Etynodiol diacetate

Etynodiol diacetate
Clinical data
Trade names	Ovulen, Demulen, others
Other names	Ethynodiol diacetate; Norethindrol diacetate; 3β-Hydroxynorethisterone 3β,17β-diacetate; 17α-Ethynylestr-4-ene-3β,17β-diyl diacetate; CB-8080; SC-11800
License data	US DailyMed: Ethynodiol;
Pregnancy; category	Contraindicated;
Routes of; administration	By mouth
Drug class	Progestogen; Progestin; Progestogen ester
ATC code	G03DC06 (WHO) ; G03AA01 (WHO) G03FA06 (WHO) (with an estrogen);
Legal status
Legal status	AU: S4 (Prescription only); US: ℞-only; In general: ℞ (Prescription only);
Identifiers
	IUPAC name [(3S,8R,9S,10R,13S,14S,17R)-17-acetyloxy-17-ethynyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate;
CAS Number	297-76-7; 8056-92-6;
PubChem CID	9270;
DrugBank	DB00823;
ChemSpider	8913;
UNII	62H10A1236;
KEGG	D01294;
ChEBI	CHEBI:31580;
ChEMBL	ChEMBL1200624;
CompTox Dashboard (EPA)	DTXSID4020614 ;
ECHA InfoCard	100.005.496
Chemical and physical data
Formula	C24H32O4
Molar mass	384.516 g·mol−1
3D model (JSmol)	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, or ethynodiol diacetate, sold under the brand name Ovulen among others, is a progestin medication which is used in birth control pills. The medication is available only in combination with an estrogen. It is taken by mouth.

Etynodiol diacetate is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. It has weak androgenic and estrogenic activity and no other important hormonal activity. The medication is a prodrug of norethisterone in the body, with etynodiol occurring as an intermediate.

Etynodiol, a related compound, was discovered in 1954, and etynodiol diacetate was introduced for medical use in 1965. The combination ethynodiol with mestranol (Ovulen) was approved for medical use in the United States in 1966. The combination ethinylestradiol with ethynodiol (Demulen) was approved for medical use in the United States in 1970.

In 2021, the combination with ethinylestradiol was the 276th most commonly prescribed medication in the United States, with more than 800,000 prescriptions.

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