Historical background:
Macrolides are a class of antibiotics that were first discovered in the 1950s.
The first macrolide antibiotic, erythromycin, was isolated from a soil sample in the Philippines.
Since then, many other macrolides have been developed and are widely used in medicine.
Nomenclature:
The name "macrolide" comes from the large ring structure that is common to all members of this class of antibiotics.
The chemical names of individual macrolides vary, but they are all characterized by the presence of this ring structure.
Stereochemistry:
Macrolides are often chiral compounds, meaning they have two enantiomers that are mirror images of each other.
The activity of different enantiomers can vary, and some macrolides are administered as specific enantiomers.
Structure activity relationship:
The structure activity relationship (SAR) of macrolides is complex and involves multiple factors, including the size and shape of the macrocycle, the functional groups attached to the macrocycle, and the degree of hydrophobicity or hydrophilicity of the molecule.
Modifications to these factors can lead to changes in the spectrum of activity, potency, and pharmacokinetic properties of the antibiotic.
Chemical degradation classification:
Macrolides are generally stable in acidic conditions but can be hydrolyzed under basic conditions.
They are also sensitive to oxidative degradation.
Important products:
The most commonly used macrolide antibiotics include erythromycin, clarithromycin, and azithromycin.
These antibiotics are used to treat a wide range of bacterial infections, including respiratory tract infections, skin and soft tissue infections, and sexually transmitted infections.
Macrolides are also used as prophylactic agents to prevent bacterial endocarditis in patients with certain heart conditions.
