Etynodiol

Etynodiol
Clinical data

ATC code	G03DC06 (WHO)
Identifiers
IUPAC name (3β,17β)-17-ethynylestr-4-ene-3,17-diol
CAS Number	1231-93-2
PubChem CID	14687
ChemSpider	14017
ECHA InfoCard	100.013.610
Chemical and physical data
Formula	C₂₀H₂₈O₂
Molar mass	300.435 g/mol
3D model (Jmol)	Interactive image
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), also known as 3β-hydroxynorethisterone, is a steroidal progestin related to norethisterone which was never marketed. A diacylated derivative, etynodiol diacetate, is used as a hormonal contraceptive. While etynodiol is sometimes used as a synonym for etynodiol diacetate, it usually refers to etynodiol diacetate, not etynodiol.

Etynodiol is a prodrug of norethisterone, and is converted immediately and completely into norethisterone. In addition, etynodiol is an intermediate in the conversion of the prodrug lynestrenol into norethisterone.

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.

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Wikipedia