Conversion of irinotecan (CPT-11) to its active metabolite, 7-ethyl-10-hydroxycamptothecin (SN-38) by human liver carboxylesterase

Biochemical Pharmacology

Volumn 52, Issue 7, 1996, Pages 1103-1111

  Rivory, Laurent P ^a   Bowles, Mark R ^a   Robert, Jacques ^b   Pond, Susan M ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

^b INSTITUT BERGONIÉ   (France)

Author keywords

camptothecin; carboxylesterase (EC 3.1.1.1); enzyme kinetics; irinotecan; loperamide

Indexed keywords

4 NITROPHENYL ACETATE; 7 ETHYL 10 HYDROXYCAMPTOTHECIN; ANTIDIARRHEAL AGENT; CARBOXYLESTERASE; DNA TOPOISOMERASE INHIBITOR; DRUG METABOLITE; IRINOTECAN; LIVER ENZYME; LOPERAMIDE; PARAOXON; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; CATALYSIS; CONTROLLED STUDY; DEACYLATION; DRUG METABOLISM; ENZYME ACTIVE SITE; ENZYME KINETICS; ENZYME PURIFICATION; ENZYME SUBSTRATE; HUMAN; HYDROLYSIS; MICHAELIS MENTEN KINETICS; PRIORITY JOURNAL; REACTION ANALYSIS; STEADY STATE;

EID: 0030580064     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/0006-2952(96)00457-1     Document Type: Article

References (15)

1. 1. Sawada S, Okajima S, Aiyama R, Nokata K-I, Furuta T, Yokokura T, Sugino E, Yamaguchi K and Miyasaka T, Synthesis and antitumor activity of 20(S)-camptothecin derivatives: Carbamate-linked, water-soluble derivatives of 7-ethyl-10-hydroxycamptothecin. Chem Pharm Bull (Tokyo) 39: 1446-1454, 1991.
2. 2. Slichenmyer WJ, Rowinsky EK, Donehower RC and Kaufmann SH, The current status of camptothecin analogues as antitumor agents. J Natl Cancer Inst 85: 271-291, 1993.
3. 3. Rivory LP and Robert J, Molecular, cellular, and clinical aspects of the pharmacology of 20(S)camptothecin and its derivatives. Pharmacol Ther 68: 269-296, 1995.
4. 4. Rowinsky EK, Grochow LB, Ettinger DS, Sartorius SE, Lubejko BG, Chen T-L, Rock MK and Donehower RC, Phase I and pharmacological study of the novel topoisomerase I inhibitor 7-ethyl-10-[-4-(1-piperidino)-1-piperidino]-carbonyloxy camptothecin (CPT-11) administered as a ninety-minute infusion every 3 weeks. Cancer Res 54: 427-436, 1994.
5. 5. Satoh T, Hosokawa M, Atsumi R, Susuki W, Hakushi H and Nagai E, Metabolic activation of CPT-11, 7-ethyl-10-[4-(1-piperidino)-1-piperidino]carbonyloxy camptothecin, a novel antitumor agent, by carboxylesterase. Biol Pharm Bull 17: 662-664, 1994.
6. 6. Tsuji T, Kaneda N, Kado K, Yokokura T, Yoshimoto T and Tsuru D, CPT-11 converting enzyme from rat serum: Purification and some properties. J Pharmacobiodyn 14: 341-349, 1991.
7. 7. Ketterman AJ, Bowles MR and Pond SM, Purification and characterization of two human liver carboxylesterases. Int J Biochem 21: 1303-1312, 1989.
8. 8. Morgan DJ, Dunstone JR, Stoops JK, Webb EC and Zerner B, Carboxylesterases (EC 3.1.1). The molecular weight and equivalent weight of pig liver carboxylesterase. Biochemistry 8: 2006-2013, 1969.
9. 9. Rivory LP 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 B Biomed Appl 661: 133-141, 1994.
10. 10. Ouellet L and Stewart JA, Theory of the transient phase in an enzyme system involving two enzyme-substrate complexes. The case of the formation of products from the first complex. Can J Chem 37: 737-743, 1959.
11. 11. Dixon M and Webb EC, Enzymes, 3rd Edn, p. 337. Academic Press, New York, 1979.
12. 12. Junge W, Heymann E, Krisch K and Hollandt H, Human liver carboxylesterase. Purification and molecular properties. Arch Biochem Biophys 165: 749-763, 1974.
13. 13. Stoops JK, Morgan DJ, Runnegar MTC, de Jersey J, Webb EC and Zerner B, Carboxylesterases (EC 3.1.1). Kinetic studies on carboxylesterases. Biochemistry 8: 2026-2033, 1969.
14. 14. Fassberg J and Stella VJ, A kinetic and mechanistic study of the hydrolysis of camptothecin and some analogues. J Pharm Sci 81: 676-684, 1992.
15. 15. Abigerges D, Armand JP, Chabot GG, Da Costa L, Fadel E, Cote C, Herait P and Gandia D, Irinotecan (CPT-11) high-dose escalation using intensive high-dose loperamide to control diarrhea. J Natl Cancer Inst 86: 446-449, 1994.