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. 2009 Nov 26;52(22):6958-61.
doi: 10.1021/jm901181h.

Synthesis, Crystallization, and Biological Evaluation of an Orally Active Prodrug of Gemcitabine

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Synthesis, Crystallization, and Biological Evaluation of an Orally Active Prodrug of Gemcitabine

David M Bender et al. J Med Chem. .

Abstract

The design, synthesis, and biological characterization of an orally active prodrug (3) of gemcitabine are described. Additionally, the identification of a novel co-crystal solid form of the compound is presented. Valproate amide 3 is orally bioavailable and releases gemcitabine into the systemic circulation after passing through the intestinal mucosa. The compound has entered clinical trials and is being evaluated as a potential new anticancer agent.

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