Disposition and chemical stability of telmisartan 1-O-acylglucuronide

Drug Metabolism and Disposition

Volumn 27, Issue 10, 1999, Pages 1143-1149

  Ebner, T ^a   Heinzel, G ^a   Prox, A ^a   Beschke, K ^a   Wachsmuth, H ^a  

^a BOEHRINGER INGELHEIM PHARMA GMBH AND CO KG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

DICLOFENAC 1 O ACYLGLUCURONIDE; DICLOFENAC DERIVATIVE; DRUG METABOLITE; TELMISARTAN; TELMISARTAN 1 O ACYLGLUCURONIDE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; AQUEOUS SOLUTION; ARTICLE; COVALENT BOND; DRUG CLEARANCE; DRUG DEGRADATION; DRUG DISPOSITION; DRUG HALF LIFE; DRUG HYDROLYSIS; DRUG STABILITY; DRUG STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INTRAVENOUS DRUG ADMINISTRATION; ISOMERISM; MALE; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RAT;

ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; ANIMALS; BENZIMIDAZOLES; BENZOATES; DICLOFENAC; DRUG STABILITY; GLUCURONIDES; MALE; PROTEIN BINDING; RATS; RATS, WISTAR; SERUM ALBUMIN;

EID: 0032826052     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (28)

1. Banks AT, Zimmermann HJ, Ishak KG and Harter JG (1997) Diclofenac-associated hepatotoxicity: Analysis of 180 cases reported to the food and drug administration as adverse reactions. Hepatology 21:820-827.
2. Barber ED, Fox JA and Giordano CJ (1994) Hydrolysis, absorption and metabolism of di(2-ethylhexyl) terephtalate in the rat. Xenobiotica 24:441-450.
3. Benet LZ, Spahn-Langguth H, Iwakawa S, Volland C, Mizuma T, Mayer S, Mutschler E and Lin ET (1993) Predictability of the covalent binding of acidic drugs in man. Life Sci 53:141-146.
4. Bischer A, Zia-Amirhosseini P, Iwaki M, McDonagh AF and Benet LZ (1995) Stereoselective binding properties of naproxen glucuronide diastereomers to protein. J Pharmacokinet Biopharm 23:379-395.
5. Castillo M and Smith PC (1995) Disposition and reactivity of ibuprofen and ibufenac acyl glucuronides in vivo in the rhesus monkey and in vitro with human serum albumin. Drug Metab Dispos 5:566-572.
6. Ding A. Ojingwa JC, McDonagh AF, Burlingame AL and Benet LZ (1993) 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.
7. Fenselau C (1994) Acyl glucuronides as chemically reactive intermediates, in Conjugation-Deconjugation Reactions in Drug Metabolism and Toxicity (Kauffman FC ed) pp 367-389, Springer-Verlag, Berlin.
8. Gillette JR (1974) A perspective on the role of chemically reactive metabolites of foreign compounds in toxicity - I. Correlation of changes in covalent binding of reactivity metabolites with changes in the incidence and severity of toxicity. Biochem Pharmacol 23:2785-2794.
9. Grubb N, Weil A and Caldwell J (1993) Studies on the in vitro reactivity of clofibryl and fenofibryl glucuronides - Evidence for protein binding via a Schiff's base mechanism. Biochem Pharmacol 46:357-364.
10. Hargus SJ, Amouzedeh HR, Pumford NR, Myers TG, McCoy SC and Pohl LR (1994) Metabolic activation and immunochemical localization of liver protein adducts of the nonsteroidal anti-inflammatory drug diclofenac. Chem Res Toxicol 7:575-582.
11. Hayball PJ (1995) Formation and reactivity of acyl glucuronides. Chirality 7:1-9.
12. Heinzel G, Woloszczak R, Thomann P (1993) TopFit 2.0. Pharmacokinetic and Pharmacodynamic Data Analysis System for the PC. Gustav Fischer Verlag, Stuttgart.
13. Hyneck ML, Smith PC, Munafo A, McDonagh AF and Beret LZ (1988) Disposition and irreversible plasma protein binding of tolmetin in humans. Clin Pharmacokinet 44:107-114.
14. Kretz-Rommel A and Boelsterli UA (1994a) Mechanism of covalent adduct formation of diclofenac to rat hepatic microsomal proteins. Retention of the glucuronic acid moiety in the adduct. Drug Metab Dispos 22:956-961.
15. Kretz-Rommel A and Boelsterli UA (1994b) Selective protein adducts to membrane proteins in cultured rat hepatocytes exposed to diclofenac: Radiochemical and immunochemical analysis. Mol Pharmacol 45:237-244.
16. Kretz-Rommel A and Boelsterli UA (1995) Cytotoxic activity of T cells and non-T cells from diclofenac-immunized mice against cultured syngeneic hepatocytes exposed to diclofenac. Hepatology 22 (Suppl 1):213-222.
17. Kuo GY and Dulik DM (1995) Utility of trace trifluoroacetic acid to enhance the quality of proton NMR spectra of xenobiotic metabolites. Drug Metab Dispos 23:1004-1006.
18. Lenz EM, Greatbanks D, Wilson ID, Spraul M, Hofmann M, Troke J, Lindon JC and Nicholson JK (1996) Direct characterization of drug glucuronide isomers in human urine by HPLC-NMR spectroscopy: Application to the positional isomers of 6,11-dihydro-11-oxodibenz[b, e]oxepin-2-acetic acid glucuronide. Anal Chem 68:2832-2837.
19. Liu J-H, Malone RS, Stallings H and Smith PC (1996) Influence of renal failure in rats on the disposition of salicyl acyl glucuronide and covalent binding of salicylate to plasma proteins. J Pharmacol Exp Ther 278:277-283.
20. McGurk K, Remmel RP, Hosagrahara VP, Tosh D and Burchell B (1996) Reactivity of mefenamic acid 1-O-acyl glucuronide with proteins in vitro and ex vivo. Drug Metab Dispos 24:842-849.
21. Roth W, Beschke K, Jauch R, Zimmer A and Koss FW (1981) Fully automated high-performance liquid chromatography. A new chromatograph for pharmacokinetic drug monitoring by direct injection of body fluids. J Chromatogr 222:13-22.
22. Salama A, Kroll H, Wittmann G and Mueller-Eckhardt C (1996) Diclofenac-induced immune haemolytic anaemia: Simultaneous occurrence of red blood cell autoantibodies and drug-dependent antibodies. Br J Haematol 95:640-644.
23. Sallustio BC and Foster DJR (1995) Reactivity of gemfibrozil 1-O-β-acyl-glucuronide. Pharmacokinetics of covalently bound gemfibrozil-protein adducts in rats. Drug Metab Dispos 23:892-899.
24. Schmid J, Beschke K, Prox P, Ebner T, Busch U, Koebe HG, Pahernik S and Schildberg FW (1996) In vivo and in vitro biotransformation of telmisartan, human hepatocyte cultures as an aid in human metabolic studies. Exp Toxicol Pathol 48:387.
25. Sidelmann UG, Gavaghan C, Carless HAJ, Farrant RD, Lindon JC, Wilson ID and Nicholson JK (1995) Identification of the positional isomers of 2-fluorobenzoic acid 1-O-acyl glucuronide by directly coupled HPLC-NMR. Anal Chem 67:3401-3404.
26. 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.
27. Tanaka Y and Suzuki A (1994) Enzymatic hydrolysis of zenarestat 1-O-acylglucuronide. J Pharm Pharmacol 46:235-239.
28. Williams AM and Dickinson RG (1994) Studies on the reactivity of acyl glucuronides - VI. Modulation of reversible and covalent interaction of diflunisal acyl glucuronide and its isomers with human plasma protein in vitro. Biochem Pharmacol 47:457-467.