| Deglycosylation of antiherpesviral 5-substituted arabinosyluracil derivatives by rat liver extract and enterobacteria cells. | |
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MedLine Citation:
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PMID: 7702634 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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A number of antiherpesviral 5-substituted derivatives of 1-beta-D-arabinofuranosyluracil (araU) were significantly resistant to phosphorolysis by rat liver extract (S-9), but were gradually deglycosylated in a 2% enterobacteria cell suspension. The relative order of the resistance conferred by the different C-5 substituents was: 5-propynyl > 5-(E)-2-bromovinyl > 5-(E)-2-chlorovinyl > 5-methyl > 5-iodo. The 2'-fluoro derivatives of araU were completely resistant to phosphorolysis by both liver extract and enterobacteria, whereas the corresponding ribofuranosyl and 2'-deoxyribofuranosyl nucleosides were easily phosphorolysed by S-9, and were immediately cleaved in a 1% enterobacteria cell suspension. These findings suggest that antiherpesviral 5-substituted araU analogues can be relatively stable in vivo, when injected intravenously, and that degradation of 1-beta-D-arabinofuranosyl-5-(E-2-bromovinyl)uracil (sorivudine) following oral administration is due primarily to the action of enterobacteria. |
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Authors:
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H Machida; Y Watanabe; F Kano; S Sakata; M Kumagai; T Yamaguchi |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: Biochemical pharmacology Volume: 49 ISSN: 0006-2952 ISO Abbreviation: Biochem. Pharmacol. Publication Date: 1995 Mar |
Date Detail:
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Created Date: 1995-05-02 Completed Date: 1995-05-02 Revised Date: 2003-11-14 |
Medline Journal Info:
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Nlm Unique ID: 0101032 Medline TA: Biochem Pharmacol Country: ENGLAND |
Other Details:
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Languages: eng Pagination: 763-6 Citation Subset: IM |
Affiliation:
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Biology Laboratory, R & D Division, Yamasa Corporation, Choshi, Japan. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Animals Antiviral Agents / metabolism*, pharmacology Arabinofuranosyluracil / analogs & derivatives*, metabolism, pharmacology Biotransformation Glycosylation Herpesvirus 1, Human / drug effects Herpesvirus 3, Human / drug effects Klebsiella pneumoniae / metabolism* Liver / metabolism* Rats |
| Chemical | |
Reg. No./Substance:
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0/Antiviral Agents; 3083-77-0/Arabinofuranosyluracil |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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