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Merck

SML0396

Sigma-Aldrich

Tafenoquine succinate

≥95% (HPLC)

Sinónimos:

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

Fórmula empírica (notación de Hill):
C24H28F3N3O3 · C4H6O4
Número de CAS:
Peso molecular:
581.58
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificados de análisis (COA)

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Travelers' Malaria, 172-172 (2008)
Vanessa Yardley et al.
Antimicrobial agents and chemotherapy, 54(12), 5356-5358 (2010-09-15)
The 8-aminoquinoline tafenoquine showed significant in vitro activity against Leishmania species, including L. donovani amastigotes in macrophages, with 50% inhibitory concentrations (IC(50)s) between 0.1 and 4.0 μM for both pentavalent antimony (SbV)-sensitive and SbV-resistant strains and by oral administration in
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.
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
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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