Glycopeptide antibiotics

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Information about Glycopeptide antibiotics[edit source]

Introduction The glycopeptide antibiotics are semisynthetic macromolecules that are structurally related to vancomycin and have antibacterial activity against several gram positive organisms including methicillin resistant Staphylococcus aureus (MRSA). Three lipoglycopeptide antibiotics are available for use in the United States: dalbavancin, oritavancin and telavancin. All three agents have been associated with transient serum enzyme elevations during therapy, but they have yet to be linked convincingly to cases of clinically apparent acute liver injury.

Mechanism of action of Glycopeptide antibiotics[edit source]

The glycopeptide antibiotics are a class of antimicrobial agents that share a similar, macromolecular structure and basic mechanism of action. The lipoglycopeptides are largely synthetic derivatives of vancomycin modified to have greater potency or better pharmacokinetics and tolerance. Like vancomycin, these agents have potent antibacterial activity against several Streptococcus and Enterococcus species as well as Staphylococcus aureus, including strains that are methicillin-resistant (MRSA). The agents are macromolecular glycopeptides that act by binding to nascent bacterial cell wall peptidoglycans, thus interfering with cell wall synthesis. The lipoglycopeptides are not absorbed orally and have a prolonged half-life when given intravenously which allows for once daily and, in some cases, once weekly administration. Vancomycin is a similar glycopeptide, but its indications, wide scale use and record of safety are greater than the more recently approved lipoglycopeptide derivatives.

History of Glycopeptide antibiotics[edit source]

Three lipoglycopeptide antibiotics have been approved for use in the United States and are discussed together: telavancin (2009), dalbavancin (2014) and oritavancin (2014).

Telavancin[edit | edit source]

Telavancin (tel" a van' sin) is a macromolecular semisynthetic lipoglycopeptide with potent antimicrobial activity against several gram positive organisms including Staphylococcus aureus. The activity of telavancin against methicillin-resistant S. aureus (MRSA) infections has made it a valuable agent in the management of community and nosocomial acquired severe MRSA related infections. Telavancin was approved for use in the United States in 2009 for severe infections of the skin and skin structures due to susceptible organisms, and the indications were subsequently broadened to therapy of severe nosocomial pneumonia. Telavancin is available in solution in single use vials of 250 and 750 mg under the commercial name Vibativ. The recommended dose in adults is 10 mg/kg intravenously given over a 60 minute period once daily for 7 to 21 days. Side effects include infusion reactions, nausea, diarrhea, taste disturbance and foamy urine. Telavancin can also cause renal dysfunction and prolongation of the QTc interval. Rare side effects include hypersensitivity reactions, renal failure and Clostridium difficile (pseudomembranous) colitis.

Dalbavancin[edit | edit source]

Dalbavancin (dal" ba van' sin) is a macromolecular semisynthetic lipoglycopeptide with potent spectrum of antimicrobial activity against several gram positive organisms including Staphylococcus aureus. The activity of dalbavancin against MRSA infections has made it a valuable agent in the management of community and nosocomial acquired severe MRSA related infections. Dalbavancin was approved for use in the United States in 2014 for severe skin and skin structure infections due to susceptible organisms including MRSA. It is available as a powder for suspension in vials of 500 mg under the commercial name Dalvance. The recommended dose in adults is a single infusion of 1000 mg given intravenously over a 30 minute period, followed one week later by 500 mg intravenously. It can also be given as a single 1500 mg intravenous infusion. Side effects can include infusion reactions (“red man syndrome”), headache, nausea, diarrhea, rash and pruritus. Rare side effects include hypersensitivity reactions and Clostridium difficile (pseudomembranous) colitis.

Oritavancin[edit | edit source]

Oritavancin (or it" a van' sin) is a macromolecular semisynthetic lipoglycopeptide with potent antimicrobial activity against several gram positive organisms including Staphylococcus aureus. The activity of oritavancin against MRSA infections has made it a valuable agent in the management of community and nosocomial acquired severe MRSA-related infections. Oritavancin was approved for use in the United States in 2014 for severe skin and skin structure infections due to susceptible organisms including MRSA. It is available as a sterile powder for suspension in single use vials of 400 mg under the commercial name Orbactiv. The recommended dose in adults is a single infusion of 1200 mg intravenously over a 3 hour period. Side effects include infusion reactions, headache, nausea, diarrhea, skin rash and pruritus. Rare side effects include hypersensitivity reactions and Clostridium difficile (pseudomembranous) colitis.

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Contributors: Prab R. Tumpati, MD