Teicoplanin

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Teicoplanin
Systematic (IUPAC) name
?
Identifiers
CAS number	61036-62-2
ATC code	J01XA02
PubChem	?
Chemical data
Formula	Variable
Mol. mass	1564.3 to 1907.7 g/mol
Pharmacokinetic data
Bioavailability	90% (given IM)
Protein binding	90% to 95%
Metabolism	Nil
Half life	70 to 100 hours
Excretion	Renal (97% unchanged)
Therapeutic considerations
Pregnancy cat.	B3(AU)
Legal status	POM(UK)
Routes	Intravenous, intramuscular

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. 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.^[1]

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

[edit] 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.

Teicoplanin core (left, black) and side chains which characterize teicoplanins A_{2_{-1 through A₂-5 (right). In blue: β-D-glucosamine.}}

[edit] References

^ de Lalla F, Nicolin R, Rinaldi E, Scarpellini P, Rigoli R, Manfrin V, Tramarin A (1992). "Prospective study of oral teicoplanin versus oral vancomycin for therapy of pseudomembranous colitis and Clostridium difficile-associated diarrhea.". Antimicrob Agents Chemother 36 (10): 2192-6. PMID 1444298.
^ Gilpin M, Milner P (1997). Resisting changes -- Over the past 40 years the glycopeptide antibiotics have played a crucial role in treating bacterial infections. But how long can it continue ?. Royal Society of Chemistry. - includes picture of Teicoplanin's structure.
^ Bernareggi A, Borghi A, Borgonovi M, Cavenaghi L, Ferrari P, Vékey K, Zanol M, Zerilli L (1992). "Teicoplanin metabolism in humans". Antimicrob Agents Chemother 36 (8): 1744–9. PMID 1416858.