Compound: Tolcapone
SMILES: O=[N+]([O-])c1c(O)c(O)cc(c1)C(=O)c2ccc(C)cc2
InChIKey: MIQPIUSUKVNLNT-UHFFFAOYSA-N
Synonyms: Tolcapone, 134308-13-7, Tasmar, 3,4-Dihydroxy-4'-methyl-5-nitrobenzophenone, Ro 40-7592, (3,4-Dihydroxy-5-nitrophenyl)(4-methylphenyl)methanone, Ro-40-7592, (3,4-dihydroxy-5-nitrophenyl)-(4-methylphenyl)methanone, Methanone, (3,4-dihydroxy-5-nitrophenyl)(4-methylphenyl)-, Tolcapona, DTXSID3023685, CIF6334OLY, Ro-407592, 5-(4-methylbenzoyl)-3-nitrobenzene-1,2-diol, DTXCID903685, 3,4-dihydroxy-5-nitro-4'-methylbenzophenone, 4'-methyl-3,4-dihydroxy-5-nitrobenzophenone, CHEBI:63630, 5-((4-methylphenyl)carbonyl)-3-nitrobenzene-1,2-diol, Tolcaponum, 5-[(4-METHYLPHENYL)CARBONYL]-3-NITROBENZENE-1,2-DIOL, Ro407592, Ro 407592, Methanone,(3,4-dihydroxy-5-nitrophenyl)(4-methylphenyl)-, Ro 40 7592, RefChem:57103, 3,4 Dihydroxy 5' methyl 5 nitrobenzophenone, N04BX01, (3,4-dihydroxy-5-nitrophenyl)(p-tolyl)methanone, MFCD00866569, CHEMBL1324, s4021, NCGC00181767-01, 3,4-dihydroxy-4 inverted exclamation mark -methyl-5-nitrobenzophenone, Talcapone, UNII-CIF6334OLY, Tasmar (TN), CCRIS 7904, CAS-134308-13-7, Tolcapone?, MIQPIUSUKVNLNT-UHFFFAOYSA-N, Tolcapone [USAN:USP:INN:BAN], TCW, (3,4-dihydroxy-5-nitro-phenyl)-(p-tolyl)methanone, Tolcapone (Standard), TOLCAPONE [INN], TOLCAPONE [JAN], TOLCAPONE [MI], TOLCAPONE [USAN], TOLCAPONE [VANDF], TOLCAPONE [MART.], TOLCAPONE [USP-RS], TOLCAPONE [WHO-DD], Tolcapone (JAN/USP/INN), SCHEMBL33869, TOLCAPONE [EMA EPAR], MLS006012044, BIDD:GT0032, Tolcapone - Bio-X trade mark, GTPL6646, orb1300535, TOLCAPONE [ORANGE BOOK], SCHEMBL29360457, Tolcapone, >=98% (HPLC), TOLCAPONE [USP MONOGRAPH], 3s68, GLXC-07383, HMS2089K14, HMS3652M17, HMS3715D16, HMS3872F03, HMS3885G18, HMS5082J17, Tox21_112963, Tox21_302414, AC-791, ARD193222, BDBM50108877, EBC-26395, HY-17406R, AKOS015902328, Tox21_112963_1, AS-7085, CCG-221217, CS-1173, DB00323, FT28305, KS-1314, NCGC00181767-02, NCGC00181767-03, NCGC00255188-01, BT164481, HY-17406, SMR001614567, SY102278, DB-013561, NS00007380, SW219511-1, T3856, C07949, D00786, O10068, SBI-0654149.0001, AB01275441-01, AB01275441_02, (3,4-Dihydroxy-5-nitro-phenyl)-p-tolyl-methanone, EN300-18567526, Q413840, SR-05000001444, SR-05000001444-1, BRD-K10852020-001-01-1, BRD-K10852020-001-04-5, BRD-K10852020-001-05-2, Tolcapone, United States Pharmacopeia (USP) Reference Standard, InChI=1/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,1H
Theoretical properties:
molecular_formula: C14H11NO5
molecular_weight: 273.24 g/mol
exact_mass: 273.06372245 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 2
heavy_atom_count: 20
topological_polar_surface_area: 103 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
solubility: 5.69e-02 g/L
Descriptions:
pubchem: Tolcapone is benzophenone substituted on one of the phenyl rings at C-3 and C-4 by hydroxy groups and at C-5 by a nitro group, and on the other phenyl ring by a methyl group at C-4. It is an inhibitor of catechol O-methyltransferase. It has a role as an EC 2.1.1.6 (catechol O-methyltransferase) inhibitor and an antiparkinson drug. It is a member of benzophenones, a member of catechols and a member of 2-nitrophenols.
chebi: Benzophenone substituted on one of the phenyl rings at C-3 and C-4 by hydroxy groups and at C-5 by a nitro group, and on the other phenyl ring by a methyl group at C-4. It is an inhibitor of catechol <em>O</em>-methyltransferase.
chembl: TOLCAPONE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: 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.