Clavulanic acid

Clavulanic acid is a beta-lactam compound that inhibits many bacterial beta-lactamases. It is commonly combined with antibiotics such as amoxicillin to protect them from enzymatic breakdown.

Beta-lactamase: A bacterial enzyme that inactivates many beta-lactam antibiotics by opening their beta-lactam ring. Clavulanic acid inhibits many of these enzymes, protecting susceptible antibiotics.
Amoxicillin/clavulanate: A combination antibiotic containing the penicillin amoxicillin and the beta-lactamase inhibitor clavulanate. It is the best-known medicine pairing clavulanate with a beta-lactam antibiotic.
Streptomyces clavuligerus: A soil bacterium that produces clavulanic acid and other biologically active compounds. Researchers isolated clavulanic acid from cultures of this organism.
Extended-spectrum beta-lactamase: A beta-lactamase that can hydrolyze many extended-spectrum penicillins and cephalosporins. Clavulanate inhibits some enzymes in this group, but not reliably enough for every infection.
Mechanism-based inhibition: Enzyme inhibition in which the enzyme converts an inhibitor into a reactive species that then disables it. Clavulanic acid is activated during catalysis and forms a lasting bond with beta-lactamase.
Amoxicillin: A penicillin antibiotic used to treat a range of bacterial infections. Clavulanate protects amoxicillin from some beta-lactamases that would otherwise inactivate it.
Beecham Group: A British pharmaceutical company that developed and commercialized several penicillin medicines. Its researchers identified clavulanic acid and developed it for clinical use.
Clavulanate-associated diarrhea: Diarrhea linked to medicines containing clavulanate, a frequent adverse effect of amoxicillin/clavulanate. Adding clavulanate can increase gastrointestinal adverse effects compared with amoxicillin alone.
Beta-lactam ring: A four-membered cyclic amide structure found in penicillins, cephalosporins, and related compounds. Its strained ring helps clavulanic acid react with beta-lactamase.
Co-amoxiclav: The international and British name for the fixed combination of amoxicillin and clavulanic acid. This name identifies the same combination often called amoxicillin/clavulanate.

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Penicillin-binding proteinsRelated: It can preserve an antibiotic's access to penicillin-binding proteins by inhibiting some drug-destroying enzymes.