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Literature DB >> 19860433

Synthesis, crystallization, and biological evaluation of an orally active prodrug of gemcitabine.

David M Bender¹, Jingqi Bao, Anne H Dantzig, William D Diseroad, Kevin L Law, Nicholas A Magnus, Jeffrey A Peterson, Everett J Perkins, Yangwei J Pu, Susan M Reutzel-Edens, David M Remick, James J Starling, Gregory A Stephenson, Radhe K Vaid, Deyi Zhang, James R McCarthy.

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.

Entities: Chemical

Mesh：

Substances：

Year: 2009 PMID： 19860433 DOI： 10.1021/jm901181h

Source DB: PubMed Journal: J Med Chem ISSN： 0022-2623 Impact factor: 7.446

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Cited

21 in total

Review 1. Oral anticancer drugs: mechanisms of low bioavailability and strategies for improvement.

Authors: Frederik E Stuurman; Bastiaan Nuijen; Jos H Beijnen; Jan H M Schellens
Journal: Clin Pharmacokinet Date: 2013-06 Impact factor: 6.447

2. Amino Acid Promoieties Alter Valproic Acid Pharmacokinetics and Enable Extended Brain Exposure.

Authors: Mikko Gynther; Lauri Peura; Monika Vernerová; Jukka Leppänen; Jussi Kärkkäinen; Marko Lehtonen; Jarkko Rautio; Kristiina M Huttunen
Journal: Neurochem Res Date: 2016-07-14 Impact factor: 3.996

3. Encapsulating a Hydrophilic Chemotherapeutic into Rod-like Nanoparticles of a Genetically Encoded Asymmetric Triblock Polypeptide Improves its Efficacy.

Authors: Jayanta Bhattacharyya; Isaac Weitzhandler; Shihan Bryan Ho; Jonathan R McDaniel; Xinghai Li; Lei Tang; Jinyao Liu; Mark Dewhirst; Ashutosh Chilkoti
Journal: Adv Funct Mater Date: 2017-02-07 Impact factor: 18.808

4. Low-dose metronomic oral dosing of a prodrug of gemcitabine (LY2334737) causes antitumor effects in the absence of inhibition of systemic vasculogenesis.

Authors: Giulio Francia; Yuval Shaked; Kae Hashimoto; John Sun; Melissa Yin; Carolyn Cesta; Ping Xu; Shan Man; Christina Hackl; Julie Stewart; Mark Uhlik; Anne H Dantzig; F Stuart Foster; Robert S Kerbel
Journal: Mol Cancer Ther Date: 2011-12-21 Impact factor: 6.261

5. Phase I dose escalation and pharmacokinetic evaluation of two different schedules of LY2334737, an oral gemcitabine prodrug, in patients with advanced solid tumors.

Authors: Sandrine J Faivre; Anthony J Olszanski; Karin Weigang-Köhler; Hanno Riess; Roger B Cohen; Xuejing Wang; Scott P Myrand; Enaksha R Wickremsinhe; Candice L Horn; Haojun Ouyang; Sophie Callies; Karim A Benhadji; Eric Raymond
Journal: Invest New Drugs Date: 2015-09-16 Impact factor: 3.850

6. Stearoyl gemcitabine nanoparticles overcome resistance related to the over-expression of ribonucleotide reductase subunit M1.

Authors: Woon-Gye Chung; Michael A Sandoval; Brian R Sloat; Dharmika S P Lansakara-P; Zhengrong Cui
Journal: J Control Release Date: 2011-08-07 Impact factor: 9.776

Synthesis, crystallization, and biological evaluation of an orally active prodrug of gemcitabine.

Review 1. Oral anticancer drugs: mechanisms of low bioavailability and strategies for improvement.

2. Amino Acid Promoieties Alter Valproic Acid Pharmacokinetics and Enable Extended Brain Exposure.

3. Encapsulating a Hydrophilic Chemotherapeutic into Rod-like Nanoparticles of a Genetically Encoded Asymmetric Triblock Polypeptide Improves its Efficacy.

4. Low-dose metronomic oral dosing of a prodrug of gemcitabine (LY2334737) causes antitumor effects in the absence of inhibition of systemic vasculogenesis.

5. Phase I dose escalation and pharmacokinetic evaluation of two different schedules of LY2334737, an oral gemcitabine prodrug, in patients with advanced solid tumors.

6. Stearoyl gemcitabine nanoparticles overcome resistance related to the over-expression of ribonucleotide reductase subunit M1.

7. Phase I study of oral CP-4126, a gemcitabine derivative, in patients with advanced solid tumors.

8. Synthesis and cytostatic evaluation of 4-N-alkanoyl and 4-N-alkyl gemcitabine analogues.

9. 4-N-Alkanoyl and 4-N-alkyl gemcitabine analogues with NOTA chelators for 68-gallium labelling.

Review 10. Advances in the development of nucleoside and nucleotide analogues for cancer and viral diseases.