X-ray crystal structure of the antimalarial agent (-)-halofantrine hydrochloride supports stereospecificity for cardiotoxicity

Antimicrobial Agents and Chemotherapy

Volumn 41, Issue 4, 1997, Pages 791-794

  Karle, Jean M ^a  

^a WALTER REED ARMY INSTITUTE OF RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HALOFANTRINE;

ANTIMALARIAL ACTIVITY; ARTICLE; CARDIOTOXICITY; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; DRUG CONFORMATION; HYDROGEN BOND; MALARIA; PRIORITY JOURNAL; RACEMIC MIXTURE; STEREOSPECIFICITY; STRUCTURE ACTIVITY RELATION; X RAY DIFFRACTION;

EID: 0030978656     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/aac.41.4.791     Document Type: Article

References (23)

1. Basco, L. K., C. Gillotin, F. Gimenez, R. Farinotti, and J. Le Bras. 1992. In vitro activity of the enantiomers of mefloquine, halofantrine, and enpiroline against Plasmodium falciparum. Br. J. Clin. Pharmacol. 33:517-520.
2. Boudreau, E. F., L. W. Pang, K. F. Dixon, H. K. Webster, K. Pavanand, L. Toshingha, P. Somutsakorn, and C. J. Canfield. 1988. Malaria: treatment efficacy of halofantrine (WR 171,669) in initial field trials in Thailand. Bull. W. H. O. 66:227-235.
3. Bryson, H. M., and K. L. Goa. 1992. Halofantrine, A review of its antimalarial activity, pharmacokinetic properties and therapeutic potential. Drugs 43:236-258.
4. Carroll, F. I., B. Berrang, and C. P. Linn. 1978. Resolution of antimalarial agents via complex formation with α-(2,4,5,7-tetranitro-9-fluorenylideneaminooxy)propionic acid. J. Med. Chem, 21:326-330.
5. Gimenez, F., C. Gillotin, L. K. Basco, O. Bouchaud, A.-F. Aubry, I. W. Wainer, J. Le Bras, and R. Farinotti. 1994. Plasma concentrations of the enantiomers of halofantrine and its main metabolite in malaria patients. Eur. J. Clin. Pharmacol. 46:561-562.
6. Hamilton, W. C. 1965. Significance tests on the crystallographic R factor. Acta Crystallogr. 18:502-510.
7. Johnson, C. K. 1976. ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge, Tenn.
8. Karbwang, J., and K. N. Bangchang. 1994. Clinical pharmacokinetics of halofantrine. Clin. Pharmacokinet. 27:104-119.
9. 2O: implications for structure analysis. Proc. Natl. Acad. Sci. USA 78:5938-5941.
10. Karle, J., and I. L. Karle. 1966. The symbolic addition procedure for phase determination for centrosymmetric and noncentrosymmetric crystals. Acta Crystallogr. 21:849-859.
11. Karle, J. M., and I. L. Karle. 1989. Structure of the antimalarial halofantrine hydrochloride. Acta Crystallogr. Sect. C 45:1248-1250.
12. Karle, J. M., R. Olmeda, L. Gerena, and W. K. Milhous. 1993. Plasmodium falciparum: role of absolute stereochemistry in the antimalarial activity of synthetic amino alcohol antimalarial agents. Exp. Parasitol. 76:345-351.
13. Pniewska, B., and A. Suszko-Purzycka. 1989. Structure of quinine monohydrate toluene solvate. Acta Crystallogr. Sect. C 45:638-642.
14. Roden, D. M. 1996. Antiarrhythmic drugs, p. 869-871. In J. G. Hardman, L. E. Limbird, P. B. Molinoff, R. W. Ruddon, and A. G. Gilman (ed.), Goodman & Gilman's the pharmacological basis of therapeutics, 9th ed., McGraw-Hill, New York, N.Y.
15. Sheldrick, G. M. 1980. SHELXTL. An Integrated System for Solving, Refining and Displaying Crystal Structures from Diffraction Data, University of Göttingen, Göttingen, Germany.
16. Stout, G. H., and L. H. Jensen. 1989. X-ray structure determination. A practical guide, 2nd ed. John Wiley & Sons, Inc., New York, N.Y.
17. Terefe, H., and G. Blaschke. 1993. Direct determination of the enantiomers of halofantrine and its pharmacologically active metabolite N-desbutylhalofantrine by high-performance liquid chromatography. J. Chromatogr. 615: 347-351.
18. Terefe, H., and G. Blaschke. 1994. Direct determination of the enantiomers of the antimalarial drug halofantrine and its active metabolite N-desbutylhalofantrine in human plasma. J. Chromatogr. B 657:238-242.
19. Ter Kuile, F. O., G. Dolan, F. Nosten, M. D. Edstein, C. Luxemburger, L. Phaipun, T. Chongsuphajaisiddah, H. K. Webster, and N. J. White. 1993. Halofantrine versus mefloquine in treatment of multidrug-resistant falciparum malaria. Lancet 341:1044-1049.
20. Touze, J. E., J. Bernard, A. Keundjian, P. Imbert, A. Viguier, H. Chaudet, and J. C. Doury. 1996. Electrocardiographic changes and halofantrine plasma level during acute falciparum malaria. Am. J. Trop. Med. Hyg. 54:225-228.
21. Watt, G., L. Loesuttiviboon, K. Jongsakul, G. D. Shanks, C. K. Ohrt, C. Karnasuta, B. Schuster, and L. Fleckenstein. 1994. Efficacy and tolerance of extended-dose halofantrine for drug-resistant falciparum malaria in Thailand. Am. J. Trop. Med. Hyg. 50:187-192.
22. Wesche, D. L., and J. Black. 1990. A comparison of the antimalarial activity of the cinchona alkaloids against P. falciparum in vitro. J. Trop. Med. Hyg. 93:153-159.
23. Wesche, D. L., Y. Chen, W. Wang, B. G. Schuster, and R. L. Woosley. 1995. Mechanism of cardiotoxicity of halofantrine, abstr. 350. p. 202. In Program and abstracts of the 44th Annual Meeting of the American Society of Tropical Medicine and Hygiene.