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Pyrimethamine

Pyrimethamine
Pyrimethamine2DACS.svg
Pyrimethamine-3D-balls.png
Clinical data
Pronunciation /ˌpɪrˈmɛθəmin/
Trade names Daraprim
AHFS/Drugs.com Monograph
MedlinePlus a601050
Pregnancy
category
  • AU: B3
  • US: C (Risk not ruled out)
Routes of
administration
By mouth
ATC code P01BD01 (WHO)
QP51AX51 (WHO) (combinations)
Legal status
Legal status
Pharmacokinetic data
Bioavailability well-absorbed
Protein binding 87%
Metabolism Liver
Biological half-life 96 hours
Excretion Kidney
Identifiers
CAS Number 58-14-0 YesY
PubChem (CID) 4993
IUPHAR/BPS 4800
DrugBank DB00205 YesY
ChemSpider 4819 YesY
UNII Z3614QOX8W YesY
KEGG D00488 YesY
ChEBI CHEBI:8673 YesY
ChEMBL CHEMBL36 YesY
PDB ligand ID CP6 (PDBe, RCSB PDB)
ECHA InfoCard 100.000.331
Chemical and physical data
Formula C12H13ClN4
Molar mass 248.71 g/mol
3D model (Jmol) Interactive image
  

Pyrimethamine, sold under the trade name Daraprim, is a medication used with leucovorin to treat toxoplasmosis and cystoisosporiasis. It is also used with dapsone as a second line option to prevent Pneumocystis jiroveci pneumonia (PCP) in people with HIV/AIDS. It was previously used for malaria but is no longer recommended due to resistance. Pyrimethamine is taken by mouth.

Common side effects include gastrointestinal upset, severe allergic reactions, bone marrow suppression. It should not be used in people with folate deficiency that has resulted in anemia. There is concern that it may increase the risk of cancer. While occasionally used in pregnancy it is unclear if pyrimethamine is safe for the baby. Pyrimethamine is classified as a folic acid antagonist. It works by inhibition folic acid metabolism and therefore the making of DNA.

Pyrimethamine was discovered in 1952 and came into medical use in 1953. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. In the United States in 2015 it was not available as a generic medication and the price was increased from 13.50 USD to 750 USD a tablet (75,000 USD for a course of treatment). In other areas of the world it is available as a generic and costs as little as 0.05 to 0.10 USD per dose.

Pyrimethamine is typically given with a sulfonamide and folinic acid.


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