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]

Cyanoketone
Clinical data
Other namesCyanotrimethylandrostenolone; CTM; 2α-Cyano-4,4',17α-trimethylandrost-5-en-17β-ol-3-one
Identifiers
  • (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
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H33NO2
Molar mass355.522 g·mol−1
3D model (JSmol)
  • 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=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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See also

References
  1. Jones IC, Henderson IW (22 October 2013). General, Comparative and Clinical Endocrinology of the Adrenal Cortex. Elsevier Science. pp. 136–. ISBN 978-1-4832-5980-2.
  2. Thomas JA, Keenan EJ (6 December 2012). Principles of Endocrine Pharmacology. Springer Science & Business Media. pp. 280–. ISBN 978-1-4684-5036-1.
  3. Thomas JA, Keenan EJ (6 December 2012). Principles of Endocrine Pharmacology. Springer Science & Business Media. pp. 11–12. ISBN 978-1-4684-5036-1.
  4. Di Prisco CL, Materazzi G, Scattolini B (1971). "Inhibition of steroidogenesis by cyanoketone". Gynecologic Investigation. 2 (1): 309–15. doi:10.1159/000301873. PMID 4266510.
  5. Bavister BD (6 December 2012). Preimplantation Embryo Development. Springer Science & Business Media. pp. 30–. ISBN 978-1-4613-9317-7.
  6. Norris DO, Carr JA (4 May 2013). Vertebrate Endocrinology. Academic Press. pp. 71–. ISBN 978-0-12-396465-6.
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