Teicoplanin
995332
223387679
2008-07-03T21:25:41Z
DOI bot
6652755
Citation maintenance. Formatted: title. You can [[WP:DOI|use this bot]] yourself! Please [[User:DOI_bot/bugs|report any bugs]].
{{Drugbox|
|IUPAC_name =
| image = Teicoplanin core and major components.svg
| 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 [[Intramuscular injection|IM]])
| metabolism = Nil
| protein_bound = 90% to 95%
| elimination_half-life= 70 to 100 hours
| excretion = [[Kidney|Renal]] (97% unchanged)
| pregnancy_AU = B3
| legal_UK = POM
| routes_of_administration= [[Intravenous therapy|Intravenous]], intramuscular
}}
'''Teicoplanin''' is an [[antibiotic]] used in the [[prophylaxis]] and treatment of serious infections caused by [[Gram-positive]] [[bacterium|bacteria]], including [[methicillin-resistant Staphylococcus aureus|methicillin-resistant ''Staphylococcus aureus'']] and ''[[Enterococcus faecalis]]''. It is a glycopeptide antiobiotic extracted from ''[[Actinoplanes|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 diarrhoea, with comparable efficacy to vancomycin.<ref> {{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}}</ref>
Its strength is considered to be due to the length of the hydrocarbon chain.<ref>{{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.</ref>
==Chemistry==
Teicoplanin is actually a mixture of several compounds, five major (named '''teicoplanin A<sub>2</sub>-1''' through '''A<sub>2</sub>-5''') and four minor (named '''teicoplanin R<sub>S</sub>-1''' through '''R<sub>S</sub>-4''').<ref>{{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}}</ref>
All teicoplanins share a same [[glycopeptide antibiotic|glycopeptide]] core, termed '''teicoplanin A<sub>3</sub>-1''' — a [[macrocycle|fused ring]] structure to which two [[carbohydrate]]s ([[mannose]] and [[N-Acetylglucosamine|''N''-acetylglucosamine]]) are attached. The major and minor components also contain a third carbohydrate [[moiety]] — [[glucosamine|β-<small>D</small>-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.
{{clear}}
[[Image:Teicoplanin core and major components.svg|thumb|center|700px|Teicoplanin core (left, black) and side chains which characterize teicoplanins A<sub>2</sub>-1 through A<sub>2</sub>-5 (right). In {{fontcolor|#0053bd|blue}}: [[glucosamine|β-<small>D</small>-glucosamine]].]]
==References==
{{Reflist|2}}
{{Other antibacterials}}
[[Category:glycopeptide antibiotics]]
{{antibiotic-stub}}
[[es:Teicoplanina]]
[[pl:Teikoplanina]]