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Research Article

Nonenzymatic Contributions to Xenobiotic Metabolism

Pages 25-50 | Published online: 22 Sep 2008

References

  • Testa B., Di Carlo F. J., Jenner P. Xenobiotic metabolism: Necessity, chance, mishap, or none of the above?. Concepts in Drug Metabolism. Dekker, New York 1981; 515–535, Part B
  • Wilshire J., Sawyer D. T. ldquo;Redox chemistry of dioxygen species”. Acc. Chem. Res. 1979; 12: 105–110
  • Rauckman E. J., Rosen G. M., Kitchell B. B. ldquo;Superoxide radical as an intermediate in the oxidation of hydroxylamines by mixed function amine oxidase”. Mol. Pharmacol. 1979; 15: 131–137
  • Cohen G., Cederbaum A. I. ldquo;Chemical evidence for production of hydroxyl radicals during microsomal electron transfer”. Science 1979; 204: 66–68
  • O'Brien P. J. ldquo;Hydroperoxides and superoxides in microsomal oxidations”. Pharmacol. Ther. A 1978; 2: 517–536
  • Trager W. F. The postenzymatic chemistry of activated oxygen. Drug Metab. Rev. 1982; 13(1)51
  • Jonsson G. ldquo;Chemical neurotoxins as denervation tools in neurology”. Ann. Rev. Neurosci. 1980; 3: 169–187
  • Blisard K. S., Mieyal J. J. ldquo;Characterization of the aniline hydroxylase activity of erythrocytes”. J. Biol. Chem. 1979; 254: 5104–5110
  • Castro C. E. ldquo;Mechanisms of reaction of hemeproteins with oxygen and hydrogen peroxide in the oxidation of organic substrates”. Pharmacol. Ther. 1980; 10: 171–189
  • Kurono Y., Maki T., Yotsuyanagi T., Ikeda K. ldquo;Esterase-like activity of human serum albumin: Structure-activity relationships for the reactions with phenyl acetates and p-nitrophenyl esters”. Chem. Pharm. Bull. 1979; 27: 2781–2786
  • Morikawa M., Inoue M., Tsuboi M., Sugiura M. ldquo;Studies on aspirin esterase of human serum”. Jap. J. Pharmacol. 1979; 29: 581–586
  • Boroujerdi M., Kung H.-C., Wilson A. G. E., Anderson M. W. ldquo;Metabolism and DNA binding of benzo[a]pyrene in vivo in the rat”. Cancer Res. 1981; 41: 951–957
  • Osterman-Golkar S., Ehrenberg L. E., Segerback D., Hallström I. Evaluation of genetic risks of alkylating agents, II: Haemoglobin as a dose monitor. Mutation Res. 1976; 34: 1–10
  • Testa B., Jenner P. Drug Metabolism: Chemical and Biochemical Aspects. Dekker, New York 1976; 325–328
  • van Bladeren P. J. The dual role of glutathione conjugation in the biotransformation of xenobiotics. Ph.D. Thesis, University of Leiden. 1981
  • Ketterer B. Xenobiotic metabolism by nonenzymatic reactions of glutathione. Symposium on Metabolism and Pharmacokinetics of Environmental Chemicals in Man, Sarasota, Fla., June, 7–121981
  • Chen K. C., Dorough H. W. Glutathione and mercapturic acid conjugations in the metabolism of 2, 4-dinitrobromobenzene. Drug Chem. Toxicol. 1980; 3: 305–318
  • Livesey J. C., Anders M. W. In vitro metabolism of 1, 2-dihaloethanes to ethylene. Drug Metab. Disp. 1979; 7: 199–203
  • Crawford M. J., Hutson D. H., Stoydin G. ldquo;The metabolic fate of a herbicidal methylmercapto-s-triazine (cyanatryn) in the rat”. Xenobiotica 1980; 10: 169–185
  • Hallett G., Williams D. L. H. The reactivity of thiourea, alkylthioureas, cysteine, glutathione, S-methylcysteine, and methionine towards N-methyl-N-nitrosaniline in acid solution. J. Chem. Soc. P.T. 1980; 11: 624–627
  • Timbrell J. A., Mitchell J. R., Snodgrass W. R., Nelson S. D. ldquo;Isoniazid hepatotoxicity: the relationship between covalent binding and metabolism in vivo”. J. Pharmacol. Exp. Ther. 1980; 213: 364–369
  • Talseth T., Haegele K. D., McNay J. L. Studies in the rabbit on 3-methyltrlazolophthalazine, an acetylated metabolite of hydralazine. Drug Metab. Disp. 1980; 8: 73–76
  • O'Donnell J. P., Proveaux W. J., Ma J. K. H. ldquo;HPLC studies of reaction of hydralazine with biogenic aldehydes and ketones”. J. Pharm. Sci. 1979; 68: 1524–1526
  • O'Donnell J. P., Proveaux W. J., Ma J. K. H. ldquo;Kinetic studies of hydralazine reaction with acetaldehyde”. J. Pharm. Sci. 1979; 68: 1256–1258
  • Juchau M. R., Horita A. ldquo;Metabolism of hydrazine derivatives of pharmacologic interest”. Drug Metab. Rev. 1972; 1: 71–100
  • Jenner P., Testa B. ldquo;Novel pathways in drug metabolism”. Xenobiotica 1978; 8: 1–25
  • Collins M. A., Nijm W. P., Borge G. F., Teas G., Goldfarb C. ldquo;Dopamine-related tetrahydroisoquinolines: Significant urinary excretion by alcoholics after alcohol consumption”. Science 1979; 206: 1184–1186
  • O'Donnell J. P. The reaction of amines with carbonyls: Its significance in the nonenzymatic metabolism of xenobiotics. Drug Metab. Rev. 1982; 13(1)123
  • Becker A. R., Sternson L. A. ldquo;Nonenzymatic reduction of nitrosobenzene to phenylhydroxylamine by NAD(P)H”. Bioorg. Chem. 1980; 9: 305–312
  • Kyo Y. N., Muranaka Y., Hikichi N., Niwa H. N, O-Diacetyl-p-aminophenol formation by combined use of aspirin with phenacetin and acetaminophen in vivo. J. Pharm. Soc. Jap. 1980; 100: 1043–1047
  • Brock N., Stekar J., Pohl J., Niemeyer U., Scheffler G. Acrolein, the causative factor of urotoxic side-effects of cyclophosphamide, ifosfamide, trofosfamide, and sulfosfamide. Arzneim.-Forsch. 1979; 29: 659–661
  • Berrigan M. J., Gurtoo H. L., Sharma S. D., Struck R. F., Marinello A. J. ldquo;Protection by N-acetylcysteine of cyclophosphamide metabolism-related in vivo depression of mixed function oxygenase activity and in vitro denaturation of cytochrome P-450”. Biochem. Biophys. Res. Comm. 1980; 93: 797–803
  • Beckett A. H., Navas G. E., Hutt A. J., Farag M. ldquo;Disappearing N-hydroxy compounds”. J. Pharm. Pharmacol. 1979; 31: 476–477
  • Andrews L. S., Pohl L. R., Hinson J. A., Fisk C. L., Gillette J. R. ldquo;Production of a dimer of 2-acetylaminofluorene during the sulfation of N-hydroxy-2-acetylaminofluorene in vitro”. Drug Metab. Disp. 1979; 7: 296–300
  • Nesnow S., Bergman H. 1, 2-Naphthoquinone: A mediator of non-enzymatic benzo[a]pyrene oxidation. Life Sci. 1979; 25: 2099–2104
  • Gemborys M. W., Mudge G. H., Gribble G. W. Mechanism of decomposition of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen. J. Med. Chem. 1980; 23: 304–308
  • Hathway D. E. ldquo;The importance of (non-enzymic) chemical reaction processes to the fate of foreign compounds in mammals”. Chem. Soc. Rev. 1980; 9: 63–89
  • Lindeke B. The non-and postenzymatic chemistry of N-oxygenated molecules. Drug Metab. Rev. 1982; 13(1)71
  • Khuthier A. H., Al-Iraqui M. A., Hallstriim G., Lindeke B. Rearrangement of prop-2-ynylic N-oxides to O-allenyl hydroxylamines. J. Chem. Soc. Chem. Comm. 1979; 9–10
  • Kopecky J., Gut I., Nerudova J., Zachardova D., Holecek V., Filip J. Acrylonitrile metabolism in the rat. Arch. Toxicol. 1980, Suppl. 4: 322–324
  • Vermeulen N. P. E., Bakker B. H., Eylers D., Breimer D. D. ldquo;The epoxide-diol pathway in the metabolism of vinylbital in rat and man”. Xenobiotica 1980; 10: 159–168
  • Vermeulen N. P. E., Bakker B. H., Schultink J., van der Gen A., Breimer D. D. ldquo;The epoxide-diol pathway in the metabolism of hexobarbital in rat and man”. Xenobiotica 1979; 9: 289–299
  • Salvesen B., Testa B., Beckett A. H. ldquo;NMR and ORD determination of the configuration of N-cyanobenzylamphetamine (AN 1)”. Arzneim.-Forsch. 1974; 24: 137–140
  • Tabachnik N. F., Peterson C. M., Cerami A. ldquo;Studies on the reduction of sputum viscosity in cystic fibrosis using an orally absorbed protected thiol”. J. Pharmacol. Exp. Ther. 1980; 214: 246–249
  • Inotsume N., Nakano M. ldquo;Reversible azomethine bond cleavage of 2-fluoro derivatives of benzodiazepines in acidic solutions at body temperature”. Int. J. Pharmaceut. 1980; 6: 147–154
  • Inotsume N., Nakano M. ldquo;Reversible ring-opening reactions of nimetazepam and nitrazepam in acidic media at body temperature”. J. Pharm. Sci. 1980; 69: 1331–1334
  • Sato T., Konishi M., Ago T., Nakagawa Y., Iwatani K., Mori Y. ldquo;Metabolism of peptido-aminobenzophenone (2-o-chlorobenzoyl-4-chloro-N -methyl-N-glycyl-glycinanilide) in dogs”. Xenobiotica 1980; 10: 125–133
  • Noda A., Matsuyama K., Yen S.-H., Sogabe K., Aso Y., Iguchi S., Noda H. Fate of hydralazine in man, I: Reactions under gastric conditions. Chem. Pharm. Bull. 1979; 27: 2820–2826
  • Digenis G. A., Issidorides C. H. ldquo;Some biochemical aspects of N-nitroso compounds”. Bioorg. Chem. 1979; 8: 97–137
  • Steward D. J., Inaba T., Lucassen M., Kalow W. ldquo;Cocaine metabolism: Cocaine and norcocaine hydrolysis by liver and serum esterases”. Clin. Pharmacol. Ther. 1979; 25: 464–468
  • Long D. F., Repta A. J. Cisplatin: Chemistry, distribution, and biotransformation. Biopharmaceut. Drug Disp. 1981; 2: 1–16
  • Long D. F., Repta A. J., Sternson L. A. ldquo;The reactivity of cisplatin in plasma: Implication for sample handling in pharmacokinetic studies”. Int. J. Pharmaceut. 1980; 6: 167–173
  • Frochaux-Zeidler E. L., Testa B. ldquo;Metabolic investigations of Proxibarbal I 5-allyl-5-(2-hydroxypropyl) barbituric acid] in vitro”. Pharm. Acta Helv. 1980; 55: 79–82
  • Wittekind H. H., Testa B. ldquo;Valofan diastereoisomers: Their analysis by HPLC and interconversion with Proxibarbal in aqueous solution”. J. Chromatogr. 1979; 179: 370–375
  • Wittekind H. H., Testa B., in preparation

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