Record Information
Version3.6
Creation Date2012-09-06 15:16:49 UTC
Update Date2013-02-09 00:31:19 UTC
HMDB IDHMDB14350
Secondary Accession NumbersNone
Metabolite Identification
Common NamePyrimethamine
DescriptionPyrimethamine is only found in individuals that have used or taken this drug. It is one of the folic acid antagonists that is used as an antimalarial or with a sulfonamide to treat toxoplasmosis. [PubChem]Pyrimethamine inhibits the dihydrofolate reductase of plasmodia and thereby blocks the biosynthesis of purines and pyrimidines, which are essential for DNA synthesis and cell multiplication. This leads to failure of nuclear division at the time of schizont formation in erythrocytes and liver.
Structure
Thumb
Synonyms
  1. CD
  2. Chloridin
  3. Chloridine
  4. Chloridyn
  5. Diaminopyritamin
  6. Ethylpyrimidine
  7. Pirimetamin
  8. Pirimetamina
  9. Primethamine
  10. Pyremethamine
  11. Pyrimethamin
Chemical FormulaC12H13ClN4
Average Molecular Weight248.711
Monoisotopic Molecular Weight248.082874143
IUPAC Name5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine
Traditional IUPAC Namepyrimethamine
CAS Registry Number58-14-0
SMILES
CCC1=C(C(N)=NC(N)=N1)C1=CC=C(Cl)C=C1
InChI Identifier
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)
InChI KeyWKSAUQYGYAYLPV-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassDiazines
Sub ClassPyrimidines and Pyrimidine Derivatives
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Chlorobenzenes
  • Pyrimidines and Pyrimidine Derivatives
  • aminopyrimidine(ChEBI)
Substituents
  • Aryl Chloride
  • Organochloride
  • Polyamine
Direct ParentAminopyrimidines and Derivatives
Ontology
StatusExpected and Not Quantified
Origin
  • Drug
Biofunction
  • Antimalarials
  • Antiprotozoal Agents
  • Antiprotozoals
  • Folic Acid Antagonists
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point233.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.79e-01 g/LNot Available
LogP2.7Not Available
Predicted Properties
PropertyValueSource
water solubility0.18 g/LALOGPS
logP2.62ALOGPS
logP2.75ChemAxon
logS-3.1ALOGPS
pKa (strongest acidic)17.22ChemAxon
pKa (strongest basic)7.77ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count2ChemAxon
polar surface area77.82ChemAxon
rotatable bond count2ChemAxon
refractivity71.54ChemAxon
polarizability25.79ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00205
  • Not Applicable
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00205
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00205
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4819
KEGG Compound IDC07391
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPyrimethamine
NuGOwiki LinkHMDB14350
Metagene LinkHMDB14350
METLIN IDNot Available
PubChem Compound4993
PDB IDCP6
ChEBI ID8673
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sirichaiwat C, Intaraudom C, Kamchonwongpaisan S, Vanichtanankul J, Thebtaranonth Y, Yuthavong Y: Target guided synthesis of 5-benzyl-2,4-diamonopyrimidines: their antimalarial activities and binding affinities to wild type and mutant dihydrofolate reductases from Plasmodium falciparum. J Med Chem. 2004 Jan 15;47(2):345-54. Pubmed: 14711307
  2. Gatton ML, Martin LB, Cheng Q: Evolution of resistance to sulfadoxine-pyrimethamine in Plasmodium falciparum. Antimicrob Agents Chemother. 2004 Jun;48(6):2116-23. Pubmed: 15155209

Enzymes

Gene Name:
DHFR
Uniprot ID:
P00374
Gene Name:
CYP2C9
Uniprot ID:
P11712
Gene Name:
CYP2D6
Uniprot ID:
P10635
Gene Name:
CYP2C8
Uniprot ID:
P10632