tolcapone   Click here for help

GtoPdb Ligand ID: 6646

Synonyms: Ro 40-7592 | Ro-407592 | Tasmar®
Approved drug PDB Ligand
tolcapone is an approved drug (EMA (1997), FDA (1998))
Compound class: Synthetic organic
Comment: Tolcapone is a selective, potent and reversible nitro catechol type inhibitor of enzyme catechol-O-methyl transferase (COMT). As a result of reported hepatoxicity complications tolcapone has been withdrawn from the market in a number of countries.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 100.67
Molecular weight 273.06
XLogP 4.11
No. Lipinski's rules broken 0
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Canonical SMILES Cc1ccc(cc1)C(=O)c1cc(O)c(c(c1)[N+](=O)[O-])O
Isomeric SMILES Cc1ccc(cc1)C(=O)c1cc(O)c(c(c1)[N+](=O)[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
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Summary of Clinical Use Click here for help
Used in the treatment of Parkinson's disease as an adjunctive therapy.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Tolcapone inhibits enzyme activity of catechol-O-methyl transferase (COMT). This enzyme would normally degrade the levodopa (dopamine analogue) given alongside tolcapone. But in the presence of the inhibitor the levodopa can be utilised to replace the dopamine lacking in the brains of Parkinson's patients.
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