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Accession NumberDB06149

Teicoplanin is a glycopeptide antibiotic. It is a mixture of several compounds, five major (named teicoplanin A2-1 through A2-5) and four minor (named teicoplanin RS-1 through RS-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. [Wikipedia]

Protein structureDb06149
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Protein chemical formulaC88H97Cl2N9O33
Protein average weight1879.658 Da
SequencesNot Available
Teichomycin a2 factor 2
External Identifiers
  • Antibiotic 8327A
  • Antibiotic MDL 507
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
Brand mixturesNot Available
SaltsNot Available
CAS number61036-62-2
DescriptionNot Available
KingdomOrganic Compounds
Super ClassOrganic Acids
ClassCarboxylic Acids and Derivatives
Sub ClassAmino Acids, Peptides, and Analogues
Direct ParentPeptides
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkNot Available
External DescriptorsNot Available
IndicationFor the treatment of bacterial infections caused by susceptible microorganisms.
PharmacodynamicsTeicoplanin 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. Oral teicoplanin has been demonstrated to be effective in the treatment of pseudomembranous colitis and Clostridium difficile-associated diarrhoea, with comparable efficacy to vancomycin.
Mechanism of actionTeicoplanin inhibits peptidoglycan polymerization, resulting in inhibition of bacterial cell wall synthesis and cell death.
Related Articles
AbsorptionTeicoplanin is poorly absorbed after oral administration but is 90% bioavailable when administered intramuscularly.
Volume of distributionNot Available
Protein binding90% to 95%

Two metabolites (metabolites 1 and 2; 2 to 3% of total teicoplanin) have been isolated after intravenous administration of radiolabeled teicoplanin. After purification, their structures were found to be new teicoplanin-like molecules, bearing 8-hydroxydecanoic and 9-hydroxydecanoic acyl moieties. This metabolic transformation is likely due to hydroxylation in the omega-2 and omega-1 positions for metabolites 1 and 2, respectively, of the C-10 linear side chain of component A2-3. This might explain the low extent of metabolism of teicoplanin if we consider that only component A2-3 has a linear chain that is susceptible to such oxidation.

Route of eliminationNot Available
Half life70-100 hours
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Gram-positive Bacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Experimental PropertiesNot Available
Synthesis Reference

Emil Toma, Madeleine Ravaoarinoro, “Production and characteristics of anti-teicoplanin polyclonal antibody.” U.S. Patent US5612459, issued November, 1990.

General References
  1. de Lalla F, Nicolin R, Rinaldi E, Scarpellini P, Rigoli R, Manfrin V, Tramarin A: Prospective study of oral teicoplanin versus oral vancomycin for therapy of pseudomembranous colitis and Clostridium difficile-associated diarrhea. Antimicrob Agents Chemother. 1992 Oct;36(10):2192-6. [PubMed:1444298 ]
  2. Bernareggi A, Borghi A, Borgonovi M, Cavenaghi L, Ferrari P, Vekey K, Zanol M, Zerilli LF: Teicoplanin metabolism in humans. Antimicrob Agents Chemother. 1992 Aug;36(8):1744-9. [PubMed:1416858 ]
  3. Yano R, Nakamura T, Tsukamoto H, Igarashi T, Goto N, Wakiya Y, Masada M: Variability in teicoplanin protein binding and its prediction using serum albumin concentrations. Ther Drug Monit. 2007 Aug;29(4):399-403. [PubMed:17667792 ]
  4. Pryka RD, Rodvold KA, Rotschafer JC: Teicoplanin: an investigational glycopeptide antibiotic. Clin Pharm. 1988 Sep;7(9):647-58. [PubMed:2977108 ]
External Links
ATC CodesJ01XA02
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Drug InteractionsNot Available
Food InteractionsNot Available


1. D-Ala-D-Ala moiety of NAM/NAG peptide subunits of peptidoglycan
Gram-positive bacteria
Pharmacological action
  1. Lundstrom TS, Sobel JD: Antibiotics for gram-positive bacterial infections. Vancomycin, teicoplanin, quinupristin/dalfopristin, and linezolid. Infect Dis Clin North Am. 2000 Jun;14(2):463-74. [PubMed:10829266 ]
  2. Reynolds PE: Structure, biochemistry and mechanism of action of glycopeptide antibiotics. Eur J Clin Microbiol Infect Dis. 1989 Nov;8(11):943-50. [PubMed:2532132 ]
  3. Reynolds PE, Somner EA: Comparison of the target sites and mechanisms of action of glycopeptide and lipoglycodepsipeptide antibiotics. Drugs Exp Clin Res. 1990;16(8):385-9. [PubMed:2151441 ]
  4. Boger DL: Vancomycin, teicoplanin, and ramoplanin: synthetic and mechanistic studies. Med Res Rev. 2001 Sep;21(5):356-81. [PubMed:11579438 ]
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Drug created on December 05, 2007 01:57 / Updated on March 14, 2016 10:03