General
Preferred name
VANCOMYCIN
Synonyms
Vancomycin hydrochloride from Streptomyces orientalis ()
Vancomycin HCL ()
Vancomycin (hydrochloride) ()
VANCOMYCIN HYDROCHLORIDE ()
Vancomycin monohydrochloride ()
Vanoled ()
NSC-757377 ()
Vancomycin (as hydrochloride) ()
Vancocin Matrigel ()
Firvanq ()
Vancomycin, monohydrochloride ()
Firvanq kit ()
Vancocin hydrochloride ()
Vancor ()
Vancoled ()
Vancocin ()
Vancomycine ()
Vancomicina ()
P&D ID
PD009986
CAS
1404-90-6
1404-93-9
Tags
available
drug
natural product
Approved by
FDA
First approval
1964
Drug Status
approved
Max Phase
4.0
Drug indication
cellulitis
infection
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
DESCRIPTION Vancomycin hydrochloride is an antibiotic for the treatment of bacterial infections. It acts by inhibiting the second stage of cell wall synthesis of susceptible bacteria. Vancomycin also alters the permeability of the cell membrane and selectively inhibits ribonucleic acid synthesis.
PHARMACODYNAMICS Vancomycin is a branched tricyclic glycosylated nonribosomal peptide often reserved as the "drug of last resort", used only after treatment with other antibiotics has failed. Vancomycin has been shown to be active against most strains of the following microorganisms, both in vitro and in clinical infections: Listeria monocytogenes, Streptococcus pyogenes, Streptococcus pneumoniae (including penicillin-resistant strains), Streptococcus agalactiae, Actinomyces species, and Lactobacillus species. The combination of vancomycin and an aminoglycoside acts synergistically in vitro against many strains of Staphylococcus aureus, Streptococcus bovis, enterococci, and the viridans group streptococci [FDA Label].
INDICATION A variety of dosage forms (for example, oral, injections, etc.) exist for the treatment of serious or severe infections caused by susceptible strains of methicillin-resistant (beta-lactam-resistant) staphylococci [FDA Label].; ; Additionally, a unique FDA approved oral liquid treatment is also available and indicated for the treatment of Clostridium difficile associated diarrhea and enterocolitis caused by _Staphylococcus aureus_, including methicillin-resistant strains [L1196].
DESCRIPTION Vancomycin is a complex glycopeptide antibacterial that was originally isolated from Streptomyces orientalis. It has bactericidal activity against most organisms and is bacteriostatic vs. enterococci. Semisynthetic derivatives such as , and are now available for clinical use. (GtoPdb)
MOA 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. Vancomycin forms hydrogen bonds with the terminal D-alanyl-D-alanine moieties of the NAM/NAG-peptides, preventing 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. [FDA Label]
DESCRIPTION Vancomycin is an antibiotic for the treatment of bacterial infections.
DESCRIPTION Amphoteric glycopeptide antibiotic; interefers with cell wall syntehsis by bind to peptidoglycan (LOPAC library)
DESCRIPTION Vancomycin hydrochloride (Vancomycin HCl) is the hydrochloride salt of vancomycin, a branched tricyclic glycosylated peptide with bactericidal activity against most organisms and bacteriostatic effect on enterococci. (TargetMol Bioactive Compound Library)
DESCRIPTION Vancomycin is a glycopeptide antibiotic that exerts its antimicrobial activity by altering the permeability of cell membranes and selectively inhibiting ribonucleic acid synthesis. Vancomycin can be used for the treatment of serious infections for which all antibiotics have failed. (TargetMol Bioactive Compound Library)
Cell lines
0
Organisms
6
Compound Sets
18
AdooQ Bioactive Compound Library
A12696
Cayman Chemical Bioactives
15327
ChEMBL Approved Drugs
CHEMBL1200628
CHEMBL262777
ChEMBL Drugs
CHEMBL1200628
CHEMBL262777
CZ-OPENSCREEN Bioactive Library
Drug Repurposing Hub
DrugBank
DB00512
DrugBank Approved Drugs
DB00512
DrugCentral
2807
DrugCentral Approved Drugs
2807
Guide to Pharmacology
10932
LOPAC library
LSP-MoA library (Laboratory of Systems Pharmacology)
CHEMBL262777
MedChem Express Bioactive Compound Library
HY-17362
HY-B0671
NCATS Inxight Approved Drugs
6Q205EH1VU
ReFrame library
Selleckchem Bioactive Compound Library
vancomycin-hydrochloride-vancocin
vancomycin
TargetMol Bioactive Compound Library
T0832
T8641
External IDs
57
Properties
(calculated by RDKit )
Molecular Weight
1447.43
Hydrogen Bond Acceptors
25
Hydrogen Bond Donors
19
Rotatable Bonds
13
Ring Count
12
Aromatic Ring Count
5
cLogP
0.11
TPSA
530.49
Fraction CSP3
0.42
Chiral centers
18.0
Largest ring
16.0
QED
0.07
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Selectivity
Cell wall synthesis
Pathway
Autophagy
Microbiology/virology
Immunology/Inflammation
Anti-infection
Indication
endocarditis
MOA
bacterial cell wall synthesis inhibitor
Target
antibiotic
Bacterial
Antibiotics,Antibiotics for Plant Cell Culture,Bacterial
Cell wall
Source data