Tafenoquine

Tafenoquine
Clinical data
Pronunciation	ta fen' oh kwin
Trade names	Krintafel, Arakoda, others
Other names	Etaquine, WR 238605, SB-252263
AHFS/Drugs.com	Monograph
MedlinePlus	a618050
License data	US DailyMed: Tafenoquine;
Pregnancy; category	AU: C;
Routes of; administration	By mouth
Drug class	Antimalarial
ATC code	P01BA07 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); US: ℞-only;
Identifiers
	IUPAC name N-[2,6-Dimethoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]quinolin-8-yl]pentane-1,4-diamine;
CAS Number	106635-80-7 ;
PubChem CID	115358;
DrugBank	DB06608 ;
ChemSpider	103196 ;
UNII	262P8GS9L9;
KEGG	D10490 ; as salt: D10670 ;
ChEBI	CHEBI:135752;
ChEMBL	ChEMBL298470 ;
NIAID ChemDB	006901;
CompTox Dashboard (EPA)	DTXSID90869466 ;
Chemical and physical data
Formula	C24H28F3N3O3
Molar mass	463.501 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES FC(F)(F)c3cc(Oc1c(OC)cc(NC(C)CCCN)c2nc(OC)cc(c12)C)ccc3;
	InChI InChI=1S/C24H28F3N3O3/c1-14-11-20(32-4)30-22-18(29-15(2)7-6-10-28)13-19(31-3)23(21(14)22)33-17-9-5-8-16(12-17)24(25,26)27/h5,8-9,11-13,15,29H,6-7,10,28H2,1-4H3 ; Key:LBHLFPGPEGDCJG-UHFFFAOYSA-N ;
	(what is this?) (verify)

Tafenoquine, sold under the brand name Krintafel among others, is a medication used to prevent and to treat malaria. With respect to acute malaria, it is used together with other medications to prevent relapse by Plasmodium vivax. It may be used to prevent all types of malaria. It is taken by mouth.

Common side effects include vomiting, headache, and dizziness. Other side effects may include methemoglobinemia, trouble sleeping, and anaphylaxis. In people with G6PD deficiency, red blood cell breakdown may occur. Use in pregnancy is not recommended. Tafenoquine is in the 8-aminoquinoline family of medications. The mechanism of action is unclear but it is effective both in the liver and bloodstream. A possible mechanism of action and other novel perspectives have been published.

Tafenoquine was approved for medical use in Australia and in the United States in 2018. Tafenoquine is related to primaquine.