Chemical Identity

Property	Value
Chemical Formula	C80H106Cl2N11O27P
Molecular Weight	1755.6 Da
CAS Number	372151-71-8
Peptide Class	Lipoglycopeptide
Origin	Semi-synthetic (from vancomycin)

Structure

Telavancin is a semi-synthetic lipoglycopeptide derived from vancomycin with a decylaminoethyl lipophilic side chain attached to the vancosamine sugar and a hydrophilic phosphonate group on the disaccharide. The lipophilic tail enables membrane anchoring, while the phosphonate maintains aqueous solubility.

Mechanism of Action

Telavancin has dual mechanisms: (1) binding to D-Ala-D-Ala of lipid II to inhibit cell wall transglycosylation and transpeptidation, and (2) rapid depolarization of the bacterial membrane potential via the lipophilic side chain, leading to increased permeability and bacterial killing.

Clinical Applications

• Hospital-acquired pneumonia: Including MRSA-associated
• ABSSSI: Skin and soft tissue infections
• MRSA infections: Alternative to vancomycin
• Gram-positive bacteremia: When other options limited

Pharmacokinetics

• Half-life: 7-9 hours
• Protein binding: 90%
• Elimination: Renal (76% unchanged)
• Dosing: 10 mg/kg IV every 24 hours
• Route: IV infusion over 60 minutes

Safety and Side Effects

Nephrotoxicity (increased creatinine, especially with pre-existing renal disease), QTc prolongation, nausea, vomiting, taste disturbance, and foamy urine. Contraindicated with QTc prolongation or concurrent QT-prolonging drugs.

References

• Stryjewski, M.E., et al. (2008). Telavancin versus vancomycin for complicated skin infections. New England Journal of Medicine, 359, 858-860.
• Rubinstein, E., et al. (2014). Telavancin for hospital-acquired pneumonia. Clinical Infectious Diseases, 59, 1824-1832.