Mefloquine
Title: Mefloquine
CAS Registry Number: 53230-10-7
CAS Name: (aS)-rel-a-(2R)-2-Piperidinyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol
Additional Names: DL-erythro-a-2-piperidyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol
Manufacturers' Codes: Ro-21-5998
Molecular Formula: C17H16F6N2O
Molecular Weight: 378.31
Percent Composition: C 53.97%, H 4.26%, F 30.13%, N 7.40%, O 4.23%
Literature 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. Bömches, 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).
Properties: mp 174-176°. Crystal density: 1.432 g/cm3.
Melting point: mp 174-176°
 
Derivative Type: Hydrochloride
CAS Registry Number: 51773-92-3
Manufacturers' Codes: WR-142490
Trademarks: Lariam (Roche)
Molecular Formula: C17H16F6N2O.HCl
Molecular Weight: 414.77
Percent Composition: C 49.23%, H 4.13%, F 27.48%, N 6.75%, O 3.86%, Cl 8.55%
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 (e 46700, 6600, 4000, 3100).
Melting point: mp 259-260° (dec)
Absorption maximum: uv max (methanol): 222, 283, 304, 318 nm (e 46700, 6600, 4000, 3100).
 
Therap-Cat: Antimalarial.
Keywords: Antimalarial.

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