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QuickView for Tolcapone (compound)


PubChem
Name: tolcapone
PubChem Compound ID: 4659569
Molecular formula: C14H11NO5
Molecular weight: 273.241 g/mol
Synonyms:
Tolcapone (JAN/USAN); 134308-13-7; Methanone, (3,4-dihydroxy-5-nitrophenyl)(4-methylphenyl)-; C07949; 3,4-Dihydroxy-4'-methyl-5-nitrobenzophenone; CCRIS 7904; D00786; Tolcapone [USAN:INN]; Tolcapone; Tasmar (TN).
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DrugBank
Identification
Name: tolcapone
Name (isomeric): DB00323
Drug Type: small molecule
Brand: Tasmar
Category: Antidyskinetics, Antiparkinson Agents, Enzyme Inhibitors, Central Nervous System Agents
CAS number: 134308-13-7
Pharmacology
Indication: Used as an adjunct to levodopa/carbidopa therapy for the symptomatic treatment of Parkinson's Disease. This drug is generally reserved for patients with parkinsonian syndrome receiving levodopa/carbidopa who are experiencing symptom fluctuations and are not responding adequately to or are not candidates for other adjunctive therapies.
Pharmacology:
Tolcapone is a potent, selective, and reversible inhibitor of catechol-O-methyltransferase (COMT). In humans, COMT is distributed throughout various organs. COMT catalyzes the transfer of the methyl group of S-adenosyl-L-methionine to the phenolic group of substrates that contain a catechol structure. Physiological substrates of COMT include dopa, ...
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Mechanism of Action:
The precise mechanism of action of tolcapone is unknown, but it is believed to be related to its ability to inhibit COMT and alter the plasma pharmacokinetics of levodopa, resulting in an increase in plasma levodopa concentrations. The inhibition of COMT also causes a reduction in circulating 3-OMD as a result of decreased peripheral metabolism of ...
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Absorption: Rapidly absorbed (absolute bioavailability is about 65%)
Protein binding: > 99.9% (to serum albumin)
Biotransformation: The main metabolic pathway of tolcapone is glucuronidation
Route of elimination: Tolcapone is almost completely metabolized prior to excretion, with only a very small amount (0.5% of dose) found unchanged in urine. The glucuronide conjugate of tolcapone is mainly excreted in the urine but is also excreted in the bile.
Half Life: 2-3.5 hours
Clearance: 7 L/h
Toxicity: LD50 = 1600 mg/kg (Orally in rats)
Affected organisms: Humans and other mammals
Interactions
Drug interaction:
RasagilineTolcapone and Rasagiline decrease the metabolism of endogenous catecholamines. Concomitant therapy may result in increased catecholamine effects. Consider alternate therapy or use cautiously and monitor for increased catecholamine effects.
MoclobemideTolcapone and Moclobemide decrease the metabolism of endogenous catecholamines. Concomitant therapy may result in increased catecholamine effects. Consider alternate therapy or use cautiously and monitor for increased catecholamine effects.
TranylcypromineTolcapone and Tranylcypromine decrease the metabolism of endogenous catecholamines. Concomitant therapy may result in increased catecholamine effects. Consider alternate therapy or use cautiously and monitor for increased catecholamine effects.
IsocarboxazidTolcapone and Isocarboxazid decrease the metabolism of endogenous catecholamines. Concomitant therapy may result in increased catecholamine effects. Consider alternate therapy or use cautiously and monitor for increased catecholamine effects.
PhenelzineTolcapone and Phenelzine decrease the metabolism of endogenous catecholamines. Concomitant therapy may result in increased catecholamine effects. Consider alternate therapy or use cautiously and monitor for increased catecholamine effects.
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Enzymes