Structural characterization of sulfadiazine metabolites using H/D exchange combined with various MS/MS experiments

Journal of the American Society for Mass Spectrometry

Volumn 16, Issue 10, 2005, Pages 1687-1694

  Pfeifer, Thomas ^a   Tuerk, Jochen ^b   Fuchs, Regine ^c  

^a Metabolite Service   (Germany)

^b Institute of Energy and Environmental Technology IUTA   (Germany)

^c WATERS CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHARACTERIZATION; ISOMERS; MASS SPECTROMETRY; STRUCTURE (COMPOSITION); SULFUR COMPOUNDS;

MASS MEASUREMENT; SULFADIAZINE; SYNTHETIC COMPOUNDS; TIME OF FLIGHT MASS SPECTROMETRY (TOF-MS);

METABOLITES;

ACID; CARBON; HYDROGEN; OXYGEN; PYRIMIDINE DERIVATIVE; SULFADIAZINE;

ACCURACY; ARTICLE; ISOMER; MASS SPECTROMETRY; MEASUREMENT; METABOLITE; METHODOLOGY; NONHUMAN; TANDEM MASS SPECTROMETRY; TIME OF FLIGHT MASS SPECTROMETRY;

ANIMALS; DEUTERIUM EXCHANGE MEASUREMENT; FECES; MASS SPECTROMETRY; MOLECULAR STRUCTURE; SULFADIAZINE; SWINE;

SUS SCROFA;

EID: 25144490032     PISSN: 10440305     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jasms.2005.06.008     Document Type: Article

References (38)

1. B. Halling-Sørensen, S. Nors Nilsen, P.F. Lanzky, F. Ingerslev, H.C. Holten-L̈tzhoft, S.E. Jørgensen Occurrence, fate, and effects of pharmaceutical substances in the environment - A review Chemosphere 36 1998 357
2. K. Kuemmerer K. Kuemmerer 2nd ed. Pharmaceuticals in the environment. Sources, fate, effects, and risks Vol. XXXI 2004 Springer Publishing Berlin, Germany
3. R. Hirsch, T.A. Ternes, K. Haberer, A. Mehlich, F. Ballwanz, K.L. Kratz Determination of antibiotics in different water compartments via liquid chromatography-electrospray tandem mass spectrometry J. Chromatogr. A. 815 2 1998 213 223
4. C. Hartig, T. Storm, M. Jeckel Detection and identification of sulphonamide drugs in municipal waste water by liquid chromatography coupled with electrospray ionization tandem mass spectrometry J. Chromatogr. A 854 1999 163 173
5. R. Hirsch, T.A. Ternes, K. Haberer, K.L. Kratz Occurrence of antibiotics in the aquatic environment Sci. Total Environ 225 1999 10
6. M.E. Lindsey, T.M. Meyer, E.M. Thurman Analysis of trace levels of sulfonamide and tetracycline antimicrobials in groundwater and surface water using solid-phase extraction and liquid chromatography/mass spectrometry Anal. Chem. 73 19 2001 4640 4646
7. T. Pfeifer, J. Tuerk, K. Bester, M. Spiteller Determination of selected sulfonamide antibiotics and trimethoprim in manure by electrospray and atmospheric pressure chemical ionization tandem mass spectrometry Rapid Commun. Mass Spectrom. 16 7 2002 663 669
8. M.Y. Haller, S.R. Muller, C.S. McArdell, A.C. Alder, M.J. Suter Quantification of veterinary antibiotics (sulfonamides and trimethoprim) in animal manure by liquid chromatography-mass spectrometry J. Chromatogr. A 952 1/2 2002 111 120
9. E.R. Campagnolo, K.R. Johnson, A. Karpati, C.S. Rubin, D.W. Kolpin, M.T. Meyer, J.E. Esteban, R.W. Currier, K. Smith, K.M. Thu, M. McGeehin Antimicrobial residues in animal waste and water resources proximal to large-scale swine and poultry feeding operations Sci. Total Environ. 299 1/3 2002 89 95
10. S.R. Mueller, H. Singer, K. Stoob, M. Burkhardt, N. Hartmann, C. Goetz, C. Stamm, C. Waul Occurrence and fate of antibiotics in manure, soil, and water Mitt. Lebensm. Hyg. 94 6 2003 574 578
11. X.S. Miao, F. Bishay, M. Chen, C.D. Metcalfe Occurrence of antimicrobials in the final effluents of wastewater treatment plants in Canada Environ. Sci. Technol. 38 13 2004 3533 3541
12. S. Yang, J. Cha, K. Carlson Quantitative determination of trace concentrations of tetracycline and sulfonamide antibiotics in surface water using solid-phase extraction and liquid chromatography/ion trap tandem mass spectrometry Rapid Commun. Mass Spectrom. 18 18 2004 2131 2145
13. J.F. Nouws, D. Mevius, T.B. Vree, M. Degen Pharmacokinetics and renal clearance of sulfadimidine, sulfamerazine, and sulfadiazine and their N4-acetyl and hydroxy metabolites in pigs Vet. Q 11 2 1989 78 86
14. P. Nielsen, C. Friis, N. Gyrd-Hansen, F. Rasmussen Metabolism of sulfadiazine in neonatal and young pigs. Comparative in vivo and in vitro studies Biochem. Pharmacol. 35 15 1986 2509 2512
15. J.F. Nouws, T.B. Vree, Y.A. Hekster In vitro antimicrobial activity of hydroxy and N4-acetyl sulphonamide metabolites Vet. Q 7 1 1985 70 72
16. 35S-sulfadiazine alone and in the presence of thrimethoprim Drug Metab. Dispos. 7 2 1979 94 99
17. E. Schoondermark-van de Ven, T. Vree, W. Melchers, W. Camps, J. Galama In vitro effects of sulfadiazine and its metabolites alone and in combination with pyrimethamine on Toxoplasma gondii Antimicrob. Agents Chemother 39 3 1995 763 765
18. Y.Q. Xia, J.D. Miller, R. Bakhtiar, R.B. Franklin, D.Q. Liu Use of a quadrupole linear ion trap mass spectrometer in metabolite identification and bioanalysis Rapid Commun. Mass Spectrom. 17 11 2003 1137 1145
19. G. Hopfgartner, C. Husser, M. Zell Rapid screening and characterization of drug metabolites using a new quadrupole-linear ion trap mass spectrometer J. Mass Spectrom. 38 2 2003 138 150
20. M.R. Anari, R.I. Sanchez, R. Bakhtiar, R.B. Franklin, T.A. Baillie Integration of knowledge-based metabolic predictions with liquid chromatography data-dependent tandem mass spectrometry for drug metabolism studies Application to studies on the biotransformation of indinavir Anal. Chem. 76 3 2004 823 832
21. R. Ramanathan, D.L. McKenzie, M. Tugnait, K. Siebenaler Application of semi-automated metabolite identification software in the drug discovery process for rapid identification of metabolites and the cytochrome P450 enzymes responsible for their formation J. Pharm. Biomed. Anal. 28 5 2002 945 951
22. H.K. Lim, S. Stellingweif, S. Sisenwine, K.W. Chan Rapid drug metabolite profiling using fast liquid chromatography, automated multiple-stage mass spectrometry, and receptor-binding J. Chromatogr. A 831 2 1999 227 241
23. P.R. Tiller, A.P. Land, I. Jardine, D.M. Murphy, R. Sozio, A. Ayrton, W.H. Schaefer Application of liquid chromatography-mass spectrometry(n) analyzes to the characterization of novel glyburide metabolites formed in vitro J. Chromatogr. A 794 1/2 1998 15 25
24. K. Klagkou, F. Pullen, M. Harrison, A. Organ, A. Firth, G.J. Langley Fragmentation pathways of sulphonamides under electrospray tandem mass spectrometric conditions Rapid Commun. Mass Spectrom. 17 21 2003 2373 2379
25. N. Ohashi, S. Furuuchi, M. Yoshikawa Usefulness of the hydrogen-deuterium exchange method in the study of drug metabolism using liquid chromatography-tandem mass spectrometry J. Pharm. Biomed. Anal. 18 3 1998 325 334
26. L. Gianelli, G.G. Mellerio, E. Siviero, A. Rossi, W. Cabri, L. Sogli Mass spectrometry of avermectins Structural determination of two new derivatives of Ivermectin B(1a) Rapid Commun. Mass Spectrom. 14 14 2000 1260 1265
27. M.A. Olsen, P.G. Cummings, S. Kennedy-Gabb, B.M. Wagner, G.R. Nicol, B. Munson The use of deuterium oxide as a mobile phase for structural elucidation by HPLC/UV/ESI/MS Anal. Chem. 72 20 2000 5070 5078
28. D.Q. Liu, C.E. Hop, M.G. Beconi, A. Mao, S.H. Chiu Use of on-line hydrogen/deuterium exchange to facilitate metabolite identification Rapid Commun. Mass Spectrom. 15 19 2001 1832 1839
29. W. Blum, R. Aichholz, P. Ramstein, J. Kuhnol, J. Bruggen, T. O'Reilly, A. Florsheimer In vivo metabolism of epothilone B in tumor-bearing nude mice Identification of three new epothilone B metabolites by capillary high-pressure liquid chromatography/mass spectrometry/tandem mass spectrometry Rapid Commun. Mass Spectrom 15 1 2001 41 49
30. W. Lam, R. Ramanathan In ectrospray ionization source hydrogen/deuterium exchange LC-MS and LC-MS/MS for characterization of metabolites J. Am. Soc. Mass Spectrom 13 4 2002 345 353
31. W. Blum, T. Buhl, E. Altmann, J. Kuhnol, P. Ramstein, R. Aichholz Complementary use of ion trap/time-of-flight mass spectrometry in combination with capillary high-pressure liquid chromatography Early characterization of in vivo metabolites of the cathepsin K inhibitor NVP-AAV490 in rat J. Chromatogr. B, Biomed. Appl. 787 2 2003 255 270
32. A.E. Nassar Online hydrogen-deuterium exchange and a tandem-quadrupole time-of-flight mass spectrometer coupled with liquid chromatography for metabolite identification in drug metabolism J. Chromatogr. Sci. 41 8 2003 398 404
33. P.O. Edlund, P. Baranczewski Identification of BVT. 2938 metabolites by LC/MS and LC/MS/MS after in vitro incubations with liver microsomes and hepatocytes J. Pharm. Biomed. Anal. 34 5 2004 1079 1090
34. R. Ramanathan, A.D. Su, N. Alvarez, N. Blumenkrantz, S.K. Chowdhury, K. Alton, J. Patrick Liquid chromatography/mass spectrometry methods for distinguishing N-oxides from hydroxylated compounds Anal. Chem. 72 6 2000 1352 1359
35. W. Tong, S.K. Chowdhury, J.C. Chen, R. Zhong, K.B. Alton, J.E. Patrick Fragmentation of N-oxides (deoxygenation) in atmospheric pressure ionization Investigation of the activation process Rapid Commun. Mass Spectrom. 5 22 2001 2085 2090
36. M.P. Dilrukshi, L. Wing, M. Steven, R. Ramanathan Distinguishing N-oxide and hydroxyl compounds Impact of heated capillary/heated ion transfer tube in inducing atmospheric pressure ionization source decompositions J. Mass Spectrom 39 2004 600 606
37. T.B. Vree, E. Schoondermark-van de Ven, C.P. Verwey-van Wissen, A.M. Bars, A. Swolfs, P.M. van Galen, H. Amatdjais-Groenen Isolation, identification, and determination of sulfadiazine and its hydroxy metabolites and conjugates from man and Rhesus monkey by high-performance liquid chromatography J. Chromatogr. B, Biomed. Appl. 670 1 1995 111 123
38. J.F. Nouws, E.C. Firth, T.B. Vree, M. Baakman Pharmacokinetics and renal clearance of sulfamethazine, sulfamerazine, and sulfadiazine and their N4-acetyl and hydroxy metabolites in horses Am. J. Vet. Res. 48 3 1987 392 402