Page last updated: 2024-12-05

5-methylbenzimidazole

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

Description

5-Methylbenzimidazole is a heterocyclic compound with a benzimidazole core and a methyl group at the 5-position. It has been studied for its potential biological activity and its role in the synthesis of other compounds. For instance, it has been used as a starting material in the synthesis of various pharmaceuticals, including anti-infective drugs. Research suggests that 5-methylbenzimidazole may exhibit anti-inflammatory and analgesic properties. The presence of the methyl group at the 5-position influences the compound's chemical and biological properties, making it an intriguing subject for further investigation.'

5-methylbenzimidazole: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

5-methyl-1H-benzimidazole : A member of the class of imidazoles that is 1H-benzimidazole in which the hydrogen at position 5 is substituted by a methyl group. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID11979
CHEMBL ID157729
CHEBI ID40205
SCHEMBL ID10903
MeSH IDM0548821

Synonyms (51)

Synonym
BIDD:GT0671
AC-2010
1h-benzimidazole, 6-methyl-
unii-r56855uc8y
r56855uc8y ,
BB 0219447
wln: t56 bm dnj g1
1h-benzimidazole, 5-methyl-
nsc3826
614-97-1
5-methylbenzimidazole
nsc-3826
benzimidazole, 5-methyl-
benzimidazole, 5(or 6)-methyl-
einecs 210-401-4
nsc 3826
phenylalanine, 4-cyano-, ethyl ester
inchi=1/c8h8n2/c1-6-2-3-7-8(4-6)10-5-9-7/h2-5h,1h3,(h,9,10
ethyl 4-cyanophenylalaninate
CHEBI:40205 ,
5-methyl-1h-benzimidazole
6-methyl-1h-benzimidazole
DB03177
5MB ,
5-methylbenzimidazole, 98%
STK242092
AKOS000275603
F2163-0011
5-methyl-1h-1,3-benzodiazole
CHEMBL157729 ,
bdbm50208880
M1321
AKOS015953401
5-methyl-1h-benzo[d]imidazole
FT-0620642
5-methyl-1h-benzoimidazole
SCHEMBL10903
DTXSID1060639
5(6)-methylbenzimidazole
W-105148
mfcd00010740
GS-6306
6-methyl-1h-1,3-benzodiazole
6-methylbenzimidazol
SY037745
Z3234957798
Q27094112
H10512
EN300-88816
CS-0071626
PD007748
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
imidazolesA five-membered organic heterocycle containing two nitrogen atoms at positions 1 and 3, or any of its derivatives; compounds containing an imidazole skeleton.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (1)

PathwayProteinsCompounds
5-methylbenzimidazolyl adenosylcobamide biosynthesis from adenosylcobinamide-GDP38

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Cytochrome P450 2B1Rattus norvegicus (Norway rat)IC50 (µMol)575.44007.40007.80008.2000AID38394
Xanthine dehydrogenase/oxidaseHomo sapiens (human)IC50 (µMol)200.00000.00132.81389.8200AID287937
[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)
Cytochrome P450 2B1Rattus norvegicus (Norway rat)Ks62.00001.10001.10001.1000AID184443
Cytochrome P450 1A1Rattus norvegicus (Norway rat)Ks210.00001.70001.70001.7000AID184442
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (27)

Processvia Protein(s)Taxonomy
allantoin metabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
negative regulation of protein phosphorylationXanthine dehydrogenase/oxidaseHomo sapiens (human)
negative regulation of endothelial cell proliferationXanthine dehydrogenase/oxidaseHomo sapiens (human)
guanine catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
inosine catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
deoxyinosine catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
adenosine catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
deoxyadenosine catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
deoxyguanosine catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
AMP catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
IMP catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
activation of cysteine-type endopeptidase activity involved in apoptotic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
lactationXanthine dehydrogenase/oxidaseHomo sapiens (human)
hypoxanthine catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
xanthine catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
negative regulation of gene expressionXanthine dehydrogenase/oxidaseHomo sapiens (human)
iron-sulfur cluster assemblyXanthine dehydrogenase/oxidaseHomo sapiens (human)
amide catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
negative regulation of endothelial cell differentiationXanthine dehydrogenase/oxidaseHomo sapiens (human)
GMP catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
dGMP catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
dAMP catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
negative regulation of phosphatidylinositol 3-kinase/protein kinase B signal transductionXanthine dehydrogenase/oxidaseHomo sapiens (human)
positive regulation of p38MAPK cascadeXanthine dehydrogenase/oxidaseHomo sapiens (human)
negative regulation of vascular endothelial growth factor signaling pathwayXanthine dehydrogenase/oxidaseHomo sapiens (human)
positive regulation of reactive oxygen species metabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
negative regulation of vasculogenesisXanthine dehydrogenase/oxidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (11)

Processvia Protein(s)Taxonomy
xanthine dehydrogenase activityXanthine dehydrogenase/oxidaseHomo sapiens (human)
xanthine oxidase activityXanthine dehydrogenase/oxidaseHomo sapiens (human)
iron ion bindingXanthine dehydrogenase/oxidaseHomo sapiens (human)
protein bindingXanthine dehydrogenase/oxidaseHomo sapiens (human)
protein homodimerization activityXanthine dehydrogenase/oxidaseHomo sapiens (human)
molybdopterin cofactor bindingXanthine dehydrogenase/oxidaseHomo sapiens (human)
flavin adenine dinucleotide bindingXanthine dehydrogenase/oxidaseHomo sapiens (human)
2 iron, 2 sulfur cluster bindingXanthine dehydrogenase/oxidaseHomo sapiens (human)
hypoxanthine dehydrogenase activityXanthine dehydrogenase/oxidaseHomo sapiens (human)
hypoxanthine oxidase activityXanthine dehydrogenase/oxidaseHomo sapiens (human)
FAD bindingXanthine dehydrogenase/oxidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
cytosolXanthine dehydrogenase/oxidaseHomo sapiens (human)
extracellular spaceXanthine dehydrogenase/oxidaseHomo sapiens (human)
peroxisomeXanthine dehydrogenase/oxidaseHomo sapiens (human)
cytosolXanthine dehydrogenase/oxidaseHomo sapiens (human)
sarcoplasmic reticulumXanthine dehydrogenase/oxidaseHomo sapiens (human)
extracellular spaceXanthine dehydrogenase/oxidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (6)

Assay IDTitleYearJournalArticle
AID287937Inhibition of human xanthine oxidase2007Bioorganic & medicinal chemistry, May-15, Volume: 15, Issue:10
The screening and characterization of 6-aminopurine-based xanthine oxidase inhibitors.
AID38394Inhibitory potency to aminopyrine N-demethylase activity (P450) in hepatic microsomes from phenobarbitone-induced rats.1982Journal of medicinal chemistry, Aug, Volume: 25, Issue:8
Inhibition of rat hepatic microsomal aminopyrine N-demethylase activity by benzimidazole derivatives. Quantitative structure-activity relationships.
AID1059430Inhibition of recombinant human IDO1 expressed in Escherichia coli EC538 using L-tryptophan as substrate at 1 mM after 1 hr relative to control2013Bioorganic & medicinal chemistry, Dec-15, Volume: 21, Issue:24
Discovery and characterisation of hydrazines as inhibitors of the immune suppressive enzyme, indoleamine 2,3-dioxygenase 1 (IDO1).
AID184443Interaction with cytochrome P450 in Phenobarbitone-induced rat hepatic microsomes1982Journal of medicinal chemistry, Jun, Volume: 25, Issue:6
Inhibitors of hepatic mixed-function oxidases. 4. Effects of benzimidazole and related compounds on aryl hydrocarbon hydroxylase activity from phenobarbitone and 3-methylcholanthrene induced rats.
AID24235Partition coefficient (logP)1982Journal of medicinal chemistry, Aug, Volume: 25, Issue:8
Inhibition of rat hepatic microsomal aminopyrine N-demethylase activity by benzimidazole derivatives. Quantitative structure-activity relationships.
AID184442Interaction (Ks) with cytochrome P450 in 3-methylcholanthrene-induced rat hepatic microsomes1982Journal of medicinal chemistry, Jun, Volume: 25, Issue:6
Inhibitors of hepatic mixed-function oxidases. 4. Effects of benzimidazole and related compounds on aryl hydrocarbon hydroxylase activity from phenobarbitone and 3-methylcholanthrene induced rats.
[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-19904 (40.00)18.7374
1990's0 (0.00)18.2507
2000's1 (10.00)29.6817
2010's4 (40.00)24.3611
2020's1 (10.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 24.46

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 Index24.46 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index4.58 (4.65)
Search Engine Demand Index17.79 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (24.46)

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%
Other11 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]