Studies on Prodrugs. IV. Preparation and Characterization of N-(5-Substituted 2-oxo-l,3-dioxol-4-yl)methyl Norfloxacin

Fumio Sakamoto, Shoji Ikeda, Hirosato Kondo, Goro Tsukamoto

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Abstract

As a new type of norfloxacin (NFLX) prodrug, N-(5-substituted 2-oxo-l, 3-dioxol-4-yl)methyl NFLXs were designed. These N-masked NFLXs were prepared and confirmed to produce higher NFLX levels in blood than NFLX itself after oral administration to mice. N-(5-Methyl-2-oxo-l,3-dioxol-4-yl)methyl NFLX was found to be smoothly hydrolyzed in mouse blood in vitro, and when administered orally, gave about 5-fold higher blood levels of NFLX than NFLX itself. Thus, the (5-methyl-2-oxo-l,3-dioxol-4-yl)methyl group was confirmed to function as an amine-type promoiety.

Original languageEnglish
Pages (from-to)4870-4877
Number of pages8
JournalChemical and Pharmaceutical Bulletin
Volume33
Issue number11
DOIs
Publication statusPublished - Jan 1 1985
Externally publishedYes

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All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Drug Discovery

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