Metabolism of irinotecan (CPT-11) by human hepatic microsomes: Participation of cytochrome P-450 3A and drug interactions

Cancer Research

Volumn 58, Issue 3, 1998, Pages 468-472

  Haaz, Marie Christine ^a   Rivory, Laurent ^b   Riché, Christian ^c   Vernillet, Laurent ^d   Robert, Jacques ^a  

^a INSTITUT BERGONIÉ   (France)

^b ROYAL PRINCE ALFRED HOSPITAL   (Australia)

^c FACULTÉ DE MÉDECINE ET DES SCIENCES DE LA SANTÉ   (France)

^d SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

6BETA HYDROXYTESTOSTERONE HYDROXYLASE; 7 ETHYL 10 [4 N (5 AMINOPENTANOIC ACID) 1 PIPERIDINO]CARBONYLOXYCAMPTOTHECIN; ACETORPHAN; ALPHA NAPHTHOFLAVONE; AMIKACIN; CAMPTOTHECIN DERIVATIVE; CEFTRIAXONE; CHLORZOXAZONE; CIMETIDINE; CIPROFLOXACIN; COMPLEMENTARY DNA; COTRIMOXAZOLE; COUMARIN; CYTOCHROME P450 INHIBITOR; CYTOCHROME P450 ISOENZYME; DRUG METABOLITE; FLUOROURACIL; IRINOTECAN; IRINOTECAN CARBOXYLIC ACID; IRINOTECAN LACTONE; KETOCONAZOLE; LOPERAMIDE; METOCLOPRAMIDE; MORPHINE; ONDANSETRON; OXYGENASE; PARACETAMOL; QUINIDINE; RPR 121056; SULFAPHENAZOLE; TROLEANDOMYCIN; UNCLASSIFIED DRUG;

ARTICLE; COMPETITIVE INHIBITION; CONTROLLED STUDY; DRUG INTERACTION; DRUG METABOLISM; DRUG STRUCTURE; DRUG TRANSFORMATION; HUMAN; HUMAN CELL; LIVER MICROSOME; LYMPHOBLASTOID CELL; PRIORITY JOURNAL;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; ARYL HYDROCARBON HYDROXYLASES; BIOTRANSFORMATION; CAMPTOTHECIN; CYTOCHROME P-450 CYP3A; CYTOCHROME P-450 ENZYME SYSTEM; DRUG INTERACTIONS; ENZYME INHIBITORS; HUMANS; KETOCONAZOLE; MICROSOMES, LIVER; MOLECULAR STRUCTURE; OXIDOREDUCTASES, N-DEMETHYLATING; RECOMBINANT PROTEINS; STRUCTURE-ACTIVITY RELATIONSHIP; TRANSFECTION; TROLEANDOMYCIN;

EID: 0032005259     PISSN: 00085472     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (24)

1. Wall, M. E., Wani, M. C., Cook, C. E., Palmer, K. H., McPhail, A. T., and Sim, G. A. Plant antitumor agents. I. The isolation and structure of camptothecin, a novel alkaloidal leukemia and tumor inhibitor from Camptotheca acuminata. J. Am. Chem. Soc., 88: 3888-3890, 1966.
2. Slichenmeyer, W. J., Rowinsky, E. K., Donehower, D. C., and Kaufmann, S. H. The current status of camptothecin analogues as antitumor agents. J. Natl. Cancer Inst., 85: 271-291, 1993.
3. Kawato, Y., Aonuma, M., Hirota, Y., Kuga, H., and Sato, K. Intracellular roles of SN-38, a metabolite of the camptothecin derivative CPT-11, in the antitumor effects of CPT-11. Cancer Res., 51: 4187-4191, 1991.
4. Akimoto, K., Kawai, A., and Ohya, K. Kinetic studies of the hydrolysis and lactonization of camptothecin and its derivatives, CPT-11 and SN-38, in aqueous solution. Chem. Pharm. Bull. (Tokyo), 42: 2135-2138, 1994.
5. Rivory, L. P., and Robert, J. Identification and kinetics of a β-glucuronide metabolite of SN-38 in human plasma after administration of the camptothecin derivative irinotecan. Cancer Chemother. Pharmacol., 36: 176-179, 1995.
6. Haaz, M. C., Rivory, L. P., Jantet, S., Ratanasavanh, D., and Robert, J. Glucuronidation of SN-38, the active metabolite of irinotecan, by human hepatic microsomes. Pharmacol. Toxicol., 80: 91-96, 1997.
7. Rivory, L. P., Riou, J. F., Haaz, M. C., Sable, S., Vuilhorgne, M., Commerçon, A., Pond, S. M., and Robert, J. Identification and properties of a major plasma metabolite of irinotecan (CPT-11) isolated from the plasma of patients. Cancer Res., 56: 3689-3694, 1996.
8. Lewis, A. D., Lau, D. H. M., Duran, G. E., Wolf, C. R., and Sikic, B. I. Role of cytochrome P-450 from the human CYP 3A gene family in the potentiation of morpholino doxorubicin by human liver microsomes. Cancer Res., 52: 4379-4384, 1992.
9. Kivistö, K. T., Kroemer, H. K., and Eichelbaum, M. The role of human cytochrome P450 enzymes in the metabolism of anticancer agents: implications for drug interactions. Br. J. Clin. Pharmacol., 40: 523-530, 1995.
10. Royer, I., Monsarrat, B., Sonnier, M., Wright, M., and Cresteil, T. Metabolism of docetaxel by human cytochromes P450: interactions with paclitaxel and other antineoplastic drugs. Cancer Res., 56: 58-65, 1996.
11. Rivory, L. P., Haaz, M. C., Canal, P., Lokiec, F., Armand, J. P., and Robert, J. Pharmacokinetic interrelationships of irinotecan (CPT-11) and its three major plasma metabolites in patients enrolled in Phase I/II trials. Clin. Cancer Res., 3: 1261-1266, 1997.
12. Berthou, F., Ratanasavanh, D., Riché, C., Picart, D., Voisin, T., and Guillouzo, A. Comparison of caffeine metabolism by slices, microsomes and hepatocyte cultures from adult human liver. Xenobiotica, 19: 401-407, 1989.
13. Rivory, L. P., and Robert, J. Reversed-phase high-performance liquid chromatographic method for the simultaneous quantitation of the carboxylate and lactone forms of the camptothecin derivative irinotecan, CPT-11, and its metabolite SN-38 in plasma. J. Chromatogr., 661B: 133-141, 1994.
14. Halpert, J. R., Guengerich, F. P., Bend, J. R., and Correia, M. A. Selective inhibitors of cytochromes P450. Toxicol. Appl. Pharmacol., 125: 163-175, 1994.
15. Laemmli, U. K. Cleavage of structural proteins during the assembly of head of bacteriophage T4. Nature (Lond.), 227: 680-685, 1970.
16. Bourzat, J. D., Vuilhorgne, M., Rivory, L. P., Robert, J., and Commerçon, A. Semisynthesis of RPR 121056A, a major metabolite of irinotecan (CPT-11). Tetrahedron Lett., 37: 6327-6330, 1996.
17. Haaz, M. C., Rivory, L. P., Riché, C., and Robert, J. The transformation of irinotecan (CPT-11) to its active metabolite SN-38 by human liver microsomes: differential hydrolysis for the lactone and carboxylate forms. Naunyn-Schmiedeberg's Arch. Pharmacol., 356: 257-262, 1997.
18. Ladona, M., Spalding, D. J. M., Ekman, L., Lindström, B., and Rane, A. Human fetal and adult liver metabolism of ethylmorphine. Relation to immunodetected cytochrome P-450 PCN and interactions with important fetal corticosteroids. Biochem. Pharmacol., 38: 3147-3155, 1989.
19. Waxman, D., Attisano, C., Guengerich, F. P., and Laperson, D. P. Human liver microsomal steroid metabolism: identification of the major steroid hormone 6β-hydroxylase cytochrome P450 enzyme. Arch. Biochem. Biophys., 263: 424-436, 1988.
20. Watkins, P. B., Wrighton, S. A., Maurel, P., Schuetz, E. G., Mendez-Picon, G., Parker, G. A., and Guzelian, P. S. Identification of an inducible form of cytochrome P450 in human liver. Proc. Natl. Acad. Sci. USA, 82: 6310-6314, 1985.
21. Zhou, X. J., Zhou-Pan, X. R., Gauthier, T., Placidi, M., Maurel, P., and Rahmani, R. Human liver microsomal cytochrome P4503A isozymes mediated vindesine biotransformation. Biochem. Pharmacol., 45: 853-861, 1993.
22. Jacolot, F., Simon, I., Dreano, Y., Beaune, P., Riché, C., and Berthou, F. Identification of the cytochrome P450 IIIA family as the enzymes involved in the N-demethylation of tamoxifen in human liver microsomes. Biochem. Pharmacol., 41: 1911-1919, 1991.
23. Lauritsen, K., Laursen, L. S., and Rask-Madsen, J. Clinical pharmacokinetics of drugs used in the treatment of gastrointestinal diseases. Clin. Pharmacokin., 19: 94-125, 1990.
24. Dixon, C. M., Colthup, P. V., Serabjit-Singh, C. J., Kerr, B. M., Boehlert, C. C., Park, G. R., and Tarbit, M. H. Multiple forms of cytochrome P450 are involved in the metabolism of ondansetron in humans. Drug Metab. Dispos., 23: 1225-1230, 1995.