Hepatic biotransformation of docetaxel (Taxotere®) in vitro: Involvement of the CYP3A subfamily in humans

Cancer Research

Volumn 56, Issue 6, 1996, Pages 1296-1302

  Marre, Françoise ^a,c   Sanderink, Ger Jan ^b   De Sousa, Georges ^a   Gaillard, Claude ^b   Martinet, Michel ^b   Rahmani, Roger ^a  

^a INSERM   (France)

^b SANOFI   (France)

^c UNIVERSITY OF LIMOGES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CIMETIDINE; CISPLATIN; CYCLOPHOSPHAMIDE; CYTARABINE; DEXAMETHASONE; DIAZEPAM; DOCETAXEL; DOXORUBICIN; ERYTHROMYCIN; ETOPOSIDE; FLUOROURACIL; IMIPRAMINE; INTOPLICINE; KETOCONAZOLE; MIDAZOLAM; NIFEDIPINE; OMEPRAZOLE; PARACETAMOL; RANITIDINE; RIFAMPICIN; TROLEANDOMYCIN; VIDARABINE; VINBLASTINE; VINCA ALKALOID; VINCRISTINE;

ANIMAL CELL; ARTICLE; CANCER CHEMOTHERAPY; DOG; DRUG DETERMINATION; DRUG METABOLISM; DRUG TRANSFORMATION; HUMAN; HUMAN CELL; LIVER CELL CULTURE; LIVER MICROSOME METABOLISM; MOUSE; NONHUMAN; PRIORITY JOURNAL; RAT;

ANIMALS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; BIOTRANSFORMATION; CYTOCHROME P-450 CYP2E1; CYTOCHROME P-450 ENZYME SYSTEM; DOGS; DRUG INTERACTIONS; HUMANS; MALE; MICE; MICROSOMES, LIVER; MIXED FUNCTION OXYGENASES; OXYGENASES; PACLITAXEL; RATS; SPECIES SPECIFICITY; SUBSTRATE SPECIFICITY; TAXOIDS;

EID: 0029937721     PISSN: 00085472     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (38)

1. Gueritte-Voegelein, F., Guenard, D., Lavelle, F., Le Goff, M. T., Mangatal, L., and Potier, P. Relationships between the structure of Taxol analogues and their metabolic activity. J Med. Chem., 34: 992-998, 1991.
2. Ringel, I., and Horwitz, S B. Studies with RP 56976 (Taxotere), a semisynthetic analogue of Taxol. J. Natl. Cancer Inst., 83: 288-291, 1991.
3. Bissery, M. C., Guenard, D., Gueritte-Voegelein, F., and Lavelle, F Experimental antitumor activity of Taxotere (RP 56976, NSC 628503), a Taxol analogue. Cancer Res , 51: 4845-4852, 1991.
4. ®): a review of preclinical and clinical experience. Part I. preclinical experience Anticancer Drugs, 6: 339-368, 1995.
5. ™ (docetaxel) Cancer Surv, 17: 305-313, 1993.
6. ®) metabolism in the rat in vivo and in vitro. Proc. Am. Assoc. Cancer Res., 35: 428, 1994
7. 14C-radiolabelled Taxotere (TXT) (RP56976, NSC628503) in cancer patients. Proc. Am. Assoc Cancer Res., 34: 373, 1993
8. Vuilhorgne, M., Gaillard, C , Sanderink, G. J., Royer, I., Monsarrat, B , Dubois, and Wright, M. Metabolism of taxoid drugs. ACS (Am. Chem. Soc.) Symp. Ser., 583: 98-110, 1995
9. Nebert, D. W , Adesnik, M., Coon, M. J., Estabrook, R. W., Gonzalez, F. J., Guengerich, F. P., Gunsalus, I. C., Johnson, E. F , Kemper, B., Levin, W., Phillips, I. R., Sato, R., and Waterman, M R The P450 gene superfamily: recommended nomenclature. DNA, 6: 1-11, 1987.
10. Guengerich, F. P. Roles of cytochrome P450 enzymes in chemical carcinogenesis and cancer chemotherapy. Cancer Res , 48: 2946-2954, 1988.
11. 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.
12. Zhou-Pan, X R , Zhou-Pan X., Placidi, M., Maurel, P., Barra, Y, Rahmani, R. Involvement of human liver cytochrome P450 3A in vinblastine metabolism: drug interactions. Cancer Res., 53: 5121-5126, 1993.
13. Cresteil, T., Monsarrat, B , Alvinerie, P., Tréluyer, J. M., Vieira, I., and Wright, M. Taxol metabolism by human liver microsomes identification of cytochrome P450 isozymes involved in its biotransformation Cancer Res., 54: 386-393, 1994.
14. Van der Hoeven, T A , and Coon, M J. Preparation and properties of partially purified cytochrome P-450 and reduced nicotinamide adenine dinucleotide phosphate-cytochrome P-450 reductase from rabbit liver microsomes. J. Biol. Chem , 249: 6302-6310, 1974.
15. Bradford, M. A rapid and sensitive method for the quantification of microgram quantises of protein utilizing the principle of protein dye binding. Anal. Biochem , 72: 248-254, 1976.
16. Omura, T , and Sato, R. The carbon monoxyde-binding pigment of liver microsomes. I Evidence of its hemoprotein nature J. Biol. Chem., 239: 2370-2378, 1964.
17. Nash, T. The coloric estimation of formaldehyde by means of the Hantzsch reaction. Biochem. J., 55: 516-521, 1953.
18. Mieyal, J. J , and Blumer, J L. Acceleration of the autooxidation of human oxyhemoglobin by aniline and its relation to hemoglobin-catalyzed aniline hydroxylation. J. Biol Chem., 251: 3442-3446, 1976.
19. Marre, F., Fabre, G., Lacarelle, B., Bourrie, M., Catalin, J , Berger, Y., Rahmani, R., and Cano, J. P. Involvement of the cytochrome P450IID subfamily in minaprine 4-hydroxylation by human hepatic microsomes. Drug Metab. Dispos., 20: 316-321, 1992.
20. Dou, M., de Sousa, G., Lacarelle, B., Placidi, M., Lechene de la Porte, P., Domingo, M., Lafont, H , and Rahmani, R. Thawed human hepatocytes in primary culture. Cryobiology, 29. 454-469, 1992.
21. Commerçon, A., Bourzat, J. D , Bézard, D., and Vuilhorgne, M Partial synthesis of major human metabolites of docetaxel. Tetrahedron, 50: 10289-10298, 1994.
22. 14C]-Docetaxel (Taxotere®) disposition in the isolated perfused rat liver. Eur. J Drug Metab. Pharmacokinet., 19 (Suppl. 2): 29, 1994.
23. Babany, G., Larrey, D., and Pessayre, D. Macrolide antibiotics as inducers and inhibitors of cytochrome P-450 in experimental animals and man. In: G. G. Gibson (ed.), Progress in Drug Metabolism, Vol. 12, pp. 61-98. London. Taylor and Francis, 1988.
24. Guengerich, F. P., Martin, V. P., Beaune, P. H., Kremers, P., Wolff, T., and Waxman, D J Characterization of rat and human liver microsomal cytochrome P-450 forms involved in nifedipine oxidation, a prototype for genetic polymorphism in oxidative drug metabolism. J. Biol. Chem., 261: 5051-5060, 1986
25. Back, D. J., and Tjia, J F. Comparative effects of the antimycotic drugs ketoconazole. fluconazole, itraconazole and terbinafine on the metabolism of cyclosporin by human liver microsomes. Br J. Clin. Pharmacol., 32: 624-626, 1991.
26. Watkins, P. B. Noninvasive tests of CYP3A enzymes Pharmacogenetics, 4: 171-187, 1994.
27. Kerlan, V , Dreano, Y., Bercovivi, J. P , Beaune, P. H., Floch, H H., and Berthou, F. Nature of cytochrome P450 involved in the 2-/4-hydroxylations of estradiol in human liver microsomes. Biochem Pharmacol., 44: 1745-1756, 1992.
28. Bargetzi, M. J., Aoyama, T., Gonzalez, F. J., and Meyer, U. A. Lidocaine metabolism in human liver microsomes by cytochrome P450IIIA4. Clin. Pharmacol. Ther., 46: 521-527, 1989
29. Otton, S V., Inaba, T., and Kalow, W. Competitive inhibition of sparteine oxidation in human liver by β-adrenoreceptor antagonists and other cardiovascular drugs Life Sci., 34: 73-80, 1984.
30. Guengerich, F. P , Müller-Enoch, D., and Blair, I. A. Oxidation of quinidine by human liver cytochrome P-450 Mol Pharmacol., 30: 287-295, 1986.
31. Cummings, J., Allan, L , Willmott, N., Riley, R., Workman, P., and Smyth, J F. The enzymology of doxorubicin quinone reduction in tumour tissue. Biochem. Pharmacol., 44: 2175-2183, 1992.
32. Bertillson, L., Henthorn, T K , Sanz, E., Tybring, G., Sawe, J., and Villen, T. Importance of genetic factors in the regulation of diazepam metabolism: relationship to S-mephenytoin, but not debrisoquin, hydroxylation type. Clin. Pharmacol. Ther., 45: 348-355, 1989
33. Andersson, T., Regardh, C. G , Dahl-Puustinen, M., and Bertillson, L. Slow omeprazole metabolizers are also poor S-mephenytoin hydroxylators. Ther. Drug Monit., 12: 415-416, 1990
34. Skjelbo, E., and Brosen, K. Inhibitors of imipramine metabolism by human liver microsomes. Br J. Clin. Pharmacol., 34: 256-261, 1992.
35. Lemoine, A., Gautier, J. C., Azoulay, D., Kiffel, L., Belloc, C., Guengerich, F. P., Maurel, P., Beaune, P , and Leroux, J. P Major pathway of imipramine metabolism is catalyzed by cytochromes P-450 1A2 and P-450 3A4 in human liver. Mol. Pharmacol., 43: 827-832, 1993.
36. Raucy, J. L., Lasker, J. M., Lieber, C. S., and Black, M. Acetaminophen activation by human liver microsomes P450IIE1 and P450IA2. Arch. Biochem. Biophys., 271: 270-283, 1989.
37. Pichard, L., Fabre, I., Fabre, G., Domergue, J., Saint Aubert, J., Mourad, G., and Maurel, P. Cyclosporin drug interactions: screening for inducers and inhibitors of cytochrome P-450 (cyclosporin A oxidase) in primary cultures of human hepatocytes and in liver microsomes. Drug Metab. Dispos., 18: 595-606, 1990.
38. Bruno, R , Vergniol, J. C., Montay, G., Le Bail, N., Frydman, A., Clavel, M., and Marty, M. Clinical pharmacology of Taxotere (RP56976) given as 1-2 hour infusion every 2-3 weeks Proc. Am. Assoc Cancer Res., 33: 261, 1992