Identification, Characterization and Synthesis of Process Related Unknown Impurity in Cetirizine Dihydrochloride

Jagadeesh Narkedimilli; Ravindra Kumar Yalavarthi; Sandeep Mohanty; Kirti Kumar Jain; Sandeep Reddy Gaddam; Jayashree Anireddy

doi:10.14233/ajchem.2017.20223

Issue

Vol. 29 No. 2 (2017): Vol 29 Issue 2

Issue Published : November 30, 2016

This work is licensed under a Creative Commons Attribution 4.0 International License.

Identification, Characterization and Synthesis of Process Related Unknown Impurity in Cetirizine Dihydrochloride

https://doi.org/10.14233/ajchem.2017.20223

Jagadeesh Narkedimilli

Dr. Reddy’s Laboratories Limited, API Plant, Bollaram-III, Plot No 116, IDA Bollaram, Medak District, Hyderabad-502 325, India; Centre for Chemical Sciences and Technology, Institute of Science and Technology, Jawaharlal Nehru Technological University Hyderabad, Kukatpally, Hyderabad-500 085, India

Ravindra Kumar Yalavarthi

Dr. Reddy’s Laboratories Limited, API Plant, Bollaram-III, Plot No 116, IDA Bollaram, Medak District, Hyderabad-502 325, India

Sandeep Mohanty

Dr. Reddy’s Laboratories Limited, API Plant, Bollaram-III, Plot No 116, IDA Bollaram, Medak District, Hyderabad-502 325, India

Kirti Kumar Jain

Dr. Reddy’s Laboratories Limited, API Plant, Bollaram-III, Plot No 116, IDA Bollaram, Medak District, Hyderabad-502 325, India

Sandeep Reddy Gaddam

Dr. Reddy’s Laboratories Limited, API Plant, Bollaram-III, Plot No 116, IDA Bollaram, Medak District, Hyderabad-502 325, India

Jayashree Anireddy

Centre for Chemical Sciences and Technology, Institute of Science and Technology, Jawaharlal Nehru Technological University Hyderabad, Kukatpally, Hyderabad-500 085, India

Corresponding Author(s) : Jagadeesh Narkedimilli

jagadeeshn@drreddys.com; nark_012@yahoo.com

Asian Journal of Chemistry, Vol. 29 No. 2 (2017): Vol 29 Issue 2
Article Published : November 30, 2016

Abstract

Identification, isolation, structural characterization and synthesis of process generated unknown impurity in cetirizine dihydrochloride is described in this work. Process-related unknown impurity was detected in the range of 0.1-0.15 % in cetirizine dihydrochloride by a gradient HPLC and LC-MS methods. Based on LC-ESI/MSⁿ study, the chemical structure of impurity was presumed as 2-(2-(4-(2-(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)ethyl)piperazin-1-yl)ethoxy)acetic acid. The impurity was isolated by preparative HPLC, the complete spectral analysis, MS, 1D NMR (¹H and ¹³C), 2D NMR (COSY, HSQC and HMBC) confirmed the proposed chemical structure of impurity.

Keywords

Synthesis Liquid chromatography-mass spectrometry Cetirizine

Narkedimilli, J., Yalavarthi, R. K., Mohanty, S., Jain, K. K., Gaddam, S. R., & Anireddy, J. (2016). Identification, Characterization and Synthesis of Process Related Unknown Impurity in Cetirizine Dihydrochloride. Asian Journal of Chemistry, 29(2), 409–413. https://doi.org/10.14233/ajchem.2017.20223

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References

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D.A. Pflum, D. Krishnamurthy, Z. Han, S.A. Wald and C.H. Senanayake, Tetrahedron Lett., 43, 923 (2002).

Q. Song, H. Junga, Y. Tang, A.C. Li, T. Addison, M. McCort-Tipton, B. Beato and W. Naidong, J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 814, 105 (2005).

J. Macek, P. Ptacek and J. Klima, J. Chromatogr. B Biomed. Sci. Appl., 736, 231 (1999).

A.M.Y. Jaber, H.A. Al Sherife, M.M. Al Omari and A.A. Badwan, J. Pharm. Biomed. Anal., 36, 341 (2004).

M. Ma, F. Feng, Y. Sheng, S. Cui and H. Liu, J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 846, 105 (2007).

M.D. Likar, H.L. Mansour and J.W. Harwood, J. Pharm. Biomed. Anal., 39, 543 (2005).

S. Rudaz, S. Souverain, C. Schelling, M. Deleers, A. Klomp, A. Norris, T.L. Vu, B. Ariano and J.-L. Veuthey, Anal. Chim. Acta, 492, 271 (2003).

S. Karakus, I. Kucukguzel and S.G. Kucukguzel, J. Pharm. Biomed. Anal., 46, 295 (2008).

S.W. Kang, H.J. Jang, V.S. Moore, J.-Y. Park, K.A. Kim, J.R. Youm and S.B. Han, J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 878, 3351 (2010).

A.D. de Jager, H.K.L. Hundt, K.J. Swart, A.F. Hundt and J. Els, J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 773, 113 (2002).

J. Dharuman, M. Vasudhevan and T. Ajithlal, J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 879, 2624 (2011).

S. Azhagvuel and R. Sekar, J. Pharm. Biomed. Anal., 43, 873 (2007).

C.K. Kim, K.J. Yeon, E. Ban, M.J. Hyun, J.K. Kim, M.K. Kim, S.E. Jin and J.S. Park, J. Pharm. Biomed. Anal., 37, 603 (2005).

M.F. Zaater, Y.R. Tahboub and N.M. Najib, J. Pharm. Biomed. Anal., 22, 739 (2000).

Z.R. Tan, D.S. Ouyang, G. Zhou, L.S. Wang, Z. Li, D. Wang and H.H. Zhou, J. Pharm. Biomed. Anal., 42, 207 (2006).

A.F.M. El Walily, M.A. Korany, A. El Gindy and M.F. Bedair, J. Pharm. Biomed. Anal., 17, 435 (1998).

S.N. Makhija and P.R. Vavia, J. Pharm. Biomed. Anal., 25, 663 (2001).

S.O. Choi, S.H. Lee, H.S. Kong, E.J. Kim and H.Y.P. Choo, J. Chromatogr. B Biomed. Sci. Appl., 744, 201 (2000).

L. Toribio, M.J. del Nozal, J.L. Bernal, C. Cristofol and C. Alonso, J. Chromatogr. A, 1121, 268 (2006).

P. Mikus, P. Kubacak, I. Valaskova and E. Havranek, Acta Fac. Pharm. Univ. Comen., 52, 172 (2005).

International Conference on Harmonization; Guidelines on Impurities in New Drug Substances: Q3A (R2) (2006).

http://bdg.co.nz/coa/coa_110299_5710.1_20100912_V1_Cetirizine_Dihydrochloride.pdf (accessed 13.03.16).

Issue

Vol. 29 No. 2 (2017): Vol 29 Issue 2

Identification, Characterization and Synthesis of Process Related Unknown Impurity in Cetirizine Dihydrochloride

Corresponding Author(s) : Jagadeesh Narkedimilli

Abstract

Keywords

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