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Namespace Prefixes

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Statements

Subject Item
n2:DB00766
rdf:type
n3:Drug
n3:description
Clavulanic acid and its salts and esters. The acid is a suicide inhibitor of bacterial beta-lactamase enzymes from Streptomyces clavuligerus. Administered alone, it has only weak antibacterial activity against most organisms, but given in combination with beta-lactam antibiotics prevents antibiotic inactivation by microbial lactamase. [PubChem]
n3:group
approved
n3:halfLife
1.0 hour
n3:indication
For use with Amoxicillin, clavulanic acid is suitable for the treatment of infections with <i>Staph. aureus</i> and <i>Bacteroides fragilis</i>, or with beta-lactamase producing <i>H. influenzae</i> and <i>E. coli</i>.
owl:sameAs
n9:DB00766 n12:DB00766
dcterms:title
Clavulanate
adms:identifier
n6:Clavulanate n7:PA164742987 n14:5280980 n15:46508845 n16:DB00766 n17:C06662 n18:3736 n19:4444466
n3:mechanismOfAction
Clavulanic acid competitively and irreversibly inhibits a wide variety of beta-lactamases, commonly found in microorganisms resistant to penicillins and cephalosporins. Binding and irreversibly inhibiting the beta-lactamase results in a restauration of the antimicrobial activity of beta-lactam antibiotics against lactamase-secreting-resistant bacteria. By inactivating beta-lactamase (the bacterial resistance protein), the accompanying penicillin/cephalosporin drugs may be made more potent as well.
n3:packager
n10:271B5C63-363D-11E5-9242-09173F13E4C5 n10:271B5C64-363D-11E5-9242-09173F13E4C5 n10:271B5C62-363D-11E5-9242-09173F13E4C5 n10:271B5C67-363D-11E5-9242-09173F13E4C5 n10:271B5C68-363D-11E5-9242-09173F13E4C5 n10:271B5C65-363D-11E5-9242-09173F13E4C5 n10:271B5C66-363D-11E5-9242-09173F13E4C5 n10:271B5C4C-363D-11E5-9242-09173F13E4C5 n10:271B5C4D-363D-11E5-9242-09173F13E4C5 n10:271B5C50-363D-11E5-9242-09173F13E4C5 n10:271B5C51-363D-11E5-9242-09173F13E4C5 n10:271B5C4E-363D-11E5-9242-09173F13E4C5 n10:271B5C4F-363D-11E5-9242-09173F13E4C5 n10:271B5C54-363D-11E5-9242-09173F13E4C5 n10:271B5C55-363D-11E5-9242-09173F13E4C5 n10:271B5C52-363D-11E5-9242-09173F13E4C5 n10:271B5C53-363D-11E5-9242-09173F13E4C5 n10:271B5C58-363D-11E5-9242-09173F13E4C5 n10:271B5C59-363D-11E5-9242-09173F13E4C5 n10:271B5C56-363D-11E5-9242-09173F13E4C5 n10:271B5C57-363D-11E5-9242-09173F13E4C5 n10:271B5C61-363D-11E5-9242-09173F13E4C5 n10:271B5C5A-363D-11E5-9242-09173F13E4C5 n10:271B5C60-363D-11E5-9242-09173F13E4C5 n10:271B5C6B-363D-11E5-9242-09173F13E4C5 n10:271B5C69-363D-11E5-9242-09173F13E4C5 n10:271B5C6A-363D-11E5-9242-09173F13E4C5 n10:271B5C5C-363D-11E5-9242-09173F13E4C5 n10:271B5C5D-363D-11E5-9242-09173F13E4C5 n10:271B5C5B-363D-11E5-9242-09173F13E4C5 n10:271B5C6C-363D-11E5-9242-09173F13E4C5 n10:271B5C6D-363D-11E5-9242-09173F13E4C5 n10:271B5C5E-363D-11E5-9242-09173F13E4C5 n10:271B5C4A-363D-11E5-9242-09173F13E4C5 n10:271B5C5F-363D-11E5-9242-09173F13E4C5 n10:271B5C4B-363D-11E5-9242-09173F13E4C5 n10:271B5C70-363D-11E5-9242-09173F13E4C5 n10:271B5C71-363D-11E5-9242-09173F13E4C5 n10:271B5C6E-363D-11E5-9242-09173F13E4C5 n10:271B5C6F-363D-11E5-9242-09173F13E4C5 n10:271B5C74-363D-11E5-9242-09173F13E4C5 n10:271B5C75-363D-11E5-9242-09173F13E4C5 n10:271B5C72-363D-11E5-9242-09173F13E4C5 n10:271B5C73-363D-11E5-9242-09173F13E4C5
n3:synonym
Acidum clavulanicum Clavulanic Acid Clavulansaeure (2R,3Z,5R)-3-(2-HYDROXYETHYLIDENE)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Clavulanate Acide clavulanique (Z)-(2R,5R)-3-(2-Hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo(3.2.0)heptane-2-carboxylic acid Antibiotic mm 14151 MM 14151 Acido clavulanico
n3:toxicity
Gastrointestinal symptoms including stomach and abdominal pain, vomiting, and diarrhea. Rash, hyperactivity, or drowsiness have also been observed in a small number of patients
n3:mixture
n13:271B5C49-363D-11E5-9242-09173F13E4C5 n13:271B5C47-363D-11E5-9242-09173F13E4C5 n13:271B5C48-363D-11E5-9242-09173F13E4C5 n13:271B5C45-363D-11E5-9242-09173F13E4C5 n13:271B5C46-363D-11E5-9242-09173F13E4C5
n3:proteinBinding
Low (22 to 30%)
n3:synthesisReference
Dennis Edward Clark, Shaukat Hussain Malik, Paul Gerard Butterly, Clive Elton Badman, Jeffrey David Haseler, "Process for preparing potassium clavulanate in rossette form." U.S. Patent US5750685, issued April, 1978.
n20:hasConcept
n21:M0372713
n3:IUPAC-Name
n4:271B5C7A-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B5C80-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B5C7F-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B5C7C-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B5C7D-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B5C7E-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B5C90-363D-11E5-9242-09173F13E4C5 n4:271B5C78-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B5C92-363D-11E5-9242-09173F13E4C5 n4:271B5C76-363D-11E5-9242-09173F13E4C5 n4:271B5C79-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B5C77-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Acceptor-Count
n4:271B5C86-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B5C87-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B5C81-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B5C82-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B5C84-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B5C83-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B5C85-363D-11E5-9242-09173F13E4C5
n3:absorption
75%
n3:affectedOrganism
Enteric bacteria and other eubacteria
n3:casRegistryNumber
58001-44-8
n3:category
n3:Bioavailability
n4:271B5C8C-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B5C8E-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B5C8F-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n4:271B5C91-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B5C8B-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B5C8A-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B5C8D-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B5C7B-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n4:271B5C88-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B5C89-363D-11E5-9242-09173F13E4C5