Identification

Name
Teicoplanin
Accession Number
DB06149
Type
Small Molecule
Groups
Approved, Investigational
Description

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.

Synonyms
  • Teichomycin A2
  • teicoplanina
  • téicoplanine
  • teicoplaninum
External IDs
Antibiotic 8327A / Antibiotic MDL 507 / MDL 507 / MDL-507
International/Other Brands
Targocid (Sanofi-Aventis)
Categories
UNII
4U3D3YY81M
CAS number
61036-62-2
Weight
Not Available
Chemical Formula
Not Available
InChI Key
Not Available
InChI
Not Available
IUPAC Name
Not Available
SMILES
Not Available

Pharmacology

Indication

For the treatment of bacterial infections caused by susceptible microorganisms.

Pharmacodynamics

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. 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 action

Teicoplanin inhibits peptidoglycan polymerization, resulting in inhibition of bacterial cell wall synthesis and cell death.

TargetActionsOrganism
AD-Ala-D-Ala moiety of NAM/NAG peptide subunits of peptidoglycan
inhibitor
Gram-positive bacteria
Absorption

Teicoplanin is poorly absorbed after oral administration but is 90% bioavailable when administered intramuscularly.

Volume of distribution
Not Available
Protein binding

90% to 95%

Metabolism

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 elimination
Not Available
Half life

70-100 hours

Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Gram-positive Bacteria
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of bleeding can be increased when Teicoplanin is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Teicoplanin is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Teicoplanin is combined with 4-hydroxycoumarin.
AcenocoumarolThe risk or severity of bleeding can be increased when Teicoplanin is combined with Acenocoumarol.
Adenovirus type 7 vaccine liveThe therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Teicoplanin.
Anthrax immune globulin humanThe therapeutic efficacy of Anthrax immune globulin human can be decreased when used in combination with Teicoplanin.
Anthrax vaccineThe therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Teicoplanin.
Bacillus calmette-guerin substrain connaught live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain connaught live antigen can be decreased when used in combination with Teicoplanin.
Bacillus calmette-guerin substrain danish 1331 live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain danish 1331 live antigen can be decreased when used in combination with Teicoplanin.
Bacillus calmette-guerin substrain tice live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain tice live antigen can be decreased when used in combination with Teicoplanin.
Food Interactions
Not Available

References

Synthesis Reference

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

US5612459
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
KEGG Drug
D02142
KEGG Compound
C15820
PubChem Substance
46507509
ChEBI
29687
PharmGKB
PA164746244
Wikipedia
Teicoplanin
ATC Codes
J01XA02 — Teicoplanin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1WithdrawnPreventionNeurosurgery1
2CompletedTreatmentOsteoarticular Infections1
2CompletedTreatmentOsteomyelitis1
3TerminatedTreatmentSkin Diseases, Infectious / Soft Tissues Infections1
4CompletedPreventionTotal Hip and Knee Arthroplasties1
4CompletedTreatmentInfection NOS / Neutropenia, Febrile1
4Unknown StatusTreatmentAmputation Wound / Wound Infections1
4Unknown StatusTreatmentInfection caused by staphylococci1
Not AvailableCompletedNot AvailableAllogenic Blood Stem Cell Transplantation / Neutropenia, Febrile1
Not AvailableNot Yet RecruitingNot AvailableInfectious Diseases1
Not AvailableRecruitingTreatmentChronic Skin Ulcers1
Not AvailableRecruitingTreatmentProsthetic Joint Infection1
Not AvailableUnknown StatusSupportive CareInfection NOS1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
Not Available
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Classification
Not classified

Targets

1. D-Ala-D-Ala moiety of NAM/NAG peptide subunits of peptidoglycan
Kind
Group
Organism
Gram-positive bacteria
Pharmacological action
Yes
Actions
Inhibitor
References
  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]

Drug created on December 05, 2007 01:57 / Updated on November 02, 2018 06:14