Teicoplanin

Identification

Summary

Teicoplanin is a glycopeptide antibiotic with a similar mechanism of action and spectrum of activity to vancomycin used to treat various infections caused by gram-positive bacteria.

Generic Name
Teicoplanin
DrugBank Accession Number
DB06149
Background

Teicoplanin is a glycopeptide antibiotic consisting of 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, teicoplanin A3-1, but differ in the length and conformation of side chains attached to their β-D-glucosamine moiety.

Type
Small Molecule
Groups
Approved, Investigational
Synonyms
  • Teichomycin A2
  • Teicoplanin
  • teicoplanina
  • téicoplanine
  • teicoplaninum
External IDs
  • Antibiotic 8327A
  • Antibiotic MDL 507
  • MDL 507
  • MDL-507

Pharmacology

Indication

For the treatment of bacterial infections caused by susceptible microorganisms.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

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

Adverse Effects
Medicalerrors
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcenocoumarolThe risk or severity of bleeding can be increased when Teicoplanin is combined with Acenocoumarol.
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Teicoplanin.
DicoumarolThe risk or severity of bleeding can be increased when Teicoplanin is combined with Dicoumarol.
EstetrolThe therapeutic efficacy of Estetrol can be decreased when used in combination with Teicoplanin.
FluindioneThe risk or severity of bleeding can be increased when Teicoplanin is combined with Fluindione.
LactuloseThe therapeutic efficacy of Lactulose can be decreased when used in combination with Teicoplanin.
PhenindioneThe risk or severity of bleeding can be increased when Teicoplanin is combined with Phenindione.
PhenprocoumonThe risk or severity of bleeding can be increased when Teicoplanin is combined with Phenprocoumon.
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Teicoplanin.
Typhoid vaccineThe therapeutic efficacy of Typhoid vaccine can be decreased when used in combination with Teicoplanin.
Interactions
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Food Interactions
Not Available

Products

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International/Other Brands
Targocid (Sanofi-Aventis)

Categories

ATC Codes
J01XA02 — Teicoplanin
Drug Categories
Classification
Not classified
Affected organisms
  • Gram-positive Bacteria

Chemical Identifiers

UNII
4U3D3YY81M
CAS number
61036-62-2

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. [Article]
  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. [Article]
  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. [Article]
  4. Pryka RD, Rodvold KA, Rotschafer JC: Teicoplanin: an investigational glycopeptide antibiotic. Clin Pharm. 1988 Sep;7(9):647-58. [Article]
  5. Shea KW, Cunha BA: Teicoplanin. Med Clin North Am. 1995 Jul;79(4):833-44. doi: 10.1016/s0025-7125(16)30042-6. [Article]
  6. Greenwood D: Microbiological properties of teicoplanin. J Antimicrob Chemother. 1988 Jan;21 Suppl A:1-13. doi: 10.1093/jac/21.suppl_a.1. [Article]
KEGG Drug
D02142
KEGG Compound
C15820
PubChem Substance
46507509
RxNav
57021
ChEBI
29687
PharmGKB
PA164746244
Wikipedia
Teicoplanin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedPreventionTotal Hip and Knee Arthroplasties1
4CompletedTreatmentAmputation, Wound / Wound Infections1
4CompletedTreatmentFebrile Neutropenia / Infection1
4Not Yet RecruitingTreatmentCholangitis, Secondary Biliary / Drug Specific Antibodies / Treatment Compliance1
4TerminatedTreatmentClostridium Difficile Infection-associated Diarrhea and Colitis1
4Unknown StatusTreatmentBacteremia / Catheter Related Infections1
4Unknown StatusTreatmentInfection caused by staphylococci1
3Not Yet RecruitingPreventionLumbar Disc Lesion / Lumbar Spondylolisthesis / Prolapsed Lumbar Disc / Scoliosis Lumbar Region / Spinal Stenosis of Lumbar Region1
3TerminatedTreatmentSkin Diseases, Infectious / Soft Tissues Infections1
2CompletedTreatmentOsteoarticular Infections1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, solutionIntramuscular; Intravenous
Injection, powder, for solutionParenteral
Injection, powder, for solutionIntramuscular; Intravenous
Injection, powder, lyophilized, for solutionParenteral200 mg
Injection, powder, for solutionOral; Parenteral
Powder, for solutionOral; Parenteral
SolutionOral
Injection, powder, lyophilized, for solutionIntramuscular; Intravenous400 mg
Injection, powder, for solutionOral
Injection, powder, for solution; powder, for solutionIntramuscular; Intravenous; Oral
InjectionIntramuscular; Intravenous
Injection, powder, for solution
Powder200 mg/1vial
Powder400 mg/1vial
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

Targets

Drugtargets
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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. [Article]
  2. Reynolds PE: Structure, biochemistry and mechanism of action of glycopeptide antibiotics. Eur J Clin Microbiol Infect Dis. 1989 Nov;8(11):943-50. [Article]
  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. [Article]
  4. Boger DL: Vancomycin, teicoplanin, and ramoplanin: synthetic and mechanistic studies. Med Res Rev. 2001 Sep;21(5):356-81. [Article]

Drug created on December 05, 2007 08:57 / Updated on June 16, 2021 12:31