Teicoplanin

Drugbox
IUPAC_name =

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CAS_number=61036-62-2
ATC_prefix=J01
ATC_suffix=XA02
ATC_supplemental=
PubChem=
DrugBank=
chemical_formula = Variable
molecular_weight = 1564.3 to 1907.7 g/mol
bioavailability= 90% (given IM)
metabolism = Nil
protein_bound = 90% to 95%
elimination_half-life= 70 to 100 hours
excretion = Renal (97% unchanged)
pregnancy_AU = B3
legal_UK = POM
routes_of_administration= 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. [ cite journal | author = de Lalla F, Nicolin R, Rinaldi E, Scarpellini P, Rigoli R, Manfrin V, Tramarin A | title = Prospective study of oral teicoplanin versus oral vancomycin for therapy of pseudomembranous colitis and Clostridium difficile-associated diarrhea | journal = Antimicrob Agents Chemother | volume = 36 | issue = 10 | pages = 2192–6 | year = 1992 | pmid = 1444298]

Its strength is considered to be due to the length of the hydrocarbon chain. [cite web | author=Gilpin M, Milner P | title=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 ? | url=http://www.chemsoc.org/chembytes/ezine/1997/resist.htm | year=1997 | publisher=Royal Society of Chemistry | accessdate-2006-10-15 - includes picture of Teicoplanin's structure.]

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). [cite journal | author = Bernareggi A, Borghi A, Borgonovi M, Cavenaghi L, Ferrari P, Vékey K, Zanol M, Zerilli L | title = Teicoplanin metabolism in humans | journal = Antimicrob Agents Chemother | volume = 36 | issue = 8 | pages = 1744–9 | year = 1992 | pmid = 1416858 | url = http://www.pubmedcentral.nih.gov/pagerender.fcgi?artid=192040] 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