TCW

Tolcapone

Created:	2011-06-09
Last modified:	2021-03-13

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10 entries where TCW is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	31
Chiral Atom Count	0
Bond Count	32
Aromatic Bond Count	12

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Chemical Component Summary
Name	Tolcapone
Synonyms	(3,4-dihydroxy-5-nitrophenyl)(4-methylphenyl)methanone
Systematic Name (OpenEye OEToolkits)	(4-methylphenyl)-[3-nitro-4,5-bis(oxidanyl)phenyl]methanone
Formula	C₁₄ H₁₁ N O₅
Molecular Weight	273.241
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	[O-][N+](=O)c2cc(C(=O)c1ccc(cc1)C)cc(O)c2O
SMILES	CACTVS	3.370	Cc1ccc(cc1)C(=O)c2cc(O)c(O)c(c2)[N+]([O-])=O
SMILES	OpenEye OEToolkits	1.7.2	Cc1ccc(cc1)C(=O)c2cc(c(c(c2)O)O)[N+](=O)[O-]
Canonical SMILES	CACTVS	3.370	Cc1ccc(cc1)C(=O)c2cc(O)c(O)c(c2)[N+]([O-])=O
Canonical SMILES	OpenEye OEToolkits	1.7.2	Cc1ccc(cc1)C(=O)c2cc(c(c(c2)O)O)[N+](=O)[O-]
InChI	InChI	1.03	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	InChI	1.03	MIQPIUSUKVNLNT-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank ID	DB00323
Name	Tolcapone
Groups	approved withdrawn
Description	Tolcapone is a drug that inhibits the enzyme catechol-O-methyl transferase (COMT). It is used in the treatment of Parkinson's disease as an adjunct to levodopa/carbidopa medication. It is a yellow, odorless, non-hygroscopic, crystalline compound. Tolcapone is associated with a risk of hepatotoxicity.
Synonyms	Tolcapon (3,4-dihydroxy-5-nitrophenyl)(4-methylphenyl)methanone Tolcapone Tolcaponum 3,4-dihydroxy-5-nitro-4'-methylbenzophenone 3,4-dihydroxy-4'-methyl-5-nitrobenzophenone Tolcapona 4'-methyl-3,4-dihydroxy-5-nitrobenzophenone
Brand Names	Tasmar Tolcapone
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.
Categories	Anti-Dyskinesia Agents Anti-Parkinson Drugs Benzene Derivatives Benzophenones Central Nervous System Agents Central Nervous System Depressants COMT Inhibitors Cytochrome P-450 CYP2C9 Inhibitors Cytochrome P-450 CYP2C9 Inhibitors (strength unknown) Cytochrome P-450 Enzyme Inhibitors Dopamine Agents Drugs that are Mainly Renally Excreted Enzyme Inhibitors Hypotensive Agents Ketones Nervous System Nitro Compounds Nitrophenols Phenols
ATC-Code	N04BX01
CAS number	134308-13-7

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Catechol O-methyltransferase	MPEAPPLLLAAVLLGLVLLVVLLLLLRHWGWGLCLIGWNEFILQPIHNLL...	unknown	inhibitor
Cytochrome P450 2C9	MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...	unknown	inhibitor

Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682