Tafenoquine

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]

Tafenoquine
Clinical data
Pronunciationta fen' oh kwin
Trade namesKrintafel, Arakoda, others
Other namesEtaquine,[1] WR 238605,[1] SB-252263
AHFS/Drugs.comMonograph
MedlinePlusa618050
License data
Pregnancy
category
Routes of
administration		By mouth
Drug classAntimalarial
ATC code
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
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
Chemical and physical data
FormulaC24H28F3N3O3
Molar mass463.501 g·mol−1
3D model (JSmol)
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)

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]

Medical use

Prevention

Tafenoquine may be used to prevent all types of malaria.[3] For this use 200 mg 3 days before travel then 200 mg per week until one week after travel is recommended.[7]

Treatment

Tafenoquine is used for eliminating the hypnozoite stage of Plasmodium vivax and Plasmodium ovale that is responsible for relapse of these malarial infections, even when the blood stages are successfully cleared. Primaquine for 14 days can also be used for this. The advantage of tafenoquine is that it has a long half-life (2–3 weeks) and therefore a single treatment is sufficient.[8] For this use, a single dose of 300 mg is recommended.[7] It is used with another medication, such as chloroquine, that kills the parasites in the bloodstream.[9]

There is a need to determine whether or not tafenoquine kills the numerous, non-circulating asexual P. vivax parasites that are now known to occur in the spleen, bone marrow, and possibly elsewhere in chronic infections.[10]

Chemistry

Tafenoquine contains a stereocenter and consists of two enantiomers. This is a mixture of (R) - and the (S) - Form:

Enantiomers of tafenoquine

(R)-Form
(S)-Form

History

Tafenoquine was approved for medical use in Australia and in the United States in 2018.[3][6] Tafenoquine was given an orphan drug designation and was granted breakthrough therapy status in 2013 in the United States.[11][12]

Society and culture

One version is made by GlaxoSmithKline.[4] While another is made by 60 Degrees Pharmaceutical.[13]

Names

Etaquine was a generic name proposed by WRAIR, and subsequently rejected by CDER.

Trade names

References
  1. Peters W (1999). "The evolution of tafenoquine--antimalarial for a new millennium?". J R Soc Med. 92 (7): 345–352. doi:10.1177/014107689909200705. PMC 1297286. PMID 10615272.
  2. Use During Pregnancy and Breastfeeding
  3. Haston JC, Hwang J, Tan KR (November 2019). "Guidance for Using Tafenoquine for Prevention and Antirelapse Therapy for Malaria — United States, 2019" (PDF). MMWR. Morbidity and Mortality Weekly Report. 68 (46): 1062–1068. doi:10.15585/mmwr.mm6846a4. PMC 6871897. PMID 31751320.
  4. "Tafenoquine Succinate (Krintafel) Monograph for Professionals". Drugs.com. Retrieved 22 November 2019.
  5. Markus, Miles B. (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.
  6. Hounkpatin, Aurore B; Kreidenweiss, Andrea; Held, Jana (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.
  7. "Tafenoquine Approved for Malaria Prophylaxis and Treatment". Centers for Disease Control and Prevention (CDC). 25 April 2019. Retrieved 22 November 2019.
  8. Elmes NJ, Nasveld PE, Kitchener SJ, Kocisko DA, Edstein MD (November 2008). "The efficacy and tolerability of three different regimens of tafenoquine versus primaquine for post-exposure prophylaxis of Plasmodium vivax malaria in the Southwest Pacific". Transactions of the Royal Society of Tropical Medicine and Hygiene. 102 (11): 1095–101. doi:10.1016/j.trstmh.2008.04.024. PMID 18541280.
  9. "Conclusions and Recommendations from the Fifteenth Meeting of the WHO Advisory Committee on Safety of Medicinal Products (ACSoMP)" (PDF). WHO. Retrieved 22 November 2019.
  10. Markus, MB (2019). "Killing of Plasmodium vivax by primaquine and tafenoquine". Trends in Parasitology. 35 (11): 857–859. doi:10.1016/j.pt.2019.08.009. PMID 31522991. S2CID 202582476.
  11. "Krintafel (tafenoquine succinate tablets) FDA Advisory Committee Briefing Document" (PDF). Food and Drug Administration. 12 July 2018. Archived from the original on 23 November 2019. Retrieved 22 November 2019.
  12. "Krintafel Orphan Drug Designation and Approval". U.S. Food and Drug Administration (FDA). Archived from the original on 23 November 2019. Retrieved 22 November 2019.
  13. Tan, Kathrine R; Hwang, Jimee (2018). "Tafenoquine receives regulatory approval in USA for prophylaxis of malaria and radical cure of Plasmodium vivax". Journal of Travel Medicine. 25 (1). doi:10.1093/jtm/tay071. PMID 30137454.
  14. "Kozenis (tafenoquine) approved by the Australian Therapeutic Goods Administration for the radical cure of P. vivax malaria" (Press release). Medicines for Malaria Venture. 21 September 2018. Retrieved 15 October 2018.
  15. "Kodatef". NPS MedicineWise.
  16. "Drug Approval Package: Arakoda". U.S. Food and Drug Administration (FDA). 13 February 2019. Archived from the original on 23 November 2019. Retrieved 22 November 2019.
  17. "Drug Approval Package: Krintafel (tafenoquine)". U.S. Food and Drug Administration (FDA). 24 August 2018. Archived from the original on 23 November 2019. Retrieved 22 November 2019.
  18. "Drug Trials Snapshots: Krintafel". U.S. Food and Drug Administration (FDA). 6 August 2018. Archived from the original on 23 November 2019. Retrieved 22 November 2019.
  19. "US FDA approves Krintafel (tafenoquine) for the radical cure of P. vivax malaria" (Press release). Medicines for Malaria Venture. 20 July 2018. Retrieved 15 October 2018.
  • "Tafenoquine". Drug Information Portal. U.S. National Library of Medicine.
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