Clavulanic acid

Clavulanic acid

File:Clavulanic acid structure.svg
Clinical data
Pregnancy category	B (USA) B1 (Aust)
Routes of administration	oral, IV
ATC code	J01? (WHO)
Legal status
Legal status	Schedule 4 (Aust)
Pharmacokinetic data
Bioavailability	"well absorbed"
Metabolism	hepatic (extensive)
Elimination half-life	1 hour
Excretion	renal (30–40%)
Identifiers
IUPAC name (2R,5R,Z)-3-(2-hydroxyethylidene)- 7-oxo-4-oxa-1-aza-bicyclo[3.2.0] heptane-2-carboxylic acid
CAS Number	58001-44-8
PubChem CID	42617
DrugBank	APRD00049
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C8H9NO5
Molar mass	199.16

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Clavulanic acid (rINN) (IPA: Template:IPA) is a beta-lactamase inhibitor (GlaxoSmithKline formerly Beecham) sometimes combined with penicillin group antibiotics to overcome certain types of antibiotic resistance. Specifically, it is used to overcome resistance in bacteria that secrete beta-lactamase enzymes, which otherwise inactivate most penicillins. Most commonly, the potassium salt potassium clavulanate is combined with amoxicillin (co-amoxiclav [brand name Augmentin] or the veterinary formulation Synulox from Pfizer) or ticarcillin.

The name is derived from the Streptomyces clavuligerus microorganisms from which clavulanic acid is derived. Clavulanic acid is biosynthetically generated from the amino acid arginine and the sugar glyceraldehyde 3-phosphate.

Mechanism of action

Clavulanic acid has negligible intrinsic antimicrobial activity, despite sharing the β-lactam ring that is characteristic of beta-lactam antibiotics. However, the similarity in chemical structure allows the molecule to act as a competitive inhibitor of beta-lactamases secreted by certain bacteria to confer resistance to beta-lactam antibiotics. This inhibition restores the antimicrobial activity of beta-lactam antibiotics against β-lactamase-secreting resistant bacteria. Despite this, some bacterial strains have emerged that are resistant to even such combinations.

Adverse effects

The use of clavulanic acid with penicillins has been associated with an increased incidence of cholestatic jaundice and acute hepatitis during therapy or shortly after, particularly in men and those aged over 65 years. The associated jaundice is usually self-limiting and very rarely fatal. (Joint Formulary Committee, 2004)

The UK Committee on Safety of Medicines (CSM) recommends that treatments such as amoxicillin/clavulanic acid preparations should be reserved for bacterial infections likely to be caused by amoxicillin-resistant β-lactamase-producing strains, and that treatment should not normally exceed 14 days.

References

• Joint Formulary Committee. British National Formulary, 47th edition. London: British Medical Association and Royal Pharmaceutical Society of Great Britain; 2004.