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id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Pharmaceutical compound</div> <style data-mw-deduplicate="TemplateStyles:r1269284339">@media screen{html.skin-theme-clientpref-night .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}</style> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): BOMT">BOMT</span></caption><tbody><tr><td colspan="2" class="infobox-image"><span class="dark_mode_safe" typeof="mw:File"><a href="/wiki/File:BOMT.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f1/BOMT.svg/225px-BOMT.svg.png" decoding="async" width="225" height="166" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f1/BOMT.svg/338px-BOMT.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f1/BOMT.svg/450px-BOMT.svg.png 2x" data-file-width="1190" data-file-height="880" /></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;">Other names</th><td class="infobox-data">Ro 7-2340; 6α-Bromo-4-oxa-17α-methyl-5α-dihydrotestosterone; 6α-Bromo-4-oxa-17α-methyl-5α-androstan-17β-ol-3-one</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of<br />administration</a></th><td class="infobox-data"><a href="/wiki/Oral_administration" title="Oral administration">By mouth</a></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/Steroidal_antiandrogen" title="Steroidal antiandrogen">Steroidal antiandrogen</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li>None</li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">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%;">(1<i>S</i>,3a<i>S</i>,3b<i>R</i>,5<i>S</i>,5a<i>S</i>,9a<i>R</i>,9b<i>S</i>,11a<i>S</i>)-5-Bromo-1-hydroxy-1,9a,11a-trimethyl-2,3,3a,3b,4,5,5a,8,9,9b,10,11-dodecahydroindeno[5,4-<i>f</i>]chromen-7-one</div></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=24543-59-7">24543-59-7</a></span> <br />24543-66-6</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/159972">159972</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.140636.html">140636</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/DTXSID80947424">DTXSID80947424</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q28209089#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 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>19</sub><span title="Hydrogen">H</span><sub>29</sub><span title="Bromine">Br</span><span title="Oxygen">O</span><sub>3</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="7002385342000000000♠"></span>385.342</span> g·mol<sup>−1</sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CC12CCC%28%3DO%29OC1C%28CC3C2CCC4%28C3CCC4%28C%29O%29C%29Br">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%;">CC12CCC(=O)OC1C(CC3C2CCC4(C3CCC4(C)O)C)Br</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/C19H29BrO3/c1-17-7-6-15(21)23-16(17)14(20)10-11-12(17)4-8-18(2)13(11)5-9-19(18,3)22/h11-14,16,22H,4-10H2,1-3H3/t11-,12+,13+,14+,16-,17-,18+,19+/m1/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:ZUIGZKIOHUNINA-LWPUPYOYSA-N</div></li></ul> </div></td></tr></tbody></table> <p><b>BOMT</b>, also known by its developmental code name <b>Ro 7-2340</b> and as <b>6α-bromo-4-oxa-17α-methyl-5α-dihydrotestosterone</b>, is a <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">synthetic</a> <a href="/wiki/Steroidal_antiandrogen" title="Steroidal antiandrogen">steroidal antiandrogen</a> which was first produced in 1970 and was never marketed for medical use.<sup id="cite_ref-Elks2014_1-0" class="reference"><a href="#cite_note-Elks2014-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-BorisUskokovic1970_2-0" class="reference"><a href="#cite_note-BorisUskokovic1970-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-BorisDemartino1971_3-0" class="reference"><a href="#cite_note-BorisDemartino1971-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ManganMainwaring1972_4-0" class="reference"><a href="#cite_note-ManganMainwaring1972-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> It is the 6α-<a href="/wiki/Bromine" title="Bromine"><b>b</b>rominated</a>, 4-<a href="/wiki/Oxygen" title="Oxygen"><b>o</b>xygenated</a>, and 17α-<a href="/wiki/Methyl_group" title="Methyl group"><b>m</b>ethylated</a> <a href="/wiki/Chemical_derivative" class="mw-redirect" title="Chemical derivative">derivative</a> of the <a href="/wiki/Androgen" title="Androgen">androgen</a> <a href="/wiki/Dihydrotestosterone" title="Dihydrotestosterone">dihydro<b>t</b>estosterone</a> (DHT). Along with <a href="/wiki/Benorterone" title="Benorterone">benorterone</a>, <a href="/wiki/Cyproterone" title="Cyproterone">cyproterone</a> (and its C17α <a href="/wiki/Acetate" title="Acetate">acetate</a> <a href="/wiki/Ester" title="Ester">ester</a>, <a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">cyproterone acetate</a>), and <a href="/wiki/Flutamide" title="Flutamide">flutamide</a>,<sup id="cite_ref-MannLutwak-Mann2012_5-0" class="reference"><a href="#cite_note-MannLutwak-Mann2012-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> BOMT was among the earliest antiandrogens to be developed and extensively studied,<sup id="cite_ref-BorisUskokovic1970_2-1" class="reference"><a href="#cite_note-BorisUskokovic1970-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-BorisDemartino1971_3-1" class="reference"><a href="#cite_note-BorisDemartino1971-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Mainwaring_2012_6-0" class="reference"><a href="#cite_note-Mainwaring_2012-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Bratoeff_1999_7-0" class="reference"><a href="#cite_note-Bratoeff_1999-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> although it is less well-documented in comparison to the others.<sup id="cite_ref-Clark_1979_8-0" class="reference"><a href="#cite_note-Clark_1979-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> BOMT has been investigated clinically in the treatment of <a href="/wiki/Benign_prostatic_hyperplasia" title="Benign prostatic hyperplasia">benign prostatic hyperplasia</a>, though development for this use did not continue.<sup id="cite_ref-KentBischoff_9-0" class="reference"><a href="#cite_note-KentBischoff-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> There was also interest in BOMT for the potential applications of <a href="/wiki/Acne" title="Acne">acne</a>, <a href="/wiki/Pattern_hair_loss" title="Pattern hair loss">pattern hair loss</a>, and possibly <a href="/wiki/Prostate_cancer" title="Prostate cancer">prostate cancer</a>, but it was not developed for these indications either.<sup id="cite_ref-O'Mainwaring_1973_10-0" class="reference"><a href="#cite_note-O'Mainwaring_1973-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>BOMT is a <a href="/wiki/Binding_selectivity" title="Binding selectivity">selective</a> <a href="/wiki/Competitive_antagonist" class="mw-redirect" title="Competitive antagonist">competitive antagonist</a> of the <a href="/wiki/Androgen_receptor" title="Androgen receptor">androgen receptor</a> (AR),<sup id="cite_ref-BorisDemartino1971_3-2" class="reference"><a href="#cite_note-BorisDemartino1971-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ManganMainwaring1972_4-1" class="reference"><a href="#cite_note-ManganMainwaring1972-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Setchell1978_11-0" class="reference"><a href="#cite_note-Setchell1978-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-KingMainwaring2014_12-0" class="reference"><a href="#cite_note-KingMainwaring2014-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SinghGauthier2000_13-0" class="reference"><a href="#cite_note-SinghGauthier2000-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> although it is described as an "only relatively weak competitor."<sup id="cite_ref-HeynsG.1976_14-0" class="reference"><a href="#cite_note-HeynsG.1976-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Relative_binding_affinity" class="mw-redirect" title="Relative binding affinity">relative binding affinity</a> of the drug for the androgen receptor is about 2.7% of that of <a href="/wiki/Metribolone" title="Metribolone">metribolone</a>.<sup id="cite_ref-pmid7339263_15-0" class="reference"><a href="#cite_note-pmid7339263-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> BOMT shows no <a href="/wiki/Androgen" title="Androgen">androgenic</a>, <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogenic</a>, or <a href="/wiki/Progestogen" title="Progestogen">progestogenic</a> activity even at high doses, nor any <a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibition</a> of <a href="/wiki/5%CE%B1-reductase" class="mw-redirect" title="5α-reductase">5α-reductase</a>,<sup id="cite_ref-ManganMainwaring1971_16-0" class="reference"><a href="#cite_note-ManganMainwaring1971-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> though it has been reported to possess weak <a href="/wiki/Antigonadotropic" class="mw-redirect" title="Antigonadotropic">antigonadotropic</a> effects.<sup id="cite_ref-BorisDemartino1971_3-3" class="reference"><a href="#cite_note-BorisDemartino1971-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ManganMainwaring1972_4-2" class="reference"><a href="#cite_note-ManganMainwaring1972-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Setchell1978_11-1" class="reference"><a href="#cite_note-Setchell1978-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-KingMainwaring2014_12-1" class="reference"><a href="#cite_note-KingMainwaring2014-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> Due to its selectivity for and competitive inhibition of the AR, BOMT has been described as a pure or "true" antiandrogen, similarly to benorterone, cyproterone, and flutamide.<sup id="cite_ref-Tremblay1986_17-0" class="reference"><a href="#cite_note-Tremblay1986-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> Like other steroidal antiandrogens, BOMT may actually be a weak <a href="/wiki/Partial_agonist" title="Partial agonist">partial agonist</a> of the AR, as it appears to have the potential for weak androgenic effects in specific situations.<sup id="cite_ref-pmid1217898_18-0" class="reference"><a href="#cite_note-pmid1217898-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> On the basis of <a href="/wiki/Animal_research" class="mw-redirect" title="Animal research">animal research</a>, BOMT does not appear to act as an AR antagonist in <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a> <a href="/wiki/Tissue_(biology)" title="Tissue (biology)">tissues</a>, and in relation to this, does not disinhibit the <a href="/wiki/Hypothalamic%E2%80%93pituitary%E2%80%93gonadal_axis" title="Hypothalamic–pituitary–gonadal axis">hypothalamic–pituitary–gonadal axis</a> or increase <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> levels.<sup id="cite_ref-ClarkNowell1979b_19-0" class="reference"><a href="#cite_note-ClarkNowell1979b-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</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=BOMT&action=edit&section=1" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/List_of_steroidal_antiandrogens" title="List of steroidal antiandrogens">List of steroidal antiandrogens</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=BOMT&action=edit&section=2" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-Elks2014-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-Elks2014_1-0">^</a></b></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="CITEREFElks2014" class="citation book cs1">Elks J (14 November 2014). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA178"><i>The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies</i></a>. Springer. pp. 178–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4757-2085-3" title="Special:BookSources/978-1-4757-2085-3"><bdi>978-1-4757-2085-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Dictionary+of+Drugs%3A+Chemical+Data%3A+Chemical+Data%2C+Structures+and+Bibliographies&rft.pages=178-&rft.pub=Springer&rft.date=2014-11-14&rft.isbn=978-1-4757-2085-3&rft.aulast=Elks&rft.aufirst=J&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D0vXTBwAAQBAJ%26pg%3DPA178&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABOMT" class="Z3988"></span></span> </li> <li id="cite_note-BorisUskokovic1970-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-BorisUskokovic1970_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-BorisUskokovic1970_2-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBorisUskoković1970" class="citation journal cs1">Boris A, Uskoković M (January 1970). "A new antiandrogen, 6alpha-bromo-17 beta-hydroxy-17 alpha-methyl-4-oxa-5 alpha-androstan-3-one". <i>Experientia</i>. <b>26</b> (1): <span class="nowrap">9–</span>10. <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%2FBF01900355">10.1007/BF01900355</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/5412314">5412314</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:39460337">39460337</a>. <q>[It is shown that 6α-bromo-17β-hydroxy-17α-methyl-4-oxa-5α-androstan-3-one, has significant anti-androgenic activity. Isomers of this compound with different configuration at C-5 and C-6 were found to be inactive.]</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Experientia&rft.atitle=A+new+antiandrogen%2C+6alpha-bromo-17+beta-hydroxy-17+alpha-methyl-4-oxa-5+alpha-androstan-3-one&rft.volume=26&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E9-%3C%2Fspan%3E10&rft.date=1970-01&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A39460337%23id-name%3DS2CID&rft_id=info%3Apmid%2F5412314&rft_id=info%3Adoi%2F10.1007%2FBF01900355&rft.aulast=Boris&rft.aufirst=A&rft.au=Uskokovi%C4%87%2C+M&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABOMT" class="Z3988"></span></span> </li> <li id="cite_note-BorisDemartino1971-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-BorisDemartino1971_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-BorisDemartino1971_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-BorisDemartino1971_3-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-BorisDemartino1971_3-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBorisDeMartinoTrmal1971" class="citation journal cs1">Boris A, DeMartino L, Trmal T (April 1971). <a rel="nofollow" class="external text" href="https://doi.org/10.1210%2Fendo-88-4-1086">"Some endocrine studies of a new antiandrogen, 6-alpha-bromo-17-beta-hydroxy-17-alpha-methyl-4-oxa-5-alpha-androstan-3-one (BOMT)"</a>. <i>Endocrinology</i>. <b>88</b> (4): <span class="nowrap">1086–</span>1091. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1210%2Fendo-88-4-1086">10.1210/endo-88-4-1086</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/5542403">5542403</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Endocrinology&rft.atitle=Some+endocrine+studies+of+a+new+antiandrogen%2C+6-alpha-bromo-17-beta-hydroxy-17-alpha-methyl-4-oxa-5-alpha-androstan-3-one+%28BOMT%29&rft.volume=88&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1086-%3C%2Fspan%3E1091&rft.date=1971-04&rft_id=info%3Adoi%2F10.1210%2Fendo-88-4-1086&rft_id=info%3Apmid%2F5542403&rft.aulast=Boris&rft.aufirst=A&rft.au=DeMartino%2C+L&rft.au=Trmal%2C+T&rft_id=https%3A%2F%2Fdoi.org%2F10.1210%252Fendo-88-4-1086&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABOMT" class="Z3988"></span></span> </li> <li id="cite_note-ManganMainwaring1972-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-ManganMainwaring1972_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-ManganMainwaring1972_4-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-ManganMainwaring1972_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="CITEREFManganMainwaring1972" class="citation journal cs1">Mangan FR, Mainwaring WI (September 1972). "An explanation of the antiandrogenic properties of 6 -bromo-17 -hydroxy-17 -methyl-4-oxa-5 -androstane-3-one". <i>Steroids</i>. <b>20</b> (3): <span class="nowrap">331–</span>343. <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%2F0039-128X%2872%2990092-X">10.1016/0039-128X(72)90092-X</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/5073580">5073580</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Steroids&rft.atitle=An+explanation+of+the+antiandrogenic+properties+of+6+-bromo-17+-hydroxy-17+-methyl-4-oxa-5+-androstane-3-one&rft.volume=20&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E331-%3C%2Fspan%3E343&rft.date=1972-09&rft_id=info%3Adoi%2F10.1016%2F0039-128X%2872%2990092-X&rft_id=info%3Apmid%2F5073580&rft.aulast=Mangan&rft.aufirst=FR&rft.au=Mainwaring%2C+WI&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABOMT" class="Z3988"></span></span> </li> <li id="cite_note-MannLutwak-Mann2012-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-MannLutwak-Mann2012_5-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMannLutwak-Mann2012" class="citation book cs1">Mann T, Lutwak-Mann C (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=cezjBwAAQBAJ&pg=PA352">"Antiandrogens"</a>. <i>Male Reproductive Function and Semen: Themes and Trends in Physiology, Biochemistry and Investigative Andrology</i>. Springer Science & Business Media. pp. 352–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4471-1300-3" title="Special:BookSources/978-1-4471-1300-3"><bdi>978-1-4471-1300-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Antiandrogens&rft.btitle=Male+Reproductive+Function+and+Semen%3A+Themes+and+Trends+in+Physiology%2C+Biochemistry+and+Investigative+Andrology&rft.pages=352-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-1-4471-1300-3&rft.aulast=Mann&rft.aufirst=T&rft.au=Lutwak-Mann%2C+C&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DcezjBwAAQBAJ%26pg%3DPA352&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABOMT" class="Z3988"></span></span> </li> <li id="cite_note-Mainwaring_2012-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-Mainwaring_2012_6-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMainwaring2012" class="citation book cs1">Mainwaring WI (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=rrDoCAAAQBAJ&pg=PA10"><i>The Mechanism of Action of Androgens</i></a>. Springer Science & Business Media. pp. 10–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-88429-0" title="Special:BookSources/978-3-642-88429-0"><bdi>978-3-642-88429-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Mechanism+of+Action+of+Androgens&rft.pages=10-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-3-642-88429-0&rft.aulast=Mainwaring&rft.aufirst=WI&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DrrDoCAAAQBAJ%26pg%3DPA10&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABOMT" class="Z3988"></span></span> </li> <li id="cite_note-Bratoeff_1999-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-Bratoeff_1999_7-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBratoeffRamírezMurilloFlores1999" class="citation journal cs1">Bratoeff E, Ramírez E, Murillo E, Flores G, Cabeza M (December 1999). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=2zI4_gEr80IC&pg=PA1110">"Steroidal antiandrogens and 5alpha-reductase inhibitors"</a>. <i>Current Medicinal Chemistry</i>. <b>6</b> (12): <span class="nowrap">1107–</span>23. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.2174%2F0929867306666220401180500">10.2174/0929867306666220401180500</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/10519917">10519917</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:248057720">248057720</a>. <q>Several androstane derivatives have also demonstrated an antiandrogenic activity; 17α-methyl-<i>B</i>-nortestosterone 8 was prepared and tested in 1964 for antihormonal activity [43]. Within the next decades, several other androstane analogs were prepared and found to possess antiandrogenic activity [43, 44, 45, 46] including BOMT 9 "figure 2", R2956 10, SC9420 11, and oxendolone 12 "figure 3".</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Current+Medicinal+Chemistry&rft.atitle=Steroidal+antiandrogens+and+5alpha-reductase+inhibitors&rft.volume=6&rft.issue=12&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1107-%3C%2Fspan%3E23&rft.date=1999-12&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A248057720%23id-name%3DS2CID&rft_id=info%3Apmid%2F10519917&rft_id=info%3Adoi%2F10.2174%2F0929867306666220401180500&rft.aulast=Bratoeff&rft.aufirst=E&rft.au=Ram%C3%ADrez%2C+E&rft.au=Murillo%2C+E&rft.au=Flores%2C+G&rft.au=Cabeza%2C+M&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D2zI4_gEr80IC%26pg%3DPA1110&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABOMT" class="Z3988"></span></span> </li> <li id="cite_note-Clark_1979-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-Clark_1979_8-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFClarkNowell1979" class="citation journal cs1">Clark CR, Nowell NW (April 1979). "Binding properties of testosterone receptors in the hypothalamic-preoptic area of the adult male mouse brain". <i>Steroids</i>. <b>33</b> (4): <span class="nowrap">407–</span>426. <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%2F0039-128X%2879%2990015-1">10.1016/0039-128X(79)90015-1</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/442132">442132</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:42014129">42014129</a>. <q>However, a less well documented antiandrogen, BOMT possesses the ideal characteristics of negligible androgenic, estrogenic and progestational activity (55) and would therefore appear to be a valuable compound for use in future investigations.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Steroids&rft.atitle=Binding+properties+of+testosterone+receptors+in+the+hypothalamic-preoptic+area+of+the+adult+male+mouse+brain&rft.volume=33&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E407-%3C%2Fspan%3E426&rft.date=1979-04&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A42014129%23id-name%3DS2CID&rft_id=info%3Apmid%2F442132&rft_id=info%3Adoi%2F10.1016%2F0039-128X%2879%2990015-1&rft.aulast=Clark&rft.aufirst=CR&rft.au=Nowell%2C+NW&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABOMT" class="Z3988"></span></span> </li> <li id="cite_note-KentBischoff-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-KentBischoff_9-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKentBischoffHerrO'Connell1973" class="citation cs2">Kent J, Bischoff A, Herr H, O'Connell W (1973), <a rel="nofollow" class="external text" href="https://books.google.com/books?id=9b5GAQAAMAAJ&q=%22Ro+7-2340%22"><i>Study of antiandrogen (Ro–7–2340) (6α-bromo-17β-methyl-4-oxa-5α-andronstan-3-one) in benign prostatic hypertrophy</i></a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Study+of+antiandrogen+%28Ro%E2%80%937%E2%80%932340%29+%286%CE%B1-bromo-17%CE%B2-methyl-4-oxa-5%CE%B1-andronstan-3-one%29+in+benign+prostatic+hypertrophy&rft.date=1973&rft.aulast=Kent&rft.aufirst=J&rft.au=Bischoff%2C+A&rft.au=Herr%2C+H&rft.au=O%27Connell%2C+W&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D9b5GAQAAMAAJ%26q%3D%2522Ro%2B7-2340%2522&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABOMT" class="Z3988"></span></span> </li> <li id="cite_note-O'Mainwaring_1973-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-O'Mainwaring_1973_10-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMainwaringManganWilceMilroy1973" class="citation book cs1">Mainwaring WI, Mangan FR, Wilce PA, Milroy EG (1973). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=_KnaBwAAQBAJ&pg=PA208">"Androgens I. — A Review of Current Research on the Binding and Mechanism of Action of Androgenic Steroids, Notably 5α-Dihydrotestosterone"</a>. <i>Receptors for Reproductive Hormones</i>. Advances in Experimental Medicine and Biology. Vol. 36. pp. 197–231 (208). <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%2F978-1-4684-3237-4_10">10.1007/978-1-4684-3237-4_10</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4684-3239-8" title="Special:BookSources/978-1-4684-3239-8"><bdi>978-1-4684-3239-8</bdi></a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/4368414">4368414</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Androgens+I.+%E2%80%94+A+Review+of+Current+Research+on+the+Binding+and+Mechanism+of+Action+of+Androgenic+Steroids%2C+Notably+5%CE%B1-Dihydrotestosterone&rft.btitle=Receptors+for+Reproductive+Hormones&rft.series=Advances+in+Experimental+Medicine+and+Biology&rft.pages=197-231+%28208%29&rft.date=1973&rft_id=info%3Apmid%2F4368414&rft_id=info%3Adoi%2F10.1007%2F978-1-4684-3237-4_10&rft.isbn=978-1-4684-3239-8&rft.aulast=Mainwaring&rft.aufirst=WI&rft.au=Mangan%2C+FR&rft.au=Wilce%2C+PA&rft.au=Milroy%2C+EG&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D_KnaBwAAQBAJ%26pg%3DPA208&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABOMT" class="Z3988"></span></span> </li> <li id="cite_note-Setchell1978-11"><span class="mw-cite-backlink">^ <a href="#cite_ref-Setchell1978_11-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Setchell1978_11-1"><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="CITEREFSetchell1978" class="citation book cs1">Setchell BP (1978). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=d4l9AAAAIAAJ"><i>The mammalian testis</i></a>. P. Elek. p. 144. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-236-31057-9" title="Special:BookSources/978-0-236-31057-9"><bdi>978-0-236-31057-9</bdi></a>. <q>Another steroidal compound with anti-androgenic activity is BOMT (6α-bromo-17β-hydroxy-17α-methyl-4-oxa-5α-androstan-3-one). This compound has no androgenic, oestrogenic or progestational activity but is a potent anti-androgen and (Boris et al., 1970); it competes effectively for the specific, high-affinity binding sites for DHT in the rat prostate (Mangan and Mainwaring, 1972) and depresses testis weight (Boris et al., 1970).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+mammalian+testis&rft.pages=144&rft.pub=P.+Elek&rft.date=1978&rft.isbn=978-0-236-31057-9&rft.aulast=Setchell&rft.aufirst=BP&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dd4l9AAAAIAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABOMT" class="Z3988"></span></span> </li> <li id="cite_note-KingMainwaring2014-12"><span class="mw-cite-backlink">^ <a href="#cite_ref-KingMainwaring2014_12-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-KingMainwaring2014_12-1"><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="CITEREFKingMainwaring2014" class="citation book cs1">King RJ, Mainwaring WI (20 May 2014). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=QxajBQAAQBAJ&pg=PA52"><i>Steroid–Cell Interactions</i></a>. Elsevier. pp. 52, 61, <span class="nowrap">70–</span>71, 300, <span class="nowrap">401–</span>403. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4831-6510-3" title="Special:BookSources/978-1-4831-6510-3"><bdi>978-1-4831-6510-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Steroid%E2%80%93Cell+Interactions&rft.pages=52%2C+61%2C+%3Cspan+class%3D%22nowrap%22%3E70-%3C%2Fspan%3E71%2C+300%2C+%3Cspan+class%3D%22nowrap%22%3E401-%3C%2Fspan%3E403&rft.pub=Elsevier&rft.date=2014-05-20&rft.isbn=978-1-4831-6510-3&rft.aulast=King&rft.aufirst=RJ&rft.au=Mainwaring%2C+WI&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DQxajBQAAQBAJ%26pg%3DPA52&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABOMT" class="Z3988"></span></span> </li> <li id="cite_note-SinghGauthier2000-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-SinghGauthier2000_13-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSinghGauthierLabrie2000" class="citation journal cs1">Singh SM, Gauthier S, Labrie F (February 2000). "Androgen receptor antagonists (antiandrogens): structure-activity relationships". <i>Current Medicinal Chemistry</i>. <b>7</b> (2): <span class="nowrap">211–</span>247. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.2174%2F0929867003375371">10.2174/0929867003375371</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/10637363">10637363</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Current+Medicinal+Chemistry&rft.atitle=Androgen+receptor+antagonists+%28antiandrogens%29%3A+structure-activity+relationships&rft.volume=7&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E211-%3C%2Fspan%3E247&rft.date=2000-02&rft_id=info%3Adoi%2F10.2174%2F0929867003375371&rft_id=info%3Apmid%2F10637363&rft.aulast=Singh&rft.aufirst=SM&rft.au=Gauthier%2C+S&rft.au=Labrie%2C+F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABOMT" class="Z3988"></span></span> </li> <li id="cite_note-HeynsG.1976-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-HeynsG.1976_14-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHeynsVerhoevenDe_Moor1976" class="citation journal cs1">Heyns W, Verhoeven G, De Moor P (May 1976). "Androgen binding in rat uterus cytosol. Study of the specificity". <i>Journal of Steroid Biochemistry</i>. <b>7</b> (5): <span class="nowrap">335–</span>343. <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%2876%2990092-3">10.1016/0022-4731(76)90092-3</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/180344">180344</a>. <q>Finally, the steroidal antiandrogen BOMT and the non-steroidal antiandrogen DIMP are only relatively weak competitors.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Steroid+Biochemistry&rft.atitle=Androgen+binding+in+rat+uterus+cytosol.+Study+of+the+specificity&rft.volume=7&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E335-%3C%2Fspan%3E343&rft.date=1976-05&rft_id=info%3Adoi%2F10.1016%2F0022-4731%2876%2990092-3&rft_id=info%3Apmid%2F180344&rft.aulast=Heyns&rft.aufirst=W&rft.au=Verhoeven%2C+G&rft.au=De+Moor%2C+P&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABOMT" class="Z3988"></span></span> </li> <li id="cite_note-pmid7339263-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid7339263_15-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWakelingFurrGlenHughes1981" class="citation journal cs1">Wakeling AE, Furr BJ, Glen AT, Hughes LR (December 1981). "Receptor binding and biological activity of steroidal and nonsteroidal antiandrogens". <i>Journal of Steroid Biochemistry</i>. <b>15</b>: <span class="nowrap">355–</span>359. <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%2881%2990297-1">10.1016/0022-4731(81)90297-1</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/7339263">7339263</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Steroid+Biochemistry&rft.atitle=Receptor+binding+and+biological+activity+of+steroidal+and+nonsteroidal+antiandrogens&rft.volume=15&rft.pages=%3Cspan+class%3D%22nowrap%22%3E355-%3C%2Fspan%3E359&rft.date=1981-12&rft_id=info%3Adoi%2F10.1016%2F0022-4731%2881%2990297-1&rft_id=info%3Apmid%2F7339263&rft.aulast=Wakeling&rft.aufirst=AE&rft.au=Furr%2C+BJ&rft.au=Glen%2C+AT&rft.au=Hughes%2C+LR&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABOMT" class="Z3988"></span></span> </li> <li id="cite_note-ManganMainwaring1971-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-ManganMainwaring1971_16-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFManganMainwaring1971" class="citation journal cs1">Mangan FR, Mainwaring WI (1971). "The biochemical basis for the antagonism by BOMT of the effects of dihydrotesterone on the rat ventral prostate gland". <i>Gynecologic Investigation</i>. <b>2</b> (1): <span class="nowrap">300–</span>304. <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%2F000301871">10.1159/000301871</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/5161490">5161490</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Gynecologic+Investigation&rft.atitle=The+biochemical+basis+for+the+antagonism+by+BOMT+of+the+effects+of+dihydrotesterone+on+the+rat+ventral+prostate+gland&rft.volume=2&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E300-%3C%2Fspan%3E304&rft.date=1971&rft_id=info%3Adoi%2F10.1159%2F000301871&rft_id=info%3Apmid%2F5161490&rft.aulast=Mangan&rft.aufirst=FR&rft.au=Mainwaring%2C+WI&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABOMT" class="Z3988"></span></span> </li> <li id="cite_note-Tremblay1986-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-Tremblay1986_17-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFTremblay1986" class="citation journal cs1">Tremblay RR (May 1986). "Treatment of hirsutism with spironolactone". <i>Clinics in Endocrinology and Metabolism</i>. <b>15</b> (2): <span class="nowrap">363–</span>371. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0300-595X%2886%2980030-5">10.1016/S0300-595X(86)80030-5</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/2941190">2941190</a>. <q>Flutamide, cyproterone, benorterone, RU-2956, BOMT and cimetidine are recognized as true antiandrogens because they act as competitive inhibitors of specific ligand binding to androgen receptors.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Clinics+in+Endocrinology+and+Metabolism&rft.atitle=Treatment+of+hirsutism+with+spironolactone&rft.volume=15&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E363-%3C%2Fspan%3E371&rft.date=1986-05&rft_id=info%3Adoi%2F10.1016%2FS0300-595X%2886%2980030-5&rft_id=info%3Apmid%2F2941190&rft.aulast=Tremblay&rft.aufirst=RR&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABOMT" class="Z3988"></span></span> </li> <li id="cite_note-pmid1217898-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid1217898_18-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFAhlinForsbergJacobsohnThore-Berger1975" class="citation journal cs1">Ahlin K, Forsberg JG, Jacobsohn D, Thore-Berger B (1975). "The male genital tract and the nipples of male and female offspring of rats given the non-steroidal antiandrogens DIMP and Sch 13521, during pregnancy". <i>Archives d'Anatomie Microscopique et de Morphologie Expérimentale</i>. <b>64</b> (1): <span class="nowrap">27–</span>44. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/1217898">1217898</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Archives+d%27Anatomie+Microscopique+et+de+Morphologie+Exp%C3%A9rimentale&rft.atitle=The+male+genital+tract+and+the+nipples+of+male+and+female+offspring+of+rats+given+the+non-steroidal+antiandrogens+DIMP+and+Sch+13521%2C+during+pregnancy&rft.volume=64&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E27-%3C%2Fspan%3E44&rft.date=1975&rft_id=info%3Apmid%2F1217898&rft.aulast=Ahlin&rft.aufirst=K&rft.au=Forsberg%2C+JG&rft.au=Jacobsohn%2C+D&rft.au=Thore-Berger%2C+B&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABOMT" class="Z3988"></span></span> </li> <li id="cite_note-ClarkNowell1979b-19"><span class="mw-cite-backlink"><b><a href="#cite_ref-ClarkNowell1979b_19-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFClarkNowell1979" class="citation journal cs1">Clark CR, Nowell NW (August 1979). "BOMT (6 alpha-bromo-17 beta-hydroxy-17 alpha-methyl-4-oxa-5 alpha-androstan-3-one) is not an androgen antagonist within the central nervous system". <i>Steroids</i>. <b>34</b> (2): <span class="nowrap">139–</span>149. <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%2F0039-128X%2879%2990043-6">10.1016/0039-128X(79)90043-6</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/494357">494357</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:54290381">54290381</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Steroids&rft.atitle=BOMT+%286+alpha-bromo-17+beta-hydroxy-17+alpha-methyl-4-oxa-5+alpha-androstan-3-one%29+is+not+an+androgen+antagonist+within+the+central+nervous+system&rft.volume=34&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E139-%3C%2Fspan%3E149&rft.date=1979-08&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A54290381%23id-name%3DS2CID&rft_id=info%3Apmid%2F494357&rft_id=info%3Adoi%2F10.1016%2F0039-128X%2879%2990043-6&rft.aulast=Clark&rft.aufirst=CR&rft.au=Nowell%2C+NW&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABOMT" class="Z3988"></span></span> </li> </ol></div></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist 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href="/wiki/Template:Androgen_receptor_modulators" title="Template:Androgen receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Androgen_receptor_modulators" title="Template talk:Androgen receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Androgen_receptor_modulators" title="Special:EditPage/Template:Androgen receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Androgen_receptor_modulators801" style="font-size:114%;margin:0 4em"><a href="/wiki/Androgen_receptor" title="Androgen receptor">Androgen receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Androgen_receptor" title="Androgen receptor"><abbr title="Androgen receptor">AR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Androgen receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Testosterone derivatives:</i> <a href="/wiki/4-Androstenediol" title="4-Androstenediol">4-Androstenediol</a></li> <li><a href="/wiki/4-Dehydroepiandrosterone" title="4-Dehydroepiandrosterone">4-Dehydroepiandrosterone (4-DHEA)</a></li> <li><a href="/wiki/4-Hydroxytestosterone" title="4-Hydroxytestosterone">4-Hydroxytestosterone</a></li> <li><a href="/w/index.php?title=4,17%CE%B1-Dimethyltestosterone&action=edit&redlink=1" class="new" title="4,17α-Dimethyltestosterone (page does not exist)">4,17α-Dimethyltestosterone</a></li> <li><a href="/wiki/5-Androstenedione" title="5-Androstenedione">5-Androstenedione</a></li> <li><a href="/wiki/11-Ketotestosterone" title="11-Ketotestosterone">11-Ketotestosterone</a></li> <li><a href="/wiki/11%CE%B2-Hydroxyandrostenedione" title="11β-Hydroxyandrostenedione">11β-Hydroxyandrostenedione</a></li> <li><a href="/wiki/Adrenosterone" title="Adrenosterone">Adrenosterone (11-ketoandrostenedione, 11-oxoandrostenedione)</a></li> <li><a href="/wiki/5-Androstenediol" class="mw-redirect" title="5-Androstenediol">Androstenediol (5-androstenediol)</a> <ul><li><a href="/wiki/Androstenediol_3%CE%B2-acetate" title="Androstenediol 3β-acetate">Androstenediol 3β-acetate</a></li> <li><a href="/wiki/Androstenediol_17%CE%B2-acetate" title="Androstenediol 17β-acetate">Androstenediol 17β-acetate</a></li> <li><a href="/wiki/Androstenediol_diacetate" title="Androstenediol diacetate">Androstenediol diacetate</a></li> <li><a href="/wiki/Androstenediol_dipropionate" title="Androstenediol dipropionate">Androstenediol dipropionate</a></li></ul></li> <li><a href="/wiki/4-Androstenedione" class="mw-redirect" title="4-Androstenedione">Androstenedione (4-androstenedione)</a></li> <li><a href="/wiki/Atamestane" title="Atamestane">Atamestane</a></li> <li><a href="/wiki/Boldenone" title="Boldenone">Boldenone</a> <ul><li><a href="/wiki/Boldenone_undecylenate" title="Boldenone undecylenate">Boldenone undecylenate</a></li></ul></li> <li><a href="/wiki/Boldione" title="Boldione">Boldione (1,4-androstadienedione)</a></li> <li><a href="/wiki/Clostebol" title="Clostebol">Clostebol</a> <ul><li><a href="/wiki/Clostebol_acetate" title="Clostebol acetate">Clostebol acetate</a></li> <li><a href="/wiki/Clostebol_caproate" title="Clostebol caproate">Clostebol caproate</a></li> <li><a href="/wiki/Clostebol_propionate" title="Clostebol propionate">Clostebol propionate</a></li></ul></li> <li><a href="/wiki/Cloxotestosterone" title="Cloxotestosterone">Cloxotestosterone</a> <ul><li><a href="/wiki/Cloxotestosterone_acetate" title="Cloxotestosterone acetate">Cloxotestosterone acetate</a></li></ul></li> <li><a href="/wiki/Dehydroandrosterone" title="Dehydroandrosterone">Dehydroandrosterone</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA (androstenolone, prasterone; 5-DHEA)</a> <ul><li><a href="/wiki/Prasterone_enanthate" title="Prasterone enanthate">DHEA enanthate (prasterone enanthate)</a></li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA sulfate</a></li></ul></li> <li><a href="/wiki/Exemestane" title="Exemestane">Exemestane</a></li> <li><a href="/wiki/Formestane" title="Formestane">Formestane</a></li> <li><a href="/wiki/Plomestane" title="Plomestane">Plomestane</a></li> <li><a href="/wiki/Quinbolone" title="Quinbolone">Quinbolone</a></li> <li><a href="/wiki/Silandrone" title="Silandrone">Silandrone</a></li> <li><a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">Testosterone</a><sup>#</sup> (<a href="/wiki/Testosterone/dutasteride" title="Testosterone/dutasteride">+dutasteride</a>) <ul><li><a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">Testosterone esters</a></li> <li><a href="/wiki/Polytestosterone_phloretin_phosphate" title="Polytestosterone phloretin phosphate">Polytestosterone phloretin phosphate</a></li></ul></li></ul> <ul><li><i>5α-Dihydrotestosterone derivatives:</i> <a href="/wiki/1-Androstenediol" title="1-Androstenediol">1-Androstenediol</a></li> <li><a href="/wiki/1-Androstenedione" title="1-Androstenedione">1-Androstenedione</a></li> <li><a href="/wiki/1-Androsterone" title="1-Androsterone">1-Androsterone (1-andro, 1-DHEA)</a></li> <li><a href="/wiki/1-Testosterone" title="1-Testosterone">1-Testosterone</a></li> <li><a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/wiki/5%CE%B1-Androst-2-en-17-one" class="mw-redirect" title="5α-Androst-2-en-17-one">5α-Androst-2-en-17-one</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/11-Ketodihydrotestosterone" title="11-Ketodihydrotestosterone">11-Ketodihydrotestosterone</a></li> <li><a href="/wiki/Androsterone" title="Androsterone">Androsterone</a></li> <li><a href="/wiki/Bolazine" title="Bolazine">Bolazine</a> <ul><li><a href="/wiki/Bolazine_capronate" title="Bolazine capronate">Bolazine capronate</a></li></ul></li> <li><a href="/w/index.php?title=Dihydroethyltestosterone&action=edit&redlink=1" class="new" title="Dihydroethyltestosterone (page does not exist)">Dihydroethyltestosterone</a></li> <li><a href="/wiki/Dihydrofluoxymesterone" title="Dihydrofluoxymesterone">Dihydrofluoxymesterone</a></li> <li><a href="/w/index.php?title=Dihydromethylandrostenediol&action=edit&redlink=1" class="new" title="Dihydromethylandrostenediol (page does not exist)">Dihydromethylandrostenediol</a></li> <li><a href="/wiki/Dihydrotestosterone" title="Dihydrotestosterone">Dihydrotestosterone (DHT)</a> (<a href="/wiki/Androstanolone" title="Androstanolone">androstanolone, stanolone</a>) <ul><li><a href="/wiki/List_of_androgen_esters#Dihydrotestosterone_esters" title="List of androgen esters">Dihydrotestosterone esters</a></li></ul></li> <li><a href="/wiki/Drostanolone" title="Drostanolone">Drostanolone</a> <ul><li><a href="/wiki/Drostanolone_propionate" title="Drostanolone propionate">Drostanolone propionate</a></li></ul></li> <li><a href="/wiki/Epiandrosterone" title="Epiandrosterone">Epiandrosterone</a></li> <li><a href="/wiki/Epitiostanol" title="Epitiostanol">Epitiostanol</a></li> <li><a href="/wiki/Mepitiostane" title="Mepitiostane">Mepitiostane</a></li> <li><a href="/wiki/Mesabolone" title="Mesabolone">Mesabolone</a></li> <li><a href="/wiki/Mesterolone" title="Mesterolone">Mesterolone</a> <ul><li><a href="/wiki/Mesterolone_cipionate" title="Mesterolone cipionate">Mesterolone cipionate</a></li></ul></li> <li><a href="/wiki/Methyldiazinol" title="Methyldiazinol">Methyldiazinol</a></li> <li><a href="/wiki/Nisterime" title="Nisterime">Nisterime</a> <ul><li><a href="/wiki/Nisterime_acetate" title="Nisterime acetate">Nisterime acetate</a></li></ul></li> <li><a href="/wiki/Prostanozol" title="Prostanozol">Prostanozol</a></li> <li><a href="/wiki/Stenbolone" title="Stenbolone">Stenbolone</a> <ul><li><a href="/wiki/Stenbolone_acetate" title="Stenbolone acetate">Stenbolone acetate</a></li></ul></li> <li><a href="/wiki/Testifenon" title="Testifenon">Testifenon (testiphenon, testiphenone)</a></li></ul> <ul><li><i>19-Nortestosterone derivatives:</i> <a href="/wiki/7%CE%B1-Methyl-19-norandrostenedione" title="7α-Methyl-19-norandrostenedione">7α-Methyl-19-norandrostenedione (MENT dione, trestione)</a></li> <li><a href="/wiki/11%CE%B2-Methyl-19-nortestosterone" title="11β-Methyl-19-nortestosterone">11β-Methyl-19-nortestosterone</a> <ul><li><a href="/wiki/11%CE%B2-Methyl-19-nortestosterone_dodecylcarbonate" title="11β-Methyl-19-nortestosterone dodecylcarbonate">11β-Methyl-19-nortestosterone dodecylcarbonate</a></li></ul></li> <li><a href="/wiki/19-Nor-5-androstenediol" title="19-Nor-5-androstenediol">19-Nor-5-androstenediol</a></li> <li><a href="/wiki/19-Nor-5-androstenedione" title="19-Nor-5-androstenedione">19-Nor-5-androstenedione</a></li> <li><a href="/wiki/19-Nordehydroepiandrosterone" title="19-Nordehydroepiandrosterone">19-Nordehydroepiandrosterone</a></li> <li><a href="/wiki/Bolandiol" title="Bolandiol">Bolandiol</a> <ul><li><a href="/wiki/Bolandiol_dipropionate" title="Bolandiol dipropionate">Bolandiol dipropionate</a></li></ul></li> <li><a href="/wiki/Bolandione" title="Bolandione">Bolandione (19-nor-4-androstenedione)</a></li> <li><a href="/wiki/Bolmantalate" title="Bolmantalate">Bolmantalate (nandrolone adamantoate)</a></li> <li><a href="/wiki/Dienedione" title="Dienedione">Dienedione</a></li> <li><a href="/wiki/Dienolone" title="Dienolone">Dienolone</a></li> <li><a href="/wiki/Dimethandrolone" title="Dimethandrolone">Dimethandrolone</a> <ul><li><a href="/wiki/Dimethandrolone_buciclate" title="Dimethandrolone buciclate">Dimethandrolone buciclate</a></li> <li><a href="/wiki/Dimethandrolone_dodecylcarbonate" title="Dimethandrolone dodecylcarbonate">Dimethandrolone dodecylcarbonate</a></li> <li><a href="/wiki/Dimethandrolone_undecanoate" title="Dimethandrolone undecanoate">Dimethandrolone undecanoate</a></li></ul></li> <li><a href="/wiki/LS-1727" title="LS-1727">LS-1727 (nandrolone 17β-<i>N</i>-(2-chloroethyl)-<i>N</i>-nitrosocarbamate)</a></li> <li><a href="/wiki/Methoxydienone" title="Methoxydienone">Methoxydienone (methoxygonadiene)</a></li> <li><a href="/wiki/Nandrolone" title="Nandrolone">Nandrolone</a> <ul><li><a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">Nandrolone esters</a></li></ul></li> <li><a href="/wiki/Norclostebol" title="Norclostebol">Norclostebol</a> <ul><li><a href="/wiki/Norclostebol_acetate" title="Norclostebol acetate">Norclostebol acetate</a></li></ul></li> <li><a href="/wiki/Normethandrone" title="Normethandrone">Normethandrone (methylestrenolone, normethisterone)</a></li> <li><a href="/wiki/Oxabolone" title="Oxabolone">Oxabolone</a> <ul><li><a href="/wiki/Oxabolone_cipionate" title="Oxabolone cipionate">Oxabolone cipionate (oxabolone cypionate)</a></li></ul></li> <li><a href="/wiki/Trenbolone" title="Trenbolone">Trenbolone</a> <ul><li><a href="/wiki/Trenbolone_acetate" title="Trenbolone acetate">Trenbolone acetate</a></li> <li><a href="/wiki/Trenbolone_enanthate" title="Trenbolone enanthate">Trenbolone enanthate</a></li> <li><a href="/wiki/Trenbolone_hexahydrobenzylcarbonate" title="Trenbolone hexahydrobenzylcarbonate">Trenbolone hexahydrobenzylcarbonate</a></li> <li><a href="/wiki/Trenbolone_undecanoate" title="Trenbolone undecanoate">Trenbolone undecanoate</a></li></ul></li> <li><a href="/wiki/Trendione" title="Trendione">Trendione</a></li> <li><a href="/wiki/Trestolone" title="Trestolone">Trestolone (MENT)</a> <ul><li><a href="/wiki/Trestolone_acetate" title="Trestolone acetate">Trestolone acetate</a></li> <li><a href="/wiki/Trestolone_enanthate" title="Trestolone enanthate">Trestolone enanthate</a></li></ul></li></ul> <ul><li><i>5α-Dihydro-19-nortestosterone derivatives:</i> <a href="/wiki/5%CE%B1-Dihydronandrolone" title="5α-Dihydronandrolone">5α-Dihydronandrolone</a></li> <li><a href="/w/index.php?title=5%CE%B1-Dihydrotrestolone&action=edit&redlink=1" class="new" title="5α-Dihydrotrestolone (page does not exist)">5α-Dihydrotrestolone</a></li> <li><a href="/wiki/19-Norandrosterone" title="19-Norandrosterone">19-Norandrosterone</a></li></ul> <ul><li><i>17α-Alkylated testosterone derivatives:</i> <a href="/wiki/Bolasterone" title="Bolasterone">Bolasterone</a></li> <li><a href="/wiki/Calusterone" title="Calusterone">Calusterone</a></li> <li><a href="/wiki/Chlorodehydromethylandrostenediol" title="Chlorodehydromethylandrostenediol">Chlorodehydromethylandrostenediol (CDMA)</a></li> <li><a href="/wiki/Chlorodehydromethyltestosterone" title="Chlorodehydromethyltestosterone">Chlorodehydromethyltestosterone (CDMT)</a></li> <li><a href="/wiki/Chloromethylandrostenediol" title="Chloromethylandrostenediol">Chloromethylandrostenediol (CMA)</a></li> <li><a href="/wiki/Enestebol" title="Enestebol">Enestebol</a></li> <li><a href="/wiki/Ethyltestosterone" title="Ethyltestosterone">Ethyltestosterone</a></li> <li><a href="/wiki/Fluoxymesterone" title="Fluoxymesterone">Fluoxymesterone</a></li> <li><a href="/wiki/Formebolone" title="Formebolone">Formebolone</a></li> <li><a href="/wiki/Hydroxystenozole" title="Hydroxystenozole">Hydroxystenozole</a></li> <li><a href="/wiki/Metandienone" title="Metandienone">Metandienone (methandrostenolone)</a></li> <li><a href="/wiki/Methandriol" title="Methandriol">Methandriol (methylandrostenediol)</a> <ul><li><a href="/wiki/Methandriol_bisenanthoyl_acetate" title="Methandriol bisenanthoyl acetate">Methandriol bisenanthoyl acetate</a></li> <li><a href="/wiki/Methandriol_diacetate" title="Methandriol diacetate">Methandriol diacetate</a></li> <li><a href="/wiki/Methandriol_dipropionate" title="Methandriol dipropionate">Methandriol dipropionate</a></li> <li><a href="/wiki/Methandriol_propionate" title="Methandriol propionate">Methandriol propionate</a></li></ul></li> <li><a href="/wiki/Methylclostebol" title="Methylclostebol">Methylclostebol (chloromethyltestosterone)</a></li> <li><a href="/wiki/Methyltestosterone" title="Methyltestosterone">Methyltestosterone</a> (<a href="/wiki/Esterified_estrogens/methyltestosterone" title="Esterified estrogens/methyltestosterone">+esterified estrogens</a>) <ul><li><a href="/wiki/Methyltestosterone_3-hexyl_ether" title="Methyltestosterone 3-hexyl ether">Methyltestosterone 3-hexyl ether</a></li></ul></li> <li><a href="/wiki/Oxymesterone" title="Oxymesterone">Oxymesterone</a></li> <li><a href="/wiki/Penmesterol" title="Penmesterol">Penmesterol</a></li> <li><a href="/wiki/Tiomesterone" title="Tiomesterone">Tiomesterone</a></li></ul> <ul><li><i>17α-Alkylated 5α-dihydrotestosterone derivatives:</i> <a href="/wiki/Androisoxazole" title="Androisoxazole">Androisoxazole</a></li> <li><a href="/wiki/Desoxymethyltestosterone" title="Desoxymethyltestosterone">Desoxymethyltestosterone</a></li> <li><a href="/wiki/Furazabol" title="Furazabol">Furazabol</a></li> <li><a href="/wiki/Mebolazine" title="Mebolazine">Mebolazine (dimethazine)</a></li> <li><a href="/wiki/Mestanolone" title="Mestanolone">Mestanolone</a></li> <li><a href="/wiki/Metenolone" title="Metenolone">Metenolone</a> <ul><li><a href="/wiki/Metenolone_acetate" title="Metenolone acetate">Metenolone acetate</a></li> <li><a href="/wiki/Metenolone_enanthate" title="Metenolone enanthate">Metenolone enanthate</a></li></ul></li> <li><a href="/wiki/Methasterone" title="Methasterone">Methasterone</a></li> <li><a href="/wiki/Methyl-1-testosterone" title="Methyl-1-testosterone">Methyl-1-testosterone</a></li> <li><a href="/wiki/Methylepitiostanol" title="Methylepitiostanol">Methylepitiostanol</a></li> <li><a href="/wiki/Methylstenbolone" title="Methylstenbolone">Methylstenbolone</a></li> <li><a href="/wiki/Oxandrolone" title="Oxandrolone">Oxandrolone</a></li> <li><a href="/wiki/Oxymetholone" title="Oxymetholone">Oxymetholone</a></li> <li><a href="/wiki/Stanozolol" title="Stanozolol">Stanozolol</a></li></ul> <ul><li><i>17α-Alkylated 19-nortestosterone derivatives:</i> <a href="/wiki/Bolenol" title="Bolenol">Bolenol</a></li> <li><a href="/wiki/Dimethyldienolone" title="Dimethyldienolone">Dimethyldienolone</a></li> <li><a href="/wiki/Dimethyltrienolone" title="Dimethyltrienolone">Dimethyltrienolone</a></li> <li><a href="/wiki/Ethyldienolone" title="Ethyldienolone">Ethyldienolone</a></li> <li><a href="/wiki/Ethylestrenol" title="Ethylestrenol">Ethylestrenol</a></li> <li><a href="/wiki/Methyldienolone" title="Methyldienolone">Methyldienolone</a></li> <li><a href="/wiki/Methylhydroxynandrolone" title="Methylhydroxynandrolone">Methylhydroxynandrolone (MOHN, MHN)</a></li> <li><a href="/wiki/Metribolone" title="Metribolone">Metribolone</a></li> <li><a href="/wiki/Mibolerone" title="Mibolerone">Mibolerone</a></li> <li><a href="/wiki/Norboletone" title="Norboletone">Norboletone</a></li> <li><a href="/wiki/Norethandrolone" title="Norethandrolone">Norethandrolone</a></li> <li><a href="/wiki/Propetandrol" title="Propetandrol">Propetandrol</a></li> <li><a href="/wiki/RU-2309" title="RU-2309">RU-2309</a></li> <li><a href="/wiki/Tetrahydrogestrinone" title="Tetrahydrogestrinone">Tetrahydrogestrinone</a></li></ul> <ul><li><i>17α-Alkylated 5α-dihydro-19-nortestosterone derivatives:</i> <a href="/wiki/5%CE%B1-Dihydronorethandrolone" title="5α-Dihydronorethandrolone">5α-Dihydronorethandrolone</a></li> <li><a href="/wiki/5%CE%B1-Dihydronormethandrone" title="5α-Dihydronormethandrone">5α-Dihydronormethandrone</a></li></ul> <ul><li><i>17α-Vinyltestosterone derivatives:</i> <a href="/wiki/Norvinisterone" title="Norvinisterone">Norvinisterone (vinylnortestosterone)</a></li></ul> <ul><li><i>17α-Vinyl-19-nortestosterone derivatives:</i> <a href="/wiki/Vinyltestosterone" title="Vinyltestosterone">Vinyltestosterone</a></li></ul> <ul><li><i>17α-Ethynyltestosterone derivatives:</i> <a href="/wiki/Danazol" title="Danazol">Danazol</a></li> <li><a href="/wiki/Ethinylandrostenediol" title="Ethinylandrostenediol">Ethinylandrostenediol</a> <ul><li><a href="/wiki/Ethandrostate" title="Ethandrostate">Ethandrostate</a></li></ul></li> <li><a href="/wiki/Ethisterone" title="Ethisterone">Ethisterone (ethynyltestosterone)</a></li></ul> <ul><li><i>5α-Dihydro-17α-ethynyltestosterone derivatives:</i> <a href="/wiki/17%CE%B1-Ethynyl-3%CE%B1-androstanediol" title="17α-Ethynyl-3α-androstanediol">17α-Ethynyl-3α-androstanediol</a></li> <li><a href="/wiki/17%CE%B1-Ethynyl-3%CE%B2-androstanediol" title="17α-Ethynyl-3β-androstanediol">17α-Ethynyl-3β-androstanediol</a></li> <li><a href="/wiki/Dihydroethisterone" class="mw-redirect" title="Dihydroethisterone">Dihydroethisterone</a></li></ul> <ul><li><i>17α-Ethynyl-19-nortestosterone derivatives:</i> <a href="/wiki/%CE%944-Tibolone" title="Δ4-Tibolone">Δ<sup>4</sup>-Tibolone</a></li> <li><a href="/wiki/Desogestrel" title="Desogestrel">Desogestrel</a></li> <li><a href="/wiki/Etonogestrel" title="Etonogestrel">Etonogestrel</a></li> <li><a href="/wiki/Etynodiol" title="Etynodiol">Etynodiol</a> <ul><li><a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">Etynodiol diacetate</a></li></ul></li> <li><a href="/wiki/Gestodene" title="Gestodene">Gestodene</a></li> <li><a href="/wiki/Gestrinone" title="Gestrinone">Gestrinone</a></li> <li><a href="/wiki/Levonorgestrel" title="Levonorgestrel">Levonorgestrel</a></li> <li><a href="/wiki/Levonorgestrel_ester" class="mw-redirect" title="Levonorgestrel ester">Levonorgestrel esters</a> (e.g., <a href="/wiki/Levonorgestrel_butanoate" title="Levonorgestrel butanoate">levonorgestrel butanoate</a>)</li> <li><a href="/wiki/Lynestrenol" title="Lynestrenol">Lynestrenol</a> <ul><li><a href="/wiki/Lynestrenol_phenylpropionate" title="Lynestrenol phenylpropionate">Lynestrenol phenylpropionate</a></li></ul></li> <li><a href="/wiki/Norethisterone" title="Norethisterone">Norethisterone</a></li> <li><a href="/wiki/Norethisterone_ester" class="mw-redirect" title="Norethisterone ester">Norethisterone esters</a> (e.g., <a href="/wiki/Norethisterone_acetate" title="Norethisterone acetate">norethisterone acetate</a>, <a href="/wiki/Norethisterone_enanthate" title="Norethisterone enanthate">norethisterone enanthate</a>)</li> <li><a href="/wiki/Norgestrel" title="Norgestrel">Norgestrel</a></li> <li><a href="/wiki/Norgestrienone" title="Norgestrienone">Norgestrienone</a></li> <li><a href="/wiki/Quingestanol" title="Quingestanol">Quingestanol</a> <ul><li><a href="/wiki/Quingestanol_acetate" title="Quingestanol acetate">Quingestanol acetate</a></li></ul></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li></ul> <ul><li><i>5α-Dihydro-17α-ethynyl-19-nortestosterone derivatives:</i> <a href="/wiki/5%CE%B1-Dihydrolevonorgestrel" title="5α-Dihydrolevonorgestrel">5α-Dihydrolevonorgestrel</a></li> <li><a href="/wiki/5%CE%B1-Dihydronorethisterone" title="5α-Dihydronorethisterone">5α-Dihydronorethisterone</a></li></ul> <ul><li><i>Progesterone derivatives:</i> <a href="/wiki/6%CE%B1-Methylprogesterone" title="6α-Methylprogesterone">6α-Methylprogesterone</a></li> <li><a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">Medroxyprogesterone acetate</a></li> <li><a href="/wiki/Megestrol_acetate" title="Megestrol acetate">Megestrol acetate</a></li></ul> <ul><li><i>Others/unsorted:</i> <a href="/wiki/3-Keto-5%CE%B1-abiraterone" title="3-Keto-5α-abiraterone">3-Keto-5α-abiraterone</a></li> <li><a href="/wiki/5%CE%B1-Androstane" class="mw-redirect" title="5α-Androstane">5α-Androstane</a></li> <li><a href="/wiki/Alternariol" title="Alternariol">Alternariol</a></li> <li><a href="/wiki/Cl-4AS-1" title="Cl-4AS-1">Cl-4AS-1</a></li> <li><a href="/wiki/Drupanol" title="Drupanol">Drupanol</a></li> <li><a href="/wiki/Trilostane" title="Trilostane">Trilostane</a></li> <li><a href="/wiki/ZM-182345" title="ZM-182345">ZM-182345</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center"><a href="/wiki/Selective_androgen_receptor_modulator" title="Selective androgen receptor modulator"><abbr title="Selective androgen receptor modulator">SARMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Selective androgen receptor modulator</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Nonsteroidal:</i> <a href="/w/index.php?title=198RL26&action=edit&redlink=1" class="new" title="198RL26 (page does not exist)">198RL26</a></li> <li><a href="/wiki/ACP-105" title="ACP-105">ACP-105</a></li> <li><a href="/wiki/AC-262,536" title="AC-262,536">AC-262,536</a></li> <li><a href="/wiki/Acetothiolutamide" title="Acetothiolutamide">Acetothiolutamide</a></li> <li><a href="/wiki/Acetoxolutamide" title="Acetoxolutamide">Acetoxolutamide</a></li> <li><a href="/wiki/Andarine" title="Andarine">Andarine (acetamidoxolutamide, androxolutamide, GTx-007, S-4)</a></li> <li><a href="/wiki/BMS-564,929" title="BMS-564,929">BMS-564,929</a></li> <li><a href="/w/index.php?title=DTIB&action=edit&redlink=1" class="new" title="DTIB (page does not exist)">DTIB</a></li> <li><a href="/wiki/Enobosarm" title="Enobosarm">Enobosarm (ostarine, MK-2866, GTx-024, S-22)</a></li> <li><a href="/w/index.php?title=FTBU-1&action=edit&redlink=1" class="new" title="FTBU-1 (page does not exist)">FTBU-1</a></li> <li><a href="/wiki/GLPG-0492" title="GLPG-0492">GLPG-0492</a></li> <li><a href="/wiki/GSK2881078" title="GSK2881078">GSK2881078</a></li> <li><a href="/wiki/GSK-4336A" title="GSK-4336A">GSK-4336A</a></li> <li><a href="/w/index.php?title=GSK-8698&action=edit&redlink=1" class="new" title="GSK-8698 (page does not exist)">GSK-8698</a></li> <li><a href="/wiki/LG121071" title="LG121071">LG121071 (LGD-121071)</a></li> <li><a href="/wiki/LGD-2226" title="LGD-2226">LGD-2226</a></li> <li><a href="/wiki/LGD-2941" title="LGD-2941">LGD-2941 (LGD-122941)</a></li> <li><a href="/wiki/LGD-3303" title="LGD-3303">LGD-3303</a></li> <li><a href="/wiki/LGD-4033" class="mw-redirect" title="LGD-4033">LGD-4033</a></li> <li><a href="/wiki/LY305" title="LY305">LY305</a></li> <li><a href="/wiki/JNJ-26146900" title="JNJ-26146900">JNJ-26146900</a></li> <li><a href="/wiki/JNJ-28330835" title="JNJ-28330835">JNJ-28330835</a></li> <li><a href="/wiki/JNJ-37654032" title="JNJ-37654032">JNJ-37654032</a></li> <li><a href="/wiki/OPK-88004" title="OPK-88004">OPK-88004 (LY-2452473, TT-701)</a></li> <li><a href="/w/index.php?title=ORM-11984&action=edit&redlink=1" class="new" title="ORM-11984 (page does not exist)">ORM-11984</a></li> <li><a href="/wiki/PF-06260414" title="PF-06260414">PF-06260414</a></li> <li><a href="/w/index.php?title=R-1_(drug)&action=edit&redlink=1" class="new" title="R-1 (drug) (page does not exist)">R-1</a></li> <li><a href="/wiki/RU-59063" title="RU-59063">RU-59063</a></li> <li><a href="/w/index.php?title=S-1_(drug)&action=edit&redlink=1" class="new" title="S-1 (drug) (page does not exist)">S-1</a></li> <li><a href="/wiki/S-23_(drug)" title="S-23 (drug)">S-23</a></li> <li><a href="/wiki/S-40503" title="S-40503">S-40503</a></li> <li><a href="/w/index.php?title=S-101479&action=edit&redlink=1" class="new" title="S-101479 (page does not exist)">S-101479</a></li> <li><a href="/wiki/Vosilasarm" title="Vosilasarm">Vosilasarm</a></li></ul> <ul><li><i>Steroidal:</i> <a href="/w/index.php?title=EM-9017&action=edit&redlink=1" class="new" title="EM-9017 (page does not exist)">EM-9017</a></li> <li><a href="/wiki/MK-0773" title="MK-0773">MK-0773</a></li> <li><a href="/wiki/TFM-4AS-1" title="TFM-4AS-1">TFM-4AS-1</a></li> <li><a href="/wiki/YK-11" title="YK-11">YK-11</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Steroidal:</i> <a href="/wiki/7%CE%B1-Thioprogesterone" title="7α-Thioprogesterone">7α-Thioprogesterone</a></li> <li><a href="/wiki/7%CE%B1-Thiospironolactone" title="7α-Thiospironolactone">7α-Thiospironolactone</a></li> <li><a href="/wiki/7%CE%B1-Thiomethylspironolactone" title="7α-Thiomethylspironolactone">7α-Thiomethylspironolactone</a></li> <li><a href="/wiki/11%CE%B1-Hydroxyprogesterone" title="11α-Hydroxyprogesterone">11α-Hydroxyprogesterone</a></li> <li><a href="/wiki/15%CE%B2-Hydroxycyproterone_acetate" title="15β-Hydroxycyproterone acetate">15β-Hydroxycyproterone acetate</a></li> <li><a href="/wiki/Abiraterone" class="mw-redirect" title="Abiraterone">Abiraterone</a></li> <li><a href="/wiki/Abiraterone_acetate" title="Abiraterone acetate">Abiraterone acetate</a></li> <li><a href="/wiki/Allyltestosterone" title="Allyltestosterone">Allyltestosterone</a></li> <li><a href="/wiki/Benorterone" title="Benorterone">Benorterone</a></li> <li><a class="mw-selflink selflink">BOMT</a></li> <li><a href="/wiki/Canrenoic_acid" title="Canrenoic acid">Canrenoic acid</a></li> <li><a href="/wiki/Canrenone" title="Canrenone">Canrenone</a></li> <li><a href="/wiki/Chlormadinone_acetate" title="Chlormadinone acetate">Chlormadinone acetate</a></li> <li><a href="/wiki/Clascoterone" title="Clascoterone">Clascoterone</a></li> <li><a href="/wiki/Clometerone" title="Clometerone">Clometerone</a></li> <li><a href="/wiki/Cyproheptadine" title="Cyproheptadine">Cyproheptadine</a></li> <li><a href="/wiki/Cyproterone" title="Cyproterone">Cyproterone</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Delanterone" title="Delanterone">Delanterone</a></li> <li><a href="/wiki/Delmadinone_acetate" title="Delmadinone acetate">Delmadinone acetate</a></li> <li><a href="/wiki/Dicirenone" title="Dicirenone">Dicirenone</a></li> <li><a href="/wiki/Dienogest" title="Dienogest">Dienogest</a></li> <li><a href="/wiki/Drospirenone" title="Drospirenone">Drospirenone</a></li> <li><a href="/wiki/DU-41165" title="DU-41165">DU-41165</a></li> <li><a href="/wiki/Edogestrone" title="Edogestrone">Edogestrone</a></li> <li><a href="/w/index.php?title=EM-4350&action=edit&redlink=1" class="new" title="EM-4350 (page does not exist)">EM-4350</a></li> <li><a href="/wiki/EM-5854" title="EM-5854">EM-5854</a></li> <li><a href="/w/index.php?title=EM-5855&action=edit&redlink=1" class="new" title="EM-5855 (page does not exist)">EM-5855</a></li> <li><a href="/w/index.php?title=EM-6537&action=edit&redlink=1" class="new" title="EM-6537 (page does not exist)">EM-6537</a></li> <li><a href="/wiki/Epitestosterone" title="Epitestosterone">Epitestosterone</a></li> <li><a href="/wiki/Galeterone" title="Galeterone">Galeterone</a></li> <li><a href="/wiki/Guggulsterone" title="Guggulsterone">Guggulsterone</a></li> <li><a href="/w/index.php?title=Ludaterone&action=edit&redlink=1" class="new" title="Ludaterone (page does not exist)">Ludaterone</a></li> <li><a href="/wiki/Medrogestone" title="Medrogestone">Medrogestone</a></li> <li><a href="/wiki/Megestrol_acetate" title="Megestrol acetate">Megestrol acetate</a></li> <li><a href="/wiki/Mespirenone" title="Mespirenone">Mespirenone</a></li> <li><a href="/wiki/Metogest" title="Metogest">Metogest</a></li> <li><a href="/wiki/Mexrenone" title="Mexrenone">Mexrenone</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li> <li><a href="/wiki/Nomegestrol_acetate" title="Nomegestrol acetate">Nomegestrol acetate</a></li> <li><a href="/wiki/Nordinone" title="Nordinone">Nordinone</a></li> <li><a href="/wiki/Osaterone" title="Osaterone">Osaterone</a></li> <li><a href="/wiki/Osaterone_acetate" title="Osaterone acetate">Osaterone acetate</a></li> <li><a href="/wiki/Oxendolone" title="Oxendolone">Oxendolone</a></li> <li><a href="/wiki/Potassium_canrenoate" title="Potassium canrenoate">Potassium canrenoate</a></li> <li><a href="/wiki/Promegestone" title="Promegestone">Promegestone</a></li> <li><a href="/wiki/Prorenone" title="Prorenone">Prorenone</a></li> <li><a href="/wiki/Rosterolone" title="Rosterolone">Rosterolone</a></li> <li><a href="/w/index.php?title=RU-15328&action=edit&redlink=1" class="new" title="RU-15328 (page does not exist)">RU-15328</a></li> <li><a href="/wiki/SC-5233" title="SC-5233">SC-5233 (spirolactone)</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/wiki/Spirorenone" title="Spirorenone">Spirorenone</a></li> <li><a href="/wiki/Spiroxasone" title="Spiroxasone">Spiroxasone</a></li> <li><a href="/wiki/Topterone" title="Topterone">Topterone</a></li> <li><a href="/wiki/Trimegestone" title="Trimegestone">Trimegestone</a></li> <li><a href="/wiki/Trimethyltrienolone" title="Trimethyltrienolone">Trimethyltrienolone (R-2956)</a></li> <li><a href="/wiki/Zanoterone" title="Zanoterone">Zanoterone</a></li></ul> <ul><li><i>Nonsteroidal:</i> <a href="/wiki/5N-Bicalutamide" title="5N-Bicalutamide">5<i>N</i>-Bicalutamide</a></li> <li><a href="/wiki/AA560" title="AA560">AA560</a></li> <li><a href="/w/index.php?title=Antarlide&action=edit&redlink=1" class="new" title="Antarlide (page does not exist)">Antarlides</a></li> <li><a href="/w/index.php?title=Arabilin&action=edit&redlink=1" class="new" title="Arabilin (page does not exist)">Arabilin</a></li> <li><a href="/wiki/Apalutamide" title="Apalutamide">Apalutamide</a></li> <li><a href="/wiki/Atraric_acid" title="Atraric acid">Atraric acid</a></li> <li><a href="/w/index.php?title=AZD-3514&action=edit&redlink=1" class="new" title="AZD-3514 (page does not exist)">AZD-3514</a></li> <li><a href="/wiki/Bakuchiol" title="Bakuchiol">Bakuchiol</a></li> <li><a href="/wiki/Bavdegalutamide" title="Bavdegalutamide">Bavdegalutamide</a></li> <li><a href="/w/index.php?title=BAY-1024767&action=edit&redlink=1" class="new" title="BAY-1024767 (page does not exist)">BAY-1024767</a></li> <li><a href="/wiki/Bicalutamide" title="Bicalutamide">Bicalutamide</a></li> <li><a href="/wiki/Bisphenol" title="Bisphenol">Bisphenols</a> (e.g., <a href="/wiki/Bisphenol_A_diglycidyl_ether" title="Bisphenol A diglycidyl ether">BADGE</a>, <a href="/w/index.php?title=Bisphenol_F_diglycidyl_ether&action=edit&redlink=1" class="new" title="Bisphenol F diglycidyl ether (page does not exist)">BFDGE</a>, <a href="/wiki/Bisphenol_A" title="Bisphenol A">bisphenol A</a>, <a href="/wiki/Bisphenol_F" title="Bisphenol F">bisphenol F</a>, <a href="/wiki/Bisphenol_S" title="Bisphenol S">bisphenol S</a>)</li> <li><a href="/w/index.php?title=BMS-501949&action=edit&redlink=1" class="new" title="BMS-501949 (page does not exist)">BMS-501949</a></li> <li><a href="/w/index.php?title=BMS-570511&action=edit&redlink=1" class="new" title="BMS-570511 (page does not exist)">BMS-570511</a></li> <li><a href="/wiki/BMS-641988" title="BMS-641988">BMS-641988</a></li> <li><a href="/w/index.php?title=CH5137291&action=edit&redlink=1" class="new" title="CH5137291 (page does not exist)">CH5137291</a></li> <li><a href="/wiki/Cimetidine" title="Cimetidine">Cimetidine</a></li> <li><a href="/wiki/Cioteronel" title="Cioteronel">Cioteronel</a></li> <li><a href="/wiki/Cyanonilutamide" title="Cyanonilutamide">Cyanonilutamide</a></li> <li><a href="/wiki/Darolutamide" title="Darolutamide">Darolutamide</a></li> <li><a href="/wiki/DDT" title="DDT">DDT</a> (via metabolite <a href="/wiki/Dichlorodiphenyldichloroethylene" title="Dichlorodiphenyldichloroethylene">p,p’-DDE</a>)</li> <li><a href="/wiki/Dieldrin" title="Dieldrin">Dieldrin</a></li> <li><a href="/wiki/DIMP_(antiandrogen)" title="DIMP (antiandrogen)">DIMP</a></li> <li><a href="/wiki/Endosulfan" title="Endosulfan">Endosulfan</a></li> <li><a href="/wiki/Enzalutamide" title="Enzalutamide">Enzalutamide</a></li> <li><a href="/wiki/EPI-001" title="EPI-001">EPI-001</a></li> <li><a href="/wiki/Fenarimol" title="Fenarimol">Fenarimol</a></li> <li><a href="/wiki/Flutamide" title="Flutamide">Flutamide</a></li> <li><a href="/wiki/Hydroxyflutamide" title="Hydroxyflutamide">Hydroxyflutamide</a></li> <li><a href="/wiki/Inocoterone" title="Inocoterone">Inocoterone</a></li> <li><a href="/wiki/Inocoterone_acetate" title="Inocoterone acetate">Inocoterone acetate</a></li> <li><a href="/wiki/Ketoconazole" title="Ketoconazole">Ketoconazole</a></li> <li><a href="/wiki/Ketodarolutamide" title="Ketodarolutamide">Ketodarolutamide</a></li> <li><a href="/wiki/Lavender_oil" title="Lavender oil">Lavender oil</a></li> <li><a href="/w/index.php?title=LG-105&action=edit&redlink=1" class="new" title="LG-105 (page does not exist)">LG-105</a></li> <li><a href="/wiki/LG-120907" title="LG-120907">LG-120907</a></li> <li><a href="/w/index.php?title=LGD-1331&action=edit&redlink=1" class="new" title="LGD-1331 (page does not exist)">LGD-1331</a></li> <li><a href="/wiki/Linuron" title="Linuron">Linuron</a></li> <li><a href="/wiki/Masofaniten" title="Masofaniten">Masofaniten</a></li> <li><a href="/wiki/Methiocarb" title="Methiocarb">Methiocarb</a></li> <li><a href="/w/index.php?title=N-Butylbenzenesulfonamide&action=edit&redlink=1" class="new" title="N-Butylbenzenesulfonamide (page does not exist)"><i>N</i>-Butylbenzenesulfonamide</a></li> <li><a href="/wiki/N-Desmethylapalutamide" title="N-Desmethylapalutamide"><i>N</i>-Desmethylapalutamide</a></li> <li><a href="/wiki/N-Desmethylenzalutamide" title="N-Desmethylenzalutamide"><i>N</i>-Desmethylenzalutamide</a></li> <li><a href="/wiki/Nilutamide" title="Nilutamide">Nilutamide</a></li> <li><a href="/w/index.php?title=ONC1-13B&action=edit&redlink=1" class="new" title="ONC1-13B (page does not exist)">ONC1-13B</a></li> <li><a href="/wiki/Pentomone" title="Pentomone">Pentomone</a></li> <li><a href="/w/index.php?title=PF-998425&action=edit&redlink=1" class="new" title="PF-998425 (page does not exist)">PF-998425</a></li> <li><a href="/wiki/Phenothrin" title="Phenothrin">Phenothrin</a></li> <li><a href="/wiki/Prochloraz" title="Prochloraz">Prochloraz</a></li> <li><a href="/wiki/Procymidone" title="Procymidone">Procymidone</a></li> <li><a href="/wiki/Proxalutamide" title="Proxalutamide">Proxalutamide</a></li> <li><a href="/wiki/Pyrilutamide" title="Pyrilutamide">Pyrilutamide</a></li> <li><a href="/wiki/Ralaniten" title="Ralaniten">Ralaniten (EPI-002)</a></li> <li><a href="/wiki/Ralaniten_acetate" title="Ralaniten acetate">Ralaniten acetate (EPI-506)</a></li> <li><a href="/wiki/RD-162" title="RD-162">RD-162</a></li> <li><a href="/wiki/Rezvilutamide" title="Rezvilutamide">Rezvilutamide</a></li> <li><a href="/w/index.php?title=Ro_2-7239&action=edit&redlink=1" class="new" title="Ro 2-7239 (page does not exist)">Ro 2-7239</a></li> <li><a href="/w/index.php?title=Ro_5-2537&action=edit&redlink=1" class="new" title="Ro 5-2537 (page does not exist)">Ro 5-2537</a></li> <li><a href="/wiki/RU-22930" title="RU-22930">RU-22930</a></li> <li><a href="/wiki/RU-56187" title="RU-56187">RU-56187</a></li> <li><a href="/wiki/RU-57073" title="RU-57073">RU-57073</a></li> <li><a href="/wiki/RU-58642" title="RU-58642">RU-58642</a></li> <li><a href="/wiki/RU-58841" title="RU-58841">RU-58841</a></li> <li><a href="/wiki/Seviteronel" title="Seviteronel">Seviteronel</a></li> <li><a href="/wiki/Thalidomide" title="Thalidomide">Thalidomide</a></li> <li><a href="/wiki/Topilutamide" title="Topilutamide">Topilutamide (fluridil)</a></li> <li><a href="/wiki/Valproic_acid" class="mw-redirect" title="Valproic acid">Valproic acid</a></li> <li><a href="/wiki/Vinclozolin" title="Vinclozolin">Vinclozolin</a></li> <li><a href="/w/index.php?title=YM-580&action=edit&redlink=1" class="new" title="YM-580 (page does not exist)">YM-580</a></li> <li><a href="/w/index.php?title=YM-92088&action=edit&redlink=1" class="new" title="YM-92088 (page does not exist)">YM-92088</a></li> <li><a href="/w/index.php?title=YM-175735&action=edit&redlink=1" class="new" title="YM-175735 (page does not exist)">YM-175735</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/GPRC6A" title="GPRC6A">GPRC6A</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;">Agonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cation" class="mw-redirect" title="Cation">Cations</a> (incl. <a href="/wiki/Aluminium" title="Aluminium">aluminium</a>, <a href="/wiki/Calcium" title="Calcium">calcium</a>, <a href="/wiki/Gadolinium" title="Gadolinium">gadolinium</a>, <a href="/wiki/Magnesium" title="Magnesium">magnesium</a>, <a href="/wiki/Strontium" title="Strontium">strontium</a>, <a href="/wiki/Zinc" title="Zinc">zinc</a>)</li> <li><a href="/wiki/Dehydroandrosterone" title="Dehydroandrosterone">Dehydroandrosterone</a></li> <li><a href="/wiki/Dihydrotestosterone" title="Dihydrotestosterone">Dihydrotestosterone</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/wiki/Amino_acid" title="Amino acid"><small>L</small>-α-Amino acids</a> (incl. <a href="/wiki/Arginine" title="Arginine"><small>L</small>-arginine</a>, <a href="/wiki/Lysine" title="Lysine"><small>L</small>-lysine</a>, <a href="/wiki/Ornithine" title="Ornithine"><small>L</small>-ornithine</a>)</li> <li><a href="/wiki/Osteocalcin" title="Osteocalcin">Osteocalcin</a></li> <li><a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin"><abbr title="Sex hormone-binding globulin">SHBG</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Sex hormone-binding globulin</span></li> <li><a href="/wiki/Testosterone" title="Testosterone">Testosterone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Androgens_and_antiandrogens" title="Template:Androgens and antiandrogens">Androgens and antiandrogens</a></dd> <dd><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators">Estrogen receptor modulators</a></dd> <dd><a href="/wiki/Template:Progesterone_receptor_modulators" title="Template:Progesterone receptor modulators">Progesterone receptor modulators</a></dd> <dd><a href="/wiki/List_of_androgens_and_anabolic_steroids" title="List of androgens and anabolic steroids">List of androgens and anabolic steroids</a></dd></dl> </div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=BOMT&oldid=1219489445">https://en.wikipedia.org/w/index.php?title=BOMT&oldid=1219489445</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Drugs_not_assigned_an_ATC_code" title="Category:Drugs not assigned an ATC code">Drugs not assigned an ATC code</a></li><li><a href="/wiki/Category:Abandoned_drugs" title="Category:Abandoned drugs">Abandoned drugs</a></li><li><a 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