Structure via PubChem · Public domain (PubChem)
tolcapone
Sign in to saveAlso known as Ro 40-7592, Ro-407592, Tasmar®, 3,4-dihydroxy-4'-methyl-5-nitrobenzophenone, 3,4-dihydroxy-5-nitro-4'-methylbenzophenone, 4'-methyl-3,4-dihydroxy-5-nitrobenzophenone, 4'-Methyl-3,4-dihydroxy-5-nitrobenzophenone, (3,4-dihydroxy-5-nitrophenyl)(4-methylphenyl)methanone
Tolcapone, sold under the brand name Tasmar, is a medication used to treat Parkinson's disease (PD). It is a selective, potent and reversible nitrocatechol-type inhibitor of the enzyme catechol-O-methyltransferase (COMT). It has demonstrated significant liver toxicity, which has led to suspension of marketing authorisations in a number of countries.
In the Vinony graph
Vinony's link graph records 264 inbound references to tolcapone, and connects out to L-tyrosine, clinical trial and catechol-O-methyltransferase.
Vinony files it under 4-Tolyl compounds, Antiparkinsonian agents and Benzophenones.
Vinony links it to 17 Wikipedia language editions.
Key facts
- Drug.legal_AU
- S4
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 470611468
- Drug.image
- Tolcapone.svg
- Drug.image_class
- skin-invert-image
- Drug.image2
- Tolcapone3d.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Tasmar
- Drug.MedlinePlus
- a698036
- Drug.DailyMedID
- Tolcapone
- Drug.pregnancy_AU
- B3
- Drug.licence_EU
- yes
- Drug.legal_BR
- C1
- Drug.legal_UK
- POM
- Drug.legal_US
- Rx-only
- Drug.legal_EU
- Rx-only
- Drug.routes_of_administration
- By mouth
- Drug.ATC_prefix
- N04
via Wikipedia infobox
Chemical data
- Formula
- C14H11NO5
- Molecular weight
- 273.24 g/mol
- IUPAC name
- (3,4-dihydroxy-5-nitrophenyl)-(4-methylphenyl)methanone
- SMILES
- CC1=CC=C(C=C1)C(=O)C2=CC(=C(C(=C2)O)O)[N+](=O)[O-]
- InChIKey
- MIQPIUSUKVNLNT-UHFFFAOYSA-N
- XLogP
- 3.3
- Polar surface area
- 103 Ų
- H-bond donors
- 2
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
Withdrawn- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1997
- Admin. routes
- oral
- Indications
- nicotine dependence, gambling behaviour, Pick disease, neuroblastoma
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 273.064
- Has use
- medication
Show 9 more facts
- subject has role
- enzyme inhibitor
- chemical formula
- C₁₄H₁₁NO₅
- World Health Organisation international non-proprietary name
- tolcapone
- medical condition treated
- Parkinson's disease
- canonical SMILES
- CC1=CC=C(C=C1)C(=O)C2=CC(=C(C(=C2)O)O)[N+](=O)[O-]
- defined daily dose
- 0.45
- Commons category
- Tolcapone
- legal status (medicine)
- boxed warning
- significant drug interaction
- phenelzine
via Wikidata · CC0
~11 min read
Encyclopedic overview
15 sectionsContents
- Medical uses
- Contraindications
- Side effects
- Interactions
- Pharmacology
- Mechanism of action
- Pharmacokinetics
- Chemistry
- Synthesis
- History
- Research
- Transthyretin amyloidosis
- Psychiatric disorders
- References
- External links
Tolcapone, sold under the brand name Tasmar, is a medication used to treat Parkinson's disease (PD). It is a selective, potent and reversible nitrocatechol-type inhibitor of the enzyme catechol-O-methyltransferase (COMT). It has demonstrated significant liver toxicity, which has led to suspension of marketing authorisations in a number of countries.
Tolcapone appears to be peripherally selective, but can still cross into the brain in significant amounts and has been found to inhibit COMT centrally as well. In comparison with entacapone, another nitrocatechol COMT inhibitor, tolcapone has a longer half life (2.9 hours vs. 0.8 hours) and can better penetrate into the brain, acting both in the central nervous system and in the periphery. However, entacapone is less toxic for the liver.
Excerpted from Wikipedia’s “tolcapone” article, available under the CC BY-SA 4.0 licence.