J01

(2R,3Z,5R)-3-(2-HYDROXYETHYLIDENE)-7-OXO-4-OXA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID

Created: 2006-11-29
Last modified:  2020-06-05

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Chemical Details

Formal Charge0
Atom Count23
Chiral Atom Count2
Bond Count24
Aromatic Bond Count0
2D diagram of J01

Chemical Component Summary

Name(2R,3Z,5R)-3-(2-HYDROXYETHYLIDENE)-7-OXO-4-OXA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID
SynonymsCLAVULANIC ACID
Systematic Name (OpenEye OEToolkits)(2R,3Z,5R)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
FormulaC8 H9 N O5
Molecular Weight199.161
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=C2N1C(C(/OC1C2)=C/CO)C(=O)O
SMILESCACTVS3.341OCC=C1O[CH]2CC(=O)N2[CH]1C(O)=O
SMILESOpenEye OEToolkits1.5.0C1C2N(C1=O)C(C(=CCO)O2)C(=O)O
Canonical SMILESCACTVS3.341 OC\C=C1/O[C@@H]2CC(=O)N2[C@H]1C(O)=O
Canonical SMILESOpenEye OEToolkits1.5.0 C1[C@@H]2N(C1=O)[C@H](/C(=C/CO)/O2)C(=O)O
InChIInChI1.03 InChI=1S/C8H9NO5/c10-2-1-4-7(8(12)13)9-5(11)3-6(9)14-4/h1,6-7,10H,2-3H2,(H,12,13)/b4-1-/t6-,7-/m1/s1
InChIKeyInChI1.03 HZZVJAQRINQKSD-PBFISZAISA-N

Drug Info: DrugBank

DrugBank IDDB00766 
NameClavulanic acid
Groups
  • approved
  • vet_approved
DescriptionClavulanic acid is a beta-lactamase inhibitor that is frequently combined with [Amoxicillin] or [Ticarcillin] to fight antibiotic resistance by preventing their degradation by beta-lactamase enzymes, broadening their spectrum of susceptible bacterial infections.[T665] Clavulanic acid is derived from the organism Streptomyces clavuligerus.[A182228]When it is combined with amoxicillin, clavulanic acid is frequently known as Augmentin, Co-Amoxiclav, or Clavulin.[L7880,L7904,L7910]
Synonyms
  • (Z)-(2R,5R)-3-(2-Hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
  • Acide clavulanique
  • Acidum clavulanicum
  • Clavulanate
  • Clavulansäure
Brand Names
  • Amoxicillin and Calvulanate Potassium
  • Novo-clavamoxin 125
  • Apo-amoxi Clav 125mg/31.25mg Per 5ml
  • Clavulin 400
  • Augmentin Es 600
IndicationClavulanic acid combined with other antibiotics is indicated to prevent the development of drug-resistant strains of bacteria and promotes their therapeutic antibacterial effects.[L7880,L7904] The following conditions, when they produced beta-lactamases, have been treated with a combination of amoxicillin and clavulanic acid or ticarcillin and clavulanic acid[L7880,L7904]: Acute otitis media caused by H. influenzae and M. catarrhalis Sinusitis due to H. influenzae and M. catarrhalis Lower respiratory tract infections due to Haemophilus influenzae, S.aureus, Klebsiella species, and Moraxella catarrhalis Skin and skin structure infections caused by Staphylococcus aureus, Escherichia coli, and Klebsiella species Urinary Tract Infections due to E. coli, Klebsiella species of bacteria, and Enterobacter species of bacteria, S.marcescens, or S.aureus Gynecologic infections due to a variety of bacteria, including P.melaninogenicus, Enterobacter species, E.Coli species, Klebsiella species, S. aureus, S.epidermidis Septicemia due to a variety of bacteria, including Klebsiella species, E.Coli species, S.aureus, or Pseudomonas species Bone and joint infections due to S.aureus Intraabdominal infections due to E.Coli, K.pnemoniae, or B.fragilis group **A note on susceptibility** It should be noted that it is only to be administered in infections that are confirmed or highly likely to be caused by susceptible bacteria. Culture and susceptibility tests should be performed if possible and used in selecting whether this antibiotic is prescribed. When beta-lactamase enzyme production is not detected during microbiological testing, clavulanic acid should not be used. When these tests are not available patterns of local infection and susceptibility may be used to determine the appropriateness of using clavulanic acid.[L7880] Ticarcillin with clavulanate has shown particular efficacy in mixed infections in addition to empiric therapy before determining the susceptibility of causative organisms. The ticarcillin-clavulanic acid combination may prove to be an effective single-agent antibiotic therapy to treat infections where a regimen of several drugs may normally be used.[L7904]
Categories
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • beta-Lactamase Inhibitors
  • beta-Lactams
  • Enzyme Inhibitors
CAS number58001-44-8

Drug Targets

NameTarget SequencePharmacological ActionActions
Bacterial beta-lactamase enzymes-unknowninhibitor
Sodium/glucose cotransporter 1MDSSTWSPKTTAVTRPVETHELIRNAADISIIVIYFVVVMAVGLWAMFST...unknowninducer
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 5280980
ChEMBL CHEMBL777
ChEBI CHEBI:48947