Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0695)
Drug Name
Finasteride
Synonyms
Finasterida; Finasterida [INN-Spanish]; Finasteridum; Finasteridum [INN-Latin]; Finastid; Finpecia; L-652,931; MK 0906; MK 906; Chibro-Proscar; MK-0906; MK-906; Propecia; Proscar; Prostide; finasteride; (5alpha,17beta)-(1,1-Dimethylethyl)-3-oxo-4-azaandrost-1-ene-17-carboxamide; 57GNO57U7G; 98319-26-7; BRN 4269024; CCRIS 7438; CHEBI:5062; CHEMBL710; HSDB 6793; N-tert-Butyl-3-oxo-4-aza-5alpha-androst-1-ene-17beta-carboxamide; UNII-57GNO57U7G
Indication Prostatic hyperplasia [ICD11: GA90] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 372.5 Topological Polar Surface Area 58.2
Heavy Atom Count 27 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
57363
PubChem SID
7847387 ; 7979227 ; 8185196 ; 11466745 ; 11467865 ; 11486590 ; 11528597 ; 11533303 ; 12014292 ; 12146021 ; 14779683 ; 14926633 ; 24724479 ; 24861022 ; 25819911 ; 26719811 ; 43115066 ; 46386559 ; 46507645 ; 47424400 ; 47646719 ; 48094722 ; 48394119 ; 48413780 ; 48416011 ; 49666458 ; 49681675 ; 49699149 ; 53790828 ; 56313630 ; 57313897 ; 57649138 ; 74382929 ; 75258634 ; 85788501 ; 91146246 ; 92125899 ; 92308339 ; 92309138 ; 99437022 ; 99444245 ; 103194727 ; 103914483 ; 103975037 ; 104312468 ; 117571916 ; 118048887 ; 121363570 ; 124658933 ; 124757073
ChEBI ID
ChEBI:5062
CAS Number
98319-26-7
TTD Drug ID
D08IWD
Formula
C23H36N2O2
Canonical SMILES
CC12CCC3C(C1CCC2C(=O)NC(C)(C)C)CCC4C3(C=CC(=O)N4)C
InChI
1S/C23H36N2O2/c1-21(2,3)25-20(27)17-8-7-15-14-6-9-18-23(5,13-11-19(26)24-18)16(14)10-12-22(15,17)4/h11,13-18H,6-10,12H2,1-5H3,(H,24,26)(H,25,27)/t14-,15-,16-,17+,18+,22-,23+/m0/s1
InChIKey
DBEPLOCGEIEOCV-WSBQPABSSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
6alpha-hydroxyfinasteride DM000180
29981554
Oxidation - Oxidation 1 [4]
Finasteride monocarboxylic acid metabolite DM000182 N. A. Oxidation - Oxidation 1 [6]
Omega-hydroxyfinasteride DM000175
131770009
Oxidation - Hydroxylation 1 [4] , [6]
Unclear DM009999 N. A. Unclear 1 [7]
Dihydroxyfinasteride DM000181
102064310
Oxidation - Oxidation 2 [4]
Hydroxyfinasteride glucuronide DM000179
156596523
Conjugation - Glucuronidation 2 [4]
Omega-aldehyde finasteride DM000176 N. A. Oxidation - Oxidation 2 [4]
Finasteride-omega-oic acid DM000177
18632991
Oxidation - Oxidation 3 [4]
Finasteride carboxylic acid giucuronide DM000178 N. A. Oxidation - Oxidation 4 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001035 Finasteride Omega-hydroxyfinasteride Oxidation - Hydroxylation CYP3A4 [4], [6]
MR001036 Finasteride 6alpha-hydroxyfinasteride Oxidation - Oxidation CYP3A4 [4]
MR001037 Finasteride Finasteride monocarboxylic acid metabolite Oxidation - Oxidation CYP3A4 [6]
MR001038 Finasteride . Unclear CYP3A5 [7]
MR001034 6alpha-hydroxyfinasteride Dihydroxyfinasteride Oxidation - Oxidation CYP3A4 [4]
MR001030 Omega-hydroxyfinasteride Omega-aldehyde finasteride Oxidation - Oxidation CYP3A4 [4]
MR001031 Omega-hydroxyfinasteride Hydroxyfinasteride glucuronide Conjugation - Glucuronidation UGT1A4 [4]
MR001032 Omega-aldehyde finasteride Finasteride-omega-oic acid Oxidation - Oxidation CYP3A4 [4]
MR001033 Finasteride-omega-oic acid Finasteride carboxylic acid giucuronide Oxidation - Oxidation CYP3A4 [4]
⏷ Show the Full List of 9 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[3]
UDP-glucuronosyltransferase 1A4 (UGT1A4) DME0048 Homo sapiens
UD14_HUMAN
2.4.1.17
[4]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1355 Akkermansia muciniphila Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1445 Parabacteroides distasonis Not Available Not Available [5]
⏷ Show the Full List of 12  DME(s)
References
1 Finasteride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
3 Drug Interactions Flockhart Table
4 Finasteride for hair loss: a review J Dermatolog Treat. 2022 Jun;33(4):1938-1946. doi: 10.1080/09546634.2021.1959506.
5 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
6 LABEL:FINASTERIDE tablet
7 Drug Interactions Flockhart Table:Docetaxel

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