Acetaminophen protein adducts: A review

Clinical Toxicology

Volumn 47, Issue 1, 2009, Pages 2-7

  Bond, G Randall ^a  

^a CINCINNATI CHILDREN'S HOSPITAL MEDICAL CENTER   (United States)

Author keywords

Acetaminophen; Hepatotoxicity; Paracetamol; Poisoning

Indexed keywords

3 (4 CYSTEINYL)ACETAMINOPHEN; ACETAMINOPHEN PROTEIN ADDUCT; PARACETAMOL; PARACETAMOL DERIVATIVE; UNCLASSIFIED DRUG; CYSTEINE; DRUG DERIVATIVE; PARACETAMOL CYSTEINE;

BIOASSAY; CAUSAL ATTRIBUTION; DIAGNOSTIC VALUE; HUMAN; LIVER INJURY; LIVER TOXICITY; NONHUMAN; QUANTITATIVE ASSAY; REVIEW; ANIMAL; DRUG EFFECT; LIVER; METABOLISM; PROTEIN BINDING; RADIOASSAY;

ANIMALIA;

ACETAMINOPHEN; ANIMALS; CYSTEINE; HUMANS; LIVER; PROTEIN BINDING; RADIOLIGAND ASSAY;

EID: 59649097350     PISSN: 15563650     EISSN: 15569519     Source Type: Journal    
DOI: 10.1080/15563650801941831     Document Type: Review

References (21)

1. Mitchell JR, Jollow DJ, Potter WZ, Davis DC, Gillette JR, Brodie BB. Acetaminophen-induced hepatic necrosis. I. Role of drug metabolism. J Pharmacol Exp Therap 1973; 187:185-194.
2. Jollow D J, Mitchell JR, Potter WZ, Davis DC, Gillette JR, Brodie BB. Acetaminophen-induced hepatic necrosis. II. Role of covalent binding in vivo. J Pharmacol Exp Ther 1973; 187:195-202.
3. Hinson JA, Pike SL, Pumford NR, Mayeux PR. Nitrotyrosine-protein adducts in hepatic centrilobular areas following toxic doses of acetaminophen in mice. Chem Res Toxicol 1998; 11:604-607.
4. James LP, Mayeux PR, Hinson JA. Acetaminophen-induced hepatotoxicity. Drug Metab Dispos 2003; 31:1499-1506.
5. Pumford NR, Hinson JA, Potter DW, Rowland KL, Benson RW, Roberts DW. Immunochemical quantitation of 3-(cystein-S-yl)acetaminophen adducts in serum and liver proteins of acetaminophen-treated mice. J Pharmacol Exp Ther 1989; 248:190-196.
6. Bartolone JB, Beierschmitt WP, Birge RB, Hart SG, Wyand S, Cohen SD, Khairallah EA. Selective acetaminophen metabolite binding to hepatic and extrahepatic proteins: an in vivo and in vitro analysis. Toxicol Appl Pharmacol 1989; 99:240-249.
7. Muldrew KL, James LP, Coop L, McCullough SS, Hendrickson HP, Hinson JA, et al. Determination of acetaminophen-protein adducts in mouse liver and serum and human serum after hepatotoxic doses of acetaminophen using high-performance liquid chromatography with electrochemical detection. Drug Metab Dispos 2002; 30:446-451.
8. Davern TJ, 2nd, James LP, Hinson JA, Polson J, Larson AM, Fontana RJ, et al. Measurement of serum acetaminophen-protein adducts in patients with acute liver failure. Gastroenterology 2006; 130:687-694.
9. James LP, Alonso EM, Hynan LS, Hinson JA, Davern TJ, Lee WM, et al. Detection of acetaminophen protein adducts in children with acute liver failure of indeterminate cause. Pediatrics 2006; 118:e676-e681.
10. Rhyee SH, Green JL, James L, Heard K, Dart RC. Acetaminophen protein adducts in therapeutic acetaminophen dosing. Clinical Toxicol 2007; 45:605.
11. Rhyee SH, Green JL, James L, Heard K, Dart RC. Acetaminophen protein adducts in alcoholic patients receiving acetaminophen 4 g/day for 5 days. Hepatology 2007; 46 (Supplement 1):812A.
12. James LP, Simpson P, Rahman S, Russo M, Watkins PB. Detection of acetaminophen protein adducts in serum during therapeutic dosing of acetaminophen in healthy volunteers. Hepatology 2007; 46 (suppl 1):812A.
13. Pumford NR, Halmes NC, Hinson JA. Covalent binding of xenobiotics to specific proteins in the liver. Drug Metab Rev 1997; 29:39-57.
14. Jaeschke H, Bajt ML. Intracellular signaling mechanisms of acetaminophen-induced liver cell death. Toxicol Sci 2006; 89:31-41.
15. James LP, McCullough SS, Lamps LW, Hinson JA. Effect of N-acetylcysteine on acetaminophen toxicity in mice: relationship to reactive nitrogen and cytokine formation. Toxicol Sci 2003; 75:458-467.
16. Michael SL, Pumford NR, Mayeux PR, Niesman MR, Hinson JA. Pretreatment of mice with macrophage inactivators decreases acetaminophen hepatotoxicity and the formation of reactive oxygen and nitrogen species. Hepatology 1999; 30:186-195.
17. Bourdi M, Masubuchi Y, Reilly TP, Amouzadeh HR, Martin JL, George JW, Shah AG, Pohl LR. Protection against acetaminophen-induced liver injury and lethality by interleukin 10: role of inducible nitric oxide synthase. Hepatology 2002; 35:289-298.
18. Hinson JA, Roberts DW, Benson RW, Dalhof K, Loft S, Poulsen HE. Mechanism of paracetamol toxicity. Lancet 1990; 335:732.
19. Webster PA, Roberts DW, Benson RW, Kearns GL. Acetaminophen toxicity in children: diagnostic confirmation using a specific antigenic biomarker. J Clin Pharmacol 1996; 36:397-402.
20. James LP, Farrar HC, Sullivan JE, Givens TG, Kearns GL, Wasserman GS, et al. Measurement of acetaminophen-protein adducts in children and adolescents with acetaminophen overdoses. J Clin Pharmacol 2001; 41:846-851.
21. Polson J, James LP, Davern TJ, Hynan L, Rossario L, Larson AM, Pezzia C, Lee WM. Acetaminophen as a co-factor in acute liver failure due to viral hepatitis determined by measurement of acetaminophen protein adducts (abstract). Gastroenterology 2006; 130(suppl 2):A-772.