Bioactivation of the anticancer agent CPT-11 to SN-38 by human hepatic microsomal carboxylesterases and the in vitro assessment of potential drug interactions

Drug Metabolism and Disposition

Volumn 25, Issue 10, 1997, Pages 1157-1164

  Slatter, J Greg ^a   Su, Ping ^b   Sams, James P ^b   Schaaf, Larry J ^b   Wienkers, Larry C ^b  

^a PFIZER INC   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

1 NAPHTHYL ACETATE; 7 ETHYL 10 HYDROXYCAMPTOTHECIN; ANTINEOPLASTIC AGENT; CAMPTOTHECIN; CARBOXYLESTERASE; FLUORIDE; FLUORIDE SODIUM; IRINOTECAN; LIVER ENZYME; METOCLOPRAMIDE; MICROSOME ENZYME; PARACETAMOL; PHYSOSTIGMINE; PROBENECID;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER INHIBITION; CONTROLLED STUDY; ENZYME MECHANISM; ENZYME POLYMORPHISM; ENZYME SUBSTRATE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN TISSUE; PRIORITY JOURNAL;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; BIOTRANSFORMATION; CAMPTOTHECIN; CARBOXYLIC ESTER HYDROLASES; DRUG INTERACTIONS; HUMANS; MICROSOMES, LIVER;

EID: 0030863434     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (41)

1. W. J. Slichenmyer, E. K. Rowinsky. R C. Donehower, and S. H. Kaufmann: The current status of camptothecin analogues as antitumor agents. J. Natl. Cancer Inst. 85, 271-291 (1993).
2. G. J. Creemers, B. Lund, and J. Verweij: Topoisomerase I inhibitors: Topotecan and irinotecan. Cancer Treat. Rev. 20, 73-96 (1994).
3. V S. Sawada, T. Yokokura, and T. Miyasaka: Synthesis and antitumor activity of A-ring or E-lactone modified water-soluble prodrugs of 20(s) camptothecin. including development of irinotecan hydrochloride trihydrate. Curr. Pharm. Design. 1, 113-132 (1995).
4. T. G. Burke and Z. Mi: The structural basis of camptothecin interactions with human serum albumin: impact on drug stability. J. Med. Chem. 37, 40-46 (1994).
5. A. Kono and Y. Hara: Conversion of CPT-11 into SN-38 in human tissues. Jpn. J. Cancer Chemother. 18, 2175-2178 (1991).
6. Y. Kawato, M. Aonuma, K. Matsumoto, and K. Sato: Production of SN-38. a main metabolite of the camptothecin derivative CPT-11, and its species and tissue specificities. Yakubutsu Dotai 6, 899-907 (1991).
7. T. Satoh, M. Hosokawa, R. Atsumi, W. Suzuki, H. Hakusui, and E. Nagai: Metabolic activation of CPT-11. 7-ethyl-10-[4-(1-piperidino)-1-piper- idinojcarbonyloxycamptothecin. a novel antitumor agent. by carboxylesterase. Biol. Pharm. Bull. 17, 662-664 (1994).
8. L. P. Rivory, M. R. Bowles, J. Robert, and S. M. Pond: Conversion of irinotecan (CPT-11) to its active metabolite, 7-ethyl-10-hydroxycamptothecin (SN-38). by human liver carboxylesterase. Biochem. Pharmacol. 52, 1103-1111 (1996).
9. T. Satoh: Role of carboxylesterases in xenobiotic metabolism In: "Reviews in Biochemical Toxicology" (E. Hodgson. J. R. Bend. R. M. Philpot. eds.) pp. 155-181. Elsevier. New York (1987).
10. D. A. Haugen and J. W. Suttie: Fluoride inhibition of rat microsomal esterase. J. Biol. Chem. 249, 2723-2731 (1974).
11. T. Tsuji, N. Kaneda, K. Kado, T. Yokokura. T. Yoshimoto, and D. Tsuru: CPT-11 converting enzyme from rat serum: purification and some properties. J. Pharmacobiodyn. 14, 341-349 (1991).
12. S. S. Rao and U. Kaveeshwar: Difference in the inhibition of plasma carboxylesterase activity by metoclopramide in humans and laboratory animals. Pharmazie 47, 115 (1992).
13. O. T. Markovic and N. S. Markovic: Chlorpronmazine induced inhibition of carboxylesterase activity. J. Histochem. Cytochem. 39, 730 (1991).
14. T. L. Huang, A. Székács, T. Uematsu, E. Kuwano, A. Parkinson, and B. D. Hammock: Hydrolysis of carbonates, thiocarbonates, carbarmates, and carboxylic esters of α-naphthol. β-naphthol, and p-nitrophenol by human, rat, and mouse liver carboxylesterases, Pharm. Res. 10, 639-648 (1993).
15. D. F. Grant. D. M. Bender, and B. D. Hammock: Quantitative kinetic assays for glutathione S-transferase and general esterase in individual mosquitoes using an EIA reader. Insect Biochem. 19, 741-751 (1989).
16. A. Lu, and W. Levin: Partial purification of cytochrome P-450 and cytochrome P-448 from rat liver microsomes. Biochem. Biophys. Res. Commun. 46, 1334-1339 (1972).
17. K. J. Johnson and A. E. Ashford: A simultaneous-coupling azo dye method for the quantitative assay of esterase using α-naphthyl acetate as substrate. Histochem. J. 12, 221-234 (1980).
18. max™ and Softmax™. Biotechniques 6, 354-360 (1988).
19. J. K. Stoops, D. J. Morgan, M. T. C. Runnegar, J. de Jersey. E. C. Webb, and B. Zerner: Carboxyesterases (E.C. 3.1.1): kinetic studies on carboxylesterases. Biochemistry 2026-2033 (1969).
20. R. W. Dulac and T. J. Yang: Differential sodium fluoride sensitivity of α-naphthyl acetate esterase in human, bovine, canine and murine monocytes and lymphocytes. Exp. Hematol. 19, 59-62 (1991).
21. D. Abigerges, J. P. Armand. G. G. Chabot, L. Da Costa. E. Fadel. C. Cote C. et al: Irinotecan (CPT-11) high-dose escalation using intensive high-dose loperamide to control diarrhea. J. Natl. Cancer lnst. 86, 446-449 (1994).
22. D. L. Kroetz, O. W. McBride, and F. J. Gonzalez: Glycosylation-dependent activity of baculovirus-expressed human liver carboxylesterases: cDNA cloning and characterization of two highly similar enzyme forms. Biochemistry- 32, 11606-11617 (1993).
23. E. W. Morgan, B. Yan. D. Greenway. D. R. Petersen. and A. Parkinson: Purification and characterization of two rat liver microsomal carboxylesterases (hydrolase A and B) Arch. Biochem. Biophys. 315, 495-512 (1994).
24. A. J. Ketterman, M. R. Bowles, and S. M. Pond: Purification and characterization of two human liver carboxylesterases. Int. J. Biochem. 21, 1303-1312 (1989).
25. A. J. Ketterman: Polymorphisms of human liver carboxylesterases. Biochem. Soc. Trans. 19, 306S (1991).
26. P. D. Senter, H. Marquardt. B. A. Thomas. B. D. Hammock. I. S. Frank. and H. P. Svensson: The role of rat serum carboxylesterase in the activation of paclitaxel and camptothecin prodrugs. Cancer Res. 56, 1471-1474 (1996).
27. H. Ogasawara, K. Nishio, F. Kanzawa. Y. S. Lee. Y. Funayama, T. Ohira, Y. Kuraishi, Y. Isogai, and N. Saijo: Intracellular carboxylesterase activity is a determinant of cellular sensitivity to the antineoplastic agent KW-2189 in cell lines resistant to cisplatin and CPT-11. Jpn. J. Cancer Res. 86, 124-129 (1995).
28. M. Lund-Pero, B. Jeppson, and R. W. Pero: Reduced nonspecific esterase activity in human malignant tumor tissue from liver, colon and breast when compared to peritumoral and normal tissue levels. Anticancer Res. 14, 2747-2754 (1994).
29. M. Hosokawa, T. Endo. M. Fujisawa, S. Hara. N. Iwata, Y. Sato. and T. Satoh: Interindividual variation in carboxylesterase levels in human liver microsomes. Drug Metab. Disp. 23, 1022-1027 (1995).
30. E. W. Morgan, B. Yan, D. Greenway. A. Parkinson: Regulation of two rat liver microsomal carboxylesterase isozymes: species differences, tissue distribution, and the effects of age. sex. and xenobiotic treatment of rats. Arch. Biochem. Biophys. 315, 513-526 (1994).
31. E. Gupta, X. Wang, J. Ramirez, and M. J. Ratain: Modulation of glucuronidation of SN-38. the active metabolite of irinotecan. by valproic acid and phenobarbital. Cancer Chemother. Pharmacol. 39, 440-444 (1997).
32. M. C. Haaz, L. P. Rivory, C. Richet, and J. Robert: Metabolism of CPT-11 (irinotecan) by human hepatic microsomes: Participation of cytochrome P-450 3A (CYP3A) and drug interactions. Proc. Am. Assoc. Cancer Res. 38, Abstract 111 (1997).
33. A. G. Chabot, D. Abigerges, G. Catimel, S. Culine. M. de Forni. J. Extra. M. Mahjoubi, P. Herait, J. Armand, R. Bugat, M. Clavel, and M. Marty: Population pharmacokinetics and pharmacodynamics of irinotecan (CPT-11) and active metabolite SN-38 during phase I trials. Ann. Oncol. 6, 141-151 (1995).
34. A. Tunek and L. A. Svensson: Bambuterol. a carbamate ester prodrug of terbutaline. as inhibitor of cholinesterases in human blood, Drug Metab. Dispos. 16, 759-764 (1988).
35. M-C. Haaz, L. P. Rivory, C. Riche, and J. Robert: The transformation of irinotecan (CPT-11) to its active metabolite SN-38 by human liver microsomes: differential hydrolysis for the lactone and carboxylate forms. Nauyn-Schmiedeberg's Arch. Pharmacol. (in press).
36. 14C-SN-38 to rats. Biol. Pharm. Bull. 18, 1114-1119 (1995).
37. K. Lauritsen, L. S. Laursen, and J. Rask-Madsen: Clinical pharmacokinetics of drugs used in the treatment of gastrointestinal diseases (Part II). Clin. Pharmacokin. 19, 94-125 (1990).
38. 19F NMR spectroscopy for patients receiving chemotherapy with or without methotrexate pretreatment. Cancer Res. 48, 1680-1688 (1988).
39. Y. Sasaki, A. Ohtsu. Y. Shimada, K. Ono K. and N. Saijo: Simultaneous administration of CPT-11 and fluorouracil: alteration of the pharmacokinetics of CPT-11 and SN-38 in patients with advanced colorectal cancer. J. Natl. Cancer Inst. 86, 1096-1098 (1994).
40. L. Saltz. J. Kanowitz, N. Kemeny. D. Kelsen. J. Conti. D. Baiano. L. Schaaf. D. Spriggs, B. Staton. R. Berkery, C. Sieger, M. Eng. A. Dietz. P. Locker: Phase I clinical and pharmacokinetic study of irinotecan. fluorouracil. and leucovorin in patients with advanced solid tumors. J. Clin. Oncol. 14, 2959-2967 (1996).
41. E. Gupta, T. Lestingi, R. Mick, J. Ramirez, E. Vokes, M. Ratain: Metabolic fate of innotecan in humans: Correlation of glucuronidation with diarrhea. Cancer Res. 54, 3723-3725 (1994).