Etynodiol

Etynodiol

Systematic (IUPAC) name
(3β,17β)-17-ethynylestr-4-ene-3,17-diol
Identifiers
CAS Number	1231-93-2
ATC code	G03DC06 (WHO)
PubChem	CID 14687
ChemSpider	14017
Chemical data
Formula	C20H28O2
Molar mass	300.435 g/mol
SMILES O[C@@H]4/C=C3\[C@@H]([C@H]2CC[C@]1([C@@H](CC[C@]1(C#C)O)[C@@H]2CC3)C)CC4
InChI InChI=1S/C20H28O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,12,14-18,21-22H,4-11H2,2H3/t14-,15-,16+,17+,18-,19-,20-/m0/s1 Key:JYILPERKVHXLNF-QMNUTNMBSA-N

Etynodiol (INN), or ethynodiol (BAN), is a steroidal progestin which was never marketed.^[1][2] A diacylated derivative, etynodiol diacetate, is used as a hormonal contraceptive.^[1][2]

While etynodiol is sometimes used as a synonym for etynodiol diacetate, what is usually being referred to is actually etynodiol diacetate and not etynodiol.

Synthesis

Ethynodiol diacetate synthesis:^[3] 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:^[4]

See also

• Etynodiol diacetate
• Progestin

References

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. 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.
4. 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.