Compound ID | 1870

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Clavulanic acid

Class: Beta-lactamase inhibitor

Agent Type: Natural product; Small molecule; Direct acting; Antibiotic adjuvant;
Mechanism of action: Binds irreversibly to beta-lactamases, mainly class A enzymes
Combined with other compounds: Yes
Description: Natural product from Streptomyces; only available as a combination product, oral and parenteral application; clavam, bicyclic beta-lactam without a penicillin or cephalosporin nucleus; no intrinsic antibacterial activity
Year first mentioned: 1976
Highest development stage: Approved
Development status: Approved
Chemical structure(s):
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Molecular weight: 199.16
Iso. SMILES: C1[C@@H]2N(C1=O)[C@H](/C(=C/CO)/O2)C(=O)O
InChI Key: HZZVJAQRINQKSD-PBFISZAISA-N
Can. SMILES: C(=C/1\[C@H](C(=O)O)N2C(=O)C[C@H]2O1)/CO
InChI: 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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/5280980
Guide to Pharmacology: clavulanic acid
Citations:
  • https://pubs.acs.org/doi/10.1021/acs.jmedchem.9b01279
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2806661/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC358033/pdf/cmr00055-0121.pdf
  • https://www.jstage.jst.go.jp/article/antibiotics1968/29/6/29_6_668/_pdf/-char/en

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