Clavulanic acid

Clavulanic acid is a β-lactam drug that functions as a mechanism-based β-lactamase inhibitor. While not effective by itself as an antibiotic, when combined with penicillin-group antibiotics, it can overcome antibiotic resistance in bacteria that secrete β-lactamase, which otherwise inactivates most penicillins.

Clavulanic acid
Clinical data
Pronunciation/ˌklævjʊˈlænɪk/
AHFS/Drugs.comInternational Drug Names
Pregnancy
category
  • AU: B1
Routes of
administration		Oral, IV
ATC code
  • J01CR (WHO) (combinations with penicillins)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability"Well absorbed"
MetabolismHepatic (extensive)
Elimination half-life1 hour
ExcretionRenal (30–40%)
Identifiers
  • (2R,5R,Z)-3-(2-Hydroxyethylidene)-7-oxo-4-oxa-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.055.500
Chemical and physical data
FormulaC8H9NO5
Molar mass199.162 g·mol−1
3D model (JSmol)
SMILES
  • O=C2N1[C@H](C(/O[C@@H]1C2)=C/CO)C(=O)O
  • 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 Y
  • Key:HZZVJAQRINQKSD-PBFISZAISA-N Y
  (verify)

In its most common preparations, potassium clavulanate (clavulanic acid as a salt of potassium) is combined with:

  • amoxicillin (co-amoxiclav, trade names Augmentin, Clavulin, Tyclav, Clavaseptin (veterinary), Clavamox (veterinary), Synulox (veterinary), and others)
  • ticarcillin (co-ticarclav, trade name Timentin)

Clavulanic acid was patented in 1974.

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