Compounds > mdl 104653
Page last updated: 2024-11-13

mdl 104653

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Description

3-phenyl-4-hydroxy-7-chloroquinolin-2(1H)-one: an NMDA/glycine site antagonist; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID54697468
CHEMBL ID31661
SCHEMBL ID1612505
MeSH IDM0247449

Synonyms (22)

Synonym
7-chloro-4-hydroxy-3-phenyl-1h-quinolin-2-one
7-chloro-4-hydroxy-3-phenylquinolin-2(1h)-one
bdbm50041467
7-chloro-4-hydroxy-3-phenyl-2(1h)-quinolinone
28563-19-1
CHEMBL31661 ,
l-698532
mdl-104653
mdl 104,653
3-phenyl-4-hydroxy-7-chloroquinolin-2(1h)-one
mdl-104,653
2(1h)-quinolinone, 7-chloro-4-hydroxy-3-phenyl-
SCHEMBL1612505
7-chloro-4-hydroxy-3-phenyl-2(1h)-quinolone
RDXQSWLUXKUQSI-UHFFFAOYSA-N
DTXSID80182777
3-phenyl-4-hydroxy-7-chloro-quinolin-2(1h)-one
7-chloro-4-hydroxy-3-phenyl-1,2-dihydroquinolin-2-one
AS-67237
AKOS032961557
BCP18252
D92977
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (14)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Glutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)IC50 (µMol)0.17070.00071.600310.0000AID143068; AID143473; AID143608
Glutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)IC50 (µMol)0.17200.00071.630610.0000AID143473
Glutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)IC50 (µMol)0.17200.00061.525710.0000AID143473
Glutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)IC50 (µMol)0.17200.00071.747210.0000AID143473
Glutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)IC50 (µMol)0.17200.00071.741110.0000AID143473
Glutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)IC50 (µMol)0.17200.00071.741110.0000AID143473
Glutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)IC50 (µMol)0.17200.00071.741110.0000AID143473
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Alpha-1B adrenergic receptorRattus norvegicus (Norway rat)Kb0.88000.02800.45400.8800AID196564
Alpha-1D adrenergic receptorRattus norvegicus (Norway rat)Kb0.88000.01180.30660.8800AID196564
Vasopressin V1a receptorRattus norvegicus (Norway rat)Kb0.88000.02800.45400.8800AID196564
Sodium-dependent serotonin transporterRattus norvegicus (Norway rat)Kb0.88000.02800.45400.8800AID196564
Glutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)Kb0.88000.00592.09697.0000AID196564
Alpha-1A adrenergic receptorRattus norvegicus (Norway rat)Kb0.88000.00040.30280.8800AID196564
Vasopressin V1b receptorRattus norvegicus (Norway rat)Kb0.88000.02800.45400.8800AID196564
Vasopressin V2 receptor Rattus norvegicus (Norway rat)Kb0.88000.02800.45400.8800AID196564
Glutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)Kb0.88000.00592.41137.0000AID196564
Glutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)Kb0.88000.00592.41137.0000AID196564
Glutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)Kb0.88000.00592.41137.0000AID196564
Glutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)Kb0.88000.00592.41137.0000AID196564
Glutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)Kb0.88000.00592.41137.0000AID196564
Glutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)Kb0.88000.00592.41137.0000AID196564
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)
endoplasmic reticulum membraneGlutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)
plasma membraneGlutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (13)

Assay IDTitleYearJournalArticle
AID112401compound was evaluated in vivo for their ability to protect against audiogenic seizure in DBA/2 mice when dosed ip 30 min prior to noise stimulation and it is evaluated as ED50 value1997Journal of medicinal chemistry, Feb-28, Volume: 40, Issue:5
4-substituted-3-phenylquinolin-2(1H)-ones: acidic and nonacidic glycine site N-methyl-D-aspartate antagonists with in vivo activity.
AID143068Inhibition of the binding of [3H]L-689,560 ([3H]-4) to the strychnine-insensitive glycine site on rat brain membranes1994Journal of medicinal chemistry, May-13, Volume: 37, Issue:10
3'-(Arylmethyl)- and 3'-(aryloxy)-3-phenyl-4-hydroxyquinolin-2(1H)-ones: orally active antagonists of the glycine site on the NMDA receptor.
AID143608In vitro ability to displace [3H]L-689,560 binding to glycine site on the N-methyl-D-aspartate (NMDA) glutamate receptor 1 from rat cortical membranes1997Journal of medicinal chemistry, Feb-28, Volume: 40, Issue:5
4-substituted-3-phenylquinolin-2(1H)-ones: acidic and nonacidic glycine site N-methyl-D-aspartate antagonists with in vivo activity.
AID226501protein binding index(PBI) is the ratio of binding affinities for the displacement of [3H]- glycine from rat cortical membranes in the presence and absence of 0.2% human serum albumin1997Journal of medicinal chemistry, Dec-05, Volume: 40, Issue:25
Effect of plasma protein binding on in vivo activity and brain penetration of glycine/NMDA receptor antagonists.
AID186995Blockade of NMDA-induced depolarizations on rat cortical slices1994Journal of medicinal chemistry, May-13, Volume: 37, Issue:10
3'-(Arylmethyl)- and 3'-(aryloxy)-3-phenyl-4-hydroxyquinolin-2(1H)-ones: orally active antagonists of the glycine site on the NMDA receptor.
AID19623Partition coefficient (logP)1997Journal of medicinal chemistry, Dec-05, Volume: 40, Issue:25
Effect of plasma protein binding on in vivo activity and brain penetration of glycine/NMDA receptor antagonists.
AID131549Protection from audiogenic seizure in the DBA/2 mouse 30 min after intraperitoneal administration1994Journal of medicinal chemistry, May-13, Volume: 37, Issue:10
3'-(Arylmethyl)- and 3'-(aryloxy)-3-phenyl-4-hydroxyquinolin-2(1H)-ones: orally active antagonists of the glycine site on the NMDA receptor.
AID113264Anti convulsant activity of compound was measured by its ability to protect against audiogenic seizure in DBA/2 mice when dosed intraperitoneally 30 min prior to seizure induction.1997Journal of medicinal chemistry, Dec-05, Volume: 40, Issue:25
Effect of plasma protein binding on in vivo activity and brain penetration of glycine/NMDA receptor antagonists.
AID259801Inhibition of [3H]glycine binding to NMDA receptor in rat brain membranes2006Journal of medicinal chemistry, Feb-09, Volume: 49, Issue:3
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.
AID131550Protection from audiogenic seizure in the DBA/2 mouse 30 min after oral administration1994Journal of medicinal chemistry, May-13, Volume: 37, Issue:10
3'-(Arylmethyl)- and 3'-(aryloxy)-3-phenyl-4-hydroxyquinolin-2(1H)-ones: orally active antagonists of the glycine site on the NMDA receptor.
AID196564Evaluated to antagonize NMDA responses in a rat cortical slice preparations1997Journal of medicinal chemistry, Feb-28, Volume: 40, Issue:5
4-substituted-3-phenylquinolin-2(1H)-ones: acidic and nonacidic glycine site N-methyl-D-aspartate antagonists with in vivo activity.
AID203505Human serum albumin index was measured by retention time on an HPLC column containing human albumin1997Journal of medicinal chemistry, Dec-05, Volume: 40, Issue:25
Effect of plasma protein binding on in vivo activity and brain penetration of glycine/NMDA receptor antagonists.
AID143473Affinity for the glycine binding site on rat N-methyl-D-aspartate glutamate receptor 1, determined by displacement of the glycine site antagonist [3H]L-689,560 from rat cortical membranes1997Journal of medicinal chemistry, Dec-05, Volume: 40, Issue:25
Effect of plasma protein binding on in vivo activity and brain penetration of glycine/NMDA receptor antagonists.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's4 (80.00)18.2507
2000's1 (20.00)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.40

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.40 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.20 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.40)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
5,7-dichlorokynurenic acid
5,7-dichlorokynurenic acid: potent antagonist at the N-methyl-D-aspartate receptor-associated glycine binding site		1.9910quinolines
7-chlorokynurenic acid
7-chlorokynurenic acid: selective antagonist at the glycine modulatory site of the N-methyl-D-aspartate receptor complex; structure given in first source. 7-chlorokynurenic acid : A quinolinemonocarboxylic acid that is quinaldic acid which is substituted by a hydroxy group at position 4 and by a chlorine at position 7. It is a potent NMDA glutamate receptor antagonist which antagonizes the strychnine-insensitive glycine site of the NMDA receptor. It also prevents neurodegeneration produced by quinolinic acid.		1.9910organochlorine compound;
quinolinemonocarboxylic acid		neuroprotective agent;
NMDA receptor antagonist
diazepam
Diazepam: A benzodiazepine with anticonvulsant, anxiolytic, sedative, muscle relaxant, and amnesic properties and a long duration of action. Its actions are mediated by enhancement of GAMMA-AMINOBUTYRIC ACID activity.. diazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a methyl group at position 1 and a phenyl group at position 5.		1.99101,4-benzodiazepinone;
organochlorine compound		anticonvulsant;
anxiolytic drug;
environmental contaminant;
sedative;
xenobiotic
carbostyril
Quinolones: A group of derivatives of naphthyridine carboxylic acid, quinoline carboxylic acid, or NALIDIXIC ACID.. quinolin-2(1H)-one : A quinolone that is 1,2-dihydroquinoline substituted by an oxo group at position 2.		1.9810monohydroxyquinoline;
quinolone		bacterial xenobiotic metabolite
mdl29,951
[no description available]		1.9810
licostinel
licostinel: a glycine site NMDA receptor antagonist; structure given in first source		1.9910
gavestinel
[no description available]		1.9910
l 689560
[no description available]		1.9810quinolines
l 701324
L 701324: a glycine/NMDA receptor antagonist		2.9140quinolines
7-chloro-3-[cyclopropyl(oxo)methyl]-4-hydroxy-1H-quinolin-2-one
[no description available]		1.9910hydroxyquinoline;
quinolone
ConditionIndicatedRelationship StrengthStudiesTrials
Absence Seizure
[description not available]		02.4120
Seizures
Clinical or subclinical disturbances of cortical function due to a sudden, abnormal, excessive, and disorganized discharge of brain cells. Clinical manifestations include abnormal motor, sensory and psychic phenomena. Recurrent seizures are usually referred to as EPILEPSY or seizure disorder.		07.4120