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Xenobiotica
the fate of foreign compounds in biological systems
Volume 33, 2003 - Issue 5
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Research Article

Identification of coenzyme A-related tolmetin metabolites in rats: relationship with reactive drug metabolites

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Pages 561-570 | Published online: 22 Sep 2008

References

  • BAILEY, M. J. and DICKINSON, R. G., 1996, Chemical and immunochemical comparison of protein adduct formation of four carboxylate drugs in rat liver and plasma. Chemical Research in Toxicology, 9, 659–666.
  • BENET, L. Z., SPAHN-LANGGUTH, H., IWAKAWA, S., VOLLAND, C., MIZUMA, T., MAYER, S., MUTSCHLER, E. and LIN, E. T., 1993, Predictability of the covalent binding of acidic drugs in man. Life Sciences, 53, PL141–146.
  • BRUGGER, R., REICHEL, C., ALIA, B. G., BRUNE, K., YAMAMOTO, T., TEGEDER, I. and GEISSLINGER, G., 2001, Expression of rat liver long-chain acyl-CoA synthetase and characterization of its role in the metabolism of R-ibuprofen and other fatty acid-like xenobiotics. Biochemical Pharmacology, 61, 651–656.
  • GREGUS, Z., FEKETE, T., HALASZI, E., GYURASICS, A. and KLAASSEN, C. D., 1998, Effects of fibrates 011 the glycine conjugation of benzoic acid in rats. Drug Metabolism and Disposition, 26, 1082–1088.
  • GRILLO, M. P. and BENET, L. Z., 2002, Studies on the reactivity of clofibryl-S-acyl-CoA thioester with glutathione in vitro. Drug Metabolism and Disposition, 30, 55–62.
  • GRINDEL, J. M., 1981, The pharmacokinetic and metabolic profile of the antiinflammatory agent tolmetin in laboratory animals and man. Drug Metabolism Reviews, 12, 363–377.
  • HASHIMOTO, M., MIYAZAKI, H., NAMBU, K., FUJII, 0., ARAKAWA, S., YOSHIDA, K. and UTSUI, Y., 1979, Studies on disposition and metabolism of tolmetin, a new anti-inflammatory agent, in rats and mice. Drug Metabolism and Disposition, 7, 20–23.
  • HUTT, A. J. and CALDWELL, J., 1990, Amino acid conjugation. In G. J. Mulder (ed.), Conjugation Reactions in Drug Metabolism (London: Taylor & Francis), pp. 273–304.
  • HYNECK, M. L., SMITH, P. C., MUNAFO, A., MCDONAGH, A. F. and BENET, L. Z., 1988, Disposition and irreversible plasma protein binding of tolmetin in humans. Clinical Pharmacology and Therapeutics, 44, 107–114.
  • HYNECK, M. L., SMITH, P. C., UNSELD, E. and BENET, L. Z., 1987, HPLC determinations of tolmetin, tolmetin glucuronide and its isomeric conjugates in plasma and urine. Journal of Chromatography, 420, 349–356.
  • IwAKI, M., OGISO, T., INAGAWA, S. and KAKEHI, K., 1999, In vitro regioselective stability of 0-1-0- and 2-0-acyl glucuronides of naproxen and their covalent binding to human serum albumin. Journal of Pharmaceutical Sciences, 88, 52–57.
  • KAWAGUCHI, A., YOSHIMURA, T. and OKUDA, S., 1981, A new method for the preparation of acyl-CoA thioesters. Journal of Biochemistry, 89, 337–339.
  • KING, A. R. and DICKINSON, R. G., 1996, The utility of the bile-exteriorized rat as a source of reactive acyl glucuronide: studies with zomepirac. Journal of Pharmacological and Toxicological Methods, 36, 131–136.
  • KNIGHTS, K. M, 1998, Role of hepatic fatty acid:coenzyme A ligases in the metabolism of xenobiotic carboxylic acids. Clinical and Experimental Pharmacology and Physiology, 25, 776–782.
  • MATHEWS, C. K. and VAN HOLDE, K. E., 1990, Biochemistry (Redwood City: Benjamin Cummings). MELEGH, B., KERNER, J., JAszAi, V. and BIEBER, L. L., 1990, Differential excretion of xenobiotic acyl- esters of carnitine due to administration of pivampicillin and valproate. Biochemical Medicine and Metabolic Biology, 43, 30–38.
  • OLSEN, J., BJØRNSDOTTIR, I., TJORNELUND, J. and HANSEN, S. H., 2002, Chemical reactivity of the naproxen acyl glucuronide and the naproxen coenzyme A thioester towards bionucleophiles. Journal of Pharmaceutical and Biomedical Analysis, 29, 7–15.
  • Qiu, Y., BENET, L. Z. and BURLINGAME, A. L., 1998, Identification of the hepatic protein targets of reactive metabolites of acetaminophen in vivo in mice using two-dimensional gel electrophoresis and mass spectrometry. Journal of Biological Chemistry, 273, 17940–17953.
  • Qiu, Y., BENET, L. Z. and BURLINGAME, A. L., 2001, Identification of hepatic protein targets of the reactive metabolites of the non-hepatotoxic regioisomer of acetaminophen, 3I-hydroxyacetanilide, in the mouse in vivo using two-dimensional gel electrophoresis and mass spectrometry. Advances in Experimental Medicine and Biology, 500, 663–673.
  • SALLUSTIO, B. C., NUNTHASOMBOON, S., DROGEMULLER, C. J. and KNIGHTS, K. M., 2000, In vitro covalent binding of nafenopin-CoA to human liver proteins. Toxicology and Applied Pharmacology, 163, 176–182.
  • SHORE, L. J., FENSELAU, C., KING, A. R. and DICKINSON, R. G., 1995, Characterization and formation of the glutathione conjugate of clofibric acid. Drug Metabolism and Disposition, 23, 119–123.
  • SMITH, P. C., MCDONAGH, A. F. and BENET, L. Z., 1986, Irreversible binding of zomiperac to plasma protein in vitro and in vivo. Journal of Clinical Investigations, 77, 934–939.
  • TRACY, T. S. and HALL, S. D., 1991, Determination of the epimeric composition of ibuprofenyl-CoA. Analytical Biochemistry, 195, 24–29.
  • WANG, M. and DICKINSON, R. G., 2000, Bile duct ligation promotes covalent drug—protein adduct formation in plasma but not in liver of rats given zomepirac. Life Sciences, 68, 525–537.
  • ZIA-AMIRHOSSEINI, P., HARRIS, R. Z., BRODSKY, F. M. and BENET, L. Z., 1995, Hypersensitivity to nonsteroidal anti-inflammatory drugs. Nature Medicine, 1, 2–4.
  • ZIA-AMIRHOSSEINI, P., OJINGWA, J. C., SPAHN-LANGGUTH, H., MCDONAGH, A. F. and BENET, L. Z., 1994, Enhanced covalent binding of tolmetin to proteins in humans after multiple dosing. Clinical Pharmacology and Therapeutics, 55, 21–27.
  • ZIMMERMAN, H. J., 1994, Hepatic injury associated with nonsteroidal anti-inflammatory drugs. In A. J. Lewis and D. E. Furst (eds), Non-Steroidal Anti-Inflammatory Drugs: Mechanisms and Clinical Uses (New York: Marcel Dekker), pp. 171–194.

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