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;
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.^[3] With respect to acute malaria, it is used together with other medications to prevent relapse by Plasmodium vivax.^[3] It may be used to prevent all types of malaria.^[3] It is taken by mouth.^[4]

Common side effects include vomiting, headache, and dizziness.^[4] Other side effects may include methemoglobinemia, trouble sleeping, and anaphylaxis.^[4] In people with G6PD deficiency, red blood cell breakdown may occur.^[4] Use in pregnancy is not recommended.^[4] Tafenoquine is in the 8-aminoquinoline family of medications.^[3] How it works is unclear but it is effective both in the liver and bloodstream.^[4]^[3] A possible mechanism of action and other novel perspectives have been published.^[5]

Tafenoquine was approved for medical use in Australia and in the United States in 2018.^[3]^[6] Tafenoquine is related to primaquine.^[7]

^ ^a ^b Peters W (July 1999). "The evolution of tafenoquine--antimalarial for a new millennium?". Journal of the Royal Society of Medicine. 92 (7): 345–352. doi:10.1177/014107689909200705. PMC 1297286. PMID 10615272.
^ Use During Pregnancy and Breastfeeding
^ ^a ^b ^c ^d ^e ^f Haston JC, Hwang J, Tan KR (November 2019). "Guidance for Using Tafenoquine for Prevention and Antirelapse Therapy for Malaria - United States, 2019". MMWR. Morbidity and Mortality Weekly Report. 68 (46): 1062–1068. doi:10.15585/mmwr.mm6846a4. PMC 6871897. PMID 31751320.
^ ^a ^b ^c ^d ^e ^f "Tafenoquine Succinate (Krintafel) Monograph for Professionals". Drugs.com. Retrieved 22 November 2019.
^ Markus MB (2021). "Safety and Efficacy of Tafenoquine for Plasmodium vivax Malaria Prophylaxis and Radical Cure: Overview and Perspectives". Therapeutics and Clinical Risk Management. 17: 989–999. doi:10.2147/TCRM.S269336. PMC 8435617. PMID 34526770.
^ Hounkpatin AB, Kreidenweiss A, Held J (March 2019). "Clinical utility of tafenoquine in the prevention of relapse of Plasmodium vivax malaria: a review on the mode of action and emerging trial data". Infection and Drug Resistance. 12: 553–570. doi:10.2147/IDR.S151031. PMC 6411314. PMID 30881061.
^ "Tafenoquine Approved for Malaria Prophylaxis and Treatment". Centers for Disease Control and Prevention (CDC). 25 April 2019. Retrieved 22 November 2019.

[Peters1999-1] Peters W (July 1999). "The evolution of tafenoquine--antimalarial for a new millennium?". Journal of the Royal Society of Medicine. 92 (7): 345–352. doi:10.1177/014107689909200705. PMC 1297286. PMID 10615272.

[Drugs.com_Pregnancy-2] Use During Pregnancy and Breastfeeding

[Jul2019-3] ^ ^a ^b ^c ^d ^e ^f Haston JC, Hwang J, Tan KR (November 2019). "Guidance for Using Tafenoquine for Prevention and Antirelapse Therapy for Malaria - United States, 2019". MMWR. Morbidity and Mortality Weekly Report. 68 (46): 1062–1068. doi:10.15585/mmwr.mm6846a4. PMC 6871897. PMID 31751320.

[AHFS2019-4] ^ ^a ^b ^c ^d ^e ^f "Tafenoquine Succinate (Krintafel) Monograph for Professionals". Drugs.com. Retrieved 22 November 2019.

[5] Markus MB (2021). "Safety and Efficacy of Tafenoquine for Plasmodium vivax Malaria Prophylaxis and Radical Cure: Overview and Perspectives". Therapeutics and Clinical Risk Management. 17: 989–999. doi:10.2147/TCRM.S269336. PMC 8435617. PMID 34526770.

[Hou2019-6] Hounkpatin AB, Kreidenweiss A, Held J (March 2019). "Clinical utility of tafenoquine in the prevention of relapse of Plasmodium vivax malaria: a review on the mode of action and emerging trial data". Infection and Drug Resistance. 12: 553–570. doi:10.2147/IDR.S151031. PMC 6411314. PMID 30881061.

[CDC2019Travel-7] "Tafenoquine Approved for Malaria Prophylaxis and Treatment". Centers for Disease Control and Prevention (CDC). 25 April 2019. Retrieved 22 November 2019.

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