Tafenoquine

Tafenoquine
Names
Trade namesKrintafel, Arakoda, others
Other namesEtaquine,[1] WR 238605,[1] SB-252263
IUPAC name
  • N-[2,6-Dimethoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]quinolin-8-yl]pentane-1,4-diamine
Clinical data
Drug classAntimalarial
Pregnancy
category
  • AU: C[2]
  • US: N (Not classified yet)[2]
    Routes of
    use    		By mouth
    Defined daily doseNot established[3]
    External links
    AHFS/Drugs.comKrintafel Monograph
    Arakoda Monograph
    MedlinePlusa618050
    Legal
    License data
    Legal status
    Chemical and physical data
    FormulaC24H28F3N3O3
    Molar mass463.493 g/mol
    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 checkY
    • Key:LBHLFPGPEGDCJG-UHFFFAOYSA-N checkY

    Tafenoquine, sold under the brand name Krintafel among others, is a medication used to prevent and to treat malaria.[4] With respect acute malaria it is used together with other medications to prevent relapse by Plasmodium vivax.[4] It may be used to prevent all types of malaria.[4] It is taken by mouth.[5]

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

    Tafenoquine was approved for medical use in Australia and in the United States in 2018.[4][6] In the United States, as of 2019, a course of treatment costs about US$43.[7] Tafenoquine is related to primaquine.[8]

    Medical use

    Prevention

    Tafenoquine may be used to prevent all types of malaria.[4] For this use 200 mg 3 days before travel then 200 mg per week until one week after travel is recommended.[8]

    Treatment

    Tafenoquine is used for the 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. 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.[9] It is used with another medication, such as chloroquine, that kills the malaria in the blood.[10]

    Dosage

    For prevention of malaria, it is taken as 200 mg per day for three days before being potentially exposed, than it is taken as 200 mg once per week including for 1 week after leaving the area with malaria.[11]

    It is also used at a dose of 300 mg together with other antimalarials to treat P. vivax.[12][8]

    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.[4][6] Tafenoquine was given an orphan drug designation and was granted breakthrough therapy status in 2013 in the United States.[13][14]

    Society and culture

    One version is made by GlaxoSmithKline.[5] While another is made by 60 Degrees Pharmaceutical.[15]

    Names

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

    Trade names

    References

    1. 1 2 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. 1 2 Use During Pregnancy and Breastfeeding
    3. ↑ "WHOCC - ATC/DDD Index". www.whocc.no. Archived from the original on 9 July 2021. Retrieved 10 September 2020.
    4. 1 2 3 4 5 6 7 8 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. PMID 31751320. Archived (PDF) from the original on 24 March 2021. Retrieved 23 November 2019.
    5. 1 2 3 4 5 6 7 "Tafenoquine Succinate (Krintafel) Monograph for Professionals". Drugs.com. Archived from the original on 7 August 2020. Retrieved 22 November 2019.
    6. 1 2 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.
    7. ↑ "Krintafel Prices, Coupons & Patient Assistance Programs". Drugs.com. Archived from the original on 9 July 2021. Retrieved 22 November 2019.
    8. 1 2 3 "Tafenoquine Approved for Malaria Prophylaxis and Treatment". Centers for Disease Control and Prevention (CDC). 25 April 2019. Archived from the original on 9 July 2021. Retrieved 22 November 2019.
    9. ↑ 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.
    10. ↑ "Conclusions and Recommendations from the Fifteenth Meeting of the WHO Advisory Committee on Safety of Medicinal Products (ACSoMP)" (PDF). WHO. Archived (PDF) from the original on 7 August 2020. Retrieved 22 November 2019.
    11. ↑ "Tafenoquine (Arakoda) Monograph for Professionals". Drugs.com. Archived from the original on 28 May 2023. Retrieved 28 June 2023.
    12. ↑ "Tafenoquine (Krintafel) Monograph for Professionals". Drugs.com. Archived from the original on 22 September 2022. Retrieved 28 June 2023.
    13. ↑ "Krintafel (tafenoquine succinate tablets) FDA Advisory Committee Briefing Document" (PDF). 12 July 2018. Archived from the original on 23 November 2019. Retrieved 22 November 2019.
    14. ↑ "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.
    15. ↑ 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.
    16. ↑ "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. Archived from the original on 15 October 2018. Retrieved 15 October 2018.
    17. ↑ "Kodatef". NPS MedicineWise. Archived from the original on 29 August 2021. Retrieved 31 March 2020.
    18. ↑ "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.
    19. ↑ "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.
    20. ↑ "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.
    21. ↑ "US FDA approves Krintafel (tafenoquine) for the radical cure of P. vivax malaria" (Press release). Medicines for Malaria Venture. 20 July 2018. Archived from the original on 15 October 2018. Retrieved 15 October 2018.
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