Cyanoketone

Cyanoketone, also known as 2α-cyano-4,4',17α-trimethylandrost-5-en-17β-ol-3-one (CTM),^[1] is a synthetic androstane steroid and a steroidogenesis inhibitor which is used in scientific research.^[2][3][4] 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),^[1][5] an enzyme that is responsible for the conversion of pregnenolone into progesterone, 17α-hydroxypregnenolone into 17α-hydroxyprogesterone, DHEATooltip dehydroepiandrosterone into androstenedione, and androstenediol into testosterone.^[2][3][6] As such, cyanoketone inhibits the production of both gonadal and adrenal steroids, including progesterone,^[5] androgens, estrogens, and corticosteroids.^[3][6] The drug is too toxic for therapeutic use in humans, and so has been used instead exclusively as a research tool.^[2][3]

Other namesCyanotrimethylandrostenolone; CTM; 2α-Cyano-4,4',17α-trimethylandrost-5-en-17β-ol-3-one

CAS Number

• 4248-66-2 ^Y

PubChem CID

• 20243

ChemSpider

• 19069 ^N

Quick facts Clinical data, Other names ...

Cyanoketone

Clinical data
Other names	Cyanotrimethylandrostenolone; CTM; 2α-Cyano-4,4',17α-trimethylandrost-5-en-17β-ol-3-one
Identifiers
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
CAS Number	4248-66-2 Y
PubChem CID	20243
ChemSpider	19069 N
UNII	EPG65S4XCZ
CompTox Dashboard (EPA)	DTXSID50962528
Chemical and physical data
Formula	C23H33NO2
Molar mass	355.522 g·mol−1
3D model (JSmol)	Interactive image
SMILES N#C[C@H]4C(=O)C(C\3=C\C[C@@H]2[C@H](CC[C@]1([C@H]2CC[C@@]1(O)C)C)[C@@]/3(C)C4)(C)C
InChI InChI=1S/C23H33NO2/c1-20(2)18-7-6-15-16(21(18,3)12-14(13-24)19(20)25)8-10-22(4)17(15)9-11-23(22,5)26/h7,14-17,26H,6,8-12H2,1-5H3/t14-,15+,16-,17-,21+,22-,23-/m0/s1 N Key:GTBRTGPZZALPNS-MXHVRSFHSA-N N
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