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Namespace Prefixes

PrefixIRI
n2http://linked.opendata.cz/resource/drugbank/drug/
dctermshttp://purl.org/dc/terms/
n13http://linked.opendata.cz/resource/drugbank/drug/DB00739/identifier/chemspider/
n5http://linked.opendata.cz/resource/drugbank/company/
n12http://linked.opendata.cz/resource/drugbank/drug/DB00739/identifier/chebi/
n18http://linked.opendata.cz/resource/drugbank/drug/DB00739/identifier/wikipedia/
n19http://linked.opendata.cz/resource/drugbank/drug/DB00739/identifier/pharmgkb/
n15http://bio2rdf.org/drugbank:
n11http://linked.opendata.cz/resource/drugbank/drug/DB00739/identifier/kegg-compound/
admshttp://www.w3.org/ns/adms#
n9http://linked.opendata.cz/resource/drugbank/drug/DB00739/identifier/pubchem-compound/
n21http://wifo5-03.informatik.uni-mannheim.de/drugbank/resource/drugs/
n7http://linked.opendata.cz/resource/drugbank/drug/DB00739/identifier/pubchem-substance/
rdfhttp://www.w3.org/1999/02/22-rdf-syntax-ns#
n8http://linked.opendata.cz/resource/drugbank/drug/DB00739/identifier/kegg-drug/
owlhttp://www.w3.org/2002/07/owl#
n3http://linked.opendata.cz/ontology/drugbank/
n10http://linked.opendata.cz/resource/drugbank/drug/DB00739/identifier/drugbank/
n4http://linked.opendata.cz/resource/drugbank/property/
xsdhhttp://www.w3.org/2001/XMLSchema#
n17http://linked.opendata.cz/resource/atc/
n16http://linked.opendata.cz/ontology/sukl/drug/

Statements

Subject Item
n2:DB00739
rdf:type
n3:Drug
n3:description
Hetacillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Hetacillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Hetacillin results from the inhibition of cell wall synthesis and is mediated through Hetacillin binding to penicillin binding proteins (PBPs). Hetacillin has been withdrawn from the market since it has been discovered that it has no therapeutic advantage compared to non-ester derivatives like ampicillin.
n3:group
approved withdrawn
n3:indication
Hetacillin is a beta-lactam antibiotic prodrug used to treat bacterial infections. In the body it gets converted to ampicillin.
n3:manufacturer
n5:271B5353-363D-11E5-9242-09173F13E4C5
owl:sameAs
n15:DB00739 n21:DB00739
dcterms:title
Hetacillin
adms:identifier
n7:46504545 n8:D01074 n9:443387 n10:DB00739 n11:C11729 n12:5683 n13:391616 n18:Hetacillin n19:PA164746559
n3:mechanismOfAction
Hetacillin is a semisynthetic penicillin prodrug which itself has no antibacterial activity, but is converted in the body to ampicillin and has actions and uses similar to those of ampicillin. Hetacillin is prepared by reacting ampicillin with acetone. Ampicillin rapidly decomposes because of the intramolecular attack of the side chain amino group on the lactam ring. Hetacillin locks up the offending amino group and prevents the decompolsition Hetacillin, once hydrolyzed to ampicillin (and acetone) binds to the penicillin binding proteins found in susceptible bacteria. This inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins. Targets below reflect ampicillin targets.
n3:synonym
Phenazacillin Hetacilina Hétacilline 6beta-[(4R)-2,2-Dimethyl-5-oxo-4-phenylimidazolidin-1-yl]penicillanic acid (2S,5R,6R)-6-[(4R)-2,2-Dimethyl-5-oxo-4-phenylimidazolidin-1-yl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Hetacillin Hetacillinum
n3:salt
n3:synthesisReference
U.S. Patent 3,198,804.
n3:IUPAC-Name
n4:271B5358-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B535E-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B535D-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B535A-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B535B-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B535C-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B5356-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B536F-363D-11E5-9242-09173F13E4C5 n4:271B5354-363D-11E5-9242-09173F13E4C5 n4:271B5357-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B5355-363D-11E5-9242-09173F13E4C5
n16:hasATCCode
n17:J01CA18
n3:H-Bond-Acceptor-Count
n4:271B5364-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B5365-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B535F-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B5360-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B5362-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B5361-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B5363-363D-11E5-9242-09173F13E4C5
n3:affectedOrganism
Enteric bacteria and other eubacteria
n3:casRegistryNumber
3511-16-8
n3:category
n3:Bioavailability
n4:271B536A-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B536C-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B536D-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n4:271B536E-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B5369-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B5368-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B536B-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B5359-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n4:271B5366-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B5367-363D-11E5-9242-09173F13E4C5