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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 | Malacide | Daraprim | Pyrimethamine | Chloridin
Max Phase 4 (Approved)
Trade Names Daraprim | Malacide | Chloridin
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

Mechanism of Action

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

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

Clinical Data

Number of clinical trials registered at clinicaltrials.gov
Number of reviews at The Cochrane Collaboration
Number of entries at British National Formulary

Structural Alerts

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

Alternate Forms of Compound in ChEMBL


CHEMBL36

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
CHEMBL4616 Ghrelin receptor Homo sapiens 1.000
CHEMBL2329 Dihydrofolate reductase Candida albicans 1.000
CHEMBL5441 Dihydrofolate reductase Escherichia coli 0.949
CHEMBL1681620 Dihydrofolate reductase Staphylococcus aureus 0.656
CHEMBL230 Cyclooxygenase-2 Homo sapiens 0.368
CHEMBL5457 Dihydrofolate reductase Mycobacterium avium 0.293



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
CHEMBL5457 Dihydrofolate reductase Mycobacterium avium 1.000
CHEMBL202 Dihydrofolate reductase Homo sapiens 1.000
CHEMBL4616 Ghrelin receptor Homo sapiens 1.000
CHEMBL5441 Dihydrofolate reductase Escherichia coli 0.997
CHEMBL1681620 Dihydrofolate reductase Staphylococcus aureus 0.707
CHEMBL3356 Cytochrome P450 1A2 Homo sapiens 0.266

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
248.7 248.0829 2.75 2 77.81 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
- 7.18 2.75 2.55 2 17 0.86

Compound Cross References

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

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

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: 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
ChEBI 8673
DrugBank DB00205
eMolecules 511729
FDA SRS Z3614QOX8W
Guide to Pharmacology 4800
Human Metabolome Database HMDB14350
IBM Patent System 78D445EA758D773909945418B29EDF17
KEGG Ligand C07391
LINCS LSM-3967
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 ZINC00057464

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