Compound: ETHYNODIOL DIACETATE
SMILES: O=C(O[C@]1(C#C)[C@@]2([C@H]([C@H]3[C@@H]([C@@H]4C(=C[C@@H](OC(=O)C)CC4)CC3)CC2)CC1)C)C
InChIKey: ONKUMRGIYFNPJW-KIEAKMPYSA-N
Synonyms: ETHYNODIOL DIACETATE, 297-76-7, Femulen, Continuin, Etynodiol Acetate, Etynodiol diacetate, SC 11800, SC-11800, 19-Nor-17alpha-pregn-4-en-20-yne-3beta,17-diol diacetate, DTXSID4020614, CHEBI:31580, NSC-759288, (3-beta,17-alpha)-19-Norpregn-4-en-20-yne-3,17-diol diacetate, 17-alpha-Ethynyl-19-norandrost-4-ene-3-beta,17-beta-diol diacetate, 17alpha-Ethynyl-3,17-dihydroxy-4-estrene diacetate, 17alpha-Ethynylestr-4-ene-3beta,17beta-diol acetate, 3beta, 17beta-Diacetoxy-17alpha-ethynyl-4-oestrene, 17alpha-Ethynyl-4-estrene-3beta,17beta-diol diacetate, DTXCID00614, [(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, 3beta,17beta-Diacetoxy-19-nor-17alpha-pregn-4-en-20-yne, 62H10A1236, 17alpha-Ethynyl-19-norandrost-4-ene-3beta,17-beta-diol diacetate, 19-norpregn-4-en-20-yn-3beta,17alpha-diol, diacetate, ZOVIA COMPONENT ETHYNODIOL DIACETATE, 19-Norpregn-4-en-20-yne-3,17-diol, diacetate, (3beta,17alpha)-, ((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, RefChem:596812, (3 beta, 17 alpha)-19-Norpregn-4-en-20-yne-3,17 diol Diacetate, 206-044-9, Ethyndiol Diacetate, Ethinodiol diacetate, Metrodiol, Luto-metrodiol, Cervicundin, Metrodiol diacetate, Ovulen 50, MFCD00083326, Ethynodiol (diacetate), Ethynodiol acetate, (3beta,17beta)-17-ethynylestr-4-ene-3,17-diyl diacetate, 19-Norpregn-4-en-20-yne-3,17-diol, diacetate, (3b,17a)-, (3S,8R,9S,10R,13S,14S,17R)-17-ethynyl-13-methyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diyl diacetate, NCGC00166138-01, Ethynodiol diacetate [USAN], Etynodiol di(acetate), CCRIS 305, 8080 C. B., Ethynodiol diacetate [Progestins], EINECS 206-044-9, 17-alpha-Ethynyl-3,17-dihydroxy-4-estrene diacetate, 3-beta, 17-beta-Diacetoxy-17-alpha-ethynyl-4-oestrene, 17-alpha-Ethynylestr-4-ene-3-beta,17-beta-diol acetate, 17-alpha-Ethynyl-4-estrene-3-beta,17-beta-diol diacetate, 19-Norpregn-4-en-20-yne-3,17-diol, diacetate, (3.beta.,17.alpha.)-, Ethynodiol diacetate (JAN/USP), 3-beta,17-beta-Diacetoxy-19-nor-17-alpha-pregn-4-en-20-yne, Ethynodiol diacetate [USAN:USP], UNII-62H10A1236, NCGC00186466-01, ethynodiol-diacetate, CAS-297-76-7, 19-Nor-17-alpha-pregn-4-en-20-yne-3-beta,17-diol diacetate, Prestwick0_000908, Prestwick1_000908, Prestwick2_000908, Prestwick3_000908, SCHEMBL40888, BSPBio_000756, MLS000028661, SPBio_002955, 17alpha-ethynylestr-4-ene-3beta,17beta-diyl diacetate, BPBio1_000832, GTPL7072, orb1310092, Ethynodiol diacetate (Standard), CHEMBL1200624, HY-B1089R, ETHYNODIOL DIACETATE [MI], MSK1611, ETHYNODIOL DIACETATE [JAN], HMS1570F18, HMS2097F18, HMS3714F18, ETYNODIOL DIACETATE [MART.], HY-B1089, Tox21_112333, Tox21_112924, BDBM50237627, ETYNODIOL DIACETATE [WHO-DD], LMST02030124, s3160, ETHYNODIOL DIACETATE [USP-RS], AKOS015895252, Tox21_112333_1, CCG-220908, DB00823, NSC 759288, NCGC00166138-02, NCGC00166138-03, NCGC00166138-04, NCGC00166138-05, [(3S,8R,9S,10R,13S,14S,17R)-17-acetoxy-17-ethynyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate, AS-13382, ETHYNODIOL DIACETATE [ORANGE BOOK], SMR000058858, SY111397, ETHYNODIOL DIACETATE [USP IMPURITY], ETHYNODIOL DIACETATE [USP MONOGRAPH], KELNOR COMPONENT ETHYNODIOL DIACETATE, OVULEN COMPONENT ETHYNODIOL DIACETATE, AB00513958, E1315, NS00028774, D01294, T72249, AB00513958_02, SR-01000872687, Q5405160, SR-01000872687-1, BRD-K46331928-001-05-8, BRD-K46331928-001-06-6, 3beta,17alpha-19-Norpregn-4-en-20-yne-3,17-diyl diacetate, (3beta, 17alpha)-19-Norpregn-4-en-20-yne-3,17-diol diacetate, Ethynodiol diacetate, United States Pharmacopeia (USP) Reference Standard
Theoretical properties:
molecular_formula: C24H32O4
molecular_weight: 384.5 g/mol
exact_mass: 384.23005950 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 5
heavy_atom_count: 28
topological_polar_surface_area: 52.6 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 126-127
solubility: 3.97e-03 g/L
Descriptions:
pubchem: Ethynodiol diacetate is a steroid ester and a terminal acetylenic compound. It has a role as a contraceptive drug, a synthetic oral contraceptive and an estrogen receptor modulator. It is functionally related to an ethynodiol.
chembl: ETHYNODIOL DIACETATE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: 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.