The in vitro metabolism of irinotecan (CPT-11) by carboxylesterase and beta-glucuronidase in human colorectal tumours

Br J Clin Pharmacol. 2006 Jul;62(1):122-9. doi: 10.1111/j.1365-2125.2005.02477.x.

Abstract

Aims: Irinotecan (CPT-11) is a prodrug that is used to treat metastatic colorectal cancer. It is activated to the topoisomerase poison SN-38 by carboxylesterases. SN-38 is metabolized to its inactive glucuronide, SN-38 glucuronide. The aim of this study was to determine, the reactivation of SN-38 from SN-38 glucuronide by beta-glucuronidase may represent a significant pathway of SN-38 formation.

Methods: The production of SN-38 from irinotecan and SN-38 glucuronide (2.4, 9.6 and 19.2 microm) was measured in homogenates of human colorectal tumour, and matched normal colon mucosa from 21 patients).

Results: The rate of conversion of irinotecan (9.6 microm) was lower in tumour tissue than matched normal colon mucosa samples (0.30+/-0.14 pmol min-1 mg-1 protein and 0.77+/-0.59 pmol min-1 mg-1 protein, respectively; P<0.005). In contrast, no significant difference was observed in beta-glucuronidase activity between tumour and matched normal colon samples (4.56+/-6.9 pmol min-1 mg-1 protein and 3.62+/-2.95 pmol min-1 mg-1 protein, respectively, using 9.6 microm SN-38 glucuronide; P>0.05). beta-Glucuronidase activity in tumour correlated to that observed in matched normal tissue (r2>0.23, P<0.05), whereas this was not the case for carboxylesterase activity. At equal concentrations of irinotecan and SN-38 glucuronide, the rate of beta-glucuronidase-mediated SN-38 production was higher than that formed from irinotecan in both tumour and normal tissue (P<0.05). However, at concentrations that reflect the relative plasma concentrations observed in patients, the rate of SN-38 production via these two pathways was comparable.

Conclusions: Tumour beta-glucuronidase may play a significant role in the exposure of tumours to SN-38 in vivo.

MeSH terms

  • Antineoplastic Agents, Phytogenic / metabolism*
  • Antineoplastic Agents, Phytogenic / therapeutic use
  • Camptothecin / analogs & derivatives*
  • Camptothecin / metabolism
  • Camptothecin / therapeutic use
  • Carboxylesterase / metabolism*
  • Colorectal Neoplasms / drug therapy
  • Colorectal Neoplasms / enzymology*
  • Glucuronidase / metabolism*
  • Humans
  • Hydroxyquinolines / pharmacology
  • Irinotecan
  • Nitrophenols / pharmacology
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents, Phytogenic
  • Hydroxyquinolines
  • Nitrophenols
  • 8-hydroxyquinoline glucuronide
  • Irinotecan
  • Carboxylesterase
  • Glucuronidase
  • Camptothecin
  • 4-nitrophenol