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Prodrugs pp 1387-1394 | Cite as

Case Study: Vantin: A Prodrug of Cefpodoxime

  • Arvind K. Chappa
Part of the Biotechnology: Pharmaceutical Aspects book series (PHARMASP, volume V)

Abstract

Cefpodoxime proxetil is an ester prodrug of the extended spectrum antibiotic cefpodoxime, developed by Sankyo Co., Ltd, Japan. It was designed to overcome the poor oral bioavailability of the parent drug. Cefpodoxime (pKa ∼2.20 ± 0.10) exists predominantly in the ionic form at intestinal pH and thus exhibits poor permeability (Fujimoto et al., 1987). The free carboxylic acid moiety in cefpodoxime offers opportunities for the preparation of prodrugs. Esterification of this carboxylic acid functional group with an isopropyloxycarbonyloxyethyl group removes the ionizable group and improves lipohilicity, enabling the compound to be absorbed by passive diffusion after oral administration (Fujimoto et al., 1987). Approximately 50% of the drug is reported to be absorbed systemically as cefpodoxime (Tremblay et al., 1990).

Keywords

Cefpodoxime Proxetil Ester Prodrug Poor Oral Bioavailability Gonococcal Urethritis Carboxylic Acid Functional Group 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© American Association of Pharmaceutical Scientists 2007

Authors and Affiliations

  • Arvind K. Chappa
    • 1
  1. 1.Department of Pharmaceutical ChemistryThe University of KansasLawrenceUSA

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