Vancomycin

• CAS Number: 1404-90-6

Vancomycin is an antibiotic in the class of compounds known glycopeptide antibiotics. Vancomycin was obtained in the 1950s from cultures of Amycolatopsis orientalis, but only used around 1980 as an effective alternative against multidrug-resistant staphylococci. Staphylococci in addition to enterococci frequently in hospitals as a cause of nosocomial infections. It is an antibiotic in the third line, if no other means are effective due to resistance. It is not absorbed from the intestine, an effect that you can exploit in antibiotic- associated colitis.

Mechanism of action

Vancomycin inhibits the development of the bacterial cell wall, by forming with the terminal L-lysine -D -alanyl- D-alanine groups of the bacterial cell wall murein ingredient a complex. Thus it blocks the blocks of the cross-linking of the cell wall of gram-positive bacteria by a bridge of five glycine residues ( Pentaglycinbrücke / pentapeptide side chain), such that certain of the cross-linking significant blocks ( N-acetylglucosamine, N- acetylmuramic acid ) can not be incorporated into the growing bacterial cell wall. The mechanism of action of vancomycin as glycopeptide is not based on the binding to the transglycosylase. Since bacteria have a relatively high osmotic pressure, the cell wall can be used without the cross-linking this can not withstand pressure, and the bacterium bursts.

Application as a reserve antibiotic

The use of vancomycin is in the form of intravenous infusions or injections for the treatment of severe infections caused by gram- positive pathogens that are resistant to other antibiotics (eg, oxacillin - resistant Staphylococcus aureus). Vancomycin has long been regarded as the last hope for the treatment of life-threatening infections by Gram-positive spherical bacteria ( cocci ) as so-called reserve antibiotic. That hope ended in 1987, when vancomycin-resistant enterococci (VRE ) published in the hospitals. Vancomycin - resistance is due to the expression of an alternative D -alanyl part: due D-alanine ligase. This alternative ligated enzyme D-lactate instead of D -alanine, resulting in a (-OH) - can be used instead of ( NH2 ) terminus. Thus, the binding of vancomycin is prevented and the cross-linking of the murein of a Depsipeptidbindung. A different type of resistance is the expression of a D-Ala: D-Ser - D-Ala ligase in place of the D- Ala ligase.

For some years now considered as a reserve antibiotic linezolid (Last line of defense ).

Further use

Vancomycin works very well in antibiotic- associated pseudomembranous enterocolitis caused by Clostridium difficile. The non-absorbable antibiotic in the intestine is administered orally for this purpose. Primarily, however, the much cheaper Metronidazole is used in pseudomembranous enterocolitis, with which it is also less problems with the development of resistance ( vancomycin-resistant enterococci, VRE ).

Feeding practices

The growth promoter avoparcin, which has structural similarity with vancomycin, was used until 1996 in Germany. He is regarded as a trigger for the spread of vancomycin - resistant enterococci.

Since 1997, avoparcin may no longer be used as a feed additive in the EU.

Finished medicinal product

Vancomycin was developed by Eli Lilly and introduced in the 1950s in the market, first in the United States. Is used medicinally only the water-soluble vancomycin hydrochloride, either as a powder for solution for infusion ( for systemic therapy ) and as a powder for oral solution or capsule ( for topical therapy).

Vancomycinhaltige drugs are both under the brand name Vancocin as well as under the generic name ( generic name ) on the market (eg vancomycin CP Lilly).