Etynodiol diacetate

Etynodiol diacetate

Clinical data
Routes of administration	Oral
ATC code	G03DC06 (WHO) G03AA01 (WHO) G03FA06 (WHO) (with an estrogen)
Legal status
Legal status	℞ (Prescription only)
Identifiers
IUPAC name (3β,17β)-17-ethynylestr-4-ene-3,17-diyl diacetate
Synonyms	3β-Hydroxynorethisterone 3,17-diacetate
CAS Number	297-76-7
PubChem CID	92709270
DrugBank	DB00823
ChemSpider	8913
ECHA InfoCard	100.005.496
Chemical and physical data
Formula	C24H32O4
Molar mass	384.509 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(O[C@@H]4/C=C3\[C@@H]([C@H]2CC[C@]1([C@@H](CC[C@]1(C#C)OC(=O)C)[C@@H]2CC3)C)CC4)C
InChI InChI=1S/C24H32O4/c1-5-24(28-16(3)26)13-11-22-21-8-6-17-14-18(27-15(2)25)7-9-19(17)20(21)10-12-23(22,24)4/h1,14,18-22H,6-13H2,2-4H3/t18-,19-,20+,21+,22-,23-,24-/m0/s1 Key:ONKUMRGIYFNPJW-KIEAKMPYSA-N

Etynodiol diacetate (sold as Continuin, Femulen, Luteonorm, Luto-Metrodiol, and Metrodiol), or ethynodiol diacetate (USAN, BAN, JAN), also known as norethindrol diacetate or 3β-hydroxynorethisterone diacetate, is a steroidal progestin of the 19-nortestosterone group which is used as a hormonal contraceptive. It is the 3β,17β-diacetate ester of etynodiol, and acts as a rapidly converted prodrug to norethisterone, with etynodiol occurring as an intermediate. Etynodiol diacetate has weak androgenic activity, and, unlike most progestins but similarly to norethisterone and noretynodrel, also has some estrogenic activity.

Etynodiol diacetate is virtually inactive in terms of affinity for the progesterone and androgen receptors and acts as a prodrug of etynodiol, which in turn is a prodrug of norethisterone. Upon oral administration and during first-pass metabolism in the liver, etynodiol diacetate is rapidly converted by esterases into etynodiol, which is followed by oxygenation of the C3 hydroxyl group to produce norethisterone.