teicoplanin

Also 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 Å²
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

Wikidata facts

Subclass of: chemical compound
Mass: 1877.5565819239985
Has use: medication

Show 7 more facts

Commons category: Teicoplanin
defined daily dose: 0.4
isomeric SMILES: CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]1[C@@H]2NC(=O)[C@H](NC(=O)[C@@H]3NC(=O)[C@H]4NC(=O)[C@@H](Cc5ccc(Oc6cc3cc(Oc3ccc1cc3Cl)c6O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1NC([*])=O)c(Cl)c5)NC(=O)[C@H](N)c1ccc(O)c(Oc3cc(O)cc4c3)c1)c1ccc(O)c(c1)-c1c(O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O)cc(O)cc1[C@H](NC2=O)C(O)=O
chemical formula: C₈₈H₉₇Cl₂N₉O₃₃
subject has role: antibiotic
has characteristic: biopharmaceutical
canonical SMILES: CCCCCCCCCC(=O)NC1C(Oc2c3cc4cc2Oc2ccc(cc2Cl)C(OC2OC(CO)C(O)C(O)C2NC(C)=O)C2NC(=O)C(NC(=O)C4NC(=O)C4NC(=O)C(Cc5ccc(c(Cl)c5)O3)NC(=O)C(N)c3ccc(O)c(c3)Oc3cc(O)cc4c3)c3ccc(O)c(c3)-c3c(OC4OC(CO)C(O)C(O)C4O)cc(O)cc3C(C(=O)O)NC2=O)OC(CO)C(O)C1O

Sources (4)

via Wikidata · CC0

~13 min read

Encyclopedic overview

14 sections

Contents

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 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.