Etynodiol

Etynodiol
Clinical data
ATC code G03DC06 (WHO)
Identifiers
CAS Number 1231-93-2
PubChem (CID) 14687
ChemSpider 14017
Chemical and physical data
Formula C20H28O2
Molar mass 300.435 g/mol
3D model (Jmol) Interactive image

Etynodiol (INN), or ethynodiol (BAN), also known as 3β-hydroxynorethisterone,[1] is a steroidal progestin related to norethisterone which was never marketed.[2][3] A diacylated derivative, etynodiol diacetate, is used as a hormonal contraceptive.[2][3] While etynodiol is sometimes used as a synonym for etynodiol diacetate, what is usually being referred to is actually etynodiol diacetate and not etynodiol.

Pharmacology

Etynodiol is a prodrug of norethisterone, and is converted immediately and completely into norethisterone.[4][5][6] In addition, etynodiol is an intermediate in the conversion of the prodrug lynestrenol into norethisterone.[7]

Chemistry

Etynodiol is a 19-nortestosterone derivative. Structurally, it is almost identical to norethisterone and lynestrenol, differing only in its C3 substituent. Whereas norethisterone has a ketone at C3 and lynestrenol has no substituent at C3, etynodiol has a hydroxyl group at the position.

Synthesis

Ethynodiol diacetate synthesis:[8] F. B. Colton, U.S. Patent 2,843,609 (1958 to Searle). Prepn of the 3-acetate, 17-acetate, and diacetate: P. D. Klimstra, U.S. Patent 3,176,013 (1965 to Searle); see also:[9]

See also

References

  1. ↑ Schindler, Adolf E; Campagnoli, Carlo; Druckmann, René; Huber, Johannes; Pasqualini, Jorge R; Schweppe, Karl W; Thijssen, Jos H.H (2003). "Classification and pharmacology of progestins". Maturitas. 46: 7–16. doi:10.1016/j.maturitas.2003.09.014. ISSN 0378-5122.
  2. 1 2 F.. Macdonald (1997). Dictionary of Pharmacological Agents. CRC Press. p. 1454. ISBN 978-0-412-46630-4. Retrieved 12 May 2012.
  3. 1 2 Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 422. ISBN 978-3-88763-075-1. Retrieved 30 May 2012.
  4. ↑ Donna Shoupe; Florence P. Haseltine (6 December 2012). Contraception. Springer Science & Business Media. pp. 21–. ISBN 978-1-4612-2730-4.
  5. ↑ Bhattacharya (1 January 2003). Pharmacology, 2/e. Elsevier India. pp. 378–. ISBN 978-81-8147-009-6.
  6. ↑ IARC Working Group on the Evaluation of Carcinogenic Risks to Humans; World Health Organization; International Agency for Research on Cancer (2007). Combined Estrogen-progestogen Contraceptives and Combined Estrogen-progestogen Menopausal Therapy. World Health Organization. pp. 146–. ISBN 978-92-832-1291-1.
  7. ↑ Hammerstein J (1990). "Prodrugs: advantage or disadvantage?". Am. J. Obstet. Gynecol. 163 (6 Pt 2): 2198–203. PMID 2256526.
  8. ↑ Klimstra, P.; Colton, F. (1967). "The synthesis of 3β-hydroxyestr-4-en-17-one and 3β-hydroxiandrost-4-en-17-one". Steroids. 10 (4): 411. doi:10.1016/0039-128X(67)90119-5.
  9. ↑ Sondheimer, F.; Klibansky, Y. (1959). "Synthesis of 3β-hydroxy analogues of steroidal hormones, a biologically active class of compounds". Tetrahedron. 5: 15. doi:10.1016/0040-4020(59)80066-1.


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