Reactivity of mefenamic acid 1-O-acyl glucuronide with proteins in vitro and ex vivo

Drug Metabolism and Disposition

Volumn 24, Issue 8, 1996, Pages 842-849

  McGurk, Karen A ^c   Remmel, Rory P ^b   Hosagrahara, Vinayak P ^b   Tosh, David ^a   Burchell, Brian ^a  

^a UNIVERSITY OF DUNDEE   (United Kingdom)

^b UNIVERSITY OF MINNESOTA   (United States)

^c UNIVERSITY OF DUNDEE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CELL PROTEIN; DRUG METABOLITE; GLUCURONIDE; GLUCURONOSYLTRANSFERASE; MEFENAMIC ACID; NONSTEROID ANTIINFLAMMATORY AGENT;

ANIMAL CELL; AQUEOUS SOLUTION; ARTICLE; CELL STRAIN V 79; DRUG GLUCURONIDATION; DRUG ISOLATION; DRUG PROTEIN BINDING; DRUG STABILITY; DRUG STRUCTURE; GAS CHROMATOGRAPHY; HALF LIFE TIME; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN EXPERIMENT; MASS SPECTROMETRY; NONHUMAN; ORAL DRUG ADMINISTRATION; PH; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; URINALYSIS;

ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; CELL LINE; CRICETINAE; CRICETULUS; GLUCURONATES; HALF-LIFE; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MEFENAMIC ACID; PROTEIN BINDING;

ANIMALIA; CRICETINAE; CRICETULUS GRISEUS;

EID: 0029790316     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (48)

1. C. V. Winder, J. Wax, L. Scotti, R. A. Scherrer, E. M. Jones, and F. W. Short: Anti-inflammatory, antipyretic and antinociceptive properties of N-(2,3-xylyl)anthranilic acid (mefenamic acid). J. Pharmacol. 138, 405-413 (1962).
2. L. J. Cass and W. S. Frederick: Experiments in relief of clinical pain with N-(2,3-xylyl)anthranilic acid (Cl-473: mefenamic acid). J. Pharmacol. 139, 172-176 (1963).
3. F. Dudley-Hart, E. C. Huskisson, and B. M. Ansell: The nonsteroidal anti-inflammatory agents. In "Drug Treatment of the Rheumatic Diseases" (F. Dudley-Hart, ed.), pp. 9-64. Williams & Wilkins, London, 1987.
4. C. E. Robertson, M. J. Ford, V. Van Someren, M. Dlugolecka, and L. F. Prescott: Mefenamic acid nephropathy. Lancet 2, 232-233 (1980).
5. P. L. Drury, L. G. Asirdas, and G. V. Bulger: Mefenamic acid nephropathy: further evidence. Br. Med. J. 282, 865-866 (1981).
6. K. L. Woods: Mefenamic acid nephropathy. Br. Med. J. 282, 1471 (1981).
7. A. Taha, R. J. Lenton, P. S. Murdoch, and N. R. Peden: Non-oliguric renal failure during treatment with mefenamic acid in elderly patients: a continuing problem. Br. Med. J. 291, 661-662 (1985).
8. D. A. S. Jenkins, D. J. Harrison, M. K. MacDonald, and R. J. Winney: Mefenamic acid nephropathy: an interstitial and mesangial lesion. Nephrol. Dial. Transplant. 2, 217-220 (1988).
9. R. T. McCluskey and R. B. Colvin: Immunological aspects of renal tubular and interstitial diseases. Annu. Rev. Med. 29, 191-203 (1978).
10. A. J. Glazko: Pharmacology of the fenamates. III. Metabolic disposition. Ann. Phys. Med. 9, (Suppl.) 23-36 (1968).
11. I. Sato, Y. Yamane, K. Ito, and H. Bando: Structures of mefenamic acid metabolites from human urine. Biol. Pharm. Bull. 8, 311-312 (1993).
12. H. Egger, F. Bartlett, H. Yuan, and J. Karliner: Metabolism of pirprofen in man, monkey, rat and mouse. Drug Metab. Dispos. 10, 529-536 (1982).
13. L. Z. Benet and H. Spahn: Acyl migration and covalent binding of drug glucuronides: potential toxicity mediators. In "Cellular and Molecular Aspects of Glucuronidation" (G. Siest, J. Magdalou, and B. Burchell, eds.), vol. 173, pp. 261-269. INSERM/John Libbey Eurotext Ltd., London, 1988.
14. J. Magdalou, C. C. Lafaurie, and G. Siest: Glucuronidation of 2-aryl propionic acids pirprofen, flurbiprofen, and ibuprofen by human liver microsomes. Drug Metab. Dispos. 18, 692-697 (1990).
15. M. El Mouelhi and K. W. Bock: Stereoselective (S)- and (R)-naproxen glucuronosyltransferases of rat liver. Drug Metab. Dispos. 19, 304-308 (1991).
16. H. K. Kroemer and U. Klotz: Glucuronidation of drugs: a re-evaluation of the pharmacological significance of the conjugates and modulating factors (review). Clin. Pharmacokinet. 23, 292-310 (1992).
17. T. Ebner and B. Burchell: Substrate specificities of two stably expressed human liver UDP-glucuronosyltransferases of the UGT1 gene family. Drug Metab. Dispos. 21, 50-55 (1993).
18. B. Burchell, C. H. Brierley, and D. Rance: Specificity of human UDP-glucuronosyltransferases and xenobiotic glucuronidation. Life Sci. 57, 1819-1831 (1995).
19. H. Spahn-Langguth and L. Z. Benet: Acyl glucuronides revisited: is the glucuronidation process a toxification as well as a detoxification mechanism? (review). Drug Metab. Rev. 24, 5-47 (1992).
20. L. Z. Benet, L. H. Spahn, S. Iwakawa, C. Volland, T. Mizuma, S. Mayer, E. Mutschler, and E. T. Lin: Predictability of the covalent binding of acidic drugs in man (review). Life Sci. 53, PL141-PL146 (1993).
21. R. G. Dickinson, A. R. King, A. M. Williams, and S. Worrall: Reactivity of acyl glucuronides: in vivo consequences. In "Proceedings of the 7th International Glucuronidation Workshop." 1993.
22. H. Spahn-Langguth and L. Z. Benet: Microsomal acyl glucuronidation: enzyme-kinetic studies with labile glucuronides (review). Pharmacology 46, 268-273 (1993).
23. J. Hasegawa, P. Smith, and L. Z. Benet: Apparent intramolecular acyl migration of zomepirac glucuronide. Drug Metab. Dispos. 10, 469-473 (1982).
24. K. A. Sinclair and J. Caldwell: The formation of β-glucuronidase-resistant glucuronides by the intramolecular rearrangement of glucuronic acid conjugates at mild alkaline pH. Biochem. Pharmacol. 31, 963-967 (1982).
25. E. M. Faed: Properties of acyl glucuronides: implications for studies of the pharmacokinetics and metabolism of acidic drugs. Drug Metab. Rev. 15, 1213-1249 (1984).
26. J. Hansen-Moller, C. Cornett, L. Dalgaard, and S. H. Hansen: Isolation and identification of the rearrangement products of diflunisal 1-O-acyl glucuronide. J. Pharm. Biomed. Anal. 6, 229-240 (1988).
27. 9-11-carboxytetrahydrocannabinol glucuronide. Chem. Res. Toxicol. 2, 316-324 (1989).
28. P. C. Smith, A. F. McDonagh, and L. Z. Benet: Irreversible binding of zomepirac to plasma protein in vitro and in vivo. J. Clin. Invest. 77, 934-939 (1986).
29. D. S. Wells, F. W. Janssen, and H. W. Ruelius: Interactions between oxaprozin glucuronide and human serum albumin. Xenobiotica 17, 1437-1449 (1987).
30. J. A. Watt and R. G. Dickinson: Reactivity of diflunisal acyl glucuronide in human and rat plasma and albumin solutions. Biochem. Pharmacol. 39, 1067-1075 (1990).
31. N. Dubois, F. Lapicque, M. Maurice, M. Pritchard, S. Fournel-Gigleux, J. Magdalou, M. Abiteboul, G. Siest, and P. Netter: In vitro irreversible binding of ketoprofen glucuronide to plasma proteins. Drug Metab. Dispos. 21, 617-622 (1993).
32. A. Kretz-Rommel and U. A. Boelsterli: Diclofenac covalent binding is dependent on acyl glucuronide formation and is inversely related to P450-mediated acute cell injury in cultured rat hepatocytes. Toxicol. Appl. Pharmacol. 120, 155-161 (1993).
33. J. C. Ojingwa, H. Spahn-Langguth, and L. Z. Benet: Irreversible binding of tolmetin to macromolecules via its glucuronide: binding to blood constituents, tissue homogenates, and subcellular fractions. Xenobiotica 24, 495-506 (1994).
34. R. B. Van Breeman and C. Fenselau: Acylation of albumin by 1-O-acyl glucuronides. Drug Metab. Dispos. 13, 318-320 (1985).
35. R. G. Dickinson: Acyl glucuronide conjugates: reactive metabolites of non-steroidal anti-inflammatory drugs (review). Proc. West Pharmacol. Soc. 36, 157-162 (1993).
36. A. Ding, J. C. Ojingwa, A. F. McDonagh, A. L. Burlingame, and L. Z. Benet: Evidence for covalent binding of acyl glucuronides to serum albumin via an imine mechanism as revealed by tandem mass spectrometry. Proc. Natl. Acad. Sci. USA 90, 3797-3801 (1993).
37. P. C. Smith and J. H. Liu: Covalent binding of suprofen acyl glucuronide to albumin in vitro. Xenobiotica 23, 337-348 (1993).
38. C. Fenselau: Acyl glucuronides as chemically reactive intermediates. In "Conjugation-Deconjugation Reactions in Drug Metabolism and Toxicity" (F. C. Kauffman, ed.), vol. 112, pp. 367-390. Springer-Verlag, New York, 1994.
39. R. Wooster, L. Sutherland, T. E. Ebner, D. Clarke, O. Da Cruz, and B. Burchell: Cloning and stable expression of a new member of the human liver phenol/bilirubin UDP-glucuronosyltransferase cDNA family. Biochem. J. 278, 465-469 (1991).
40. O. H. Lowry, N. J. Rosebrough, A. L. Farr, and R. J. Randall: Protein measurement with the Folin phenol reagent. J. Biol. Chem. 193, 265-275 (1951).
41. F. D. Boudinot, C. A. Homon, W. J. Jusko, and H. W. Ruelius: Protein binding of oxazepam and its glucuronide conjugates to human albumin. Biochem. Pharmacol. 34, 2115-2121 (1985).
42. P. C. Smith, W. Q. Song, and R. J. Rodriguez: Covalent binding of etodolac acyl glucuronide to albumin in vitro. Drug Metab. Dispos. 20, 962-965 (1992).
43. J. A. Goldstein and S. M. F. De Morais: Biochemistry and molecular biology of the human CYP2C subfamily. Pharmacogenetics 4, 285-299 (1994).
44. A. Munafo, A. F. McDonagh, P. C. Smith, and L. Z. Benet: Irreversible binding of tolmetin glucuronic acid esters to albumin in vitro. Pharm. Res. 7, 21-27 (1990).
45. J. Roy-Chowdhury, A. W. Wolkoff, and I. M. Arias: Hereditary jaundice and disorders of bilirubin metabolism. In "The Metabolic Basis of Inherited Disease" (C. R. Scriver, A. L. Beaudet, W. S. Sly, D. Valle, eds.), pp. 1085-1094. McGraw-Hill, New York, 1989.
46. S. M. F. De Morais, J. P. Uetrecht, and P. G. Wells: Decreased glucuronidation and increased bioactivation of acetaminophen in Gilbert's syndrome. Gastroenterology 102, 577-586 (1992).
47. M. Patel, B. K. Tang, and W. Kalow: (S)-Oxazepam glucuronidation is inhibited by ketoprofen and other substrates of UGT2B7. Pharmacogenetics 5, 43-49 (1995).
48. R. T. McCluskey: Immunologically mediated tubulo-interstitial nephritis. In "Tubulointerstitial Nephropathies" (R. S. Cotran, ed.), vol. 10, pp. 121-149. Churchill Livingstone, New York, 1983.