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

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 - Jan 1 1985
Externally published	Yes

Fingerprint

All Science Journal Classification (ASJC) codes

Chemistry(all)
Drug Discovery

Cite this

Sakamoto, F., Ikeda, S., Kondo, H., & Tsukamoto, G. (1985). Studies on Prodrugs. IV. Preparation and Characterization of N-(5-Substituted 2-oxo-l,3-dioxol-4-yl)methyl Norfloxacin. Chemical and Pharmaceutical Bulletin, 33(11), 4870-4877. https://doi.org/10.1248/cpb.33.4870

@article{d17514e6551842fda6922cd82f195f13,

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

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",

year = "1985",

month = "1",

day = "1",

doi = "10.1248/cpb.33.4870",

language = "English",

volume = "33",

pages = "4870--4877",

journal = "Chemical and Pharmaceutical Bulletin",

issn = "0009-2363",

publisher = "The Pharmaceutical Society of Japan",

number = "11",

}

TY - JOUR

T1 - Studies on Prodrugs. IV. Preparation and Characterization of N-(5-Substituted 2-oxo-l,3-dioxol-4-yl)methyl Norfloxacin

AU - Sakamoto, Fumio

AU - Ikeda, Shoji

AU - Kondo, Hirosato

AU - Tsukamoto, Goro

PY - 1985/1/1

Y1 - 1985/1/1

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=0022377168&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0022377168&partnerID=8YFLogxK

U2 - 10.1248/cpb.33.4870

DO - 10.1248/cpb.33.4870

M3 - Article

C2 - 3830420

AN - SCOPUS:0022377168

VL - 33

SP - 4870

EP - 4877

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

SN - 0009-2363

IS - 11

ER -

Access to Document

10.1248/cpb.33.4870