Identification of zomepirac-S-acyl-glutathione in vitro in incubations with rat hepatocytes and in vivo in rat bile

Drug Metabolism and Disposition

Volumn 31, Issue 11, 2003, Pages 1429-1436

  Grillo, Mark P ^a,b   Hua, Fengmei ^a  

^a PFIZER INC   (United States)

^b MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG DERIVATIVE; DRUG METABOLITE; GLUTATHIONE; TOLMETIN; UNCLASSIFIED DRUG; ZOMEPIRAC; ZOMEPIRAC S ACYL GLUTATHIONE;

ANIMAL; ANIMAL EXPERIMENT; ARTICLE; BILE; CHEMISTRY; DRUG ACTIVATION; DRUG HALF LIFE; DRUG HYDROLYSIS; DRUG STABILITY; LIQUID CHROMATOGRAPHY; LIVER CELL; MALE; METABOLISM; NONHUMAN; PRIORITY JOURNAL; RAT; RAT STRAIN; TANDEM MASS SPECTROMETRY;

ANIMALS; BILE; GLUTATHIONE; HEPATOCYTES; MALE; RATS; RATS, SPRAGUE-DAWLEY; TOLMETIN;

ANIMALIA;

EID: 0142150004     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: 10.1124/dmd.31.11.1429     Document Type: Article

References (30)

1. Bailey MJ and Dickinson RG (1996) Chemical and immunochemical comparison of protein adduct formation of four carboxylate drugs in rat liver and plasma. Chem Res Toxicol 9:659-666.
2. Bakke OM, Manocchia M, de Abajo F, Kaitin KI, and Lasagna L (1995) Drug safety discontinuations in the United Kingdom, the United States and Spain from 1974 to 1993, a regulatory perspective. Clin Pharmacol Ther 58:108-117.
3. Benet LZ, Spahn-Langguth H, Iwakawa S, Volland C, Misuma T, Mayer S, Mutschler E, and Lin ET (1993) Predictability of covalent binding of acidic drugs in man. Life Sci 53:PL141-PL146.
4. Boelsterli U (2002) Xenobiotic acyl glucuronides and acyl-CoA thioesters as protein-reactive metabolites with the potential to cause idiosyncratic drug reactions. Curr Drug Metab 3:439-450.
5. Dietze EC, Grillo MP, Kalhorn T, Nieslanik BS, Jochheim CM, and Atkins WM (1998) Thiol ester hydrolysis catalyzed by glutathione S-transferase A1-1. Biochemistry 37:14948-14957.
6. Faed EM (1984) Properties of acyl glucuronides: implications for studies of the pharmacokinetics and metabolism of acidic drugs. Drug Metab Rev 15:1213-1249.
7. Grillo MP and Benet LZ (2001) Interaction of γ -glutamyltranspeptidase with cloribryl-S-acyl-glutathione in vitro and in vivo in rat. Chem Res Toxicol 14:1033-1040.
8. Grillo MP and Benet LZ (2002) Studies on the reactivity of clofibryl-S-acyl-CoA thioester with glutathione in vitro. Drug Metab Dispos 30:55-62.
9. Hasegawa J, Smith PC, and Benet LZ (1982) Apparent intramolecular acyl migration of zomepirac glucuronide. Drug Metab Dispos 10:469-473.
10. Hinchman CA and Ballatori N (1990) Glutathione-degrading capacities of liver and kidney in different species. Biochem Pharmacol 40:1131-1135.
11. Kiani R and Kushner M (1983) Zomepirac-induced serum sickness. A report of two cases. JAMA (J Am Med Assoc) 249:2812-2813.
12. Levy DB and Vasilomanolakis EC (1984) Anaphylactic reactions due to zomepirac. Drug Intell Clin Pharm 18:983-984.
13. Li C, Benet LZ, and Grillo MP (2002a) Studies on the chemical reactivity of 2-phenylpropionic acid 1-O-acyl glucuronide and S-acyl-CoA thioester metabolites. Chem Res Toxicol 15:1309-1317.
14. Li C, Benet LZ, and Grillo MP (2002b) Enantioselective covalent binding of 2-phenylpropionic acid to protein in vitro in rat hepatocytes. Chem Res Toxicol 15: 1480-1487.
15. Moldéus P, Hogberg J, and Orrenius S (1978) Isolation and use of liver cells. Methods Enzymol 52:60-71.
16. Nakagawa Y and Moldéus P (1998) Mechanism of p-hydroxybenzoate ester-induced mitochondrial dysfunction and cytotoxicity in isolated rat hepatocytes. Biochem Pharmacol 55:1907-1914.
17. Olsen J (2002) Reactive Metabolites: Formation, Metabolism and Reactivity of acyl Coenzyme A Thioesters in Vitro and in Vivo. Ph.D. thesis, The Royal Danish School of Pharmacy, Copenhagen, Denmark.
18. O'Neill PJ, Yorgey KA, Renzi NL, Williams RL, and Benet LZ (1982) Disposition of zomepirac sodium in man. J Clin Pharmacol 22:470-476.
19. Shore U, Fenselau C, King AR, and Dickinson RG (1995) Characterization and formation of the glutathione conjugate of clofibric acid. Drug Metab Dispos 23:119-123.
20. Smith PC, Benet LZ, and McDonagh AF (1990) Covalent binding of zomepirac glucuronide to proteins: evidence for a Schiff base mechanism. Drug Metab Dispos 18:639-644.
21. Smith PC, Hasegawa J, Langendijk PNJ, and Benet LZ (1985) Stability of acyl glucuronides in blood, plasma and urine: studies with zomepirac. Drug Metab Dispos 13:110-112.
22. Smith PC, McDonagh AF, and Benet LZ (1986) Irreversible binding of zomepirac to plasma protein in vitro and in vivo. J Clin Investig 77:934-939.
23. Spahn-Langguth H and Benet LZ (1992) Acyl glucuronides revisited: is the glucuronidation process a toxification as well as a detoxification mechanism? Drug Metab Rev 24:5-48.
24. Spahn-Langguth H, Benet LZ, Zia-Amirhosseini P, Iwakawa H, and Langguth P (1997) Kinetics of reactive phase II metabolites: stereochemical aspects of formation of epimeric acyl glucuronides and their reactivity. The impact of stereochemistry on drug development and use. Chem Anal Ser Monogr Anal Chem Appl 142:125-170.
25. Stogniew M and Fenselau C (1982) Electrophilic reactions of acyl-linked glucuronides. Drug Metab Dispos 10:609-613.
26. Tate SS (1975) Interaction of γ-glutamyltranspeptidase with S-acyl derivatives of glutathione. FEBS Lett 54:319-322.
27. Wang M and Dickinson RG (2000) Bile duct ligation promotes covalent drug-protein adduct formation in plasma but not in liver of rats given zomepirac. Life Sci 68:525-537.
28. Wang M, Gorrell MD, McCaughan GW, and Dickinson RG (2001) Dipeptidyl peptidase IV is a target for covalent adduct formation with the acyl glucuronide metabolite of the antiinflammatory drug zomepirac. Life Sci 68:785-797.
29. Zia-Amirhosseini P, Harris RZ, Brodsky FM, and Benet LZ (1995) Hypersensitivity to nonsteroidal anti-inflammatory drugs. Nat Med 1:2-4.
30. Zimmerman HJ (1994) Hepatic injury associated with nonsteroidal anti-inflammatory drugs, in Nonsteroidal Antiinflammatory Drugs. Mechanisms and Clinical Use (Lewis AJ and Furst DE eds) pp 171-194, Marcel Dekker Inc., New York.