Tafenoquine (Succinate)

Names

[ Name ]:
Tafenoquine (Succinate)

[Synonym ]:
Tafenoquine succinate
UNII-DL5J0B8VSS
Tafenoquine Succinate
tafenoquine maleate
Etaquine
Tafenoquine (Succinate)

Biological Activity

[Description]:

Tafenoquine Succinate (WR 238605 Succinate) is an 8-aminoquinoline. Tafenoquine is an anti-malarial prophylactic agent[1].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Parasite

Research Areas >> Infection

[Target]

Anti-malarial[1]

[In Vivo]

Tafenoquine exhibits no anti-malarial activity in CYP 2D knock-out mice when dosed at their ED100 values (3 mg/kg) established in WT mice. Tafenoquine anti-malarial activity is partially restored in humanized/CYP 2D6 knock-in mice when tested at two times its ED100 (6 mg/kg)[1].

[References]

[1]. Marcsisin SR, et al. Tafenoquine and NPC-1161B require CYP 2D metabolism for anti-malarial activity: implications for the 8-aminoquinoline class of anti-malarial compounds. Malar J. 2014 Jan 3;13:2.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.237g/cm3

[ Boiling Point ]:
565.6ºC at 760mmHg

[ Molecular Formula ]:
C₂₈H₃₄F₃N₃O₇

[ Molecular Weight ]:
581.58100

[ Flash Point ]:
295.9ºC

[ Exact Mass ]:
581.23500

[ PSA ]:
153.23000

[ LogP ]:
6.61990

[ Storage condition ]:
2-8℃

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: SA0242400

CAS REGISTRY NUMBER :: 106635-81-8

LAST UPDATED :: 199107

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C24-H28-F3-N3-O3.C4-H6-O4

MOLECULAR WEIGHT :: 581.65

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 416 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 32,1728,1989

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 71 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 32,1728,1989

Safety Information

[ RIDADR ]:
NONH for all modes of transport

Articles

Uptake of the antileishmania drug tafenoquine follows a sterol-dependent diffusion process in Leishmania.

J. Antimicrob. Chemother. 66(11) , 2562-5, (2011)

The present study was designed to elucidate the mechanism of tafenoquine uptake in Leishmania and its sterol dependence.Because tafenoquine is a fluorescent compound, spectrofluorimetric analysis allo...

Transmission-blocking activity of tafenoquine (WR-238605) and artelinic acid against naturally circulating strains of Plasmodium vivax in Thailand.

Am. J. Trop. Med. Hyg. 69(5) , 542-7, (2003)

The sporontocidal activity of tafenoquine (WR-238605) and artelinic acid was determined against naturally circulating isolates of Plasmodium vivax in western Thailand. Primaquine was used as a negativ...

Military aviators, special operations forces, and causal malaria prophylaxis.

Mil. Med. 168(12) , 1001-6, (2003)

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 medication...