9029. Tafenoquine

Nomenclature

CAS number: 106635-80-7
N4-[2,6-Dimethoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]-8-quinolinyl]-1,4-pentanediamine; 8-[(4-amino-1-methylbutyl)amino]-2,6-dimethoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]quinoline; WR-238605.
C24H28F3N3O3; mol wt 463.49.
C 62.19%, H 6.09%, F 12.30%, N 9.07%, O 10.36%.

Description and references

Analog of primaquine, q.v. Prepn: P. Blumbergs, M. P. LaMontagne, US 4617394 (1986 to U.S. Sec. Army); M. P. LaMontagne et al., J. Med. Chem. 32, 1728 (1989). HPLC determn in blood and plasma: D. A. Kocisko et al., Ther. Drug Monit. 22, 184 (2000). Metabolism: O. R. Idowu et al., Drug Metab. Dispos. 23, 1 (1995). Clinical pharmacokinetics: M. D. Edstein et al., Br. J. Pharmacol. 52, 663 (2001). Clinical evaluation in prevention of malaria relapse: D. S. Walsh et al., J. Infect. Dis. 180, 1282 (1999); in malaria prophylaxis: B. Lell et al., Lancet 355, 2041 (2000); B. R. Hale et al., Clin. Infect. Dis. 36, 541 (2003).

Chemical structure

Derivative

Succinate.

Nomenclature

CAS number: 106635-81-8
Etaquine (GSK).
C24H28F3N3O3.C4H6O4; mol wt 581.58.
C 57.83%, H 5.89%, F 9.80%, N 7.23%, O 19.26%.

Properties

Crystals from acetonitrile, mp 146-149°. LD50 in male, female rats (mg/kg): 102, 71 i.p.; 429, 416 orally (LaMontagne).

Therapeutic Category

Antimalarial.

Keywords

Antimalarial