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Teicoplanin
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| Systematic (IUPAC) name | |
| ? | |
| Identifiers | |
| CAS number | |
| ATC code | J01 |
| 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 | |
| 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 Sanofi-Aventis under the trade name Targocid.
Oral teicoplanin has been demonstrated to be effective in the treatment of pseudomembranous colitis and Clostridium difficile-associated diarrhea, 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
- ^ 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.
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Wikipedia content modification information:
- This page was last modified on 7 October 2008, at 17:32.
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