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

doi:10.1248/cpb.33.4870

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

Research output: Contribution to journal › Article › peer-review

26 Citations (Scopus)

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 language	English
Pages (from-to)	4870-4877
Number of pages	8
Journal	Chemical and Pharmaceutical Bulletin
Volume	33
Issue number	11
DOIs	https://doi.org/10.1248/cpb.33.4870
Publication status	Published - 1985
Externally published	Yes

All Science Journal Classification (ASJC) codes

Chemistry(all)
Drug Discovery

Access to Document

10.1248/cpb.33.4870

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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.",

author = "Fumio Sakamoto and Shoji Ikeda and Hirosato Kondo and Goro Tsukamoto",

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AU - Tsukamoto, Goro

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