5801. Mefloquine

Nomenclature

CAS number: 53230-10-7
S)-rel-α-(2R)-2-Piperidinyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol; dl-erythro-α-2-piperidyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol; Ro-21-5998.
C17H16F6N2O; mol wt 378.31.
C 53.97%, H 4.26%, F 30.13%, N 7.40%, O 4.23%.

Description and references

Quinoline methanol antimalarial agent. Prepn (stereo unspec): C. J. Ohnmacht et al., J. Med. Chem. 14, 926 (1971). Prepn, activity, and abs config of isomers: F. I. Carroll, J. T. Blackwell, J. Med. Chem. 17, 210 (1974). Prepn of erythro-form: G. Grethe, T. Mitt, DE 2806909; H. B"omches, B. Hardegger, US 4507482 (1978, 1985 both to Hoffmann-La Roche). X-ray crystal structure: A. Skórska et al., Bioorg. Med. Chem. Lett. 16, 850 (2006). Mechanism of action studies: M. W. Davidson et al., J. Med. Chem. 20, 1117 (1977); R. E. Brown et al., Life Sci. 25, 1857 (1979). Photochemistry: G. A. Epling, U. C. Yoon, Chem. Lett. 1982 (2), 211. Pharmacokinetics: D. E. Schwartz et al., Chemotherapy (Basel) 28, 70 (1982). HPLC determn in blood and plasma: I. M. Kapetanovic et al., J. Chromatogr. 277, 209 (1983). Comprehensive description: P. Lim, Anal. Profiles Drug Subs. 14, 157-180 (1985). Review of development: Bull. WHO 61, 169-178 (1983); of clinical trials in malaria prophylaxis: A. Croft, P. Garner, Br. Med. J. 315, 1412-1416 (1997).

Chemical structure

Properties

mp 174-176°. Crystal density: 1.432 g/cm3.

Derivative

Hydrochloride.

Nomenclature

CAS number: 51773-92-3
WR-142490; Lariam (Roche).
C17H16F6N2O.HCl.

Properties

Odorless, white powder, mp 259-260° (dec). Sol in ethanol, ethyl acetate; slightly sol in water. uv max (methanol): 222, 283, 304, 318 nm (ε 46700, 6600, 4000, 3100).

Therapeutic Category

Antimalarial.

Keywords

Antimalarial