Lipoglycopeptide
A glycopeptide antibiotic with an added lipophilic (fat-soluble) side chain that provides additional mechanisms of action, enhanced potency, and longer half-lives. Telavancin, dalbavancin, and oritavancin are approved lipoglycopeptides that build on the vancomycin glycopeptide scaffold.
Technical Context
Lipoglycopeptides combine the glycopeptide core (vancomycin-like binding to D-Ala-D-Ala) with a lipophilic side chain providing additional mechanisms: membrane anchoring (the lipid tail inserts into the bacterial membrane, positioning the glycopeptide for enhanced target access), membrane depolarisation (direct disruption of membrane potential), and increased membrane permeability. This dual mechanism (cell wall synthesis inhibition + membrane disruption) provides bactericidal activity against some organisms where vancomycin is only bacteriostatic. Pharmacokinetic advantages of lipophilicity: telavancin concentrates in epithelial lining fluid (relevant for pneumonia); dalbavancin has a half-life of ~14 days (enabling single-dose treatment); oritavancin has a half-life of ~245 hours with extensive tissue distribution. These PK properties reduce healthcare burden through less frequent dosing.