|Chemical and physical data|
|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. It acts as a competitive inhibitor of 3β-hydroxysteroid dehydrogenase (IC50 = 1 μM), and thereby inhibiting the formation of progesterone, corticosteroids, androgens, and estrogens. Due to inhibition of corticosteroid synthesis, azastene is immunosuppressive.
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.
- 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.
- George W.A Milne (8 May 2018). Drugs: Synonyms and Properties: Synonyms and Properties. Taylor & Francis. pp. 1457–. ISBN 978-1-351-78989-9.
- 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.
- Progress in Medicinal Chemistry. Elsevier. 5 April 1991. pp. 259–. ISBN 978-0-08-086276-7.
- Gordon O. Potts, Sterling Drug Inc. U.S. Patent 3,966,926 (1976).
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