Clinical data | |
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Pronunciation | /ˌpɪrᵻˈmɛθəmin/ |
Trade names | Daraprim |
AHFS/Drugs.com | Monograph |
MedlinePlus | a601050 |
Pregnancy category |
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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 | |
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CAS Number | 58-14-0 |
PubChem (CID) | 4993 |
IUPHAR/BPS | 4800 |
DrugBank | DB00205 |
ChemSpider | 4819 |
UNII | Z3614QOX8W |
KEGG | D00488 |
ChEBI | CHEBI:8673 |
ChEMBL | CHEMBL36 |
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 |
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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.