Primaquine

Primaquine
Clinical data
Other names	primaquine phosphate
AHFS/Drugs.com	Monograph
MedlinePlus	a607037
License data	US DailyMed: Primaquine;
Routes of; administration	By mouth
ATC code	P01BA03 (WHO) ;
Legal status
Legal status	US: ℞-only;
Pharmacokinetic data
Bioavailability	96%
Metabolism	Liver
Elimination half-life	6 hours
Identifiers
	IUPAC name (RS)-N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine;
CAS Number	90-34-6 ;
PubChem CID	4908;
DrugBank	DB01087 ;
ChemSpider	4739 ;
UNII	MVR3634GX1;
KEGG	D08420 ;
ChEBI	CHEBI:8405 ;
ChEMBL	ChEMBL506 ;
CompTox Dashboard (EPA)	DTXSID8023509 ;
ECHA InfoCard	100.001.807
Chemical and physical data
Formula	C15H21N3O
Molar mass	259.353 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
	SMILES O(c1cc(NC(C)CCCN)c2ncccc2c1)C;
	InChI InChI=1S/C15H21N3O/c1-11(5-3-7-16)18-14-10-13(19-2)9-12-6-4-8-17-15(12)14/h4,6,8-11,18H,3,5,7,16H2,1-2H3 ; Key:INDBQLZJXZLFIT-UHFFFAOYSA-N ;
	(verify)

Primaquine is a medication used to treat and prevent malaria and to treat Pneumocystis pneumonia. Specifically it is used for malaria due to Plasmodium vivax and Plasmodium ovale along with other medications and for prevention if other options cannot be used. It is an alternative treatment for Pneumocystis pneumonia together with clindamycin. It is taken by mouth.

Common side effects include nausea, vomiting, and stomach cramps. Primaquine should not be given to people with glucose-6-phosphate dehydrogenase (G6PD) deficiency due to the risk of red blood cell breakdown. It is often recommended that primaquine not be used during pregnancy. It may be used while breastfeeding if the baby is known not to have G6PD deficiency. The mechanisms of action is not entirely clear but is believed to involve effects on the malaria parasites' DNA.

Primaquine was first made in 1946. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication.