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Namespace Prefixes

PrefixIRI
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n25http://www.drugs.com/
n9http://linked.opendata.cz/resource/drugbank/drug/DB00512/identifier/chemspider/
n8http://linked.opendata.cz/resource/drugbank/drug/DB00512/identifier/chebi/
n17http://bio2rdf.org/drugbank:
admshttp://www.w3.org/ns/adms#
n29http://linked.opendata.cz/resource/drugbank/drug/DB00512/identifier/wikipedia/
n20http://linked.opendata.cz/resource/drugbank/drug/DB00512/identifier/pharmgkb/
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n21http://linked.opendata.cz/resource/drugbank/drug/DB00512/identifier/pubchem-compound/
n26http://linked.opendata.cz/ontology/mesh/
n3http://linked.opendata.cz/ontology/drugbank/
n12http://www.rxlist.com/cgi/generic2/
n4http://linked.opendata.cz/resource/drugbank/property/
xsdhhttp://www.w3.org/2001/XMLSchema#
n24http://linked.opendata.cz/resource/drugbank/drug/DB00512/identifier/kegg-drug/
n19http://linked.opendata.cz/resource/drugbank/drug/DB00512/identifier/pubchem-substance/
n6http://linked.opendata.cz/resource/drugbank/drug/DB00512/identifier/drugbank/
n15http://linked.opendata.cz/resource/atc/
n14http://linked.opendata.cz/ontology/sukl/drug/

Statements

Subject Item
n2:DB00512
rdf:type
n3:Drug
n3: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. [PubChem]
n3:dosage
n18:271B62A5-363D-11E5-9242-09173F13E4C5 n18:271B62AE-363D-11E5-9242-09173F13E4C5 n18:271B62AF-363D-11E5-9242-09173F13E4C5 n18:271B62B0-363D-11E5-9242-09173F13E4C5 n18:271B62B1-363D-11E5-9242-09173F13E4C5 n18:271B62B2-363D-11E5-9242-09173F13E4C5 n18:271B62B3-363D-11E5-9242-09173F13E4C5 n18:271B62A6-363D-11E5-9242-09173F13E4C5 n18:271B62A7-363D-11E5-9242-09173F13E4C5 n18:271B62A8-363D-11E5-9242-09173F13E4C5 n18:271B62A9-363D-11E5-9242-09173F13E4C5 n18:271B62AA-363D-11E5-9242-09173F13E4C5 n18:271B62AB-363D-11E5-9242-09173F13E4C5 n18:271B62AC-363D-11E5-9242-09173F13E4C5 n18:271B62AD-363D-11E5-9242-09173F13E4C5 n18:271B62B4-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# Schäfer, Martina, Thomas R Schneider, and George M Sheldrick. 1996. Crystal structure of vancomycin. Structure 4, no. 12 (December 15): 1509-1515. "DOI:10.1016/S0969-2126(96)00156-6":http://dx.doi.org/10.1016/S0969-2126(96)00156-6. # Levine DP: Vancomycin: a history. Clin Infect Dis. 2006 Jan 1;42 Suppl 1:S5-12. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/16323120 # Small PM, Chambers HF: Vancomycin for Staphylococcus aureus endocarditis in intravenous drug users. Antimicrob Agents Chemother. 1990 Jun;34(6):1227-31. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/2393284 # Gonzalez C, Rubio M, Romero-Vivas J, Gonzalez M, Picazo JJ: Bacteremic pneumonia due to Staphylococcus aureus: A comparison of disease caused by methicillin-resistant and methicillin-susceptible organisms. Clin Infect Dis. 1999 Nov;29(5):1171-7. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/10524959 # Sivagnanam S, Deleu D: Red man syndrome. Crit Care. 2003 Apr;7(2):119-20. Epub 2002 Dec 23. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/12720556 # Cantu TG, Yamanaka-Yuen NA, Lietman PS: Serum vancomycin concentrations: reappraisal of their clinical value. Clin Infect Dis. 1994 Apr;18(4):533-43. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/8038306
n3:group
approved
n3:halfLife
Half-life in normal renal patients is approximately 6 hours (range 4 to 11 hours). In anephric patients, the average half-life of elimination is 7.5 days.
n3:indication
For the treatment of serious or severe infections caused by susceptible strains of methicillin-resistant (beta-lactam-resistant) staphylococci.
n3:manufacturer
n7:271B6297-363D-11E5-9242-09173F13E4C5 n7:271B6295-363D-11E5-9242-09173F13E4C5 n7:271B6296-363D-11E5-9242-09173F13E4C5 n7:271B6293-363D-11E5-9242-09173F13E4C5 n7:271B6294-363D-11E5-9242-09173F13E4C5 n7:271B6291-363D-11E5-9242-09173F13E4C5 n7:271B6292-363D-11E5-9242-09173F13E4C5 n7:271B628F-363D-11E5-9242-09173F13E4C5 n7:271B6290-363D-11E5-9242-09173F13E4C5 n7:271B628E-363D-11E5-9242-09173F13E4C5
owl:sameAs
n17:DB00512 n28:DB00512
dcterms:title
Vancomycin
adms:identifier
n6:DB00512 n8:28001 n9:389935 n19:46505261 n20:PA451850 n21:14969 n22:0338-3551-48 n23:C06689 n24:D00212 n29:Vancomycin
n3:mechanismOfAction
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.
n3:packager
n7:271B6285-363D-11E5-9242-09173F13E4C5 n7:271B6286-363D-11E5-9242-09173F13E4C5 n7:271B6282-363D-11E5-9242-09173F13E4C5 n7:271B6284-363D-11E5-9242-09173F13E4C5 n7:271B6289-363D-11E5-9242-09173F13E4C5 n7:271B628A-363D-11E5-9242-09173F13E4C5 n7:271B6287-363D-11E5-9242-09173F13E4C5 n7:271B6288-363D-11E5-9242-09173F13E4C5 n7:271B628D-363D-11E5-9242-09173F13E4C5 n7:271B628B-363D-11E5-9242-09173F13E4C5 n7:271B628C-363D-11E5-9242-09173F13E4C5 n7:271B627D-363D-11E5-9242-09173F13E4C5 n7:271B6280-363D-11E5-9242-09173F13E4C5 n7:271B6281-363D-11E5-9242-09173F13E4C5 n7:271B627E-363D-11E5-9242-09173F13E4C5 n7:271B627F-363D-11E5-9242-09173F13E4C5 n7:271B6283-363D-11E5-9242-09173F13E4C5
n3:routeOfElimination
In the first 24 hours, about 75% of an administered dose of vancomycin is excreted in urine by glomerular filtration.
n3:synonym
Vancomycin Vancomycinum Vancomycine (2.2Sp,3.5sa,2.6sp)-O(4.2),C(3.4):c(5.4),O(4.6):c(3.5),C(2.7)-tricyclo[N-methyl-D-leucyl-3-chloro-(R)-beta-hydroxy-D-tyrosyl-L-asparaginyl-D-2-(4-{[2-O-(3-amino-2,3,6-trideoxy-3-C-methyl-alpha-L-lyxo-hexopyranosyl)-beta-D-glucopyranosyl]oxy}phenyl)glycyl-D-2-(4-hydroxyphenyl)glycyl-3-chloro-(R)-beta-hydroxy-L-tyrosyl-L-2-(3,5-dihydroxyphenyl)glycine] Vancocin Vancomicina (1S,2R,18R,22S,25R,28R,40S)-22-(2-amino-2-Oxoethyl)-48-[2-O-(3-amino-2,3,6-trideoxy-3-methyl-alpha-L-lyxo-hexopyranosyl)-beta-D-glucopyranosyloxy]-5,15-dichloro-2,18,32,35,37-pentahydroxy-19-[(N-methyl-D-leucyl)amino]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.2(3,6).2(14,17).1(8,12).1(29,33).0(10,25).0(34,39)]pentaconta-3,5,8(48),9,11,14,16,29(45),30,32,34,36,38,46,49-pentadecaene-40-carboxylic acid
n3:toxicity
The oral LD<sub>50</sub> in mice is 5000 mg/kg. The median lethal intravenous dose is 319 mg/kg in rats and 400 mg/kg in mice.
n14:hasAHFSCode
n30:08-12-28-16
n3:proteinBinding
Approximately 55% serum protein bound.
n3:salt
n3:synthesisReference
# Boger DL. Vancomycin, teicoplanin, and ramoplanin: synthetic and mechanistic studies. Med Res Rev. 2001 Sep;21(5):356-81. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/11579438
n26:hasConcept
n27:M0022517
foaf:page
n12:vancomycin.htm n25:vancomycin.html
n3:IUPAC-Name
n4:271B62B9-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B62BF-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B62BE-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B62BB-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B62BC-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B62BD-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B62B7-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B62B8-363D-11E5-9242-09173F13E4C5 n4:271B62CF-363D-11E5-9242-09173F13E4C5 n4:271B62B5-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B62B6-363D-11E5-9242-09173F13E4C5
n14:hasATCCode
n15:A07AA09 n15:J01XA01
n3:H-Bond-Acceptor-Count
n4:271B62C5-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B62C6-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B62C0-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B62C1-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B62C3-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B62C2-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B62C4-363D-11E5-9242-09173F13E4C5
n3:absorption
Poorly absorbed from gastrointestinal tract, however systemic absorption (up to 60%) may occur following intraperitoneal administration.
n3:affectedOrganism
Enteric bacteria and other eubacteria Chlamydia trachomatis Chlamydia psittaci Mycoplasma pneumoniae Neisseria gonorrhoeae Corynebacterium diphtheriae Streptococcus pyogenes Bordetella pertussis Treponema pallidum Chlamydia pneumoniae Legionella pneumophila
n3:casRegistryNumber
1404-90-6
n3:category
n3:clearance
* 0.06 L/kg/h
n3:containedIn
n10:271B629A-363D-11E5-9242-09173F13E4C5 n10:271B629B-363D-11E5-9242-09173F13E4C5 n10:271B6298-363D-11E5-9242-09173F13E4C5 n10:271B6299-363D-11E5-9242-09173F13E4C5 n10:271B629E-363D-11E5-9242-09173F13E4C5 n10:271B629F-363D-11E5-9242-09173F13E4C5 n10:271B629C-363D-11E5-9242-09173F13E4C5 n10:271B629D-363D-11E5-9242-09173F13E4C5 n10:271B62A2-363D-11E5-9242-09173F13E4C5 n10:271B62A3-363D-11E5-9242-09173F13E4C5 n10:271B62A0-363D-11E5-9242-09173F13E4C5 n10:271B62A1-363D-11E5-9242-09173F13E4C5 n10:271B62A4-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n4:271B62CB-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B62CD-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B62CE-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B62CA-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B62C9-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B62CC-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B62BA-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n4:271B62C7-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B62C8-363D-11E5-9242-09173F13E4C5