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Clometerone

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Clometerone
Clinical data

Other names	Clometherone; 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	5591-27-5
PubChem CID	14515731
ChemSpider	16736897
UNII	01L3E93T4C
CompTox Dashboard (EPA)	DTXSID20204508
Chemical and physical data
Formula	C₂₂H₃₁ClO₂
Molar mass	362.94 g·mol⁻¹
3D model (JSmol)	Interactive image
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 (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 derivativeofprogesterone 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]

References

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^ 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.

^ ^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.

^ 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.