Page last updated: 2024-11-05

etoprine

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

Description

etoprine: do not confuse with 3,5-dicarbethoxy-2,6-dimethyl-4-ethyl-1,4-dihydropyridine, also called DDEP [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID29142
CHEMBL ID21799
SCHEMBL ID3919
MeSH IDM0062045

Synonyms (32)

Synonym
2,4-diamino-5-(3,4-dichlorophenyl)-6-ethylpyrimidine
brn 0244129
ddep
2,4-pyrimidinediamine, 5-(3,4-dichlorophenyl)-6-ethyl-
ai3-25008
pyrimidine, 2,4-diamino-5-(3,4-dichlorophenyl)-6-ethyl-
2,4-diamino-5-(3',4'-dichlorophenyl)-6-ethylpyrimidine
etoprine [usan]
nsc 3062
2,4-dichlorophenyl)-6-ethylpyrimidine
nsc3062
2, 5-(3,4-dichlorophenyl)-6-ethyl-
ethodichlorophen
etoprine
nsc-3062
pyrimidine,4-diamino-5-(3,4-dichlorophenyl)-6-ethyl-
18588-57-3
NCI60_002606
5-(3,4-dichlorophenyl)-6-ethyl-pyrimidine-2,4-diamine
5-(3,4-dichlorophenyl)-6-ethyl-2,4-pyrimidinediamine
etoprine (usan)
D04108
chembl21799 ,
bdbm18783
5-(3,4-dichlorophenyl)-6-ethylpyrimidine-2,4-diamine
5-25-12-00256 (beilstein handbook reference)
406pgu9kgi ,
unii-406pgu9kgi
SCHEMBL3919
DTXSID20171807
ddep; ethodichlorophen; nsc 3062
Q27258296

Research Excerpts

Effects

ExcerptReferenceRelevance
"Etoprine has the greatest affinity for plasma proteins, but all three compounds are bound to human plasma protein by 87% or more at therapeutic concentrations."( Lipid-soluble inhibitors of dihydrofolate reductase. I. Kinetics, tissue distribution, and extent of metabolism of pyrimethamine, metoprine, and etoprine in the rat, dog, and man.
Brenckman, WD; Cavallito, JC; Deangelis, RL; Nichol, CA; Sigel, CW; Simmons, WS; Stickney, DR,
)
1.06
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Bifunctional dihydrofolate reductase-thymidylate synthasePlasmodium vivax (malaria parasite P. vivax)Ki0.00080.00020.00520.0225AID1797767
Bifunctional dihydrofolate reductase-thymidylate synthasePlasmodium falciparum K1IC50 (µMol)17.40000.00151.11635.8000AID157842
Bifunctional dihydrofolate reductase-thymidylate synthasePlasmodium falciparum K1Ki0.01520.00000.43696.6645AID219249; AID238767; AID58128; AID58250; AID58251; AID58253; AID58254; AID58255
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (27)

Assay IDTitleYearJournalArticle
AID158189In vitro antiplasmodial activity (IC50) against Plasmodium falciparum wtTM4/8.22002Journal of medicinal chemistry, Mar-14, Volume: 45, Issue:6
Development of 2,4-diaminopyrimidines as antimalarials based on inhibition of the S108N and C59R+S108N mutants of dihydrofolate reductase from pyrimethamine-resistant Plasmodium falciparum.
AID189629The capillary permeability of radioligand was measured in Rat brain1980Journal of medicinal chemistry, Jun, Volume: 23, Issue:6
Relationship of octanol/water partition coefficient and molecular weight to rat brain capillary permeability.
AID58266Inhibition of mutant S108N dihydrofolate reductase (DHFR) relative to Pyr2002Journal of medicinal chemistry, Mar-14, Volume: 45, Issue:6
Development of 2,4-diaminopyrimidines as antimalarials based on inhibition of the S108N and C59R+S108N mutants of dihydrofolate reductase from pyrimethamine-resistant Plasmodium falciparum.
AID219249Binding affinity towards wild-type dihydrofolate reductase of Plasmodium falciparum.2004Journal of medicinal chemistry, Jan-29, Volume: 47, Issue:3
Inhibitors of multiple mutants of Plasmodium falciparum dihydrofolate reductase and their antimalarial activities.
AID58255Inhibition of the wild-type dihydrofolate reductase (DHFR)2002Journal of medicinal chemistry, Mar-14, Volume: 45, Issue:6
Development of 2,4-diaminopyrimidines as antimalarials based on inhibition of the S108N and C59R+S108N mutants of dihydrofolate reductase from pyrimethamine-resistant Plasmodium falciparum.
AID229964IC50 ratio against Plasmodium falciparum K1CB1/TM42002Journal of medicinal chemistry, Mar-14, Volume: 45, Issue:6
Development of 2,4-diaminopyrimidines as antimalarials based on inhibition of the S108N and C59R+S108N mutants of dihydrofolate reductase from pyrimethamine-resistant Plasmodium falciparum.
AID58261Inhibition of mutant C59R+S108N dihydrofolate reductase (DHFR) relative to Pyr2002Journal of medicinal chemistry, Mar-14, Volume: 45, Issue:6
Development of 2,4-diaminopyrimidines as antimalarials based on inhibition of the S108N and C59R+S108N mutants of dihydrofolate reductase from pyrimethamine-resistant Plasmodium falciparum.
AID231313Ratio of binding affinity for mutant (N51I+C59R+S108N) to that of wild type dihydrofolate reductase2004Journal of medicinal chemistry, Jan-29, Volume: 47, Issue:3
Inhibitors of multiple mutants of Plasmodium falciparum dihydrofolate reductase and their antimalarial activities.
AID157842Antiplasmodial activity IC50 against Plasmodium falciparum K1CB1 DHFR double-mutant (C59R/S10)2002Journal of medicinal chemistry, Mar-14, Volume: 45, Issue:6
Development of 2,4-diaminopyrimidines as antimalarials based on inhibition of the S108N and C59R+S108N mutants of dihydrofolate reductase from pyrimethamine-resistant Plasmodium falciparum.
AID58254Inhibition of the S108N mutant of dihydrofolate reductase (DHFR)2002Journal of medicinal chemistry, Mar-14, Volume: 45, Issue:6
Development of 2,4-diaminopyrimidines as antimalarials based on inhibition of the S108N and C59R+S108N mutants of dihydrofolate reductase from pyrimethamine-resistant Plasmodium falciparum.
AID231312Ratio of binding affinity for mutant (C59R+S108N+I164L) to that of wild type dihydrofolate reductase2004Journal of medicinal chemistry, Jan-29, Volume: 47, Issue:3
Inhibitors of multiple mutants of Plasmodium falciparum dihydrofolate reductase and their antimalarial activities.
AID231314Ratio of binding affinity for mutant (N51I+C59R+S108N+I164L) to that of wild type dihydrofolate reductase2004Journal of medicinal chemistry, Jan-29, Volume: 47, Issue:3
Inhibitors of multiple mutants of Plasmodium falciparum dihydrofolate reductase and their antimalarial activities.
AID23271Partition coefficient (logD7.4)1990Journal of medicinal chemistry, Jul, Volume: 33, Issue:7
Structure-activity relationships of antineoplastic agents in multidrug resistance.
AID409943Inhibition of human recombinant MAOB by fluorimetric method2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID26811Partition coefficient (logP)1980Journal of medicinal chemistry, Jun, Volume: 23, Issue:6
Relationship of octanol/water partition coefficient and molecular weight to rat brain capillary permeability.
AID58253Inhibition of the C59R+S108N mutant of dihydrofolate reductase (DHFR)2002Journal of medicinal chemistry, Mar-14, Volume: 45, Issue:6
Development of 2,4-diaminopyrimidines as antimalarials based on inhibition of the S108N and C59R+S108N mutants of dihydrofolate reductase from pyrimethamine-resistant Plasmodium falciparum.
AID229767Ratio of Inhibition of the C59R+S108N mutant of dihydrofolate reductase (DHFR) to inhibition of wild type dihydrofolate reductase.2002Journal of medicinal chemistry, Mar-14, Volume: 45, Issue:6
Development of 2,4-diaminopyrimidines as antimalarials based on inhibition of the S108N and C59R+S108N mutants of dihydrofolate reductase from pyrimethamine-resistant Plasmodium falciparum.
AID58250Binding affinity towards mutant dihydrofolate reductase (N51I+C59R+S108N DHFR) of Plasmodium falciparum2004Journal of medicinal chemistry, Jan-29, Volume: 47, Issue:3
Inhibitors of multiple mutants of Plasmodium falciparum dihydrofolate reductase and their antimalarial activities.
AID238767Inhibition constant against Plasmodium falciparum dihydrofolate reductase2004Journal of medicinal chemistry, Aug-12, Volume: 47, Issue:17
Three-dimensional quantitative structure-activity relationship analysis of a set of Plasmodium falciparum dihydrofolate reductase inhibitors using a pharmacophore generation approach.
AID58271Inhibition of Plasmodium falciparum wild-type dihydrofolate reductase (DHFR) relative to Pyrimethamine.2002Journal of medicinal chemistry, Mar-14, Volume: 45, Issue:6
Development of 2,4-diaminopyrimidines as antimalarials based on inhibition of the S108N and C59R+S108N mutants of dihydrofolate reductase from pyrimethamine-resistant Plasmodium falciparum.
AID58128Binding affinity towards mutant dihydrofolate reductase (C59R+S108N+I164L DHFR) of Plasmodium falciparum2004Journal of medicinal chemistry, Jan-29, Volume: 47, Issue:3
Inhibitors of multiple mutants of Plasmodium falciparum dihydrofolate reductase and their antimalarial activities.
AID229768Ratio of Inhibition of the S108N mutant of dihydrofolate reductase (DHFR) to inhibition of wild type dihydrofolate reductase.2002Journal of medicinal chemistry, Mar-14, Volume: 45, Issue:6
Development of 2,4-diaminopyrimidines as antimalarials based on inhibition of the S108N and C59R+S108N mutants of dihydrofolate reductase from pyrimethamine-resistant Plasmodium falciparum.
AID409942Inhibition of human recombinant MAOA by fluorimetric method2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID100308Cross resistance to the compound expressed as as log of ratio of molar concentration of drug inducing 50% inhibition of growth in murine leukemia L1210/R71 and L1210/0 cells1990Journal of medicinal chemistry, Jul, Volume: 33, Issue:7
Structure-activity relationships of antineoplastic agents in multidrug resistance.
AID58251Binding affinity towards mutant dihydrofolate reductase (N51I+C59R+S108N+I164L DHFR) of Plasmodium falciparum2004Journal of medicinal chemistry, Jan-29, Volume: 47, Issue:3
Inhibitors of multiple mutants of Plasmodium falciparum dihydrofolate reductase and their antimalarial activities.
AID1797767Inhibitor Screening Using Bacterial System (IC50) and Measurement of Inhibition Constant (Ki) from Article 10.1128/AAC.00448-06: \\Evaluation of the activities of pyrimethamine analogs against Plasmodium vivax and Plasmodium falciparum dihydrofolate reduct2006Antimicrobial agents and chemotherapy, Nov, Volume: 50, Issue:11
Evaluation of the activities of pyrimethamine analogs against Plasmodium vivax and Plasmodium falciparum dihydrofolate reductase-thymidylate synthase using in vitro enzyme inhibition and bacterial complementation assays.
AID493017Wombat Data for BeliefDocking2002Journal of medicinal chemistry, Mar-14, Volume: 45, Issue:6
Development of 2,4-diaminopyrimidines as antimalarials based on inhibition of the S108N and C59R+S108N mutants of dihydrofolate reductase from pyrimethamine-resistant Plasmodium falciparum.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (19)

TimeframeStudies, This Drug (%)All Drugs %
pre-199010 (52.63)18.7374
1990's3 (15.79)18.2507
2000's6 (31.58)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: 24.61

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 Index24.61 (24.57)
Research Supply Index3.14 (2.92)
Research Growth Index4.41 (4.65)
Search Engine Demand Index26.67 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (24.61)

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%
Other22 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]