Details of the Drug

General Information of Drug (ID: DMQ92WF)

Drug Name

GW 468816

Synonyms

GW468816; SCHEMBL5750612; CHEMBL1207366; (4e)-7-chloro-4-(2-oxo-1-phenyl-3-pyrrolidinylidene)-1,2,3,4-tetrahydro-2-quinolinecarboxylic acid

Indication

Disease Entry	ICD 11	Status	REF
Tobacco dependence	6C4A.2	Discontinued in Phase 2	[1]

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

368.8

Topological Polar Surface Area (xlogp)

3.3

Rotatable Bond Count (rotbonds)

2

Hydrogen Bond Donor Count (hbonddonor)

2

Hydrogen Bond Acceptor Count (hbondacc)

4

Chemical Identifiers

Formula: C20H17ClN2O3
IUPAC Name: (4E)-7-chloro-4-(2-oxo-1-phenylpyrrolidin-3-ylidene)-2,3-dihydro-1H-quinoline-2-carboxylic acid
Canonical SMILES: C\\1CN(C(=O)/C1=C/2\\CC(NC3=C2C=CC(=C3)Cl)C(=O)O)C4=CC=CC=C4
InChI: InChI=1S/C20H17ClN2O3/c21-12-6-7-14-16(11-18(20(25)26)22-17(14)10-12)15-8-9-23(19(15)24)13-4-2-1-3-5-13/h1-7,10,18,22H,8-9,11H2,(H,25,26)/b16-15+
InChIKey: XDKRVNKVAKCFGW-FOCLMDBBSA-N

Cross-matching ID

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Glycine receptor (GlyR)	TTZ8EM9	GLRA1_HUMAN; GLRA2_HUMAN; GLRA3_HUMAN; GLRA4_HUMAN; GLRB_HUMAN	Modulator	[2]

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Molecular Interaction Atlas (MIA)

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	Executive summary: nicotine addiction. Drugs Today (Barc). 2005 Jun;41(6):419-25.
2	A double-blind, placebo-controlled trial of the NMDA glycine site antagonist, GW468816, for prevention of relapse to smoking in females.J Clin Psychopharmacol.2011 Oct;31(5):597-602.
3	3-demethoxy-3-glycosylaminothiocolchicines: Synthesis of a new class of putative muscle relaxant compounds. J Med Chem. 2006 Sep 7;49(18):5571-7.
4	Neuroprotective potential of ionotropic glutamate receptor antagonists. Neurotox Res. 2002 Mar;4(2):119-26.
5	UK-315716/UK-240455. Pfizer. Curr Opin Investig Drugs. 2001 Dec;2(12):1737-9.
6	MDL 27,531 reduces spontaneous hindlimb contractions in rats with chronic transections of the spinal cord. Neurosci Lett. 1992 Nov 23;147(1):101-5.
7	Glycine antagonist (gavestinel) in neuroprotection (GAIN International) in patients with acute stroke: a randomised controlled trial.GAIN International Investigators.Lancet.2000 Jun 3;355(9219):1949-54.
8	First time in human for GV196771: interspecies scaling applied on dose selection. J Clin Pharmacol. 1999 Jun;39(6):560-6.
9	Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800003415)
10	Probing the pharmacophore of ginkgolides as glycine receptor antagonists. J Med Chem. 2007 Apr 5;50(7):1610-7.