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Medicinal Chemistry Research

, Volume 21, Issue 11, pp 3361–3368 | Cite as

Synthesis, characterization and in vitro hydrolysis studies of ester and amide prodrugs of dexibuprofen

  • Zaman AshrafEmail author
  • Muhammad Imran
  • Shahid Amin
Original Research

Abstract

Ten prodrugs of dexibuprofen having ester and amide moieties instead of free carboxylic acid which involves in gastrointestinal side effects have been synthesized. Dexibuprofen acid chloride was condensed with different amino acid methyl ester hydrochlorides and five alcohols to afford the amide and ester prodrugs. All of the synthesized prodrugs were characterized by their mp, R f, elemental analysis, FTIR, 1H NMR, and 13C NMR spectroscopy. The in vitro hydrolysis studies in plasma reflect prodrugs have been varied in terms of reactivity toward hydrolysis, owing to the different chemical structures. In alkyl substitution the branched chain alkyl substituents or aromatic substituents resulted in enhanced lipophilicity but diminished dissolution and hydrolysis rate. The amide prodrugs with branched and aromatic substitution can also be considered for sustained release. Prodrugs are less irritating to gastric mucosa than dexibuprofen.

Keywords

Prodrugs Dexibuprofen NSAIDs 

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Copyright information

© Springer Science+Business Media, LLC 2011

Authors and Affiliations

  1. 1.Chemistry DepartmentAllama Iqbal Open UniversityIslamabadPakistan
  2. 2.Riphah Institute of Pharmaceutical SciencesRiphah International UniversityIslamabadPakistan
  3. 3.Kohat University of Science and TechnologyKohatPakistan

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