Page last updated: 2024-11-11

gavestinel

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Cross-References

ID SourceID
PubMed CID6450546
CHEMBL ID44793
CHEBI ID92867
SCHEMBL ID678632
SCHEMBL ID1721070
MeSH IDM0354467

Synonyms (38)

Synonym
BRD-K49890030-236-01-6
1h-indole-2-carboxylic acid, 4,6-dichloro-3-(3-oxo-3-(phenylamino)-1-propenyl)-, (e)-
1h-indole-2-carboxylic acid, 4,6-dichloro-3-((1e)-3-oxo-3-(phenylamino)-1-propenyl)-
gv 150526x
4,6-dichloro-3-((e)-2-(phenylcarbamoyl)vinyl)indole-2-carboxylic acid
gavestinel
(e)-4,6-dichloro-3-(3-oxo-3-(phenylamino)-1-propenyl)-1h-indole-2-carboxylic acid
153436-22-7
gavestinel (usan/inn)
D04308
gv-150526x
CHEMBL44793
3-[(e)-3-anilino-3-oxoprop-1-enyl]-4,6-dichloro-1h-indole-2-carboxylic acid
unii-318x4qy113
gavestinel [usan:inn:ban]
gv 150526
318x4qy113 ,
4,6-dichloro-3-[(1e)-3-oxo-3-(phenylamino)-1-propenyl]-1h-indole-2-carboxylic acid sodium salt
gavestinel [inn]
gavestinel [usan]
4,6-dichloro-3-[(e)-2-(phenylcarbamoyl)vinyl]indole-2-carboxylic acid
gavestinel [mart.]
e)-4,6-dichloro-3-(3-oxo-3-(phenylamino)-1-propenyl)-1h-indole-2-carboxylic acid
SCHEMBL678632
SCHEMBL1721070
bdbm50010475
CHEBI:92867
DB06741
(e)-4,6-dichloro-3-(3-oxo-3-(phenylamino)prop-1-enyl)-1h-indole-2-carboxylic acid
(e)3-[2-(phenylcarbamoyl)ethenyl]-4,6-dichloroindole-2-carboxylic acid
WZBNEZWCNKUOSM-VOTSOKGWSA-N
(e)-4,6-dichloro-3-(3-oxo-3-(phenylamino)prop-1-en-1-yl)-1h-indole-2-carboxylic acid
4,6-dichloro-3-[(1e)-3-oxo-3-(phenylamino)-1-propenyl]-1h-indole-2-carboxylicacidsodiumsalt
DTXSID90870012
4,6-dichloro-3-[(1e)-2-(phenylcarbamoyl)eth-1-en-1-yl]-1h-indole-2-carboxylic acid
(e)-4,6-dichloro-3-(3-oxo-3-(phenylamino)prop-1-en-1-yl)-1h-indole-2-carboxylicacid
CS-0612182
HY-150138

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
"Human pharmacokinetic parameters are often predicted prior to clinical study from in vivo preclinical pharmacokinetic data."( Extrapolation of human pharmacokinetic parameters from rat, dog, and monkey data: Molecular properties associated with extrapolative success or failure.
Jolivette, LJ; Ward, KW, 2005
)
0.33
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (18)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Bile salt export pumpHomo sapiens (human)IC50 (µMol)10.00000.11007.190310.0000AID1449628
Glutamate receptor 1Rattus norvegicus (Norway rat)IC50 (µMol)100.00000.00011.617910.0000AID92791
Glutamate receptor 2Rattus norvegicus (Norway rat)IC50 (µMol)100.00000.00011.700010.0000AID92791
Glutamate receptor 3Rattus norvegicus (Norway rat)IC50 (µMol)100.00000.00011.700010.0000AID92791
Glutamate receptor 4Rattus norvegicus (Norway rat)IC50 (µMol)100.00000.00011.700010.0000AID92791
Glutamate receptor ionotropic, kainate 1Rattus norvegicus (Norway rat)Ki100.00000.00071.71758.1800AID91449
Glutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)IC50 (µMol)0.00800.00071.600310.0000AID143473; AID241909
Glutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)Ki50.00150.00030.86666.6900AID143142; AID143774
Glutamate receptor ionotropic, kainate 2Rattus norvegicus (Norway rat)Ki100.00000.00370.80254.1000AID91449
Glutamate receptor ionotropic, kainate 3Rattus norvegicus (Norway rat)Ki100.00000.00380.79754.1000AID91449
Glutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)IC50 (µMol)0.00800.00071.630610.0000AID143473; AID241909
Glutamate receptor ionotropic, NMDA 2A Rattus norvegicus (Norway rat)Ki0.00300.00030.68056.6900AID143142
Glutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)IC50 (µMol)0.00800.00061.525710.0000AID143473; AID241909
Glutamate receptor ionotropic, NMDA 2BRattus norvegicus (Norway rat)Ki0.00300.00030.70716.6900AID143142
Glutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)IC50 (µMol)0.00800.00071.747210.0000AID143473; AID241909
Glutamate receptor ionotropic, NMDA 2CRattus norvegicus (Norway rat)Ki0.00300.00030.81966.6900AID143142
Glutamate receptor ionotropic, kainate 4Rattus norvegicus (Norway rat)Ki100.00000.00471.59194.1000AID91449
Uracil nucleotide/cysteinyl leukotriene receptorHomo sapiens (human)Ki1.63001.21003.03506.5400AID1137667
Glutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)IC50 (µMol)0.00800.00071.741110.0000AID143473; AID241909
Glutamate receptor ionotropic, NMDA 2DRattus norvegicus (Norway rat)Ki0.00300.00030.70726.6900AID143142
Glutamate receptor ionotropic, kainate 5Rattus norvegicus (Norway rat)Ki100.00000.01501.59454.1000AID91449
Glutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)IC50 (µMol)0.00800.00071.741110.0000AID143473; AID241909
Glutamate receptor ionotropic, NMDA 3BRattus norvegicus (Norway rat)Ki0.00300.00030.70726.6900AID143142
Glutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)IC50 (µMol)0.00800.00071.741110.0000AID143473; AID241909
Glutamate receptor ionotropic, NMDA 3ARattus norvegicus (Norway rat)Ki0.00300.00030.70726.6900AID143142
[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)
Glutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)Activity0.00700.00700.00850.0100AID145254
Glutamate receptor ionotropic, NMDA 1 Rattus norvegicus (Norway rat)Log Ki0.00850.00850.00850.0085AID143090
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (28)

Processvia Protein(s)Taxonomy
fatty acid metabolic processBile salt export pumpHomo sapiens (human)
bile acid biosynthetic processBile salt export pumpHomo sapiens (human)
xenobiotic metabolic processBile salt export pumpHomo sapiens (human)
xenobiotic transmembrane transportBile salt export pumpHomo sapiens (human)
response to oxidative stressBile salt export pumpHomo sapiens (human)
bile acid metabolic processBile salt export pumpHomo sapiens (human)
response to organic cyclic compoundBile salt export pumpHomo sapiens (human)
bile acid and bile salt transportBile salt export pumpHomo sapiens (human)
canalicular bile acid transportBile salt export pumpHomo sapiens (human)
protein ubiquitinationBile salt export pumpHomo sapiens (human)
regulation of fatty acid beta-oxidationBile salt export pumpHomo sapiens (human)
carbohydrate transmembrane transportBile salt export pumpHomo sapiens (human)
bile acid signaling pathwayBile salt export pumpHomo sapiens (human)
cholesterol homeostasisBile salt export pumpHomo sapiens (human)
response to estrogenBile salt export pumpHomo sapiens (human)
response to ethanolBile salt export pumpHomo sapiens (human)
xenobiotic export from cellBile salt export pumpHomo sapiens (human)
lipid homeostasisBile salt export pumpHomo sapiens (human)
phospholipid homeostasisBile salt export pumpHomo sapiens (human)
positive regulation of bile acid secretionBile salt export pumpHomo sapiens (human)
regulation of bile acid metabolic processBile salt export pumpHomo sapiens (human)
transmembrane transportBile salt export pumpHomo sapiens (human)
negative regulation of inflammatory response to antigenic stimulusUracil nucleotide/cysteinyl leukotriene receptorHomo sapiens (human)
G protein-coupled receptor signaling pathwayUracil nucleotide/cysteinyl leukotriene receptorHomo sapiens (human)
oligodendrocyte differentiationUracil nucleotide/cysteinyl leukotriene receptorHomo sapiens (human)
chemokine-mediated signaling pathwayUracil nucleotide/cysteinyl leukotriene receptorHomo sapiens (human)
positive regulation of Rho protein signal transductionUracil nucleotide/cysteinyl leukotriene receptorHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayUracil nucleotide/cysteinyl leukotriene receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (11)

Processvia Protein(s)Taxonomy
protein bindingBile salt export pumpHomo sapiens (human)
ATP bindingBile salt export pumpHomo sapiens (human)
ABC-type xenobiotic transporter activityBile salt export pumpHomo sapiens (human)
bile acid transmembrane transporter activityBile salt export pumpHomo sapiens (human)
canalicular bile acid transmembrane transporter activityBile salt export pumpHomo sapiens (human)
carbohydrate transmembrane transporter activityBile salt export pumpHomo sapiens (human)
ABC-type bile acid transporter activityBile salt export pumpHomo sapiens (human)
ATP hydrolysis activityBile salt export pumpHomo sapiens (human)
chemokine receptor activityUracil nucleotide/cysteinyl leukotriene receptorHomo sapiens (human)
receptor serine/threonine kinase bindingUracil nucleotide/cysteinyl leukotriene receptorHomo sapiens (human)
G protein-coupled receptor activityUracil nucleotide/cysteinyl leukotriene receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (13)

Processvia Protein(s)Taxonomy
basolateral plasma membraneBile salt export pumpHomo sapiens (human)
Golgi membraneBile salt export pumpHomo sapiens (human)
endosomeBile salt export pumpHomo sapiens (human)
plasma membraneBile salt export pumpHomo sapiens (human)
cell surfaceBile salt export pumpHomo sapiens (human)
apical plasma membraneBile salt export pumpHomo sapiens (human)
intercellular canaliculusBile salt export pumpHomo sapiens (human)
intracellular canaliculusBile salt export pumpHomo sapiens (human)
recycling endosomeBile salt export pumpHomo sapiens (human)
recycling endosome membraneBile salt export pumpHomo sapiens (human)
extracellular exosomeBile salt export pumpHomo sapiens (human)
membraneBile salt export pumpHomo sapiens (human)
plasma membraneGlutamate receptor 1Rattus norvegicus (Norway rat)
plasma membraneGlutamate receptor 2Rattus norvegicus (Norway rat)
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)
plasma membraneUracil nucleotide/cysteinyl leukotriene receptorHomo sapiens (human)
plasma membraneUracil nucleotide/cysteinyl leukotriene receptorHomo sapiens (human)
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 (24)

Assay IDTitleYearJournalArticle
AID540218Clearance in monkey after iv administration2005Journal of pharmaceutical sciences, Jul, Volume: 94, Issue:7
Extrapolation of human pharmacokinetic parameters from rat, dog, and monkey data: Molecular properties associated with extrapolative success or failure.
AID1449628Inhibition of human BSEP expressed in baculovirus transfected fall armyworm Sf21 cell membranes vesicles assessed as reduction in ATP-dependent [3H]-taurocholate transport into vesicles incubated for 5 mins by Topcount based rapid filtration method2012Drug metabolism and disposition: the biological fate of chemicals, Dec, Volume: 40, Issue:12
Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.
AID143768Compound was evaluated for its ability to displace [3H]-TCP binding to N-methyl-D-aspartate glutamate receptor 1. alpha value 0 indicates full antagonist.1998Journal of medicinal chemistry, Mar-12, Volume: 41, Issue:6
(E)-3-(2-(N-phenylcarbamoyl)vinyl)pyrrole-2-carboxylic acid derivatives. A novel class of glycine site antagonists.
AID241909Antagonist activity of compound against rat N-methyl-D-aspartate glutamate receptor using 11 nM [3H]glycine2005Journal of medicinal chemistry, Feb-24, Volume: 48, Issue:4
CoMFA, synthesis, and pharmacological evaluation of (E)-3-(2-carboxy-2-arylvinyl)-4,6-dichloro-1H-indole-2-carboxylic acids: 3-[2-(3-aminophenyl)-2-carboxyvinyl]-4,6-dichloro-1H-indole-2-carboxylic acid, a potent selective glycine-site NMDA receptor antag
AID419508Volume of distribution at steady state in human at 100 mg, iv2009Journal of medicinal chemistry, Jul-23, Volume: 52, Issue:14
In silico prediction of volume of distribution in human using linear and nonlinear models on a 669 compound data set.
AID92791Inhibition of binding of [3H]AMPA to Ionotropic glutamate receptor AMPA1998Journal of medicinal chemistry, Mar-12, Volume: 41, Issue:6
(E)-3-(2-(N-phenylcarbamoyl)vinyl)pyrrole-2-carboxylic acid derivatives. A novel class of glycine site 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.
AID1137667Displacement of [3H]PSB-12150 from human GPR17 expressed in CHO-K1 cell membranes after 60 mins by heterologous competition binding assay2014ACS medicinal chemistry letters, Apr-10, Volume: 5, Issue:4
Development of [(3)H]2-Carboxy-4,6-dichloro-1H-indole-3-propionic Acid ([(3)H]PSB-12150): A Useful Tool for Studying GPR17.
AID143090In vitro affinity of compound for the glycinergic site associated with NMDA receptor was assessed by inhibition of the binding of [3H]glycine1998Bioorganic & medicinal chemistry letters, Jul-07, Volume: 8, Issue:13
Unusual synthesis of new glycine antagonists via sequential aldol condensation-lactonization-elimination reaction.
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.
AID143767Inhibition of binding of [3H]glycine to N-methyl-D-aspartate glutamate receptor 1 from crude synaptic membranes prepared from adult rat cerebral cortex.1998Journal of medicinal chemistry, Mar-12, Volume: 41, Issue:6
(E)-3-(2-(N-phenylcarbamoyl)vinyl)pyrrole-2-carboxylic acid derivatives. A novel class of glycine site antagonists.
AID540214Clearance in rat after iv administration2005Journal of pharmaceutical sciences, Jul, Volume: 94, Issue:7
Extrapolation of human pharmacokinetic parameters from rat, dog, and monkey data: Molecular properties associated with extrapolative success or failure.
AID540221Volume of distribution at steady state in human after iv administration2005Journal of pharmaceutical sciences, Jul, Volume: 94, Issue:7
Extrapolation of human pharmacokinetic parameters from rat, dog, and monkey data: Molecular properties associated with extrapolative success or failure.
AID168591Anticonvulsant activity of compound was measured by the Number of rats protected / Number of rats tested at 10 mg/kg; 0/81997Journal 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.
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.
AID143142In vitro ability to inhibit the binding of [3H]glycine to glycine binding site of N-methyl-D-aspartate glutamate receptor in rat synaptic membranes2003Bioorganic & medicinal chemistry letters, Nov-03, Volume: 13, Issue:21
Enantiomerically pure tetrahydroquinoline derivatives as in vivo potent antagonists of the glycine binding site associated to the NMDA receptor.
AID145254Tested in vivo for affinity against glycine-binding site of NMDA receptor using [3H]DCKA radioligand1998Bioorganic & medicinal chemistry letters, Jan-06, Volume: 8, Issue:1
5-Aminomethylquinoxaline-2,3-diones. Part II: N-aryl derivatives as novel NMDA/glycine and AMPA antagonists.
AID540215Volume of distribution at steady state in rat after iv administration2005Journal of pharmaceutical sciences, Jul, Volume: 94, Issue:7
Extrapolation of human pharmacokinetic parameters from rat, dog, and monkey data: Molecular properties associated with extrapolative success or failure.
AID143774Compound was evaluated for its ability ot displace [3H]CPP binding to N-methyl-D-aspartate glutamate receptor 11998Journal of medicinal chemistry, Mar-12, Volume: 41, Issue:6
(E)-3-(2-(N-phenylcarbamoyl)vinyl)pyrrole-2-carboxylic acid derivatives. A novel class of glycine site antagonists.
AID91449Inhibition of binding of [3H]-kainic acid to Ionotropic glutamate receptor kainate1998Journal of medicinal chemistry, Mar-12, Volume: 41, Issue:6
(E)-3-(2-(N-phenylcarbamoyl)vinyl)pyrrole-2-carboxylic acid derivatives. A novel class of glycine site antagonists.
AID540216Clearance in dog after iv administration2005Journal of pharmaceutical sciences, Jul, Volume: 94, Issue:7
Extrapolation of human pharmacokinetic parameters from rat, dog, and monkey data: Molecular properties associated with extrapolative success or failure.
AID540217Volume of distribution at steady state in dog after iv administration2005Journal of pharmaceutical sciences, Jul, Volume: 94, Issue:7
Extrapolation of human pharmacokinetic parameters from rat, dog, and monkey data: Molecular properties associated with extrapolative success or failure.
AID540219Volume of distribution at steady state in monkey after iv administration2005Journal of pharmaceutical sciences, Jul, Volume: 94, Issue:7
Extrapolation of human pharmacokinetic parameters from rat, dog, and monkey data: Molecular properties associated with extrapolative success or failure.
AID540220Clearance in human after iv administration2005Journal of pharmaceutical sciences, Jul, Volume: 94, Issue:7
Extrapolation of human pharmacokinetic parameters from rat, dog, and monkey data: Molecular properties associated with extrapolative success or failure.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's4 (40.00)18.2507
2000's4 (40.00)29.6817
2010's2 (20.00)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: 19.61

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index19.61 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index4.37 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (19.61)

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%
Other10 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]