Compound: ethynodiol
SMILES: O[C@]1(C#C)[C@@]2([C@H]([C@H]3[C@@H]([C@@H]4C(=C[C@@H](O)CC4)CC3)CC2)CC1)C
InChIKey: JYILPERKVHXLNF-QMNUTNMBSA-N
Synonyms: ethynodiol, Etynodiol, Ethinodiol, 1231-93-2, Aethynodiolum, Etinodiol, Etynodiolum, DTXSID1023025, 9E01C36A9S, (3beta,17alpha)-19-Norpregn-4-en-20-yne-3,17-diol, (3beta,17beta)-17-ethynylestr-4-ene-3,17-diol, 17alpha-Ethynyl-19-norandrost-4-ene-3beta,17beta-diol, 17-alpha-Ethynyl-19-norandrost-4-ene-3-beta,17-beta-diol, CHEBI:50785, Etynodol, RefChem:139219, 17 alpha-ethynyl-estra-4-ene-3 beta,17 beta-diol, DTXCID903025, 19-NORPREGN-4-EN-20-YNE-3,17-DIOL, (3BETA,17ALPHA)-, (3beta,17beta)-17-ethynylestr-4-ene-3,17-diol;17alpha-ethynylestr-4-ene-3beta,17beta-diol, 214-971-5, Etynodiol (INN), ETYNODIOL [INN], 17alpha-ethynylestr-4-ene-3beta,17beta-diol, Etinodiolo [DCIT], Etinodiolo, Etynodiol [INN:BAN], Etinodiol [INN-Spanish], Etynodiolum [INN-Latin], EINECS 214-971-5, UNII-9E01C36A9S, HSDB 7897, JYILPERKVHXLNF-QMNUTNMBSA-N, (3-beta,17-alpha)-19-Norpregn-4-en-20-yne-3,17-diol, ETHYNODIOL [MI], 3beta-hydroxynorethisterone, ETYNODIOL [WHO-DD], 17alpha-Ethynyl-estra-4-ene-3beta,17beta-diol, SCHEMBL140933, 19-Nor-17-alpha-pregn-4-en-20-yne-3-beta,17-diol, CHEMBL1201406, 19-Norpregn-4-en-20-yne-3,17-diol, (3-beta,17-alpha)-, 3.BETA.-HYDROXYLYNESTRENOL, 19-Norpregn-4-en-20-yne-3,17-diol, (3.beta.,17.alpha.)-, MSK10468, DB13866, (3S,8R,9S,10R,13S,14S,17R)-17-ethynyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol, D07939, 17alpha-19-Norpregn-4-en-20-yne-3beta,17-diol, Q5405158, (3.BETA.,17.BETA.)-17-ETHYNYLESTR-4-ENE-3,17-DIOL, 17.ALPHA.-ETHYNYL-4-OESTRENE-3.BETA.,17.BETA.-DIOL, ESTR-4-ENE-3,17-DIOL, 17-ETHYNYL-, (3.BETA.,17.BETA.)-
Theoretical properties:
molecular_formula: C20H28O2
molecular_weight: 300.4 g/mol
exact_mass: 300.208930132 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 1
heavy_atom_count: 22
topological_polar_surface_area: 40.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: Crystals from methanol + water. MW: 384.51. MP: approximately 126-127 °C. Spcific optical rotation: =72.5 deg at 25 °C/D (chlorform) /Ethyndiol diacetate/
solubility: Solubility in double-distilled water, 0.26 mg/L /Ethynodiol diacetate/
Descriptions:
pubchem: Ethynodiol is a 17beta-hydroxy steroid, a 3beta-hydroxy steroid and a terminal acetylenic compound. It has a role as a progestin.
chembl: ETHYNODIOL is a small molecule listed in the ChEMBL database and has reached clinical trial phase -1.0.
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.