Compounds > 2,4-diamino-5-phenyl-6-methylpyrimidine
Page last updated: 2024-12-06

2,4-diamino-5-phenyl-6-methylpyrimidine

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

Description

2,4-diamino-5-phenyl-6-methylpyrimidine: analog of pyrimethamine; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID72565
CHEMBL ID21408
SCHEMBL ID3500167
MeSH IDM0046358

Synonyms (23)

Synonym
nsc 115191
brn 0012007
2,4-diamino-6-methyl-5-phenylpyrimidine
2,4-diamino-5-phenyl-6-methylpyrimidine
2,4-pyrimidinediamine, 6-methyl-5-phenyl-
pyrimidine, 2,4-diamino-6-methyl-5-phenyl-
6-methyl-5-phenyl-2,4-pyrimidinediamine
nsc-115191
18588-50-6
2, 6-methyl-5-phenyl-
nsc115191
iem-687
pyrimidine,4-diamino-6-methyl-5-phenyl-
6-methyl-5-phenylpyrimidine-2,4-diamine
chembl21408 ,
bdbm18789
AKOS015776702
unii-0s5bj6m980
0s5bj6m980 ,
SCHEMBL3500167
DTXSID60171806
F2185-0918
diamino-5-phenyl-6-methylpyrimidine, 2,4-
[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)Ki0.01330.00020.00520.0225AID1797767
Bifunctional dihydrofolate reductase-thymidylate synthasePlasmodium falciparum K1IC50 (µMol)30.80000.00151.11635.8000AID157842
Bifunctional dihydrofolate reductase-thymidylate synthasePlasmodium falciparum K1Ki0.04580.00000.43696.6645AID238767; AID58253; AID58254; AID58255
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (16)

Assay IDTitleYearJournalArticle
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.
AID288307Inhibition of human DHFR expressed in Saccharomyces cerevisiae TB5 assessed as yeast growth inhibition after 3 days by radial spoke assay2007Bioorganic & medicinal chemistry, Jul-01, Volume: 15, Issue:13
Structure-based design, synthesis and preliminary evaluation of selective inhibitors of dihydrofolate reductase from Mycobacterium tuberculosis.
AID288308Inhibition of yeast DHFR expressed in Saccharomyces cerevisiae TB5 assessed as yeast growth inhibition by after 3 days by radial spoke assay2007Bioorganic & medicinal chemistry, Jul-01, Volume: 15, Issue:13
Structure-based design, synthesis and preliminary evaluation of selective inhibitors of dihydrofolate reductase from Mycobacterium tuberculosis.
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.
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.
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.
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.
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.
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.
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.
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.
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.
AID288306Inhibition of Mycobacterium tuberculosis DHFR expressed in Saccharomyces cerevisiae TB5 assessed as yeast growth inhibition after 3 days by radial spoke assay2007Bioorganic & medicinal chemistry, Jul-01, Volume: 15, Issue:13
Structure-based design, synthesis and preliminary evaluation of selective inhibitors of dihydrofolate reductase from Mycobacterium tuberculosis.
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.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (20.00)18.7374
1990's0 (0.00)18.2507
2000's4 (80.00)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: 12.34

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 Index12.34 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.14 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.34)

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%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
pyrimethamine
Maloprim: contains above 2 cpds		2.940aminopyrimidine;
monochlorobenzenes		antimalarial;
antiprotozoal drug;
EC 1.5.1.3 (dihydrofolate reductase) inhibitor
trimethoprim
Trimethoprim: A pyrimidine inhibitor of dihydrofolate reductase, it is an antibacterial related to PYRIMETHAMINE. It is potentiated by SULFONAMIDES and the TRIMETHOPRIM, SULFAMETHOXAZOLE DRUG COMBINATION is the form most often used. It is sometimes used alone as an antimalarial. TRIMETHOPRIM RESISTANCE has been reported.. trimethoprim : An aminopyrimidine antibiotic whose structure consists of pyrimidine 2,4-diamine and 1,2,3-trimethoxybenzene moieties linked by a methylene bridge.		2.4220aminopyrimidine;
methoxybenzenes		antibacterial drug;
diuretic;
drug allergen;
EC 1.5.1.3 (dihydrofolate reductase) inhibitor;
environmental contaminant;
xenobiotic
cycloguanil
cycloguanil: the active metabolite of proguanil; antifolate drug; structure in first source. cycloguanil : A triazine in which a 1,6-dihydro-1,3,5-triazine ring is substituted at N-1 by a 4-chlorophenyl group, at C-2 and -4 by amino groups and at C-6 by gem-dimethyl groups. A dihydrofolate reductase inhibitor, it is a metabolite of the antimalarial drug proguanil.		2.0210triazinesantifolate;
antiinfective agent;
antimalarial;
antiparasitic agent;
antiprotozoal drug;
EC 1.5.1.3 (dihydrofolate reductase) inhibitor
4,6-diamino-2,2-dimethyl-1,2-dihydro-1-phenyl-s-triazine
4,6-diamino-2,2-dimethyl-1,2-dihydro-1-phenyl-s-triazine: structure in first source		2.0210
etoprine
etoprine: do not confuse with 3,5-dicarbethoxy-2,6-dimethyl-4-ethyl-1,4-dihydropyridine, also called DDEP		2.7130
wr 99210
BRL 6231: RN given refers to parent cpd; NM & N1 refer to HCl; synonym BRL 51084 refers to (mono-HBr); structure		2.0210
3-amino-1-methyl-5h-pyrido(4,3-b)indole
3-amino-1-methyl-5H-pyrido(4,3-b)indole: structure		2.0210pyridoindole
ConditionIndicatedRelationship StrengthStudiesTrials
Plasmodium falciparum Malaria
[description not available]		02.0110
Malaria, Falciparum
Malaria caused by PLASMODIUM FALCIPARUM. This is the severest form of malaria and is associated with the highest levels of parasites in the blood. This disease is characterized by irregularly recurring febrile paroxysms that in extreme cases occur with acute cerebral, renal, or gastrointestinal manifestations.		02.0110
Congenital Limb Deformities
[description not available]		01.9410
Abnormalities, Multiple
Congenital abnormalities that affect more than one organ or body structure.		01.9410
Brain Damage, Chronic
A condition characterized by long-standing brain dysfunction or damage, usually of three months duration or longer. Potential etiologies include BRAIN INFARCTION; certain NEURODEGENERATIVE DISORDERS; CRANIOCEREBRAL TRAUMA; ANOXIA, BRAIN; ENCEPHALITIS; certain NEUROTOXICITY SYNDROMES; metabolic disorders (see BRAIN DISEASES, METABOLIC); and other conditions.		01.9410
Eye Abnormalities
Congenital absence of or defects in structures of the eye; may also be hereditary.		01.9410
Abnormalities, Drug-Induced
Congenital abnormalities caused by medicinal substances or drugs of abuse given to or taken by the mother, or to which she is inadvertently exposed during the manufacture of such substances. The concept excludes abnormalities resulting from exposure to non-medicinal chemicals in the environment.		01.9410
Pregnancy
The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.		01.9410