Differential rates of glucuronidation for 7-ethyl-10-hydroxycamptothecin (SN-38) lactone and carboxylate in human and rat microsomes and recombinant UDP-glucuronosyltransferase isoforms

Drug Metabolism and Disposition

Volumn 33, Issue 7, 2005, Pages 977-983

  Tallman, Melanie N ^a   Ritter, Joseph K ^b   Smith, Philip C ^a  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

^b VIRGINIA COMMONWEALTH UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

7 ETHYL 10 HYDROXYCAMPTOTHECIN; CARBOXYLIC ACID; GLUCURONOSYLTRANSFERASE; IRINOTECAN; ISOPROTEIN; LACTONE DERIVATIVE;

ANIMAL TISSUE; ARTICLE; CATALYSIS; CONJUGATION; EXPERIMENTATION; GLUCURONIDATION; HUMAN; HUMAN CELL; INCUBATION TIME; INTESTINE; KINETICS; MALE; MICROSOME; NONHUMAN; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN TRANSPORT; RAT;

ANIMALS; CAMPTOTHECIN; CARBOXYLIC ACIDS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GLUCURONIDES; GLUCURONOSYLTRANSFERASE; HUMANS; ISOENZYMES; LACTONES; MICROSOMES, LIVER; RATS; RECOMBINANT PROTEINS;

EID: 22344455999     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: 10.1124/dmd.104.003491     Document Type: Article

References (28)

1. Akimoto K, Kawai A, and Ohya K (1994) Kinetic studies of the hydrolysis and lactonization of Camptothecin and its derivatives, CPT-11 and SN-38, in aqueous solution. Chem Pharm Bull 42:2135-2138.
2. Burke TG and Mi Z (1993) Ethyl substitution at the 7 position extends the half-life of 10-hydroxycamptothecin in the presence of human serum albumin. J Med Chem 36:2580-2582.
3. Chourpa I, Millot JM, Sockalingum GD, Riou JF, and Manfait M (1998) Kinetics of lactone hydrolysis in antitumor drugs of camptothecin series as studied by fluorescence spectroscopy. Biochim Biophys Acta 1379:353-366.
4. Chu XY, Kato Y, Niinuma K, Sudo KI, Hakusui H, and Sugiyama Y (1997) Multispecific organic anion transporter is responsible for the biliary excretion of the camptothecin derivative irinotecan and its metabolites in rats. J Pharmacol Exp Ther 281:304-314.
5. Ciotti M, Basu N, Brangi M, and Owens IS (1999) Glucuronidation of 7-ethyl-10-hydroxycamptothecin (SN-38) by the human UDP-glucuronosyltransferases encoded at the UGT1 locus. Biochem Biophys Res Commun 260:199-202.
6. Gagne JF, Montminy V, Belanger P, Journault K, Gaucher G, and Guillemette C (2002) Common human UGT1A polymorphisms and the altered metabolism of irinotecan active metabolite 7-ethyl-10-hydroxycamptothecin (SN-38). Mol Pharmacol 62:608-617.
7. Gupta E, Lestingi TM, Mick R, Ramirez J, Vokes EE, and Ratain MJ (1994) Metabolic fate of irinotecan in humans: correlation of glucuronidation with diarrhea. Cancer Res 54:3723-3725.
8. Haaz MC, Rivory L, Jantet S, Ratanasavanh D, and Robert J (1997a) Glucuronidation of SN-38, the active metabolite of irinotecan, by human hepatic microsomes. Pharmacol Toxicol 80: 91-96.
9. Haaz MC, Rivory LP, Riche C, and Robert J (1997b) 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.
10. Hanioka N, Jinno H, Nishimura T, Ando M, Ozawa S, and Sawada J (2001a) High-performance liquid chromatographic assay for glucuronidation activity of 7-ethyl-10-hydroxycamptothecin (SN-38), the active metabolite of irinotecan (CPT-11), in human liver microsomes. Biomed Chromatogr 15:328-333.
11. Hanioka N, Ozawa S, Jinno H, Ando M, Saito Y, and Sawada J (2001b) Human liver UDP-glucuronosyltransferase isoforms involved in the glucuronidation of 7-ethyl-10-hydroxycamptothecin. Xenobiotica 31:687-699.
12. Hertzberg RP, Busby RW, Caranfa MJ, Holden KG, Johnson RK, Hecht SM, and Kingsbury WD (1990) Irreversible trapping of the DNA-topoisomerase I covalent complex. Affinity labeling of the camptothecin binding site. J Biol Chem 265:19287-19295.
13. Kaneda N, Hosokawa Y, Yokokura T, and Awazu S (1997) Plasma pharmacokinetics of 7-ethyl-10-hydroxycamptothecin (SN-38) after intravenous administration of SN-38 and irinotecan (CPT-11) to rats. Biol Pharm Bull 20:992-996.
14. Kawato Y, Aonuma M, Hirota Y, Kuga H, and Sato K (1991) Intracellular roles of SN-38, a metabolite of the camptothecin derivative CPT-11, in the antitumor effect of CPT-11. Cancer Res 51:4187-4191.
15. Kessler FK, Kessler MR, Auyeung DJ, and Ritter JK (2002) Glucuronidation of acetaminophen catalyzed by multiple rat phenol UDP-glucuronosyltransferases. Drug Metab Dispos 30:324-330.
16. Khanna R, Morton CL, Danks MK, and Potter PM (2000) Proficient metabolism of irinotecan by a human intestinal carboxylesterase. Cancer Res 60:4725-4728.
17. Mathijssen RH, van Alphen RJ, Verweij J, Loos WJ, Nooter K, Stoter G, and Sparreboom A (2001) Clinical pharmacokinetics and metabolism of irinotecan (CPT-11). Clin Cancer Res 7:2182-2194.
18. Meech R and Mackenzie PI (1997) Structure and function of uridine diphosphate glucuronosyltransferases. Clin Exp Pharmacol Physiol 24:907-915.
19. Rajkumar SV and Adjei AA (1998) A review of the pharmacology and clinical activity of new chemotherapeutic agents in lung cancer. Cancer Treat Rev 24:35-53.
20. Rivory LP, Chatelut E, Canal P, Mathieu-Boue A, and Robert J (1994) Kinetics of the in vivo interconversion of the carboxylate and lactone forms of irinotecan (CPT-11) and of its metabolite SN-38 in patients. Cancer Res 54:6330-6333.
21. Rothenberg ML (2001) Irinotecan (CPT-11): recent developments and future directions-colorectal cancer and beyond. Oncologist 6:66-80.
22. Sasaki Y, Yoshida Y, Sudoh K, Hakusui H, Fujii H, Ohtsu T, Wakita H, Igarashi T, and Itoh K (1995) Pharmacological correlation between total drug concentration and lactones of CPT-11 and SN-38 in patients treated with CPT-11. Jpn J Cancer Res 86:111-116.
23. Sparreboom A, de Bruijn P, de Jonge MJ, Loos WJ, Stoter G, Verweij J, and Nooter K (1998) Liquid chromatographic determination of irinotecan and three major metabolites in human plasma, urine and feces. J Chromatogr B Biomed Sci Appl 712:225-235.
24. Strassburg CP, Manns MP, and Tukey RH (1998) Expression of the UDP-glucuronosyltransferase 1A locus in human colon. Identification and characterization of the novel extrahepatic UGT1A8. J Biol Chem 273:8719-8726.
25. Tukey RH, Strassburg CP, and Mackenzie PI (2002) Pharmacogenomics of human UDP-glucuronosyltransferases and irinotecan toxicity. Mol Pharmacol 62:446-450.
26. Xie R, Mathijssen RH, Sparreboom A, Verweij J, and Karlsson MO (2002) Clinical pharmacokinetics of irinotecan and its metabolites: a population analysis. J Clin Oncol 20:3293-3301.
27. Yokota H, Yuasa A, and Sato R (1992) Topological disposition of UDP-glucuronyltransferase in rat liver microsomes. J Biochem (Tokyo) 112:192-196.
28. Zhang JA, Xuan T, Parmar M, Ma L, Ugwa S, Ali S, and Ahmad I (2004) Development and characterization of a novel liposome-based formulation of SN-38. Int J Pharm 270:93-107.