Macrolides
- BP-S-6-MEDICINAL_CHEMISTRY
- Mar 28
- 1 min read
Historical Background
First discovered in 1952 (Erythromycin from Saccharopolyspora erythraea).
Used for respiratory infections and atypical bacteria.
Nomenclature
Named after the macrocyclic lactone ring.
Examples:
Erythromycin
Clarithromycin
Azithromycin
Stereochemistry
14-, 15-, or 16-membered lactone rings.
Various sugar moieties (e.g., desosamine, cladinose).
Structure-Activity Relationship (SAR)
Lactone ring size: Affects ribosomal binding.
Sugar modifications:
Improve acid stability (Clarithromycin, Azithromycin).
Enhance bioavailability.
C-9 modifications: Affect efflux pump resistance.
Chemical Degradation Classification
Acid instability: Leads to inactive ketal products (Erythromycin).
Hydrolysis of lactone ring.
Oxidative degradation.
Important Products
Erythromycin (first macrolide).
Clarithromycin (acid-stable, better absorption).
Azithromycin (long half-life, broad spectrum).
Roxithromycin (enhanced tissue penetration).
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