Page last updated: 2024-11-04

5,6-dimethylbenzimidazole

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

Description

5,6-dimethylbenzimidazole: RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

5,6-dimethylbenzimidazole : A dimethylbenzimidazole carrying methyl substituents at positions 5 and 6. [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 CID675
CHEMBL ID351132
CHEBI ID15890
SCHEMBL ID312977
SCHEMBL ID3893948
MeSH IDM0064227

Synonyms (66)

Synonym
unii-553xi1ds20
553xi1ds20 ,
5-23-06-00454 (beilstein handbook reference)
BB 0241929
CHEBI:15890 ,
5,6-dimethyl-1h-benzimidazole
benzimidazole,6-dimethyl-
dimezol
1h-benzimidazole,6-dimethyl-
nsc-68316
dimezol base
nsc68316
dimedazol
dimedazole
dimesol
1h-benzimidazole, 5,6-dimethyl-
benzimidazole, 5,6-dimethyl-
brn 0116595
nsc 68316
ai3-52806
einecs 209-488-1
5,6-dimethylbenzimidazole
DIMETHYLBENZIMIDAZOLE ,
582-60-5
C03114
5,6-dimethylbenzimidazole, >=99%
DB02591
inchi=1/c9h10n2/c1-6-3-8-9(4-7(6)2)11-5-10-8/h3-5h,1-2h3,(h,10,11
STK001228
B97E9041-BA87-4952-8BE7-E80B4E480262
CHEMBL351132 ,
bdbm50208872
D1345
AB00375938-02
HMS1659L03
AKOS000121551
A831807
5,6-dimethyl-1h-benzo[d]imidazole
5,6-dimethyl-1h-benzoimidazole
5.6-dimethylbenzimidazole
5,6-dimethyl benzimidazole
BMSE000881
FT-0619833
AM20040774
S3097
5,6-dimethylbenzimidazole [mi]
SCHEMBL312977
SCHEMBL3893948
5,6-dimethylbenzoimidazole
Q-100667
mfcd00005603
F3145-1021
5,6-dimethyl-1h-1,3-benzodiazole
AC-8359
5,6-dimethylbenzimidazole, purum, >=99.0% (nt)
dimezoldimedazol
dimezol (van)
DTXSID70870631
HY-W017511
F17509
CS-W018227
AS-10901
Q15269676
5,6-dimethylbenzo[d]imidazole
EN300-16463
Z55928828
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
Escherichia coli metaboliteAny bacterial metabolite produced during a metabolic reaction in Escherichia coli.
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
[role 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]

Drug Classes (1)

ClassDescription
dimethylbenzimidazole
[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 (11)

PathwayProteinsCompounds
Riboflavin Metabolism515
Adenosylcobalamin Salvage from Cobinamide1219
adenosylcobalamin biosynthesis from adenosylcobinamide-GDP I512
5,6-dimethylbenzimidazole biosynthesis I (aerobic)311
5,6-dimethylbenzimidazole biosynthesis II (anaerobic)614
adenosylcobalamin biosynthesis from cobyrinate a,c-diamide I626
adenosylcobalamin salvage from cobinamide I419
adenosylcobalamin biosynthesis from cobyrinate a,c-diamide II029
adenosylcobalamin biosynthesis II (aerobic)060
adenosylcobalamin biosynthesis II (late cobalt incorporation)2655
adenosylcobalamin salvage from cobinamide II021

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Cytochrome P450 2B1Rattus norvegicus (Norway rat)IC50 (µMol)180.98507.40007.80008.2000AID38394; AID38395
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)Ks320.00001.70001.70001.7000AID184441
Polyunsaturated fatty acid 5-lipoxygenaseRattus norvegicus (Norway rat)Ks320.00001.70001.70001.7000AID184441
[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 (21)

Assay IDTitleYearJournalArticle
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID1543820Antiproliferative activity against human MCF7 cells assessed as reduction in cell viability incubated for 48 hrs by MTS assay2019European journal of medicinal chemistry, Apr-15, Volume: 168Synthesis and antitumor activity of novel steroidal imidazolium salt derivatives.
AID409954Inhibition of mouse brain MAOA2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID1543822Antiproliferative activity against human SW480 cells assessed as reduction in cell viability incubated for 48 hrs by MTS assay2019European journal of medicinal chemistry, Apr-15, Volume: 168Synthesis and antitumor activity of novel steroidal imidazolium salt derivatives.
AID1543818Antiproliferative activity against human HL60 cells assessed as reduction in cell viability incubated for 48 hrs by MTS assay2019European journal of medicinal chemistry, Apr-15, Volume: 168Synthesis and antitumor activity of novel steroidal imidazolium salt derivatives.
AID1543821Antiproliferative activity against human A549 cells assessed as reduction in cell viability incubated for 48 hrs by MTS assay2019European journal of medicinal chemistry, Apr-15, Volume: 168Synthesis and antitumor activity of novel steroidal imidazolium salt derivatives.
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.
AID39088Inhibition of Aryl hydrocarbon hydroxylase in phenobarbitone-treated rats1982Journal 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.
AID39091Inhibition of Aryl hydrocarbon hydroxylase in phenobarbitone-treated rats1982Journal 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.
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.
AID287937Inhibition of human xanthine oxidase2007Bioorganic & medicinal chemistry, May-15, Volume: 15, Issue:10
The screening and characterization of 6-aminopurine-based xanthine oxidase inhibitors.
AID184441Interaction 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.
AID642704Cytotoxicity against human HCT116 cells after 48 hrs by MTT assay2012Bioorganic & medicinal chemistry letters, Feb-01, Volume: 22, Issue:3
Synthesis and biological evaluation of benzo[d]imidazole derivatives as potential anti-cancer agents.
AID1543819Antiproliferative activity against human SMMC7721 cells assessed as reduction in cell viability incubated for 48 hrs by MTS assay2019European journal of medicinal chemistry, Apr-15, Volume: 168Synthesis and antitumor activity of novel steroidal imidazolium salt derivatives.
AID409956Inhibition of mouse brain MAOB2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID39086Effect on Aryl hydrocarbon hydroxylase activity in 3-methylcolanthrene-induced rat liver microsomes at 8x10E-4M1982Journal 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.
AID38395Inhibition of Aminopyrine N-demethylase in Phenobarbitone-treated rats1982Journal 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.
AID642705Cytotoxicity against human MCF7 cells after 48 hrs by MTT assay2012Bioorganic & medicinal chemistry letters, Feb-01, Volume: 22, Issue:3
Synthesis and biological evaluation of benzo[d]imidazole derivatives as potential anti-cancer agents.
AID26812Partition coefficient (logP)1982Journal 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.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (80)

TimeframeStudies, This Drug (%)All Drugs %
pre-199016 (20.00)18.7374
1990's19 (23.75)18.2507
2000's21 (26.25)29.6817
2010's24 (30.00)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: 25.84

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 Index25.84 (24.57)
Research Supply Index4.49 (2.92)
Research Growth Index4.54 (4.65)
Search Engine Demand Index31.58 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (25.84)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (1.15%)5.53%
Reviews2 (2.30%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other84 (96.55%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]