Tafenoquine

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 319630

CAS#: 106635-80-7

Description: Tafenoquine, also known as WR-238605, is an oral active antimalaria drug that is being investigated as a potential treatment for malaria, as well as for malaria prevention. Tafenoquine Shows Activity against Trypanosoma brucei. Tafenoquine targets leishmania respiratory complex III and induces apoptosis. Tafenoquine has a long half-life of approximately 14 days and is generally safe and well tolerated, Malaria remains an important cause of global morbidity and mortality. As antimalarial drug resistance escalates, new safe and effective medications are necessary to prevent and treat malarial infection.


Price and Availability

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Price

1g
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Size
Price

2g
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Size
Price

5g
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Tafenoquine is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 319630
Name: Tafenoquine
CAS#: 106635-80-7
Chemical Formula: C24H28F3N3O3
Exact Mass: 463.2083
Molecular Weight: 463.5012
Elemental Analysis: C, 62.19; H, 6.09; F, 12.30; N, 9.07; O, 10.36


Related CAS #: 106635-80-7 (free base)   106635-86-3 (succinate)  

Synonym: WR-238605, WR 238605, WR238605, Tafenoquine

IUPAC/Chemical Name: N4-(2,6-dimethoxy-4-methyl-5-(3-(trifluoromethyl)phenoxy)quinolin-8-yl)pentane-1,4-diamine

InChi Key: LBHLFPGPEGDCJG-UHFFFAOYSA-N

InChi Code: 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

SMILES Code: CC1=CC(=NC2=C1C(=C(C=C2NC(C)CCCN)OC)OC3=CC=CC(=C3)C(F)(F)F)OC


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

21: Carvalho L, Luque-Ortega JR, Manzano JI, Castanys S, Rivas L, Gamarro F. Tafenoquine, an antiplasmodial 8-aminoquinoline, targets leishmania respiratory complex III and induces apoptosis. Antimicrob Agents Chemother. 2010 Dec;54(12):5344-51. doi: 10.1128/AAC.00790-10. Epub 2010 Sep 13. PubMed PMID: 20837758; PubMed Central PMCID: PMC2981264.

22: Yardley V, Gamarro F, Croft SL. Antileishmanial and antitrypanosomal activities of the 8-aminoquinoline tafenoquine. Antimicrob Agents Chemother. 2010 Dec;54(12):5356-8. doi: 10.1128/AAC.00985-10. Epub 2010 Sep 13. Erratum in: Antimicrob Agents Chemother. 2011 Jan;55(1):458. PubMed PMID: 20837750; PubMed Central PMCID: PMC2981226.

23: Nasveld PE, Edstein MD, Reid M, Brennan L, Harris IE, Kitchener SJ, Leggat PA, Pickford P, Kerr C, Ohrt C, Prescott W; Tafenoquine Study Team. Randomized, double-blind study of the safety, tolerability, and efficacy of tafenoquine versus mefloquine for malaria prophylaxis in nonimmune subjects. Antimicrob Agents Chemother. 2010 Feb;54(2):792-8. doi: 10.1128/AAC.00354-09. Epub 2009 Dec 7. PubMed PMID: 19995933; PubMed Central PMCID: PMC2812156.

24: Leary KJ, Riel MA, Roy MJ, Cantilena LR, Bi D, Brater DC, van de Pol C, Pruett K, Kerr C, Veazey JM Jr, Beboso R, Ohrt C. A randomized, double-blind, safety and tolerability study to assess the ophthalmic and renal effects of tafenoquine 200 mg weekly versus placebo for 6 months in healthy volunteers. Am J Trop Med Hyg. 2009 Aug;81(2):356-62. PubMed PMID: 19635898.

25: 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. Trans R Soc Trop Med Hyg. 2008 Nov;102(11):1095-101. doi: 10.1016/j.trstmh.2008.04.024. Epub 2008 Jun 9. PubMed PMID: 18541280.

26: Charles BG, Miller AK, Nasveld PE, Reid MG, Harris IE, Edstein MD. Population pharmacokinetics of tafenoquine during malaria prophylaxis in healthy subjects. Antimicrob Agents Chemother. 2007 Aug;51(8):2709-15. Epub 2007 May 21. PubMed PMID: 17517850; PubMed Central PMCID: PMC1932489.

27: Crockett M, Kain KC. Tafenoquine: a promising new antimalarial agent. Expert Opin Investig Drugs. 2007 May;16(5):705-15. Review. PubMed PMID: 17461742.

28: Kitchener S, Nasveld P, Edstein MD. Tafenoquine for the treatment of recurrent Plasmodium vivax malaria. Am J Trop Med Hyg. 2007 Mar;76(3):494-6. PubMed PMID: 17360873.

29: Pradines B, Mamfoumbi MM, Tall A, Sokhna C, Koeck JL, Fusai T, Mosnier J, Czarnecki E, Spiegel A, Trape JF, Kombila M, Rogier C. In vitro activity of tafenoquine against the asexual blood stages of Plasmodium falciparum isolates from Gabon, Senegal, and Djibouti. Antimicrob Agents Chemother. 2006 Sep;50(9):3225-6. PubMed PMID: 16940138; PubMed Central PMCID: PMC1563556.

30: Edstein MD, Nasveld PE, Kocisko DA, Kitchener SJ, Gatton ML, Rieckmann KH. Gender differences in gastrointestinal disturbances and plasma concentrations of tafenoquine in healthy volunteers after tafenoquine administration for post-exposure vivax malaria prophylaxis. Trans R Soc Trop Med Hyg. 2007 Mar;101(3):226-30. Epub 2006 Jun 30. PubMed PMID: 16814823.

31: Nasveld P, Kitchener S. Treatment of acute vivax malaria with tafenoquine. Trans R Soc Trop Med Hyg. 2005 Jan;99(1):2-5. PubMed PMID: 15550254.

32: Vollnberg A, Prajakwong S, Sirichaisinthop J, Wiedermann G, Wernsdorfer G, Wernsdorfer WH. In-vitro interaction of tafenoquine and chloroquine in Plasmodium falciparum from northwestern Thailand. Wien Klin Wochenschr. 2003;115 Suppl 3:28-32. PubMed PMID: 15508777.

33: Walsh DS, Wilairatana P, Tang DB, Heppner DG Jr, Brewer TG, Krudsood S, Silachamroon U, Phumratanaprapin W, Siriyanonda D, Looareesuwan S. Randomized trial of 3-dose regimens of tafenoquine (WR238605) versus low-dose primaquine for preventing Plasmodium vivax malaria relapse. Clin Infect Dis. 2004 Oct 15;39(8):1095-103. Epub 2004 Sep 24. PubMed PMID: 15486831.

34: Walsh DS, Eamsila C, Sasiprapha T, Sangkharomya S, Khaewsathien P, Supakalin P, Tang DB, Jarasrumgsichol P, Cherdchu C, Edstein MD, Rieckmann KH, Brewer TG. Efficacy of monthly tafenoquine for prophylaxis of Plasmodium vivax and multidrug-resistant P. falciparum malaria. J Infect Dis. 2004 Oct 15;190(8):1456-63. Epub 2004 Sep 20. PubMed PMID: 15378438.

35: Ponsa N, Sattabongkot J, Kittayapong P, Eikarat N, Coleman RE. Transmission-blocking activity of tafenoquine (WR-238605) and artelinic acid against naturally circulating strains of Plasmodium vivax in Thailand. Am J Trop Med Hyg. 2003 Nov;69(5):542-7. PubMed PMID: 14695093.

36: Edstein MD, Kocisko DA, Walsh DS, Eamsila C, Charles BG, Rieckmann KH. Plasma concentrations of tafenoquine, a new long-acting antimalarial agent, in thai soldiers receiving monthly prophylaxis. Clin Infect Dis. 2003 Dec 15;37(12):1654-8. Epub 2003 Nov 20. PubMed PMID: 14689348.

37: Molecule of the month. Tafenoquine succinate. Drug News Perspect. 2003 May;16(4):238. PubMed PMID: 12942153.

38: Puri SK, Dutta GP. Blood schizontocidal activity of WR 238605 (Tafenoquine) against Plasmodium cynomolgi and Plasmodium fragile infections in rhesus monkeys. Acta Trop. 2003 Apr;86(1):35-40. PubMed PMID: 12711101.

39: Nasveld P, Kitchener S, Edstein M, Rieckmann K. Comparison of tafenoquine (WR238605) and primaquine in the post-exposure (terminal) prophylaxis of vivax malaria in Australian Defence Force personnel. Trans R Soc Trop Med Hyg. 2002 Nov-Dec;96(6):683-4. PubMed PMID: 12625150.

40: Hale BR, Owusu-Agyei S, Fryauff DJ, Koram KA, Adjuik M, Oduro AR, Prescott WR, Baird JK, Nkrumah F, Ritchie TL, Franke ED, Binka FN, Horton J, Hoffman SL. A randomized, double-blind, placebo-controlled, dose-ranging trial of tafenoquine for weekly prophylaxis against Plasmodium falciparum. Clin Infect Dis. 2003 Mar 1;36(5):541-9. Epub 2003 Feb 14. PubMed PMID: 12594633.