Dirithromycin (also known as LY-237216) is an Erythromycin derivative acting as a potent and orally bioactive semi-synthetic macrolide glycopeptide antibiotic, working by binding to the 50S subunit of the 70S bacterial ribosome to inhibit the translocation of peptides. Dirithromycin is a more lipid-soluble prodrug derivative of 9S-erythromycyclamine prepared by condensation of the latter with 2-(2-methoxyethoxy)acetaldehyde. The 9N, 11O-oxazine ring thus formed is a hemi-aminal that is unstable under both acidic and alkaline aqueous conditions and undergoes spontaneous hydrolysis to form erythromycyclamine.