Compound: Tivantinib
SMILES: O=C1NC(=O)[C@H]([C@@H]1c2c3c4c(ccc3)CCCn4c2)c5c6c(cccc6)[nH]c5
InChIKey: UCEQXRCJXIVODC-PMACEKPBSA-N
Synonyms: Tivantinib, 905854-02-6, ARQ-197, (3R,4R)-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione, ARQ 197, ARQ197, PJ4H73IL17, DTXSID60920316, (3R,4R)-3-(5,6-Dihydro-4H-pyrrolo(3,2,1-ij)quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione, tivantinibum, RefChem:898517, c-Met Inhibitor ARQ 197, DTXCID301349230, (3R,4R)-3-(1-azatricyclo(6.3.1.0^(4,12))dodeca-2,4,6,8(12)-tetraen-3-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione, Tivantinib (ARQ 197), (rel)-Tivantinib, 905853-99-8, rel-(3R,4R)-3-(5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-2,5-pyrrolidinedione, MFCD11977597, 1000873-98-2, (3R,4R)-3-(1-azatricyclo[6.3.1.04,12]dodeca-2,4,6,8(12)-tetraen-3-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione, Tivantinib [INN], Tivantinib [USAN:INN], UNII-PJ4H73IL17, Tivantinib; ARQ197, TIVANTINIB [MI], TIVANTINIB [JAN], TIVANTINIB [USAN], ARQ 197 (Tivantinib), TIVANTINIB [WHO-DD], SCHEMBL44944, orb322231, Tivantinib (JAN/USAN/INN), GTPL7948, orb1301058, orb1941247, CHEMBL2103882, SCHEMBL29355700, CHEBI:91398, UCEQXRCJXIVODC-PMACEKPBSA-N, ARQ-197,Tivantinib, ARQ197, ARQ197; ARQ-197;Tivantinib, GLXC-90217, CS-M1640, EX-A2169, CAS:905854-02-6;Tivantinib, BDBM50146168, NSC758242, NSC800951, s2753, AKOS022182739, CCG-268285, DB12200, EBC-218037, FT44530, NSC-758242, NSC-800951, SDCCGSBI-0654487.P001, (-)-trans-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione, 2,5-Pyrrolidinedione, 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-, (3R,4R)-rel-, AC-25009, AC-35963, AS-16991, DA-67145, DA-68209, HY-50686, HY-77493, DB-362059, NS00073191, C77073, D10173, E82820, BRD-K33379087-001-01-8, BRD-K33379087-001-07-5, Q17123902, Z2242166213, (+/-)-trans-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4(1H-indol-3-yl)pyrrolidine-2,5-dione, (+/-)-trans-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl) pyrrolidine-2,5-dione, (+/-)-trans-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione, (_)-trans-3-(5,6-dihydro-4h-pyrrolo[3,2,1-ij]quinolin-1-yl)-4(1h-indol-3-yl)pyrrolidine-2,5-dione, (3R,4R)-3-(2,3-dihydro-1H-pyrrolo[3,2,1-ij]quinolin-6-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione, (3R,4R)-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-pyrrolidine-2,5-dione, (3R,4R)-3-(5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione; ARQ 197;, 2,5-Pyrrolidinedione, 3-(5,6-dihydro-4H-pyrrolo(3,2,1-ij)quinolin-1-yl)-4-(1H-indol-3-yl)-, (3R,4R)-, TIV, trans 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-pyrrolidine-2,5-dione
Theoretical properties:
molecular_formula: C23H19N3O2
molecular_weight: 369.4 g/mol
exact_mass: 369.147726857 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 2
heavy_atom_count: 28
topological_polar_surface_area: 66.9 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: LSM-1131 is a member of indoles.
chembl: TIVANTINIB is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.
wikipedia: Tivantinib (ARQ197; by Arqule, Inc.) is an experimental small molecule anti-cancer drug. It is a bisindolylmaleimide that binds to the dephosphorylated MET kinase in vitro. (MET is a growth factor receptor.) Tivantinib is being tested clinically as a highly selective MET inhibitor. However, the mechanism of action of tivantinib is still unclear.
Tivantinib displays cytotoxic activity via molecular mechanisms that are independent from its ability to bind MET, notably tubulin binding, which likely underlies tivantinib cytotoxicity.
Possible applications include non-small-cell lung carcinoma, hepatocellular carcinoma, and oesophageal cancer.
In 2017, it was announced that a phase III clinical trial for advanced hepatocellular carcinoma had failed to meet the primary endpoint.