Chemical Identity

Property	Value
Chemical Formula	C88H100Cl2N10O28
Molecular Weight	1816.7 Da
CAS Number	171500-79-1
Peptide Class	Lipoglycopeptide
Origin	Semi-synthetic (from teicoplanin aglycone)

Structure

Dalbavancin is a semi-synthetic lipoglycopeptide derived from the teicoplanin-like glycopeptide A-40926 produced by Nonomuraea species. It retains the heptapeptide core with three fused aromatic rings and features a lipophilic decyl side chain and a modified sugar that enhances membrane binding and prolongs half-life.

Mechanism of Action

Dalbavancin binds to D-Ala-D-Ala of lipid II, inhibiting cell wall transglycosylation and transpeptidation. The lipophilic tail anchors to the bacterial membrane, creating a local high-concentration effect. It maintains activity against vancomycin-intermediate Staphylococcus aureus (VISA) strains.

Clinical Applications

• Acute bacterial skin and skin structure infections (ABSSSI): FDA-approved
• MRSA infections: Alternative to vancomycin
• Streptococcal infections: Group A strep, pneumococcus
• Osteomyelitis: Off-label for long-duration therapy

Pharmacokinetics

• Half-life: 346 hours (~14 days)
• Protein binding: 93%
• Elimination: Renal (33% unchanged)
• Dosing: Single 1500 mg IV dose or 1000 mg + 500 mg one week apart
• Route: IV infusion over 30 minutes

Safety and Side Effects

Nausea (3%), diarrhea (2%), headache (2%), and infusion site reactions. No significant hepatotoxicity or nephrotoxicity in clinical trials. Avoid in patients with severe renal impairment (CrCl <30 mL/min).

References

• Boucher, H.W., et al. (2014). Once-weekly dalbavancin versus daily conventional therapy for skin infection. New England Journal of Medicine, 370, 2169-2179.
• Dunne, M.W., et al. (2016). DISCOVER 1 and 2 trials. Clinical Infectious Diseases, 62, S46-S52.