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| Combination of | |
|---|---|
| Amoxicillin | Penicillin antibiotic |
| Clavulanic acid | Beta-lactamase inhibitor |
| Clinical data | |
| Trade names | Augmentin, Clavulin, Amoclan, others[1] |
| Other names | Co-amoxiclav; Amox-clav |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a685024 |
| License data | |
| Pregnancy category |
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| Routes of administration | By mouth,intravenous[2] |
| ATC code | |
| Legal status | |
| Legal status | |
| Identifiers | |
| CAS Number | |
| PubChemCID | |
| ChemSpider | |
| KEGG | |
| ChEMBL | |
| CompTox Dashboard(EPA) | |
| Chemical and physical data | |
| Formula | C24H27KN4O10S |
| Molar mass | 602.66 g·mol−1 |
| 3D model (JSmol) | |
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 N Y (what is this?) (verify) | |
Amoxicillin/clavulanic acid, also known asco-amoxiclav oramox-clav, sold under the brand nameAugmentin, among others, is anantibiotic medication used for the treatment of a number ofbacterial infections.[5] It is a combination consisting ofamoxicillin, aβ-lactam antibiotic, andpotassium clavulanate, aβ-lactamase inhibitor.[5] It is specifically used forotitis media,streptococcal pharyngitis,pneumonia,cellulitis,urinary tract infections, andanimal bites.[5] It can be administeredorally orintravenously.[2]
Commonside effects includediarrhea, vomiting, andallergic reactions.[5] It also increases the risk ofyeast infections, headaches, andblood clotting problems.[2][6] It is not recommended in people with a history of apenicillin allergy.[2] It is relatively safe for use during pregnancy.[5]
Amoxicillin/clavulanic acid was approved for medical use in the United States in 1984.[5] It is on theWorld Health Organization's List of Essential Medicines.[7][8] The World Health Organization classifies amoxicillin/clavulanic-acid as critically important for human medicine.[9] It is available as a generic medication.[5] In 2023, it was the 66th most commonly prescribed medication in the United States, with more than 9 million prescriptions.[10][11]
Amoxicillin/clavulanic acid is widely used to treat or prevent many infections caused by susceptible bacteria, such as:
Amoxicillin/clavulanic acid is asecond-line therapy in the treatment of uncomplicatedurinary tract infections (UTIs).[14][15] It is active against UTIs caused byStaphylococcus saprophyticus,Enterococci (e.g.,Enterococcus faecalis),Escherichia coli,Klebsiella pneumoniae, andProteus mirabilis.[15] It is a definitive treatment against susceptibleextended-spectrum β-lactamase (ESBL)-producingGram-negative bacteria.[15] The drug is not effective againstPseudomonas aeruginosa,Morganella morganii, orProvidencia stuartii, nor againstAmpC β-lactamase- and ESBL-producing Gram-negative bacteria orcarbapenem-resistant Enterobacteriaceae (CRE).[15] It is not recommended in theempiric treatment of acutepyelonephritis orhospital-acquired UTIs.[15]
As determined by a 2014literature review of antibiotics for UTIs, respective early clinical cure and early bacterial cure rates were 91% and 91% fortrimethoprim/sulfamethoxazole, 92% and 87% fornitrofurantoin, 91% and 83% forfosfomycin, 90% and 91% forfluoroquinolones (ciprofloxacin andnorfloxacin), and 86% and 81% forβ-lactams (amoxicillin/clavulanic acid andcefpodoxime).[14] In a large high-qualityrandomized controlled trial of amoxicillin/clavulanic acid for UTI in 370 women, early and late clinical cure rates were 79% and 58%, respectively.[14] Amoxicillin/clavulanic acid reaches a relatively lowurine concentration, which might be involved in its lower effectiveness than other antibiotics.[15]
Amoxicillin/clavulanic acid is less effective in the treatment of UTI thanfirst-line therapies used to treat UTIs.[14][16] A 2012network meta-analysis of antibiotics for uncomplicated UTIs found that it was less effective than all other assessed agents, including trimethoprim/sulfamethoxazole, nitrofurantoin, fosfomycin, fluoroquinolones (ciprofloxacin, norfloxacin, andgatifloxacin), andpivmecillinam.[16] However, selection of an empirical antibiotic should be based on local or regional susceptibility data.[15] Additionally, selection of the most appropriate and narrowest effective antibiotic is recommended to help limit increasedantibiotic resistance tobroad-spectrum antibiotics.[15]
Combining amoxicillin/clavulanic acid withaztreonam can further enhance its activity against certain resistant UTI-causing bacteria.[15]
It is also used fortuberculosis that is resistant to other treatments.[5] The World Health Organization recommends giving amoxicillin-clavulanate along withmeropenem as one of the therapeutic options indrug-resistant tuberculosis.[17] However, across the spectrum of dosage of amoxicillin-clavulanate combination, the dose of clavulanate is constant at 125 mg, whereas the dose of amoxicillin varies at 250 mg, 500 mg and 875 mg. Thus the use of low-dose amoxicillin-clavulanate in combination with meropenem may be used in part of a treatment regimen for drug-resistant TB and this has been demonstrated in a clinical setting also. Its efficacy is attributed not to the amoxicillin component, but to the protective action of clavulanic acid over meropenem againstbeta-lactamase produced by themycobacteria. Therefore, the minimum dosage of amoxicillin (250 mg) is recommended.[18]
Possible side effects includediarrhea, vomiting,nausea,thrush, and skinrash. These do not usually require medical attention. As with all antimicrobial agents,antibiotic-associated diarrhea due toClostridioides difficile infection—sometimes leading topseudomembranous colitis—may occur during or after treatment with amoxicillin/clavulanic acid.[13]
Rarely,cholestatic jaundice (also referred to as cholestatic hepatitis, a form ofliver toxicity) has been associated with amoxicillin/clavulanic acid. The reaction may occur up to several weeks after treatment has stopped and usually takes weeks to resolve. It is more frequent in men, older people, and those who have taken long courses of treatment; the estimated overall incidence is one in 100,000 exposures.[13] In the United Kingdom, co-amoxiclav carries a warning from theCommittee on Safety of Medicines to this effect.[12]
As allaminopenicillins, amoxicillin has been associated withStevens–Johnson syndrome /toxic epidermal necrolysis, although these reactions are very rare.[13][19]
Amoxicillin is anantibiotic whileclavulanic acid is a non-antibioticβ-lactamase inhibitor which preventsmetabolism of amoxicillin by certainbacteria.
In addition to its β-lactamase inhibition, clavulanic acid showscentral nervous system actions and effects andhas been studied in the potential treatment of variouspsychiatric andneurological disorders.[20][21][22][23][24]
British scientists working atBeecham (now part ofGlaxoSmithKline) filed for patent protection for the drug combination in 1977, which was granted in 1982.[25]
It was sold under the brand name Augmentin.[12][26]
Amoxicillin/clavulanic acid is theInternational Nonproprietary Name (INN) and co-amoxiclav is theBritish Approved Name (BAN).[citation needed]
Many branded products indicate their strengths as the quantity of amoxicillin. Augmentin 250, for example, contains 250 mg of amoxicillin and 125 mg ofclavulanic acid.[12][27]
An intravenous preparation has been available in the UK since 1985,[28] but noparenteral preparation is available in the US;[citation needed] the nearest equivalent isampicillin/sulbactam.[citation needed]
Suspensions of amoxicillin/clavulanic acid are available for use in children. They must be refrigerated to maintain effectiveness.[citation needed]
Amoxicillin/clavulanic acid is used in numerous animals for a variety of conditions:
Bacterialantibiotic resistance is a growing problem inveterinary medicine. Amoxicillin/clavulanic acid is reported to be effective against clinicalKlebsiella infections, but is not efficacious againstPseudomonas infections.[30]
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