Covalent binding of acetaminophen to mouse hemoglobin. Identification of major and minor adducts formed in vivo and implications for the nature of the arylating metabolites.

[1]  T. Baillie,et al.  The use of alkoxycarbonyl derivatives for the mass spectral analysis of drug-thioether metabolites. Studies with the cysteine, mercapturic acid and glutathione conjugates of acetaminophen. , 1988, Biomedical & environmental mass spectrometry.

[2]  M. Bryant,et al.  GC/MS analysis of biologically important aromatic amines. Application to human dosimetry. , 1987, Biomedical & environmental mass spectrometry.

[3]  C. V. Smith,et al.  Acetaminophen hepatotoxicity in vivo is not accompanied by oxidant stress. , 1985, Biochemical and biophysical research communications.

[4]  P. Moldéus,et al.  Mechanisms of N-acetyl-p-benzoquinone imine cytotoxicity. , 1985, Molecular pharmacology.

[5]  T. Baillie,et al.  Identification of the major covalent adduct formed in vitro and in vivo between acetaminophen and mouse liver proteins. , 1985, Molecular pharmacology.

[6]  D. Jollow,et al.  Effect of L-ascorbic acid on acetaminophen-induced hepatotoxicity and covalent binding in hamsters. Evidence that in vitro covalent binding differs from that in vivo. , 1984, Drug metabolism and disposition: the biological fate of chemicals.

[7]  P. Eyer,et al.  Radical formation during autoxidation of 4-dimethylaminophenol and some properties of the reaction products. , 1984, Biochemical pharmacology.

[8]  A. Y. Lu,et al.  N-acetyl-p-benzoquinone imine: a cytochrome P-450-mediated oxidation product of acetaminophen. , 1984, Proceedings of the National Academy of Sciences of the United States of America.

[9]  T. Baillie,et al.  The covalent binding of acetaminophen to protein. Evidence for cysteine residues as major sites of arylation in vitro. , 1984, Chemico-biological interactions.

[10]  T. Monks,et al.  Diffusion of reactive metabolites out of hepatocytes: studies with bromobenzene. , 1984, The Journal of pharmacology and experimental therapeutics.

[11]  S. Lunte,et al.  Detection and identification of sulfhydryl conjugates of rho-benzoquinone in microsomal incubations of benzene and phenol. , 1983, Chemico-biological interactions.

[12]  P. Eyer,et al.  Site and mechanism of covalent binding of 4-dimethylaminophenol to human hemoglobin, and its implications to the functional properties. , 1983, Molecular pharmacology.

[13]  S. Nelson,et al.  Synthesis, decomposition kinetics, and preliminary toxicological studies of pure N-acetyl-p-benzoquinone imine, a proposed toxic metabolite of acetaminophen. , 1982, Journal of medicinal chemistry.

[14]  S. Nelson,et al.  Metabolic activation and drug toxicity. , 1982, Journal of medicinal chemistry.

[15]  J. Bakke Conversion of the prosthetic moieties of glutathione pathway conjugates to the corresponding S-acetates. , 1982, Biomedical mass spectrometry.

[16]  K. Ham,et al.  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. , 1980, Journal of medicinal chemistry.

[17]  J. Mitchell,et al.  Renal necrosis, glutathione depletion, and covalent binding after acetaminophen. , 1978, Toxicology and applied pharmacology.

[18]  G. Mudge,et al.  Covalent binding of metabolites of acetaminophen to kidney protein and depletion of renal glutathione. , 1978, The Journal of pharmacology and experimental therapeutics.

[19]  B B Brodie,et al.  Acetaminophen-induced hepatic necrosis. I. Role of drug metabolism. , 1973, The Journal of pharmacology and experimental therapeutics.

[20]  B B Brodie,et al.  Acetaminophen-induced hepatic necrosis. IV. Protective role of glutathione. , 1973, The Journal of pharmacology and experimental therapeutics.

[21]  B B Brodie,et al.  Acetaminophen-induced hepatic necrosis. II. Role of covalent binding in vivo. , 1973, The Journal of pharmacology and experimental therapeutics.

[22]  B. Brodie,et al.  ACETAMINOPHEN-INDUCED HEPATIC NECROSIS. III. CYTOCHROME P-450-MEDIATED COVALENT BINDING IN VITRO , 1973 .

[23]  L. Prescott,et al.  Plasma-paracetamol half-life and hepatic necrosis in patients with paracetamol overdosage. , 1971, Lancet.

[24]  E. M. Boyd,et al.  Liver necrosis from paracetamol. , 1966, British journal of pharmacology and chemotherapy.

[25]  Oliver H. Lowry,et al.  Protein measurement with the Folin phenol reagent. , 1951, The Journal of biological chemistry.

[26]  C. Calleman,et al.  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. , 1988, Chemico-biological interactions.

[27]  M. Novak,et al.  Hydrolysis of the model carcinogen N-(pivaloyloxy)-4-methoxyacetanilide: involvement of N-acetyl-p-benzoquinone imine , 1986 .

[28]  T. Baillie,et al.  Structural characterization of the major covalent adduct formed in vitro between acetaminophen and bovine serum albumin. , 1985, Chemico-biological interactions.

[29]  L. Ehrenberg,et al.  Covalent binding of reactive intermediates to hemoglobin as an approach for determining the metabolic activation of chemicals--ethylene. , 1982, Drug metabolism reviews.

[30]  J. Gillette The problem of chemically reactive metabolites. , 1982, Drug metabolism reviews.

[31]  M. A. Pereira,et al.  Binding of chemical carcinogens and mutagens to rat hemoglobin. , 1981, Chemico-biological interactions.

[32]  Y. Vaishnav,et al.  The formation of arylating and alkylating metabolites of phenacetin in hamsters and hamster liver microsomes. , 1981, Molecular pharmacology.

[33]  L. Ehrenberg,et al.  Evaluation of genetic risks of alkylating agents. II. Haemoglobin as a dose monitor. , 1976, Mutation research.

[34]  S. Thorgeirsson,et al.  Acetaminophen-induced hepatic necrosis. V. Correlation of hepatic necrosis, covalent binding and glutathione depletion in hamsters. , 1974, Pharmacology.