Cyanoketone, also known as 2α-cyano-4,4',17α-trimethylandrost-5-en-17β-ol-3-one (CTM), is a synthetic androstane steroid and a steroidogenesis inhibitor which is used in scientific research. On account of its structural similarity to pregnenolone, cyanoketone binds to and acts as a potent, selective, and irreversible inhibitor of 3β-hydroxysteroid dehydrogenase (3β-HSD), an enzyme that is responsible for the conversion of pregnenolone into progesterone, 17α-hydroxypregnenolone into 17α-hydroxyprogesterone, DHEA into androstenedione, and androstenediol into testosterone. As such, cyanoketone inhibits the production of both gonadal and adrenal steroids, including progesterone, androgens, estrogens, and corticosteroids. The drug is too toxic for therapeutic use in humans, and so has been used
Property |
Value |
dbo:abstract |
Cyanoketone, also known as 2α-cyano-4,4',17α-trimethylandrost-5-en-17β-ol-3-one (CTM), is a synthetic androstane steroid and a steroidogenesis inhibitor which is used in scientific research. On account of its structural similarity to pregnenolone, cyanoketone binds to and acts as a potent, selective, and irreversible inhibitor of 3β-hydroxysteroid dehydrogenase (3β-HSD), an enzyme that is responsible for the conversion of pregnenolone into progesterone, 17α-hydroxypregnenolone into 17α-hydroxyprogesterone, DHEA into androstenedione, and androstenediol into testosterone. As such, cyanoketone inhibits the production of both gonadal and adrenal steroids, including progesterone, androgens, estrogens, and corticosteroids. The drug is too toxic for therapeutic use in humans, and so has been used instead exclusively as a research tool. (en) |
dbo:casNumber |
4248-66-2 |
dbo:fdaUniiCode |
EPG65S4XCZ |
dbo:pubchem |
20243 |
dbo:thumbnail |
wiki-commons:Special:FilePath/Cyanoketone.png?width=300 |
dbo:wikiPageID |
23484761 (xsd:integer) |
dbo:wikiPageLength |
5508 (xsd:nonNegativeInteger) |
dbo:wikiPageRevisionID |
1108856059 (xsd:integer) |
dbo:wikiPageWikiLink |
dbc:Cholesterol_side-chain_cleavage_enzyme_inhibitors dbr:Potency_(pharmacology) dbr:Pregnenolone dbr:Progesterone dbr:Enzyme_inhibitor dbr:Androgen dbc:Abandoned_drugs dbc:Androstanes dbc:Ketones dbc:Tertiary_alcohols dbr:Corticosteroid dbr:Chemical_structure dbr:Estrogen dbr:Enzyme dbr:Androstane dbr:Androstenediol dbr:Androstenedione dbr:Steroid dbr:Scientific_research dbc:Nitriles dbr:Testosterone dbc:3β-Hydroxysteroid_dehydrogenase_inhibitors dbc:CYP17A1_inhibitors dbr:Adrenal_steroid dbr:Binding_selectivity dbr:Biosynthesis dbr:Biotransformation dbr:Toxicity dbr:Azastene dbr:Steroidogenesis_inhibitor dbr:Synthetic_compound dbr:17α-hydroxypregnenolone dbr:17α-hydroxyprogesterone dbr:3β-hydroxysteroid_dehydrogenase dbr:Gonadal_steroid dbr:Irreversible_inhibitor |
dbp:c |
23 (xsd:integer) |
dbp:casNumber |
4248 (xsd:integer) |
dbp:chemspiderid |
19069 (xsd:integer) |
dbp:h |
33 (xsd:integer) |
dbp:iupacName |
-17 (xsd:integer) |
dbp:n |
1 (xsd:integer) |
dbp:o |
2 (xsd:integer) |
dbp:pubchem |
20243 (xsd:integer) |
dbp:smiles |
N#C[C@H]4CCC (en) |
dbp:stdinchi |
1 (xsd:integer) |
dbp:stdinchikey |
GTBRTGPZZALPNS-MXHVRSFHSA-N (en) |
dbp:synonyms |
-2640.0 |
dbp:unii |
EPG65S4XCZ (en) |
dbp:verifiedfields |
changed (en) |
dbp:verifiedrevid |
424937956 (xsd:integer) |
dbp:watchedfields |
changed (en) |
dbp:width |
225 (xsd:integer) |
dbp:wikiPageUsesTemplate |
dbt:Drugbox dbt:Reflist dbt:Short_description dbt:Steroid-stub dbt:Abbrlink dbt:Cascite dbt:Chemspidercite dbt:Fdacite dbt:Stdinchicite |
dcterms:subject |
dbc:Cholesterol_side-chain_cleavage_enzyme_inhibitors dbc:Abandoned_drugs dbc:Androstanes dbc:Ketones dbc:Tertiary_alcohols dbc:Nitriles dbc:3β-Hydroxysteroid_dehydrogenase_inhibitors dbc:CYP17A1_inhibitors |
gold:hypernym |
dbr:Androstenol |
rdf:type |
owl:Thing dul:ChemicalObject dbo:ChemicalSubstance wikidata:Q8386 yago:WikicatNitriles yago:WikicatSteroids yago:Abstraction100002137 yago:Chemical114806838 yago:Compound114818238 yago:Material114580897 yago:Matter100020827 yago:Nitrile114827346 yago:OrganicCompound114727670 yago:Part113809207 yago:PhysicalEntity100001930 yago:Relation100031921 dbo:ChemicalCompound dbo:Drug yago:Steroid115057744 yago:Substance100019613 umbel-rc:ChemicalSubstanceType |
rdfs:comment |
Cyanoketone, also known as 2α-cyano-4,4',17α-trimethylandrost-5-en-17β-ol-3-one (CTM), is a synthetic androstane steroid and a steroidogenesis inhibitor which is used in scientific research. On account of its structural similarity to pregnenolone, cyanoketone binds to and acts as a potent, selective, and irreversible inhibitor of 3β-hydroxysteroid dehydrogenase (3β-HSD), an enzyme that is responsible for the conversion of pregnenolone into progesterone, 17α-hydroxypregnenolone into 17α-hydroxyprogesterone, DHEA into androstenedione, and androstenediol into testosterone. As such, cyanoketone inhibits the production of both gonadal and adrenal steroids, including progesterone, androgens, estrogens, and corticosteroids. The drug is too toxic for therapeutic use in humans, and so has been used (en) |
rdfs:label |
Cyanoketone (en) |
owl:sameAs |
freebase:Cyanoketone yago-res:Cyanoketone wikidata:Cyanoketone http://azb.dbpedia.org/resource/سیانوکتون dbpedia-fa:Cyanoketone dbpedia-sh:Cyanoketone dbpedia-sr:Cyanoketone https://global.dbpedia.org/id/4iZLJ |
prov:wasDerivedFrom |
wikipedia-en:Cyanoketone?oldid=1108856059&ns=0 |
foaf:depiction |
wiki-commons:Special:FilePath/Cyanoketone.png |
foaf:isPrimaryTopicOf |
wikipedia-en:Cyanoketone |
is dbo:wikiPageRedirects of |
dbr:Cyanotrimethylandrostenolone |
is dbo:wikiPageWikiLink of |
dbr:C23H33NO2 dbr:3β-Hydroxysteroid_dehydrogenase dbr:List_of_MeSH_codes_(D04) dbr:Azastene dbr:Steroidogenesis_inhibitor dbr:Cyanotrimethylandrostenolone |
is foaf:primaryTopic of |
wikipedia-en:Cyanoketone |