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Cyanoketone
Sign in to saveCyanoketone, 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, into androstenedione, and androstenediol into testosterone. As such, cyanoketone i
Chemical data
- Formula
- C23H33NO2
- Molecular weight
- 355.5 g/mol
- IUPAC name
- (2S,8R,9S,10R,13S,14S,17S)-17-hydroxy-4,4,10,13,17-pentamethyl-3-oxo-1,2,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthrene-2-carbonitrile
- SMILES
- C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C)O)CC=C4[C@@]3(C[C@H](C(=O)C4(C)C)C#N)C
- InChIKey
- GTBRTGPZZALPNS-MXHVRSFHSA-N
- XLogP
- 4.1
- Polar surface area
- 61.1 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 355.251129
Show 3 more facts
- chemical formula
- C₂₃H₃₃NO₂
- isomeric SMILES
- C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C)O)CC=C4[C@@]3(C[C@H](C(=O)C4(C)C)C#N)C
- canonical SMILES
- CC1(C2=CCC3C4CCC(C4(CCC3C2(CC(C1=O)C#N)C)C)(C)O)C
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
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, 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.
== See also == Azastene Epostane
Excerpted from Wikipedia’s “Cyanoketone” article, available under the CC BY-SA 4.0 licence.