Page last updated: 2024-11-06

methylbenzoprim

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

Description

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

Cross-References

ID SourceID
PubMed CID72438
CHEMBL ID56170
SCHEMBL ID8590014
MeSH IDM0177988

Synonyms (27)

Synonym
smr001565314
NEURO_000220
NCI60_003643
5-[4-[benzyl(methyl)amino]-3-nitro-phenyl]-6-ethyl-pyrimidine-2,4-diamine
118344-71-1
methylbenzoprim
nsc382035
2,4-pyrimidinediamine, 6-ethyl-5-[4-[methyl(phenylmethyl)amino]-3-nitrophenyl]-
mls002701717 ,
nsc-382035
2, 6-ethyl-5-[4-[methyl(phenylmethyl) amino]-3-nitrophenyl]-
CHEMBL56170 ,
5-[4-[benzyl(methyl)amino]-3-nitrophenyl]-6-ethylpyrimidine-2,4-diamine
ZINC03777839
cid_72438
5-[4-(benzyl-methyl-amino)-3-nitro-phenyl]-6-ethyl-pyrimidine-2,4-diamine
(methylbenzoprim, mbp) 5-[4-(benzyl-methyl-amino)-3-nitro-phenyl]-6-ethyl-pyrimidine-2,4-diamine
bdbm50058420
2,4-pyrimidinediamine, 6-ethyl-5-(4-(methyl(phenylmethyl)amino)-3-nitrophenyl)-
nsc 382035
SCHEMBL8590014
DTXSID70152101
icx5609264
6-ethyl-5-[4-[methyl(phenylmethyl)amino]-3-nitrophenyl]-2,4-pyrimidinediamine
PQ9EF7YE44
methobenzaprim
5-{4-[benzyl(methyl)amino]-3-nitrophenyl}-6-ethylpyrimidine-2,4-diamine

Research Excerpts

Overview

Methylbenzoprim (MBP) is a potent inhibitor of dihydrofolate reductase. MBP is more selective for mammalian than bacterial enzymes.

ExcerptReferenceRelevance
"Methylbenzoprim (MBP) is a potent inhibitor of dihydrofolate reductase, which is more selective for mammalian than bacterial enzymes. "( Structural studies on bio-active compounds. 20. Molecular modeling and crystallographic studies on methylbenzoprim, a potent inhibitor of dihydrofolate reductase.
Denny, BJ; Griffin, RJ; Lambert, PA; Meek, MA; Ringan, NS; Schwalbe, CH; Stevens, MF, 1992
)
1.94
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (14)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, JmjC domain-containing histone demethylation protein 3AHomo sapiens (human)Potency44.66840.631035.7641100.0000AID504339
glp-1 receptor, partialHomo sapiens (human)Potency11.63920.01846.806014.1254AID624172; AID624417
TDP1 proteinHomo sapiens (human)Potency2.63110.000811.382244.6684AID686978; AID686979
Smad3Homo sapiens (human)Potency23.41590.00527.809829.0929AID588855; AID720534; AID720536; AID720537
67.9K proteinVaccinia virusPotency1.12950.00018.4406100.0000AID720579; AID720580
IDH1Homo sapiens (human)Potency2.90930.005210.865235.4813AID686970
nuclear factor erythroid 2-related factor 2 isoform 2Homo sapiens (human)Potency1.22890.00419.984825.9290AID504444; AID720524
DNA polymerase eta isoform 1Homo sapiens (human)Potency5.62340.100028.9256213.3130AID588591
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Gli1Mus musculus (house mouse)IC50 (µMol)1.57000.02704.293911.4000AID602464
protein Wnt-3a precursorMus musculus (house mouse)IC50 (µMol)5.28000.44104.995214.8000AID651570
Dihydrofolate reductaseEscherichia coli K-12IC50 (µMol)0.90000.00150.55126.8000AID57590
Dihydrofolate reductasePneumocystis cariniiIC50 (µMol)1.60000.00060.54766.2000AID55702; AID55830
Bifunctional dihydrofolate reductase-thymidylate synthaseToxoplasma gondiiIC50 (µMol)0.09100.00061.042810.0000AID56179; AID56314
Dihydrofolate reductaseRattus norvegicus (Norway rat)IC50 (µMol)0.00630.00060.35076.2000AID57645; AID57787; AID57813; AID57965
Dihydrofolate reductaseRattus norvegicus (Norway rat)Ki0.00000.00000.02490.0745AID58147
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (9)

Processvia Protein(s)Taxonomy
10-formyltetrahydrofolate biosynthetic processDihydrofolate reductaseEscherichia coli K-12
response to xenobiotic stimulusDihydrofolate reductaseEscherichia coli K-12
folic acid biosynthetic processDihydrofolate reductaseEscherichia coli K-12
one-carbon metabolic processDihydrofolate reductaseEscherichia coli K-12
response to methotrexateDihydrofolate reductaseEscherichia coli K-12
tetrahydrofolate biosynthetic processDihydrofolate reductaseEscherichia coli K-12
response to antibioticDihydrofolate reductaseEscherichia coli K-12
dihydrofolate metabolic processDihydrofolate reductaseEscherichia coli K-12
folic acid metabolic processDihydrofolate reductaseEscherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (9)

Processvia Protein(s)Taxonomy
dihydrofolate reductase activityDihydrofolate reductaseEscherichia coli K-12
protein bindingDihydrofolate reductaseEscherichia coli K-12
folic acid bindingDihydrofolate reductaseEscherichia coli K-12
oxidoreductase activityDihydrofolate reductaseEscherichia coli K-12
NADP bindingDihydrofolate reductaseEscherichia coli K-12
methotrexate bindingDihydrofolate reductaseEscherichia coli K-12
dihydrofolic acid bindingDihydrofolate reductaseEscherichia coli K-12
NADP+ bindingDihydrofolate reductaseEscherichia coli K-12
NADPH bindingDihydrofolate reductaseEscherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
cytosolDihydrofolate reductaseEscherichia coli K-12
cytosolDihydrofolate reductaseEscherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (36)

Assay IDTitleYearJournalArticle
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745849Viability Counterscreen for CMV-Luciferase Assay of Inhibitors of ATXN expression
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745848Confirmatory qHTS for Inhibitors of ATXN expression
AID1745850Viability Counterscreen for Confirmatory qHTS for Inhibitors of ATXN expression
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745846Firefly Luciferase Counterscreen for Inhibitors of ATXN expression
AID1745847CMV-Luciferase Counterscreen for Inhibitors of ATXN expression
AID57590Inhibitory activity against Escherichia coli dihydrofolate reductase1992Journal of medicinal chemistry, Jun-12, Volume: 35, Issue:12
Structural studies on bio-active compounds. 20. Molecular modeling and crystallographic studies on methylbenzoprim, a potent inhibitor of dihydrofolate reductase.
AID57787Inhibitory activity against rat liver dihydrofolate reductase1992Journal of medicinal chemistry, Jun-12, Volume: 35, Issue:12
Structural studies on bio-active compounds. 20. Molecular modeling and crystallographic studies on methylbenzoprim, a potent inhibitor of dihydrofolate reductase.
AID55830Inhibitory activity against Dihydrofolate reductase from Pneumocystis carinii was evaluated using 90 uM dihydrofolic acid as substrate1997Journal of medicinal chemistry, Sep-12, Volume: 40, Issue:19
Nonclassical 2,4-diamino-5-aryl-6-ethylpyrimidine antifolates: activity as inhibitors of dihydrofolate reductase from Pneumocystis carinii and Toxoplasma gondii and as antitumor agents.
AID247429Growth inhibitory activity against human HT-29 cell line in presence of Hypoxanthine thymidine(HT)2004Journal of medicinal chemistry, Jul-29, Volume: 47, Issue:16
Structural studies on bioactive compounds. 39. Biological consequences of the structural modification of DHFR-inhibitory 2,4-diamino-6-(4-substituted benzylamino-3-nitrophenyl)-6-ethylpyrimidines ('benzoprims').
AID120314Number of M5076 reticulum cell sarcoma bearing mice survived among the tested (5) on day 24 after treating with compound dose of 25 mg/Kg/day1997Journal of medicinal chemistry, Sep-12, Volume: 40, Issue:19
Nonclassical 2,4-diamino-5-aryl-6-ethylpyrimidine antifolates: activity as inhibitors of dihydrofolate reductase from Pneumocystis carinii and Toxoplasma gondii and as antitumor agents.
AID247221Growth inhibitory activity against human HT-29 cell line2004Journal of medicinal chemistry, Jul-29, Volume: 47, Issue:16
Structural studies on bioactive compounds. 39. Biological consequences of the structural modification of DHFR-inhibitory 2,4-diamino-6-(4-substituted benzylamino-3-nitrophenyl)-6-ethylpyrimidines ('benzoprims').
AID58147Inhibitory activity of compound against rat liver Dihydrofolate reductase1997Journal of medicinal chemistry, Sep-12, Volume: 40, Issue:19
Nonclassical 2,4-diamino-5-aryl-6-ethylpyrimidine antifolates: activity as inhibitors of dihydrofolate reductase from Pneumocystis carinii and Toxoplasma gondii and as antitumor agents.
AID233285Selectivity ratio is IC50 of rat liver DHFR to that of Pneumocystis carinii DHFR1997Journal of medicinal chemistry, Sep-12, Volume: 40, Issue:19
Nonclassical 2,4-diamino-5-aryl-6-ethylpyrimidine antifolates: activity as inhibitors of dihydrofolate reductase from Pneumocystis carinii and Toxoplasma gondii and as antitumor agents.
AID247430Growth inhibitory activity against human HCT116 cell line in presence of Hypoxanthine thymidine(HT)2004Journal of medicinal chemistry, Jul-29, Volume: 47, Issue:16
Structural studies on bioactive compounds. 39. Biological consequences of the structural modification of DHFR-inhibitory 2,4-diamino-6-(4-substituted benzylamino-3-nitrophenyl)-6-ethylpyrimidines ('benzoprims').
AID232760Selectivity index measured as the ratio of IC50 for rat liver DHFR to IC50 for Toxoplasma gondii DHFR.1997Journal of medicinal chemistry, Jun-06, Volume: 40, Issue:12
Structural studies on bioactive compounds. 28. Selective activity of triazenyl-substituted pyrimethamine derivatives against Pneumocystis carinii dihydrofolate reductase.
AID55702In vitro inhibitory concentration against Pneumocystis carinii dihydrofolate reductase1997Journal of medicinal chemistry, Jun-06, Volume: 40, Issue:12
Structural studies on bioactive compounds. 28. Selective activity of triazenyl-substituted pyrimethamine derivatives against Pneumocystis carinii dihydrofolate reductase.
AID122086Antitumor activity expressed as a ratio of tumor volumes of test (T) animals compared to control (C) animals(100) at a dose of 25 mg/kg/day1997Journal of medicinal chemistry, Sep-12, Volume: 40, Issue:19
Nonclassical 2,4-diamino-5-aryl-6-ethylpyrimidine antifolates: activity as inhibitors of dihydrofolate reductase from Pneumocystis carinii and Toxoplasma gondii and as antitumor agents.
AID232759Selectivity index measured as the ratio of IC50 for rat liver DHFR to IC50 for Pneumocystis carinii DHFR.1997Journal of medicinal chemistry, Jun-06, Volume: 40, Issue:12
Structural studies on bioactive compounds. 28. Selective activity of triazenyl-substituted pyrimethamine derivatives against Pneumocystis carinii dihydrofolate reductase.
AID57965Inhibitory activity against Dihydrofolate reductase from rat liver was evaluated using 90 uM dihydrofolic acid as substrate1997Journal of medicinal chemistry, Sep-12, Volume: 40, Issue:19
Nonclassical 2,4-diamino-5-aryl-6-ethylpyrimidine antifolates: activity as inhibitors of dihydrofolate reductase from Pneumocystis carinii and Toxoplasma gondii and as antitumor agents.
AID57645In vitro inhibitory concentration against rat liver dihydrofolate reductase1989Journal of medicinal chemistry, Nov, Volume: 32, Issue:11
Structural studies on bioactive compounds. 8. Synthesis, crystal structure, and biological properties of a new series of 2,4-diamino-5-aryl-6-ethylpyrimidine dihydrofolate reductase inhibitors with in vivo activity against a methotrexate-resistant tumor c
AID57813In vitro inhibitory concentration against rat liver dihydrofolate reductase1997Journal of medicinal chemistry, Jun-06, Volume: 40, Issue:12
Structural studies on bioactive compounds. 28. Selective activity of triazenyl-substituted pyrimethamine derivatives against Pneumocystis carinii dihydrofolate reductase.
AID247223Growth inhibitory activity against human HCT116 cell line2004Journal of medicinal chemistry, Jul-29, Volume: 47, Issue:16
Structural studies on bioactive compounds. 39. Biological consequences of the structural modification of DHFR-inhibitory 2,4-diamino-6-(4-substituted benzylamino-3-nitrophenyl)-6-ethylpyrimidines ('benzoprims').
AID56314Inhibitory activity against Dihydrofolate reductase from Toxoplasma gondii was evaluated using 90 uM dihydrofolic acid as substrate1997Journal of medicinal chemistry, Sep-12, Volume: 40, Issue:19
Nonclassical 2,4-diamino-5-aryl-6-ethylpyrimidine antifolates: activity as inhibitors of dihydrofolate reductase from Pneumocystis carinii and Toxoplasma gondii and as antitumor agents.
AID233287Selectivity ratio is IC50 of rat liver DHFR to that of Toxoplasma gondii DHFR1997Journal of medicinal chemistry, Sep-12, Volume: 40, Issue:19
Nonclassical 2,4-diamino-5-aryl-6-ethylpyrimidine antifolates: activity as inhibitors of dihydrofolate reductase from Pneumocystis carinii and Toxoplasma gondii and as antitumor agents.
AID56179Inhibitory concentration against Toxoplasma gondii dihydrofolate reductase1997Journal of medicinal chemistry, Jun-06, Volume: 40, Issue:12
Structural studies on bioactive compounds. 28. Selective activity of triazenyl-substituted pyrimethamine derivatives against Pneumocystis carinii dihydrofolate reductase.
[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-19901 (7.69)18.7374
1990's6 (46.15)18.2507
2000's2 (15.38)29.6817
2010's3 (23.08)24.3611
2020's1 (7.69)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.27

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 Index12.27 (24.57)
Research Supply Index2.71 (2.92)
Research Growth Index4.98 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.27)

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]