Compound: Gestrinone
SMILES: O=C1C=C2C(=C3C=C[C@@]4([C@](O)(C#C)CC[C@H]4[C@@H]3CC2)CC)CC1
InChIKey: BJJXHLWLUDYTGC-ANULTFPQSA-N
Synonyms: Gestrinone, 16320-04-0, Dimetriose, Ethylnorgestrienone, Gestrinona, R-2323, Gestrinonum, RU 2323, Ru-2323, R 2323, DTXSID4023094, A-46745, (8S,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthren-3-one, 1421533RCM, A 46 745, 13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregna-4,9,11-trien-20-yn-3-one, 18,19-Dinorpregna-4,9,11-trien-20-yn-3-one, 13-ethyl-17-hydroxy-, (17alpha)-, DTXCID603094, A-46-745, Pregna-4,9,11-trien-20-yn-3-one, 13-ethyl-17-hydroxy-18,19-dinor-, (17alpha)-, (10S,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo(8.7.0.0^(2,7).0^(11,15))heptadeca-1,6,16-trien-5-one, (10S,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1,6,16-trien-5-one, (8S,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,14,15,16-octahydrocyclopenta(a)phenanthren-3-one, RefChem:389006, R2323, G03XA02, Nemestran, Dimetrose, Tridomose, Gestrigone, NCGC00167457-01, Gestrinone (1mg/ml in Acetonitrile), Gestrinonum [INN-Latin], Gestrinona [INN-Spanish], CAS-16320-04-0, A 46745, BRN 5610726, Gestrinone [USAN:INN:BAN], UNII-1421533RCM, BJJXHLWLUDYTGC-ANULTFPQSA-N, Gestrinone (Standard), GESTRINONE [MI], 13-Ethyl-17-alpha-ethinyl-17-hydroxygon-4,9,11-trien-3-one, GESTRINONE [INN], GESTRINONE [JAN], Gestrinone (USAN/INN), GESTRINONE [USAN], 13-beta-Ethyl-17-alpha-ethinyl-17-hydroxy-gona-4,9,11-triene-3-one, GESTRINONE [MART.], GESTRINONE [WHO-DD], SCHEMBL217651, CHEMBL1868702, CHEBI:89642, HMS2089K16, HMS3715A15, MSK10950, Tox21_112461, BDBM50423515, AKOS015894932, Gestrinone (1 mg/ml in Acetonitrile), Tox21_112461_1, CCG-220967, CS-6362, DB11619, HY-101405R, 18,19-Dinor-17-alpha-pregna-4,9,11-trien-20-yn-3-one, 13-ethyl-17-hydroxy-, 18,19-Dinorpregna-4,9,11-trien-20-yn-3-one, 13-ethyl-17-hydroxy-, (17-alpha)-, 18,19-Dinorpregna-4,9,11-trien-20-yn-3-one, 13-ethyl-17-hydroxy-, (17.alpha.)-, NCGC00167457-02, FG156783, HY-101405, G0436, NS00098763, D04317, D90768, AB01275442-01, SR-01000872705, Q3761406, SR-01000872705-1, BRD-K97472745-001-01-8, 13-Ethyl-17a-ethynyl-17b-hydroxygona-4,9,11-trien-3-one, (17a)-13-ethyl-17-hydroxy-18,19-Dinorpregna-4,9,11-trien-20-yn-3-one, 13-ethyl-17-hydroxy-18,19-Dinor-17a-pregna-4,9,11-trien-20-yn-3-one, 13-ethyl-17alpha-hydroxy-18,19-dinorpregna-4,9,11-trien-20-yn-3-one, (17alpha)-13-Ethyl-17-hydroxy-18,19-dinorpregna-4,9,11-trien-20-yn-3-one, (1R,3aS,3bS,11aS)-11a-Ethyl-1-ethynyl-1-hydroxy-1,2,3,3a,3b,4,5,8,9,11a-decahydro-7H-cyclopenta[a]phenanthren-7-one, PREGNA-4,9,11-TRIEN-20-YN-3-ONE, 13-ETHYL-17-HYDROXY-18,19-DINOR-, (17.ALPHA.)-
Theoretical properties:
molecular_formula: C21H24O2
molecular_weight: 308.4 g/mol
exact_mass: 308.177630004 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:
melting_point: 150-152
Descriptions:
pubchem: Gestrinone is an oxo steroid.
chembl: GESTRINONE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: Gestrinone, sold under the brand names Dimetrose and Nemestran among others, is a medication which is used in the treatment of endometriosis. It has also been used to treat other conditions such as uterine fibroids and heavy menstrual bleeding and has been investigated as a method of birth control. Gestrinone is used alone and is not formulated in combination with other medications. It is taken by mouth or in through the vagina.
Side effects of gestrinone include menstrual abnormalities, estrogen deficiency, and symptoms of masculinization like acne, seborrhea, breast shrinkage, increased hair growth, and scalp hair loss, among others. Gestrinone has a complex mechanism of action, and is characterized as a mixed progestogen and antiprogestogen, a weak androgen and anabolic steroid, a weak antigonadotropin, a weak steroidogenesis inhibitor, and a functional antiestrogen.
Gestrinone was introduced for medical use in 1986. It has been used extensively in Europe but appears to remains marketed only in a few countries throughout the world. The medication is not available in the United States. Due to its anabolic effects, the use of gestrinone in competition has been banned by the International Olympic Committee.