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Clometerone

Not to be confused with Clomestrone.
Clometerone
Clinical data
Other namesClometherone; L-38000; 6α-Chloro-16α-methylprogesterone; 6α-Chloro-16α-methylpregn-4-ene-3,20-dione
ATC code
  • None
Identifiers
  • (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)
  • 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=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 (INNTooltip International Nonproprietary Name; developmental code L-38000; also known as clometherone (USANTooltip United States Adopted Name) or 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

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References

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  1. ^ Elks J (14 November 2014). "Clometerone". 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 (September 1962). "Disubstituted Progesterones. The 6,16-Chloro and Methyl Series". Journal of Medicinal and Pharmaceutical Chemistry. 91 (5): 1049–1053. doi:10.1021/jm01240a019. PMID 14056429.
  3. ^ Strauss JS, Pochi PE (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.