Teicoplanin

Teicoplanin
Clinical data

Trade names	Targocid
AHFS/Drugs.com	International Drug Names
Pregnancy category	AU: B3
Routes of administration	Intravenous, intramuscular
ATC code	J01XA02 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only)
Pharmacokinetic data
Bioavailability	90% (given IM)
Protein binding	90% to 95%
Metabolism	Nil
Biological half-life	70 to 100 hours
Excretion	Renal (97% unchanged)
Identifiers
IUPAC name Ristomycin A 34-O-[2-(acetylamino)-2-deoxy-.beta.-D-glucopyranosyl]-22,31-dichloro-7-demethyl-64-O-demethyl-19-deoxy-56-O-[2-deoxy-2-[(8-methyl-1-oxononyl)amino]-.beta.-D-glucopyranosyl]-42-O-.alpha.-D-mannopyranosyl-
CAS Number	61036-62-2^Y
PubChem CID	16129712
DrugBank	DB06149^Y
ChemSpider	16736197^Y
UNII	4U3D3YY81M
KEGG	D02142^Y
ChEMBL	CHEMBL415428^N
NIAID ChemDB	007693
Chemical and physical data
Formula	Variable
Molar mass	1564.3 to 1907.7 g/mol
InChI InChI=1S/C89H99Cl2N9O33/c1-34(2)9-7-5-4-6-8-10-61(109)95-69-75(114)72(111)59(32-102)130-88(69)133-79-56-26-41-27-57(79)127-53-18-14-39(24-48(53)91)78(132-87-68(93-35(3)104)74(113)71(110)58(31-101)129-87)70-85(122)99-67(86(123)124)46-29-43(106)30-55(128-89-77(116)76(115)73(112)60(33-103)131-89)62(46)45-23-38(13-15-50(45)107)64(82(119)100-70)97-84(121)66(41)98-83(120)65-40-21-42(105)28-44(22-40)125-54-25-37(12-16-51(54)108)63(92)81(118)94-49(80(117)96-65)20-36-11-17-52(126-56)47(90)19-36/h11-19,21-30,34,49,58-60,63-78,87-89,101-103,105-108,110-116H,4-10,20,31-33,92H2,1-3H3,(H,93,104)(H,94,118)(H,95,109)(H,96,117)(H,97,121)(H,98,120)(H,99,122)(H,100,119)(H,123,124)/t49-,58-,59-,60-,63+,64-,65+,66-,67-,68-,69-,70+,71-,72-,73-,74-,75-,76+,77+,78-,87+,88+,89+/m1/s1^Y Key:FHBQKTSCJKPYIO-OXIGXJDJSA-N^Y
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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 semisynthetic glycopeptide antibiotic with a spectrum of activity similar to vancomycin. Its mechanism of action is to inhibit bacterial cell wall synthesis.

Teicoplanin is marketed by Sanofi-Aventis under the trade name Targocid. Other trade names include Ticosin marketed by Cipla(India).

Oral teicoplanin has been demonstrated to be effective in the treatment of pseudomembranous colitis and Clostridium difficile-associated diarrhoea, with comparable efficacy with vancomycin.

Its strength is considered to be due to the length of the hydrocarbon chain.

Teicoplanin targets peptidoglycan synthesis making it an effective antimicrobial against Gram-positive bacteria including Staphylococci and Clostridium spp. The following represents MIC susceptibility data for a few medically significant pathogens:

Teicoplanin (TARGOCID, marketed by Sanofi Aventis Ltd) 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). 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.

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Wikipedia