Substance
ID:90
Names and Identifiers
Synonyms
PyrimethamineChloridinChloridineEthylpyrimidinePrimethaminePirimetaminaChloridynDiaminopyritaminCDPirimetaminPyrimethamine HclPyremethaminePyrimethamin
IUPAC Traditional name
pyrimethamine
IUPAC name
5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine
Brand Name
DaraprimErbaprelinaMalocidMalocideTindurinMalacidPirimecidanTinduringDisuloneKhloridinDarachlorDaraprimeMaloprimDaraclorDarapramFansidar
Properties
Physical Property
Hydrophobicity(logP)
2.7
Solubility
121 mg/L
Molecule Details
Drug Groups
approved
Description
One of the folic acid antagonists that is used as an antimalarial or with a sulfonamide to treat toxoplasmosis. [PubChem]
Indication
For the treatment of toxoplasmosis and acute malaria; For the prevention of malaria in areas non-resistant to pyrimethamine
Pharmacology
Pyrimethamine is an antiparasitic compound commonly used as an adjunct in the treatment of uncomplicated, chloroquine resistant, P. falciparum malaria. Pyrimethamine is a folic acid antagonist and the rationale for its therapeutic action is based on the differential requirement between host and parasite for nucleic acid precursors involved in growth. This activity is highly selective against plasmodia and Toxoplasma gondii. Pyrimethamine possesses blood schizonticidal and some tissue schizonticidal activity against malaria parasites of humans. However, the 4-amino-quinoline compounds are more effective against the erythrocytic schizonts. It does not destroy gametocytes, but arrests sporogony in the mosquito. The action of pyrimethamine against Toxoplasma gondii is greatly enhanced when used in conjunction with sulfonamides.
Affected Organisms
Plasmodium
Biotransformation
Hepatic
Absorption
Well absorbed with peak levels occurring between 2 to 6 hours following administration
Half Life
96 hours
Protein Binding
87%
References
•
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]
•
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]
External Links
Molecular Spectra
No Data Available
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References
• 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
• 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