Clomegestone acetate

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 which 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]

Clomegestone acetate
Clinical data
Other namesClomagestone acetate; SH-741; 6-Chloro-17α-acetoxy-16α-methylpregna-4,6-diene-3,20-dione
Drug classProgestogen; Progestogen ester
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
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC24H31ClO4
Molar mass418.96 g·mol−1
3D model (JSmol)
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

References
  1. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 297–. ISBN 978-1-4757-2085-3.
  2. Lawrence MM (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. Lednicer D (20 June 2011). Steroid Chemistry at a Glance. John Wiley & Sons. pp. 5–. ISBN 978-1-119-95729-4.
  4. Krauth MC, Schillinger E (November 1977). "Changes in insulin receptor concentration in rat fat cells following treatment with the gestagens clomegestone acetate and cyproterone acetate". Acta Endocrinologica. 86 (3): 667–72. doi:10.1530/acta.0.0860667. PMID 579029.
  5. Schillinger E, Gerloff C, Gerhards E, Günzel P (February 1974). "Glucose tolerance and serum insulin in rats and insulin sensitivity of rat adipose cells following treatment with the progestogen clomegestone acetate". Acta Endocrinologica. 75 (2): 305–13. doi:10.1530/acta.0.0750305. PMID 4406547.
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