2F66118&amp;rft_id=info%3Adoi%2F10.1185%2F03007997709109342&amp;rft.aulast=Palanca&amp;rft.aufirst=E&amp;rft.au=Juco%2C+W&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-Nevinny-Stickel1962-67"><span class="mw-cite-backlink"><b><a href="#cite_ref-Nevinny-Stickel1962_67-0">^</a></b></span> <span class="reference-text"><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". <i>Gewebs- und Neurohormone</i> &#91;<i>The progestational effects of hydroxy-nor-progesterone esters in women</i>&#93;. Symposion der Deutschen Gesellschaft für Endokrinologie. Springer. pp.&#160;<span class="nowrap">248–</span>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>&#160;<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&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=bookitem&amp;rft.atitle=Die+gestagene+Wirkung+von+Hydroxy-nor-Progesteronestern+bei+der+Frau&amp;rft.btitle=Gewebs-+und+Neurohormone&amp;rft.series=Symposion+der+Deutschen+Gesellschaft+f%C3%BCr+Endokrinologie&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E248-%3C%2Fspan%3E255&amp;rft.pub=Springer&amp;rft.date=1962&amp;rft_id=info%3Adoi%2F10.1007%2F978-3-642-86860-3_27&amp;rft.isbn=978-3-540-02909-0&amp;rft.aulast=Nevinny-Stickel&amp;rft.aufirst=J&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-HorskyPresl1981b-68"><span class="mw-cite-backlink"><b><a href="#cite_ref-HorskyPresl1981b_68-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHorskýPresl1981" class="citation book cs1">Horský J, Presl J (1981). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=7IrpCAAAQBAJ&amp;pg=PA313">"Hormonal Treatment of Disorders of the Menstrual Cycle"</a>. In Horsky J, Presl J (eds.). <i>Ovarian Function and its Disorders: Diagnosis and Therapy</i>. Developments in Obstetrics and Gynecology. Springer Science &amp; Business Media. pp.&#160;<span class="nowrap">309–</span>332. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-94-009-8195-9_11">10.1007/978-94-009-8195-9_11</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<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&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=bookitem&amp;rft.atitle=Hormonal+Treatment+of+Disorders+of+the+Menstrual+Cycle&amp;rft.btitle=Ovarian+Function+and+its+Disorders%3A+Diagnosis+and+Therapy&amp;rft.series=Developments+in+Obstetrics+and+Gynecology&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E309-%3C%2Fspan%3E332&amp;rft.pub=Springer+Science+%26+Business+Media&amp;rft.date=1981&amp;rft_id=info%3Adoi%2F10.1007%2F978-94-009-8195-9_11&amp;rft.isbn=978-94-009-8195-9&amp;rft.aulast=Horsk%C3%BD&amp;rft.aufirst=J&amp;rft.au=Presl%2C+J&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D7IrpCAAAQBAJ%26pg%3DPA313&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-pmid340117-69"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid340117_69-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid340117_69-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="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". <i>Clinical Science and Molecular Medicine</i>. <b>54</b> (2): <span class="nowrap">193–</span>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>&#160;<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>&#160;<a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:1799407">1799407</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Clinical+Science+and+Molecular+Medicine&amp;rft.atitle=Comparative+effects+of+oestrogen+and+a+progestogen+on+bone+loss+in+postmenopausal+women&amp;rft.volume=54&amp;rft.issue=2&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E193-%3C%2Fspan%3E195&amp;rft.date=1978-02&amp;rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A1799407%23id-name%3DS2CID&amp;rft_id=info%3Apmid%2F340117&amp;rft_id=info%3Adoi%2F10.1042%2Fcs0540193&amp;rft.aulast=Lindsay&amp;rft.aufirst=R&amp;rft.au=Hart%2C+DM&amp;rft.au=Purdie%2C+D&amp;rft.au=Ferguson%2C+MM&amp;rft.au=Clark%2C+AS&amp;rft.au=Kraszewski%2C+A&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-pmid865726-70"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid865726_70-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid865726_70-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-pmid865726_70-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFToppozada1977" class="citation journal cs1">Toppozada M (June 1977). "The clinical use of monthly injectable contraceptive preparations". <i>Obstetrical &amp; Gynecological Survey</i>. <b>32</b> (6): <span class="nowrap">335–</span>347. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1097%2F00006254-197706000-00001">10.1097/00006254-197706000-00001</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/865726">865726</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Obstetrical+%26+Gynecological+Survey&amp;rft.atitle=The+clinical+use+of+monthly+injectable+contraceptive+preparations&amp;rft.volume=32&amp;rft.issue=6&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E335-%3C%2Fspan%3E347&amp;rft.date=1977-06&amp;rft_id=info%3Adoi%2F10.1097%2F00006254-197706000-00001&amp;rft_id=info%3Apmid%2F865726&amp;rft.aulast=Toppozada&amp;rft.aufirst=M&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-NagelKolb1973-71"><span class="mw-cite-backlink"><b><a href="#cite_ref-NagelKolb1973_71-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFNagelKolbKroemerMaksimović1973" class="citation book cs1">Nagel R, Kolb K, Kroemer C, Maksimović P, Laudahn G (1973). "Verteilungsstudien und pharmakokinetische Parameter nach i.m. Gabe von Gestonoron-capronat (Depostat) und Cyproteron-acetat (Androcur) beim Menschen". <i>24. Tagung vom 13. Bis 16. September 1972 in Hannover</i> &#91;<i>Distribution studies and pharmacokinetic parameters after i.m. administration of gestonoron-capronate (Depostat) and cyproterone-acetate (Androcur) in man</i>&#93;. Verhandlungsbericht der Deutschen Gesellschaft für Urologie. Vol.&#160;24. pp.&#160;<span class="nowrap">133–</span>138. <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%2F978-3-642-80738-1_36">10.1007/978-3-642-80738-1_36</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-3-540-06186-1" title="Special:BookSources/978-3-540-06186-1"><bdi>978-3-540-06186-1</bdi></a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a>&#160;<a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0070-413X">0070-413X</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=bookitem&amp;rft.atitle=Verteilungsstudien+und+pharmakokinetische+Parameter+nach+i.m.+Gabe+von+Gestonoron-capronat+%28Depostat%29+und+Cyproteron-acetat+%28Androcur%29+beim+Menschen&amp;rft.btitle=24.+Tagung+vom+13.+Bis+16.+September+1972+in+Hannover&amp;rft.series=Verhandlungsbericht+der+Deutschen+Gesellschaft+f%C3%BCr+Urologie&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E133-%3C%2Fspan%3E138&amp;rft.date=1973&amp;rft.issn=0070-413X&amp;rft_id=info%3Adoi%2F10.1007%2F978-3-642-80738-1_36&amp;rft.isbn=978-3-540-06186-1&amp;rft.aulast=Nagel&amp;rft.aufirst=R&amp;rft.au=Kolb%2C+K&amp;rft.au=Kroemer%2C+C&amp;rft.au=Maksimovi%C4%87%2C+P&amp;rft.au=Laudahn%2C+G&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-Elks2014-72"><span class="mw-cite-backlink">^ <a href="#cite_ref-Elks2014_72-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Elks2014_72-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Elks2014_72-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Elks2014_72-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Elks2014_72-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-Elks2014_72-5"><sup><i><b>f</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFElks2014" class="citation book cs1">Elks J (14 November 2014). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=0vXTBwAAQBAJ&amp;pg=PA595"><i>The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies</i></a>. Springer. pp.&#160;595–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-1-4757-2085-3" title="Special:BookSources/978-1-4757-2085-3"><bdi>978-1-4757-2085-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=The+Dictionary+of+Drugs%3A+Chemical+Data%3A+Chemical+Data%2C+Structures+and+Bibliographies&amp;rft.pages=595-&amp;rft.pub=Springer&amp;rft.date=2014-11-14&amp;rft.isbn=978-1-4757-2085-3&amp;rft.aulast=Elks&amp;rft.aufirst=J&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D0vXTBwAAQBAJ%26pg%3DPA595&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-KleemannEngel2001-73"><span class="mw-cite-backlink"><b><a href="#cite_ref-KleemannEngel2001_73-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKleemannEngel2001" class="citation book cs1">Kleemann A, Engel J (2001). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=y25qAAAAMAAJ"><i>Pharmaceutical substances: syntheses, patents, applications</i></a>. Thieme. p.&#160;962. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-3-13-558404-1" title="Special:BookSources/978-3-13-558404-1"><bdi>978-3-13-558404-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Pharmaceutical+substances%3A+syntheses%2C+patents%2C+applications&amp;rft.pages=962&amp;rft.pub=Thieme&amp;rft.date=2001&amp;rft.isbn=978-3-13-558404-1&amp;rft.aulast=Kleemann&amp;rft.aufirst=A&amp;rft.au=Engel%2C+J&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dy25qAAAAMAAJ&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-MHRA-74"><span class="mw-cite-backlink"><b><a href="#cite_ref-MHRA_74-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.mhra.gov.uk/spc-pil/">"Find product information about medicines"</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=unknown&amp;rft.btitle=Find+product+information+about+medicines&amp;rft_id=http%3A%2F%2Fwww.mhra.gov.uk%2Fspc-pil%2F&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-Smith2013-75"><span class="mw-cite-backlink"><b><a href="#cite_ref-Smith2013_75-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSmith2013" class="citation book cs1">Smith PH (29 June 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=gtAFCAAAQBAJ&amp;pg=PA309"><i>Cancer of the Prostate and Kidney</i></a>. 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Retrieved <span class="nowrap">2018-09-19</span></span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Revista+Peruana+de+Ginecolog%C3%ADa+y+Obstetricia&amp;rft.atitle=Empleo+del+capronato+de+17-hidroxi-19-norprogesterona+como+anticonceptivo+inyectable+de+dep%C3%B3sito&amp;rft.volume=14&amp;rft.issue=2&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E223-%3C%2Fspan%3E233&amp;rft.date=2015&amp;rft_id=info%3Adoi%2F10.31403%2Frpgo.v14i1457&amp;rft.aulast=Hurtado&amp;rft.aufirst=H&amp;rft.au=Kesseru%2C+E&amp;rft.au=Larra%C3%B1aga%2C+A&amp;rft_id=http%3A%2F%2Fspog.org.pe%2Fweb%2Frevista%2Findex.php%2FRPGO%2Farticle%2Fview%2F1457&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-pmid4732140-86"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid4732140_86-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFNazerValenzuela1973" class="citation journal cs1 cs1-prop-foreign-lang-source">Nazer J, Valenzuela CY (March 1973). <a rel="nofollow" class="external text" href="https://www.popline.org/node/490180">"&#91;Possible biological effects of contraceptives&#93;"</a>. <i>Revista Médica de Chile</i> (in Spanish). <b>101</b> (3): <span class="nowrap">234–</span>236. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/4732140">4732140</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Revista+M%C3%A9dica+de+Chile&amp;rft.atitle=%5BPossible+biological+effects+of+contraceptives%5D&amp;rft.volume=101&amp;rft.issue=3&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E234-%3C%2Fspan%3E236&amp;rft.date=1973-03&amp;rft_id=info%3Apmid%2F4732140&amp;rft.aulast=Nazer&amp;rft.aufirst=J&amp;rft.au=Valenzuela%2C+CY&amp;rft_id=https%3A%2F%2Fwww.popline.org%2Fnode%2F490180&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-Restrepo1969-87"><span class="mw-cite-backlink"><b><a href="#cite_ref-Restrepo1969_87-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRodriguez-Restrepo1969" class="citation journal cs1">Rodriguez-Restrepo R (1969). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20180919061829/https://www.popline.org/node/479231">"17-alpha-hydroxy 19 norprogesterone capronate as a prolonged-action injectable contraceptive agent"</a>. <i>Revista Colombiana de Obstetricia y Ginecologia</i>. <b>20</b>: <span class="nowrap">247–</span>255. 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"The treatment of advanced cystadenocarcinoma of the ovary with gestronol and continuous oral cyclophosphamide". <i>British Journal of Obstetrics and Gynaecology</i>. <b>86</b> (7): <span class="nowrap">497–</span>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>&#160;<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>&#160;<a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:31408925">31408925</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=British+Journal+of+Obstetrics+and+Gynaecology&amp;rft.atitle=The+treatment+of+advanced+cystadenocarcinoma+of+the+ovary+with+gestronol+and+continuous+oral+cyclophosphamide&amp;rft.volume=86&amp;rft.issue=7&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E497-%3C%2Fspan%3E500&amp;rft.date=1979-07&amp;rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A31408925%23id-name%3DS2CID&amp;rft_id=info%3Apmid%2F476014&amp;rft_id=info%3Adoi%2F10.1111%2Fj.1471-0528.1979.tb10799.x&amp;rft.aulast=Guthrie&amp;rft.aufirst=D&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> <li id="cite_note-pmid687544-89"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid687544_89-0">^</a></b></span> <span class="reference-text"><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". <i>British Journal of Obstetrics and Gynaecology</i>. <b>85</b> (8): <span class="nowrap">627–</span>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>&#160;<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>&#160;<a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:30816473">30816473</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=British+Journal+of+Obstetrics+and+Gynaecology&amp;rft.atitle=The+effect+of+sex+steroids+on+the+in+vitro+synthesis+of+DNA+by+malignant+ovarian+tumours&amp;rft.volume=85&amp;rft.issue=8&amp;rft.pages=%3Cspan+class%3D%22nowrap%22%3E627-%3C%2Fspan%3E633&amp;rft.date=1978-08&amp;rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A30816473%23id-name%3DS2CID&amp;rft_id=info%3Apmid%2F687544&amp;rft_id=info%3Adoi%2F10.1111%2Fj.1471-0528.1978.tb14933.x&amp;rft.aulast=Darwish&amp;rft.aufirst=DH&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGestonorone+caproate" class="Z3988"></span></span> </li> </ol></div></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><style data-mw-deduplicate="TemplateStyles:r1236075235">.mw-parser-output .navbox{box-sizing:border-box;border:1px solid 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.navbox{display:none!important}}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /></div><div role="navigation" class="navbox" aria-labelledby="Progestogens_and_antiprogestogens153" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Progestogens_and_antiprogestogens" title="Template:Progestogens and antiprogestogens"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Progestogens_and_antiprogestogens" title="Template talk:Progestogens and antiprogestogens"><abbr title="Discuss 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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</span> <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><i>Progesterone derivatives:</i> <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">Progesterone</a></li> <li><a href="/wiki/Quingestrone" title="Quingestrone">Quingestrone</a></li></ul> <ul><li><i>Retroprogesterone derivatives:</i> <a href="/wiki/Dydrogesterone" title="Dydrogesterone">Dydrogesterone</a></li> <li><a href="/wiki/Trengestone" title="Trengestone">Trengestone</a></li></ul> <ul><li><i>17α-Hydroxyprogesterone (and closely related) derivatives:</i> <i>17α-Hydroxylated:</i> <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><sup>#</sup></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>; <i>17α-Methylated:</i> <a href="/wiki/Medrogestone" title="Medrogestone">Medrogestone</a>; <i>Others:</i> <a href="/wiki/Haloprogesterone" title="Haloprogesterone">Haloprogesterone</a></li></ul> <ul><li><i>19-Norprogesterone derivatives:</i> <i>17α-Hydroxylated:</i> <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>; <i>17α-Methylated:</i> <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><i>Testosterone derivatives:</i> <i>Estranes:</i> <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><i>19-Nortestosterone derivatives:</i> <i>Estranes:</i> <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><sup>#</sup></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>; <i>Gonanes:</i> <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><sup>#</sup></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><i>Spirolactone derivatives:</i> <a href="/wiki/Drospirenone" title="Drospirenone">Drospirenone</a></li></ul> <ul><li><i>Others:</i> <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</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Telapristone" title="Telapristone">Telapristone</a><sup>§</sup></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</span> <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><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div> <dl><dt>See also</dt> <dd><a href="/wiki/Template: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><i><a href="/wiki/Pygeum_(herbal_remedy)" class="mw-redirect" title="Pygeum (herbal remedy)">Pygeum africanum</a></i></li> <li><i><a href="/wiki/Saw_palmetto_extract" title="Saw palmetto extract">Saw palmetto extract</a></i></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</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Progesterone derivatives:</i> <a href="/wiki/3%CE%B2-Dihydroprogesterone" title="3β-Dihydroprogesterone">3β-Dihydroprogesterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">5α-Dihydroprogesterone</a></li> <li><a href="/wiki/6%CE%B1-Methylprogesterone" title="6α-Methylprogesterone">6α-Methylprogesterone</a></li> <li><a href="/wiki/9%CE%B1-Bromo-11-ketoprogesterone" class="mw-redirect" title="9α-Bromo-11-ketoprogesterone">9α-Bromo-11-ketoprogesterone</a></li> <li><a href="/wiki/11-Dehydroprogesterone" title="11-Dehydroprogesterone">11-Dehydroprogesterone</a></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyprogesterone" title="16α-Hydroxyprogesterone">16α-Hydroxyprogesterone</a></li> <li><a href="/w/index.php?title=17%CE%B1-Methyl-11-deoxycorticosterone_acetate&amp;action=edit&amp;redlink=1" class="new" title="17α-Methyl-11-deoxycorticosterone acetate (page does not exist)">17α-Methyl-11-deoxycorticosterone acetate</a></li> <li><a href="/wiki/20%CE%B1-Dihydroprogesterone" title="20α-Dihydroprogesterone">20α-Dihydroprogesterone</a></li> <li><a href="/wiki/20%CE%B2-Dihydroprogesterone" title="20β-Dihydroprogesterone">20β-Dihydroprogesterone</a></li> <li><a href="/wiki/Dimepregnen" title="Dimepregnen">Dimepregnen</a></li> <li><a href="/wiki/Diosgenin" title="Diosgenin">Diosgenin</a></li> <li><a href="/wiki/P1-185" title="P1-185">P1-185</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Progesterone_3-acetyl_enol_ether" title="Progesterone 3-acetyl enol ether">Progesterone 3-acetyl enol ether</a></li> <li><a href="/wiki/Quingestrone" title="Quingestrone">Quingestrone</a></li></ul> <ul><li><i>Retroprogesterone derivatives:</i> <a href="/wiki/20%CE%B1-Dihydrodydrogesterone" title="20α-Dihydrodydrogesterone">20α-Dihydrodydrogesterone</a></li> <li><a href="/wiki/20%CE%B1-Dihydrotrengestone" title="20α-Dihydrotrengestone">20α-Dihydrotrengestone</a></li> <li><a href="/wiki/DU-41164" title="DU-41164">DU-41164</a></li> <li><a href="/wiki/DU-41165" title="DU-41165">DU-41165</a></li> <li><a href="/wiki/Dydrogesterone" title="Dydrogesterone">Dydrogesterone</a></li> <li><a href="/wiki/Retroprogesterone" title="Retroprogesterone">Retroprogesterone</a></li> <li><a href="/wiki/Ro_6-3129" title="Ro 6-3129">Ro 6-3129</a></li> <li><a href="/wiki/Trengestone" title="Trengestone">Trengestone</a></li></ul> <ul><li><i>17α-Substituted progesterone derivatives:</i> <a href="/wiki/6%CE%B1-Methyl-17%CE%B1-bromoprogesterone" title="6α-Methyl-17α-bromoprogesterone">6α-Methyl-17α-bromoprogesterone</a></li> <li><a href="/wiki/15%CE%B2-Hydroxycyproterone_acetate" title="15β-Hydroxycyproterone acetate">15β-Hydroxycyproterone acetate</a></li> <li><a href="/wiki/16-Methylene-17%CE%B1-hydroxyprogesterone_acetate" title="16-Methylene-17α-hydroxyprogesterone acetate">16-Methylene-17α-hydroxyprogesterone acetate</a></li> <li><a href="/wiki/17%CE%B1-Bromoprogesterone" title="17α-Bromoprogesterone">17α-Bromoprogesterone</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone (hydroxyprogesterone)</a></li> <li><a href="/wiki/17%CE%B1-Methylprogesterone" title="17α-Methylprogesterone">17α-Methylprogesterone</a></li> <li><a href="/wiki/Acetomepregenol" title="Acetomepregenol">Acetomepregenol (mepregenol diacetate)</a></li> <li><a href="/wiki/Algestone" title="Algestone">Algestone</a></li> <li><a href="/wiki/Algestone_acetonide" title="Algestone acetonide">Algestone acetonide</a></li> <li><a href="/wiki/Algestone_acetophenide" title="Algestone acetophenide">Algestone acetophenide</a></li> <li><a href="/wiki/Anagestone" title="Anagestone">Anagestone</a></li> <li><a href="/wiki/Anagestone_acetate" title="Anagestone acetate">Anagestone acetate</a></li> <li><a href="/w/index.php?title=Bromethenmadinone&amp;action=edit&amp;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&amp;action=edit&amp;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&amp;action=edit&amp;redlink=1" class="new" title="Gestobutanoyl (page does not exist)">Gestobutanoyl</a></li> <li><a href="/wiki/Haloprogesterone" title="Haloprogesterone">Haloprogesterone</a></li> <li><a href="/wiki/Hydromadinone" title="Hydromadinone">Hydromadinone</a></li> <li><a href="/wiki/Hydromadinone_acetate" title="Hydromadinone acetate">Hydromadinone acetate</a></li> <li><a href="/wiki/Hydroxyprogesterone_acetate" title="Hydroxyprogesterone acetate">Hydroxyprogesterone acetate</a></li> <li><a href="/wiki/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">Hydroxyprogesterone caproate (hydroxyprogesterone hexanoate)</a></li> <li><a href="/wiki/Hydroxyprogesterone_heptanoate" title="Hydroxyprogesterone heptanoate">Hydroxyprogesterone heptanoate (hydroxyprogesterone enanthate)</a></li> <li><a href="/wiki/Hydroxyprogesterone_heptanoate_benzilic_acid_hydrazone" title="Hydroxyprogesterone heptanoate benzilic acid hydrazone">Hydroxyprogesterone heptanoate benzilic acid hydrazone</a></li> <li><a href="/wiki/Mecigestone" title="Mecigestone">Mecigestone (pentarane B)</a></li> <li><a href="/wiki/Medrogestone" title="Medrogestone">Medrogestone</a></li> <li><a href="/wiki/Medroxyprogesterone" title="Medroxyprogesterone">Medroxyprogesterone</a></li> <li><a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">Medroxyprogesterone acetate</a></li> <li><a href="/wiki/Medroxyprogesterone_caproate" title="Medroxyprogesterone caproate">Medroxyprogesterone caproate</a></li> <li><a href="/wiki/Megestrol" title="Megestrol">Megestrol</a></li> <li><a href="/wiki/Megestrol_acetate" title="Megestrol acetate">Megestrol acetate</a></li> <li><a href="/wiki/Megestrol_caproate" title="Megestrol caproate">Megestrol caproate</a></li> <li><a href="/wiki/Melengestrol" title="Melengestrol">Melengestrol</a></li> <li><a href="/wiki/Melengestrol_acetate" title="Melengestrol acetate">Melengestrol acetate</a></li> <li><a href="/wiki/Methenmadinone" title="Methenmadinone">Methenmadinone</a></li> <li><a href="/wiki/Methenmadinone_acetate" title="Methenmadinone acetate">Methenmadinone acetate</a></li> <li><a href="/wiki/Methenmadinone_caproate" title="Methenmadinone caproate">Methenmadinone caproate</a></li> <li><a href="/wiki/Mometasone" title="Mometasone">Mometasone</a></li> <li><a href="/wiki/Mometasone_furoate" class="mw-redirect" title="Mometasone furoate">Mometasone furoate</a></li> <li><a href="/wiki/Osaterone" title="Osaterone">Osaterone</a></li> <li><a href="/wiki/Osaterone_acetate" title="Osaterone acetate">Osaterone acetate</a></li> <li><a href="/wiki/Pentagestrone" title="Pentagestrone">Pentagestrone</a></li> <li><a href="/wiki/Pentagestrone_acetate" title="Pentagestrone acetate">Pentagestrone acetate</a></li> <li><a href="/wiki/Pentarane_A" title="Pentarane A">Pentarane A</a></li> <li><a href="/wiki/Proligestone" title="Proligestone">Proligestone</a></li> <li><a href="/wiki/Triamcinolone_acetonide" title="Triamcinolone acetonide">Triamcinolone acetonide</a></li></ul> <ul><li><i>19-Norprogesterone derivatives:</i> <a href="/wiki/17%CE%B1-Methyl-19-norprogesterone" title="17α-Methyl-19-norprogesterone">17α-Methyl-19-norprogesterone</a></li> <li><a href="/wiki/18-Methylsegesterone_acetate" title="18-Methylsegesterone acetate">18-Methylsegesterone acetate</a></li> <li><a href="/wiki/19-Norprogesterone" title="19-Norprogesterone">19-Norprogesterone</a></li> <li><a href="/wiki/Amadinone" title="Amadinone">Amadinone</a></li> <li><a href="/wiki/Amadinone_acetate" title="Amadinone acetate">Amadinone acetate</a></li> <li><a href="/wiki/Demegestone" title="Demegestone">Demegestone</a></li> <li><a href="/w/index.php?title=Fluoro_ethyl_norprogesterone&amp;action=edit&amp;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&amp;action=edit&amp;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><i>Testosterone derivatives:</i> Progestins: <a href="/wiki/6,6-Difluoronorethisterone" title="6,6-Difluoronorethisterone">6,6-Difluoronorethisterone</a></li> <li><a href="/wiki/6,6-Difluoronorethisterone_acetate" title="6,6-Difluoronorethisterone acetate">6,6-Difluoronorethisterone acetate</a></li> <li><a href="/wiki/17%CE%B1-Allyl-19-nortestosterone" title="17α-Allyl-19-nortestosterone">17α-Allyl-19-nortestosterone</a></li> <li><a href="/wiki/Allylestrenol" title="Allylestrenol">Allylestrenol</a></li> <li><a href="/wiki/Altrenogest" title="Altrenogest">Altrenogest</a></li> <li><a href="/wiki/Chloroethynylnorgestrel" title="Chloroethynylnorgestrel">Chloroethynylnorgestrel</a></li> <li><a href="/wiki/Cingestol" title="Cingestol">Cingestol</a></li> <li><a href="/wiki/Danazol" title="Danazol">Danazol</a></li> <li><a href="/wiki/Desogestrel" title="Desogestrel">Desogestrel</a></li> <li><a href="/wiki/Dienogest" title="Dienogest">Dienogest</a></li> <li><a href="/wiki/Ethinylandrostenediol" title="Ethinylandrostenediol">Ethinylandrostenediol</a> <ul><li><a href="/wiki/Ethandrostate" title="Ethandrostate">Ethandrostate</a></li></ul></li> <li><a href="/wiki/Ethisterone" title="Ethisterone">Ethisterone</a></li> <li><a href="/wiki/Ethynerone" title="Ethynerone">Ethynerone</a></li> <li><a href="/wiki/Etonogestrel" title="Etonogestrel">Etonogestrel</a></li> <li><a href="/wiki/Etynodiol" title="Etynodiol">Etynodiol</a></li> <li><a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">Etynodiol diacetate</a></li> <li><a href="/wiki/Gestodene" title="Gestodene">Gestodene</a></li> <li><a href="/wiki/Gestrinone" title="Gestrinone">Gestrinone</a></li> <li><a href="/wiki/Levonorgestrel" title="Levonorgestrel">Levonorgestrel</a></li> <li><a href="/wiki/Levonorgestrel_ester" class="mw-redirect" title="Levonorgestrel ester">Levonorgestrel esters</a> (e.g., <a href="/wiki/Levonorgestrel_butanoate" title="Levonorgestrel butanoate">levonorgestrel butanoate</a>)</li> <li><a href="/wiki/Lynestrenol" title="Lynestrenol">Lynestrenol</a></li> <li><a href="/wiki/Lynestrenol_phenylpropionate" title="Lynestrenol phenylpropionate">Lynestrenol phenylpropionate</a></li> <li><a href="/wiki/Metynodiol" title="Metynodiol">Metynodiol</a></li> <li><a href="/wiki/Metynodiol_diacetate" title="Metynodiol diacetate">Metynodiol diacetate</a></li> <li><a href="/wiki/Norelgestromin" title="Norelgestromin">Norelgestromin</a></li> <li><a href="/wiki/Norethisterone" title="Norethisterone">Norethisterone (norethindrone)</a></li> <li><a href="/wiki/Norethisterone_ester" class="mw-redirect" title="Norethisterone ester">Norethisterone esters</a> (e.g., <a href="/wiki/Norethisterone_acetate" title="Norethisterone acetate">norethisterone acetate</a>, <a href="/wiki/Norethisterone_enanthate" title="Norethisterone enanthate">norethisterone enanthate</a>)</li> <li><a href="/wiki/Noretynodrel" title="Noretynodrel">Noretynodrel</a></li> <li><a href="/wiki/Norgesterone" title="Norgesterone">Norgesterone</a></li> <li><a href="/wiki/Norgestimate" title="Norgestimate">Norgestimate</a></li> <li><a href="/wiki/Norgestrel" title="Norgestrel">Norgestrel</a></li> <li><a href="/wiki/Norgestrienone" title="Norgestrienone">Norgestrienone</a></li> <li><a href="/wiki/Norvinisterone" title="Norvinisterone">Norvinisterone</a></li> <li><a href="/wiki/Oxendolone" title="Oxendolone">Oxendolone</a></li> <li><a href="/wiki/Quingestanol" title="Quingestanol">Quingestanol</a></li> <li><a href="/wiki/Quingestanol_acetate" title="Quingestanol acetate">Quingestanol acetate</a></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li> <li><a href="/wiki/Tigestol" title="Tigestol">Tigestol</a></li> <li><a href="/wiki/Tosagestin" title="Tosagestin">Tosagestin</a>; Anabolic–androgenic steroids: <a href="/wiki/11%CE%B2-Methyl-19-nortestosterone" title="11β-Methyl-19-nortestosterone">11β-Methyl-19-nortestosterone</a></li> <li><a href="/wiki/11%CE%B2-Methyl-19-nortestosterone_dodecylcarbonate" title="11β-Methyl-19-nortestosterone dodecylcarbonate">11β-Methyl-19-nortestosterone dodecylcarbonate</a></li> <li><a href="/wiki/19-Nor-5-androstenediol" title="19-Nor-5-androstenediol">19-Nor-5-androstenediol</a></li> <li><a href="/wiki/19-Nor-5-androstenedione" title="19-Nor-5-androstenedione">19-Nor-5-androstenedione</a></li> <li><a href="/wiki/19-Nordehydroepiandrosterone" title="19-Nordehydroepiandrosterone">19-Nordehydroepiandrosterone</a></li> <li><a href="/wiki/Bolandiol" title="Bolandiol">Bolandiol</a></li> <li><a href="/wiki/Bolandiol_dipropionate" title="Bolandiol dipropionate">Bolandiol dipropionate</a></li> <li><a href="/wiki/Bolandione" title="Bolandione">Bolandione</a></li> <li><a href="/wiki/Dimethisterone" title="Dimethisterone">Dimethisterone</a></li> <li><a href="/wiki/Dienedione" title="Dienedione">Dienedione</a></li> <li><a href="/wiki/Dienolone" title="Dienolone">Dienolone</a></li> <li><a href="/wiki/Dimethandrolone" title="Dimethandrolone">Dimethandrolone</a></li> <li><a href="/wiki/Dimethandrolone_buciclate" title="Dimethandrolone buciclate">Dimethandrolone buciclate</a></li> <li><a href="/wiki/Dimethandrolone_dodecylcarbonate" title="Dimethandrolone dodecylcarbonate">Dimethandrolone dodecylcarbonate</a></li> <li><a href="/wiki/Dimethandrolone_undecanoate" title="Dimethandrolone undecanoate">Dimethandrolone undecanoate</a></li> <li><a href="/wiki/Dimethyldienolone" title="Dimethyldienolone">Dimethyldienolone</a></li> <li><a href="/wiki/Dimethyltrienolone" title="Dimethyltrienolone">Dimethyltrienolone</a></li> <li><a href="/wiki/Ethyldienolone" title="Ethyldienolone">Ethyldienolone</a></li> <li><a href="/wiki/Ethylestrenol" title="Ethylestrenol">Ethylestrenol (ethylnandrol)</a></li> <li><a href="/wiki/Methyldienolone" title="Methyldienolone">Methyldienolone</a></li> <li><a href="/wiki/Metribolone" title="Metribolone">Metribolone (R-1881)</a></li> <li><a href="/wiki/Methoxydienone" title="Methoxydienone">Methoxydienone (methoxygonadiene)</a></li> <li><a href="/wiki/Mibolerone" title="Mibolerone">Mibolerone</a></li> <li><a href="/wiki/Nandrolone" title="Nandrolone">Nandrolone</a></li> <li><a href="/wiki/Nandrolone_ester" class="mw-redirect" title="Nandrolone ester">Nandrolone esters</a> (e.g., <a href="/wiki/Nandrolone_decanoate" title="Nandrolone decanoate">nandrolone decanoate</a>, <a href="/wiki/Nandrolone_phenylpropionate" title="Nandrolone phenylpropionate">nandrolone phenylpropionate</a>)</li> <li><a href="/wiki/Norethandrolone" title="Norethandrolone">Norethandrolone</a></li> <li><a href="/wiki/Normethandrone" title="Normethandrone">Normethandrone (methylestrenolone, normethandrolone, normethisterone)</a></li> <li><a href="/wiki/RU-2309" title="RU-2309">RU-2309</a></li> <li><a href="/wiki/Tetrahydrogestrinone" title="Tetrahydrogestrinone">Tetrahydrogestrinone</a></li> <li><a href="/wiki/Trenbolone" title="Trenbolone">Trenbolone (trienolone)</a></li> <li><a href="/wiki/Trenbolone_ester" class="mw-redirect" title="Trenbolone ester">Trenbolone esters</a> (e.g., <a href="/wiki/Trenbolone_acetate" title="Trenbolone acetate">trenbolone acetate</a>, <a href="/wiki/Trenbolone_enanthate" title="Trenbolone enanthate">trenbolone enanthate</a>)</li> <li><a href="/wiki/Trendione" title="Trendione">Trendione</a></li> <li><a href="/wiki/Trestolone" title="Trestolone">Trestolone</a></li> <li><a href="/wiki/Trestolone_acetate" title="Trestolone acetate">Trestolone acetate</a></li></ul> <ul><li><i>Spirolactone derivatives:</i> <a href="/wiki/Canrenoic_acid" title="Canrenoic acid">Canrenoic acid</a></li> <li><a href="/wiki/Canrenone" title="Canrenone">Canrenone</a></li> <li><a href="/wiki/Drospirenone" title="Drospirenone">Drospirenone</a></li> <li><a href="/wiki/Mespirenone" title="Mespirenone">Mespirenone</a></li> <li><a href="/wiki/Potassium_canrenoate" title="Potassium canrenoate">Potassium canrenoate</a></li> <li><a href="/wiki/Prorenone" title="Prorenone">Prorenone</a></li> <li><a href="/wiki/SC-5233" title="SC-5233">SC-5233 (spirolactone)</a></li> <li><a href="/wiki/SC-8109" title="SC-8109">SC-8109</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/wiki/Spirorenone" title="Spirorenone">Spirorenone</a></li></ul> <ul><li><i>Nonsteroidal:</i> <a href="/wiki/3,8-Dihydrodiligustilide" title="3,8-Dihydrodiligustilide">3,8-Dihydrodiligustilide</a></li> <li><a href="/wiki/LG-2527" title="LG-2527">LG-2527</a></li> <li><a href="/w/index.php?title=LG-100128&amp;action=edit&amp;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&amp;action=edit&amp;redlink=1" class="new" title="RWJ-26819 (page does not exist)">RWJ-26819</a></li> <li><a href="/w/index.php?title=RWJ-49853&amp;action=edit&amp;redlink=1" class="new" title="RWJ-49853 (page does not exist)">RWJ-49853</a></li> <li><a href="/w/index.php?title=RWJ-60130&amp;action=edit&amp;redlink=1" class="new" title="RWJ-60130 (page does not exist)">RWJ-60130</a></li> <li><a href="/wiki/Tanaproget" title="Tanaproget">Tanaproget</a></li> <li><a href="/wiki/ZM-182345" title="ZM-182345">ZM-182345</a></li></ul> <ul><li><i>Unknown:</i> <a href="/wiki/ORG-47241" title="ORG-47241">ORG-47241</a></li> <li><a href="/wiki/ORG-201745" title="ORG-201745">ORG-201745</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Mixed<br />(<a href="/wiki/Selective_progesterone_receptor_modulators" class="mw-redirect" title="Selective progesterone receptor modulators"><abbr title="Selective progesterone receptor modulators">SPRMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Selective progesterone receptor modulators</span>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Steroidal:</i> <a href="/wiki/Dihydroethisterone" class="mw-redirect" title="Dihydroethisterone">Dihydroethisterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydrolevonorgestrel" title="5α-Dihydrolevonorgestrel">5α-Dihydrolevonorgestrel</a></li> <li><a href="/wiki/5%CE%B1-Dihydronorethisterone" title="5α-Dihydronorethisterone">5α-Dihydronorethisterone</a></li> <li><a href="/wiki/Asoprisnil" title="Asoprisnil">Asoprisnil</a></li> <li><a href="/wiki/Asoprisnil_ecamate" title="Asoprisnil ecamate">Asoprisnil ecamate</a></li> <li><a href="/wiki/Guggulsterone" title="Guggulsterone">Guggulsterone</a></li> <li><a href="/w/index.php?title=J1042&amp;action=edit&amp;redlink=1" class="new" title="J1042 (page does not exist)">J1042</a></li> <li><a href="/w/index.php?title=LG-120838&amp;action=edit&amp;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&amp;action=edit&amp;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&amp;action=edit&amp;redlink=1" class="new" title="ORG-31710 (page does not exist)">ORG-31710</a></li> <li><a href="/w/index.php?title=ORG-33628&amp;action=edit&amp;redlink=1" class="new" title="ORG-33628 (page does not exist)">ORG-33628</a></li> <li><a href="/w/index.php?title=RMI-12936&amp;action=edit&amp;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&amp;action=edit&amp;redlink=1" class="new" title="ZK-137316 (page does not exist)">ZK-137316</a></li></ul> <ul><li><i>Nonsteroidal:</i> <a href="/wiki/Apigenin" title="Apigenin">Apigenin</a></li> <li><a href="/wiki/Kaempferol" title="Kaempferol">Kaempferol</a></li> <li><a href="/w/index.php?title=LG-120920&amp;action=edit&amp;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&amp;action=edit&amp;redlink=1" class="new" title="PRA-910 (page does not exist)">PRA-910</a></li> <li><a href="/wiki/Syringic_acid" title="Syringic acid">Syringic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Steroidal:</i> <a href="/wiki/Aglepristone" title="Aglepristone">Aglepristone</a></li> <li><a href="/wiki/Lilopristone" title="Lilopristone">Lilopristone</a></li> <li><a href="/wiki/Lonaprisan" title="Lonaprisan">Lonaprisan</a></li> <li><a href="/wiki/Onapristone" title="Onapristone">Onapristone</a></li> <li><a href="/w/index.php?title=ORG-31710&amp;action=edit&amp;redlink=1" class="new" title="ORG-31710 (page does not exist)">ORG-31710</a></li> <li><a href="/w/index.php?title=ORG-31806&amp;action=edit&amp;redlink=1" class="new" title="ORG-31806 (page does not exist)">ORG-31806</a></li> <li><a href="/w/index.php?title=ORG-33628&amp;action=edit&amp;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&amp;action=edit&amp;redlink=1" class="new" title="RTI 3021–022 (page does not exist)">RTI 3021–022</a></li> <li><a href="/wiki/Toripristone" title="Toripristone">Toripristone</a></li> <li><a href="/wiki/Zanoterone" title="Zanoterone">Zanoterone</a></li></ul> <ul><li><i>Nonsteroidal:</i> <a href="/wiki/Darolutamide" title="Darolutamide">Darolutamide</a></li> <li><a href="/w/index.php?title=LG-001447&amp;action=edit&amp;redlink=1" class="new" title="LG-001447 (page does not exist)">LG-001447</a></li> <li><a href="/w/index.php?title=LG-100127&amp;action=edit&amp;redlink=1" class="new" title="LG-100127 (page does not exist)">LG-100127</a></li> <li><a href="/w/index.php?title=LG-100128&amp;action=edit&amp;redlink=1" class="new" title="LG-100128 (page does not exist)">LG-100128</a></li> <li><a href="/w/index.php?title=LG-120830&amp;action=edit&amp;redlink=1" class="new" title="LG-120830 (page does not exist)">LG-120830</a></li> <li><a href="/w/index.php?title=LG-121046&amp;action=edit&amp;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&amp;action=edit&amp;redlink=1" class="new" title="ZM-150271 (page does not exist)">ZM-150271</a></li> <li><a href="/w/index.php?title=ZM-172406&amp;action=edit&amp;redlink=1" class="new" title="ZM-172406 (page does not exist)">ZM-172406</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Membrane_progesterone_receptor" title="Membrane progesterone receptor"><abbr title="Membrane progesterone receptor">mPR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Membrane progesterone receptor</span><br />(<a href="/wiki/Progestin_and_adipoQ_receptor" title="Progestin and adipoQ receptor"><abbr title="Progestin and adipoQ receptor">PAQR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Progestin and adipoQ receptor</span>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">5α-Dihydroprogesterone</a></li> <li><a href="/wiki/5%CE%B2-Dihydroprogesterone" title="5β-Dihydroprogesterone">5β-Dihydroprogesterone</a></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycortisone (21-hydroxyprogesterone)</a></li> <li><a href="/wiki/11-Deoxycortisol" title="11-Deoxycortisol">11-Deoxycortisol (17α,21-dihydroxyprogesterone)</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone</a></li> <li><a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Progestogens_and_antiprogestogens" title="Template:Progestogens and antiprogestogens">Progestogens and antiprogestogens</a></dd> <dd><a href="/wiki/Template:Androgen_receptor_modulators" title="Template:Androgen receptor modulators">Androgen receptor modulators</a></dd> <dd><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators">Estrogen receptor modulators</a></dd> <dd><a href="/wiki/List_of_steroidal_progestogens" class="mw-redirect" title="List of steroidal progestogens">List of progestogens</a></dd></dl> 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