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Clomegestone acetate

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
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
  • (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
PubChemCID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC24H31ClO4
Molar mass418.96 g·mol−1
3D model (JSmol)
  • CC1CC2C3C=C(C4=CC(=O)CCC4(C3CCC2(C1(C(=O)C)OC(=O)C)C)C)Cl
  • 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 (USANTooltip United States Adopted Name) (developmental code nameSH-741), orclomagestone acetate, also known as6-chloro-17α-acetoxy-16α-methylpregna-4,6-diene-3,20-dione, is asteroidalprogestin of the17α-hydroxyprogesterone group which was developed as anoral contraceptive but was never marketed.[1][2] It is theacetateester ofclomegestone, which, similarly to clomegestone acetate, was never marketed.[1] Clomegestone acetate is also the 17-desoxycogener ofclometherone, and is somewhat more potent in comparison.[3] Similarly tocyproterone acetate, clomegestone acetate has been found to alterinsulin receptor concentrations inadipose tissue,[4] and this may indicate the presence ofglucocorticoid activity.[5][6]

References

[edit]
  1. ^abElks 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):667–672.doi:10.1530/acta.0.0860667.PMID 579029.
  5. ^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):667–672.doi:10.1530/acta.0.0860667.PMID 579029.
  6. ^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):305–313.doi:10.1530/acta.0.0750305.PMID 4406547.
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists
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