Oxidative metabolism of clarithromycin in the presence of human liver microsomes: Major role for the cytochrome P4503A (CYP3A) subfamily

Drug Metabolism and Disposition

Volumn 25, Issue 5, 1997, Pages 623-630

  Rodrigues, A David ^a   Roberts, Ellen M ^b   Mulford, Darcy J ^b   Yao, Ye ^b   Quellet, Daniele ^b  

^a MERCK RESEARCH LABORATORIES   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

14 HYDROXYCLARITHROMYCIN; CLARITHROMYCIN; CYTOCHROME P450; DRUG METABOLITE; KETOCONAZOLE; NORCLARITHROMYCIN; TROLEANDOMYCIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; DEMETHYLATION; DRUG HYDROXYLATION; DRUG METABOLISM; HUMAN; HUMAN TISSUE; LIVER METABOLISM; LIVER MICROSOME; PRIORITY JOURNAL;

ANTI-BACTERIAL AGENTS; ARYL HYDROCARBON HYDROXYLASES; CLARITHROMYCIN; CYTOCHROME P-450 CYP3A; CYTOCHROME P-450 ENZYME SYSTEM; GENE EXPRESSION; HUMANS; MICROSOMES, LIVER; MIXED FUNCTION OXYGENASES; NADP; OXIDATION-REDUCTION; OXIDOREDUCTASES, N-DEMETHYLATING; RECOMBINANT PROTEINS; TUMOR CELLS, CULTURED;

INSECTA;

EID: 0030958315     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (33)

1. M. G. Sturgill and R. P. Rapp: Clarithromycin: review of a new macrolide antibiotic with improved microbiological spectrum and favorable pharmacokinetic and adverse effect profiles. Ann. Pharmacother. 26, 1099-1108 (1992).
2. F. Fraschini, F. Scaglione, and G. Demartini: Clarithromycin clinical pharmacokinetics. Clin. Pharmacokinet. 25, 189-204 (1993).
3. R. P. H. Logan, K. D. Bardhan, L. R. Celestin, A. Theodossi, K. Palmer, P. I. Reed, and R. Hallwas: Healing of DU and eradication of Helicobacter pylori. Lancet 106, A126 (1994).
4. A. Markham and D. McTavish: Clarithromycin and omeprazole: as Helicobacter pylori eradication therapy in patients with H. pylori-associated gastric disorders. Drugs 51, 161-178 (1996).
5. P. K. Honig, D. C. Wortham, K. Zamani, and L. R. Cantilena: Comparison of the effect of the macrolide antibiotics erythromycin, clarithromycin and azithromycin on terfenadine steady-state pharmacokinetics and electrocardiographic parameters. Drug invest. 7, 148-156 (1994).
6. I. S. Sketris, M. R. Wright, and M. L. West: Possible role of the intestinal P450 enzyme system in a cyclosporine-clarithromycin interaction. Pharmacotherapy 16, 301-305 (1996).
7. L. E. Gustavson, J. F. Kaiser, A. L. Edmonds, C. S. Locke, M. L. DeBartolo, and D. W. Schneck: Effect of omeprazole on concentrations of clarithromycin in plasma and gastric tissue at steady state. Antimicrob. Agents Chemother. 39, 2078-2083 (1995).
8. K. Wolter, K. Wagner, T. Philipp, and E. Fritschka: Interaction between FK 506 and clarithromycin in a renal transplant patient. Eur. J. Clin. Pharmacol. 47, 207-208 (1994).
9. T. M. Ludden: Pharmacokinetic interactions of the macrolide antibiotics. Clin. Pharmacokinet. 10, 63-79 (1985).
10. M. Tinel, V. Descatoire, D. Larrey, J. Loeper, G. Labbe, P. Letteron, and D. Pessayre: Effects of clarithromycin on cytochrome P450. Comparison with other macrolides. J. Pharmacol. Exp. Ther. 250, 746-751 (1989).
11. M. Delaforge, M. Jaouen, and D. Mansuy: Dual effects of macrolide antibiotics on rat liver cytochrome P450. Biochem. Pharmacol. 32, 2309-2318 (1983).
12. P. Periti, T. Mazzei, E. Mini, and A. Novelli: Pharmacokinetic drug interactions of macrolides. Clin. Pharmacokinet. 23, 106-131 (1992).
13. J. L. Ferrero, B. A. Bopp, K. C. Marsh, S. C. Quigley, M. J. Johnson, D. J. Anderson, J. E. Lamm, K. G. Tolman, S. W. Sanders, J. H. Cavanaugh, and R. C. Sonders: Metabolism and disposition of clarithromycin in man. Drug Metab. Dispos. 18, 441-446 (1990).
14. S. Y. Chu, D. S. Wilson, R. L. Deaton, A. V. Mackenthun, C. N. Eason, and J. H. Cavanaugh: Single-and multiple-dose pharmacokinetics of clarithromycin, a new macrolide antimicrobial. J. Clin. Pharmacol. 33, 719-726 (1993).
15. S. C. Piscitelli, L. H. Danziger, and K. A. Rodvold: Clarithromycin and azithromycin: new macrolide antibiotics. Clin. Pharmacol. 11, 137-152 (1992).
16. A. D. Rodrigues: Comparison of levels of aldehyde oxidase with cytochrome P450 activities in human liver in vitro. Biochem. Pharmacol. 48, 197-200 (1994).
17. J. M. Machinist, M. D. Mayer, M. S. Shet, J. L. Ferrero, and A. D. Rodrigues: Identification of the human liver cytochrome P450 enzymes involved in the metabolism of zileuton (ABT-077) and its N-dehydroxylated metabolite, Abbott-66193. Drug Metab. Dispos. 23, 1163-1174 (1995).
18. A. D. Rodrigues, M. J. Kukulka, E. M. Roberts, D. Quellet, and T. R. Rodgers: [O-methyl 14C]Naproxen O-demethylase activity in human liver microsomes: evidence for the involvement of cytochrome P4501A2 and CYP2C9/10. Drug Metab. Dispos. 24, 126-136 (1996).
19. A. D. Rodrigues, M. J. Kukulka, B. W. Suber, S. B. Thomas, J. T. Uchic, G. A. Rotert, G. Michel, B. Thome-Kromer, and J. M. Machinist: Measurement of liver microsomal cytochrome P450 (CYP2D6) activity using [O-methyl 14C]dextromethorphan. Anal. Biochem. 219, 309-320 (1994).
20. T. D. Lindstrom, B. R. Hanssen, and S. A. Wrighton: Cytochrome P450 complex formation by dirithromycin and other macrolides in rat and human livers. Antimicrob. Agents Chemother. 37, 265-269 (1993).
21. G. N. Kumar, A. D. Rodrigues, A. M. Buko, and J. F. Denissen: Cytochrome P450-mediated metabolism of the HIV-1 protease inhibitor ritonavir (ABT-538) in human liver microsomes. J. Pharmacol. Exp. Ther. 277, 423-431 (1996).
22. A. D. Rodrigues and S. L. Wong: Metabolism-based drug-drug interactions: in vitro-in vivo correlations and the Abbott Laboratories experience. In "Drug Interactions: Scientific and Regulatory Perspectives" (A. P. Li, ed.). Academic Press, San Diego, in press, 1997.
23. T. K. H. Chang, F. J. Gonzalez, and D. J. Waxman: Evaluation of triacetyloleandomycin, α-naphthoflavone and diethyldithiocarbamate as selective chemical probes for inhibition of human cytochromes P450. Arch. Biochem. Biophys. 311, 437-442 (1994).
24. D. Quellet, A. Hsu, G. R. Granneman, G. Carlson, H. Guenther, D. Mukherjee, C. Locke, and J. M. Leonard: Assessment of the pharmacokinetic interaction between ritonavir and clarithromycin. Clin. Pharmacol. Ther. 59, 143 (1996).
25. J. T. M. Buters, K. R. Korzekwa, K. L. Kunze, Y. Omata, J. P. Hardwick, and F. J. Gonzalez: cDNA-directed expression of human cytochrome P450 CYP3A4 using baculovirus. Drug Metab. Dispos. 22, 688-692 (1994).
26. T. Shimada, H. Yamazaki, M. Mimura, Y. Inui, and F. P. Guengerich: Interindividual variations in human liver cytochrome P450 enzymes involved in the oxidation of drug, carcinogens and toxic chemicals: studies with liver microsomes of 30 Japanese and 30 Caucasians. J. Pharmacol. Exp. Ther. 270, 414-423 (1994).
27. K. E. Thummel, D. O'Shea, M. F. Paine, D. D. Shen, K. L. Kunze, J. D. Perkins, and G. R. Wilkinson: Oral first-pass elimination of midazolam involves both gastrointestinal and hepatic CYP3A-mediated metabolism. Clin. Pharmacol. Ther. 59, 491-502 (1996).
28. A. D. Rodrigues, D. J. Mulford, R. D. Lee, B. W. Surber, M. J. Kukulka, J. L. Ferrero, S. B. Thomas, M. S. Shet, and R. W. Estabrook: In vitro metabolism of terfenadine by a purified recombinant fusion protein containing cytochrome P4503A4 and NADPH-P450 reductase. Comparison to human liver microsomes and precision-cut liver tissue slices. Drug Metab. Dispos. 23, 765-775 (1995).
29. J. C. Gorski, S. D. Hall, D. R. Jones, M. Vandenbranden, and S. A. Wrighton: Regioselective biotransformation of midazolam by members of the human cytochrome P450 3A (CYP3A) subfamily. Biochem. Pharmacol. 47, 1643-1653 (1994).
30. X. J. Zhang and P. E. Thomas: Erythromycin as a specific substrate for cytochrome P4503A isozymes and identification of a high affinity erythromycin N-demethylase in adult female rats. Drug Metab. Dispos. 24, 23-27 (1996).
31. H. Heyn, J. C. Stevens, and M. P. Marietta: The N-demethylation of S-mephenytoin by cytochromes P4502B6 and CYP3A4. Abstract of the 4th International ISSX Meeting, Seattle, WA, August 1995. ISSX Proc. 8, 73 (1996).
32. F. P. Guengerich: Cytochromes P450 of human liver. Classification and activity profiles of the major enzymes. In "Advances in Drug Metabolism in Man" (G. M. Pacifici and G. N. Fraccia, eds.), pp. 181-231. European Commission, Brussels, Belgium, 1995.
33. R. J. Wallace, B. A. Brown, D. E. Griffith, W. Girard, and K. Tanaka: Reduced serum levels of clarithromycin in patients treated with multidrug regimens including rifampin or rifabutin for Mycobacterium avium-M. intracellulare infection. J. Infect. Dis. 171, 747-750 (1995).