Literature DB >> 19116869

5'-O-D-valyl ara A, a potential prodrug for improving oral bioavailability of the antiviral agent vidarabine.

Wei Shen1, Jae-Seung Kim, Stefanie Mitchell, Phil Kish, Paul Kijek, John Hilfinger.   

Abstract

In order to improve the oral bioavailability of Adenine 9-beta-D-arabinofuranoside (n class="Chemical">Vidarabine, also called ara A), an antiviral drug which is active against herpes simplex and varicella zoster viruses and the first agent to be licensed for the treatment of systematic herpes virus infection in man, the corresponding 5'-O-D-valyl ester derivative has been synthesized. Based on their physicochemical properties, 5'-O-valyl ara A has emerged as a potential prodrug candidate to improve the oral bioavailability of vidarabine. We describe in this paper a facile synthesis route for the prodrug and its physicochemical properties.

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Year:  2009        PMID: 19116869      PMCID: PMC2642978          DOI: 10.1080/15257770802581757

Source DB:  PubMed          Journal:  Nucleosides Nucleotides Nucleic Acids        ISSN: 1525-7770            Impact factor:   1.381


  25 in total

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Authors:  A Hassner; G Strand; M Rubenstein; A Patchornik
Journal:  J Am Chem Soc       Date:  1975-03-19       Impact factor: 15.419

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Journal:  J Med Chem       Date:  1979-03       Impact factor: 7.446

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Authors:  W Plunkett; S S Cohen
Journal:  Ann N Y Acad Sci       Date:  1977-03-04       Impact factor: 5.691

4.  Herpes simplex encephalitis: vidarabine therapy and diagnostic problems.

Authors:  R J Whitley; S J Soong; M S Hirsch; A W Karchmer; R Dolin; G Galasso; J K Dunnick; C A Alford
Journal:  N Engl J Med       Date:  1981-02-05       Impact factor: 91.245

5.  Inhibition of drug metabolism by a prodrug: 9-beta-D-arabinofuranosyladenine 5'-valerate as an inhibitor of adenosine deaminase.

Authors:  R A Lipper; S M Machkovech; J C Drach; W I Higuchi
Journal:  Mol Pharmacol       Date:  1978-03       Impact factor: 4.436

6.  Amino acid ester prodrugs of floxuridine: synthesis and effects of structure, stereochemistry, and site of esterification on the rate of hydrolysis.

Authors:  Balvinder S Vig; Philip J Lorenzi; Sachin Mittal; Christopher P Landowski; Ho-Chul Shin; Henry I Mosberg; John M Hilfinger; Gordon L Amidon
Journal:  Pharm Res       Date:  2003-09       Impact factor: 4.200

7.  Adenine arabinoside therapy of biopsy-proved herpes simplex encephalitis. National Institute of Allergy and Infectious Diseases collaborative antiviral study.

Authors:  R J Whitley; S J Soong; R Dolin; G J Galasso; L T Ch'ien; C A Alford
Journal:  N Engl J Med       Date:  1977-08-11       Impact factor: 91.245

Review 8.  Human cytomegalovirus DNA replication: antiviral targets and drugs.

Authors:  Beatrice Mercorelli; Elisa Sinigalia; Arianna Loregian; Giorgio Palù
Journal:  Rev Med Virol       Date:  2008 May-Jun       Impact factor: 6.989

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Authors:  R J Whitley; A J Nahmias; S J Soong; G G Galasso; C L Fleming; C A Alford
Journal:  Pediatrics       Date:  1980-10       Impact factor: 7.124

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Journal:  Cancer Res       Date:  1975-06       Impact factor: 12.701

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  2 in total

1.  Chemoenzymatic syntheses and anti-HIV-1 activity of glucose-nucleoside conjugates as prodrugs.

Authors:  Tatiana Rodríguez-Pérez; Susana Fernández; Yogesh S Sanghvi; Mervi Detorio; Raymond F Schinazi; Vicente Gotor; Miguel Ferrero
Journal:  Bioconjug Chem       Date:  2010-11-15       Impact factor: 4.774

2.  Synthetic Analogues of Aminoadamantane as Influenza Viral Inhibitors-In Vitro, In Silico and QSAR Studies.

Authors:  Radoslav Chayrov; Nikolaos A Parisis; Maria V Chatziathanasiadou; Eleni Vrontaki; Kalliopi Moschovou; Georgia Melagraki; Hristina Sbirkova-Dimitrova; Boris Shivachev; Michaela Schmidtke; Yavor Mitrev; Martin Sticha; Thomas Mavromoustakos; Andreas G Tzakos; Ivanka Stankova
Journal:  Molecules       Date:  2020-09-01       Impact factor: 4.411

  2 in total

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