Prodrugs pp 1173-1183 | Cite as

Case Study: Capecitabine: A Prodrug of 5-Fluorouracil

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


Capecitabine (2), is an off-white crystalline solid with and aqueous solubility of 26 mg/mL. It is sold as Xeloda® and is a prodrug said to achieve selective delivery of 5-fluorouracil (5-FU, 1) to tumors by sequential activation of the prodrug with endogenous enzymes preferentially located in the human liver and tumor tissues see Fig. 1). Capecitabine was first approved in the US in 1998 for the treatment of metastatic breast cancer that is refractory to standard chemotherapy with paclitaxel and anthracycline-containing regimen; it has now been used for the treatment of metastatic breast and colorectal cancers in more than 70 countries. It was designed to achieve greater selectivity than its active form, 5-FU (1)


Thymidine Phosphorylase Cytidine Deaminase Dihydropyrimidine Dehydrogenase Bone Marrow Toxicity Pyrimidine Nucleoside 
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© American Association of Pharmaceutical Scientists 2007

Authors and Affiliations

  • Nobuo Shimma
    • 1
  1. 1.Kamakura Research LaboratoriesChugai Pharmaceutical Co. Ltd.KamakuraJapan

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