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Macrolide antibiotics, 16-membered metabolism

Erythromycin was discovered in 1952 in the metabolic products of a strain of Streptomyces erythreus. Clarithromycin and azithromycin are semisynthetic derivatives of erythromycin. Macrolide antibiotics contain a many-membered lactone ring (14-membered rings for erythromycin and clarithromycin, and a 15-membered ring for azithromycin) to which are attached one or more deoxy sugars. Clarithromycin differs from erythromycin only by methylation of the hydroxyl group at the 6 position, and azithromycin differs by the addition of a methyl-substituted... [Pg.239]

Several 16-membered macrolides form metabolites which retain antimicrobial activity. As discussed above, 3"-esters such as rokitamycin and miokamycin produce prolonged concentrations of antibiotic in vivo due to the facile 3"- to 4"-0-acyl migration that follows enzymatic removal of the original 4 -ester [34, 269, 270], Following a different approach to overcome the lability of 4"-esters, specific 4"-0-acyl derivatives of tylosin were selected from the series of esters (15) based upon their greater stability toward liver enzymes [80], Although esterases play the most prominent role in metabolism of 16-membered macrolides, other mechanisms such as oxidative hydroxylation, A-demethylation, reduction, and hydrolysis of sugars have been reported for various compounds [91, 96, 115, 259, 270-272]. [Pg.283]


See other pages where Macrolide antibiotics, 16-membered metabolism is mentioned: [Pg.77]    [Pg.316]    [Pg.27]    [Pg.131]    [Pg.566]    [Pg.479]    [Pg.75]    [Pg.715]    [Pg.172]    [Pg.100]    [Pg.285]    [Pg.211]    [Pg.11]   
See also in sourсe #XX -- [ Pg.282 ]




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