Teicoplanin

Teicoplanin

Clinical data
Pregnancy category	AU: B3
Routes of administration	Intravenous, intramuscular
ATC code	J01XA02 (WHO)
Legal status
Legal status	UK: POM (Prescription only)
Pharmacokinetic data
Bioavailability	90% (given IM)
Protein binding	90% to 95%
Metabolism	Nil
Elimination half-life	70 to 100 hours
Excretion	Renal (97% unchanged)
Identifiers
CAS Number	61036-62-2
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	Variable
Molar mass	1564.3 to 1907.7 g/mol

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Overview

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®.

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

Its strength is considered to be due to the length of the hydrocarbon chain.

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). 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.