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Cyanoketone

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Chemical compound Pharmaceutical compound
Cyanoketone
Clinical data
Other namesCyanotrimethylandrostenolone; 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-decahydrocyclopentaphenanthrene-2-carbonitrile
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H33NO2
Molar mass355.522 g·mol
3D model (JSmol)
SMILES
  • N#C4C(=O)C(C\3=C\C2(CC1(2CC1(O)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
  • Key:GTBRTGPZZALPNS-MXHVRSFHSA-N
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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, DHEATooltip dehydroepiandrosterone 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

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): 309–315. 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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