Halofantrine metabolism in microsomes in man: Major role of CYP 3A4 and CYP 3A5

Journal of Pharmacy and Pharmacology

Volumn 51, Issue 4, 1999, Pages 419-426

  Baune, B ^a   Flinois, J P ^b   Furlan, V ^b   Gimenez, F ^a   Taburet, A M ^b   Becquemont, L ^b   Farinotti, R ^a  

^a UNIVERSITÉ PARIS SACLAY   (France)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA NAPHTHOFLAVONE; ANTIMALARIAL AGENT; CYCLOSPORIN; CYTOCHROME P450; CYTOCHROME P450 2C19; CYTOCHROME P450 2C8; CYTOCHROME P450 3A4; CYTOCHROME P450 3A5; DEBRISOQUINE 4 HYDROXYLASE; DILTIAZEM; DRUG METABOLITE; ENZYME INHIBITOR; ERYTHROMYCIN; HALOFANTRINE; KETOCONAZOLE; NIFEDIPINE; UNCLASSIFIED DRUG;

ARTICLE; CARDIOTOXICITY; CONTROLLED STUDY; DRUG METABOLISM; HUMAN; HUMAN CELL; LIVER MICROSOME; MICHAELIS CONSTANT; MICROSOME; NONHUMAN; YEAST;

ARYL HYDROCARBON HYDROXYLASES; BENZOFLAVONES; CYTOCHROME P-450 CYP2D6; CYTOCHROME P-450 ENZYME SYSTEM; ENZYME ACTIVATION; HUMANS; ISOENZYMES; KETOCONAZOLE; KINETICS; MICROSOMES; MICROSOMES, LIVER; MIXED FUNCTION OXYGENASES; PHENANTHRENES; SACCHAROMYCES CEREVISIAE; SUBSTRATE SPECIFICITY;

EID: 0033030589     PISSN: 00223573     EISSN: None     Source Type: Journal    
DOI: 10.1211/0022357991772628     Document Type: Article

References (37)

1. Beaune, P. H., Flinois, J. P., Kieffel, L., Kremers, P., Leroux, J. P. (1985) Purification of a new cytochrome P450 from human liver microsomes. Biochem. Biophys. Acta. 840: 364-370
2. Boudreau, E. F., Pang, L. W., Webster, H. K., Dixon, K. E., Pavanand, K. (1988) Malaria: treatment efficacy of halofantrine (Wr 171,669) in initial field trials in Thailand. Bull. WHO 66: 227-235
3. Bourrié, M., Meunier, V., Berger, Y., Fabre, G. (1996) Cytochrome P450 isoform inhibitors as a tool for the investigation of metabolic reactions catalysed by human liver microsomes. J. Pharmacol. Exp. Ther. 277: 321-332
4. Bradford, M. M. (1972) A rapid and sensitive method for the quantification of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72: 248-254
5. Cosgriff, T. M., Boudreau, E. F., Pamplin, C. L., Doberstyn, E. B., Desjardins, R. E. (1982) Evaluation of antimalarial activity of the phenanthrene methanol halofantrine. Am. J. Trop. Med. Hyg. 31: 1075-1079
6. Cullin, C., Pompon, D. (1988) Synthesis of functional mouse cytochrome P450 P1 and chemeric P40 P3-1 in the yeast Saccharomyces cervisiae. Gene 65: 203-217
7. De Waziers, I., Cugnenc, P., Yang, C. S., Leroux, J. P., Beaune, P. (1990) Cytochrome P450 isoenzymes, epoxide hydroxylase and glutathione transferase in rat and human hepatic and extrahepatic tissues. J. Pharmacol. Exp. Ther. 253: 387-394
8. Dragacci, S., Hamar-Hansen, C., Fournel-Gigleux, S., Lafaurie, C., Magdalou, J., Siest, G. (1987) Comparative study of clofibric acid and bilirubin glucuronidation in human liver microsomes. Biochem. Pharmacol. 36: 3923-3927
9. Erkko, P., Granlund, H., Nuutinen, M., Reitamo, S. (1997) Comparison of cyclosporine A pharmacokinetics of a new microemulsion formulation and standard oral preparation in patients with psoriasis. Br. J. Dermatol. 136: 82-88
10. Gimenez, F., Aubry, A.-F., Farinotti, R., Kirkland, K., Wainer, I. W. (1992) The determination of the enantiomers of halofantrine and monodesbutylhalofantrine in plasma and whole blood using sequential achiral/chiral high performance liquid chromatography. J. Pharm. Biomed. Anal. 10: 245-250
11. Graybill, J. R., Lundberg, D., Donovan, W., Levine, H. B., Rodriguez, M. D., Drutz, D. J. (1980) Treatment of coccidioidomycosis with ketoconazole: clinical and laboratory studies of 18 patients. Rev. Infect. Dis. 2: 661-673
12. Guengerich, F. P., Turvy, C. G. (1991) Comparison of levels of several human microsomal cytochrome P-450 enzymes and epoxide hydrolase in normal and disease states using immunochemical analysis of surgical liver samples. J. Pharmacol. Exp. Ther. 256: 1189-1194
13. Guengerich, F. P., Martin, M. V., Beaune, P. H., Kremers, P., Wolff, T., Waxman, D. J. (1986) Characterization of rat and human liver microsomal cytochrome P-450 forms involved in nifedipine oxidation drug metabolism. J. Biol. Chem. 261: 5051-5060
14. Halliday, R. C., Jones, B. C., Smith, D. A., Kitterincham, N. R., Park, B. K. (1995) An investigation of the interaction between halofantrine, CYP 2D6, CYP 3A4, studies with human liver microsomes and heterologous enzyme expression systems. Br. J. Clin. Pharmacol. 40: 369-378
15. Honig, P. K., Woosley, R. L., Zamani, K., Conner, D. P., Cantilena, L. R. (1992) Changes in the pharmacokinetics and electrocardiographic pharmacodynamics of terfenadine with concomitant administration of erythromycin. Clin. Pharmacol. Ther. 52: 231-238
16. Honig, P. K., Wortham, D. C., Zamani, K., Conner, D. P., Mullin, J. C., Cantilena, L. R. (1993) Terfenadine-ketoconazole interaction. Pharmacokinetic and electrocardiographic consequences. J. Am. Med. Assoc. 269: 1513-1518
17. Jakobsen, P., Lederballe, P. O., Mikkelsen, E. (1979) Gas chromatographic determination of nifedipine and one of its metabolites using electron-capture detection. J. Chromatogr. 162: 81-87
18. Karbwang, J., Na Bangchang, K. (1994) Clinical pharmaco-kinetics of halofantrine. Clin. Pharmacokinet. 27: 104-119
19. Kerlan, V., Dreano, Y., Bercovici, J. P., Beanne, P. H., Floch, H. H., Berthon, F. (1992) Nature of cytochromes P450 involved in the 2-/4-hydroxylations of estradiol in human liver microsomes. Biochem. Pharmacol. 44: 1745-1756
20. Koiwaya, Y., Matsuguchi, T., Nakamura, M., Etoh, A. (1981) Plasma concentrations of diltiazem after oral administration in coronary artery disease patients: a comparison with those in normal volunteers. Clin. Ther. 4: 127-132
21. Laemmli, U. K. (1970) Cleavage of structural proteins during the assembly of the head of bacteriophage. Nature 227: 680-685
22. Nosten, F., Ter Kuile, F., Chongsuphajaisiddhi, T., Webster, H. K., Edstein, M., Phapun, L., Thew, K. L., White, N. J. (1991) Mefloquine-resistant falciparum malaria on the Thai-Burmese border. Lancet 337: 1140-1143
23. Nosten, F., Ter Kuile, F., Luxemburger, C., Woodrow, C., Kyle, D. E., Chongsuphajaisiddhi, T., White, N. J. (1993) Cardiac effect of antimalarial treatment with halofantrine. Lancet 341: 1054-1056
24. Prichard, L., Fabre, I., Fabre, G., Domergue, J., Saint Aubert, B., Mourad, G., Maurel, P. (1990) Cyclosporin A drug interactions, screening for inducers and inhibitors of cytochrome P450 (cyclosporin A oxidase) in primary cultures of human hepatocytes and liver microsomes. Drug Metab. Dispos. 18: 595-606
25. Renaud, J. P., Cullin, C., Pompon, D., Beaune, P. H., Mansuy, D. (1990) Expression of human liver P450 3A4 in yeast. A functional model for the hepatic enzyme. Eur. J. Biochem. 194: 889-896
26. Segel, I. H. (1975) In: Enzyme Kinetics: Behavior and Analysis of Rapid Equilibrium and Steady-state Enzyme Systems, John Wiley and Sons, New York, pp 100-206
27. Sutton, D., Butler, A. M., Nadin, L., Murray, M. (1997) Role of CYP 3A4 in human hepatic diltiazem N-demethylation: inhibition of CYP 3A4 activity by oxidized diltiazem metabolites. J. Pharmacol. Exp. Ther. 282: 294-300
28. Tassaneeyakul, W., Veronese, M. E., Birkett, D. J., Gonzalez, F. J., Miners, J. O. (1993) Validation of 4-nitrophenol as an in-vitro substrate probe for human liver CYP 2E1 using cDNA expression and microsomal kinetic techniques. Biochem. Pharmacol. 46: 1975-1981
29. Ter Kuile, F. O., Dolan, G., Nosten, F., Edstein, M. D., Luxemburger, C., Phaipun, L., Chongsuphajaisiddhi, T., Webster, K., White, N. J. (1993) Halofantrine versus mefloquine in treatment of multidrug-resistant falciparum malaria. Lancet 341: 1044-1049
30. Transon, C., Lecoeur, S., Leemann, T., Beaune, P., Dayer, P. (1996) Interindividual variability in catalytic and immunoreactivity of three major human liver cytochrome P450 isozymes. Eur. J. Clin. Pharmacol. 51: 79-85
31. Truan, G., Cullin, C., Reisdorf, P., Urban, P., Pompon, D. (1993) Enhanced in vivo monoxygenase activities of mammalian P-450s in engineered yeast cells producing high level of NADPH P450 reductase and cytb5. Gene 125: 49-55
32. Von Moltke, L. L., Greenblatt, D. J., Cotreau-Bibbo, M. M., Harmatz, J. S., Shader, R. I. (1994) Inhibitors of alprazolam metabolism in vitro: effect of serotonin-reuptake-inhibitor antidepressants, ketoconazole and quinidine. Br. J. Clin. Pharmacol. 38: 23-31
33. Von Moltke, L. L., Greenblatt, D. J., Schmider, J., Harmatz, J. S., Shader, R. I. (1995) Metabolism of drugs by cytochrome P450 3A isoforms. Implications for drug interactions in psychopharmacology. Clin. Pharmacokinet. 29: 33-44
34. Washington, J. A., Wilson, W. R. (1985) A microbial and clinical perspective after 30 years of clinical use. Mayo Clin. Proc. 60: 189-203
35. Wrighton, S. A., Maurel, P., Schuetz, E. G., Watkins, P. B., Young, B., Guzelian, P. S. (1985) Identification of the cytochrome P450 induced by macrolide antibiotics in rat liver as the glucocorticoid responsive cytochrome P-450p. Biochemistry 25: 2171-2178
36. Wrighton, S. A., Brian, W. R., Sari, M.-A., Iwasaki, M., Guengerich, F. P., Raucy, J. L., Molowa, D. T., Vanderbranden, F. (1990) Studies on the expression and metabolic capabilities of human liver cytochrome P450IIIA5 (HLp3). Mol. Pharmacol. 38: 207-213
37. Yun, H. Y., Shimada, T., Guengerich, F. P. (1991) Purification and characterization of human liver microsomal cytochrome P-450 2A6. Mol. Pharmacol. 40: 679-685