HomeSearch by AntimicrobialVancomycin (Vancocyn, Lyphocin)
Antimicrobial Name: Vancomycin (Vancocyn, Lyphocin)
CAS Number: 1404-90-6
Type of Antibiotic: Glycopeptides
Origin: Fermentation
Functional Category: Antibiotic
Molecular Weight: 1449.3
Mechanism of Action: The bactericidal action of vancomycin results primarily from inhibition of cell-wall biosynthesis. Specifically, vancomycin prevents incorporation of N-acetylmuramic acid (NAM)- and N-acetylglucosamine (NAG)-peptide subunits from being incorporated into the peptidoglycan matrix; which forms the major structural component of Gram-positive cell walls. The large hydrophilic molecule is able to form hydrogen bond interactions with the terminal D-alanyl-D-alanine moieties of the NAM/NAG-peptides. Normally this is a five-point interaction. This binding of vancomycin to the D-Ala-D-Ala prevents the incorporation of the NAM/NAG-peptide subunits into the peptidoglycan matrix. In addition, vancomycin alters bacterial-cell-membrane permeability and RNA synthesis. There is no cross-resistance between vancomycin and other antibiotics. Vancomycin is not active in vitro against gram-negative bacilli, mycobacteria, or fungi.
Chemical Formula:

C66H75Cl2N9O24

Solubility:

50 mg/ml in H2O

Resistance Genes:

vanA: vancomycin resistance protein VanA

vanB: vancomycin resistance protein VanB

vanH: vancomycin resistance protein VanH

vanW: vancomycin resistance protein VanW

vanX: vancomycin resistance protein VanX

vanY: vancomycin resistance protein VanY

vanZ: vancomycin resistance protein VanZ

vanc: VanC type vancomycin resistance operon genes, which can synthesize peptidoglycan with modified C-terminal D-Ala-D-Ala to D-alanine--D-serine.

vand: VanD type vancomycin resistance operon genes, which can synthesize peptidoglycan with modified C-terminal D-Ala-D-Ala to D-alanine--D-lactate.

vane: VanE type vancomycin resistance operon genes, which can synthesize peptidoglycan with modified C-terminal D-Ala-D-Ala to D-alanine--D-serine.

vang: VanG type vancomycin resistance operon genes, which can synthesize peptidoglycan with modified C-terminal D-Ala-D-Ala to D-alanine--D-serine.

vanha: VanA type vancomycin resistance operon genes, which can synthesize peptidoglycan with modified C-terminal D-Ala-D-Ala to D-alanine--D-lactate.

vanhb: VanB type vancomycin resistance operon genes, which can synthesize peptidoglycan with modified C-terminal D-Ala-D-Ala to D-alanine--D-lactate.

vanhd: VanD type vancomycin resistance operon genes, which can synthesize peptidoglycan with modified C-terminal D-Ala-D-Ala to D-alanine--D-lactate.

vanra: VanA type vancomycin resistance operon genes, which can synthesize peptidoglycan with modified C-terminal D-Ala-D-Ala to D-alanine--D-lactate.

vanrb: VanB type vancomycin resistance operon genes, which can synthesize peptidoglycan with modified C-terminal D-Ala-D-Ala to D-alanine--D-lactate.

vanrc: VanC type vancomycin resistance operon genes, which can synthesize peptidoglycan with modified C-terminal D-Ala-D-Ala to D-alanine--D-serine.

vanrd: VanD type vancomycin resistance operon genes, which can synthesize peptidoglycan with modified C-terminal D-Ala-D-Ala to D-alanine--D-lactate.

vanre: VanE type vancomycin resistance operon genes, which can synthesize peptidoglycan with modified C-terminal D-Ala-D-Ala to D-alanine--D-serine.

vanrg: VanG type vancomycin resistance operon genes, which can synthesize peptidoglycan with modified C-terminal D-Ala-D-Ala to D-alanine--D-serine.

vansa: VanA type vancomycin resistance operon genes, which can synthesize peptidoglycan with modified C-terminal D-Ala-D-Ala to D-alanine--D-lactate.

vansb: VanB type vancomycin resistance operon genes, which can synthesize peptidoglycan with modified C-terminal D-Ala-D-Ala to D-alanine--D-lactate.

vansc: VanC type vancomycin resistance operon genes, which can synthesize peptidoglycan with modified C-terminal D-Ala-D-Ala to D-alanine--D-serine.

vansd: VanD type vancomycin resistance operon genes, which can synthesize peptidoglycan with modified C-terminal D-Ala-D-Ala to D-alanine--D-lactate.

vanse: VanE type vancomycin resistance operon genes, which can synthesize peptidoglycan with modified C-terminal D-Ala-D-Ala to D-alanine--D-serine.

vansg: VanG type vancomycin resistance operon genes, which can synthesize peptidoglycan with modified C-terminal D-Ala-D-Ala to D-alanine--D-serine.

vant: VanC type vancomycin resistance operon genes, which can synthesize peptidoglycan with modified C-terminal D-Ala-D-Ala to D-alanine--D-serine.

vante: VanE type vancomycin resistance operon genes, which can synthesize peptidoglycan with modified C-terminal D-Ala-D-Ala to D-alanine--D-serine.

vantg: VanG type vancomycin resistance operon genes, which can synthesize peptidoglycan with modified C-terminal D-Ala-D-Ala to D-alanine--D-serine.

vanug: VanG type vancomycin resistance operon genes, which can synthesize peptidoglycan with modified C-terminal D-Ala-D-Ala to D-alanine--D-serine.

vanwb: VanB typ

Comments:

Vancomycin (Vancocyn, Lyphocin) is a glycopeptide antibiotic used in the prophylaxis and treatment of infections caused by Gram-positive bacteria. It has traditionally been reserved as a drug of "last resort", used only after treatment with other antibiotics had failed, although the emergence of vancomycin-resistant organisms means that it is increasingly being displaced from this role by linezolid (Zyvox) available PO and IV and daptomycin (Cubicin) IV and quinupristin/dalfopristin (Synercid) IV.