Details of the Drug

General Information of Drug (ID: DM3YG5P)

Drug Name
GYKI-52466
Synonyms
Gyki-52466; 102771-26-6; GYKI 52466; UNII-471V8NZ5X3; GYKI 52466 HCl; CHEMBL275006; CHEBI:79560; 471V8NZ5X3; 1-(p-Aminophenyl)-4-methyl-7,8-methylenedioxy-5H-2,3-benzodiazepine hydrochloride; 4-(8-methyl-9h-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl)aniline; 4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine; Benzenamine,4-(8-methyl-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepin-5-yl)-; Benzenamine, 4-(8-methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)-; C17H15N3O2
Indication
Disease Entry ICD 11 Status REF
Alzheimer disease 8A20 Terminated [1], [2]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 293.32
Topological Polar Surface Area (xlogp) 2.3
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 5
Chemical Identifiers
Formula
C17H15N3O2
IUPAC Name
4-(8-methyl-9H-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl)aniline
Canonical SMILES
CC1=NN=C(C2=CC3=C(C=C2C1)OCO3)C4=CC=C(C=C4)N
InChI
InChI=1S/C17H15N3O2/c1-10-6-12-7-15-16(22-9-21-15)8-14(12)17(20-19-10)11-2-4-13(18)5-3-11/h2-5,7-8H,6,9,18H2,1H3
InChIKey
LFBZZHVSGAHQPP-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
3538
ChEBI ID
CHEBI:79560
CAS Number
102771-26-6
TTD ID
D0A9VO

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Glutamate receptor AMPA (GRIA) TTAN6JD NOUNIPROTAC Inhibitor [3]
Glutamate receptor AMPA 1 (GRIA1) TTVPQTF GRIA1_HUMAN Inhibitor [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Alzheimer disease
ICD Disease Classification 8A20
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Glutamate receptor AMPA 1 (GRIA1) DTT GRIA1 1.46E-06 -0.63 -0.78
Glutamate receptor AMPA (GRIA) DTT NO-GeName 1.79E-04 -0.69 -0.58
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression 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: 4210).
2 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800005470)
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6 Synthesis and AMPA receptor antagonistic activity of a novel 7-imidazolyl-6-trifluoromethyl quinoxalinecarboxylic acid with a substituted phenyl gr... Bioorg Med Chem Lett. 2004 Oct 18;14(20):5107-11.
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11 Synthesis of chiral 1-(2'-amino-2'-carboxyethyl)-1,4-dihydro-6,7-quinoxaline-2,3-diones: alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionate recep... J Med Chem. 1996 Oct 25;39(22):4430-8.
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 Reduced inhibition of cortical glutamate and GABA release by halothane in mice lacking the K+ channel, TREK-1. Br J Pharmacol. 2007 Nov;152(6):939-45.
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15 Eszopiclone: its use in the treatment of insomnia. Neuropsychiatr Dis Treat. 2007 Aug;3(4):441-453.
16 Effects of sevoflurane on carrageenan- and fentanyl-induced pain hypersensitivity in Sprague-Dawley rats. Can J Anaesth. 2009 Feb;56(2):126-35.
17 Enflurane directly depresses glutamate AMPA and NMDA currents in mouse spinal cord motor neurons independent of actions on GABAA or glycine receptors. Anesthesiology. 2000 Oct;93(4):1075-84.
18 Transmembrane residues define the action of isoflurane at the GABAA receptor alpha-3 subunit. Brain Res. 2005 Jan 25;1032(1-2):30-5.
19 Glutamatergic and GABAergic modulations of ultrasonic vocalizations during maternal separation distress in mouse pups. Psychopharmacology (Berl). 2009 May;204(1):61-71.
20 GABA(A) receptor ligands and their therapeutic potentials. Curr Top Med Chem. 2002 Aug;2(8):817-32.
21 Pharmacologic management of Alzheimer disease, Part II: Antioxidants, antihypertensives, and ergoloid derivatives. Ann Pharmacother. 1999 Feb;33(2):188-97.
22 Anaesthetic drugs: linking molecular actions to clinical effects. Curr Pharm Des. 2006;12(28):3665-79.