Tafenoquine Explained

Verifiedfields:changed
Watchedfields:changed
Verifiedrevid:470476706
Pronounce:ta fen' oh kwin
Tradename:Krintafel, Arakoda, others
Dailymedid:Tafenoquine
Pregnancy Au:C
Routes Of Administration:By mouth
Class:Antimalarial
Atc Prefix:P01
Atc Suffix:BA07
Legal Au:S4
Legal Us:Rx-only
Index2 Label:as salt
Cas Number:106635-80-7
Pubchem:115358
Chemspiderid:103196
Unii:262P8GS9L9
Kegg:D10490
Kegg2:D10670
Chebi:135752
Chembl:298470
Niaid Chemdb:006901
Synonyms:Etaquine,[1] WR 238605, SB-252263
Iupac Name:N-[2,6-Dimethoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]quinolin-8-yl]pentane-1,4-diamine
C:24
H:28
F:3
N:3
O:3
Smiles:FC(F)(F)c3cc(Oc1c(OC)cc(NC(C)CCCN)c2nc(OC)cc(c12)C)ccc3
Stdinchi: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
Stdinchikey:LBHLFPGPEGDCJG-UHFFFAOYSA-N

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.[2] It may be used to prevent all types of malaria.[2] It is taken by mouth.[3]

Common side effects include vomiting, headache, and dizziness.[3] Other side effects may include methemoglobinemia, trouble sleeping, and anaphylaxis.[3] In people with G6PD deficiency, red blood cell breakdown may occur.[3] Use in pregnancy is not recommended.[3] Tafenoquine is in the 8-aminoquinoline family of medications.[2] The mechanism of action is unclear but it is effective both in the liver and bloodstream.[3] [2] A possible mechanism of action and other novel perspectives have been published.[4]

Tafenoquine was approved for medical use in Australia and in the United States in 2018.[2] [5] Tafenoquine is related to primaquine.[6]

Medical use

Prevention

Tafenoquine may be used to prevent all types of malaria.[2] For this use 200 mg 3 days before travel then 200 mg per week until one week after travel is recommended.[6]

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.[7] For this use, a single dose of 300 mg is recommended.[6] It is used with another medication, such as chloroquine, that kills the parasites in the bloodstream.[8]

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.[9] [10]

Chemistry

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

History

Tafenoquine was approved for medical use in Australia and in the United States in 2018.[2] [5] 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.[3] 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

External links

Notes and References

  1. Peters W . The evolution of tafenoquine--antimalarial for a new millennium? . Journal of the Royal Society of Medicine . 92 . 7 . 345–352 . July 1999 . 10615272 . 1297286 . 10.1177/014107689909200705 .
  2. Haston JC, Hwang J, Tan KR . Guidance for Using Tafenoquine for Prevention and Antirelapse Therapy for Malaria - United States, 2019 . MMWR. Morbidity and Mortality Weekly Report . 68 . 46 . 1062–1068 . November 2019 . 31751320 . 6871897 . 10.15585/mmwr.mm6846a4 .
  3. Web site: Tafenoquine Succinate (Krintafel) Monograph for Professionals . Drugs.com . 22 November 2019 .
  4. Markus MB . Safety and Efficacy of Tafenoquine for Plasmodium vivax Malaria Prophylaxis and Radical Cure: Overview and Perspectives . Therapeutics and Clinical Risk Management . 17 . 989–999 . 2021 . 34526770 . 8435617 . 10.2147/TCRM.S269336 . free .
  5. Hounkpatin AB, Kreidenweiss A, Held J . 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 . March 2019 . 30881061 . 6411314 . 10.2147/IDR.S151031 . free .
  6. Web site: Tafenoquine Approved for Malaria Prophylaxis and Treatment . Centers for Disease Control and Prevention (CDC) . 25 April 2019 . 22 November 2019.
  7. Elmes NJ, Nasveld PE, Kitchener SJ, Kocisko DA, Edstein MD . 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 . 1095–1101 . November 2008 . 18541280 . 10.1016/j.trstmh.2008.04.024 .
  8. Web site: Conclusions and Recommendations from the Fifteenth Meeting of the WHO Advisory Committee on Safety of Medicinal Products (ACSoMP) . WHO . 22 November 2019.
  9. Markus MB . Killing of Plasmodium vivax by Primaquine and Tafenoquine . Trends in Parasitology . 35 . 11 . 857–859 . November 2019 . 31522991 . 10.1016/j.pt.2019.08.009 . 202582476 .
  10. Markus MB . Putative Contribution of 8-Aminoquinolines to Preventing Recrudescence of Malaria . Tropical Medicine and Infectious Disease . 8 . 5 . 278 . May 2023 . 37235326 . 10223033 . 10.3390/tropicalmed8050278 . free .
  11. Web site: Krintafel (tafenoquine succinate tablets) FDA Advisory Committee Briefing Document . PDF . https://web.archive.org/web/20191123044059/https://www.fda.gov/media/114270/download . . 12 July 2018 . 23 November 2019 . live . 22 November 2019.
  12. Web site: Krintafel Orphan Drug Designation and Approval . U.S. Food and Drug Administration (FDA) . https://web.archive.org/web/20191123045030/https://www.accessdata.fda.gov/scripts/opdlisting/oopd/detailedIndex.cfm?cfgridkey=385812 . 23 November 2019 . live . 22 November 2019.
  13. Tan KR, Hwang J . Tafenoquine receives regulatory approval in USA for prophylaxis of malaria and radical cure of Plasmodium vivax . Journal of Travel Medicine . 25 . 1 . January 2018 . 30137454 . 10.1093/jtm/tay071 . free . 10956546 .
  14. 21 September 2018 . Kozenis (tafenoquine) approved by the Australian Therapeutic Goods Administration for the radical cure of P. vivax malaria . Medicines for Malaria Venture. 15 October 2018.
  15. Web site: Kodatef . NPS MedicineWise . 17 May 2022 . en.
  16. Web site: Drug Approval Package: Arakoda . U.S. Food and Drug Administration (FDA) . 13 February 2019 . https://web.archive.org/web/20191123043148/https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210607Orig1s000TOC.cfm . 23 November 2019 . live . 22 November 2019.
  17. Web site: Drug Approval Package: Krintafel (tafenoquine) . U.S. Food and Drug Administration (FDA) . 24 August 2018 . https://web.archive.org/web/20191123041317/https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210795Orig1s000TOC.cfm . 23 November 2019 . live . 22 November 2019.
  18. Web site: Drug Trials Snapshots: Krintafel . U.S. Food and Drug Administration (FDA) . 6 August 2018 . https://web.archive.org/web/20191123041626/https://www.fda.gov/drugs/drug-approvals-and-databases/drug-trials-snapshots-krintafel . 23 November 2019 . live . 22 November 2019.
  19. 20 July 2018. US FDA approves Krintafel (tafenoquine) for the radical cure of P. vivax malaria. Medicines for Malaria Venture. 15 October 2018.

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