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Merck
CN

SML0396

Tafenoquine succinate

≥95% (HPLC), primaquine analog, powder

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
UNSPSC Code:
12352200
PubChem Substance ID:
329825392
NACRES:
NA.77
MDL number:
MFCD00892249

Key Documents

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Product Name

Tafenoquine succinate, ≥95% (HPLC)

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

assay

≥95% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: 5 mg/mL (clear solution)

storage temp.

2-8°C

Quality Level

100

Related Categories

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.
Tafenoquine is an antimalarial.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000449287
0000449287
0000396678
0000388943
0000382838

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Travelers' Malaria, 172-172 (2008)
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
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)
James A Chambers
Military medicine, 168(12), 1001-1006 (2004-01-15)
U.S. military aviators are currently restricted to the use of chloroquine or doxycycline for malaria prophylaxis. Ground forces are allowed the additional option of taking mefloquine. These medications are begun before deployment, must be taken for 4 weeks after leaving
Christopher J Parkinson et al.
The Journal of antimicrobial chemotherapy, 74(10), 2965-2973 (2019-07-22)
Drug resistance exists to all current and investigational antimalarial drug classes. Consequently, we have set out to develop chemically and mechanistically discrete antimalarials. Here we report on the development of thiosemicarbazone (TSC) antimalarials, with TSC3 as the most advanced lead.
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