Identification, isolation and characterization of new impurity in rabeprazole sodium

P Sreenivasa Rao; Uttam Kumar Ray; P Badarinadh Gupta; D V N Srinivasa Rao; Aminul Islam; Pradeep Rajput; K Mukkanti

doi:10.1016/j.jpba.2010.01.034

Identification, isolation and characterization of new impurity in rabeprazole sodium

J Pharm Biomed Anal. 2010 Aug 1;52(4):620-4. doi: 10.1016/j.jpba.2010.01.034. Epub 2010 Jan 25.

Authors

P Sreenivasa Rao¹, Uttam Kumar Ray, P Badarinadh Gupta, D V N Srinivasa Rao, Aminul Islam, Pradeep Rajput, K Mukkanti

Affiliation

¹ Department of Chemical Research, Aurobindo Pharma Ltd. Research Centre, 313, Bachupally, Quthubullapur Mandal, Hyderabad 500090, India.

PMID: 20153594
DOI: 10.1016/j.jpba.2010.01.034

Abstract

Rabeprazole sodium [1] is a proton pump inhibitor, used as an antiulcerative. During the manufacturing of rabeprazole sodium, we observed an unknown impurity at levels 0.05-0.1% in HPLC analysis along with the known potential impurities. This new unknown impurity was isolated using preparative liquid chromatography. Based on the complete spectral analysis ((1)H NMR, (13)C NMR, DEPT, Mass and IR), this new impurity was designated as 2-[[(3-methyl-4-(methylthio)-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole (methylthio impurity of rabeprazole). Impurity isolation, structure elucidation and probable formation mechanism was discussed.

Publication types

Comparative Study

MeSH terms

2-Pyridinylmethylsulfinylbenzimidazoles / chemistry*
2-Pyridinylmethylsulfinylbenzimidazoles / isolation & purification*
Chromatography, High Pressure Liquid
Drug Contamination*
Rabeprazole
Technology, Pharmaceutical* / methods

Substances

2-Pyridinylmethylsulfinylbenzimidazoles
Rabeprazole