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Identification and characterization of geometrical isomeric photo degradation product of eprosartan using LC-MS and LC-NMR
Ravi Piyushkumar Shah (1)
, Archana Sahu (2) , Saranjit Singh (3,*) (1) Department of Pharmaceutical Analysis, National Institute of Pharmaceutical Education and Research (NIPER), SAS Nagar 160062, Punjab, India
(2) Department of Pharmaceutical Analysis, National Institute of Pharmaceutical Education and Research (NIPER), SAS Nagar 160062, Punjab, India
(3) Department of Pharmaceutical Analysis, National Institute of Pharmaceutical Education and Research (NIPER), SAS Nagar 160062, Punjab, India
(*) Corresponding Author
Received: 17 Jun 2010 | Revised: 08 Apr 2011 | Accepted: 02 Nov 2010 | Published: 30 Jun 2011 | Issue Date: June 2011
Abstract
The degradation of eprosartan was evaluated under ICH/WHO prescribed stress conditions. The drug degraded to only one product under photo alkali condition, whereas it was stable to conditions of hydrolysis, oxidation and thermal stress. The drug and its co-eluting product were well separated on RP-HPLC in a gradient mode. Subsequently, LC-MS/TOF and on-line H/D exchange studies were performed on both of them. The two showed same molecular mass, similar fragment ions and even the same number of labile hydrogens indicating the product to be an isomer of the drug. To confirm the same, 1H and COSY LC-NMR studies were carried out by using an enriched sample. Distinguishing behaviour of chemical shifts proved the product to be (Z)-4-((2-butyl-5-(2-carboxy-3-(thiophen-2-yl)prop-1-enyl)-1H-imidazol-1-yl)methyl)benzoic acid. The structure was further supported by differential LC-MS ion intensities of the drug and the product.
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European Journal of Chemistry
Keywords
Eprosartan; Degradation behaviour; Photoisomerization; Geometric isomer; LC-MS; LC-NMR
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DOI: 10.5155/eurjchem.2.2.152-157.170
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doi:10.1016/j.jpba.2009.03.017
PMid:19410412
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doi:10.1002/mrc.2404
PMid:19173350
[7]. Shah, R. P.; Sahu, A.; Singh, S. J. Pharm. Biomed. Anal. 2010, 51, 1037-1046.
doi:10.1016/j.jpba.2009.11.008
PMid:20018473
[8]. Shah, R. P.; Singh, S. J. Pharm. Biomed. Anal. 2010, 53, 755-761.
doi:10.1016/j.jpba.2010.05.005
PMid:20554147
[9]. Hoffman, B. B. in: Brunton, L.L. Goodman & Gilman’s The Pharmacological Basis of Therapeutics, 11th Edition, McGraw-Hill, 859-860, 2006.
[10]. Available at: http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?Fuseaction=Search.DrugDetails (accessed on 11 April 2011).
[11]. Hsu, L. C. J. Liq. Chrom. & Rel. Technol. 1998, 21, 1685-1700.
doi:10.1080/10826079808001252
PMCid:1176066
[12]. Xue-Ning, L.; Hong-Rong, X.; Wei-Li, C.; Gang-Yi, L.; Nan-Nan. C.; Chen Y. J. Chromatogr. B 2007, 853, 47-53.
[13]. Ferreirós, N.; Iriarte, G.; Alonsoa, R. M.; Jiménez, R. M.; Ortíz, E. J. Chromatogr. A 2006, 1119, 309-314.
doi:10.1016/j.chroma.2006.02.055
PMid:16542666
[14]. ICH Topic Q1B, Stability Testing: Photostability Testing of New Drug Substances and Products, in: International Conference on Harmonisation, IFPMA, Geneva, 1996.
[15]. Bakshi, M.; Singh, S. J. Pharm. Biomed. Anal. 2002, 28, 1011-1040.
doi:10.1016/S0731-7085(02)00047-X
[16]. Mayer-Helm, B.; Hofbauer, L.; Pani, J. J. Mass. Spectrom. 2010, (Article in Press; doi:10.1002/jms.1757).
[17]. Ge, G. B.; Zhang, R.; Ail, C. Z.; He Y. Q.; Zhang Y. Y.; Liu X. B.; Yang L.; Wang Z. T.; Yang L. Rapid Commun. Mass Spectrom. 2009, 23, 425-432.
doi:10.1002/rcm.3892
PMid:19125430
[18]. Brum, J.; Hannah, R. Rapid Commun. Mass Spectrom. 1997, 11, 1430-1434.
doi:10.1002/(SICI)1097-0231(19970830)11:13<1430::AID-RCM7>3.0.CO;2-5
[19]. Thoma, K.; Kuebler, N.; Reimann, E. Pharmazie 1997, 52, 362-373.
PMid:9229718
[20]. Albini, A.; Fasani, E. in: Tønnesen H. H. The Photostability of Drugs and Drug Formulations, 2nd Edition, Taylor and Francis, 69-71, 2004.
How to cite
Shah, R.; Sahu, A.; Singh, S.
Eur. J. Chem.
2011,
2(2), 152-157.
doi:10.5155/eurjchem.2.2.152-157.170
Shah, R.; Sahu, A.; Singh, S. Identification and characterization of geometrical isomeric photo degradation product of eprosartan using LC-MS and LC-NMR.
Eur. J. Chem.
2011,
2(2), 152-157.
doi:10.5155/eurjchem.2.2.152-157.170
Shah, R., Sahu, A., & Singh, S.
(2011).
Identification and characterization of geometrical isomeric photo degradation product of eprosartan using LC-MS and LC-NMR.
European Journal of Chemistry, 2(2), 152-157.
doi:10.5155/eurjchem.2.2.152-157.170
Shah, Ravi, Archana Sahu, & Saranjit Singh.
"Identification and characterization of geometrical isomeric photo degradation product of eprosartan using LC-MS and LC-NMR." European Journal of Chemistry [Online], 2.2 (2011): 152-157. Web. 10 Dec. 2023
Shah, Ravi, Sahu, Archana, AND Singh, Saranjit.
"Identification and characterization of geometrical isomeric photo degradation product of eprosartan using LC-MS and LC-NMR" European Journal of Chemistry [Online], Volume 2 Number 2 (30 June 2011)
The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item
DOI Link: https://doi.org/10.5155/eurjchem.2.2.152-157.170
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