Pyrimethamine

Pyrimethamine
Clinical data
Pronunciation	/ˌpɪrɪˈmɛθəmɪn/
Trade names	Daraprim, others
AHFS/Drugs.com	Monograph
MedlinePlus	a601050
License data	US DailyMed: Pyrimethamine; US FDA: Pyrimethamine;
Pregnancy; category	AU: B3;
Routes of; administration	By mouth
ATC code	P01BD01 (WHO) ; QP51AX51 (WHO) (combinations);
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	well-absorbed
Protein binding	87%
Metabolism	Liver
Elimination half-life	96 hours
Excretion	Kidney
Identifiers
	IUPAC name 5-(4-chlorophenyl)-6-ethyl- 2,4-pyrimidinediamine;
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	CP6 (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID9021217 ;
ECHA InfoCard	100.000.331
Chemical and physical data
Formula	C12H13ClN4
Molar mass	248.71 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	233 to 234 °C (451 to 453 °F)
	SMILES Clc2ccc(c1c(nc(nc1CC)N)N)cc2;
	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) ; Key:WKSAUQYGYAYLPV-UHFFFAOYSA-N ;
	(verify)

Pyrimethamine, sold under the brand name Daraprim among others, is a medication used with leucovorin (leucovorin is used to decrease side effects of pyrimethamine; it does not have intrinsic anti-parasitic activity) to treat the parasitic diseases toxoplasmosis and cystoisosporiasis. It is also used with dapsone as a second-line option to prevent Pneumocystis jiroveci pneumonia 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, and bone marrow suppression. It should not be used by 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 inhibiting 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. It was approved as a generic in the United States in February 2020.

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