Structural elucidation of degradation products of a benzopyridooxathiazepine under stress conditions using electrospray orbitrap mass spectrometry - Study of degradation kinetic

European Journal of Pharmaceutical Sciences

Volumn 45, Issue 5, 2012, Pages 559-569

  Lecoeur, Marie ^a   Vérones, Valérie ^a   Vaccher, Claude ^a   Bonte, Jean Paul ^a   Lebegue, Nicolas ^a   Goossens, Jean Franois ^a  

^a UNIV LILLE   (France)

Author keywords

Degradation kinetic; Electrospray orbitrap mass spectrometry; Fragmentation; Liquid chromatography; Validation

Indexed keywords

1 (4 METHOXYPHENYLETHYL) 11H BENZO[F] 1,2 DIHYDROPYRIDO[3,2,C][1,2,5]OXATHIAZEPINE 5,5 DIOXIDE; SODIUM HYDROXIDE; THIAZEPINE DERIVATIVE; UNCLASSIFIED DRUG;

ACCURACY; ACIDITY; ALKALINITY; ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; COMPUTER PROGRAM; DRUG DEGRADATION; DRUG HYDROLYSIS; DRUG OXIDATION; DRUG STABILITY; ELECTROSPRAY MASS SPECTROMETRY; HEAT STRESS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PHOTOLYSIS; PREDICTIVE VALUE; PRIORITY JOURNAL; QUALITY CONTROL; STRESS; STRUCTURE ANALYSIS; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY; ULTRAVIOLET SPECTROSCOPY;

ACIDS; ANTIMITOTIC AGENTS; CHROMATOGRAPHY, LIQUID; DRUG STABILITY; HYDROGEN-ION CONCENTRATION; HYDROLYSIS; KINETICS; OXIDATION-REDUCTION; PHOTOLYSIS; REPRODUCIBILITY OF RESULTS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STRESS, PHYSIOLOGICAL; THIAZEPINES;

EID: 84857920262     PISSN: 09280987     EISSN: 18790720     Source Type: Journal    
DOI: 10.1016/j.ejps.2011.12.009     Document Type: Article

References (18)

1. M. Barbero, S. Bazzi, S. Cadamuro, and S. Dughera Synthetic and mechanistic aspects of acid-catalyzed disproportionation of dialkyl diarylmethyl ethers: a combined experimental and theoretical study Eur. J. Org. Chem. 3 2009 430 436
2. M. Feinberg Validation of analytical methods based on accuracy profiles J. Chromatogr. A 1158 2007 174 183 (Pubitemid 47021136)
3. Gallet, S., Lebegue, N., Flouquet, N., Berthelot, P., Pierré, A., Renard, P., Pfeiffer, B., 2004. PCT FR 04/00235.
4. S. Gallet, N. Flouquet, P. Carato, B. Pfeiffer, P. Renard, S. Léonce, A. Pierré, P. Berthelot, and N. Lebegue Benzopyridooxathiazepine derivatives as novel potent antimitotic agents Bioorg. Med. Chem. 17 2009 1132 1138
5. M.J. Gómez, C. Sirtori, M. Mezcua, A.R. Fernández-Alba, and A. Agüera Photodegradation study of three dipyrone metabolites in various water systems: identification and toxicity of their photodegradation products Water Res. 42 2008 2698 2706
6. Ph. Hubert, J.J. Nguyen-Hu, B. Boulanger, E. Chapuzet, P. Chiap, P.A. Compagnon, W. Dewé, M. Feinberg, M. Lallier, N. Mercier, G. Muzard, C. Nivet, and L. Valat Validation des procédures analytiques quantitatives: Harmonisation des démarches STP Pharma Pratiques 13 2003 101 138 (Pubitemid 36791125)
7. Ph. Hubert, J.J. Nguyen-Hu, B. Boulanger, E. Chapuzet, N. Cohen, P.A. Compagnon, W. Dewé, M. Feinberg, M. Laurentie, N. Mercier, G. Muzard, and L. Valat Validation des procédures analytiques quantitatives: Statistiques STP Pharma Pratiques 16 2006 28 58
8. ICH, 2003. Stability Testing of New Drug Substances and Products Q1A(R2). Current Step 4 Version (6 February 2003).
9. I. Iovel, K. Mertins, J. Kischel, A. Zapf, and M. Beller An efficient and general iron-catalyzed arylation of benzyl alcohols and benzyl carboxylates Angew. Chem., Int. Ed. 44 2005 3913 3917 (Pubitemid 40885709)
10. M.S. Lee, and E.H. Kerns LC/MS application in drug development Mass Spectrom. Rev. 18 1999 187 279
11. A. Makarov, E. Denisov, A. Kholomeev, W. Balschun, O. Lange, K. Strupat, and S. Horning Performance evaluation of a hybrid linear ion trap/orbitrap mass spectrometer Anal. Chem. 78 2006 2113 2120
12. M.A. Meetani, S.M. Hisaindee, F. Abdullah, S.S. Ashraf, and M.A. Rauf Liquid chromatography tandem mass spectrometry analysis of photodegradation of a diazo compound: a mechanistic study Chemosphere 80 2010 422 427
13. A.L. Piccinelli, L. Campone, F. Dal Piaz, O. Cuesta-Rubio, and L. Rastelli Fragmentation pathways of polycyclic polyisoprenylated benzophenones and degradation profile of nemorosone by multiple-stage tandem mass spectrometry J. Am. Soc., Mass Spectrom. 20 2009 1688 1698
14. F. Qiu, S. Pennino, C.A. Busacca, and D.L. Norwood Identification of a process impurity formed during synthesis of a nevirapine analogue HIV NNRT inhibitor using LC/MS and forced degradation studies J. Pharm. Biomed. Anal. 49 2009 733 738
15. J.J. Ritter, and J.J. Kalish A new reaction of nitriles. II: Synthesis of t-carbinamines Am. Chem. Soc. 70 1948 4048 4050
16. J.J. Ritter, and P.P. Minieri A new reaction of nitriles. I: Amides from alkenes and mononitriles J. Am. Chem. Soc. 70 1948 4045 4047
17. A. Vigroux, A.J. Kresge, and J.C. Fishbein Generation and direct measurement of the reactivity of an N-nitrosiminium cation with nucleophiles in aqueous media J. Am. Chem. Soc. 117 1995 4433 4434
18. Y. Wu The use of liquid chromatography-mass spectrometry for the identification of drug degradation products in pharmaceutical formulations Biomed. Chromatogr. 14 2000 384 396