Structure via PubChem · Public domain (PubChem)
teicoplanin
Sign in to saveAlso known as MDL-507, TEIC, Teichomycin a2 factor 2, Teichomycin, Targocid
Teicoplanin is a glycopeptide antibiotic with a spectrum of activity similar to vancomycin. Its mechanism of action is to inhibit bacterial cell wall peptidoglycan synthesis. It is used in the prophylaxis and treatment of serious infections caused by Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus and Enterococcus faecalis.
Chemical data
- Formula
- C88H97Cl2N9O33
- Molecular weight
- 1879.7 g/mol
- IUPAC name
- (1S,2R,19R,22R,34S,37R,40R,52S)-22-amino-5,15-dichloro-64-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-3-(1-hydroxydecylideneamino)-6-(hydroxymethyl)oxan-2-yl]oxy-2-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-3-(1-hydroxyethylideneamino)-6-(hydroxymethyl)oxan-2-yl]oxy-21,26,31,35,38,44,49,54,56,59-decahydroxy-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-hexazaundecacyclo[38.14.2.23,6.214,17.219,34.18,12.123,27.129,33.141,45.010,37.046,51]hexahexaconta-3,5,8,10,12(64),14,16,20,23(61),24,26,29(60),30,32,35,38,41(57),42,44,46(51),47,49,53,55,58,62,65-heptacosaene-52-carboxylic acid
- SMILES
- CCCCCCCCCC(=N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1OC2=C3C=C4C=C2OC5=C(C=C(C=C5)[C@H]([C@H]6C(=N[C@@H](C7=C(C(=CC(=C7)O)OC8[C@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)C9=C(C=CC(=C9)[C@H](C(=N6)O)N=C([C@@H]4N=C([C@@H]1C2=CC(=CC(=C2)OC2=C(C=CC(=C2)[C@H](C(=N[C@H](CC2=CC(=C(O3)C=C2)Cl)C(=N1)O)O)N)O)O)O)O)O)C(=O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)N=C(C)O)Cl)CO)O)O)O
- InChIKey
- BJNLLBUOHPVGFT-CAYRISATSA-N
- XLogP
- 3.2
- Polar surface area
- 690 Ų
- H-bond donors
- 24
- H-bond acceptors
- 42
- Formal charge
- 0
via PubChem
Research
5,209 papers- Teicoplanin.The Medical clinics of North America · 1995
- Teicoplanin biosynthesis: unraveling the interplay of structural, regulatory, and resistance genes.Applied microbiology and biotechnology · 2020
- Teicoplanin Chemistry and Microbiology.Journal of chemotherapy (Florence, Italy) · 2000
- Teicoplanin.Indian pediatrics · 2001
- Optimal Teicoplanin Trough Concentration With Therapeutic Drug Monitoring in Children: A Systematic Review and Meta-analysis.Therapeutic drug monitoring · 2024
via PubMed
~13 min read
Encyclopedic overview
14 sectionsContents
- History
- Indications
- Susceptible organisms
- Pharmacology
- Pharmacokinetics
- Pharmacodynamics
- Adverse effects
- Considerations
- Chemistry
- Gene cluster
- Heptapeptide backbone synthesis
- Modification after heptapeptide backbone formation
- Research
- References
Teicoplanin is a glycopeptide antibiotic with a spectrum of activity similar to vancomycin. Its mechanism of action is to inhibit bacterial cell wall peptidoglycan synthesis. It is used in the prophylaxis and treatment of serious infections caused by Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus and Enterococcus faecalis.
Teicoplanin is widely available in many European, Asian, and South American countries, however it is not currently approved by the US Food and Drug Administration and is not commercially available in the United States. Teicoplanin is marketed by Sanofi-Aventis under the trade name Targocid. Other trade names include Ticocin marketed by Cipla(India).
Excerpted from Wikipedia’s “teicoplanin” article, available under the CC BY-SA 4.0 licence.