Azastene

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
Azastene
Azastene.svg
Clinical data
Synonyms WIN-17625; 4,4,17α-Trimethylandrosta-2,5-dieno(2,3-d)isoxazol-17β-ol
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
Formula C23H33NO2
Molar mass 355.522 g/mol
3D model (JSmol)

Azastene (INN, USAN) (developmental code name WIN-17625) is a steroidogenesis inhibitor described as a contraceptive, luteolytic, and abortifacient which was never marketed.[1][2] It acts as a competitive inhibitor of 3β-hydroxysteroid dehydrogenase (IC50 = 1 μM), and thereby inhibiting the formation of progesterone, corticosteroids, androgens, and estrogens.[3][4] Due to inhibition of corticosteroid synthesis, azastene is immunosuppressive.[2]

Synthesis[edit]

Azastene synthesis:[5]

One synthesis of this compound involves initial alkylation of methyl testosterone by means of strong base and methyl iodide to afford the 4,4-dimethyl derivative. Formylation with alkoxide and methyl formate leads to the 2-hydroxymethyl derivative. Reaction of this last with hydroxylamine leads to formation of an isoxazole ring. There is then obtained azastene.

See also[edit]

References[edit]

  1. ^ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 113–. ISBN 978-1-4757-2085-3. 
  2. ^ a b George W.A Milne (8 May 2018). Drugs: Synonyms and Properties: Synonyms and Properties. Taylor & Francis. pp. 1457–. ISBN 978-1-351-78989-9. 
  3. ^ B. Runnebaum; T. Rabe; L. Kiesel (6 December 2012). Future Aspects in Contraception: Proceeding of an International Symposium held in Heidelberg, 5–8 September 1984 Part 1 Male Contraception. Springer Science & Business Media. pp. 74–. ISBN 978-94-009-4910-2. 
  4. ^ Progress in Medicinal Chemistry. Elsevier. 5 April 1991. pp. 259–. ISBN 978-0-08-086276-7. 
  5. ^ Gordon O. Potts, Sterling Drug Inc. U.S. Patent 3,966,926 (1976).