Teicoplanin

Teicoplanin is an antibiotic used in the prophylaxis and treatment of serious infections caused by Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus and Enterococcus faecalis. It is a glycopeptide antiobiotic extracted from Actinoplanes teichomyceticus, with a similar spectrum of activity to vancomycin. Its mechanism of action is to inhibit bacterial cell wall synthesis. Teicoplanin is marketed by Aventis under the trade name Targocid®.

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Oral teicoplanin has been demonstrated to be effective in the treatment of pseudomembranous colitis and Clostridium difficile-associated diarrhoea, with comparable efficacy to vancomycin.^[1]

Its strength is considered to be due to the length of the hydrocarbon chain.^[2]

Chemistry

Teicoplanin is actually a mixture of several compounds, five major (named teicoplanin A₂-1 through A₂-5) and four minor (named teicoplanin R_S-1 through R_S-4).^[3] All teicoplanins share a same glycopeptide core, termed teicoplanin A₃-1 — a fused ring structure to which two carbohydrates (mannose and N-acetylglucosamine) are attached. The major and minor components also contain a third carbohydrate moiety — β-D-glucosamine — and differ only by the length and conformation of a side chain attached to it.

The structures of the teicoplanin core and the side chains which characterize the five major teicoplanin compounds are shown below.

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