Etynodiol diacetate

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Etynodiol diacetate
Ethynodiol diacetate.svg
Systematic (IUPAC) name
(3β,17β)-17-ethynylestr-4-ene-3,17-diyl diacetate
Clinical data
Legal status
  • (Prescription only)
Routes of
CAS Registry Number 297-76-7
ATC code G03DC06
G03AA01 G03FA06 (with an estrogen)
PubChem CID: 92709270
DrugBank DB00823
ChemSpider 8913
Chemical data
Formula C24H32O4
Molecular mass 384.509 g/mol

Ethynodiol diacetate (INN; sold as Continuin, Femulen, Luteonorm, Luto-Metrodiol, and Metrodiol), or ethynodiol diacetate (USAN, BAN), is a steroidal progestin which is used as a hormonal contraceptive.[1][2] Relative to other 19-nortestosterone derivatives, it has relatively little or no potency as an androgen,[3][4] and also unlike most progestins in general, has significant estrogenic effects.[5][3]


Ethynodiol diacetate synthesis:[6] 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:[7]

Reduction of norethindrone (1) affords the 3,17-diol. The 3β-hydroxy compound is the desired product; since reactions at C-3 do not show nearly the stereoselectivity as those at C-17 by virtue of the relative lack of stereo-directing proximate substituents, the formation of the desired isomer is engendered by use of a bulky reducing agent, Lithium tri-tert-butoxyaluminum hydride. Acetylation of the 3β,17β-diol affords Etynodiol diacetate (3), one of the most potent oral progestins.[6]

See also[edit]


  1. ^ F.. Macdonald (1997). Dictionary of Pharmacological Agents. CRC Press. p. 1454. ISBN 978-0-412-46630-4. Retrieved 12 May 2012. 
  2. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 422. ISBN 978-3-88763-075-1. Retrieved 30 May 2012. 
  3. ^ a b Kenneth L. Becker (24 April 2001). Principles and Practice of Endocrinology and Metabolism. Lippincott Williams & Wilkins. p. 1004. ISBN 978-0-7817-1750-2. Retrieved 30 May 2012. 
  4. ^ Chaudhuri (1 January 2007). Practice Of Fertility Control: A Comprehensive Manual (7Th Edition). Elsevier India. p. 122. ISBN 978-81-312-1150-2. Retrieved 30 May 2012. 
  5. ^ Allan H. Goroll; Albert G. Mulley (27 January 2009). Primary Care Medicine: Office Evaluation and Management of the Adult Patient. Lippincott Williams & Wilkins. p. 876. ISBN 978-0-7817-7513-7. Retrieved 30 May 2012. 
  6. ^ a b 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. 
  7. ^ 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.