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Vancomycin

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CAT#
10-101-103
Synonyms/Alias
Vancocin; Vancomycine; Vancomycinum; Vancomicina; HSDB 3262; Vancomycin; EINECS 215-772-6; LS-161387; LS161387; Diatracin; Vancocine
CAS No.
1404-90-6
M.W/Mr.
1449.25
Molecular Formula
C66H75Cl2N9O24
Source
Synthetic
Long-term Storage Conditions
−20°C
Application
Vancomycin is an antibiotic used to treat a number of bacterial infections. It is a member of the glycopeptide antibiotic class and is effective mostly against Gram-positive bacteria.
Description
Vancomycin is an antibacterial compound obtained from Streptomyces orientalis. It is a glycopeptide related to ristocetin that inhibits bacterial cell wall assembly.
Areas of Interest
Antibiotics
  • Background
  • Related Products
  • References

Vancomycin is a branched tricyclic glycosylated peptide with bactericidal activity against most organisms and bacteriostatic effect on enterococci. At a site different from that of penicillins and cephalosporins, vancomycin binds tightly to the D-alanyl-D-alanine portion of cell wall precursors, thereby interfering with bacterial cell wall synthesis. This leads to activation of bacterial autolysins that destroy the cell wall by lysis. Vancomycin may also alter the permeability of bacterial cytoplasmic membranes and may selectively inhibit RNA synthesis.

CAS: 171500-79-1
Sequence: ---
M.W: 1816.69
Molecular Formula: C88H100Cl2N10O28
CAS: 76168-82-6
Sequence: ---
M.W: 2254.06
Molecular Formula: C106H170ClN21O30
CAS: 61036-62-2
Sequence: ---
M.W: 1879.66
Molecular Formula: C88H95Cl2N9O33

Vancomycin (VCM) is a tricyclic glycopeptide antibiotic produced by Streptococcus orientalis. Widely used in hospitals, it is indicated to fight severe infections caused by Gram-positive bacteria, especially with the advent of MRSA (methicillin-resistant Staphylococcus aureus), penicillin-resistant pneumococci among others. Furthermore, it is indicated for the treatment of patients allergic to penicillins and cephalosporins. Dose recommendations, dilution rates and types of infusion are controversial and also result in toxic effects. Aim of this paper was to perform a literature review showing the therapeutic and adverse effects of vancomycin.

Bruniera, F. R., Ferreira, F. M., Saviolli, L. R., Bacci, M. R., Feder, D., da Luz Goncalves Pedreira, M., ... & Fonseca, F. L. A. (2015). The use of vancomycin with its therapeutic and adverse effects: a review. Eur Rev Med Pharmacol Sci, 19(4), 694-700.

Vancomycin became available for clinical use >50 years ago but was soon discarded in favor of other antibiotics that were deemed to be more efficacious and less toxic. The advent of pseudomembranous enterocolitis, coupled with the spread of methicillin-resistant Staphylococcus aureus, led to a resurgence in the use of vancomycin. Almost immediately, concerns arose with regard to its therapeutic utility. In addition, resistance to vancomycin developed, first in enterococci and later in staphylococci. Several types of resistance have now been identified, each with a unique effect on infections treated with vancomycin. Recent studies have rekindled interest in the best way to administer the antibiotic. The findings of future studies may result in a return to measuring levels of vancomycin in serum, to assure a successful therapeutic outcome.

Levine, D. P. (2006). Vancomycin: a history. Clinical Infectious Diseases, 42(Supplement_1), S5-S12.

Vancomycin is one of only a few antibiotics available to treat patients infected with methicillin-resistant Staphylococcus aureus and methicillin-resistant, coagulase-negative Staphylococcus species. Therefore, understanding the clinical implications of the pharmacokinetic and pharmacodynamic properties of vancomycin is a necessity for clinicians. Vancomycin is a concentration-independent antibiotic (also referred to as a "time-dependent" antibiotic), and there are factors that affect its clinical activity, including variable tissue distribution, inoculum size, and emerging resistance. This article reviews the pharmacokinetic and pharmacodynamic data related to vancomycin and discusses such clinical issues as toxicities and serum concentration monitoring.

Rybak, M. J. (2006). The pharmacokinetic and pharmacodynamic properties of vancomycin. Clinical Infectious Diseases, 42(Supplement_1), S35-S39.

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