Details of the Drug

General Information of Drug (ID: DMAIJSX)

Drug Name
L-701324
Synonyms
L-701324; 142326-59-8; L-701,324; L 701324; UNII-I9WY146163; C21H14ClNO3; L 701,324; CHEMBL31741; 7-Chloro-4-hydroxy-3-(3-phenoxy)phenyl-2(1H)-quinolone; I9WY146163; 7-Chloro-4-hydroxy-3-(3-pheoxyphenyl)-2(1H)-quinolinone; 2(1H)-Quinolinone, 7-chloro-4-hydroxy-3-(3-pheoxyphenyl)-; SMR000326934; compund 13 [PMID: 8182696]; Tocris-0907; AC1L3GJN; Biomol-NT_000206; MLS002153302; MLS000860076; GTPL4240; SCHEMBL1998890; BPBio1_001264; CHEBI:92140; DTXSID00162016; EX-A587; MolPort-003-941-887; 2(1H)-Quinolinone, 7-chloro-4-hydroxy-3-(3-ph
Indication
Disease Entry ICD 11 Status REF
Cerebrovascular ischaemia 8B1Z Terminated [1], [2], [3]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 363.8
Topological Polar Surface Area (xlogp) 4.5
Rotatable Bond Count (rotbonds) 3
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 3
Chemical Identifiers
Formula
C21H14ClNO3
IUPAC Name
7-chloro-4-hydroxy-3-(3-phenoxyphenyl)-1H-quinolin-2-one
Canonical SMILES
C1=CC=C(C=C1)OC2=CC=CC(=C2)C3=C(C4=C(C=C(C=C4)Cl)NC3=O)O
InChI
InChI=1S/C21H14ClNO3/c22-14-9-10-17-18(12-14)23-21(25)19(20(17)24)13-5-4-8-16(11-13)26-15-6-2-1-3-7-15/h1-12H,(H2,23,24,25)
InChIKey
FLVRDMUHUXVRET-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
54682505
ChEBI ID
CHEBI:92140
CAS Number
142326-59-8
TTD ID
D0M1WN

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Glutamate receptor ionotropic NMDA 1 (NMDAR1) TTLD29N NMDZ1_HUMAN Inhibitor [4]
Glutamate receptor ionotropic NMDA 2A (NMDAR2A) TTKJEMQ NMDE1_HUMAN Inhibitor [4]
Glutamate receptor ionotropic NMDA 2B (NMDAR2B) TTN9D8E NMDE2_HUMAN Inhibitor [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4240).
2 Anticonvulsant and behavioral profile of L-701,324, a potent, orally active antagonist at the glycine modulatory site on the N-methyl-D-aspartate receptor complex. J Pharmacol Exp Ther. 1996 Nov;279(2):492-501.
3 L-701,324, a selective antagonist at the glycine site of the NMDA receptor, counteracts haloperidol-induced muscle rigidity in rats. Psychopharmacology (Berl). 1999 Apr;143(3):235-43.
4 Synthesis of thieno[2,3-b]pyridinones acting as cytoprotectants and as inhibitors of [3H]glycine binding to the N-methyl-D-aspartate (NMDA) receptor. J Med Chem. 2006 Feb 9;49(3):864-71.
5 Glycine transport inhibitors for the treatment of schizophrenia: Symptom and disease modification. Curr Opin Drug Discov Devel. 2009 Jul;12(4):468-78.
6 Synthesis, ionotropic glutamate receptor binding affinity, and structure-activity relationships of a new set of 4,5-dihydro-8-heteroaryl-4-oxo-1,2,... J Med Chem. 2001 Sep 13;44(19):3157-65.
7 4,10-Dihydro-4-oxo-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-2-carboxylic acid derivatives: highly potent and selective AMPA receptors antagonists with... Bioorg Med Chem Lett. 2000 May 15;10(10):1133-7.
8 Bivalent beta-carbolines as potential multitarget anti-Alzheimer agents. J Med Chem. 2010 May 13;53(9):3611-7.
9 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 456).
10 Amino acid bioisosteres: design of 2-quinolone derivatives as glycine-site N-methyl-D-aspartate receptor antagonists, Bioorg. Med. Chem. Lett. 3(2):299-304 (1993).
11 Synthesis and evaluation of 6,11-ethanohexahydrobenzo[b]quinolizidines: a new class of noncompetitive N-methyl-D-aspartate antagonists. J Med Chem. 1995 Jun 23;38(13):2483-9.
12 Indeno[1,2-b]pyrazin-2,3-diones: a new class of antagonists at the glycine site of the NMDA receptor with potent in vivo activity. J Med Chem. 2000 Jun 15;43(12):2371-81.
13 How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
14 Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5.
15 4-Hydroxy-1-[2-(4-hydroxyphenoxy)ethyl]-4-(4-methylbenzyl)piperidine: a novel, potent, and selective NR1/2B NMDA receptor antagonist. J Med Chem. 1999 Jul 29;42(15):2993-3000.
16 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 455).
17 NMDA receptor stimulation induces reversible fission of the neuronal endoplasmic reticulum. PLoS One. 2009;4(4):e5250.
18 NMDA receptors as targets for drug action in neuropathic pain. Eur J Pharmacol. 2001 Oct 19;429(1-3):71-8.
19 Inhibition of in vivo [(3)H]MK-801 binding by NMDA receptor open channel blockers and GluN2B antagonists in rats and mice. Eur J Pharmacol. 2015 Nov 5;766:1-8.
20 Emerging drugs in neuropathic pain. Expert Opin Emerg Drugs. 2007 Mar;12(1):113-26.
21 Clinical pipeline report, company report or official report of Cadent Therapeutics.
22 Neu2000, an NR2B-selective, moderate NMDA receptor antagonist and potent spin trapping molecule for stroke. Drug News Perspect. 2010 Nov;23(9):549-56.
23 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)