Page last updated: 2024-11-07

2-(4-ethoxybenzyl)-1-diethylaminoethyl-5-isothiocyanatobenzimidazole

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Description

2-(4-ethoxybenzyl)-1-diethylaminoethyl-5-isothiocyanatobenzimidazole: site directed alkylating agent; selective agonist for mu receptors [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID128795
CHEMBL ID38832
SCHEMBL ID1239483
MeSH IDM0124529

Synonyms (17)

Synonym
NCGC00024630-01
tocris-0516
NCGC00024630-02
CHEMBL38832 ,
85951-65-1
{2-[2-(4-ethoxy-benzyl)-5-isothiocyanato-benzoimidazol-1-yl]-ethyl}-diethyl-amine
bdbm50027085
2-[2-[(4-ethoxyphenyl)methyl]-5-isothiocyanatobenzimidazol-1-yl]-n,n-diethylethanamine
1h-benzimidazol-1-ethanamine, 2-((4-ethoxyphenyl)methyl)-n,n-diethyl-5-isothiocyanato-
2-(4-ethoxybenzyl)-1-diethylaminoethyl-5-isothiocyanatobenzimidazole
1-[2-(n,n-diethylamino)ethyl]-2-(4-ethoxybenzyl)benzimidazole-5-isothiocyanate
DTXSID30235282
SCHEMBL1239483
1h-benzimidazole-1-ethanamine,2-[(4-ethoxyphenyl)methyl]-n,n-diethyl-5-isothiocyanato-
sr-01000597710
SR-01000597710-1
2-[(4-ethoxyphenyl)methyl]-n,n-diethyl-5-isothiocyano-1h-benzimidazole-1-ethanamine

Research Excerpts

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (32)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, TYROSYL-DNA PHOSPHODIESTERASEHomo sapiens (human)Potency17.63160.004023.8416100.0000AID485290
USP1 protein, partialHomo sapiens (human)Potency12.58930.031637.5844354.8130AID504865
TDP1 proteinHomo sapiens (human)Potency10.99840.000811.382244.6684AID686978; AID686979
regulator of G-protein signaling 4Homo sapiens (human)Potency37.68580.531815.435837.6858AID504845
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency12.58930.035520.977089.1251AID504332
cytochrome P450 2D6 isoform 1Homo sapiens (human)Potency1.25890.00207.533739.8107AID891
cellular tumor antigen p53 isoform aHomo sapiens (human)Potency15.84890.316212.443531.6228AID902
vitamin D3 receptor isoform VDRAHomo sapiens (human)Potency2.51190.354828.065989.1251AID504847
nuclear receptor ROR-gamma isoform 1Mus musculus (house mouse)Potency35.48130.00798.23321,122.0200AID2546; AID2551
cytochrome P450 3A4 isoform 1Homo sapiens (human)Potency1.25890.031610.279239.8107AID884; AID885
lethal factor (plasmid)Bacillus anthracis str. A2012Potency3.98110.020010.786931.6228AID912
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)Potency1.25891.000012.224831.6228AID885
Polyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)Potency3.98110.316212.765731.6228AID881
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)Potency1.25891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)Potency1.25891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)Potency1.25891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)Potency1.25891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)Potency1.25891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)Potency1.25891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)Potency1.25891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency1.25891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)Potency1.25891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)Potency1.25891.000012.224831.6228AID885
Histamine H2 receptorCavia porcellus (domestic guinea pig)Potency3.98110.00638.235039.8107AID881
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)Potency1.25891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)Potency1.25891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)Potency1.25891.000012.224831.6228AID885
Inositol monophosphatase 1Rattus norvegicus (Norway rat)Potency25.11891.000010.475628.1838AID1457
GABA theta subunitRattus norvegicus (Norway rat)Potency1.25891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)Potency1.25891.000012.224831.6228AID885
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Delta-type opioid receptorRattus norvegicus (Norway rat)EC50 (µMol)0.28000.00050.36496.9000AID149393
Kappa-type opioid receptorCavia porcellus (domestic guinea pig)EC50 (µMol)0.28000.00000.20671.4454AID149393
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (21)

Processvia Protein(s)Taxonomy
lipid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
phospholipid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
apoptotic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of cell population proliferationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of macrophage derived foam cell differentiationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
arachidonic acid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of cell migrationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
prostate gland developmentPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
regulation of epithelial cell differentiationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of chemokine productionPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of peroxisome proliferator activated receptor signaling pathwayPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
positive regulation of keratinocyte differentiationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of cell cyclePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
negative regulation of growthPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
hepoxilin biosynthetic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
endocannabinoid signaling pathwayPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
cannabinoid biosynthetic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipoxin A4 biosynthetic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
linoleic acid metabolic processPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipid oxidationPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipoxygenase pathwayPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
iron ion bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
calcium ion bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
protein bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
lipid bindingPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
linoleate 13S-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
arachidonate 8(S)-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
arachidonate 15-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
linoleate 9S-lipoxygenase activityPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (8)

Processvia Protein(s)Taxonomy
nucleusPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
cytosolPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
cytoskeletonPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
plasma membranePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
adherens junctionPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
focal adhesionPolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
membranePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
extracellular exosomePolyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (6)

Assay IDTitleYearJournalArticle
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID151294The binding affinity was evaluated against [3H]dalamid binding to rat brain membranes (mu opiate receptors).1984Journal of medicinal chemistry, Dec, Volume: 27, Issue:12
Probes for narcotic receptor mediated phenomena. 7. Synthesis and pharmacological properties of irreversible ligands specific for mu or delta opiate receptors.
AID149394The binding affinity was evaluated against [3H]dalamid binding to rat brain membranes (Opioid receptor delta 1)1984Journal of medicinal chemistry, Dec, Volume: 27, Issue:12
Probes for narcotic receptor mediated phenomena. 7. Synthesis and pharmacological properties of irreversible ligands specific for mu or delta opiate receptors.
AID149393The binding affinity was evaluated against [3H]dalamid binding to neuroblastoma X glioma hybrid cell NG108-15 (Opioid receptor delta 1)membranes1984Journal of medicinal chemistry, Dec, Volume: 27, Issue:12
Probes for narcotic receptor mediated phenomena. 7. Synthesis and pharmacological properties of irreversible ligands specific for mu or delta opiate receptors.
AID129313Antinociceptive activity was evaluated after subcutaneous injection by using mouse hotplate assay1984Journal of medicinal chemistry, Dec, Volume: 27, Issue:12
Probes for narcotic receptor mediated phenomena. 7. Synthesis and pharmacological properties of irreversible ligands specific for mu or delta opiate receptors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19907 (53.85)18.7374
1990's3 (23.08)18.2507
2000's1 (7.69)29.6817
2010's0 (0.00)24.3611
2020's2 (15.38)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.92

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 Index11.92 (24.57)
Research Supply Index2.71 (2.92)
Research Growth Index4.63 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.92)

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%
Other14 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]