General
Preferred name
VANCOMYCIN
Synonyms
Vancomycin hydrochloride from Streptomyces orientalis ()
Vancomycin HCL ()
VANCOMYCIN HYDROCHLORIDE ()
Vancomycin (hydrochloride) ()
Firvanq kit ()
Vancoled ()
Vancomycin (as hydrochloride) ()
Vancomycin monohydrochloride ()
Vanoled ()
NSC-757377 ()
Vancocin hydrochloride ()
Vancocin Matrigel ()
Vancor ()
Vancomycin, monohydrochloride ()
Firvanq ()
Vancocin ()
P&D ID
PD009986
CAS
1404-93-9
1404-90-6
Tags
natural product
drug
available
Approved by
FDA
First approval
1964
Drug Status
approved
Max Phase
Phase 4
Drug indication
Antibacterial
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
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
Amphoteric glycopeptide antibiotic; interefers with cell wall syntehsis by bind to peptidoglycan
(LOPAC library)
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Cell lines
0
Organisms
6
Compound Sets
17
AdooQ Bioactive Compound Library
Cayman Chemical Bioactives
ChEMBL Approved Drugs
ChEMBL Drugs
Drug Repurposing Hub
DrugBank
DrugBank Approved Drugs
DrugCentral
DrugCentral Approved Drugs
Guide to Pharmacology
LOPAC library
LSP-MoA library (Laboratory of Systems Pharmacology)
NCATS Inxight Approved Drugs
ReFrame library
Selleckchem Bioactive Compound Library
TargetMol Bioactive Compound Library
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
49
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
Custom attributes
(extracted from source data)
Selectivity
Cell wall synthesis
Pathway
Immunology/Inflammation
Anti-infection
Autophagy
Target
Cell wall
antibiotic
Bacterial
Antibiotics,Antibiotics for Plant Cell Culture,Bacterial
Indication
endocarditis
MOA
bacterial cell wall synthesis inhibitor
Source data