Teicoplanin

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Cat Number

API61036622

CAS Number

61036-62-2

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CAS Number

61036-62-2

Storage

2-8℃

Synonyms

Teichomycin

Molecular Formula

C88H97Cl2N9O33

Molecular Weight

1879.7

Appearance

White powder

Melting Point

310 ℃

Relative Density

1.69

Standard

EP/IP

General Description

Teicoplanin is an antibiotic drug of the lipoglycopeptide class. It is produced by the actinobacterium Actinoplanes teichomyceticus. There are five major components with different fatty acid moiety. It is a second-generation glycopeptide antibiotic and has more lipophilicity, a longer half-life, and better tissue distribution with milder adverse reactions than vancomycin.

Mechanism of Action

Inhibition of bacterial cell wall synthesis is the mainstay of the mechanism of action of Teicoplanin. It binds to the acyl-D-alanyl-D-alanine terminus of peptidoglycan precursors and inhibits the addition of newly synthesized units to the peptidoglycan polymer. It is bactericidal against gram-positive aerobic and anaerobic bacteria, including Staphylococcus aureus (including MRSA), Streptococcus pyogenes, Streptococcus pneumoniae, and Clostridium difficile.

Application

Teicoplanin is used for infections with gram-positive bacteria that are resistant to penicillin and cephalosporins, such as endocarditis, osteomyelitis, septicemia, respiratory, urinary and skin infections. It is one of the first choices of drugs for infections due to multi-drug resistance to Staphylococcus aureus and Enterococcus. It has a long half-life, high protein binding, and is primarily eliminated renally. It is a time-dependent antibiotic with a significant post-antibiotic effect.

Teicoplanin has been administered as a treatment for several severe infections including endocarditis, pneumonia, and sepsis. As a result of its favorable pharmacokinetics (long half-life of 30 h) and low toxicity profile, it can be used in immunocompromised hosts and children. The antibiotic is active in multiple tissues, including high efficacy in the lungs for respiratory infections, with large concentrations in the epithelial lining fluid of the lung.
Recent data have demonstrated the in vitro antiviral activity of Teicoplanin against RNA viruses, including SARS-CoV-2. Teicoplanin was shown to inhibit SARS-CoV-2 with an EC50 of 15.7 µM. Two proposed mechanisms of antiviral activity against SARS-CoV-2 have been described: (1) Inhibition of cathepsin L, which would lead to viral retention in endosomes and (2) Inhibition of SARS-CoV-2 main cysteine protease (3CLpro), required for viral replication.
Bacterial co-infections are common in COVID-19 patients and lead to poor outcomes. Due to the efficacy of Teicoplanin against Gram-positive bacteria, it could be used to treat bacterial co-infections as well as the virus itself in patients with COVID-19. In clinical trials, viral clearance occurred in 40% of COVID-19 patients receiving Teicoplanin.

Fig. 1 Mechanism of action of Teicoplanin anti-SARS-CoV activity. (Vimberg V.; et al. 2021)

References

Vimberg V, et al. Teicoplanin—a new use for an old drug in the COVID-19 era? Pharmaceuticals, 2021, 14(12): 1227.

Kai K C et al. created an injectable drug delivery system for treating an inflammatory bone disease called osteomyelitis, which is usually of bacterial origin. A poloxamer 407 hydrogel loaded with Teicoplanin and β-tricalcium phosphate (β-TCP) doped with Mg and Zn was formulated to control infection and also provide the environment to the bone to regenerate. Team showed that Teicoplanin was loaded into the poloxamer micelles and was encapsulated into the Corona, resulting in an increase in the hydrodynamic radius and a change in the surface charge of the micelles. Release of the drug was found to be sustained from the micelles, which was further confirmed through in vitro studies. The antibacterial activity of formulations containing Teicoplanin was found to be effective against Gram-positive bacteria. This was comparable to standard antibiotics used in the treatment of osteomyelitis.

Fig. 2 Teicoplanin-based injectable hydrogel for osteomyelitis treatment. (Kai K C.; et al. 2024)

References

Kai K C, et al. Tricalcium phosphate-loaded injectable hydrogel as a promising osteogenic and bactericidal teicoplanin-delivery system for osteomyelitis treatment: An in vitro and in vivo investigation. Biomaterials Advances, 2024, 164: 213966.