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Open Chemistry

formerly Central European Journal of Chemistry


IMPACT FACTOR 2018: 1.512
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2391-5420
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Volume 10, Issue 1

Issues

Volume 13 (2015)

A study of photodegradation of quetiapine by the use of LC-MS/MS method

Robert Skibiński
Published Online: 2011-11-24 | DOI: https://doi.org/10.2478/s11532-011-0133-4

Abstract

Photodegradation of quetiapine under UVC irradiation in methanol solution was investigated and structural elucidation of its photodegradation products was performed with the use of the reversed phase UHPLC system coupled with accurate mass hybrid ESI-Q-TOF mass spectrometer. During one run all essential data for the determination of photodegradation kinetics and for the structural elucidation of the products was collected with the use of auto MS/MS mode. Five degradation products were found and their masses and formulas were obtained with high accuracy (0.26–5.02 ppm). For all the analyzed compounds, MS/MS fragmentation spectra were also obtained allowing structural elucidation of the unknown degradation products and indicating photodegradation pathways of quetiapine. The main photodegradation product was identified as 2-[2-[4-(5-oxidodibenzo[b,f][1,4]thiazepin-11-yl)-1-piperazinyl]ethoxy]-ethanol and the photodegradation reaction yields the first-order kinetics with the rate constant k = 0.1094 h−1.

Keywords: UHPLC; Q-TOF; Photodegradation; Quetiapine; UV irradiation

  • [1] O. Gefvert, M. Bergstrom, B. Langstrom, T. Lundberg, L. Lindstrom, R. Yates, Psychopharm. 135, 119 (1998) http://dx.doi.org/10.1007/s002130050492CrossrefGoogle Scholar

  • [2] S.M. Cheer, A.J. Wagstaff, CNS Drugs 18, 173 (2004) http://dx.doi.org/10.2165/00023210-200418030-00004CrossrefGoogle Scholar

  • [3] ICH International Conference on Harmonisation of Technical requirements for registration of pharmaceuticals for human use, Photostability testing of new drug substances and products. Q1B (IFPMA, Geneva, 1996) Google Scholar

  • [4] ICH International Conference on Harmonisation of Technical requirements for registration of pharmaceuticals for human use, Stability testing of new drug substances and products. Q1A (IFPMA, Geneva, 2003) Google Scholar

  • [5] W. Aman, K. Thoma, Int. J. Pharm. 28, 33 (2002) http://dx.doi.org/10.1016/S0378-5173(02)00110-2CrossrefGoogle Scholar

  • [6] H.H. Tønnesen, Int. J. Pharm. 225, 1 (2001) http://dx.doi.org/10.1016/S0378-5173(01)00746-3CrossrefGoogle Scholar

  • [7] R.H. Clothier, Altern. Lab. Anim. 35, 515 (2007) Google Scholar

  • [8] S.A. Ozkan, B. Dogan, B. Uslu, Microchimica Acta 153, 27 (2006) http://dx.doi.org/10.1007/s00604-005-0457-xCrossrefGoogle Scholar

  • [9] E. Novakowa, Soudni Lekarstvi 49, 2 (2004) (In Czech) Google Scholar

  • [10] R.H. Pullen, K.M. Palermo, M.A. Curtis, J. Chromatogr. B 573, 49 (1992) Google Scholar

  • [11] D.T. Anderson, K.L. Fritz, J. Anal. Toxicol. 24, 300 (2000) Google Scholar

  • [12] D.D. Flamnia, T. Valouch, S. Venuti, J. Anal. Toxicol. 30, 287 (2006) Google Scholar

  • [13] S. Wise, A.J. Jenkins, J. Forensic Sci. 50, 209 (2005) http://dx.doi.org/10.1520/JFS2004068CrossrefGoogle Scholar

  • [14] L.J. Langman,, H.A. Kaliciak, S. Carlyle, J. Anal. Toxicol. 28, 520 (2004) Google Scholar

  • [15] J. Hasselstrom, K. Linnet, J. Chromatogr. B 798, 9 (2003) http://dx.doi.org/10.1016/S1570-0232(03)00592-0CrossrefGoogle Scholar

  • [16] C. Frahnert, M.L. Rao, K. Grasmader, J. Chromatogr. B 794, 35 (2003) http://dx.doi.org/10.1016/S1570-0232(03)00393-3CrossrefGoogle Scholar

  • [17] J. Sachse, J. Koller, S. Hartter, C. Hiemke, J. Chromatogr. B 830, 342 (2003) http://dx.doi.org/10.1016/j.jchromb.2005.11.032CrossrefGoogle Scholar

  • [18] R. Mandrioli, S. Fanali, A. Ferranti, M.A. Raggi, J. Pharm. Biomed. Anal. 30, 969 (2002) http://dx.doi.org/10.1016/S0731-7085(02)00395-3CrossrefGoogle Scholar

  • [19] P.C. Dawis, J. Wong, O. Gefvert, J. Pharm. Biomed. Anal. 20, 271 (1999) http://dx.doi.org/10.1016/S0731-7085(99)00036-9CrossrefGoogle Scholar

  • [20] L. Mercolini, M. Grillo, C. Bartoletti, G. Boncompagni, M.A. Raggi, Anal. Bioanal. Chem. 388, 235 (2007) http://dx.doi.org/10.1007/s00216-007-1195-1CrossrefGoogle Scholar

  • [21] M.A. Saracino, L. Mercolini, G. Flotta, L.J. Albers, R. Merli, M.A. Raggi, J. Chromatogr. B 843, 227 (2006) http://dx.doi.org/10.1016/j.jchromb.2006.06.001CrossrefGoogle Scholar

  • [22] J. Hopenwasser, A. Mozayani, T.J. Danielson, J. Harbin, H.S. Narula, D.H. Posey, P.W. Shrode, S.K. Wilson, R. Li, L.A. Sanchez, J. Anal. Toxicol. 28, 264 (2004) Google Scholar

  • [23] K.Y. Li, Y.G. Zhou, H.Y. Ren, F. Wang, B.K. Zhang, H.D. Li, J. Chromatogr. B 850, 581 (2007) http://dx.doi.org/10.1016/j.jchromb.2006.12.051CrossrefGoogle Scholar

  • [24] S.N. Lin, Y. Chang, D.E. Moody, R.L. Foltz, J. Anal. Toxicol. 28, 443 (2004) Google Scholar

  • [25] H. Kirchherr, W.N. Kuhn-Velter, J. Chromatogr. B 843, 100 (2006) http://dx.doi.org/10.1016/j.jchromb.2006.05.031CrossrefGoogle Scholar

  • [26] Z. Zhou, X. Li, K. Li, Z. Xie, J. Chromatogr. B 802, 257 (2004) http://dx.doi.org/10.1016/j.jchromb.2003.11.037CrossrefGoogle Scholar

  • [27] K.Y. Li, Z.N. Cheng, X. Li, X.L. Bai, B.K. Zhang, F. Wang, Acta Pharmacol. Sin. 25, 110 (2004) PubMedGoogle Scholar

  • [28] V. Pucci, R. Mandrioli, A. Ferranti, S. Furlanetto, M.A. Raggi, J. Pharm. Biomed. Anal. 32, 1037 (2003) http://dx.doi.org/10.1016/S0731-7085(03)00206-1CrossrefGoogle Scholar

  • [29] S.B. Bagade, S.P. Narkhede, D.S. Nikam, C.K. Sachde, Int. J. ChemTech Res. 1, 989 (2009) Google Scholar

  • [30] B.B. Hiraman, V. Sandip, R.T. Lohiya, M.J. Umekar, Int. J. ChemTech Res. 1, 1153 (2009) Google Scholar

  • [31] R.A. Fursule, D.K. Rupala, M.G. Khan, A.A. Shirkhedkar, S.J. Surana, Biosci. Biotech. Res. Asia 5, 461 (2008) Google Scholar

  • [32] S. Hillaert, L. Snoeck, W. Van den Bossche, J. Chromatogr. A 1033, 357 (2004) http://dx.doi.org/10.1016/j.chroma.2004.01.057CrossrefGoogle Scholar

  • [33] K.B. Vinay, H.D. Revanasiddappa, N. Rajendraprasad, Portugaliae Electrochim. Acta 28, 299 (2010) Google Scholar

  • [34] N. El-Enany, A. El-Brashy, F. Belal, N. El-Bahay, Portugaliae Electrochim. Acta 27, 113 (2009) http://dx.doi.org/10.4152/pea.200902113CrossrefGoogle Scholar

  • [35] R. Skibiński, Ł. Komsta, I. Kosztyła, J. Planar Chromatogr. 22, 289 (2008) http://dx.doi.org/10.1556/JPC.21.2008.4.12CrossrefGoogle Scholar

  • [36] E.U. Stolarczyk, A. Kutner, Acta Poloniae Pharm. Drug Res. 67, 599 (2010) Google Scholar

  • [37] E.U. Stolarczyk, Ł. Kaczmarek, K. Eksanow, M. Kubiszewski, M. Glice, A. Kutner, Pharm. Develop. Tech. 14, 29 (2009) http://dx.doi.org/10.1080/10837450802409388CrossrefGoogle Scholar

  • [38] F. Belal, A. Elbrashy, M. Eid, J.J. Nasr, J. Liq. Chromatogr. Ret. Tech. 31, 1283 (2008) http://dx.doi.org/10.1080/10826070802019681CrossrefGoogle Scholar

  • [39] D. Sharma, K.S. Srinivas, P. Gupta, D.P. Dwivedi, H. Dureja, M. Nagpal, P. Rakha, S. Goyal, Acta Pharm. Sci. 52, 345 (2010) Google Scholar

  • [40] I.V. Soma Raju, P. Raghuram, J. Sriramulu, Chromatographia 70, 545 (2009) http://dx.doi.org/10.1365/s10337-009-1183-zCrossrefGoogle Scholar

  • [41] S.R. Dhaneshwar, N.G. Patre, M.V. Mahadik, Acta Chromatogr. 21, 83 (2009) http://dx.doi.org/10.1556/AChrom.21.2009.1.7CrossrefGoogle Scholar

  • [42] R.K. Trivedi, M.C. Patel, Sci. Pharm. 79, 97 (2011) Google Scholar

About the article

Published Online: 2011-11-24

Published in Print: 2012-02-01


Citation Information: Open Chemistry, Volume 10, Issue 1, Pages 232–240, ISSN (Online) 2391-5420, DOI: https://doi.org/10.2478/s11532-011-0133-4.

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© 2011 Versita Warsaw. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License. BY-NC-ND 3.0

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