WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H319630
CAS#: 106635-80-7 (free base)
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.
Hodoodo Cat#: H319630
Name: Tafenoquine free base
CAS#: 106635-80-7 (free base)
Chemical Formula: C24H28F3N3O3
Exact Mass: 463.21
Molecular Weight: 463.501
Elemental Analysis: C, 62.19; H, 6.09; F, 12.30; N, 9.07; O, 10.36
Related CAS #: 106635-80-7 (free base) 106635-81-8 (succinate) 1133378-83-2 (d3)
Synonym: WR-238605, WR 238605, WR238605, SB-252263-AAB; SB252263-AAB; SB 252263-AAB; Tafenoquine; Krintafel
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
Appearance: Light yellow 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).
HS Tariff Code: 2934.99.9001
More Info:
Biological target: | |
In vitro activity: | |
In vivo activity: |
The following data is based on the product molecular weight 463.50 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: | |
In vitro protocol: | |
In vivo protocol: |
1: Rodrigo C, Rajapakse S, Fernando SD. Compliance with Primary Malaria Chemoprophylaxis: Is Weekly Prophylaxis Better Than Daily Prophylaxis? Patient Prefer Adherence. 2020 Nov 9;14:2215-2223. doi: 10.2147/PPA.S255561. PMID: 33204072; PMCID: PMC7665499.
2: Dean L, Kane M. Tafenoquine Therapy and G6PD Genotype. 2020 Oct 13. In: Pratt VM, Scott SA, Pirmohamed M, Esquivel B, Kane MS, Kattman BL, Malheiro AJ, editors. Medical Genetics Summaries [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2012–. PMID: 33048487.
3: IV artesunate for severe malaria. Med Lett Drugs Ther. 2020 Aug 10;62(1604):121-124. PMID: 32960866.
4: Chu CS, Bancone G, Kelley M, Advani N, Domingo GJ, Cutiongo-de la Paz EM, van der Merwe N, Cohen J, Gerth-Guyette E. Optimizing G6PD testing for Plasmodium vivax case management and beyond: why sex, counseling, and community engagement matter. Wellcome Open Res. 2020 Aug 25;5:21. doi: 10.12688/wellcomeopenres.15700.2. PMID: 32766454; PMCID: PMC7388194.
5: Hanboonkunupakarn B, White NJ. Advances and roadblocks in the treatment of malaria. Br J Clin Pharmacol. 2020 Jul 12. doi: 10.1111/bcp.14474. Epub ahead of print. PMID: 32656850.
6: Duparc S, Chalon S, Miller S, Richardson N, Toovey S. Neurological and psychiatric safety of tafenoquine in Plasmodium vivax relapse prevention: a review. Malar J. 2020 Mar 14;19(1):111. doi: 10.1186/s12936-020-03184-x. PMID: 32169086; PMCID: PMC7071640.
7: National Academies of Sciences, Engineering, and Medicine; Health and Medicine Division; Committee to Review Long-Term Health Effects of Antimalarial Drugs; Board on Population Health and Public Health Practice. Assessment of Long-Term Health Effects of Antimalarial Drugs When Used for Prophylaxis. Styka AN, Savitz DA, editors. Washington (DC): National Academies Press (US); 2020 Feb 25. PMID: 32369311.
8: Haston JC, Hwang J, Tan KR. Guidance for Using Tafenoquine for Prevention and Antirelapse Therapy for Malaria - United States, 2019. MMWR Morb Mortal Wkly Rep. 2019 Nov 22;68(46):1062-1068. doi: 10.15585/mmwr.mm6846a4. PMID: 31751320; PMCID: PMC6871897.
9: Meltzer E, Schwartz E. Utility of 8-Aminoquinolines in Malaria Prophylaxis in Travelers. Curr Infect Dis Rep. 2019 Nov 7;21(11):43. doi: 10.1007/s11908-019-0698-1. PMID: 31701249.
10: Advice for travelers. Med Lett Drugs Ther. 2019 Oct 7;61(1582):153-160. PMID: 31599872.
11: Expanded table: drugs for prophylaxis of malaria. Med Lett Drugs Ther. 2019 Jul 1;61(1575):e104-e105. PMID: 31381543.
12: Baird JK. 8-Aminoquinoline Therapy for Latent Malaria. Clin Microbiol Rev. 2019 Jul 31;32(4):e00011-19. doi: 10.1128/CMR.00011-19. PMID: 31366609; PMCID: PMC6750137.
13: 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.
14: Chen V, Daily JP. Tafenoquine: the new kid on the block. Curr Opin Infect Dis. 2019 Oct;32(5):407-412. doi: 10.1097/QCO.0000000000000574. PMID: 31305490.
15: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006–. Tafenoquine. 2019 May 1. PMID: 30222296.
16: Makhani L, Khatib A, Corbeil A, Kariyawasam R, Raheel H, Clarke S, Challa P, Hagopian E, Chakrabarti S, Schwartz KL, Boggild AK. 2018 in review: five hot topics in tropical medicine. Trop Dis Travel Med Vaccines. 2019 Apr 15;5:5. doi: 10.1186/s40794-019-0082-z. PMID: 31016025; PMCID: PMC6466725.
17: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Tafenoquine. 2019 Apr 10. PMID: 31643747.
18: Chu CS, Freedman DO. Tafenoquine and G6PD: a primer for clinicians. J Travel Med. 2019 Jun 1;26(4):taz023. doi: 10.1093/jtm/taz023. PMID: 30941413; PMCID: PMC6542331.
19: Tse EG, Korsik M, Todd MH. The past, present and future of anti-malarial medicines. Malar J. 2019 Mar 22;18(1):93. doi: 10.1186/s12936-019-2724-z. PMID: 30902052; PMCID: PMC6431062.
20: 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. Infect Drug Resist. 2019 Mar 6;12:553-570. doi: 10.2147/IDR.S151031. PMID: 30881061; PMCID: PMC6411314.
Srinivasan S, Roy D, Chavas TEJ, Vlaskin V, Ho DK, Pottenger A, LeGuyader CLM, Maktabi M, Strauch P, Jackson C, Flaherty SM, Lin H, Zhang J, Pybus B, Li Q, Huber HE, Burke PA, Wesche D, Rochford R, Stayton PS. Liver-targeted polymeric prodrugs of 8-aminoquinolines for malaria radical cure. J Control Release. 2021 Mar 10;331:213-227. doi: 10.1016/j.jconrel.2020.12.046. Epub 2020 Dec 27. PMID: 33378692.