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

General Information of Drug (ID: DR5075)
Drug Name
Tolcapone
Synonyms
Tasmar; Roche brand of tolcapone; Ro 40-7592; Tasmar (TN); Tolcapone [USAN:INN]; Ro-40-7592; Tolcapone (JAN/USAN/INN); Methanone,(3,4-dihydroxy-5-nitrophenyl)(4-methylphenyl); (3,4-Dihydroxy-5-nitrophenyl)(4-methylphenyl)methanone; (3,4-dihydroxy-5-nitrophenyl)-(4-methylphenyl)methanone; 3,4-Dihydroxy-4'-methyl-5-nitrobenzophenone; 3,4-dihydroxy-5'-methyl-5-nitrobenzophenone
Indication Parkinsonism [ICD11: 8A00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 273.24 Topological Polar Surface Area 103
Heavy Atom Count 20 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
4659569
ChEBI ID
CHEBI:63630
CAS Number
134308-13-7
TTD Drug ID
D0Y7PG
Formula
C14H11NO5
Canonical SMILES
CC1=CC=C(C=C1)C(=O)C2=CC(=C(C(=C2)O)O)[N+](=O)[O-]
InChI
InChI=1S/C14H11NO5/c1-8-2-4-9(5-3-8)13(17)10-6-11(15(19)20)14(18)12(16)7-10/h2-7,16,18H,1H3
InChIKey
MIQPIUSUKVNLNT-UHFFFAOYSA-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
Tolcapone Metabolite M2 DM016411
91800246
Oxidation - Oxidation 1 [3]
Tolcapone Metabolite M3 DM016379
86206254
Reduction - Reduction 1 [3]
Tolcapone Metabolite M4 DM016685
137553879
Conjugation - Glucuronidation 1 [4]
Tolcapone Metabolite M4 DM016685
137553879
Conjugation - Glucuronidation 1 [3]
Tolcapone Metabolite M5 DM016498
102207668
Conjugation - Sulfation 1 [3]
Tolcapone Metabolite M11 DM016410
91800236
Conjugation - Sulfation 2 [3]
Tolcapone Metabolite M12 DM018288 N. A. Oxidation - Oxidation 2 [3]
Tolcapone Metabolite M6 DM018284 N. A. Conjugation - Sulfation 2 [3]
Tolcapone Metabolite M7 DM016412
91800251
Oxidation - Oxidation 2 [3]
Tolcapone Metabolite M8 DM018286 N. A. Oxidation - Methylation 2 [3]
Tolcapone Metabolite M10 DM018287 N. A. Oxidation - Oxidation 3 [3]
Tolcapone Metabolite M9 DM018285 N. A. Oxidation - Oxidation 3 [3]
⏷ Show the Full List of 12  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR010245 Tolcapone Tolcapone Metabolite M2 Oxidation - Oxidation Unclear [3]
MR010251 Tolcapone Tolcapone Metabolite M4 Conjugation - Glucuronidation Unclear [4]
MR010253 Tolcapone Tolcapone Metabolite M3 Reduction - Reduction Unclear [3]
MR010255 Tolcapone Tolcapone Metabolite M5 Conjugation - Sulfation Unclear [3]
MR010246 Tolcapone Metabolite M2 Tolcapone Metabolite M6 Conjugation - Sulfation Unclear [3]
MR010248 Tolcapone Metabolite M2 Tolcapone Metabolite M8 Oxidation - Methylation Unclear [3]
MR010250 Tolcapone Metabolite M2 Tolcapone Metabolite M7 Oxidation - Oxidation Unclear [3]
MR010254 Tolcapone Metabolite M3 Tolcapone Metabolite M11 Conjugation - Sulfation Unclear [3]
MR010252 Tolcapone Metabolite M4 Tolcapone Metabolite M12 Oxidation - Oxidation Unclear [3]
MR010247 Tolcapone Metabolite M6 Tolcapone Metabolite M9 Oxidation - Oxidation Unclear [3]
MR010249 Tolcapone Metabolite M8 Tolcapone Metabolite M10 Oxidation - Oxidation Unclear [3]
⏷ Show the Full List of 11 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]
References
1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 6646).
2 Effect of the Catechol-O-Methyltransferase Inhibitors Tolcapone and Entacapone on Fatty Acid Metabolism in HepaRG Cells
3 Analysis of an Integrated Human Multiorgan Microphysiological System for Combined Tolcapone Metabolism and Brain Metabolomics
4 Metabolism and excretion of tolcapone, a novel inhibitor of catechol-O-methyltransferase

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