(Q32052639)

5 July 2017

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title

Paracetamol (acetaminophen)-induced toxicity: molecular and biochemical mechanisms, analogues and protective approaches (English)

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ORCID Public Data File 2021

5 July 2017

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author name string

J G Bessems

series ordinal

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5 July 2017

N P Vermeulen

series ordinal

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5 July 2017

language of work or name

English

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publication date

1 January 2001

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Critical Reviews in Toxicology

5 July 2017

published in

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5 July 2017

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5 July 2017

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5 July 2017

page(s)

55-138

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Paracetamol-stimulated lipid peroxidation in isolated rat and mouse hepatocytes

5 July 2017

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The influence of ebselen on the toxicity of cisplatin in LLC-PK1 cells

21 January 2018

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DNA sequencing of a mouse liver protein that binds selenium: implications for selenium's mechanism of action in cancer prevention

21 January 2018

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Purification, antibody production, and partial amino acid sequence of the 58-kDa acetaminophen-binding liver proteins

21 January 2018

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https://api.crossref.org/works/10.1080%2F20014091111677

Immunochemical analysis of acetaminophen covalent binding to proteins. Partial characterization of the major acetaminophen-binding liver proteins

21 January 2018

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Series: current issues in mutagenesis and carcinogenesis, No. 65. The genotoxicity and carcinogenicity of paracetamol: a regulatory (re)view

21 January 2018

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Acetaminophen hepatotoxicity: correspondence of selective protein arylation in human and mouse liver in vitro, in culture, and in vivo

21 January 2018

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Inhibition of protein phosphatase activity and changes in protein phosphorylation following acetaminophen exposure in cultured mouse hepatocytes.

21 January 2018

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https://api.crossref.org/works/10.1080%2F20014091111677

Identification of the mouse liver 44-kDa acetaminophen-binding protein as a subunit of glutamine synthetase

21 January 2018

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https://api.crossref.org/works/10.1080%2F20014091111677

Mitochondrial dysfunction in paracetamol hepatotoxicity: in vitro studies in isolated mouse hepatocytes

21 January 2018

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https://api.crossref.org/works/10.1080%2F20014091111677

Genetic and environmental factors associated with variation of human xenobiotic glucuronidation and sulfation

21 January 2018

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https://api.crossref.org/works/10.1080%2F20014091111677

N-Hydroxyacetaminophen: a postulated toxic metabolite of acetaminophen

21 January 2018

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https://api.crossref.org/works/10.1080%2F20014091111677

Free radical formation from organic hydroperoxides in isolated human polymorphonuclear neutrophils

21 January 2018

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https://api.crossref.org/works/10.1080%2F20014091111677

Hepatic cell division and tissue repair: a key to survival after liver injury

21 January 2018

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https://api.crossref.org/works/10.1080%2F20014091111677

Selective protein covalent binding and target organ toxicity

21 January 2018

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https://api.crossref.org/works/10.1080%2F20014091111677

The spontaneous and enzymatic reaction of N-acetyl-p-benzoquinonimine with glutathione: A stopped-flow kinetic study

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

The covalent binding of acetaminophen to cellular nucleic acids as the result of the respiratory burst of neutrophils derived from the HL-60 cell line

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Immediate rise in intracellular calcium and glycogen phosphorylase a activities upon acetaminophen covalent binding leading to hepatotoxicity in mice

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Over-the-counter analgesics and risk of ovarian cancer

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Inter-subject and ethnic differences in paracetamol metabolism

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

N-acetyl-p-benzoquinone imine: a cytochrome P-450-mediated oxidation product of acetaminophen

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Decreased glucuronidation and increased bioactivation of acetaminophen in Gilbert's syndrome

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Induction of micronuclei and aneuploidy by the quinone-forming agents benzene and o-phenylphenol

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Xenobiotic metabolism by prostaglandin H synthase

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Evidence against deacetylation and for cytochrome P450-mediated activation in acetaminophen-induced nephrotoxicity in the CD-1 mouse

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Studies on the mechanism of toxicity of acetaminophen. Synthesis and reactions of N-acetyl-2,6-dimethyl- and N-acetyl-3,5-dimethyl-p-benzoquinone imines

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Free-radical metabolites of acetaminophen and a dimethylated derivative

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Thrombocytopenia following acute acetaminophen overdose

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Inhibition of Prostaglandin Synthetase in Brain explains the Anti-pyretic Activity of Paracetamol (4-Acetamidophenol)

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Intracellular calcium disruption as a secondary event in acetaminophen-induced hepatotoxicity.

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Positional isomers of acetaminophen differentially induce proliferation of cultured breast cancer cells

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Comparative toxicities and analgesic activities of three monomethylated analogues of acetaminophen

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Cytochrome P-450 isozyme selectivity in the oxidation of acetaminophen.

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Glutathione-degrading capacities of liver and kidney in different species

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Nitrotyrosine-protein adducts in hepatic centrilobular areas following toxic doses of acetaminophen in mice

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Mechanisms of Acetaminophen Toxicity: Immunochemical Detection of Drug-Protein Adducts

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Structural characterization of the major covalent adduct formed in vitro between acetaminophen and bovine serum albumin

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Comparative cytotoxic effects of acetaminophen (N-acetyl-p-aminophenol), a non-hepatotoxic regioisomer acetyl-m-aminophenol and their postulated reactive hydroquinone and quinone metabolites in monolayer cultures of mouse hepatocytes

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

The Role of Covalent Binding to Microsomal Proteins in the Hepatotoxicity of Acetaminophen

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Paracetamol inhibits replicative DNA synthesis and induces sister chromatid exchange and chromosomal aberrations by inhibition of ribonucleotide reductase

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Induction mechanisms of cytochrome P450 2E1 in liver: Interplay between ethanol treatment and starvation

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Ethanol-, fasting-, and acetone-inducible cytochromes P-450 in rat liver: regulation and characteristics of enzymes belonging to the IIB and IIE gene subfamilies.

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Immunochemical analysis of quinol-thioether-derived covalent protein adducts in rodent species sensitive and resistant to quinol-thioether-mediated nephrotoxicity

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Generalized cytochrome P450-mediated oxidation and oxygenation reactions in aromatic substrates with activated N-H, O-H, C-H, or S-H substituents

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Superoxide dismutase and catalase protect cultured hepatocytes from the cytotoxicity of acetaminophen.

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Metabolism of acetaminophen by cultured rat hepatocytes. Depletion of protein thiol groups without any loss of viability

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Different patterns of regulation of the genes encoding the closely related 56 kDa selenium- and acetaminophen-binding proteins in normal tissues and during carcinogenesis

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Effects of ether anaesthesia and fasting on various cytochromes P450 of rat liver and kidney

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Metabolic evidence for the involvement of enzymatic bioactivation in the cataractogenicity of acetaminophen in genetically susceptible (C57BL6) and resistant (DBA2) murine strains

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Effect of pregnenolone-16α-carbonitrile and dexamethasone on acetaminophen-induced hepatotoxicity in mice

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Hyperalgesia mediated by spinal glutamate or substance P receptor blocked by spinal cyclooxygenase inhibition

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Role of hepatocellular regeneration and hepatolobular healing in the final outcome of liver injury. A two-stage model of toxicity

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Toxicodynamics of low level toxicant interactions of biological significance: inhibition of tissue repair

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Autoprotection: stimulated tissue repair permits recovery from injury

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Predictive value of liver slices for metabolism and toxicity in vivo: use of acetaminophen as a model hepatotoxicant

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Acetaminophen alters estrogenic responses in vitro: inhibition of estrogen-dependent vitellogenin production in trout liver cells

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Evidence for the involvement of N-acetyl-p- quinoneimine in acetaminophen metabolism

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Paracetamol metabolism in pregnancy

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Zonal distribution of paracetamol glucuronidation in the isolated perfused rat liver

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Nephrotoxicity of paracetamol in the rat—mechanistic and therapeutic aspects

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Prevention of paracetamol-induced liver injury by fructose

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Preferred orientations in the binding of 4'-hydroxyacetanilide (acetaminophen) to cytochrome P450 1A1 and 2B1 isoforms as determined by 13C- and 15N-NMR relaxation studies.

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Mechanisms of the Formation and Disposition of Reactive Metabolites That can Cause Acute Liver Injury

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Acetaminophen nephrotoxicity in the rat. Renal metabolic activation in vitro

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

The role of p-aminophenol in acetaminophen-induced nephrotoxicity: effect of bis(p-nitrophenyl) phosphate on acetaminophen and p-aminophenol nephrotoxicity and metabolism in Fischer 344 rats

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Acetaminophen nephrotoxicity in the rat: quantitation of renal metabolic activation in vivo.

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Differential effects of arylating and oxidizing analogs of N-acetyl-p-benzoquinoneimine on red blood cell membrane proteins

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Implication of free radical mechanisms in ethanol-induced cellular injury

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Effects of fluorine substitution on drug metabolism: pharmacological and toxicological implications

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Identification of S-(2,5-dihydroxyphenyl)-cysteine and S-(2,5-dihydroxyphenyl)-N-acetyl-cysteine as urinary metabolites of acetaminophen in the mouse. Evidence for p-benzoquinone as a reactive intermediate in acetaminophen metabolism

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Metabolism of tert-butylhydroquinone to S-substituted conjugates in the male Fischer 344 rat.

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Interaction of p-benzoquinone and p-biphenoquinone with microtubule proteins in vitro.

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Idiosyncratic drug reactions. Metabolic bioactivation as a pathogenic mechanism

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Acetaminophen-induced hepatic necrosis. V. Correlation of hepatic necrosis, covalent binding and glutathione depletion in hamsters.

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Paracetamol Overdosage Pharmacological Considerations and Clinical Management

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Strain differences in susceptibility of normal and diabetic rats to acetaminophen hepatotoxicity

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Mechanism of decreased acetaminophen glucuronidation in the fasted rat.

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Protein targets of xenobiotic reactive intermediates

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Immunoblot analysis of protein containing 3-(cystein-S-yl)acetaminophen adducts in serum and subcellular liver fractions from acetaminophen-treated mice

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

A metabolite of acetaminophen covalently binds to the 56 kDa selenium binding protein

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Identification of the hepatic protein targets of reactive metabolites of acetaminophen in vivo in mice using two-dimensional gel electrophoresis and mass spectrometry

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

In vitro effects of acetaminophen metabolites and analogs on the respiration of mouse liver mitochondria

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

International Commission for Protection against Environmental Mutagens and Carcinogens. An evaluation of the genetic toxicity of paracetamol.

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Structure-activity study of paracetamol analogs: inhibition of replicative DNA synthesis in V79 Chinese hamster cells

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Acetaminophen-induced depletion of glutathione and cysteine in the aging mouse kidney

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Protection Against Acetaminophen Hepatotoxicity by Ribose-Cysteine (RibCys)

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Prodrugs of L-cysteine as protective agents against acetaminophen-induced hepatotoxicity. 2-(Polyhydroxyalkyl)- and 2-(polyacetoxyalkyl)thiazolidine-4(R)-carboxylic acids.

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Protection against Hepatotoxicity by a Single Dose of Amphetamine: The Potential Role of Heat Shock Protein Induction

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Analgesic use and chronic renal disease

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Analgesic nephropathy in rodents

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Dose-dependent pharmacokinetics of acetaminophen: evidence of glutathione depletion in humans.

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

The structure of a complex of hexameric insulin and 4'-hydroxyacetanilide

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Paracetamol toxicity: is enzyme induction important?

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Glutathione synthetase-deficient lymphocytes and acetaminophen toxicity

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Paracetamol and self poisoning

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Effect of ethanol on hepatotoxicity of acetaminophen in mice and on reactive metabolite formation by mouse and human liver microsomes

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Repetitive microvolumetric sampling and analysis of acetaminophen and its toxicologically relevant metabolites in murine plasma and urine using high performance liquid chromatography

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Heterogeneous expression of sulphotransferases in periportal and perivenous hepatocytes prepared from male and female rat liver.

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Alkylation of the liver plasma membrane and inhibition of the Ca2+ ATPase by acetaminophen

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Induction of cytochrome P450-dependent monooxygenases in hamster tissues by fasting

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Glutathione enhancement in various mouse organs and protection by glutathione isopropyl ester against liver injury

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

The mechanism of prevention of paracetamol-induced hepatotoxicity by 3,5-dialkyl substitution

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Paracetamol, 3-monoalkyl- and 3,5-dialkyl derivatives: comparison of their hepatotoxicity in mice

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Cytochrome P-450-mediated oxidation of substrates by electron-transfer; role of oxygen radicals and of 1- and 2-electron oxidation of paracetamol

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Molecular aspects of paracetamol-induced hepatotoxicity and its mechanism-based prevention

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Cyclization-activated prodrugs: N-(substituted 2-hydroxyphenyl and 2-hydroxypropyl)carbamates based on ring-opened derivatives of active benzoxazolones and oxazolidinones as mutual prodrugs of acetaminophen.

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Intracellular cysteine delivery system that protects against toxicity by promoting glutathione synthesis

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Inhibition and induction of cytochrome P4502E1-catalyzed oxidation by isoniazid in humans

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Paracetamol increases sensitivity to ultraviolet (UV) irradiation, delays repair of the UNG-gene and recovery of RNA synthesis in HaCaT cells

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Intracellular glutathione in human hepatocytes incubated with S-adenosyl-L-methionine and GSH-depleting drugs

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Mutagenicity studies on paracetamol in human volunteers II. Unscheduled DNA synthesis and micronucleus test

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

Biochemistry of Oxidative Stress

21 January 2018

1 reference

https://api.crossref.org/works/10.1080%2F20014091111677

21 January 2018

Identifiers

DOI

10.1080/20014091111677

1 reference

5 July 2017

1 reference