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
Structure for Teicoplanin (DB06149)
- 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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
- Angina Pectoris
- Anginal Pain
- Bacteremia
- Bloodstream Infections (BSI)
- Bone and Joint Infections
- Clostridium Difficile
- Clostridium Difficile Infection (CDI)
- Community Acquired Pneumonia (CAP)
- Complicated Urinary Tract Infection
- Infective Endocarditis (IE)
- Lower Respiratory Tract and Lung Infections
- Non-complicated Skin and Soft Tissue Infections
- Nosocomial Pneumonia
- Peritonitis
- Skin and Soft Tissue Infections (SSTIs)
- Urinary Tract Infection
- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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.
Target Actions Organism AD-Ala-D-Ala moiety of NAM/NAG peptide subunits of peptidoglycan inhibitorGram-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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcenocoumarol The risk or severity of bleeding can be increased when Teicoplanin is combined with Acenocoumarol. Articaine The risk or severity of methemoglobinemia can be increased when Teicoplanin is combined with Articaine. BCG vaccine The therapeutic efficacy of BCG vaccine can be decreased when used in combination with Teicoplanin. Benzocaine The risk or severity of methemoglobinemia can be increased when Teicoplanin is combined with Benzocaine. Benzyl alcohol The risk or severity of methemoglobinemia can be increased when Teicoplanin is combined with Benzyl alcohol. Bupivacaine The risk or severity of methemoglobinemia can be increased when Teicoplanin is combined with Bupivacaine. Butacaine The risk or severity of methemoglobinemia can be increased when Teicoplanin is combined with Butacaine. Butamben The risk or severity of methemoglobinemia can be increased when Teicoplanin is combined with Butamben. Capsaicin The risk or severity of methemoglobinemia can be increased when Teicoplanin is combined with Capsaicin. Chloroprocaine The risk or severity of methemoglobinemia can be increased when Teicoplanin is combined with Chloroprocaine. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- 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
- 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]
- 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]
- 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]
- Pryka RD, Rodvold KA, Rotschafer JC: Teicoplanin: an investigational glycopeptide antibiotic. Clin Pharm. 1988 Sep;7(9):647-58. [Article]
- Shea KW, Cunha BA: Teicoplanin. Med Clin North Am. 1995 Jul;79(4):833-44. doi: 10.1016/s0025-7125(16)30042-6. [Article]
- 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]
- External Links
- KEGG Drug
- D02142
- KEGG Compound
- C15820
- PubChem Substance
- 46507509
- ChemSpider
- 78430443
- BindingDB
- 512667
- 57021
- ChEBI
- 29687
- PharmGKB
- PA164746244
- Wikipedia
- Teicoplanin
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Prevention Total Knee and Total Hip Arthroplasty 1 4 Completed Treatment Amputation, Wound / Wound Infections 1 4 Completed Treatment Anti-drug antibody development / Cholangitis, Secondary Biliary / Compliance, Treatment 1 4 Completed Treatment Febrile Neutropenia / Infection 1 4 Terminated Treatment Clostridium Difficile Infection-associated Diarrhea and Colitis 1 4 Unknown Status Treatment Bacteremia / Catheter Related Infections 1 4 Unknown Status Treatment Infection caused by staphylococci 1 3 Terminated Treatment Skin Diseases, Infectious / Soft Tissues Infections 1 3 Unknown Status Prevention Lumbar Disc Lesion / Lumbar Spine Disc Herniation / Scoliosis; Lumbar Region / Spinal Stenosis of Lumbar Region / Spondylolisthesis, Lumbar Region 1 2 Completed Treatment Osteoarticular Infections 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, solution Intramuscular; Intravenous Injection, solution Intramuscular; Intravenous 200 mg Injection, solution Intramuscular; Intravenous 400 mg Injection, powder, for solution Parenteral Injection, solution Intramuscular; Intravenous 200 mg/3ml Injection, powder, for solution Intramuscular; Intravenous 200 mg Injection, solution Intramuscular; Intravenous 400 mg/3ml Injection, powder, for solution Intramuscular; Intravenous Injection, powder, lyophilized, for solution Parenteral 200 mg Injection, powder, for solution Intramuscular; Intravenous 400 mg Injection, powder, for solution Oral; Parenteral Injection, powder, for solution Parenteral 200 mg Injection, powder, for solution Parenteral 400 mg Powder, for solution Oral; Parenteral 200 mg Powder, for solution Oral; Parenteral 400 mg Powder, for solution Oral; Parenteral Solution Oral Injection, powder, lyophilized, for solution Intramuscular; Intravenous 400 mg Injection, powder, for solution 200 MG Injection, powder, for solution 400 MG Injection, powder, for solution Oral Injection, powder, for solution; powder, for solution Intramuscular; Intravenous; Oral 100 MG Injection, powder, for solution; powder, for solution Intramuscular; Intravenous; Oral 200 MG Injection, powder, for solution; powder, for solution Intramuscular; Intravenous; Oral 400 MG Injection, powder, for solution Oral; Parenteral 100 MG Injection, powder, for solution Oral; Parenteral 200 MG Injection, powder, for solution Oral; Parenteral 400 MG Injection Intramuscular; Intravenous 200 mg Injection Intramuscular; Intravenous 400 mg Injection, powder, for solution Powder 200 mg/1vial Powder 400 mg/1vial - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source logP -2.3 Chemaxon pKa (Strongest Acidic) 3.04 Chemaxon pKa (Strongest Basic) 7.09 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 31 Chemaxon Hydrogen Donor Count 24 Chemaxon Polar Surface Area 662.41 Å2 Chemaxon Rotatable Bond Count 20 Chemaxon Refractivity 450.91 m3·mol-1 Chemaxon Polarizability 181.38 Å3 Chemaxon Number of Rings 14 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
1. D-Ala-D-Ala moiety of NAM/NAG peptide subunits of peptidoglycan
Yes
Inhibitor
References
- 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]
- Reynolds PE: Structure, biochemistry and mechanism of action of glycopeptide antibiotics. Eur J Clin Microbiol Infect Dis. 1989 Nov;8(11):943-50. [Article]
- 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]
- 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