Clavulanic acid 1749180 218287195 2008-06-09T23:36:06Z Runnermonkey 4118811 Reverted 1 edit by [[Special:Contributions/125.237.67.37|125.237.67.37]]; Reverting unsourced & unencyclopedic material.. is this a joke?. ([[WP:TW|TW]]) {{drugbox | |width=200 |image=Clavulanic acid structure.svg |IUPAC_name = (2''R'',5''R'',''Z'')-3-(2-hydroxyethylidene)-<br />7-oxo-4-oxa-1-aza-bicyclo[3.2.0]<br />heptane-2-carboxylic acid |CAS_number = 58001-44-8 | ATC_prefix=J01 | ATC_suffix=? | PubChem=42617 | DrugBank=APRD00049 | C=8 | H=9 | N=1 | O=5 |molecular_weight = 199.16 |bioavailability = "well absorbed" |metabolism = hepatic (extensive) |elimination_half-life = 1 hour |excretion = [[renal]] (30–40%) |pregnancy_category = B ([[USA]])<br />B1 ([[Australia|Aust]]) |legal_status = Schedule 4 ([[Australia|Aust]]) |routes_of_administration = oral, [[IV]] }} '''Clavulanic acid''' ([[International Nonproprietary Name|rINN]]) ({{pronEng|klævjuːˌlænɨk ˈæsɨd}}) is a [[beta-lactamase inhibitor]] ([[GlaxoSmithKline]] formerly [[Beecham (pharmaceutical company)|Beecham]]) sometimes combined with [[penicillin]] group [[antibiotic]]s 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 [Clavulox]) 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]]. ==History== Clavulanic acid was invented around 1974/75 by British scientists working at the drug company [[Beecham (pharmaceutical company)|Beecham]]. After several attempts Beecham finally filed for US patent protection for the drug in 1981, and U.S. Patents 4,525,352, 4,529,720 and 4,560,552 were granted in 1985. ==Mechanism of action== Clavulanic acid has negligible intrinsic antimicrobial activity, despite sharing the β-lactam ring that is characteristic of [[beta-lactam antibiotic]]s. However, the similarity in chemical structure allows the molecule to act as a [[competitive inhibitor]] of [[beta-lactamase]]s secreted by certain bacteria to confer resistance to beta-lactam antibiotics. This inhibition restores the antimicrobial activity of beta-lactam antibiotics against a lactamase-secreting resistant bacteria. Despite this, some bacterial strains have emerged that are even resistant to such combinations. ==Adverse effects== The use of clavulanic acid with penicillins has been associated with an increased incidence of [[cholestasis|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 [[United Kingdom|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. {{PenicillinAntiBiotics}} [[Category:Beta-lactamase inhibitors]] [[de:Clavulansäure]] [[es:Ácido clavulánico]] [[fr:Acide clavulanique]] [[it:Acido clavulanico]] [[nl:Clavulaanzuur]] [[ja:クラブラン酸]] [[pl:Kwas klawulanowy]] [[pt:Ácido clavulânico]] [[sr:Клавуланска киселина]]