PYRIMETHAMINE

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Trade Names
Synonyms
Status
Molecule Category Free-form
ATC P01BD01
UNII Z3614QOX8W
EPA CompTox DTXSID9021217

Structure

InChI Key WKSAUQYGYAYLPV-UHFFFAOYSA-N
Smiles CCc1nc(N)nc(N)c1-c1ccc(Cl)cc1
InChI
InChI=1S/C12H13ClN4/c1-2-9-10(11(14)17-12(15)16-9)7-3-5-8(13)6-4-7/h3-6H,2H2,1H3,(H4,14,15,16,17)

Physicochemical Descriptors

Property Name Value
Molecular Formula C12H13ClN4
Molecular Weight 248.72
AlogP 2.52
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 2.0
Polar Surface Area 77.82
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 17.0

Pharmacology

Mechanism of Action Action Reference
Dihydrofolate reductase inhibitor INHIBITOR DailyMed Wikipedia
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Oxidoreductase
- 25.5-760 1.4-16 0.19-860 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 72.59-107.42
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC47 family of multidrug and toxin extrusion transporters
- - - 145 -
Unclassified protein
- - - 0.85 -
EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Babesia gibsoni
- 50 - - -
Bos taurus
- 100.7-100.7 - - -
Cricetulus griseus
- - - - 72.59-107.42
Enterococcus faecium
- 8 - - -
Escherichia coli
- - 1.4-16 1.2-281.84 -
Homo sapiens
- 4.22-760 - 28.2-470 -
Lactobacillus casei
- 240 - - -
Leishmania major
- - - 250 68
Leishmania mexicana
- - - - 50-102.5
Mus musculus
- - - 145 -
Mycobacterium avium
- 150 - - -
Mycobacterium smegmatis
- - - 75 -
Mycobacterium tuberculosis H37Rv
- - - - 26.7-95.6
Plasmodium falciparum
18-100 0.028-870 - 0.19-860 25-100
Plasmodium falciparum 3D7
- 2.1-47 - - -
Plasmodium falciparum D10
- 70 - - -
Plasmodium falciparum D6
- 9-10 - - -
Plasmodium falciparum Dd2
- - - - 62
Plasmodium falciparum FCR-3/Gambia
- 12 - - -
Plasmodium falciparum NF54
- 28-45 - - -
Pneumocystis carinii
- 0 - 9.7 -
Pneumocystis jirovecii
- 130 - - -
Respiratory syncytial virus
750 - - - -
Toxoplasma gondii
210-290 0-800 - - -
Toxoplasma gondii PRU
- 800 - - -
Toxoplasma gondii RH
340-680 120-240 - - -
Trypanosoma brucei
- 90 - 11 -
Trypanosoma cruzi
- - - 98 -

Cross References

Resources Reference
CAS NUMBER 58-14-0
ChEBI 8673
ChEMBL CHEMBL36
DrugBank DB00205
DrugCentral 2332
FDA SRS Z3614QOX8W
Human Metabolome Database HMDB0014350
Guide to Pharmacology 4800
KEGG C07391
PDB CP6
PharmGKB PA451193
PubChem 4993
SureChEMBL SCHEMBL25129
ZINC ZINC000000057464
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