Structural elucidation of phase i and II metabolites of bupivacaine in horse urine and fungi of the Cunninghamella species using liquid chromatography/multi-stage mass spectrometry

Rapid Communications in Mass Spectrometry

Volumn 26, Issue 11, 2012, Pages 1338-1346

  Rydevik, Axel ^a   Bondesson, Ulf ^a,b   Hedeland, Mikael ^a,b  

^a UPPSALA UNIVERSITY   (Sweden)

^b NATIONAL VETERINARY INSTITUTE   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

BIODEGRADATION; BIOMOLECULES; BODY FLUIDS; ELECTROSPRAY IONIZATION; FUNGI; HIGH PRESSURE LIQUID CHROMATOGRAPHY; ION EXCHANGE; MAMMALS; MASS SPECTROMETRY; METABOLISM; PHYSIOLOGY;

BUPIVACAINE; DOPING CONTROL; ELEGANS; HORSE URINE; IN-VITRO; LOCAL ANAESTHETIC; MULTI-STAGE MASS SPECTROMETRY; PHASE I; PHASE II; STRUCTURAL ELUCIDATION;

METABOLITES;

EID: 84860653229     PISSN: 09514198     EISSN: 10970231     Source Type: Journal    
DOI: 10.1002/rcm.6225     Document Type: Article

References (24)

1. S. C. Sweetman, in Martindale: The Complete Drug Reference, (37th edn.), (Ed:, S.C. Sweetman,). Pharmaceutical Press, London, 2011.
2. J. D. Harkins, A. Lehner, W. Karpiesiuk, W. E. Woods, L. Dirikolu, J. Boyles, W. G. Carter, T. Tobin,. Bupivacaine in the horse: relationship of local anesthetic responses and urinary concentrations of 3-hydroxybupivacaine. J. Vet. Pharmacol. Ther. 1999, 22, 181.
3. http://www.fass.se/LIF/produktfakta/substance-products.jsp?substanceId= IDE4POCPU9PXOVERT1 (accessed 2011-12-15)
4. B. Bruguerolle,. Oxidative metabolism of bupivacaine into pipecolylxylidine in humans is mainly catalyzed by CYP3A. Drug Metab. Dispos. 2000, 28, 383.
5. J. P. Fawcett, J. Kennedy, A. Kumar, R. Ledger, M. Zacharias,. Stereoselective urinary excretion of bupivacaine and its metabolites during epidural infusion. Chirality 1999, 11, 50.
6. R. Ledger,. Nonaromatic hydroxylation of bupivacaine during continuous epidural infusion in man. J. Biochem. Biophys. Methods 2003, 57, 105.
7. F. Reynolds,. Metabolism and excretion of bupivacaine in man. A comparison with mepivacaine. Brit. J. Anaesth. 1971, 43, 33.
8. J. Caldwell, L. J. Notarianni, R. L. Smith, W. Snedden,. The metabolism of bupivacaine in the rat. Br. J. Pharmacol. 1977, 61, 135P.
9. T. J. Goehl, J. B. Davenport, M. J. Stanley,. Distribution, biotransformation, and excretion of bupivacaine in rat and monkey. Xenobiotica 1973, 3, 761.
10. R. M. Krisko, M. A. Schieferecke, T. D. Williams, C. E. Lunte,. Determination of bupivacaine and metabolites in rat urine using capillary electrophoresis with mass spectrometric detection. Electrophoresis 2003, 24, 2340.
11. A. Tevell Ãberg, C. Olsson, U. Bondesson, M. Hedeland,. A mass spectrometric study on meloxicam metabolism in horses and the fungus Cunninghamella elegans, and the relevance of this microbial system as a model of drug metabolism in the horse. J. Mass Spectrom. 2009, 44, 1026.
12. M. I. Choudhary, N. T. Khan, S. G. Musharraf, S. Anjum, R. Atta, ur. Biotransformation of adrenosterone by filamentous fungus, Cunninghamella elegans. Steroids 2007, 72, 923.
13. H.-H. Huang, G.-L. Ma, Y.-M. Sun, Q. Li, D.-F. Zhong,. Phase II metabolites of etofesalamide in filamentous fungi. Acta Pharmacol. Sin. 2005, 26, 893.
14. S. -I. Kang, S. -Y. Kang, H. -G. Hur,. Identification of fungal metabolites of anticonvulsant drug carbamazepine. Appl. Microbiol. Biotechnol. 2008, 79, 663.
15. B. Ma, H.-H. Huang, X.-Y. Chen, Y.-M. Sun, L.-H. Lin, D.-F. Zhong,. Biotransformation of metoprolol by the fungus Cunninghamella blakesleeana. Acta Pharmacol. Sin. 2007, 28, 1067.
16. D. Zhang, F. E. Evans, J. P. Freeman, B. Duhart, Jr., C. E. Cerniglia,. Biotransformation of amitriptyline by Cunninghamella elegans. Drug Metab. Dispos. 1995, 23, 1417.
17. L. Lin, H. Huang, P. Zhang, X. Qi, D. Zhong,. Microbial transformation of dextromethorphan by Cunninghamella blakesleeana AS 3.153. Chem. Pharm. Bull. 2007, 55, 658.
18. J. V. Pothuluri, J. P. Freeman, F. E. Evans, C. E. Cerniglia,. Fungal metabolism of acenaphthene by Cunninghamella elegans. Appl. Environ. Microbiol. 1992, 58, 3654.
19. G. P. Rao, P. J. Davis,. Microbial models of mammalian metabolism: biotransformations of HP 749 (besipirdine) using Cunninghamella elegans. Drug Metab. Dispos. 1997, 25, 709.
20. A. Tevell Ãberg, H. Löfgren, U. Bondesson, M. Hedeland,. Structural elucidation of N-oxidized clemastine metabolites by liquid chromatography/tandem mass spectrometry and the use of Cunninghamella elegans to facilitate drug metabolite identification. Rapid Commun. Mass Spectrom. 2010, 24, 1447.
21. C. E. Cerniglia, J. P. Freeman, R. K. Mitchum,. Glucuronide and sulfate conjugation in the fungal metabolism of aromatic hydrocarbons. Appl. Environ. Microbiol. 1982, 43, 1070.
22. D. Zhang, Y. Yang, J. E. A. Leakey, C. E. Cerniglia,. Phase I and phase II enzymes produced by Cunninghamella elegans for the metabolism of xenobiotics. FEMS Microbiol. Lett. 1996, 138, 221.
23. L. Sun, H. -H. Huang, L. Liu, D. -F. Zhong,. Transformation of verapamil by Cunninghamella blakesleeana. Appl. Environ. Microbiol. 2004, 70, 2722.
24. F. P. Guengerich,. Cytochrome P450 and chemical toxicology. Chem. Res. Toxicol. 2008, 21, 70.