Teicoplanin

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Image:Teicoplanin.png
Teicoplanin
Systematic (IUPAC) name
?
Identifiers
CAS number	61036-62-2
ATC code	J01 XA02
PubChem	?
Chemical data
Formula	Variable
Mol. weight	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. (de Lalla, 1992)

1 Chemistry
- 1.1 Structure
2 References
3 Footnotes

[edit] Chemistry

[edit] Structure

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).<ref>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.</ref> 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.

Image:Teicoplanin core and major components.svg

[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.