AJAC  Vol.6 No.2 , January 2015
Hydrolytic Degradation Study of Lansoprazole, Identification, Isolation and Characterisation of Base Degradation Product
Abstract: Lansoprazole degradation is accelerated in both acidic and basic medium in water. The present investigation deals with the hydrolytic degradation of Lansoprazole. Acidic medium degradation show all known impurities and degradation products whereas basic degradation studies show new impurity which has higher molecular weight than Lansoprazole. New impurity was identified, isolated using mass based auto purification system and characterised by 1H NMR, 13C NMR, HMBC, HSQC, NOE, COSY and HRMS experiments. Isolated impurity was showing molecular weight of 467.10, molecular formula of C23H16F3N5OS and its name is 7-(3-Methyl-4-(2,2,2-trifluoroethoxy) pyridin-2-yl)-7H-benzo[4,5]imidazo[2,1-b]benzo[4,5]imidazo[2,1-d][1,3,5]thiadiazine.
Cite this paper: Battu, S. and Pottabathini, V. (2015) Hydrolytic Degradation Study of Lansoprazole, Identification, Isolation and Characterisation of Base Degradation Product. American Journal of Analytical Chemistry, 6, 145-155. doi: 10.4236/ajac.2015.62013.

[1]   Richter, J.E., Campbell, D.R., Kahrilas, P.J., Huang, B. and Fludas, C. (2000) Lansoprazole Compared with Ranitidine for the Treatment of Nonerosive Gastroesophageal Reflux Disease. Archives of Internal Medicine, 160, 1803-1809.

[2]   Brummer, R.J., Geerling, B.J. and Stockbrugger, R.W. (1997) Initial and Chronic Gastric Acid Inhibition by Lansoprazole and Omeprazole in Relation to Meal Administration. Digestive Disease and Sciences, 42, 132-137.

[3]   Tang, G., Serfaty-Lacronsniere, C., Camilo, M.E. and Russell, R.M. (1996) Gastric Acidity Influences the Blood Response to a Beta-Carotene Dose in Humans. American Journal of Clinicle Nutrition, 64, 22-26.

[4]   Tolman, K.G., Sanders, S.W., Buchi, K.N., Karol, M.D., Jennings, D.E. and Ringham, G.L. (1997) The Effects of Oral Doses of Lansoprazole and Omeprazole on Gastric pH. Journal of Clinicle Gastroenterology, 24, 65-70.

[5]   Fitton, A. and Wiseman, L. (1996) Pantoprazole: A Review of Its Pharmacological Properties and Therapeutic Use in Acid-Related Disorders. Drugs, 51, 460-482.

[6]   Matheson, A.J. and Jarvis, B. (2001) Lansoprazole: An Update of Its Place in the Management of Acid-Related Disorders. Drugs, 61, 1801-1833.

[7]   Nudelman, N.S. and Estabilidad de (1975) Medicamentos. EI Ateno, Buenos Aires.

[8]   Kommanaboyina, B. and Rhodes, C.T. (1999) Trends in Stability Testing, with Emphasis on Stability during Distribution and Storage. Drug Development and Industrial Pharmacy, 25, 857-868.

[9]   Karljikovic-Rajic, K., Novovic, D., Marinkovic, V. and Agbaba, D. (2003) Journal of Pharmaceutical and Biomedical Analysis, 32, 1019-1027.

[10]   Anil Kumar, A., Venkata Ramana, K., Narasimha Raju, C.H. and Sudhakara Rao, G. (2012) A Simple UV Spectrophotometric Method for Determination of Lansoprazole in Bulk and Pharmaceutical Dosage Forms. International Journal of Pharmaceutical, Chemical and Biological Sciences, 2, 524-528.

[11]   Alagar raja, M., Yadav, S.K., Rai, A. and Mishra, S. (2011) Analytical Estimation of Lansoprazole and Validation of Simple Spectrophotometric in Bulk and Capsule Formulation. International Journal of Research in Pharmaceutical Sciences, 2, 521-524.

[12]   Okram, Z.D., Kanakapura, B., Jagannathamurthy, R.P. and Basavaiah, V.K. (2012) Development of a Simple UV-Spectrophotometric Method for the Determination of Lansoprazole and Study of Its Degradation Profile. Química Nova, 35, 386-391.

[13]   Rao, P.V., Kumar, M.N. and Kumar, M.R. (2013) A Novel, Validated Stability-Indicating UPLC Method for the Estimation of Lansoprazole and Its Impurities in Bulk Drug & Pharmaceutical Dosage Forms. Scientia Pharmaceutica, 81, 183-193.

[14]   Al-Momani, I.F. and Rababah, M.H. (2010) Validation of HPLC and FIA Spectrophotometric Methods for the Determination of Lansoprazole in Pharmaceutical Dosage Forms and Human Plasma. American Journal of Analytical Chemistry, 1, 34-39.

[15]   Muthu Kumar, S., Selva Kumar, D., Raj Kumar, T., Udhaya Kumar, E., Suba Geetha, A. and Diwedi, D. (2010) Development and Validation of RP-HPLC Method for the Estimation of Lansoprazole in Tablet Dosage Form. Journal of Chemical and Pharmaceutical Research, 2, 291-295.

[16]   Luo, Y.F., Xu, L.S., Xu, M., Feng, J. and Tang, X. (2012) A Validated Specific, Stability Indicating HPLC Method for Determination of Lansoprazole Enteric Coated Capsules and Related Impurities. Asian Journal of Pharmaceutical Sciences, 7, 149-154.

[17]   Patel, B., Dedani, Z., Dedani, R., Ramolia, C., Sagar, V. and Mehta, R.S. (2009) Simultaneous Estimation of Lansoprazole and Domperidone in Combined Dosage Form by RP-HPLC. Asian Journal of Research in Chemistry, 2, 210-212.

[18]   Brown, S.D., Connor, J.D., Smallwood, N.C. and Lugo, R.A. (2011) Quantification of Lansoprazole in Oral Suspension by Ultra-High-Performance Liquid Chromatography Hybrid Ion-Trap Time-of-Flight Mass Spectrometry. International Journal of Analytical Chemistry, 2011, Article ID: 832414.

[19]   Katsuki, H., Hamada, A., Nakamura, C., Arimori, K. and Nakano, M. (2011) High-Performance Liquid Chromatographic Assay for the Simultaneous Determination of Lansoprazole Enantiomers and Metabolites in Human Liver Microsomes. Journal of Chromatography B, 757, 127-133.

[20]   Cirilli, R., Ferretti, R., Gallinella, B., Turchetto, L., Zanitti, L. and La Torre, F. (2009) Development and Validation of an Enantioselective and Chemoselective HPLC Method Using a Chiralpak IA Column to Simultaneously Quantify(R)-(+)- and (S)-(?)-Lansoprazole Enantiomers and Related Impurities. Journal of Pharmaceutical and Biomedical Analysis, 50, 9-14.

[21]   Petkovska, R., Cornett, C. and Dimitrovska, A. (2008) Chemometrical Approach in Lansoprazole and Its Related Compounds Analysis by Rapid Resolution RP-HPLC Method. Journal of Liquid Chromatography & Related Technologies, 31, 2159-2173.

[22]   Srinivas, K.S.V., Mukkanti, K., Buchireddy, R. and Srinivasulu, P. (2010) Detection, Isolation and Characterisation of Principal Synthetic Route Indicative Impurity in Lansoprazole. E-Journal of Chemistry, 7, 844-848.

[23]   Reddy, G.M., Mukkanti, K., Laxmi Kumar, T., Moses Babu, J. and Reddy, P.P. (2008) Synthesis and Characterization of Metabolites and Potential Impurities of Lansoprazole, an Antiulcerative Drug. Synthetic Communications, 38, 3477-3489.

[24]   Ramulu, K., Rao, B.M. and Someswara Rao, N. (2013) Identification, Isolation and Characterization of Potential Degradation Product in Lansoprazole Drug Substance. Rasayan Journal of Chemistry, 6, 274-283.