The metabolism and toxicity of furosemide in the wistar rat and CD-1 mouse: A chemical and biochemical definition of the toxicophore

Journal of Pharmacology and Experimental Therapeutics

Volumn 322, Issue 3, 2007, Pages 1208-1220

  Williams, Dominic P ^a   Antoine, Daniel J ^a   Butler, Philip J ^b   Jones, Russell ^b   Randle, Laura ^a   Payne, Anthony ^b   Howard, Martin ^b   Gardner, Iain ^b   Blagg, Julian ^c   Park, B Kevin ^a  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

^c Cyprotex ^*  (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1 AMINOBENZOTRIAZOLE; CARBOXYLIC ACID DERIVATIVE; FURAN; FUROSEMIDE; GLUCURONIDE; GLUTATHIONE; LIVER PROTEIN;

ANIMAL EXPERIMENT; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; COVALENT BOND; DRUG MECHANISM; DRUG METABOLISM; DRUG PROTEIN BINDING; LIVER CELL; LIVER TOXICITY; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTEIN DEPLETION; RAT;

ANIMALS; CELLS, CULTURED; CYTOCHROME P-450 ENZYME SYSTEM; FUROSEMIDE; GLUTATHIONE; HEPATOCYTES; MICE; MICROSOMES, LIVER; PROTEIN BINDING; RATS; RATS, WISTAR; SPECIES SPECIFICITY;

EID: 34548103826     PISSN: 00223565     EISSN: 15210103     Source Type: Journal    
DOI: 10.1124/jpet.107.125302     Document Type: Article

References (35)

1. Baer BR, Rettie AE, and Henne KR (2005) Bioactivation of 4-ipomeanol by CYP4B1: adduct characterization and evidence for an enedial intermediate. Chem Res Toxicol 18:855-864.
2. Beermann B, Dalen E, and Lindstrom B (1977) Elimination of furosemide in healthy subjects and in those with renal failure. Clin Pharmacol Ther 22:70-78.
3. Beermann B, Dalen E, Lindstrom B, and Rosen A (1975) On the fate of furosemide in man. Eur J Clin Pharmacol 9:51-61.
4. Benet LZ (1979) Pharmacokinetics/pharmacodynamics of furosemide in man: a review. J Pharmacokinet Biopharm 7:1-27.
5. Bolze S, Bromet N, Gay-Feutry C, Massiere F, Boulieu R, and Hulot T (2002) Development of an in vitro screening model for the biosynthesis of acyl glucuronide metabolites and the assessment of their reactivity toward human serum albumin. Drug Metab Dispos 30:404-413.
6. Boocock DJ, Maggs JL, Brown K, White INH, and Park BK (2000) Major interspecies differences in the rates of O-sulphonation and O-glucuronylation of alpha-hydroxytamoxifen in vitro: a metabolic disparity protecting human liver from the formation of tamoxifen-DNA adducts. Carcinogenesis 21:1851-1858.
7. Dargie HJ and Dollery CT (1975) Adverse reactions to diuretic drugs, in Meyler's Side Effects of Drugs (Dukes MNG ed) p 483, Exerpta Medica, Amsterdam, The Netherlands.
8. Druckova A and Marnett LJ (2006) Characterization of the amino acid adducts of the enedial derivative of teucrin A. Chem Res Toxicol 19:1330-1340.
9. Goldring CE, Kitteringham NR, Elsby R, Randle LE, Clement YN, Williams DP, McMahon M, Hayes JD, Itoh K, Yamamoto M, et al. (2004) Activation of hepatic Nrf2 in vivo by acetaminophen in CD-1 mice. Hepatology 39:1267-1276.
10. Grewal KK, Rafeiro E, and Racz WJ (1996) Bromobenzene and furosemide hepatotoxicity: alterations in glutathione, protein thiols, and calcium. Can J Physiol Pharmacol 74:257-264.
11. Hammarlund-Udenaes M and Benet LZ (1989) Furosemide pharmacokinetics and pharmacodynamics in health and disease-an update. J Pharmacokinet Biopharm 17:1-46.
12. Kerremans AL, Tan Y, Van Ginneken CA, and Gribnau FW (1982) Specimen handling and high-performance liquid chromatographic determination of furosemide. J Chromatogr 229:129-139.
13. Liu J, Liu Y, Parkinson A, and Klaassen CD (1995) Effect of oleanolic acid on hepatic toxicant-activating and detoxifying systems in mice. J Pharmacol Exp Ther 275: 768-774.
14. Madden S, Maggs JL, and Park BK (1996) Bioactivation of carbamazepine in the rat in vivo: evidence for the formation of reactive arene oxide(s). Drug Metab Dispos 24:469-479.
15. Maggs JL, Williams D, Pirmohamed M, and Park BK (1995) The metabolic formation of reactive intermediates from clozapine, a drug associated with agranulocytosis in man. J Pharmacol Exp Ther 275:1463-1475.
16. Massey TE, Walker RM, McElligott TF, and Racz WJ (1987) Furosemide toxicity in isolated mouse hepatocyte suspensions. Toxicology 43:149-160.
17. Mitchell JR, Jollow DJ, Potter WZ, Davis DC, Gillette JR, and Brodie BB (1973) Acetaminophen-induced hepatic necrosis: I. Role of drug metabolism. J Pharmacol Exp Ther 187:185-194.
18. Mitchell JR, Potter WZ, Hinson JA, and Jollow DJ (1974) Hepatic necrosis caused by furosemide. Nature 251:508-511.
19. Mitchell JR, Snodgrass WR, and Gillette JR (1976) The role of biotransformation in chemical-induced liver injury. Environ Health Perspect 15:27-38.
20. Mizuma T, Benet LZ, and Lin ET (1998) High-performance liquid chromatographic determination and identification of acyl migration and photodegradation products of furosemide 1-O-acyl glucuronide. J Chromatogr B Biomed Sci Appl 718:153-162.
21. Noce R, Paredes BE, Pichler WJ, and Krahenbuhl S (2000) Acute generalized exanthematic pustulosis (AGEP) in a patient treated with furosemide. Am J Med Sci 320:331-333.
22. Owens CW and Belcher RV (1965) A colorimetric micro-method for the determination of glutathione. Biochem J 94:705-711.
23. Perez J, Sitar DS, and Ogilvie RI (1979) Biotransformation of furosemide in patients with acute pulmonary edema. Drug Metab Dispos 7:383-387.
24. Pirmohamed M, Williams D, Madden S, Templeton E, and Park BK (1995a) Metabolism and bioactivation of clozapine by human liver in vitro. J Pharmacol Exp Ther 272:984-990.
25. Pirmohamed M, Williams DP, Madden S, Templeton E, and Park BK (1995b) Metabolism and bioactivation of clozapine by human liver in vitro. J Pharmacol Exp Ther 272:984-990.
26. Ponto LL and Schoenwald RD (1990) Furosemide (frusemide): I. A pharmacokinetic/ pharmacodynamic review. Clin Pharmacokinet 18:381-408.
27. Rachmel A, Hazelton GA, Yergey AL, and Liberato DJ (1985) Furosemide 1-O-acyl glucuronide: in vitro biosynthesis and pH-dependent isomerization to betaglucuronidase-resistant forms. Drug Metab Dispos 13:705-710.
28. Seglen PO (1976) Preparation of isolated rat liver cells. Methods Cell Biol 13:29-83.
29. Smith DE and Benet LZ (1983) Biotransformation of furosemide in kidney transplant patients. Eur J Clin Pharmacol 24:787-790.
30. Smith DE, Lin ET, and Benet LZ (1980) Absorption and disposition of furosemide in healthy volunteers, measured with a metabolite-specific assay. Drug Metab Dispos 8:337-342.
31. Takagi S, Takayama S, and Onodera T (1991) Hepatotoxicity of DR-3438, tienilic acid, indacrinone and furosemide studied in vitro. Toxicol Lett 55:287-293.
32. Uetrecht J (2001) Prediction of a new drug's potential to cause idiosyncratic reactions. Curr Opin Drug Discov Dev 4:55-59.
33. Vandeputte C, Guizon I, Genestie-Denis I, Vannier B, and Lorenzon G (1994) A microtiter plate assay for total glutathione and glutathione disulfide contents in cultured/isolated cells: performance study of a new miniaturized protocol. Cell Biol Toxicol 10:415-421.
34. Wirth PJ, Bettis CJ, and Nelson WL (1976) Microsomal metabolism of furosemide evidence for the nature of the reactive intermediate involved in covalent binding. Mol Pharmacol 12:759-768.
35. Wong SG, Card JW, and Racz WJ (2000) The role of mitochondrial injury in bromobenzene and furosemide induced hepatotoxicity. Toxicol Lett 116:171-181.