In vivo metabolic investigation of moxifloxacin using liquid chromatography/electrospray ionization tandem mass spectrometry in combination with online hydrogen/deuterium exchange experiments

Rapid Communications in Mass Spectrometry

Volumn 26, Issue 16, 2012, Pages 1817-1831

  Raju, B ^a   Ramesh, M ^a   Borkar, Roshan M ^a   Srinivas, R ^a   Padiya, Raju ^a   Banerjee, Sanjay K ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BIOMOLECULES; BODY FLUIDS; EXTRACTION; HIGH PRESSURE LIQUID CHROMATOGRAPHY; HYDROXYLATION; IONIZATION OF LIQUIDS; MASS SPECTROMETRY; PHASE SEPARATION;

ELECTROSPRAY IONIZATION TANDEM MASS SPECTROMETRY; HYDROGEN/DEUTERIUM EXCHANGE; IN-VIVO; LC-ESI-MS/MS; LC-MS-MS; LC/ESI-MS/MS; LIQUID CHROMATOGRAPHY ELECTROSPRAY; MOXIFLOXACIN; PHASE I; VIVO METABOLITES;

METABOLITES;

EID: 84863664362     PISSN: 09514198     EISSN: 10970231     Source Type: Journal    
DOI: 10.1002/rcm.6288     Document Type: Review

References (54)

1. G. M. Keating, L. J. Scott,. Moxifloxacin: a review of its use in the management of bacterial infections. Drugs 2004, 64, 2347.
2. K. Drlica, X. Zhao,. DNA gyrase, topoisomerase IV and the quinolones. Microbial Mol. Biol. Rev. 1997, 61, 377.
3. A. L. Djurdjevic, M. J. Stankov, P. Djurdjevic,. Optimization and validation of the direct HPLC method for the determination of moxifloxacin in plasma. J. Chromatogr. B 2006, 844, 104.
4. A. K. H. Kumar, G. Ramachandran,. Simple and rapid liquid chromatography method for determination of moxifloxacin in plasma. J.Chromatogr. B 2009, 877, 1205.
5. K. P. Chan, K. O. Chu, W. W. Lai, K. W. Choy, C. C. Wang, D. S. Lam, C. P. Pang,. Determination of ofloxacin and moxifloxacin and their penetration in human aqueous and vitreous humor by using high performance liquid chromatography fluorescence detection. Anal. Biochem. 2006, 353, 30.
6. H. A. Nguyena, J. Grelleta, B. B. Ba, C. Quentin, M. C. Saux,. Simultaneous determination of levofloxacin, gatifloxacin and moxifloxacin in serum by liquid chromatography with column switching. J. Chromatogr. B 2004, 810, 77.
7. H. Liang, M. B. Kays, K. M. Sowinski,. Separation of levofloxacin, ciprofloxacin, gatifloxacin, moxifloxacin, trovafloxacin and cinoxacin by high-performance liquid chromatography: application to levofloxacin determination in human plasma. J. Chromatogr. B 2002, 772, 53.
8. T. Lemoine, D. Breilh, D. Ducint, J. Dubrez, J. Jougon, J. F. Velly, M. C. Saux,. Determination of moxifloxacin (BAY 12-8039) in plasma and lung tissue by high performance liquid chromatography with ultraviolet detection using a fully automated extraction method with a new polymeric cartridge. J. Chromatogr. B 2000, 742, 247.
9. Y. H. Xu, D. Li, X. Y. Liu, Y. Z. Li, J. Lu,. High performance liquid chromatography assay with ultra violet detection for moxifloxacin: Validation and application to a pharmacokinetic study in Chinese volunteers. J. Chromatogr. B 2010, 878, 3437.
10. J. De Smet, K. Boussery, K. Colpaert, P. De Sutter, P. D. Paepe, J. Decruyenaere, J. Van Bocxlaer,. Pharmacokinetics of fluoroquinolones in critical care patients: A bio-analytical HPLC method for the simultaneous quantification of ofloxacin, ciprofloxacin and moxifloxacin in human plasma. J. Chromatogr. B 2009, 877, 961.
11. B. Prasad, S. Singh,. In vitro and in vivo investigation of metabolic fate of rifampicin using an optimized sample preparation approach and modern tools of liquid chromatography mass spectrometry. J. Pharm. Biomed. Anal. 2009, 50, 475.
12. B. Prasad, A. Garg, H. Takwani, S. Singh,. Metabolite identification by liquid chromatography-mass spectrometry. Trends Anal. Chem. 2011, 30, 360.
13. n and LC-HR-MS. Eur. J. Pharm. Sci. 2010, 41, 173.
14. T. Liu, F. Du, Y. Wan, F. Zhu, J. Xing,. Rapid identification of phase I and II metabolites of artemisinin antimalarials using LTQ Orbitrap hybrid mass spectrometer in combination with online hydrogen/deuterium exchange technique. J. Mass Spectrom. 2011, 46, 725.
15. G. Chen, I. Daaro, B. N. Pramanik, J. J. Piwinski,. Structural characterization of in vitro rat liver microsomal metabolites of antihistamine desloratadine using LTQ Orbitrap hybrid mass spectrometer in combination with online hydrogen/deuterium exchange HR-LC/MS. J. Mass Spectrom. 2009, 44, 203.
16. S. Beuck, W. Schanzer, M. Thevis,. Investigation of the in vitro metabolism of the emerging drug candidates S107 for doping-preventive purposes. J. Mass Spectrom. 2011, 46, 112.
17. J. C. Wolff, A. M. Laures,. 'On-the-fly' hydrogen/deuterium exchange liquid chromatography mass spectrometry using a dual-sprayer atmospheric pressure ionization source. Rapid Commun. Mass Spectrom. 2006, 20, 3769.
18. D. Q. Liu, C. E. Hop,. Strategies for characterization of drug metabolites using liquid chromatography tandem mass spectrometry in conjunction with chemical derivatization and on-line H/D exchange approaches. J. Pharm. Biomed. Anal. 2005, 37, 1.
19. W. Lam, R. Ramanathan,. In electrospray ionization source hydrogen/deuterium exchange LC-MS and LC-MS/MS for characterization of metabolites. J. Am. Soc. Mass Spectrom. 2002, 13, 345.
20. W.H.O. Report. Global tuberculosis control (WHO/HTM/TB/2011.16), 2009. Available:.
21. S. H. Gillespie, O. Billington,. Activity of moxifloxacin against mycobacteria. J. Antimicrob. Chemother. 1999, 44, 393.
22. Y. Hu, A. R. Coates, D. A. Mitchison,. Sterilizing activities of fluoroquinolones against rifampin-tolerant populations of Mycobacterium tuberculosis. Antimicrob. Agents Chemother. 2003, 47, 653.
23. N. Veziris, C. T. Pernot, A. Aubry, V. Jarlier, N. Lounis,. Fluoroquinolone-containing third-line regimen against Mycobacterium tuberculosis in vivo. Antimicrob. Agents Chemother. 2003, 47, 3117.
24. M. V. N. De Souza,. Promising drugs against tuberculosis. Recent Pat. Anti infect. Drug Discov. 2006, 1, 33.
25. A. S. Ginsburg, R. Sun, H. Calamita,. Emergence of fluoroquinolone resistance in Mycobacterium tuberculosis during continuously dosed moxifloxacin monotherapy in a mouse model. Antimicrob. Agents Chemother. 2005, 49, 3977.
26. L. R. Codecasa, G. Ferrara, M. Ferrarese, M. A. Morandi, V. Penati, C. Lacchini, P. Vaccarino, G. Migliori,. Long-term moxifloxacin in complicated tuberculosis patients with adverse reactions or resistance to first line drugs. Respir. Med. 2006, 100, 1566.
27. P. A. Moise, M. C. Birmingham, J. J. Schentag,. Pharmacokinetics and metabolism of moxifloxacin. Drugs Today 2000, 36, 229.
28. H. Stass, D. Kubitza, A. Halabi, H. Delesen,. Pharmacokinetics of moxifloxacin, a novel 8-methoxy-quinolone, in patients with renal dysfunction. Br. J. Clin. Pharmacol. 2002, 53, 232.
29. H. Stass, D. Kubitza,. Pharmacokinetics and elimination of moxifloxacin after oral and intravenous administration in man. J. Anti Microb. Chemother. 1999, 43, 83.
30. n experiments: Development of a validated specific stability-indicating LC-MS method. J. Pharm. Biomed. Anal. 2011, 56, 560.
31. B. Raju, M. Ramesh, R. M. Borkar, R. Padiya, S. K. Banerjee, R. Srinivas,. Development and validation of liquid chromatography-mass spectrometric method (LC-MS) for simultaneous determination of moxifloxacin and ketorolac in rat plasma: Application to pharmacokinetic study. Biomed. Chromatogr. 2012. DOI: 10.1002/bmc.2701.
32. B. Raju, V. Ramesh, A. Sudhakar, M. Ramesh, V. U. M. Sarma, S. Chandrasekhar, R. Srinivas,. Diastereomeric differentiation of norbornene amino acid peptides by electrospray ionization tandem mass spectrometry. Rapid Commun. Mass Spectrom. 2009, 23, 2965.
33. n). J. Am. Soc. Mass Spectrom. 2011, 23, 703.
34. C. K. Y. Yu, C. N. W. Lam, K. Springob, J. Schmidt, I. K. Chu, C. Lo,. Constitutive accumulation of cis-piceid in transgenic arabidopsis overexpressing a sorghum stilbene synthase gene. Plant Cell Physiol. 2006, 47, 1017.
35. D. Callemien, S. Collin,. Use of RP-HPLC-ESI(-)-MS/MS to differentiate various proanthocyanidin isomers in larger beer extracts. Am. Soc. Brew. Chem. Inc. 2008, DOI: 10.1094/ASBCJ-2008-0215-01.
36. H. J. Li, M. L. Deinzer,. Tandem mass spectrometry for sequencing proanthocyanidins. Anal. Chem. 2007, 79, 1739.
37. J. H. Banoub, M. Delmas,. Structural elucidation of the wheat straw lignin polymer by atmospheric pressure chemical ionization tandem mass spectrometry and matrix assisted laser desorption/ionization time-of-flight mass spectrometry. J. Mass Spectrom. 2003, 38, 900.
38. n ion-trap time-of-flight mass spectrometry. Rapid Commun. Mass Spectrom. 2008, 22, 373.
39. Q. Li, G. Yan, T. Ge,. A fragmentation study of podophyllotoxin and its 4-demethyl-4β-substituted derivatives by electrospray ionization ion-trap time-of-flight tandem mass spectrometry. Rapid Commun. Mass Spectrom. 2007, 21, 2843.
40. A. B. Attygalle, J. Ruzicka, D. Varughese, J. B. Bialecki, S. Jafri,. Low-energy collision-induced fragmentation of negative ions derived from ortho-, meta- and para-hydroxyphenyl carbaldehydes, ketones, and related compounds. J. Mass Spectrom. 2007, 42, 1207.
41. A. C. Schmidt, R. Herzschuh, F. M. Matysik, W. Engewald,. Investigation of the ionisation and fragmentation behaviour of different nitroaromatic compounds occurring as polar metabolites of explosives using electrospray ionisation tandem mass spectrometry. Rapid Commun. Mass Spectrom. 2006, 20, 2293.
42. E. R. Filho, W. Xie, C. J. Mirocha, L. R. Hogge,. Fragmentation of some zearalenones by fast-atom bombardment mass spectrometry. Rapid Commun. Mass Spectrom. 1997, 11, 1515.
43. D. Q. Liu,. Collision induced fluorine atom migration in atmospheric pressure ionization mass spectrometry. J. Mass Spectrom. 2003, 38, 1210.
44. 4COF, with fluorine atom migration. Org. Mass Spectrom. 1991, 26, 1023.
45. S. Tajima, S. Takahashi, O. Sekiguchi,. Elimination of difluorocarbene from the molecular ions of α,α,α-trifluorocresols with a fluorine atom migration in an ion trap mass spectrometer. Rapid Commun. Mass Spectrom. 1999, 13, 1458.
46. 3. Int. J. Mass Spectrom. Ion Processes 1997, 161, 133.
47. S. Tajima, M. Ueki, S. Tajima, O. Sekiguchi, A. Shigihara,. Unimolecular HF loss from the molecular ions of fluorophenols and fluoroanilines. A 'ring-walk' mechanism of a fluorine atom. Rapid Commun. Mass Spectrom. 1996, 10, 1076.
48. T. Yanagisawa, S. Tajima, M. Iizuka, S. Tobita, M. Mitani, T. Matsumoto,. Metastable ion study of fluorinated organic compounds. Part 3. α,α,α-Trifluoroanisole and α,α,α- trifluorocresols. Int. J. Mass Spectrom. Ion Processes 1993, 125, 55.
49. J. Xu, Y. Ma, S. Xu, Y. Zhao,. Negative-ion electrospray ionization mass spectrometry of N-benzyloxycarbonyl-protected 1-substituted and cyclic taurines. Rapid Commun. Mass Spectrom. 2005, 19, 1835.
50. E. G. Lewars, R. E. March,. Fragmentation of 3-hydroxyflavone; a computational and mass spectrometric study. Rapid Commun. Mass Spectrom. 2007, 21, 1669.
51. J. B. Ari, A. Etinger, A. Weis, A. Mandelbaum,. Hydrogen-shift isomerism: mass spectrometry of isomeric benzenesulfonate and 2-, 3- and 4-dehydrobenzenesulfonic acid anions in the gas phase. J. Mass Spectrom. 2005, 40, 1064.
52. Y. P. Tu, H. S. Yuan, S. Y. Liu,. Mass spectrometric evidence for the generation of benzyne from benzoyl peroxide in thermolysis. Rapid Commun Mass Spectrom. 1996, 10, 1093.
53. N. M. M. Nibbering,. Four decades of joy in mass spectrometry. Mass Spectrom. Rev. 2006, 25, 962; and references cited therein.
54. Q. N. Porter,. Mass Spectrometry of Heterocyclic Compounds, (2nd edn.), Wiley-Interscience, New York, 1985, pp. 691, 746, 770, 771, 799, 801.