Compound: finasteride
SMILES: O=C1N[C@H]2[C@]([C@@H]3[C@H]([C@H]4[C@]([C@@H](C(=O)NC(C)(C)C)CC4)(C)CC3)CC2)(C)C=C1
InChIKey: DBEPLOCGEIEOCV-WSBQPABSSA-N
Synonyms: finasteride, 98319-26-7, Proscar, Propecia, Finastid, Prostide, Chibro-Proscar, MK-906, Finasterida, Finpecia, Finasteridum, MK 906, DTXSID3020625, N-tert-Butyl-3-oxo-4-aza-5alpha-androst-1-ene-17beta-carboxamide, MK906, (5alpha,17beta)-(1,1-Dimethylethyl)-3-oxo-4-azaandrost-1-ene-17-carboxamide, NSC-741485, 57GNO57U7G, NSC-759318, DTXCID50625, N-(2-Methyl-2-propyl)-3-oxo-4-aza-5-alpha-androst-1-ene-17-beta-carboxamide, 4-Azaandrost-1-ene-17-carboxamide, N-(1,1-dimethylethyl)-3-oxo-, (5alpha,17beta)-, CHEBI:5062, ENTADFI COMPONENT FINASTERIDE, Propeshia, Chibro Proscar, Aindeem, Urprosan, Pro-Cure, (1S,2R,7R,10S,11S,14S,15S)-N-tert-butyl-2,15-dimethyl-5-oxo-6-azatetracyclo(8.7.0.0^(2,7).0^(11,15))heptadec-3-ene-14-carboxamide, (1S,2R,7R,10S,11S,14S,15S)-N-tert-butyl-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-3-ene-14-carboxamide, RefChem:57216, D11AX10, G04CB01, (5ALPHA,17BETA)-N-(1,1-DIMETHYLETHYL)-3-OXO-4-AZAANDROST-1-ENE-17-CARBOXAMIDE, (1S,2R,7R,10S,11S,14S,15S)-N-tert-butyl-2,15-dimethyl-5-oxo-6-azatetracyclo(8.7.0.02,7.011,15)heptadec-3-ene-14-carboxamide, N-tert-Butyl-3-oxo-4-aza-5alpha-androst-1-en-17beta-carboxamide, MFCD00869737, C23H36N2O2, (1S,3aS,3bS,5aR,9aR,9bS,11aS)-N-tert-butyl-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide, CHEMBL710, (4aR,4bS,6aS,7S,9aS,9bS,11aR)-N-(tert-butyl)-4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide, (4aR,4bS,6aS,7S,9aS,9bS,11aR)-N-tert-butyl-4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide, Finasteridum [INN-Latin], Finasterida [INN-Spanish], (4aR,4bS,6aS,7S,9aS,9bS,11aR)-N-(1,1-dimethylethyl)-4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide, Andozac, Propecia (TN), SMR000466304, Proscar (TN), MK 0906, MK-0906, CCRIS 7438, HSDB 6793, SR-01000759414, BRN 4269024, UNII-57GNO57U7G, L-652,931, Finasteride CRS, 17beta-(N-tert-butylcarbamoyl)-4-aza-5 alpha-androst-1-en-3-one, NCGC00016965-01, Finasteride [USAN:USP:INN:BAN], CAS-98319-26-7, YM-152, KS-1058, Finasteride (Proscar), Finasteride (Standard), FINASTERIDE [MI], Prestwick0_000717, Prestwick1_000717, Prestwick2_000717, Prestwick3_000717, FINASTERIDE [INN], FINASTERIDE [JAN], FINASTERIDE [USAN], FINASTERIDE [VANDF], SCHEMBL5509, FINASTERIDE [MART.], BSPBio_000933, FINASTERIDE [WHO-DD], MLS000759404, MLS001165768, MLS001424046, Finasteride (JAN/USP/INN), SPBio_002854, BPBio1_001027, GTPL6818, orb1310564, Finasteride - Bio-X trade mark, FINASTERIDE [EP IMPURITY], FINASTERIDE [ORANGE BOOK], 4-Azaandrost-1-ene-17-carboxamide, N-(1,1-dimethylethyl)-3-oxo-, (5.alpha.,17.beta.)-, FINASTERIDE [EP MONOGRAPH], FINASTERIDE [USP IMPURITY], GLXC-07945, HMS1570O15, HMS2051F09, HMS2090G22, HMS2097O15, HMS2235L23, HMS3714O15, FINASTERIDE [USP MONOGRAPH], EX-A1951, Tox21_110717, Tox21_201506, Tox21_302744, BDBM50334788, EBC-07651, HY-13635R, MSK011113, NSC741485, NSC757443, s1197, AKOS015894916, Tox21_110717_1, CCG-100937, CS-1767, DB01216, FF23286, Finasteride, >=98% (HPLC), powder, MSK011113-100A, NC00187, NSC 741485, NSC 759318, NSC-757443, NCGC00093560-05, NCGC00256334-01, NCGC00259057-01, BF164456, CPD000466304, HY-13635, SY058000, AB00513901, NS00010893, D00321, Finasteride Solution in Acetonitrile, 100ug/mL, AB00513901-07, AB00513901-08, AB00513901_09, Finasteride, VETRANAL(TM), analytical standard, Q424167, SR-01000759414-4, SR-01000759414-6, BRD-K01095011-001-03-5, BRD-K01095011-001-15-9, Z1501475008, Finasteride, British Pharmacopoeia (BP) Reference Standard, Finasteride, European Pharmacopoeia (EP) Reference Standard, (17beta-(N-tert-butylcarbamoyl)-4-aza-5alpha-androst-1-en-3-one, Finasteride, United States Pharmacopeia (USP) Reference Standard, (5a,17b)-N-(1,1-Dimethylethyl)-3-oxo-4-azaandrost-1-ene-17-carboxamide, 4-Azaandrost-1-ene-17-carboxamide,1-dimethylethyl)-3-oxo-, (5.alpha., 17.beta.)-, Finasteride for peak identification, European Pharmacopoeia (EP) Reference Standard, (4AR,4BS,6AS,7S,9AS,9BS,11AR)-4A,6A-DIMETHYL-2-OXO-2,4A,4B,5,6,6A,7,8,9,9A,9B,10,11,11A-TETRADECAHYDRO-1H-INDENO[5,4-F]QUINOLINE-7-CARBOXYLIC ACID TERT-BUTYLAMIDE, (4aR,4bS,6aS,9aS,9bS,11aR)-4a,6a-Dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxylic acid tert-butylamide, (4aR,6aS)-4a,6a-Dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxylic acid tert-butylamide, (4aR,6aS,11aR)-4a,6a-Dimethyl-2-oxo-hexadecahydro-indeno[5,4-f]quinoline-7-carboxylic acid tert-butylamide, (4aR,6aS,7S)-4a,6a-Dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxylic acid tert-butylamide, (4aR,6aS,7S,11aR)-4a,6a-Dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxylic acid tert-butylamide, (R)-4a,6a-Dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxylic acid tert-butylamide, 1H-Indeno[5,4-f]quinoline-7-carboxamide, N-(1,1-dimethylethyl)-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-4a,6a-dimethyl-2-oxo-, (4aR,4bS,6aS,7S,9aS,9bS,11aR)-, 4a,6a,9a-Trimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxylic acid (Finasteride), 4a,6a-Dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxylic acid tert-butylamide(Finasteride)
Theoretical properties:
molecular_formula: C23H36N2O2
molecular_weight: 372.5 g/mol
exact_mass: 372.277678395 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 2
heavy_atom_count: 27
topological_polar_surface_area: 58.2 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: White to off-white crystalline solid
color: White to off-white crystalline solid
melting_point: 252-254 °C
solubility: Slightly soluble
Descriptions:
pubchem: Finasteride is an aza-steroid that is a synthetic drug for the treatment of benign prostatic hyperplasia. It has a role as an androgen antagonist, an EC 1.3.1.22 [3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+))] inhibitor and an antihyperplasia drug. It is an aza-steroid, a 3-oxo steroid and a delta-lactam. It derives from a hydride of a 5alpha-androstane.
chebi: An aza-steroid that is a synthetic drug for the treatment of benign prostatic hyperplasia.
chembl: FINASTERIDE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Finasteride, sold under the brand names Proscar and Propecia among others, is a medication used to treat pattern hair loss and benign prostatic hyperplasia (BPH). It can also be used to treat excessive hair growth in women. It is usually taken orally but there are topical formulations for patients with hair loss, designed to minimize systemic exposure by acting specifically on hair follicles.
Finasteride is a 5α-reductase inhibitor and therefore an antiandrogen. It works by decreasing the production of dihydrotestosterone (DHT) by about 70%.
In addition to DHT, finasteride also inhibits the production of several anticonvulsant neurosteroids including allopregnanolone, androstanediol, and tetrahydrodeoxycorticosterone.
Adverse effects from finasteride are rare in men with already enlarged prostates; however, some men experience sexual dysfunction, depression, and breast enlargement. In some men, sexual dysfunction may persist after stopping the medication. It may also hide the early symptoms of certain forms of prostate cancer.
Finasteride was patented in 1984 and approved for medical use in 1992. It is available as a generic medication. In 2023, it was the 91st most commonly prescribed medication in the United States, with more than 7 million prescriptions.