Clavulanic acid: Difference between revisions
m Protected "Clavulanic acid": Protecting pages from unwanted edits ([edit=sysop] (indefinite) [move=sysop] (indefinite)) |
m Bot: Automated text replacement (-{{SIB}} + & -{{EH}} + & -{{EJ}} + & -{{Editor Help}} + & -{{Editor Join}} +) |
||
| Line 19: | Line 19: | ||
}} | }} | ||
{{SI}} | {{SI}} | ||
'''Clavulanic acid''' ([[International Nonproprietary Name|rINN]]) ([[International Phonetic Alphabet|IPA]]: {{IPA|[klævjuˌlænɪk ˈæsəd]}}) 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 [[ticarcillin]]. | '''Clavulanic acid''' ([[International Nonproprietary Name|rINN]]) ([[International Phonetic Alphabet|IPA]]: {{IPA|[klævjuˌlænɪk ˈæsəd]}}) 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 [[ticarcillin]]. | ||
| Line 38: | Line 38: | ||
{{PenicillinAntiBiotics}} | {{PenicillinAntiBiotics}} | ||
[[Category:Beta-lactamase inhibitors]] | [[Category:Beta-lactamase inhibitors]] | ||
[[de:Clavulansäure]] | [[de:Clavulansäure]] | ||
[[ja:クラブラン酸]] | [[ja:クラブラン酸]] | ||
Latest revision as of 23:56, 8 August 2012
| File:Clavulanic acid structure.svg | |
| Clinical data | |
|---|---|
| Pregnancy category | |
| Routes of administration | oral, IV |
| ATC code | |
| Legal status | |
| Legal status |
|
| Pharmacokinetic data | |
| Bioavailability | "well absorbed" |
| Metabolism | hepatic (extensive) |
| Elimination half-life | 1 hour |
| Excretion | renal (30–40%) |
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| DrugBank | |
| E number | {{#property:P628}} |
| ECHA InfoCard | {{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value). |
| Chemical and physical data | |
| Formula | C8H9NO5 |
| Molar mass | 199.16 |
|
WikiDoc Resources for Clavulanic acid |
|
Articles |
|---|
|
Most recent articles on Clavulanic acid Most cited articles on Clavulanic acid |
|
Media |
|
Powerpoint slides on Clavulanic acid |
|
Evidence Based Medicine |
|
Clinical Trials |
|
Ongoing Trials on Clavulanic acid at Clinical Trials.gov Trial results on Clavulanic acid Clinical Trials on Clavulanic acid at Google
|
|
Guidelines / Policies / Govt |
|
US National Guidelines Clearinghouse on Clavulanic acid NICE Guidance on Clavulanic acid
|
|
Books |
|
News |
|
Commentary |
|
Definitions |
|
Patient Resources / Community |
|
Patient resources on Clavulanic acid Discussion groups on Clavulanic acid Patient Handouts on Clavulanic acid Directions to Hospitals Treating Clavulanic acid Risk calculators and risk factors for Clavulanic acid
|
|
Healthcare Provider Resources |
|
Causes & Risk Factors for Clavulanic acid |
|
Continuing Medical Education (CME) |
|
International |
|
|
|
Business |
|
Experimental / Informatics |
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.
- Pages with script errors
- Pages with broken file links
- Drugs with non-standard legal status
- E number from Wikidata
- ECHA InfoCard ID from Wikidata
- Chemical articles with unknown parameter in Infobox drug
- Articles without EBI source
- Chemical pages without ChemSpiderID
- Articles without KEGG source
- Articles without InChI source
- Articles without UNII source
- Articles containing unverified chemical infoboxes
- Beta-lactamase inhibitors