The in vitro hepatic metabolism of quinine in mice, rats and dogs: Comparison with human liver microsomes

Journal of Pharmacology and Experimental Therapeutics

Volumn 283, Issue 3, 1997, Pages 1168-1176

  Zhao, Xue Jun ^a   Ishizaki, Takashi ^a  

^a NATIONAL CENTER FOR GLOBAL HEALTH AND MEDICINE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXYQUININE; 4 NITROPHENOL; ALPHA NAPHTHOFLAVONE; ANTIMALARIAL AGENT; CHLOROQUINE; COUMARIN ANTICOAGULANT; DIAZEPAM; DOXYCYCLINE; KETOCONAZOLE; PHENYTOIN; PRIMAQUINE; PROGUANIL; QUININE; QUININE DERIVATIVE; SULFAPHENAZOLE; TETRACYCLINE; TROLEANDOMYCIN; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ANTIMALARIAL ACTIVITY; ARTICLE; DOG; DRUG HYDROXYLATION; DRUG METABOLISM; ENZYME ACTIVITY; HUMAN; HUMAN TISSUE; LIVER METABOLISM; LIVER MICROSOME; MALE; MOUSE; NONHUMAN; PRIORITY JOURNAL; SPECIES DIFFERENCE;

ANIMALS; ANTIMALARIALS; CYTOCHROME P-450 ENZYME SYSTEM; DOGS; DRUG INTERACTIONS; HUMANS; MALE; MICE; MICROSOMES, LIVER; QUININE; RATS; RATS, WISTAR; SPECIES SPECIFICITY;

EID: 0031458032     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (45)

1. ANDERSSON, T., MINERS, J. O., VERONESE, M. E. AND BIRKETT, D. J.: Diazepam metabolism by human liver microsomes is mediated by both S-mephenytoin hydroxylase and CYP3A isoforms. Br. J. Clin. Pharmacol. 38:131-137, 1994.
2. BERTHOU, F., DREANO, Y., BELLOC, C., KANGAS, L., GAUTIER, J. C. AND BEAUNE, P.: Involvement of cytochrome P4503A enzyme family in the major metabolic pathways of toremifene in human liver microsomes. Biochem. Pharmacol. 47: 1883-1895, 1994.
3. BOELE VAN HENSBROEK, M., ONYIORAH, E., JAFFAR, S., SCHNEIDER, G., PALMER, A., FRENKEL, J., ENWERE, G., FORCK, S., NUSMEIJER, A., BENNETT, S., GREENWOOD, B. AND KWIATKOWSKI, D.: A trial of artemether or quinine in children with cerebral malaria. N. Engl. J. Med. 335: 76-83, 1996.
4. BOURRIE, M., MEUNIER, V., BERGER, Y. AND FABRE, G.: Cytochrome P450 isoform inhibitions as a tool for the investigation of metabolic reactions catalyzed by human liver microsomes. J. Pharmacol. Exp. Ther. 277: 321-332, 1996.
5. BRADLEY, D.: Prophylaxis against malaria for travellers from the United Kingdom. Br. Med. J. 306: 1247-1252, 1993.
6. CHANG, T., GONZALEZ, F. AND WAXMAN, D.: Evaluation of triacetyloleandomycin, α-naphthoflavone and diethyldithiocarbamate as selective chemical probes for inhibition of human cytochromes P450. Arch. Biochem. Biophys. 311: 437-442, 1994.
7. CHIBA, K., KOBAYASHI, K., MANABE, K., TANI, M., KAMATAKI, T. AND ISHIZAKI, T.: Oxidative metabolism of omeprazole in human liver microsomes: Cosegregation with S-mephenytoin 4′-hydroxylation. J. Pharmacol. Exp. Ther. 266: 52-59, 1993.
8. EAGLING, V. A., TJIA, J. F. AND BACK, D. J.: Differential selectivity of cytochrome P450 inhibitors against four probe substrates in human and rat liver microsomes. Br. J. Clin. Pharmacol. 42: 673P, 1996.
9. ECHIZEN, H., KAWASAKI, H., CHIBA, K., TANI, M. AND ISHIZAKI, T.: A potent inhibition effect of erythromycin and other macrolide antibiotics on the mono-N-dealkylation metabolism of disopyramide with human liver microsomes. J. Pharmacol. Exp. Ther. 264: 1425-1431, 1993.
10. EGUCHI, K., NISHIBE, T., BABA, T. AND OHNO, K.: Quantitation of cytochrome P450 enzymes (CYP1A1/2, 2B11, 2C21 and 3A12) in dog liver microsomes by enzyme-linked immunosorbent assay. Xenobiotica 26: 755-764, 1996.
11. FORKERT, P. G., REDZA, Z. M., MANGOS, S., PARK, S. S. AND TAM, S. P.: Induction and regulation of CYP2E1 in murine liver after acute and chronic acetone administration. Drug Metab. Dispos. 22: 248-253, 1994.
12. FUNAE, Y. AND IMAOKA, S.: Cytochrome P450 in rodents. In Handbook of Experimental Pharmacology, ed. by J. B. Schenkman and H. Greim, Vol. 105, pp. 221-238, Springer-Verlag, Berlin, 1993.
13. GOLDSTEIN, J. A. AND DE MORAIS, S. M. F.: Biochemistry and molecular biology of the human CYP2C subfamily. Pharmacogenetics 4: 285-299, 1994.
14. GUENGERICH, F. P., MULLER-ENOCH, D., AND BLAIR, I. A.: Oxidation of quinidine by liver cytochrome P-450. Mol. Pharmacol. 30: 287-295, 1986.
15. HIEN, T. T., DAY, N. P. J., PHU, N. H., MAI, N. T. H., CHAU, T. T. H., LOC, P. P., SINH, D. X., CHUONG, L. V., VINH, H., WALLER, D., PETO, T. E. A. AND WHITE, N. J.: A controlled trial of artemether or quinine in Vietnamese adults with severe falciparum malaria. N. Engl. J. Med. 335: 76-83, 1996.
16. HIEN, T. T. AND WHITE, N. J.: Qinghaosu. Lancet 341: 603-608, 1993.
17. KOBAYASHI, S., MURRAY, S., WATSON, D., SESARDIC, D., DAVIES, D. S. AND BOOBIS, A. R.: The specificity of inhibition of debrisoquine 4-hydroxylase activity by quinidine and quinine is the inverse of that in man. Biochem. Pharmacol. 38: 2795-2799, 1989.
18. KUNZE, K. L. AND TRAGER, W. F.: Isoform-selective mechanism-based inhibition of human cytochrome P450 1A2 by furafylline. Chem. Res. Toxicol. 6: 649-656, 1993.
19. LOWRY, O. H., ROSEBROUGH, N. J., FARR, A. L. AND RANDALL, R. J.: Protein measurement with the Folin phenol reagent. J. Biol. Chem. 193: 265-275, 1951.
20. MONOSTORY, K. AND VERECZKEY, L.: The effect of phenobarbital and dexamethasone coadministration on the activity of rat liver P450 system. Biochem. Biophys. Res. Comm. 203: 351-358, 1994.
21. MORAN, J. S. AND BERNARD, K. W.: The spread of chloroquine-resistant malaria in Africa. Implication for travelers. JAMA 262: 245-248, 1989.
22. NEDELCHEVA, V. AND GUT, I.: P450 in the rat and man: Methods of investigation, substrate specificities and relevance to cancer. Xenobiotica 24: 1151-1175, 1994.
23. NELSON, D. R., KOYMANS, L., KAMATAKI, T., STEGEMAN, J. J., FEYEREISEN, R., WAXMAN, D. J., WATERMAN, M. R., GOTOH, O., COON, M. J., ESTABROOK, R. W., GUNSALUS, I. C. AND NEBERT, D. W.: P450 superfamily: Update on new sequence, gene mapping, accession numbers and nomenclature. Pharmacogenetics 6: 1-42, 1996.
24. NEWTON, D. J., WANG, R. W. AND LU, A. Y. H.: Cytochrome P450 inhibitors: Evaluation of specificities in the in vitro metabolism of therapeutic agents by human liver microsomes. Drug Metab. Dispos. 23: 154-158, 1995.
25. PEARCE, R. E., RODRIGUES, A. D., GOLDSTEIN, J. A. AND PARKINSON, A.: Identification of the human P450 enzymes involved in lansoprazole metabolism. J. Pharmacol. Exp. Ther. 277: 805-816, 1996.
26. 1. Chem. Res. Toxicol. 5: 202-210, 1992.
27. SHOU, M., GROGAN, J., MANCENWICZ, J., KRAUSZ, K., GONZALEZ, F., GELBOIN, H. AND KORZEKWA, K.: Activation of CYP3A4: Evidence for the simultaneous binding of two substrates in a cytochrome P450 active site. Biochemistry 33: 6450-6455, 1994.
28. SOUCEK, P. AND GUT, I.: Cytochrome P-450 in rats: Structures, functions, properties and relevant forms. Xenobiotica 22: 83-103, 1992.
29. TASSANEEYAKUL, W., VERONESE, M. E., BIRKETT, D. J., GONZALEZ, F. J. AND MINERS, J. O.: Validation of 4-nitrophenol as an in vitro substrate probe for human liver CYP2E1 using cDNA expression and microsomal kinetic techniques. Biochem. Pharmacol. 46: 1751-1981, 1993.
30. TRACY, J. W. AND WEBSTER, L. T.: Drugs used in the chemotherapy of protozoal infections. Malaria. In Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed., ed. by J. G. Hardman, L. E. Limbird, R. W. Ruddon and A. G. Gilman, pp. 956-248, McGraw-Hill, New York, 1996.
31. WANWIMOLRUK, S., WONG, S. M., ZHANG, H. AND COVILLE, P. F.: Simultaneous determination of quinine and a major metabolite 3-hydroxyquinine in biological fluids by HPLC without extraction. J. Liq. Chromatogr. 19: 293-305, 1996.
32. WANWIMOLRUK, S., WONG, S. M., ZHANG, H., COVILLE, P. F. AND WALKER, R. J.: Metabolism of quinine in man: Identification of a major metabolite, and effects of smoking and rifampicin pretreatment. J. Pharm. Pharmacol. 47: 957-963, 1995.
33. WATKINS, P. B., WRIGHTON, S. A., MAUREL, J. P., PCHUETZ, E. G., MENDEZ-PICON, G., PARKER, G. A. AND GUZELIAN, P. S.: Identification of an inducible form of cytochrome P-450 in human liver. Proc. Natl. Acad. Sci. (U.S.A.) 82: 6310-6314, 1985.
34. WERNSDORFER, W. H.: The development and spread of drug-resistant malaria. Parasitol. Today 7: 297-303, 1991.
35. WHITE, N. J.: Drug treatment and prevention of malaria. Eur. J. Clin. Pharmacol. 34: 1-14, 1988.
36. WHITE, N. J.: Antimalarial pharmacokinetics and treatment regimens. Br. J. Clin. Pharmacol. 34: 1-10, 1992.
37. WHITE, N. J.: The treatment of malaria. N. Engl. J. Med. 335: 800-806, 1996.
38. WHITE, N. J., LOOAREESUWAN, S., WARRELL, D. A., WARRELL, M. J., BUNNAG, D. AND HARINASUTA, T.: Quinine pharmacokinetics and toxicity in cerebral and uncomplicated falciparum malaria. Am. J. Med. 73: 564-572, 1982.
39. WRIGHTON, S. A. AND STEVENS, J. C.: The human hepatic cytochromes P450 involved in drug metabolism. Crit. Rev. Toxicol. 22: 1-22, 1992.
40. YAMAOKA, K., TANIGAWARA, Y., NAKAGAWA, T. AND UNO, J.: A pharmacokinetic analysis program (MULTI) for microcomputer. J. Pharm. Dyn. 4: 879-885, 1981.
41. YASUMORI, T., MURAYAMA, N., YAMAZOE, Y. AND KATO, R.: Polymorphism in hydroxylation of mephenytoin and hexobarbital stereoisomers in relation to hepatic P-450 human-2. Clin. Pharmacol. Ther. 47: 313-322, 1990.
42. YUN, C. H., WOOD, M. AND GUENGERICH, F. P.: Identification of the pharmacogenetic determinants of alfentanil metabolism: Cytochrome P4503A. Anesthesiology 77: 467-474, 1992.
43. ZHANG, H., COVILLE, P. F., WALKER, R. J., MINERS, J. O., BIRKETT, D. J. AND WANWIMOLRUK, S.: Metabolism of quinine in humans: Evidence for the involvement of human CYP3A in the hepatic metabolism of quinine. Br. J. Clin. Pharmacol. 43: 245-252, 1997.
44. ZHAO, X-J., AND ISHIZAKI, T.: Metabolic interactions of selected antimalarial and non-antimalarial drugs with the major pathway (3-hydroxylation) of quinine in human liver microsomes. Br. J. Clin. Pharmacol., 1997, in press.
45. ZHAO, X-J., YOKOYAMA, H., CHIBA, K., WANWIMOLRUK, S. AND ISHIZAKI, T.: Identification of human cytochrome P450 isoforms involved in the 3-hydroxylation of quinine by human liver microsomes and nine recombinant human cytochromes P450. J. Pharmacol. Exp. Ther. 279: 1327-1334, 1996.