Compound: GESTODENE
SMILES: O=C1C=C2[C@@H]([C@@H]3[C@H]([C@@H]4C=C[C@@]([C@@]4(CC)CC3)(O)C#C)CC2)CC1
InChIKey: SIGSPDASOTUPFS-XUDSTZEESA-N
Synonyms: GESTODENE, 60282-87-3, Gestoden, Gestodeno, SH B 331, Gestodenum, DTXSID6046478, SH-B-331, 1664P6E6MI, DTXCID4026478, 13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregna-4,15-dien-20-yn-3-one, 18,19-Dinorpregna-4,15-dien-20-yn-3-one, 13-ethyl-17-hydroxy-, (17-alpha)-, Pregna-4,15-dien-20-yn-3-one, 13-ethyl-17-hydroxy-18,19-dinor-, (17alpha)-, (1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo(8.7.0.0^(2,7).0^(11,15))heptadeca-6,12-dien-5-one, (1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,12-dien-5-one, 17-alpha-ethinyl-13-ethyl-17 beta-hydroxy-4,15-gonadien-3-one, RefChem:639914, 13-ethyl-17-hydroxy-18,19-dinor-17 alpha-pregna-4,15-dien-20-yn-3-one, 262-145-8, Gestodenum [INN-Latin], Gestodeno [INN-Spanish], MFCD00867858, (8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14-decahydrocyclopenta[a]phenanthren-3-one, 18,19-Dinorpregna-4,15-dien-20-yn-3-one, 13-ethyl-17-hydroxy-, (17a)-, Gestinol, (8R,9S,10R,13S,14S,17R)-13-Ethyl-17-ethynyl-17-hydroxy-6,7,8,9,10,11,12,13,14,17-decahydro-1H-cyclopenta[a]phenanthren-3(2H)-one, Gestodene [USAN:INN:BAN], CAS-60282-87-3, CCRIS 9189, HSDB 3594, EINECS 262-145-8, BRN 4237181, SHB 331;WL 70, UNII-1664P6E6MI, Gestodene CRS, NCGC00164611-01, Gestodene; 13-Ethyl-17-hydroxy-18,19-dinor-17a-pregna-4,15-dien-20-yn-3-one; Gestinol; SHB 331; WL 70; 18,19-Dinorpregna-4,15-dien-20-yn-3-one, 13-ethyl-17-hydroxy-, (17alpha)-, Gestodene (Standard), GESTODENE [INN], GESTODENE [MI], Gestodene (USAN/INN), GESTODENE [HSDB], GESTODENE [USAN], 17-alpha-Ethinyl-13-ethyl-17-beta-hydroxy-4,15-gonadien-3-one, GESTODENE [MART.], GESTODENE [WHO-DD], SCHEMBL37271, Gestodene - Bio-X trade mark, orb1308480, GESTODENE [EP IMPURITY], Gestodene for system suitability, CHEMBL1213583, GESTODENE [EP MONOGRAPH], Gestodene, >=98% (HPLC), GTPL11246, HY-B0110R, SHB-331, SHT-546, CHEBI:135323, HY-B0110, Tox21_112232, AC-474, BDBM50247973, Gestodene for system suitability CRS, MSK011114, s1376, SH-546, AKOS024462671, Femodene (ethinylestradiol, gestodene), Tox21_112232_1, CCG-267584, CS-1862, DB06730, FG23660, MSK011114-100A, 18,19-Dinorpregna-4,15-dien-20-yn-3-one, 13-ethyl-17-hydroxy-, (17alpha)-, Millinette (ethinylestradiol, gestodene), NCGC00263565-01, AC-20038, AS-13029, BG164505, G0404, Gestodene Solution in Acetonitrile, 100ug/mL, D04316, SBI-0654203.0001, AB01274782-01, AB01274782_02, Q408289, BRD-K97197005-001-03-2, Gestodene, European Pharmacopoeia (EP) Reference Standard, 17alpha -Ethynyl-17beta-hydroxy-18-methyl-4,15-estradien-3-one, 17alpha-ethynyl-17beta-hydroxy-18-methyl-4,15-estradien-3-one, 17alpha-ethynyl-17beta-hydroxy-18-methyl-estra-4,15-dien-3-one, (17a)-13-Ethyl-17-hydroxy-18,19-dinorpregna-4,15-dien-20-yn-3-one, (17alpha)-13-Ethyl-17-hydroxy-18,19-dinorpregna-4,15-dien-20-yn-3-one, 13beta-Ethyl-17beta-hydroxy-18,19-dinorpregna-4,15-dien-20-yn-3-one, (1R,3aS,3bR,9aR,9bS,11aS)-11a-Ethyl-1-ethynyl-1-hydroxy-1,3a,3b,4,5,8,9,9a,9b,10,11,11a-dodecahydro-7H-cyclopenta[a]phenanthren-7-one, (8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,13,14,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one
Theoretical properties:
molecular_formula: C21H26O2
molecular_weight: 310.4 g/mol
exact_mass: 310.193280068 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 2
heavy_atom_count: 23
topological_polar_surface_area: 37.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals from acetone-hexane
color: Crystals from acetone-hexane
Descriptions:
pubchem: Gestodene is a steroid. It has a role as an estrogen.
chembl: GESTODENE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.
wikipedia: Gestodene, sold under the brand names Femodene and Minulet among others, is a progestin medication which is used in birth control pills for women. It is also used in menopausal hormone therapy. The medication is available almost exclusively in combination with an estrogen. It is taken by mouth.
Side effects of the combination of an estrogen and gestodene include menstrual irregularities, headaches, nausea, breast tenderness, mood changes, and others. Gestodene 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 activity, weak antimineralocorticoid activity, and weak glucocorticoid activity.
Gestodene was discovered in 1975 and was introduced for medical use, specifically in birth control pills, in 1987. It was subsequently introduced for use in menopausal hormone therapy as well. Gestodene is sometimes referred to as a "third-generation" progestin. It is marketed in birth control pills widely throughout the world, whereas it is available for use in menopausal hormone therapy only a few countries. Gestodene is not approved in the United States.