Synonym
Tafenoquine succinate; WR-238605, WR 238605, WR238605, SB-252263-AAB; SB252263-AAB; SB 252263-AAB; Krintafel;
IUPAC/Chemical Name
N4-(2,6-dimethoxy-4-methyl-5-(3-(trifluoromethyl)phenoxy)quinolin-8-yl)pentane-1,4-diamine succinate
InChi Key
CQBKFGJRAOXYIP-UHFFFAOYSA-N
InChi Code
InChI=1S/C24H28F3N3O3.C4H6O4/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;5-3(6)1-2-4(7)8/h5,8-9,11-13,15,29H,6-7,10,28H2,1-4H3;1-2H2,(H,5,6)(H,7,8)
SMILES Code
CC(NC1=C2N=C(OC)C=C(C)C2=C(OC3=CC=CC(C(F)(F)F)=C3)C(OC)=C1)CCCN.O=C(O)CCC(O)=O
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
Shelf Life
>3 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).
HS Tariff Code
2934.99.9001
Biological target:
Tafenoquine is an anti-malarial agent.
In vitro activity:
Tafenoquine (TFQ) efficiently inhibited in vitro proliferation of different species of T. brucei at concentrations in the nanomolar range, with 50% effective concentrations (EC50s) ranging from 0.17 ± 0.02 μM for T. brucei rhodesiense and 0.22 ± 0.03 μM for T. brucei brucei S427 to 0.42 ± 0.02 μM for T. brucei brucei S16. Furthermore, TFQ produced a disintegration of cell membranes with loss of cytoplasmic contents confirming necrotic cell death.
Reference: Antimicrob Agents Chemother. 2015 Oct;59(10):6151-60. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4576119/
In vivo activity:
The efficacy of tafenoquine (TQ) for treatment of Babesia microti infection was evaluated in mice with severe combined immunodeficiency (SCID). SCID mice were infected with 1.1-1.5 × 108 B. microti-infected red blood cells by intraperitoneal injection. On day 3 or 4 postinfection, when parasitemia levels typically exceeded 10%, mice were treated with TQ vs vehicle alone, both administered by oral gavage. A single dose of TQ completely eliminated detectable parasites, with a >90% reduction in the level of parasitemia within just 4 days. Before elimination, a conspicuous phenotypic change in the parasite was observed. Although parasitologic cure was not achieved, there was no evidence for the development of drug resistance.
Reference: J Infect Dis. 2019 Jul 2;220(3):442-447. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6603973/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMSO |
125.0 |
214.93 |
|
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
581.59
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Ramharter M, Noedl H, Thimasarn K, Wiedermann G, Wernsdorfer G, Wernsdorfer WH. In vitro activity of tafenoquine alone and in combination with artemisinin against Plasmodium falciparum. Am J Trop Med Hyg. 2002 Jul;67(1):39-43. doi: 10.4269/ajtmh.2002.67.39. PMID: 12363062.
2. Carvalho L, Martínez-García M, Pérez-Victoria I, Manzano JI, Yardley V, Gamarro F, Pérez-Victoria JM. The Oral Antimalarial Drug Tafenoquine Shows Activity against Trypanosoma brucei. Antimicrob Agents Chemother. 2015 Oct;59(10):6151-60. doi: 10.1128/AAC.00879-15. Epub 2015 Jul 20. PMID: 26195527; PMCID: PMC4576119.
3. Mordue DG, Wormser GP. Could the Drug Tafenoquine Revolutionize Treatment of Babesia microti Infection? J Infect Dis. 2019 Jul 2;220(3):442-447. doi: 10.1093/infdis/jiz119. PMID: 31099380; PMCID: PMC6603973.
In vitro protocol:
1. Ramharter M, Noedl H, Thimasarn K, Wiedermann G, Wernsdorfer G, Wernsdorfer WH. In vitro activity of tafenoquine alone and in combination with artemisinin against Plasmodium falciparum. Am J Trop Med Hyg. 2002 Jul;67(1):39-43. doi: 10.4269/ajtmh.2002.67.39. PMID: 12363062.
2. Carvalho L, Martínez-García M, Pérez-Victoria I, Manzano JI, Yardley V, Gamarro F, Pérez-Victoria JM. The Oral Antimalarial Drug Tafenoquine Shows Activity against Trypanosoma brucei. Antimicrob Agents Chemother. 2015 Oct;59(10):6151-60. doi: 10.1128/AAC.00879-15. Epub 2015 Jul 20. PMID: 26195527; PMCID: PMC4576119.
In vivo protocol:
1. Mordue DG, Wormser GP. Could the Drug Tafenoquine Revolutionize Treatment of Babesia microti Infection? J Infect Dis. 2019 Jul 2;220(3):442-447. doi: 10.1093/infdis/jiz119. PMID: 31099380; PMCID: PMC6603973.
1: Mordue DG, Hale SJ, Dennis WE, Vuong CV, Li XM, Yang N, Wormser GP. Plasma Blood Levels of Tafenoquine following a Single Oral Dosage in BALBc Mice with Acute Babesia microti Infection That Resulted in Rapid Clearance of Microscopically Detectable Parasitemia. Pathogens. 2023 Aug 31;12(9):1113. doi: 10.3390/pathogens12091113. PMID: 37764921; PMCID: PMC10534932.
2: Yang X, Zhang B, Wang S, Lu Y, Chen K, Luo C, Sun A, Zhang H. OTTM: an automated classification tool for translational drug discovery from omics data. Brief Bioinform. 2023 Sep 20;24(5):bbad301. doi: 10.1093/bib/bbad301. PMID: 37594310; PMCID: PMC10516341.
3: Kavthe RD, Kincaid JRA, Lipshutz BH. An Efficient and Sustainable Synthesis of the Antimalarial Drug Tafenoquine. ACS Sustain Chem Eng. 2022 Dec 19;10(50):16896-16902. doi: 10.1021/acssuschemeng.2c05628. Epub 2022 Dec 7. PMID: 36569493; PMCID: PMC9768812.
4: Tafenoquine succinate for malaria prevention. Aust Prescr. 2019 Jun;42(3):110-111. doi: 10.18773/austprescr.2019.034. Epub 2019 Apr 24. PMID: 31363314; PMCID: PMC6594846.
5: Bayés M, Rabasseda X. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2008 Jan-Feb;30(1):67-99. PMID: 18389098.
6: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2005 Jun;27(5):331-72. PMID: 16082422.
7: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2003 Nov;25(9):747-71. PMID: 14685303.
8: Molecule of the month. Tafenoquine succinate. Drug News Perspect. 2003 May;16(4):238. PMID: 12942153.
