Comparative metabolism of clenbuterol by rat and bovine liver microsomes and slices

Drug Metabolism and Disposition

Volumn 26, Issue 1, 1998, Pages 28-35

  Zalko, Daniel ^b   Perdu Durand, Elisabeth ^b   Debrauwer, Laurent ^b   Bec Ferte, Marie Pierre ^b   Tulliez, Jacques ^a  

^a CEMAGREF   (France)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

CLENBUTEROL; CYTOCHROME P450; FORMIC ACID; HIPPURIC ACID;

ANIMAL TISSUE; ARTICLE; BIOTRANSFORMATION; DRUG METABOLISM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIVER METABOLISM; LIVER MICROSOME; LIVER SLICE; MASS SPECTROMETRY; METABOLIC REGULATION; NONHUMAN; OXIDATION; PRIORITY JOURNAL; RAT; TARGET CELL;

ANIMALS; CATTLE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CLENBUTEROL; CULTURE MEDIA; LIVER; MALE; MICROSOMES, LIVER; RADIOACTIVITY; RATS; RATS, WISTAR; SUBCELLULAR FRACTIONS; TIME FACTORS; TRITIUM;

EID: 0031894852     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (35)

1. 14C]7-Ethoxycoumarin metabolism by precision-cut rat hepatic slices. Drug Metab Dispos 24:383-389.
2. Barrow A, Camp SJ, Dayal S, Jenner WN, Lashmar D, Oxford JM, Palmer E, Scully NL, Curtis GC, Hughes HM and Park GW (1995) Kinetics and disposition of picumeterol in animals. Xenobiotica 25:993-1007.
3. Beckett AH and Bélanger PM (1975) Metabolic incorporation of oxygen into primary and secondary aliphatic amines and the consequences in carbon-nitrogen bond cleavage. J Pharm Pharmacol 27:547-552.
4. Butler MA, Guengerich FP and Kadlubar FF (1989) Metabolic oxidation of the carcinogens 4-aminobiphenyl and 4,4′-methylene-bis(2-chloroaniline) by human hepatic microsomes and by purified rat hepatic cytochrome P-450 monooxygenases. Cancer Res 49:25-31.
5. Debrauwer L and Bories G (1992) Electrospray ionization mass spectrometry of some β-agonists. Rapid Commun Mass Spectrom 6:382-387.
6. Debrauwer L, Zalko D, Bories G and Tulliez J (1997) Electrospray ionization mass spectrometric study of N-oxidation products of clenbuterol. Rapid Commun Mass Spectrom 11:1089-1094.
7. Dogterom P (1993) Development of a simple incubation system for metabolism studies with precision-cut liver slices. Drug Metab Dispos 21:699-704.
8. Ekins S, Murray GI, Burke MD, Williams JA, Marchant NC and Hawksworth GM (1995) Quantitative differences in phase I and II metabolism between rat precision-cut liver slices and isolated hepatocytes. Drug Metab Dispos 23:1274-1279.
9. Fiems LO (1987) Effect of beta-adrenergic agonists in animal production and their mode of action. Ann Zootech 36:271-290.
10. Ford GP and Herman PS (1991) Conformational preferences and energetics of N-O heterolysis in aryl nitrenium ion precursors: ab initio and semiempirical molecular orbital calculations. J Chem Soc Perkin Trans 2:607-616.
11. a concept in the differentiation of enzymic N-oxidation, in Biological Oxidation of Nitrogen (Gorrod JW ed) pp 201-210, Elsevier/North-Holland Biomedical Press, Utrecht.
12. Gorrod JW and Manson D (1986) The metabolism of aromatic amines. Xenobiotica 16:933-955.
13. 2-stimulant. II. Urinary metabolites of mabuterol in rats and their pharmacological effects. Arzneim Forsch 34:1668-1679.
14. Kawalek JC and El Said KR (1994) Comparison of maturation of drug-metabolizing enzymes in calves with functioning or nonfunctioning rumen. Am J Vet Res 55:1579-1586.
15. Krumdieck CL, Dos Santos JE and Ho KJ (1980) A new instrument for the rapid preparation of tissue slices. Anal Biochem 104:118-123.
16. Leyssens L, Van Der Greef J, Penxten H, Czech J, Noben JP, Adriaensens P, Gelan J and Raus J (1993) Structure elucidation of unknown clenbuterol analogues detected in illegal preparations for animal use, in Proceedings of the Euroresidue II Conference (Haagsma N, Ruiter A, Czedik-Eysenberg PB eds), Utrecht, pp 444-449.
17. Lowry OH, Rosebrough NJ, Farr AL and Randall RJ (1951) Protein measurement with the Folin phenol reagent. J Biol Chem 193:265-275.
18. Martinez-Navarro JF (1990) Food poisoning related to consumption of illicit β-agonist in liver. Lancet 336:1311.
19. Meyer HHD and Rinke LM (1991) The pharmacokinetics and residues of clenbuterol in veal calves. J Anim Sci 69:4538-4544.
20. 14C]practolol metabolite(s) to mammalian liver microsomes. J Pharmacol Exp Ther 219:207-212.
21. Parrish AR, Gandolfi AJ and Brendel K (1995) Precision-cut tissue slices: applications in pharmacology and toxicology. Life Sci 57:1887-1901.
22. Perdu-Durand EF and Tulliez JE (1985) Hydrocarbon hydroxylation system in liver microsomes from four animal species. Food Chem Toxicol 23:363-366.
23. Pulce C, Lamaison D, Keck G, Bostvironnois C, Nicolas J, Descotes J, Mora M and Colmant A (1991) Intoxication alimentaire collective due à la présence de résidus de clenbuterol dans du foie de veau. Bull Epidémiol Hebd 5:17-18.
24. Sabbioni G and Wild D (1992) Quantitative structure-activity relationships of mutagenic aromatic and heteroaromatic azides and amines. Carcinogenesis (Lond) 13:709-713.
25. Saltron F, Berthoz Y, Rues R, Auguin N and Belhade L (1996) Structure elucidation of clenbuterol- and mabuterol-like compounds in complex matrices using silylated and n-butylboronate derivatives by gas chromatography/electron impact and chemical ionization mass spectrometry. J Mass Spectrom 31:810-818.
26. Sauer MJ, Graham PJ, Lake BG, Howells L and Coidham NG (1996) β-Agonist abuse in food producing animals: studies of in vitro liver metabolism to evaluate potential target residues, in Proceedings of the Euroresidue III Conference, pp 844-847.
27. Schmid J, Prox A, Zimmer A, Keck J and Kaschke S (1990) Biotransformation of clenbuterol. Fresenius J Anal Chem 337:121.
28. Smith MR and Gorrod JW (1978) The microsomal N-oxidation of some primary aromatic amines, in Biological Oxidation of Nitrogen (Gorrod JW ed) pp 65-70, Elsevier/North-Holland Biomedical Press.
29. Steensma A, Beamand JA, Walters DG, Price RJ and Lake BG (1994) Metabolism of coumann and 7-ethoxycoumarin by rat, mouse, guinea pig, cynomolgus monkey and human precision-cut liver slices. Xenobiotica 24:893-907.
30. Tanabe H, Kageyama H, Kubo J and Naruchi T (1984) Metabolic fate of clenbuterol (NAB 365). III. Metabolism in rats and dogs. Iyakuhin Kenkyu 15:467-476.
31. Testa B (1995) Monooxygenase-catalyzed nitrogen oxidations, in Biochemistry of Redox Reactions (Testa B and Caldwell J eds) pp 164-202, Academic Press, New York.
32. Uetrecht JP (1984) Reactivity and possible significance of hydroxylamine and nitroso metabolites of procainamide. J Pharmacol Exp Ther 232:207-212.
33. Uetrecht JP, Sweetman BJ, Woosley RL and Oates JA (1984) Metabolism of procainamide to a hydroxylamine by rat and human hepatic microsomes. Drug Metab Dispos 12:77-81.
34. 3H-clenbuterol in the rat and bovine, in Proceedings of the Euroresidue III Conference, pp 993-997.
35. Zalko D, Debrauwer L, Bories G and Tulliez J (1997) Evidence for a new and major metabolic pathway of clenbuterol involving in vivo formation of a N-hydroxyarylamine. Chem Res Toxicol 10:197-204.