Role of 3,4-dichlorophenyl methyl sulfone, a metabolite of o-dichlorobenzene, in the changes in hepatic microsomal drug-metabolizing enzymes caused by o-dichlorobenzene administration in rats

Toxicol Appl Pharmacol. 1997 Aug;145(2):277-84. doi: 10.1006/taap.1997.8191.

Abstract

2,3- and 3,4-Dichlorophenyl methyl sulfoxides and 2,3- and 3,4-dichlorophenyl methyl sulfones (2,3- and 3,4-DCPSO2Mes) were detected in the urine of rats administered o-dichlorobenzene (o-DCB). After administration of o-DCB to rats, swift decreases were observed in the concentrations of o-DCB in blood, liver, and kidneys, whereas 3,4-DCPSO2Me appeared in blood, liver, kidneys, and adipose tissue. The concentrations of 3,4-DCPSO2Me in the blood and three tissues reached maxima at 24 hr. Both aminopyrine N-demethylase and aniline hydroxylase activities and cytochrome P450 content of hepatic microsomes decreased 24 hr after administration of o-DCB. In contrast, 3,4-DCPSO2Me increased the activities of these enzymes and cytochrome P450 and b5 contents in rat liver microsomes. In both antibiotic-pretreated and bile duct-cannulated rats dosed with o-DCB, the concentrations of 2,3- and 3,4-DCPSO2Mes in blood, liver, kidneys, and adipose tissue were dramatically reduced. These findings suggest that the process of formation of methylsulfonyl metabolites of o-DCB involves biliary secretion of DCPSO2Mes and/or their precursors which will be subjected to metabolism by intestinal microflora. In antibiotic-pretreated rats, the inhibitory effects of o-DCB administration on the activities of aminopyrine- and aniline-metabolizing enzymes and the contents of cytochromes P450 and b5 in hepatic microsomes were greater than those observed in the intact rats. In bile duct-cannulated rats, the decrease in aminopyrine N-demethylase activity after administration of o-DCB was greater than that observed in the intact rats. These findings suggest that the apparent inhibition of drug-metabolizing enzymes by o-DCB is the result of simultaneous contrary effects, namely, the inductive effect of 3,4-DCPSO2Me and the stronger inhibitory effect of an unknown factor(s) on drug-metabolizing enzymes.

MeSH terms

  • Aminopyrine N-Demethylase / antagonists & inhibitors
  • Aminopyrine N-Demethylase / metabolism
  • Animals
  • Anti-Bacterial Agents / metabolism
  • Anti-Bacterial Agents / pharmacology
  • Bile Ducts / physiology
  • Catheterization
  • Chlorobenzenes / metabolism*
  • Chlorobenzenes / toxicity*
  • Chlorophenols / pharmacology*
  • Cytochrome P-450 Enzyme Inhibitors
  • Cytochrome P-450 Enzyme System / metabolism
  • Enzyme Induction / drug effects
  • Injections, Intraperitoneal
  • Insecticides / metabolism
  • Insecticides / toxicity*
  • Male
  • Mesylates / pharmacology*
  • Microsomes, Liver / drug effects*
  • Microsomes, Liver / enzymology*
  • Microsomes, Liver / metabolism
  • Rats
  • Rats, Wistar
  • Tissue Distribution / drug effects

Substances

  • 3,4-dichlorophenyl methyl sulfone
  • Anti-Bacterial Agents
  • Chlorobenzenes
  • Chlorophenols
  • Cytochrome P-450 Enzyme Inhibitors
  • Insecticides
  • Mesylates
  • 2-dichlorobenzene
  • Cytochrome P-450 Enzyme System
  • Aminopyrine N-Demethylase