Epostane

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Epostane
Epostane.svg
Names
IUPAC name
4α,5α-Epoxy-3,17β-dihydroxy-4β,17α-dimethylandrost-2-ene-2-carbonitrile
Other names
Win-32729
Identifiers
3D model (Jmol)
ChemSpider
Properties
C22H31NO3
Molar mass 357.49 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Epostane (INN, USAN, BAN) (developmental code name WIN-32729) is an inhibitor of 3β-hydroxysteroid dehydrogenase (3β-HSD) that was developed as an contraceptive, abortifacient, and oxytocic drug but was never marketed.[1][2] By inhibiting 3β-HSD, epostane blocks the biosynthesis of progesterone from pregnenolone (and also the conversion of dehydroepiandrosterone to androstenedione), thereby functioning as an antiprogestogen and terminating pregnancy.[1] The drug was trialed and in a study was found to be slightly more effective at inducing abortion relative to mifepristone.[3]

Synthesis[edit]

Epostane synthesis: Sterling Drug, R. G. Christiansen, DE 2855091  (1979).

See also[edit]

References[edit]

  1. ^ a b J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 492–. ISBN 978-1-4757-2085-3. 
  2. ^ I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 113–. ISBN 978-94-011-4439-1. 
  3. ^ Gillian C. L. Lachelin (11 September 2013). Introduction to Clinical Reproductive Endocrinology. Elsevier Science. pp. 198–. ISBN 978-1-4831-9380-9.