Transiently altered acetaminophen metabolism after liver transplantation

Clin Pharmacol Ther. 2003 Jun;73(6):545-53. doi: 10.1016/S0009-9236(03)00062-6.

Abstract

Background and objectives: Acetaminophen (INN, paracetamol) is metabolized to N-acetyl-p-benzoquinone imine (NAPQI), a hepatotoxic metabolite, predominantly by cytochrome P450 (CYP) 2E1. Alterations in drug metabolism occur after organ transplantation. This study was designed to characterize acetaminophen disposition during the first 6 months after liver transplantation.

Methods: Thirteen liver transplant patients received an oral dose of acetaminophen (500 mg) on days 2, 10, 90, and 180 after transplantation. Serial blood samples were collected for 8 hours, and urine was collected for 24 hours. Liver biopsy specimens were obtained from the donor liver during transplantation (day 0) and on days 10, 90, and 180 after transplantation.

Results: There were significant time-dependent changes in acetaminophen metabolism after liver transplantation. When day 2 and day 10 were compared with day 180, the respective mean urinary recovery was 137% and 81% higher for thioether conjugates derived from NAPQI (P =.0002 and P =.01, respectively); 31% and 22% lower for acetaminophen sulfate (P =.0006 and P =.008, respectively); and 22% and 27% lower for acetaminophen glucuronide (P =.05 and P =.004, respectively). Metabolite formation clearances changed in concordance with the fractional urinary recovery. It was surprising that hepatic CYP2E1 content on day 10 after transplantation was only 20% higher, on average, than that found on day 180 (not significant). In contrast, hepatic CYP3A4 content was 984% higher, on average, when tissue from days 10 and 180 was compared after transplantation (P =.007).

Conclusions: Increased recovery of acetaminophen thioether conjugates during the first 10 days after liver transplantation was a result of impaired glucuronidation and sulfation and enhanced NAPQI formation.

Publication types

  • Clinical Trial
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Acetaminophen / pharmacokinetics*
  • Adult
  • Analgesics, Non-Narcotic / pharmacokinetics*
  • Area Under Curve
  • Benzoquinones / metabolism
  • Biopsy, Needle
  • Biotransformation
  • Blotting, Western
  • Cytochrome P-450 CYP2E1 / biosynthesis
  • Cytochrome P-450 CYP2E1 / genetics
  • Cytochrome P-450 CYP3A
  • Cytochrome P-450 Enzyme System / metabolism*
  • Female
  • Half-Life
  • Humans
  • Imines / metabolism
  • Liver / enzymology
  • Liver Transplantation / physiology*
  • Male
  • Middle Aged

Substances

  • Analgesics, Non-Narcotic
  • Benzoquinones
  • Imines
  • Acetaminophen
  • Cytochrome P-450 Enzyme System
  • Cytochrome P-450 CYP2E1
  • CYP3A protein, human
  • Cytochrome P-450 CYP3A
  • CYP3A4 protein, human
  • N-acetyl-4-benzoquinoneimine