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SML0396

Sigma-Aldrich

Tafenoquine succinate

≥95% (HPLC)

Synonym(s):

N-[2,6-Dimethoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]quinolin-8-yl]pentane-1,4-diamine, SB-252263, WR 238605

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About This Item

Empirical Formula (Hill Notation):
C24H28F3N3O3 · C4H6O4
CAS Number:
106635-81-8
Molecular Weight:
581.58
MDL number:
MFCD00892249
UNSPSC Code:
12352200
PubChem Substance ID:
329825392
NACRES:
NA.77

Quality Level

100

Assay

≥95% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: 5 mg/mL (clear solution)

storage temp.

2-8°C

SMILES string

OC(=O)CCC(O)=O.COc1cc(C)c2c(Oc3cccc(c3)C(F)(F)F)c(OC)cc(NC(C)CCCN)c2n1

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)

InChI key

CQBKFGJRAOXYIP-UHFFFAOYSA-N

Biochem/physiol Actions

Tafenoquine has been generally generated for oral administration and drug absorption increases when taken along with food. It is known to possess a longer half life.
Tafenoquine is an antimalarial primaquine analog being investigated to treat and prevent Plasmodium vivax infections. It can eliminate both blood and liver stages of Plasmodium vivax. Tafenoquine has also been tested as a therapy for leishmaniasis.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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In vitro activity of tafenoquine against the asexual blood stages of Plasmodium falciparum isolates from Gabon, Senegal, and Djibouti.
Bruno Pradines et al.
Antimicrobial agents and chemotherapy, 50(9), 3225-3226 (2006-08-31)
Anke Vollnberg et al.
Wiener klinische Wochenschrift, 115 Suppl 3, 28-32 (2004-10-29)
The blood schizontocidal, pharmacodynamic interaction between tafenoquine (WR 238605--a 5-phenoxyprimaquine derivative--and chloroquine was investigated, using an in-vitro test for the inhibition of schizont maturation, in 15 fresh isolates of Plasmodium falciparum that originated from northwestern Thailand and neighbouring Myanmar. In
Travelers' Malaria, 172-172 (2008)
Krisztina Németh et al.
Journal of pharmaceutical and biomedical analysis, 54(3), 475-481 (2010-10-15)
Capillary electrophoresis (CE) methods for chiral resolution of five antimalarial drugs (primaquine, tafenoquine, mefloquine, chloroquine and quinacrine) were developed by using a wide selection of neutral and anionic cyclodextrin (CD) derivatives. The use of sulfobutyl-β-CD and carboxymethyl-β-CD (CMBCD) resulted in
Bruce G Charles et al.
Antimicrobial agents and chemotherapy, 51(8), 2709-2715 (2007-05-23)
The population pharmacokinetics of tafenoquine were studied in Australian soldiers taking tafenoquine for malarial prophylaxis. The subjects (476 males and 14 females) received a loading dose of 200 mg tafenoquine base daily for 3 days, followed by a weekly dose
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