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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL36
CHEMBL36
Compound Name PYRIMETHAMINE
ChEMBL Synonyms GNF-Pf-5586 | DARAPRIM | PYRIMETHAMINE | Malacide | Chloridin
Max Phase 4 (Approved)
Trade Names DARAPRIM | Chloridin | Malacide
Molecular Formula C12H13ClN4

Additional synonyms for CHEMBL36 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CCc1nc(N)nc(N)c1c2ccc(Cl)cc2
Standard InChI InChI=1S/C12H13ClN4/c1-2-9-10(11(14)17-12(15)16-9)7-3-5-8(13 ...
Download InChI
Standard InChI Key WKSAUQYGYAYLPV-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • Drugs for Neglected Diseases Initiative (DNDi)
  • GSK Malaria Screening
  • Harvard Malaria Screening
  • Manually Added Drugs
  • Novartis Malaria Screening
  • Open Source Malaria Screening
  • Orange Book
  • PubChem BioAssays
  • Sanger Institute Genomics of Drug Sensitivity in Cancer
  • Scientific Literature
  • St Jude Leishmania Screening
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL36

Molecule Features

CHEMBL36 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:N Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Dihydrofolate reductase inhibitor Dihydrofolate reductase DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Malaria, FalciparumD016778EFO:0007444Plasmodium falciparum malaria3ClinicalTrials
Sandhoff DiseaseD012497Orphanet:796Sandhoff disease1ClinicalTrials
Tay-Sachs DiseaseD013661Orphanet:845Tay-Sachs disease1ClinicalTrials
PregnancyD011247EFO:0002950pregnancy3ClinicalTrials
Toxoplasmosis, CongenitalD014125EFO:0007220congenital toxoplasmosis3ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-CellD015451EFO:0000095chronic lymphocytic leukemia1ClinicalTrials
MalariaD008288EFO:0001068malaria3ClinicalTrials
Toxoplasmosis, OcularD014126EFO:0007399ocular toxoplasmosis3ClinicalTrials
Amyotrophic Lateral SclerosisD000690EFO:0001356familial amyotrophic lateral sclerosis1ClinicalTrials
Myelodysplastic SyndromesD009190EFO:0000198myelodysplastic syndrome1ClinicalTrials
ToxoplasmosisD014123EFO:0007517toxoplasmosis1ClinicalTrials
Toxoplasmosis, CerebralD016781EFO:0007200cerebral toxoplasmosis2ClinicalTrials
AnemiaD000740EFO:0004272anemia3ClinicalTrials
Leukemia, LymphoidD007945EFO:0004289lymphoid leukemia1ClinicalTrials
Malaria, VivaxD016780EFO:0007445Plasmodium vivax malaria3ClinicalTrials
SchistosomiasisD012552EFO:1001475schistosomiasis3ClinicalTrials

Clinical Data

ClinicalTrials.gov PYRIMETHAMINE
The Cochrane Collaboration PYRIMETHAMINE

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL36. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL1939 Dihydrofolate reductase Plasmodium falciparum K1 1.000
CHEMBL2363 Dihydrofolate reductase Rattus norvegicus 1.000
CHEMBL2425 Dihydrofolate reductase Toxoplasma gondii 1.000
CHEMBL1926 Dihydrofolate reductase Pneumocystis carinii 1.000
CHEMBL202 Dihydrofolate reductase Homo sapiens 1.000
CHEMBL2329 Dihydrofolate reductase Candida albicans 1.000
CHEMBL4616 Ghrelin receptor Homo sapiens 1.000
CHEMBL5441 Dihydrofolate reductase Escherichia coli 1.000
CHEMBL1681620 Dihydrofolate reductase Staphylococcus aureus 1.000
CHEMBL4005 PI3-kinase p110-alpha subunit Homo sapiens 0.499
CHEMBL5457 Dihydrofolate reductase Mycobacterium avium 0.297



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL1939 Dihydrofolate reductase Plasmodium falciparum K1 1.000
CHEMBL2363 Dihydrofolate reductase Rattus norvegicus 1.000
CHEMBL2425 Dihydrofolate reductase Toxoplasma gondii 1.000
CHEMBL1926 Dihydrofolate reductase Pneumocystis carinii 1.000
CHEMBL2329 Dihydrofolate reductase Candida albicans 1.000
CHEMBL202 Dihydrofolate reductase Homo sapiens 1.000
CHEMBL5457 Dihydrofolate reductase Mycobacterium avium 1.000
CHEMBL5441 Dihydrofolate reductase Escherichia coli 1.000
CHEMBL4616 Ghrelin receptor Homo sapiens 1.000
CHEMBL1681620 Dihydrofolate reductase Staphylococcus aureus 1.000
CHEMBL4005 PI3-kinase p110-alpha subunit Homo sapiens 0.616
CHEMBL3880 Heat shock protein HSP 90-alpha Homo sapiens 0.237
CHEMBL3356 Cytochrome P450 1A2 Homo sapiens 0.201

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
248.7 248.0829 2.52 2 77.82 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
4 2 0 4 4 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 7.17 2.75 2.55 2 17 0.86

Structural Alerts

There are 1 structural alerts for CHEMBL36. To view alerts please click here.

Compound Cross References

ATC P - ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
P01 - ANTIPROTOZOALS
P01B - ANTIMALARIALS
P01BD - Diaminopyrimidines
P01BD01 - pyrimethamine

P - ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
P01 - ANTIPROTOZOALS
P01B - ANTIMALARIALS
P01BD - Diaminopyrimidines
P01BD51 - pyrimethamine, combinations

ChemSpider ChemSpider:WKSAUQYGYAYLPV-UHFFFAOYSA-N
DailyMed pyrimethamine
PubChem SID: 104171273 SID: 11112140 SID: 124881960 SID: 124881963 SID: 124881964 SID: 144203883 SID: 144209032 SID: 144210449 SID: 162163291 SID: 170464930 SID: 17389746 SID: 174006175 SID: 26747011 SID: 26747012 SID: 26751532 SID: 50100376 SID: 50104113 SID: 56422411 SID: 69611 SID: 855854
Wikipedia Pyrimethamine

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL36



ACToR 58-14-0
BindingDB 18512
Brenda 13930 761
ChEBI 8673
ChemicalBook CB8461315
DrugBank DB00205
DrugCentral 2332
eMolecules 511729
EPA CompTox Dashboard DTXSID9021217
FDA SRS Z3614QOX8W
Guide to Pharmacology 4800
Human Metabolome Database HMDB0014350
IBM Patent System 78D445EA758D773909945418B29EDF17
KEGG Ligand C07391
LINCS LSM-3967
MolPort MolPort-001-783-655
NIH Clinical Collection SAM002554921
Nikkaji J4.589F
PDBe CP6
PharmGKB PA451193
PubChem 4993
PubChem: Drugs of the Future 22395175
PubChem: Thomson Pharma 15221150
Selleck Pyrimethamine
SureChEMBL SCHEMBL25129
ZINC ZINC000000057464

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/WKSAUQYGYAYLPV-UHFFFAOYSA-N spacer
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