| dbo:abstract |
Zanoterone (INN, USAN) (former developmental code name WIN-49596), also known as (5α,17α)-1'-(methylsulfonyl)-1'-H-pregn-20-yno[3,2-c]pyrazol-17-ol, is a steroidal antiandrogen which was never marketed. It was investigated for the treatment of benign prostatic hyperplasia (BPH) but failed to demonstrate sufficient efficacy in phase II clinical trials, and also showed an unacceptable incidence rate and severity of side effects (e.g., breast pain and gynecomastia). As such, it was not further developed. Zanoterone was derived from 5α-dihydroethisterone (5α-dihydro-17α-ethynyltestosterone). It is an antagonist of the androgen receptor (Ki = 2.2 μM; RBA compared to metribolone = 2.2%), and with the exception of antiprogestogenic activity in rat and rabbit models, is devoid of other hormonal activities. Zanoterone does not inhibit 5α-reductase, aromatase, or 3α- or 3β-hydroxysteroid dehydrogenase in vitro. The drug significantly increases testosterone and estradiol levels in men. Zanoterone has been found to not significantly inhibit mating performance or fertility in adult male rats at high dosages for an extended period of time. It has been found to act as an inducer of the enzyme CYP3A4 in vivo in rats. (en) |
| dbo:casNumber |
107000-34-0 |
| dbo:chEMBL |
2079581 |
| dbo:class |
dbr:Steroidal_antiandrogen |
| dbo:drugbank |
D06357 |
| dbo:fdaUniiCode |
XQ5V1W49JG |
| dbo:kegg |
D06357 |
| dbo:pubchem |
9844827 |
| dbo:thumbnail |
wiki-commons:Special:FilePath/Zanoterone.svg?width=300 |
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dbr:5α-reductase dbr:Benign_prostatic_hyperplasia dbr:Enzyme_inducer dbr:Androgen_receptor dbc:Progonadotropins dbr:Antiprogestogen dbr:In_vitro dbr:In_vivo dbc:Abandoned_drugs dbc:Androstanes dbc:Steroidal_antiandrogens dbr:Oral_administration dbr:Enzyme dbr:Aromatase dbr:Clinical_trial dbr:Receptor_antagonist dbc:Antiprogestogens dbc:Pyrazoles dbr:Estradiol dbr:Breast_pain dbr:Gynecomastia dbr:Testosterone dbc:Sulfonamides dbr:CYP3A4 dbr:Metribolone dbr:Side_effect dbr:List_of_steroidal_antiandrogens dbr:Phases_of_clinical_research dbr:Steroidal_antiandrogen dbr:5α-dihydroethisterone dbr:3α-hydroxysteroid_dehydrogenase dbr:3β-hydroxysteroid_dehydrogenase |
| dbp:c |
23 (xsd:integer) |
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107000 (xsd:integer) |
| dbp:chembl |
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| dbp:class |
dbr:Steroidal_antiandrogen |
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D06357 (en) |
| dbp:h |
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| dbp:iupacName |
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| dbp:kegg |
D06357 (en) |
| dbp:n |
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| dbp:o |
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| dbp:pubchem |
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| dbp:routesOfAdministration |
dbr:Oral_administration |
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| dbp:smiles |
C[C@]12CC[C@H]3[C@H]CC[C@@H]4[C@@]3C (en) |
| dbp:stdinchi |
1 (xsd:integer) |
| dbp:stdinchikey |
MHDDZDPNIDVLNK-ZGIWMXSJSA-N (en) |
| dbp:synonyms |
WIN-49596; -1'--1'-H-pregn-20-yno[3,2-c]pyrazol-17-ol (en) |
| dbp:unii |
XQ5V1W49JG (en) |
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250 (xsd:integer) |
| dbp:wikiPageUsesTemplate |
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| dcterms:subject |
dbc:Progonadotropins dbc:Abandoned_drugs dbc:Androstanes dbc:Steroidal_antiandrogens dbc:Antiprogestogens dbc:Pyrazoles dbc:Sulfonamides |
| gold:hypernym |
dbr:Antiandrogen |
| rdf:type |
owl:Thing dul:ChemicalObject dbo:ChemicalSubstance wikidata:Q8386 yago:WikicatMolecularFormulas yago:WikicatSteroids yago:Abstraction100002137 yago:Chemical114806838 yago:Communication100033020 yago:Compound114818238 yago:Formula106816935 yago:Material114580897 yago:Matter100020827 yago:Message106598915 yago:MolecularFormula106817173 yago:OrganicCompound114727670 yago:Part113809207 yago:PhysicalEntity100001930 yago:Relation100031921 dbo:Drug yago:Statement106722453 yago:Steroid115057744 yago:Substance100019613 |
| rdfs:comment |
Zanoterone (INN, USAN) (former developmental code name WIN-49596), also known as (5α,17α)-1'-(methylsulfonyl)-1'-H-pregn-20-yno[3,2-c]pyrazol-17-ol, is a steroidal antiandrogen which was never marketed. It was investigated for the treatment of benign prostatic hyperplasia (BPH) but failed to demonstrate sufficient efficacy in phase II clinical trials, and also showed an unacceptable incidence rate and severity of side effects (e.g., breast pain and gynecomastia). As such, it was not further developed. (en) |
| rdfs:label |
Zanoterone (en) |
| owl:sameAs |
freebase:Zanoterone yago-res:Zanoterone wikidata:Zanoterone dbpedia-tr:Zanoterone https://global.dbpedia.org/id/Z9PD |
| prov:wasDerivedFrom |
wikipedia-en:Zanoterone?oldid=1093428331&ns=0 |
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wiki-commons:Special:FilePath/Zanoterone.svg |
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wikipedia-en:Zanoterone |
| is dbo:wikiPageRedirects of |
dbr:C23H32N2O3S dbr:WIN-49,596 dbr:WIN-49596 dbr:WIN-49_596 dbr:WIN49,596 dbr:WIN49596 dbr:WIN_49,596 dbr:WIN_49596 dbr:WIN_49_596 dbr:Win-49,596 dbr:Win-49596 dbr:Win-49_596 dbr:Win49,596 dbr:Win49596 dbr:Win_49,596 dbr:Win_49596 dbr:Win_49_596 |
| is dbo:wikiPageWikiLink of |
dbr:Benorterone dbr:5α-Dihydroethisterone dbr:C23H32N2O3S dbr:Cioteronel dbr:List_of_steroidal_antiandrogens dbr:List_of_drugs:_Z dbr:Steroidal_antiandrogen dbr:WIN-49,596 dbr:WIN-49596 dbr:WIN-49_596 dbr:WIN49,596 dbr:WIN49596 dbr:WIN_49,596 dbr:WIN_49596 dbr:WIN_49_596 dbr:Win-49,596 dbr:Win-49596 dbr:Win-49_596 dbr:Win49,596 dbr:Win49596 dbr:Win_49,596 dbr:Win_49596 dbr:Win_49_596 |
| is foaf:primaryTopic of |
wikipedia-en:Zanoterone |
