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Repositioning Candidate Details

Candidate ID: R0145
Source ID: DB00512
Source Type: approved
Compound Type: small molecule
Compound Name: Vancomycin
Synonyms:
Molecular Formula: C66H75Cl2N9O24
SMILES: CN[C@H](CC(C)C)C(=O)N[C@@H]1[C@H](O)C2=CC=C(OC3=C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O[C@H]4C[C@](C)(N)[C@H](O)[C@H](C)O4)C4=CC(=C3)[C@@H](NC(=O)[C@H](CC(N)=O)NC1=O)C(=O)N[C@@H]1C3=CC(=C(O)C=C3)C3=C(O)C=C(O)C=C3[C@H](NC(=O)[C@@H](NC1=O)[C@H](O)C1=CC(Cl)=C(O4)C=C1)C(O)=O)C(Cl)=C2
Structure:
DrugBank Description: Antibacterial obtained from Streptomyces orientalis. It is a glycopeptide related to ristocetin that inhibits bacterial cell wall assembly and is toxic to kidneys and the inner ear. As of January 29 2018, CutisPharma's Firvanq is the only FDA approved vancomycin oral liquid treatment option available for the the treatment of _Clostridium difficile_ associated diarrhea and enterocolitis caused by _Staphylococcus aureus_, including methicillin-resistant strains [LP1196]. Such an oral liquid formulation is expected to make _Clostridium difficile_ associated diarrhea therapy more accessible in comparison to previously available specialty compounding products [LP1196].
CAS Number: 1404-90-6
Molecular Weight: 1449.254
DrugBank 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].
DrugBank Pharmacology: 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: <i>Listeria monocytogenes</i>, <i>Streptococcus pyogenes</i>, <i>Streptococcus pneumoniae</i> (including penicillin-resistant strains), <i>Streptococcus agalactiae</i>, <i>Actinomyces</i> species, and <i>Lactobacillus</i> 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].
DrugBank 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]
Targets: D-Ala-D-Ala moiety of NAM/NAG peptide subunits of peptidoglycan
Inclusion Criteria: