Tafenoquine

Tafenoquine

File:Tafenoquine.svg
Systematic (IUPAC) name
N-[2,6-Dimethoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]quinolin-8-yl]pentane-1,4-diamine
Identifiers
CAS Number	106635-80-7 N
ATC code	none
PubChem	CID: 115358
ChemSpider	103196 Y
UNII	262P8GS9L9 Y
ChEMBL	CHEMBL298470 Y
NIAID ChemDB	006901
Synonyms	Etaquine, WR 238605, SB-252263
Chemical data
Formula	C24H28F3N3O3
Molecular mass	463.493 g/mol
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 Y Key:LBHLFPGPEGDCJG-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Tafenoquine is an 8-aminoquinoline drug manufactured by GlaxoSmithKline that is being investigated as a potential treatment for malaria, as well as for malaria prevention.

The proposed indication for tafenoquine is for treatment of the hypnozoite stages of Plasmodium vivax and Plasmodium ovale that are responsible for relapse of these malaria species even when the blood stages are successfully cleared. This is only now achieved by administration of daily primaquine for 14 days. The main advantage of tafenoquine is that it has a long half-life (2–3 weeks) and therefore a single treatment may be sufficient to clear hypnozoites. The shorter regimen has been described as an advantage.

Like primaquine, tafenoquine causes hemolysis in people with G-6-P deficiency. Indeed, the long half-life of tafenoquine suggests that particular care should be taken to ensure that individuals with severe G-6-P deficiency do not receive the drug.

The dose of tafenoquine has not been firmly established, but for the treatment of Plasmodium vivax malaria, a dose of 800 mg over three days has been used.