Clomegestone acetate

Clomegestone acetate

Identifiers
IUPAC name (1S,2R,10R,11S,13R,14R,15S)-14-acetyl-8-chloro-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-6,8-dien-14-yl acetate
CAS Number	424-89-5
PubChem (CID)	20055456
ChemSpider	16736896
UNII	8OIJ6341W7
KEGG	D03550
ChEMBL	CHEMBL2104126
Chemical and physical data
Formula	C24H31ClO4
Molar mass	418.95354 g/mol
3D model (Jmol)	Interactive image
SMILES CC1CC2C3C=C(C4=CC(=O)CCC4(C3CCC2(C1(C(=O)C)OC(=O)C)C)C)Cl
InChI InChI=1S/C24H31ClO4/c1-13-10-19-17-12-21(25)20-11-16(28)6-8-22(20,4)18(17)7-9-23(19,5)24(13,14(2)26)29-15(3)27/h11-13,17-19H,6-10H2,1-5H3/t13-,17-,18+,19+,22-,23+,24+/m1/s1 Key:WWSKHPDYSWDMNC-YRNSVOBJSA-N

Clomegestone acetate (USAN) (developmental code name SH-741), or clomagestone acetate, also known as 6-chloro-17α-acetoxy-16α-methylpregna-4,6-diene-3,20-dione, is a steroidal progestin of the 17α-hydroxyprogesterone group that was developed as an oral contraceptive but was never marketed.^[1][2] It is the acetate ester of clomegestone, which, similarly to clomegestone acetate, was never marketed.^[1] Clomegestone acetate is also the 17-desoxy cogener of clometherone, and is somewhat more potent in comparison.^[3] Similarly to cyproterone acetate, clomegestone acetate has been found to alter insulin receptor concentrations in adipose tissue, and this may indicate the presence of glucocorticoid activity.^[4][5]

References

1. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 297–. ISBN 978-1-4757-2085-3.
2. Mary Margaret Lawrence (1971). CENTO Workshop Series on Clinical and Applied Research in Family Planning, Ankara, Turkey, February 23-26: Tehran, Iran, March 1-4; Lahore, Pakistan, March 9-12, 1971; [papers. Central Treaty Organization.
3. Daniel Lednicer (20 June 2011). Steroid Chemistry at a Glance. John Wiley & Sons. pp. 5–. ISBN 978-1-119-95729-4.
4. Krauth, M. C.; Schillinger, E. (1977). "CHANGES IN INSULIN RECEPTOR CONCENTRATION IN RAT FAT CELLS FOLLOWING TREATMENT WITH THE GESTAGENS CLOMEGESTONE ACETATE AND CYPROTERONE ACETATE". European Journal of Endocrinology. 86 (3): 667–672. doi:10.1530/acta.0.0860667. ISSN 0804-4643.
5. Schillinger, E.; Gerloff, Ch.; Gerhards, E.; Gunzel, P. (1974). "GLUCOSE TOLERANCE AND SERUM INSULIN IN RATS AND INSULIN SENSITIVITY OF RAT ADIPOSE CELLS FOLLOWING TREATMENT WITH THE PROGESTOGEN CLOMEGESTONE ACETATE". European Journal of Endocrinology. 75 (2): 305–313. doi:10.1530/acta.0.0750305. ISSN 0804-4643.