Disposition of gemfibrozil and gemfibrozil acyl glucuronide in the rat isolated perfused liver

Drug Metabolism and Disposition

Volumn 24, Issue 9, 1996, Pages 984-989

  Sallustio, Benedetta C ^a,b   Fairchild, Barbara A ^a   Shanahan, Kathryn ^c   Evans, Allan M ^c   Nation, Roger L ^c  

^a QUEEN ELIZABETH HOSPITAL   (Australia)

^b UNIVERSITY OF ADELAIDE   (Australia)

^c UNIVERSITY OF SOUTH AUSTRALIA   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG METABOLITE; GEMFIBROZIL; GLUCURONIDE;

ANIMAL TISSUE; ARTICLE; DRUG DISPOSITION; DRUG EXCRETION; DRUG HYDROLYSIS; DRUG METABOLISM; DRUG TRANSFORMATION; DRUG UPTAKE; ISOLATED LIVER; LIVER METABOLISM; MALE; NONHUMAN; PRIORITY JOURNAL; RAT;

ANIMALS; ANTILIPEMIC AGENTS; BILE; GEMFIBROZIL; GLUCURONATES; KINETICS; LIVER; MALE; PERFUSION; RATS; RATS, SPRAGUE-DAWLEY;

ANIMALIA;

EID: 0029841891     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (39)

1. J. M. Hawkins, W. E. Jones, F. W. Bonner, and G. G. Gibson: The effect of peroxisome proliferators on microsomal, peroxisomal, and mitochondrial enzyme activities in the liver and kidney. Drug Metab. Rev. 18, 441-551 (1987).
2. A. Steiner, B. Weisser, and W. Vetter: A comparative review of the adverse effects of treatments for hyperlipidaemia. Drug Safety 6, 118-130 (1991).
3. P. P. Michielsen, H. Fierens, and Y. M. Van Maercke: Drug-induced gallbladder disease. Incidence, aetiology and management. Drug Safety 7, 32-45 (1992).
4. M. N. Cayen: Metabolism and pharmacokinetics of antihyperlipidaemic agents. Prog. Drug Metab. 7, 173-227 (1983).
5. H. Spahn-Langguth and L. Z. Benet: Acyl glucuronides revisited: is the glucuronidation process a toxification as well as a detoxification mechanism? Drug Metab. Rev. 24, 5-47 (1992).
6. 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 in vitro. Xenobiotica 24, 495-506 (1994).
7. S. J. Hargus, H. R. Amouzedeh, N. R. Pumford, T. G. Myers, S. C. McCoy, and L. R. Pohl: Metabolic activation and immunochemical localization of liver protein adducts of the nonsteroidal anti-inflammatory drug diclofenac. Chem. Res. Toxicol. 7, 575-582 (1994).
8. H. Knauf, E. U. Kolle, and E. Mutschler: Gemfibrozil absorption and elimination in kidney and liver disease. Klin. Wochenschr. 68, 692-698 (1990).
9. A. Nakagawa, A. Shigeta, H. Iwabuchi, M. Horiguchi, K. Nakamura, and H. Takahagi: Simultaneous determination of gemfibrozil and its metabolites in plasma by a fully automated high performance liquid chromatographic system. Biomed. Chromatogr. 5, 68-73 (1991).
10. C. G. Curtis, T. M. Danaher, E. A. Hibbert, C. L. Morris, A. M. Scott, B. A. Woolcott, and G. M. Powell: The fate of gemfibrozil and its metabolites in the rat. Biochem. Soc. Trans. 13, 1190-1191 (1985).
11. B. C. Sallustio, B. A. Fairchild, and P. Pannell: Interaction of human serum albumin with the electrophilic metabolite 1-O-gemfibrozil-β-D-glucuronide. Drug Metab. Dispos., submitted for publication.
12. B. C. Sallustio and D. J. R. Foster: Reactivity of gemfibrozil 1-O-β-acyl glucuronide. Pharmacokinetics of covalently bound gemfibrozil-protein adducts in rats. Drug Metab. Dispos. 23, 892-899 (1995).
13. S. D. Nelson and P. G. Pearson: Covalent and non-covalent interactions in acute lethal cell injury caused by chemicals. Annu. Rev. Pharmacol. Toxicol. 30, 169-195 (1990).
14. B. C. Sallustio and B. A. Fairchild: Biosynthesis, characterization and direct high-performance liquid chromatographic analysis of gemfibrozil 1-O-β-acylglucuronide. J. Chromatogr. 665, 345-353 (1995).
15. A. M. Evans and K. Shanahan: The disposition of morphine and its metabolites in the in-situ rat isolated perfused liver. J. Pharm. Pharmacol. 47, 333-339 (1995).
16. F. Lapicque, N. Muller, E. Payan, N. Dubois, and P. Netter: Protein binding and stereoselectivity of nonsteroidal anti-inflammatory drugs. Clin. Pharmacokinet. 25, 115-125 (1993).
17. J. C. Ojingwa, H. Spahn-Langguth, and L. Z. Benet: Reversible binding of tolmetin, zomepirac, and their glucuronide conjugates to human serum albumin and plasma. J. Pharmacokinet. Biopharm. 22, 19-40 (1994).
18. S. Iwakawa, H. Spahn, L. Z. Benet, and E. T. Lin: Stereoselective binding of the glucuronide conjugates of carprofen enantiomers to human serum albumin. Biochem. Pharmacol. 39, 949-953 (1990).
19. P. J. Hayball, R. L. Nation, and F. Bochner: Stereoselective interactions of ketoprofen glucuronides with human plasma protein and serum albumin. Biochem. Pharmacol. 44, 291-299 (1992).
20. A. Bischer, M. Iwaki, P. Zia-Amirhosseini, and L. Z. Benet: Stereoselective reversible binding properties of the glucuronide conjugates of fenoprofen enantiomers to human serum albumin. Drug Metab. Dispos. 23, 900-903 (1995).
21. A. M. Williams and R. G. Dickinson: Studies on the reactivity of acyl glucuronides. VI. Modulation of reversible and covalent interactions of diflunisal acyl glucuronide and its isomers with human plasma protein in vitro. Biochem. Pharmacol. 47, 457-467 (1994).
22. T. Gessner and N. Hamada: High biliary and systemic excretion of a glucuronide during its hepatic synthesis. Life Sci. 15, 83-93 (1974).
23. A. M. Evans and K. Shanahan: Biliary excretion of hepatically-generated and pre-formed morphine-3-glucuronide (M-3-G) in the isolated perfused rat liver: evidence for a diffusional barrier. Clin. Exp. Pharmacol. Physiol. Suppl. 1, 22 (1993).
24. N. Dubois, F. Lapicque, M.-H. 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, 617-623 (1993).
25. H. W. Ruelius, S. K. Kirkman, E. M. Young, and F. W. Janssen: Reactions of oxaprozin-1-O-acyl glucuronide in solutions of human plasma and albumin. Adv. Exp. Med. Biol. 197, 431-441 (1986).
26. C. Volland, H. Sun, J. Dammeyer, and L. Z. Benet: Stereoselective degradation of the fenoprofen acyl glucuronide enantiomers and irreversible binding to plasma protein. Drug Metab. Dispos. 19, 1080-1086 (1991).
27. 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).
28. R. G. Dickinson, P. V. Baker, and A. R. King: Studies on the reactivity of acyl glucuronides. VII. Salicyl acyl glucuronide reactivity in vitro and covalent binding of salicylic acid to plasma protein of humans taking aspirin. Biochem. Pharmacol. 47, 469-476 (1994).
29. A. R. King and R. G. Dickinson: Studies on the reactivity of acyl glucuronides. I. Phenolic glucuronidation of isomers of diflunisal acyl glucuronide in the rat. Biochem. Pharmacol. 42, 2289-2299 (1991).
30. M. Iwaki, A. Bischer, A. C. Nguyen, A. F. McDonagh, and L. Z. Benet: Stereoselective disposition of naproxen glucuronide in the rat. Drug Metab. Dispos. 23, 1099-1103 (1995).
31. B. J. Rowe and P. J. Meffin: Diisopropylfluorophosphate increases clofibric acid clearance: supporting evidence for a futile cycle. J. Pharmacol. Exp. Ther. 230, 237-241 (1984).
32. P. C. Smith, A. F. McDonagh, and L. Z. Benet: Effect of esterase inhibition on the disposition of zomepirac glucuronide and its covalent binding to plasma proteins in the guinea pig. J. Pharmacol. Exp. Ther. 252, 218-224 (1990).
33. H. Spahn-Langguth and L. Z. Benet: Microsomal acyl glucuronidation: enzyme-kinetic studies with labile glucuronides. Pharmacology 46, 268-273 (1993).
34. C. Tiribelli: Determinants in the hepatic uptake of organic anions. J. Hepatol. 14, 385-390 (1992).
35. I. M. Arias: The biology of the bile canaliculus. Hepatology 17, 318-329 (1993).
36. P. Zimniak and Y. G. Awasthi: ATP-dependent transport systems for organic anions. Hepatology 17, 330-339 (1993).
37. G. Jedlitschki, I. Leiner, M. Bohme, U. Buchholz, J. Bar-Tana, and D. Keppler: Hepatobiliary elimination of the peroxisome proliferator nafenopin by conjugation and subsequent ATP-dependent transport across the canalicular membrane. Biochem. Pharmacol. 48, 1113-1120 (1994).
38. 14C]hydratropic acid and its variation with species. Xenobiotica 7, 707-715 (1977).
39. J. R. Baldwin, D. T. Witiak, and D. R. Feller: Disposition of clofibrate in the rat. Acute and chronic administration. Biochem. Pharmacol. 29, 3143-3154 (1980).