Clometerone

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Not to be confused with Clomestrone.
Clometerone
Clometerone.svg
Clinical data
Other namesClometherone; L-38000; 6α-Chloro-16α-methylprogesterone; 6α-Chloro-16α-methylpregn-4-ene-3,20-dione
ATC code
  • None
Identifiers
IUPAC name
  • (6S,8S,9S,10R,13S,14S,16R,17S)-17-acetyl-6-chloro-10,13,16-trimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H31ClO2
Molar mass362.94 g·mol−1
3D model (JSmol)
SMILES
  • C[C@@H]1C[C@H]2[C@@H]3C[C@@H](C4=CC(=O)CC[C@@]4([C@H]3CC[C@@]2([C@H]1C(=O)C)C)C)Cl
InChI
  • InChI=1S/C22H31ClO2/c1-12-9-17-15-11-19(23)18-10-14(25)5-7-21(18,3)16(15)6-8-22(17,4)20(12)13(2)24/h10,12,15-17,19-20H,5-9,11H2,1-4H3/t12-,15-,16+,17+,19+,20-,21-,22+/m1/s1
  • Key:UMRURYMAPMZKQO-NDKKBYRMSA-N

Clometerone (INN) (developmental code name L-38000), or clometherone (USAN), also known as 6α-chloro-16α-methylprogesterone, is a synthetic pregnane steroid and derivative of progesterone which was reported in 1962 and is described as an antiestrogen and antiandrogen but was never marketed.[1][2][3]

Clometerone has been found to suppress estrone-induced uterine hypertrophy in mice at oral and parenteral doses in which progesterone is inactive (active at 10 µg with clometerone and progesterone inactive at 10–100 µg in the case of both routes).[2] However, its progestogenic potency in the Clauberg assay is considerably less than that of progesterone.[2] As such, the progestogenic effects of clometerone do not seem to parallel its estrogenic effects.[2] It was also studied as an antiandrogen in men but was found to slightly increase sebum production when given orally and to variably and inconsistently affect sebum production when given as a topical medication.[2]

See also[]

  • Steroidal antiandrogen
  • List of steroidal antiandrogens

References[]

  1. ^ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 298–. ISBN 978-1-4757-2085-3.
  2. ^ a b c d e RAPALA RT, MURRAY MJ (1962). "Disubstituted Progesterones. The 6,16-Chloro and Methyl Series". J Med Pharm Chem. 91 (5): 1049–53. doi:10.1021/jm01240a019. PMID 14056429.
  3. ^ Strauss, John S.; Pochi, Peter E. (1970). "Assay of anti-androgens in man by the sebaceous gland response". British Journal of Dermatology. 82 (s6): 33. doi:10.1111/j.1365-2133.1970.tb08003.x. ISSN 0007-0963. S2CID 73246983.



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