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Design, synthesis, and evaluation of stable and taste-free erythromycin proprodrugs.

Abstract：

:Erythromycin A is normally formulated for children as its 2'-ethyl succinate, a taste-free prodrug. Unfortunately, the prodrug hydrolyzes at a measurable rate in the medicine bottle, leading to the vile-tasting erythromycin. We have prepared derivatives of erythromycin B as putative paediatric prodrugs, taking advantage of the much improved acid stability of erythromycin B relative to erythromycin A. Thus, erythromycin B enol ether ethyl succinate is very poorly soluble in water, and its hydrolysis is undetectable in conditions resembling the medicine bottle. In acid, however, it converts rapidly to erythromycin B 2'-ethyl succinate, and this is in turn hydrolyzed to erythromycin B in neutral and basic conditions. Derivatives of erythromycin B enol ether are therefore proposed as taste-free proprodrugs of erythromycin B.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Bhadra PK,Morris GA,Barber J

doi

10.1021/jm049155y

keywords:

subject

Has Abstract

pub_date

2005-06-02 00:00:00

pages

3878-84

issue

11

eissn

0022-2623

issn

1520-4804

journal_volume

48

pub_type

杂志文章

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