Page last updated: 2024-11-07

4-amino-n-(2,6-dimethylphenyl)phthalimide

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

Description

4-amino-N-(2,6-dimethylphenyl)phthalimide: a potent anticonvulsant against maximal electroshock-induced seizures; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID124031
CHEMBL ID283880
SCHEMBL ID4151437
MeSH IDM0252477

Synonyms (15)

Synonym
158276-70-1
5-amino-2-(2,6-dimethylphenyl)isoindoline-1,3-dione
4-amino-n-(2,6-dimethylphenyl)phthalimide
CHEMBL283880 ,
add 213063
5-amino-2-(2,6-dimethylphenyl)isoindole-1,3-dione
bdbm50066438
5-amino-2-(2,6-dimethyl-phenyl)-isoindole-1,3-dione
5-amino-2-(2,6-dimethylphenyl)-1h-isoindole-1,3(2h)-dione
add-213063
1h-isoindole-1,3(2h)-dione, 5-amino-2-(2,6-dimethylphenyl)-
URALYBWTMWGVCV-UHFFFAOYSA-N
SCHEMBL4151437
DTXSID20166394
5-amino-2-(2,6-dimethylphenyl)-2,3-dihydro-1h-isoindole-1,3-dione

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" This anti-MES activity is achieved with nontoxic doses, with the optimal effect recorded in rats dosed orally with anti-MES ED50 and protective index (PI) values of 25."( Comparative anticonvulsant activity and neurotoxicity of 4-amino-N-(2,6-dimethylphenyl)phthalimide and prototype antiepileptic drugs in mice and rats.
Bailleux, V; Hamoir, G; Nuyts, JP; Poupaert, JH; Stables, JP; Vallée, L; Vamecq, J, 1995
)
0.54
" Anticonvulsant ED50s (effective doses in at least 50% of animals tested) of compounds in the MES test were determined in rats dosed orally and amounted to 52 (1), 135 (2), 284 (3), 231 (8), 131 (9), 25 (10), 369 (13), 354 (14), and 121 (PHT) micromol/kg, compound 5 presenting with an ED50 value higher than 650 micromol/kg."( Anticonvulsant activity and interactions with neuronal voltage-dependent sodium channel of analogues of ameltolide.
Lambert, D; Masereel, B; Poupaert, JH; Stables, JP; Vamecq, J, 1998
)
0.3
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Aminopeptidase NHomo sapiens (human)IC50 (µMol)56.30000.40002.11003.9000AID38364
Aminopeptidase NSus scrofa (pig)IC50 (µMol)56.30000.00053.53548.9000AID38364
Dipeptidyl peptidase 4Homo sapiens (human)IC50 (µMol)87.90000.00010.444410.0000AID56226
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (23)

Processvia Protein(s)Taxonomy
angiogenesisAminopeptidase NHomo sapiens (human)
cell differentiationAminopeptidase NHomo sapiens (human)
symbiont entry into host cellAminopeptidase NHomo sapiens (human)
proteolysisAminopeptidase NHomo sapiens (human)
peptide catabolic processAminopeptidase NHomo sapiens (human)
behavioral fear responseDipeptidyl peptidase 4Homo sapiens (human)
response to hypoxiaDipeptidyl peptidase 4Homo sapiens (human)
proteolysisDipeptidyl peptidase 4Homo sapiens (human)
cell adhesionDipeptidyl peptidase 4Homo sapiens (human)
positive regulation of cell population proliferationDipeptidyl peptidase 4Homo sapiens (human)
negative regulation of extracellular matrix disassemblyDipeptidyl peptidase 4Homo sapiens (human)
peptide hormone processingDipeptidyl peptidase 4Homo sapiens (human)
receptor-mediated endocytosis of virus by host cellDipeptidyl peptidase 4Homo sapiens (human)
T cell costimulationDipeptidyl peptidase 4Homo sapiens (human)
regulation of cell-cell adhesion mediated by integrinDipeptidyl peptidase 4Homo sapiens (human)
locomotory exploration behaviorDipeptidyl peptidase 4Homo sapiens (human)
psychomotor behaviorDipeptidyl peptidase 4Homo sapiens (human)
T cell activationDipeptidyl peptidase 4Homo sapiens (human)
endothelial cell migrationDipeptidyl peptidase 4Homo sapiens (human)
symbiont entry into host cellDipeptidyl peptidase 4Homo sapiens (human)
receptor-mediated virion attachment to host cellDipeptidyl peptidase 4Homo sapiens (human)
negative chemotaxisDipeptidyl peptidase 4Homo sapiens (human)
membrane fusionDipeptidyl peptidase 4Homo sapiens (human)
negative regulation of neutrophil chemotaxisDipeptidyl peptidase 4Homo sapiens (human)
glucagon processingDipeptidyl peptidase 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (16)

Processvia Protein(s)Taxonomy
virus receptor activityAminopeptidase NHomo sapiens (human)
aminopeptidase activityAminopeptidase NHomo sapiens (human)
metallopeptidase activityAminopeptidase NHomo sapiens (human)
signaling receptor activityAminopeptidase NHomo sapiens (human)
metalloaminopeptidase activityAminopeptidase NHomo sapiens (human)
zinc ion bindingAminopeptidase NHomo sapiens (human)
peptide bindingAminopeptidase NHomo sapiens (human)
virus receptor activityDipeptidyl peptidase 4Homo sapiens (human)
protease bindingDipeptidyl peptidase 4Homo sapiens (human)
aminopeptidase activityDipeptidyl peptidase 4Homo sapiens (human)
serine-type endopeptidase activityDipeptidyl peptidase 4Homo sapiens (human)
signaling receptor bindingDipeptidyl peptidase 4Homo sapiens (human)
protein bindingDipeptidyl peptidase 4Homo sapiens (human)
serine-type peptidase activityDipeptidyl peptidase 4Homo sapiens (human)
dipeptidyl-peptidase activityDipeptidyl peptidase 4Homo sapiens (human)
identical protein bindingDipeptidyl peptidase 4Homo sapiens (human)
protein homodimerization activityDipeptidyl peptidase 4Homo sapiens (human)
chemorepellent activityDipeptidyl peptidase 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (18)

Processvia Protein(s)Taxonomy
extracellular spaceAminopeptidase NHomo sapiens (human)
lysosomal membraneAminopeptidase NHomo sapiens (human)
endoplasmic reticulum-Golgi intermediate compartmentAminopeptidase NHomo sapiens (human)
plasma membraneAminopeptidase NHomo sapiens (human)
external side of plasma membraneAminopeptidase NHomo sapiens (human)
secretory granule membraneAminopeptidase NHomo sapiens (human)
extracellular exosomeAminopeptidase NHomo sapiens (human)
cytoplasmAminopeptidase NHomo sapiens (human)
plasma membraneAminopeptidase NHomo sapiens (human)
extracellular spaceAminopeptidase NHomo sapiens (human)
extracellular regionDipeptidyl peptidase 4Homo sapiens (human)
lysosomal membraneDipeptidyl peptidase 4Homo sapiens (human)
plasma membraneDipeptidyl peptidase 4Homo sapiens (human)
focal adhesionDipeptidyl peptidase 4Homo sapiens (human)
cell surfaceDipeptidyl peptidase 4Homo sapiens (human)
membraneDipeptidyl peptidase 4Homo sapiens (human)
apical plasma membraneDipeptidyl peptidase 4Homo sapiens (human)
lamellipodiumDipeptidyl peptidase 4Homo sapiens (human)
endocytic vesicleDipeptidyl peptidase 4Homo sapiens (human)
lamellipodium membraneDipeptidyl peptidase 4Homo sapiens (human)
membrane raftDipeptidyl peptidase 4Homo sapiens (human)
intercellular canaliculusDipeptidyl peptidase 4Homo sapiens (human)
extracellular exosomeDipeptidyl peptidase 4Homo sapiens (human)
plasma membraneDipeptidyl peptidase 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (21)

Assay IDTitleYearJournalArticle
AID171628Toxicity was determined in rats at a dose of 30 mg/kg after 4 hour. (- denotes no activity in administered animals).1998Journal of medicinal chemistry, Aug-27, Volume: 41, Issue:18
Anticonvulsant activity and interactions with neuronal voltage-dependent sodium channel of analogues of ameltolide.
AID211677Neurotoxicity determined at 30 minutes after the administration of compound by rotarod test.(++= signify activity at 100 mg/kg)1998Journal of medicinal chemistry, Aug-27, Volume: 41, Issue:18
Anticonvulsant activity and interactions with neuronal voltage-dependent sodium channel of analogues of ameltolide.
AID168604Anticonvulsant activity was determined in rats at a dose of 30 mg/kg after 1 hour by MES test. (++++ denotes activity in 75-100% of administered animals)1998Journal of medicinal chemistry, Aug-27, Volume: 41, Issue:18
Anticonvulsant activity and interactions with neuronal voltage-dependent sodium channel of analogues of ameltolide.
AID219416Cytotoxicity in human embryonic lung flbroblast Wl-38 cells using WST-1 viability assay1999Bioorganic & medicinal chemistry letters, Feb-22, Volume: 9, Issue:4
Nonpeptide small-molecular inhibitors of dipeptidyl peptidase IV: N-phenylphthalimide analogs.
AID168750Anticonvulsant activity was determined in rats at a dose of 30 mg/kg after 15 minutes by MES test. (++++ denotes activity in 75-100% of administered animals)1998Journal of medicinal chemistry, Aug-27, Volume: 41, Issue:18
Anticonvulsant activity and interactions with neuronal voltage-dependent sodium channel of analogues of ameltolide.
AID56211Inhibitory activity against dipeptidyl peptidase IV (DPP- IV)1998Journal of medicinal chemistry, Jan-29, Volume: 41, Issue:3
Novel potent nonpeptide aminopeptidase N inhibitors with a cyclic imide skeleton.
AID168758Anticonvulsant activity was determined in rats at a dose of 30 mg/kg after 30 minutes by MES test. (++++ denotes activity in 75-100% of administered animals)1998Journal of medicinal chemistry, Aug-27, Volume: 41, Issue:18
Anticonvulsant activity and interactions with neuronal voltage-dependent sodium channel of analogues of ameltolide.
AID197748Effective dose administered intraperitoneally in the MES model2001Journal of medicinal chemistry, Jan-18, Volume: 44, Issue:2
Medicinal chemistry of neuronal voltage-gated sodium channel blockers.
AID109359Anticonvulsant activity determined at 4 hours after the administration of compound using sc Ptz test. (- denotes activity at 300 mg/kg)1998Journal of medicinal chemistry, Aug-27, Volume: 41, Issue:18
Anticonvulsant activity and interactions with neuronal voltage-dependent sodium channel of analogues of ameltolide.
AID211680Neurotoxicity determined at 4 hours after the administration of compound by rotarod test (++= signify activity at 100 mg/kg)1998Journal of medicinal chemistry, Aug-27, Volume: 41, Issue:18
Anticonvulsant activity and interactions with neuronal voltage-dependent sodium channel of analogues of ameltolide.
AID38364Inhibitory activity against aminopeptidase N (APN) in human acute lymphoblastic leukemia MOLT-4 cell line1999Bioorganic & medicinal chemistry letters, Feb-22, Volume: 9, Issue:4
Nonpeptide small-molecular inhibitors of dipeptidyl peptidase IV: N-phenylphthalimide analogs.
AID56226Inhibitory activity against Dipeptidylpeptidase IV (DPP IV) in human acute lymphoblastic leukemia MOLT-4 cell line1999Bioorganic & medicinal chemistry letters, Feb-22, Volume: 9, Issue:4
Nonpeptide small-molecular inhibitors of dipeptidyl peptidase IV: N-phenylphthalimide analogs.
AID109349Anticonvulsant activity determined at 30 minutes after the administration of compound using sc Ptz test. (+++ = activity at 30 mg/kg)1998Journal of medicinal chemistry, Aug-27, Volume: 41, Issue:18
Anticonvulsant activity and interactions with neuronal voltage-dependent sodium channel of analogues of ameltolide.
AID178278Anticonvulsant ED50 activity by MES test in rats dosed orally1998Journal of medicinal chemistry, Aug-27, Volume: 41, Issue:18
Anticonvulsant activity and interactions with neuronal voltage-dependent sodium channel of analogues of ameltolide.
AID168754Anticonvulsant activity was determined in rats at a dose of 30 mg/kg after 2 hour by MES test. (++++ denotes activity in 75-100% of administered animals)1998Journal of medicinal chemistry, Aug-27, Volume: 41, Issue:18
Anticonvulsant activity and interactions with neuronal voltage-dependent sodium channel of analogues of ameltolide.
AID168761Anticonvulsant activity was determined in rats at a dose of 30 mg/kg after 4 hour by MES test. (++ denotes activity in 25-50% of administered animals).1998Journal of medicinal chemistry, Aug-27, Volume: 41, Issue:18
Anticonvulsant activity and interactions with neuronal voltage-dependent sodium channel of analogues of ameltolide.
AID109357Anticonvulsant activity determined at 4 hours after the administration of compound using MES test.(++= signify activity at 100 mg/kg)1998Journal of medicinal chemistry, Aug-27, Volume: 41, Issue:18
Anticonvulsant activity and interactions with neuronal voltage-dependent sodium channel of analogues of ameltolide.
AID38377Inhibitory activity against aminopeptidase N assayed by the L-Ala-MCA method.1998Journal of medicinal chemistry, Jan-29, Volume: 41, Issue:3
Novel potent nonpeptide aminopeptidase N inhibitors with a cyclic imide skeleton.
AID217925Inhibition of [3H]BTX binding to cardiac voltage-gated sodium channel2001Journal of medicinal chemistry, Jan-18, Volume: 44, Issue:2
Medicinal chemistry of neuronal voltage-gated sodium channel blockers.
AID205272Apparent IC50 value by [3H]batrachotoxinin-A-20-alpha-benzoate-binding test performed in rat brain synaptosomes1998Journal of medicinal chemistry, Aug-27, Volume: 41, Issue:18
Anticonvulsant activity and interactions with neuronal voltage-dependent sodium channel of analogues of ameltolide.
AID109345Anticonvulsant activity determined at 30 minutes after the administration of compound using MES test. (+++ = activity at 30 mg/kg)1998Journal of medicinal chemistry, Aug-27, Volume: 41, Issue:18
Anticonvulsant activity and interactions with neuronal voltage-dependent sodium channel of analogues of ameltolide.
[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%
Reviews1 (20.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other4 (80.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]