Teicoplanin

Teicoplanin
Clinical data
Pronunciation	/ˌtaɪkoʊˈpleɪnɪn/; TY-koh-PLAY-nin
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); EU: Rx-only;
Pharmacokinetic data
Bioavailability	90% (given IM)
Protein binding	90% to 95%
Metabolism	Nil
Elimination half-life	70 to 100 hours
Excretion	Kidney (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 ;
PubChem CID	16129712;
DrugBank	DB06149 ;
ChemSpider	16736197 ;
UNII	4U3D3YY81M;
KEGG	D02142 ;
ChEMBL	ChEMBL415428 ;
NIAID ChemDB	007693;
CompTox Dashboard (EPA)	DTXSID4048642 ;
Chemical and physical data
Formula	Variable
Molar mass	1564.3 to 1907.7 g/mol
Melting point	260 °C (500 °F) (dec.)
	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 ; Key:FHBQKTSCJKPYIO-OXIGXJDJSA-N ;
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Teicoplanin is an semisynthetic glycopeptide antibiotic with a spectrum of activity similar to vancomycin. Its mechanism of action is to inhibit bacterial cell wall peptidoglycan synthesis. It is used in the prophylaxis and treatment of serious infections caused by Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus and Enterococcus faecalis.

Teicoplanin is marketed by Sanofi-Aventis under the trade name Targocid. Other trade names include Ticocin 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 is produced by so-called "rare" actinobacterium Actinoplanes teichomyceticus ATCC 31121, belonging to the Micromonosporaceae family. Biosynthetic pathway leading to teicoplanin, as well as the regulatory circuit governing the biosynthesis, were studied intensively in recent years allowing to construct an integrated model of the biosynthesis.

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