Prodrugs pp 1185-1194 | Cite as

Case Study: Cefditoren Pivoxil: An Oral Prodrug of Cefditoren

  • Tarra Fuchs
Part of the Biotechnology: Pharmaceutical Aspects book series (PHARMASP, volume V)


There is a continual need for new broad-spectrum antibiotics and, with this in mind, Sakagami and coworkers developed cefditoren pivoxil (Spectracef®) as an orally available prodrug of cefditoren (1990). Cefditoren has a 2-aminothiazole methoxime ring that imparts gram-negative activity (Balbisi, 2002) and a methylthiazole-substituted vinyl group at C-3 that maintains gram-positive activity (Sakagami et al.,1990). However, the hydrophilic carboxyl group of the parent drug makes cefditoren orally inactive due to poor permeation across the intestinal mucosa (Kees and Grobecker, 1995; Stoeckel et al., 1995). Esterfication of the polar carboxyl group increases lipophilicity and allows intestinal absorption to occur (Kees and Grobecker, 1995). That is, cefditoren pivaloyl methyl ester is not biologically active, but after absorption esterases readily hydrolyze the prodrug to the biologically active cefditoren (von Daehne et al., 1970; Li et al., 1997; Brass et al., 2003).


Moraxella Catarrhalis Sodium Tripolyphosphate Oral Cephalosporin Cefetamet Pivoxil Pivalic Acid 
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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© American Association of Pharmaceutical Scientists 2007

Authors and Affiliations

  • Tarra Fuchs
    • 1
  1. 1.Sunesis PharmaceuticalsSouth San FranciscoUSA

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