Reactive metabolites of phenacetin and acetaminophen: a review.

PubWeight™: 0.81‹?›

🔗 View Article (PMC 1569121)

Published in Environ Health Perspect on March 01, 1983

Authors

J A Hinson

Articles cited by this

Acetaminophen-induced hepatic necrosis. IV. Protective role of glutathione. J Pharmacol Exp Ther (1973) 5.23

Acute liver necrosis following overdose of paracetamol. Br Med J (1966) 4.75

Acetaminophen-induced hepatic necrosis. I. Role of drug metabolism. J Pharmacol Exp Ther (1973) 4.40

Acetaminophen-induced hepatic necrosis. II. Role of covalent binding in vivo. J Pharmacol Exp Ther (1973) 3.89

Liver necrosis from paracetamol. Br J Pharmacol Chemother (1966) 3.77

Carcinoma of the renal pelvis in renal papillary necrosis. Acta Chir Scand (1965) 1.92

Acetaminophen-induced hepatic necrosis. 3. Cytochrome P-450-mediated covalent binding in vitro. J Pharmacol Exp Ther (1973) 1.90

Acetaminophen-induced hepatic necrosis. VI. Metabolic disposition of toxic and nontoxic doses of acetaminophen. Pharmacology (1974) 1.70

N-hydroxy-2-acetylaminofluorene sulfotransferase: its probable role in carcinogenesis and in protein-(methion-S-yl) binding in rat liver. Cancer Res (1970) 1.26

Malignancies of the urinary tract and their relation to analgesic abuse. Kidney Int (1978) 1.14

Acetaminophen-induced hepatotoxicity. Life Sci (1981) 1.09

Generation of reactive metabolites of N-hydroxy-phenacetin by glucoronidation and sulfation. Biochem Pharmacol (1977) 1.02

N-Hydroxyacetaminophen: a microsomal metabolite of N-hydroxyphenacetin but apparently not of acetaminophen. Life Sci (1979) 0.96

The formation of arylating and alkylating metabolites of phenacetin in hamsters and hamster liver microsomes. Mol Pharmacol (1981) 0.94

Tumors of Sprague-Dawley rats induced by long-term feeding of phenacetin. Gan (1979) 0.86

Studies on the microsomal formation of arylating metabolites of acetaminophen and phenacetin. Mol Pharmacol (1977) 0.86

Renal disease due to analgesics. I. Recognition of the problem of analgesic nephropathy. Can Med Assoc J (1972) 0.85

Conversion of the N-Q-glucuronide and N-O-sulfate conjugates of N-hydroxyphenacetin to reactive intermediates. Biochem Pharmacol (1978) 0.84

Analgesic abuse and renal disease. Annu Rev Med (1975) 0.83

N-hydroxylation of p-acetophenetidide as a factor in nephrotoxicity. J Med Chem (1973) 0.81

N-Hydroxylation of phenacetin by hamster liver microsomes. Drug Metab Dispos (1977) 0.80

Metabolism of acetanilides and anisoles with rat liver microsomes. Biochem Pharmacol (1970) 0.79

Liver and kidney damage induced by N-hydroxyparacetamol. Xenobiotica (1978) 0.78

Kinetic evidence for multiple chemically reactive intermediates in the breakdown of phenacetin N-O-glucuronide. Pharmacology (1979) 0.78

Metabolism of [p-18O]-phenacetin: the mechanism of activation of phenacetin to reactive metabolites in hamsters. Mol Pharmacol (1979) 0.78

3-Hydroxyacetaminophen: a microsomal metabolite of acetaminophen. Evidence against an epoxide as the reactive metabolite of acetaminophen. Drug Metab Dispos (1981) 0.77

N-hydroxylation of p-chloroacetanilde in hamsters. Biochem Pharmacol (1976) 0.77

Synthesis of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen, and its phenolic sulfate conjugate. J Med Chem (1978) 0.77

Articles by these authors

Vascular and hepatocellular peroxynitrite formation during acetaminophen toxicity: role of mitochondrial oxidant stress. Toxicol Sci (2001) 2.00

Pretreatment of mice with macrophage inactivators decreases acetaminophen hepatotoxicity and the formation of reactive oxygen and nitrogen species. Hepatology (1999) 1.68

Selective protein covalent binding and target organ toxicity. Toxicol Appl Pharmacol (1997) 1.66

Immunohistochemical localization and quantification of the 3-(cystein-S-yl)-acetaminophen protein adduct in acetaminophen hepatotoxicity. Am J Pathol (1991) 1.57

Acetaminophen-associated hepatic injury: evaluation of acetaminophen protein adducts in children and adolescents with acetaminophen overdose. Clin Pharmacol Ther (2008) 1.48

Immunochemical quantitation of 3-(cystein-S-yl)acetaminophen adducts in serum and liver proteins of acetaminophen-treated mice. J Pharmacol Exp Ther (1989) 1.28

The spontaneous and enzymatic reaction of N-acetyl-p-benzoquinonimine with glutathione: a stopped-flow kinetic study. Arch Biochem Biophys (1988) 1.17

Acetaminophen-induced hepatotoxicity in mice lacking inducible nitric oxide synthase activity. Nitric Oxide (2001) 1.16

A sensitive immunochemical assay for acetaminophen-protein adducts. J Pharmacol Exp Ther (1987) 1.13

Acetaminophen-induced hepatic glycogen depletion and hyperglycemia in mice. Biochem Pharmacol (1983) 1.12

Acetaminophen-induced hepatotoxicity. Life Sci (1981) 1.09

Immunochemical detection of oxidized proteins. Chem Res Toxicol (1993) 1.09

Stereoselective formation of bromobenzene glutathione conjugates. Chem Biol Interact (1982) 1.08

Covalent binding of xenobiotics to specific proteins in the liver. Drug Metab Rev (1997) 1.03

Generation of reactive metabolites of N-hydroxy-phenacetin by glucoronidation and sulfation. Biochem Pharmacol (1977) 1.02

Measurement of acetaminophen-protein adducts in children and adolescents with acetaminophen overdoses. . J Clin Pharmacol (2001) 0.98

Immunoblot analysis of protein containing 3-(cystein-S-yl)acetaminophen adducts in serum and subcellular liver fractions from acetaminophen-treated mice. Toxicol Appl Pharmacol (1990) 0.98

Immunochemical quantitation of 3-(cystein-S-yl)acetaminophen protein adducts in subcellular liver fractions following a hepatotoxic dose of acetaminophen. Biochem Pharmacol (1990) 0.98

Mechanism of paracetamol toxicity. Lancet (1990) 0.97

N-Hydroxyacetaminophen: a microsomal metabolite of N-hydroxyphenacetin but apparently not of acetaminophen. Life Sci (1979) 0.96

Oxidant stress in rat liver after lipopolysaccharide administration: effect of inducible nitric-oxide synthase inhibition. J Pharmacol Exp Ther (2000) 0.96

The formation of arylating and alkylating metabolites of phenacetin in hamsters and hamster liver microsomes. Mol Pharmacol (1981) 0.94

Covalent binding of acetaminophen to N-10-formyltetrahydrofolate dehydrogenase in mice. J Pharmacol Exp Ther (1997) 0.93

Deferoxamine delays the development of the hepatotoxicity of acetaminophen in mice. Toxicol Lett (1999) 0.93

Role of metabolites in propanil-induced hemolytic anemia. Toxicol Appl Pharmacol (1991) 0.91

Evaluation of occult acetaminophen hepatotoxicity in hospitalized children receiving acetaminophen. Pediatric Pharmacology Research Unit Network. Clin Pediatr (Phila) (2001) 0.91

Reactions of N-acetyl-p-benzoquinone imine with reduced glutathione, acetaminophen, and NADPH. Mol Pharmacol (1986) 0.90

Contribution of 3,4-dichlorophenylhydroxylamine in propanil-induced hemolytic anemia. Adv Exp Med Biol (1991) 0.89

Metabolism of the arylamide herbicide propanil. I. Microsomal metabolism and in vitro methemoglobinemia. Toxicol Appl Pharmacol (1990) 0.89

3-(glutathion-S-yl)acetaminophen: a biliary metabolite of acetaminophen. Drug Metab Dispos (1982) 0.89

Hepatic necrosis caused by furosemide. Nature (1974) 0.89

Acetaminophen-induced hepatotoxicity. Analysis of total covalent binding vs. specific binding to cysteine. Drug Metab Dispos (1996) 0.88

A metabolite of acetaminophen covalently binds to the 56 kDa selenium binding protein. Biochem Biophys Res Commun (1992) 0.88

Bromobenzene and p-bromophenol toxicity and covalent binding in vivo. Life Sci (1982) 0.87

The 1- and 2-electron oxidation of acetaminophen catalyzed by prostaglandin H synthase. J Biol Chem (1987) 0.87

Reaction of mutagenic phenacetin metabolites with glutathione and DNA. Possible implications for toxicity. Mol Pharmacol (1984) 0.87

Studies on the microsomal formation of arylating metabolites of acetaminophen and phenacetin. Mol Pharmacol (1977) 0.86

Comparison of covalent binding of acetaminophen and the regioisomer 3'-hydroxyacetanilide to mouse liver protein. Toxicol Lett (1997) 0.86

Mechanism of acetaminophen-induced hepatotoxicity: covalent binding versus oxidative stress. Chem Res Toxicol (1996) 0.86

Elevation of serum interleukin 8 levels in acetaminophen overdose in children and adolescents. Clin Pharmacol Ther (2001) 0.84

Conversion of the N-Q-glucuronide and N-O-sulfate conjugates of N-hydroxyphenacetin to reactive intermediates. Biochem Pharmacol (1978) 0.84

Mechanisms of acetaminophen oxidation to N-acetyl-P-benzoquinone imine by horseradish peroxidase and cytochrome P-450. J Biol Chem (1987) 0.83

2,6-Dimethylaniline--hemoglobin adducts from lidocaine in humans. Carcinogenesis (1994) 0.83

The formation of diglutathionyl dithiocarbonate as a metabolite of chloroform, bromotrichloromethane, and carbon tetrachloride. Drug Metab Dispos (1981) 0.82

Propanil-induced methemoglobinemia and hemoglobin binding in the rat. Toxicol Appl Pharmacol (1990) 0.82

Metabolism of the arylamide herbicide propanil. II. Effects of propanil and its derivatives on hepatic microsomal drug-metabolizing enzymes in the rat. Toxicol Appl Pharmacol (1990) 0.82

Formation of chemically reactive metabolites of phenacetin and acetaminophen. Adv Exp Med Biol (1981) 0.82

Epitope characterization of acetaminophen bound to protein and nonprotein sulfhydryl groups by an enzyme-linked immunosorbent assay. J Pharmacol Exp Ther (1989) 0.81

Glutamate dehydrogenase covalently binds to a reactive metabolite of acetaminophen. Chem Res Toxicol (1996) 0.81

An examination of octanol and octanal metabolism to octanoic acid by horse liver alcohol dehydrogenase. Biochim Biophys Acta (1975) 0.80

N-Hydroxylation of phenacetin by hamster liver microsomes. Drug Metab Dispos (1977) 0.80

Studies on the mutagenicity of N-hydroxy-2-acetylaminofluorene in the Ames-Salmonella mutagenesis test system. Biochem Pharmacol (1978) 0.80

Utility of solution electrochemistry mass spectrometry for investigating the formation and detection of biologically important conjugates of acetaminophen. J Chromatogr (1989) 0.79

Identification of acetaminophen polymerization products catalyzed by horseradish peroxidase. J Biol Chem (1985) 0.79

Immunochemical comparison of 3'-hydroxyacetanilide and acetaminophen binding in mouse liver. Drug Metab Dispos (1998) 0.78

Kinetic evidence for multiple chemically reactive intermediates in the breakdown of phenacetin N-O-glucuronide. Pharmacology (1979) 0.78

An examination of the oxidation of aldehydes by horse liver alcohol dehydrogenase. J Biol Chem (1972) 0.78

Metabolism of [p-18O]-phenacetin: the mechanism of activation of phenacetin to reactive metabolites in hamsters. Mol Pharmacol (1979) 0.78

Mechanism of acetaminophen-stimulated NADPH oxidation catalyzed by the peroxidase-H2O2 system. Drug Metab Dispos (1991) 0.78

Acetaminophen-induced alterations in blood glucose and blood insulin levels in mice. Res Commun Chem Pathol Pharmacol (1984) 0.78

Synthesis and analysis of glucuronides of N-hydroxyamides. Drug Metab Dispos (1983) 0.77

N-hydroxylation of p-chloroacetanilde in hamsters. Biochem Pharmacol (1976) 0.77

3-Hydroxyacetaminophen: a microsomal metabolite of acetaminophen. Evidence against an epoxide as the reactive metabolite of acetaminophen. Drug Metab Dispos (1981) 0.77

The acetaminophen regioisomer 3'-hydroxyacetanilide inhibits and covalently binds to cytochrome P450 2E1. Toxicol Lett (1998) 0.76

Antagonism of bromobenzene-induced hepatotoxicity by phentolamine: evidence for a metabolism-independent intervention. Toxicol Appl Pharmacol (1988) 0.76

Horseradish peroxidase-catalyzed oxidation of acetaminophen to intermediates that form polymers or conjugate with glutathione. Mol Pharmacol (1986) 0.76

Two-dimensional J-resolved nuclear magnetic resonance spectral study of two bromobenzene glutathione conjugates. Environ Health Perspect (1985) 0.75

Mechanism of microsomal metabolism of benzene to phenol. Mol Pharmacol (1985) 0.75

Fast atom bombardment mass spectrometry and fast atom bombardment mass spectrometry/mass spectrometry of three glutathione conjugates of acetaminophen. Biomed Environ Mass Spectrom (1987) 0.75

A rapid method for preparing crystalline human hemoglobin and the separation of crystalline hemoglobin A in quantity. Biochem Biophys Res Commun (1969) 0.75

Continuing education in a rural area. Superv Nurse (1973) 0.75

Ascorbic acid inhibits covalent binding of enzymatically generated 2-acetyl-aminofluororene-N-sulfate to DNA under conditions in which it increases mutagenesis in salmonella TA-1538. Life Sci (1979) 0.75

Biotransformation of drugs. Adv Exp Med Biol (1978) 0.75

Acetaminophen toxicity to cultured rat embryos. Teratog Carcinog Mutagen (1990) 0.75

p-Nitrosophenetole: a reactive intermediate of phenacetin that binds to protein. Adv Exp Med Biol (1986) 0.75

Critical considerations in the immunochemical detection and quantitation of antigenic biomarkers. Biomed Environ Sci (1991) 0.75

Pretreatment with mixed-function oxidase inducers increases the sensitivity of the hepatocyte/DNA repair assay. Environ Mol Mutagen (1989) 0.75

A simple high-pressure liquid chromatographic assay for the N-hydroxy derivatives of phenacetin, acetaminophen, 2-acetylaminofluorene, and other hydroxamic acids. Anal Biochem (1980) 0.75

Sulfation in the metabolism and mutagenicity of N-hydroxy-2-fluorenylacetamide. Natl Cancer Inst Monogr (1981) 0.75

Evaluation of propanil and its N-oxidized derivatives for genotoxicity in the Salmonella typhimurium reversion, Chinese hamster ovary/hypoxanthine guanine phosphoribosyl transferase, and rat hepatocyte/DNA repair assays. Fundam Appl Toxicol (1988) 0.75

Covalent binding of the phenacetin metabolite p-nitrosophenetole to protein. J Pharmacol Exp Ther (1986) 0.75

Haemoglobin adducts as biomarkers of exposure to the herbicides propanil and fluometuron. Biomarkers (1996) 0.75

Reactions of glutathione with oxidative intermediates of acetaminophen. Adv Exp Med Biol (1986) 0.75

Acetaminophen peroxidation reactions. Drug Metab Rev (1989) 0.75

Production of a dimer of 2-acetylaminofluorene during the sulfation of N-hydroxy-2-acetylaminofluorene in vitro. Drug Metab Dispos (1980) 0.75

Application of chemical ionization mass spectrometry and the twin-ion technique to better define a mechanism in acetylhydrazine toxicity. Biochem Biophys Res Commun (1976) 0.75

High resolution mass spectrometric and high-field nuclear magnetic resonance spectroscopic studies of the herbicide propanil, its N-oxidative decomposition products and related compounds. Biomed Environ Mass Spectrom (1986) 0.75

Acetaminophen-induced alterations in pancreatic beta cells and serum insulin concentrations in B6C3F1 mice. Toxicol Appl Pharmacol (1990) 0.75

High-performance liquid chromatographic assay for acetaminophen and phenacetin in the presence of their metabolites in biological fluids. J Chromatogr (1979) 0.75

Direct analysis of rat bile for acetaminophen and two of its conjugated metabolites via thermospray liquid chromatography/mass spectrometry. Biomed Environ Mass Spectrom (1987) 0.75

Metabolism of 4-nitroaniline by rat liver microsomes. Drug Metab Dispos (1984) 0.75