European Journal of Chemistry 2011, 2(2), 152-157. doi:https://doi.org/10.5155/eurjchem.2.2.152-157.170

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, Accepted: 02 Nov 2010, Published: 30 Jun 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.2_2_152_157_800

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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How to cite


Shah, R.; Sahu, A.; Singh, S. Eur. J. Chem. 2011, 2(2), 152-157. doi:https://doi.org/10.5155/eurjchem.2.2.152-157.170
Shah, R.; Sahu, A.; Singh, S. Eur. J. Chem. Identification and characterization of geometrical isomeric photo degradation product of eprosartan using LC-MS and LC-NMR. 2011, 2(2), 152-157. doi:https://doi.org/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:https://doi.org/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. 19 Jun. 2018
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)

DOI: https://doi.org/10.5155/eurjchem.2.2.152-157.170

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