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)


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).


Cefpodoxime Proxetil Ester Prodrug Poor Oral Bioavailability Gonococcal Urethritis Carboxylic Acid Functional Group 
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  1. Borin MT. A Review of the Pharmacokinetics of Cefpodoxime Proxetil. Drugs 1991; 42:13–21PubMedCrossRefGoogle Scholar
  2. Borin MT, Hughes GS, Patel RK, Royer ME, and Cathcart KS. Pharmacokinetic and Tolerance Studies of Cefpodoxime after Single-and Multiple-Dose Oral Administration of Cefpodoxime Proxetil. J Clin Pharmacol 1991; 31:1137–1145PubMedGoogle Scholar
  3. Crauste-Manciet S, Decroix MO, Farinotti R, and Chaumeil JC. Cefpodoxime-Proxetil Hydrolysis and Food Effects in the Intestinal Lumen before Absorption: In Vitro Comparison of Rabbit and Human Material. Int. J Pharm 1997a; 157:153–161PubMedCrossRefGoogle Scholar
  4. Crauste-Manciet S, Huneau JF, Decroix MO, Tome D, Farinotti R, and Chaumeil JC. Cefpodoxime Proxetil Esterase Activity in Rabbit Small Intestine: A Role in the Partial Cefpodoxime Absorption. Int J Pharm 1997b; 149:241–269CrossRefGoogle Scholar
  5. Frampton JE, Brogden RN, Langtry HD, and Buckley MM. Cefpodoxime Proxetil. A Review of its Antibacterial Activity, Pharmacokinetic Properties and Therapeutic Potential. Drugs 1992; 44:889–917PubMedCrossRefGoogle Scholar
  6. Fujimoto K, Ishihara S, Yanagisawa H, Ide J, Nakayama E, Nakao H, Sugawara S, and Iwata M. Studies on Orally Active Cephalosporin Esters. J Antibiot 1987; 40:370–384PubMedGoogle Scholar
  7. Hamaura T, Kusai A, and Nishimura K. Gel Formation of Cefpodoxime Proxetil. STP Pharm Sci 1995a; 324–331Google Scholar
  8. Hamaura T, Kusai A, and Nishimura K. Unusual Dissolution Behavior of Cefpodoxime Proxetil: Effects of pH and Ionic Factor. STP Pharm Sci 1995b; 332–338Google Scholar
  9. Hughes GS Jr, Heald DL, Patel R, Spillers CR, Batts DH, and Euler AR. Gastric Emptying and the Pharmacokinetics of the Cephalosporin Antibiotic, Cefpodoxime Proxetil. Methods Find Exp Clin Pharmacol 1990; 12:197–204PubMedGoogle Scholar
  10. Nakao H, Fujimoto K, Ishihara S, Sugawara S, and Igarashi I. Cephalosporin Derivatives, Their Preparation and Composition Containing Them. Eur Pat Appl.(1982); EP 0 049 118 A3Google Scholar
  11. Nicolaos G, Crauste-Manciet S, Farinotti R, and Brossard D. Improvement of Cefpodoxime Proxetil Oral Absorption in Rats by an Oil-in-Water Submicron Emulsion. Int J Pharm 2003; 263(1–2):165–171PubMedCrossRefGoogle Scholar
  12. Rodriguez JC, Hernandez R, Gonzalez M, Rodriguez Z, Tolon B, Velez H, Valdes B, Lopez MA, and Fini A. An Improved Method for Preparation of Cefpodoxime Proxetil. Farmaco 2003; 58:363–369PubMedCrossRefGoogle Scholar
  13. Todd WM. Cefpodoxime Proxetil: A Comprehensive Review. Int J Antimicrob Agents 1994; 4:37–62CrossRefPubMedGoogle Scholar
  14. Tremblay D, Dupront A, Ho C, Coussediere D, and Lenfant B. Pharmacokinetics of Cefpodoxime in Young and Elderly Volunteers after Single Doses. J Antimicrob Chemother 1990; 26:Suppl E:21–28PubMedGoogle Scholar
  15. Wise R. The Pharmacokinetics of the Oral Cephalosporins-A Review. J Antimicrob Chemother 1990; 26Suppl E:13–20PubMedGoogle Scholar

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© 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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