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
Structure
Weight
Average: 1879.67
Monoisotopic: 1877.556582
Chemical Formula
C88H97Cl2N9O33
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.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Induction ofAngina pectoris••••••••••••••••••• ••••••• •••••••• •••••••
Prevention ofAnginal pain••••••••••••••••••• ••••••• •••••••• •••••••
Treatment ofBacteremia•••••••••••••••••••••• ••••••• ••• ••••••••
Treatment ofBloodstream infections•••••••••••••••••••••• ••••••• ••• ••••••••• •••••••••• ••••••••• ••••••••
Treatment ofBone and joint infections•••••••••••••••••••••• ••••••• ••• ••••••••
Contraindications & Blackbox Warnings
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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
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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.
AmbroxolThe risk or severity of methemoglobinemia can be increased when Teicoplanin is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Teicoplanin is combined with Articaine.
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Teicoplanin.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Teicoplanin is combined with Benzocaine.
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
InChI Key
BJNLLBUOHPVGFT-CAYRISATSA-N
InChI
InChI=1S/C88H97Cl2N9O33/c1-3-4-5-6-7-8-9-10-60(108)94-68-74(113)71(110)58(32-101)129-87(68)132-78-55-26-40-27-56(78)126-52-18-14-38(24-47(52)90)77(131-86-67(92-34(2)103)73(112)70(109)57(31-100)128-86)69-84(121)98-66(85(122)123)45-29-42(105)30-54(127-88-76(115)75(114)72(111)59(33-102)130-88)61(45)44-23-37(13-15-49(44)106)63(81(118)99-69)96-83(120)65(40)97-82(119)64-39-21-41(104)28-43(22-39)124-53-25-36(12-16-50(53)107)62(91)80(117)93-48(79(116)95-64)20-35-11-17-51(125-55)46(89)19-35/h11-19,21-30,48,57-59,62-77,86-88,100-102,104-107,109-115H,3-10,20,31-33,91H2,1-2H3,(H,92,103)(H,93,117)(H,94,108)(H,95,116)(H,96,120)(H,97,119)(H,98,121)(H,99,118)(H,122,123)/t48-,57-,58-,59-,62-,63-,64+,65-,66+,67-,68-,69+,70-,71-,72-,73-,74-,75+,76+,77-,86+,87+,88?/m1/s1
IUPAC Name
(1S,2R,19R,22R,34S,37R,40R,52S)-22-amino-5,63-dichloro-64-{[(2S,3R,4R,5S,6R)-3-decanamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-{[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-26,31,44,49-tetrahydroxy-21,35,38,54,56,59-hexaoxo-47-{[(3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7,13,28-trioxa-20,36,39,53,55,58-hexaazaundecacyclo[38.14.2.2^{3,6}.2^{14,17}.2^{19,34}.1^{8,12}.1^{23,27}.1^{29,33}.1^{41,45}.0^{10,37}.0^{46,51}]hexahexaconta-3,5,8(64),9,11,14,16,23,25,27(61),29,31,33(60),41,43,45(57),46(51),47,49,62,65-henicosaene-52-carboxylic acid
SMILES
CCCCCCCCCC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2OC3=C(Cl)C=C(C=C3)[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3NC(C)=O)[C@@H]3NC(=O)[C@H](NC(=O)[C@@H]4NC(=O)[C@H]5NC(=O)[C@@H](CC6=CC=C(OC1=CC4=C2)C(Cl)=C6)NC(=O)[C@H](N)C1=CC=C(O)C(OC2=CC(O)=CC5=C2)=C1)C1=CC=C(O)C(=C1)C1=C(C=C(O)C=C1OC1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O)[C@H](NC3=O)C(O)=O

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
ChemSpider
78430443
BindingDB
512667
RxNav
57021
ChEBI
29687
PharmGKB
PA164746244
Wikipedia
Teicoplanin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedPreventionTotal Knee and Total Hip Arthroplasty1
4CompletedTreatmentAmputation, Wound / Wound Infections1
4CompletedTreatmentAnti-drug antibody development / Cholangitis, Secondary Biliary / Compliance, Treatment1
4CompletedTreatmentFebrile Neutropenia / Infection1
4RecruitingTreatmentBacterial Infections1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, solutionIntramuscular; Intravenous
SolutionParenteral200.000 mg
Injection, solutionIntramuscular; Intravenous200 mg
Injection, solutionIntramuscular; Intravenous400 mg
SolutionParenteral400.00 mg
Injection, powder, for solutionIntramuscular; Intravenous400 mg
Injection, powder, for solutionParenteral
Injection, solutionIntramuscular; Intravenous200 mg/3ml
Injection, powder, for solutionIntramuscular; Intravenous200 mg
Injection, solutionIntramuscular; Intravenous400 mg/3ml
Injection, powder, for solutionIntramuscular; Intravenous
Injection, powder, lyophilized, for solutionParenteral200 mg
Injection, powder, for solutionOral; Parenteral
Injection, powder, for solutionParenteral200 mg
Injection, powder, for solutionParenteral400 mg
Powder, for solutionOral; Parenteral200 mg
Powder, for solutionOral; Parenteral400 mg
Powder, for solutionOral; Parenteral
SolutionOral
Injection, powder, lyophilized, for solutionIntramuscular; Intravenous400 mg
Injection, powder, for solution200 MG
Injection, powder, for solution400 MG
Injection, powder, for solutionOral
Injection, powder, for solution; powder, for solutionIntramuscular; Intravenous; Oral100 MG
Injection, powder, for solution; powder, for solutionIntramuscular; Intravenous; Oral200 MG
Injection, powder, for solution; powder, for solutionIntramuscular; Intravenous; Oral400 MG
Injection, powder, for solutionOral; Parenteral100 MG
Injection, powder, for solutionOral200 MG
Injection, powder, for solutionOral400 MG
Injection, powder, for solutionOral; Parenteral200 MG
Injection, powder, for solutionOral; Parenteral400 MG
InjectionIntramuscular; Intravenous200 mg
InjectionIntramuscular; Intravenous400 mg
SolutionIntravenous200.000 mg
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
PropertyValueSource
logP-2.3Chemaxon
pKa (Strongest Acidic)3.04Chemaxon
pKa (Strongest Basic)7.09Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count31Chemaxon
Hydrogen Donor Count24Chemaxon
Polar Surface Area662.41 Å2Chemaxon
Rotatable Bond Count20Chemaxon
Refractivity450.91 m3·mol-1Chemaxon
Polarizability181.38 Å3Chemaxon
Number of Rings14Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0401-0211001090-76df07ecb812b95c64b3
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-05e9-0200000490-66cbcf457185ae18a444
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0bw9-2402002690-5d49d9a15dae24c9ef23
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-059t-2000004970-2523a42c64ada1d0dad7
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-08nc-4101022960-a6977563573dcd264d1e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a6r-3520000940-4075dc13794144144a0e
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Targets

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insights and accelerate drug research.
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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 at December 05, 2007 08:57 / Updated at September 05, 2022 12:50