Compound: tibolone
SMILES: O=C1CC2=C([C@@H]3[C@H]([C@H]4[C@]([C@](O)(C#C)CC4)(C)CC3)[C@@H](C2)C)CC1
InChIKey: WZDGZWOAQTVYBX-XOINTXKNSA-N
Synonyms: tibolone, 5630-53-5, Liviella, Livial, Org OD 14, Tibolona, Xyvion, Tibolonum, 17-Hydroxy-7alpha-methyl-19-nor-17alpha-pregn-5(10)-en-20-yn-3-one, ORG-OD 14, (7R,8R,9S,13S,14S,17R)-17-ethynyl-17-hydroxy-7,13-dimethyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one, DTXSID5023667, FF9X0205V2, NSC-759898, DTXCID103667, CHEBI:32223, 17alpha-ethynyl-17beta-hydroxy-7alpha-methylestr-5(10)-en-3-one, tibilone, Org OD14, (7R,8R,9S,13S,14S,17R)-17-ethynyl-17-hydroxy-7,13-dimethyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta(a)phenanthren-3-one, RefChem:898105, G03DC05, 19-Norpregn-5(10)-en-20-yn-3-one, 17-hydroxy-7-methyl-, (7-alpha,17-alpha)-, 227-069-1, Boltin, (1S,9R,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-9,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-2(7)-en-5-one, (17R)-17-hydroxy-7alpha-methyl-19-norpregn-5(10)-en-20-yn-3-one, Tibolone (1mg/ml in Acetonitrile), (7alpha,17beta)-17-ethynyl-17-hydroxy-7-methylestr-5(10)en-3-one, (7alpha,17alpha)-17-hydroxy-7-methyl-19-norpregn-5(10)-en-20-yn-3-one, CAS-5630-53-5, Tibolonum [INN-Latin], Tibolona [INN-Spanish], Tibolone [USAN:INN:BAN], Tibofem, UNII-FF9X0205V2, 19-Norpregn-5(10)-en-20-yn-3-one, 17-hydroxy-7-methyl-, (7.alpha.,17.alpha.)-, NCGC00164632-01, EINECS 227-069-1, TIBOLONE [USAN], Org-OD14, TIBOLONE [INN], TIBOLONE [JAN], TIBOLONE [MI], TIBOLONE [VANDF], TIBOLONE [MART.], Tibolone Impurity Standard, TIBOLONE [WHO-DD], SCHEMBL41172, Org OD 14;Org OD14, Tibolone (JAN/USAN/INN), MLS001424234, TIBOLONE [EP IMPURITY], GTPL9711, orb2276857, TIBOLONE [EP MONOGRAPH], CHEMBL2103774, HMS2052K21, HMS2090B10, HMS2232B13, HMS3649J14, HMS3712J15, Tibolone for system suitability CRS, Tibolone (1 mg/ml in Acetonitrile), Tox21_112250, KB-889, MSK011092, AKOS015963197, Tox21_112250_1, CCG-101148, DB09070, FT35065, GS-3562, MSK011092-100A, NC00398, NSC 759898, NCGC00164632-02, AC-20036, AC-31722, CPD000469219, SMR000469219, CS-0080970, NS00009920, Tibolone Solution in Acetonitrile, 100ug/mL, D01639, AB00698273-05, Q413805, SR-01000763531, SR-01000946727, SR-01000763531-3, SR-01000946727-1, 17-Hydroxy-7alpha-methyl-17alpha-19-norpregn-5(10)-en-20-yn-3-one, 17.alpha.-Hydroxy-7.alpha.-methyl-19-norpregn-5(10)-en-20-yn-3-one, 19-Norpregn-5(10)-en-20-yn-3-one, 17-hydroxy-7-methyl-, (7alpha,17alpha)-, (7beta,8xi,9beta,13alpha,14beta,17alpha)-17-ethynyl-17-hydroxy-7-methylestr-5(10)-en-3-one, (7R,8R,9S,13S,14S,17R)-17-ethynyl-17-hydroxy-7,13-dimethyl-4,6,7,8,9,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one
Theoretical properties:
molecular_formula: C21H28O2
molecular_weight: 312.4 g/mol
exact_mass: 312.208930132 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 1
heavy_atom_count: 23
topological_polar_surface_area: 37.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
solubility: <0.1 g/L
Descriptions:
pubchem: Tibolone is estran-3-one with a double bond between positions 5 and 10, and bearing both an ethynyl group and a hydroxy group at position 17 (R-configuration). A synthetic steroid hormone drug which acts as an agonist at all five type I steroid hormone receptors, it is used in the prevention of postmenopausal osteoporosis and for treatment of endometriosis. It has a role as a bone density conservation agent and a hormone agonist. It is a 17beta-hydroxy steroid and a terminal acetylenic compound.
chebi: Estran-3-one with a double bond between positions 5 and 10, and bearing both an ethynyl group and a hydroxy group at position 17 (<i>R</i>-configuration). A synthetic steroid hormone drug which acts as an agonist at all five type I steroid hormone receptors, it is used in the prevention of postmenopausal osteoporosis and for treatment of endometriosis.
chembl: TIBOLONE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.
wikipedia: Tibolone, sold under the brand name Livial among others, is a medication which is used in menopausal hormone therapy and in the treatment of postmenopausal osteoporosis and endometriosis. The medication is available alone and is not formulated or used in combination with other medications. It is taken by mouth.
Side effects of tibolone include acne and increased hair growth among others. Tibolone is a synthetic steroid with weak estrogenic, progestogenic, and androgenic activity, and hence is an agonist of the estrogen, progesterone, and androgen receptors. It is a prodrug of several metabolites. The estrogenic effects of tibolone may show tissue selectivity in their distribution.
Tibolone was developed in the 1960s and was introduced for medical use in 1988. It is marketed widely throughout the world. The medication is not available in the United States.