Synthesis of Metabolites and Related Substances of Rabeprazole, an Anti-Ulcerative Drug

REFERENCES

• Morri , M. ; Takeguchi , N. Different biochemical modes of action of two irreversible H(+)-K(+) ATPase inhibitors, omeprazole and E3810 . J. Biol. Chem. 1993 , 268 , 21553 – 21559 .
   PubMed Web of Science ®Google Scholar
• Nakai , H. ; Shimamura , Y. ; Kanazawa , T. ; Yasuda , S. ; Kayano , M. Determination of a new H+-K+ ATPase inhibitor (E3810) and its four metabolites in human plasma by high-performance liquid chromatography . J. Chrom. B: Bicmed. Appl. 1994 , 660 , 211 – 220 .
   PubMed Web of Science ®Google Scholar
• Fujisaki , H. ; Shibata , H. ; Oketani , K. ; Murakami , M. ; Fujimoto , M. ; Wakabayashi , T. ; Yamatsu , I. ; Yamaguchi , M. ; Sakai , H. ; Takeguchi , N. Inhibitions of acid secreation by E3810 and omeprazole, and their reversal by glutathine . Biochem. Pharmacol. 1991 , 42 , 321 – 328 .
   PubMed Web of Science ®Google Scholar
• Takeguchi , N. ; Yamanouchi , T. ; Sakai , H. ; Mora , M. New fluorescent probes E3810 and E3810 methoxy for determining distributions of the apical membrane and the acidic compartment of gastric acid secreting cells . Jpn. J. Physiol. 1992 , 42 , 75 – 88 .
   PubMedGoogle Scholar
• Carswel , C. I. ; Goa , K. L. Rabeprazole: An update of its use in acid-related disorders. Drugs 2001, 61, 2327–2356.
   PubMed Web of Science ®Google Scholar
• Barth , J. ; Hahne , W. Rabeprazole-based therapy in Helicobacter pylori eradication . Aliment. Pharmacol. Ther. 2002 , 16 , 31 – 33 .
   PubMed Web of Science ®Google Scholar
• Garcia , C. V. ; Nudelman , N. S. ; Steppe , M. ; Schapoval , E. E. S. Structural elucidation of rabeprazole sodium photodegradation products . J. Pharm. Biomed. Anal. 2008 , 46 , 88 – 93 .
   PubMed Web of Science ®Google Scholar
• International Conference on Harmonization (ICH) Guidelines. Q3A (R) impurities in new drug substances. February 2002. Available at http://www.ich.org/LOB/media/MEDIA422.pdf .
   Google Scholar
• International Conference on Harmonization (ICH) Guidelines. Q2B validation of analytical procedure: Methodology. 6, November 1996. Available at http://www.ikev.org/haber/stabilite/kitap/36%201.8%20%20Stability%20Workshop%20ICH%20Q2B%20C%20.pdf .
   Google Scholar
• Uno , T. ; Yasui-Furukori , N. ; Shimizu , K. ; Sugawara , T. ; Tateishi , T. Determination of rabeprazole and its active metabolite, rabeprazole thioether, in human plasma by column-switching high performance liquid chromatography and its application to pharmacokinetic study . J. Chromatogr. B 2005 , 824 , 238 – 243 .
   PubMed Web of Science ®Google Scholar
• Pingili , R. R. ; Jambula , M. R. ; Ganta , M. R. ; Ghanta , M. R. ; Sajja , E. ; Sundaram , V. ; Boluggdu , V. B. Identification and synthesis of potential impurities of rabeprazole sodium . Pharmazie 2005 , 60 ( 11 ), 814 – 818 .
   PubMed Web of Science ®Google Scholar
• Reddy , G. M. ; Bhaskar , B. V. ; Reddy , P. P. ; Sudhakar , P. ; Babu , J. M. ; Vyas , K. ; Reddy , P. R. ; Mukkanti , K. Identification and characterization of potential impurities of rabeprazole sodium . J. Pharm. Biomed. Anal. 2007 , 43 , 1262 – 1269 .
   PubMed Web of Science ®Google Scholar
• Mano , N. ; Oda , Y. ; Takakuwa , S. ; Chiku , S. ; Nakata , H. ; Asakawa , N. Plasma direct injection high-performance liquid chromatographic method for simultaneously determining E3810 enantiomers and their metabolites by using flavoprotein-conjugated column . J. Pharm. Sci. 1996 , 85 , 903 – 907 .
   PubMed Web of Science ®Google Scholar
• Singh , S. S. ; Jain , M. ; Shah , H. ; Gupta , S. ; Thakker , P. ; Shah , R. ; Lohray , B. Direct injection, column switching-liquid chromatographic technique for the estimation of rabeprazole in bioequivalence study . J. Chromatogr. B 2004 , 813 , 247 – 254 .
   PubMed Web of Science ®Google Scholar
• Takakuwa , S. ; Chiku , S. ; Nakata , H. ; Yuzuriha , T. ; Mano , N. ; Asakawa , N. Enantioselective high-performance liquid chromatographic assay for determination of the enantiomers of a new anti-ulcer agent, E3810 . J. Chrom, B: Biomed. Appl. 1995 , 673 , 113 – 122 .
   PubMed Web of Science ®Google Scholar
• Ramakrishna , N. V. ; Vishwottam , S. ; Wishu , M. ; Koteshwara , M. ; Kumar , S. High-performance liquid chromatography method for the quantification of rabeprazole in human plasma using solid-phase extraction . J. Chromatogr. B 2005 , 816 , 209 – 214 .
   PubMed Web of Science ®Google Scholar
• Zhang , Y. ; Chen , X. ; Gu , Q. ; Zhong , D. Quantification of rabeprazole in human plasma by liquid chromatography-tandem mass spectrometry . Anal. Chim. Acta 2004 , 523 , 171 – 175 .
   Web of Science ®Google Scholar
• Huang , J. ; Xu , Y. ; Gao , S. ; Rui , L. ; Guo , Q. Development of a liquid chromatography/tandem mass spectrometry assay for the quantification of rabeprazole in human plasma. Rapid Commun. Mass Spectrom. 2005, 19, 2321–2324.
   PubMed Web of Science ®Google Scholar
• Tivesten , A. ; Folestad , S. ; Schonbacher , V. ; Svensson , K. Nonaqueous capillary electrophoresis for the analysis of labile pharmaceutical compounds . Chromatographia 1999 , 49 , S7 – S11 .
   Web of Science ®Google Scholar
• El-Gindy , A. ; El-Yazy , F. ; Maher , M. M. Spectrophotometric and chromatographic determination of rabeprazole in presence of its degradation products . J. Pharm. Biomed. Anal. 2003 , 31 , 229 – 242 .
   PubMed Web of Science ®Google Scholar
• Radi , A. ; El-Ghany , N. ; Wahdan , T. Voltammetric behavior of rabeprazole at a glassy carbon electrode and its determination in tablet dosage form . Farmaco 2004 , 59 , 515 – 518 .
   PubMedGoogle Scholar
• Garcia , C. V. ; Sippel , J. ; Sfair , L. ; Garcia , S. S. ; Jablonski , A. ; Steppe , M. ; Schapoval , E. E. S. Validation of derivative spectrophotometric method for determination of rabeprazole sodium in pharmaceutical formulation . J. AOAC Int. 2005 , 88 , 1081 – 1085 .
   PubMed Web of Science ®Google Scholar
• Garcia , C. V. ; Sippel , J. ; Steppe , M. ; Schapoval , E. E. S. Development and validation of derivative spectrophotometric method for determination of rabeprazole sodium in pharmaceutical formulation . Anal. Lett. 2006 , 39 , 341 – 348 .
   Web of Science ®Google Scholar
• Nozal , M. J. ; Torbio , L. ; Bernal , J. ; Alonso , C. ; Jimenez , A. Comparative study of the enantioselective separation of several antiulcer drugs by high-performance liquid chromatography and supercritical fluid chromatography . J. Chromatogr. A 2005 , 1091 , 118 – 123 .
   PubMed Web of Science ®Google Scholar
• Miura , M. ; Tada , H. ; Satoh , S. ; Habuchi , T. ; Suzuki , T. Determination of rabeprazole enantiomers and their metabolites by high-performance liquid chromatography with solid phase extraction . J. Pharm. Biomed. Anal. 2006 , 41 , 565 – 570 .
   PubMed Web of Science ®Google Scholar
• Rao , R. N. ; Raju , A. N. ; Nagaraju , D. Enantiospecific resolution of rabeprazole by liquid chromatography on amylose-derived chiral stationary phase using photo diode array and polarimetric detectors in series . Talanta 2006 , 70 , 805 – 810 .
   PubMed Web of Science ®Google Scholar
• (a) Cosme , G. A. ; Fau dec , J. M. M. ; Gelpi , V. J. M. ; Molina , P.A. Process for the production of 2-(2-pyridinylmehtylsulphinyl)-1H-benzimidazoles. WO 0104109, 2001; (b) Shigeru , S. ; Norihiro , U. ; Shuhei , M. ; Katsuya , T. ; Seiichiro , N. ; Makoto , O. ; Naoyuki , S. ; Toshihiko , K. ; Masatoshi , F. ; Manabu , M. ; Kiyoshi , O. ; Hideaki , F. ; Hisashi , S. ; Tsuneo , W. Pyridine derivatives having anti-ulcerative activity. US 5,045,552, 1991 .
   Google Scholar
• DRL Communication No. IPDO-IPM-00022
   Google Scholar