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Teicoplanin



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. Its mechanism of action is to inhibit bacterial cell wall synthesis. Teicoplanin is marketed by Aventis under the trade name Targocid®.

Additional recommended knowledge

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 RS-1 through RS-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.

 

References

  1. ^ 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.
  2. ^ 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.
  3. ^ 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.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Teicoplanin". A list of authors is available in Wikipedia.
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