Tafenoquine succinate
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MedKoo CAT#: 330165

CAS#: 106635-81-8 (succinate)

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.


Chemical Structure

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Tafenoquine succinate
CAS# 106635-81-8 (succinate)

Theoretical Analysis

MedKoo Cat#: 330165
Name: Tafenoquine succinate
CAS#: 106635-81-8 (succinate)
Chemical Formula: C28H34F3N3O7
Exact Mass: 0.00
Molecular Weight: 581.590
Elemental Analysis: C, 57.83; H, 5.89; F, 9.80; N, 7.23; O, 19.26

Price and Availability

Size Price Availability Quantity
10mg USD 150 Ready to ship
25mg USD 250 Ready to ship
50mg USD 450 Ready to ship
100mg USD 750 Ready to ship
200mg USD 1350 Ready to ship
500mg USD 2850 Ready to ship
1g USD 4250 Ready to ship
2g USD 6950 Ready to ship
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Related CAS #: 106635-80-7 (free base)   106635-81-8 (succinate)   1133378-83-2 (d3)    

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

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

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

More Info:

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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 125.0 214.93

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.

Recalculate based on batch purity %
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.

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