Compound: Dienogest
SMILES: O=C1C=C2C(=C3[C@H]([C@H]4[C@]([C@](O)(CC#N)CC4)(C)CC3)CC2)CC1
InChIKey: AZFLJNIPTRTECV-FUMNGEBKSA-N
Synonyms: Dienogest, 65928-58-7, Dienogestril, Dienogestum, Endometrion, STS 557, STS-557, MJR-35, 17alpha-17-Hydroxy-3-oxo-19-norpregna-4,9-diene-21-nitrile, 46M3EV8HHE, ZK 37659, M 18575, M-18575, 17-alpha-Cyanomethyl-17-beta-hydroxy-estra-4,9(10)-dien-3-one, 19-Norpregna-4,9-diene-21-nitrile, 17-hydroxy-3-oxo-, (17alpha)-, ZK-37659, CHEBI:70708, 17-Hydroxy-3-oxo-19-nor-17alpha-pregna-4,9-diene-21-nitrile, DTXSID80891478, 19-Norpregna-4,9-diene-21-nitrile, 17-hydroxy-3-oxo-, (17-alpha)-, [(17beta)-17-hydroxy-3-oxoestra-4,9-dien-17-yl]acetonitrile, ((17beta)-17-hydroxy-3-oxoestra-4,9-dien-17-yl)acetonitrile, 17 alpha-cyanomethyl-17 beta-hydroxyestra-4,9(10)-diene-3-one, RefChem:586937, 17 alpha-cyanomethyl-17 beta-hydroxy-13 beta-methylgona-4,9-dien-3-one, G03DB08, DTXCID101030584, Dienogestrel, Dinagest, Visanne, 2-[(8S,13S,14S,17R)-17-hydroxy-13-methyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]acetonitrile, MFCD00868356, 2-((8S,13S,14S,17R)-17-hydroxy-13-methyl-3-oxo-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)acetonitrile, Dienogest [INN], Dienogestum [Latin], (17-hydroxy-3-oxoestra-4,9-dien-17beta-yl)acetonitrile, 17alpha-Cyanomethyl-17beta-hydroxyestra-4,9(10)-dien-3-one, BAY86-5258, UNII-46M3EV8HHE, Dienogest [USAN:INN:BAN], Dienogest CRS, Endometrion (TN), Dienogest; Dienogestril; Dinagest; STS 557; (17alpha)-17-Hydroxy-3-oxo-19-norpregna-4,9-diene-21-nitrile; 17alpha-Cyanomethyl-17beta-hydroxyestra-4,9-dien-3-one, Dienogest (Standard), BAY 86-5258, DIENOGEST [JAN], DIENOGEST [MI], DIENOGEST [USAN], 17-alpha-Cyanomethyl-17-beta-hydroxyestra-4,9(10)-diene-3-one, DIENOGEST [VANDF], DIENOGEST [MART.], 17-Hydroxy-3-oxo-19-norpregna-4,9-diene-21-nitrile, DIENOGEST [WHO-DD], SCHEMBL37293, (17a)-17-Hydroxy-3-oxo-19-norpregna-4,9-diene-21-nitrile, Dienogest (JAN/USAN/INN), GTPL7654, STS557, DIENOGEST [ORANGE BOOK], Dienogest for system suitability, CHEMBL1201864, DIENOGEST [EP MONOGRAPH], Dienogest, >=98% (HPLC), HY-B0084R, SH-T00660AA, AZFLJNIPTRTECV-FUMNGEBKSA-N, GLXC-05824, HY-B0084, MSK10876, Dienogest for system suitability CRS, EBC-07864, s1251, AKOS015840152, AKOS015896680, AC-2166, CCG-267594, CS-1782, DB09123, FH21758, NCGC00346502-04, 2-[(1R,3aS,3bS,11aS)-1-hydroxy-11a-methyl-7-oxo-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl]acetonitrile, DA-72748, D5230, NS00000598, A10563, D03799, AB01566807_01, EN300-6477654, 17-Cyanomethyl-17-hydroxyestra-4, 9-dien-3-one, Q139160, SR-01000942230, SR-01000942230-1, BRD-K50853363-001-02-3, Dienogest, EuropePharmacopoeia (EP) Reference Standard, Z2235801839, 17-Hydroxy-3-oxo-17alpha-19-norpregna-4,9-diene-21-nitrile, Dienogest for system suitability, EuropePharmacopoeia (EP) Reference Standard
Theoretical properties:
molecular_formula: C20H25NO2
molecular_weight: 311.4 g/mol
exact_mass: 311.188529040 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 1
heavy_atom_count: 23
topological_polar_surface_area: 61.1 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 210-218
solubility: Practically insoluble
Descriptions:
pubchem: Dienogest is a steroid hormone that is 17beta-hydroxy-3-oxoestra-4,9-diene substituted at position 17 by a cyanomethyl group. Used as an oral contraceptive. It has a role as a synthetic oral contraceptive, a progestin and a progesterone receptor agonist. It is a steroid hormone, a 17beta-hydroxy steroid, a 3-oxo-Delta(4) steroid and an aliphatic nitrile. It derives from a hydride of an estrane.
chebi: A steroid hormone that is 17β-hydroxy-3-oxoestra-4,9-diene substituted at position 17 by a cyanomethyl group. Used as an oral contraceptive.
chembl: DIENOGEST is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Dienogest, sold under the brand name Visanne (manufactured by Bayer AG) among others, is a progestin medication which is used in birth control pills and in the treatment of endometriosis. It is also used in menopausal hormone therapy and to treat heavy periods. Dienogest is available both alone and in combination with estrogens. It is taken by mouth.
Side effects of dienogest include menstrual irregularities, headaches, nausea, breast tenderness, depression, and acne, among others. Dienogest is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. It is a unique progestogen, with strong effects in the uterus. The medication has some antiandrogenic activity, which may help to improve androgen-dependent symptoms like acne, and has no other important hormonal activity.
Dienogest was discovered in 1979 and was introduced for medical use in 1995. Additional formulations of dienogest were approved between 2007 and 2010. It is sometimes referred to as a "fourth-generation" progestin. Dienogest is marketed widely throughout the world. It is available as a generic medication.