Amoxicillin/clavulanic acid
| Combination of |
| Amoxicillin |
Penicillin antibiotic |
| Clavulanic acid |
Beta-lactamase inhibitor |
| Clinical data |
| Trade names |
Augmentin |
| AHFS/Drugs.com |
monograph |
| MedlinePlus |
a685024 |
| Licence data |
US FDA:link |
| Pregnancy cat. |
B (US) |
| Legal status |
POM (UK) ℞-only (US) |
| Routes |
oral, intravenous |
| Identifiers |
| CAS number |
74469-00-4 N |
| ATC code |
J01CR02 |
| PubChem |
CID 6435923 |
| ChemSpider |
4940608 Y |
| ChEMBL |
CHEMBL1697738 N |
N (what is this?) (verify)
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Amoxicillin/clavulanic acid (INN) or co-amoxiclav (BAN) is a combination antibiotic consisting of amoxicillin trihydrate, a β-lactam antibiotic, and potassium clavulanate, a β-lactamase inhibitor. This combination results in an antibiotic with an increased spectrum of action and restored efficacy against amoxicillin-resistant bacteria that produce β-lactamase.
Unlike co-trimoxazole, the BAN has not been widely adopted internationally. Trade names include Augmentin (by GlaxoSmithKline),[1] Clavamox (by Pfizer), and many others.
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Contents
- 1 Medical uses
- 2 Adverse effects
- 3 History
- 4 Preparations
- 5 Veterinary use
- 6 Trade names
- 7 References
- 8 External links
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Medical uses
Amoxicillin/clavulanic acid is widely used to treat many infections caused by susceptible bacteria, such as urinary tract infections, respiratory tract infections, skin and soft tissue infections, and infections caused by the bacterial flora of the mouth, such as dental infections, infected animal bites, and infected human bites (including uncomplicated "clenched-fist" or "reverse-bite" injuries).[1][2]
Adverse effects
Possible side effects include diarrhea, vomiting, nausea, thrush, and a skin rash. These do not usually require medical attention. As with all antimicrobial agents, antibiotic-associated diarrhea due to Clostridium difficile ("C. diff'") infection—sometimes leading to pseudomembranous colitis—may occur during or after treatment with amoxicillin/clavulanic acid.[2]
Rarely, cholestatic jaundice (also referred to as cholestatic hepatitis, a form of liver 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 1 in 100,000 exposures.[2] In the United Kingdom, co-amoxiclav carries a warning from the Committee on Safety of Medicines to this effect.[1]
As all aminopenicillins, amoxicillin has been associated with Stevens–Johnson syndrome/toxic epidermal necrolysis, although these reactions are very rare.[2][3]
History
The combination was invented around 1977/78 by British scientists working at Beecham (now part of GlaxoSmithKline), which filed for US patent protection for the drug combination in 1979. A patent was granted in 1984.[4] Augmentin is the original name used by its inventor.
Preparations
Many branded products indicate their strengths as the quantity of amoxicillin. Augmentin 250 for example contains 250 mg of amoxicillin and 125 mg of Clavulanic acid.[1][5]
An intravenous preparation has been available in the UK since 1985,[6] but there is no parenteral preparation available in the US; the nearest equivalent is ampicillin/sulbactam.
Suspensions of amoxicillin/clavulanic acid are available for use in children. They must be refrigerated to maintain effectiveness.
Veterinary use
The amoxicillin/clavulanic acid combination is also used in the treatment of, among other infections, periodontitis and kennel cough[7][8] in dogs; urinary tract infections, skin and soft tissue infections in cats; enteritis and navel ill in calves; respiratory tract infections, soft tissue infections, metritis and mastitis in cattle; respiratory tract infections, colibacillosis, mastitis, metritis and agalactia in pigs. In combination with prednisolone it is used for intra-mammary infusion for the treatment of mastitis in lactating cows. Trade names include Clavaseptin, Clavamox and Synulox.
Amoxicillin/clavulanic acid is banned from use in domestic-food animals (cattle, swine, etc.) in both the US and Europe, in the UK synulox can be used in "domestic-food animals" as long as a specified withdrawal period is adhered to.
Bacterial resistance
Bacterial antibiotic resistance is a growing problem in veterinary medicine. Amoxicillin/clavulanic acid is reported to be effective against clinical Klebsiella infections, but is not efficacious against Pseudomonas infections.[9]
Trade names
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This is an incomplete list, which may never be able to satisfy particular standards for completeness. You can help by expanding it with reliably sourced entries.
- Amoklavin-BID (deva, Turkey)
- Amoksiklav (by Novartis Slovenia, Romania, Serbia, Bulgaria)
- Amorion Comp (by Orion Corporation Finland)
- AMOX/K CLAV (875 mg, Sandoz; US)
- Amoxi Clav (Canada)
- Amoxicilina-Clavulánico (Spain)
- Amoxicillin-clavulanate (rINN)
- Amoxicilline-clavulanique (France)
- Amoxiclav (by Teva; Belgium, Israel)
- Amoxycillin-clavulanate (US)
- AugMaxcil (Triomed; South Africa)
- Augmentin (GlaxoSmithKline originally Beecham; Hungary)
- Augpen (Zuventus; India)
- Clamoxyl Duo Oral Suspension (Australia)
- CLAMP (Dr. Reddy's, India)[10]
- Clavamox (Sandoz, Austria)
- Clavituf (Intas, india)
- Clavulin (Canada)
- Co-amoxiclav (UK, KSA, Ireland, South Africa, Iran)
- Curam (Singapore)
- Clavam (Alkem Laboratories Ltd; India)
- Enhancin (Ranbaxy, Malaysia)
- Finemox (Finecure, India)[11]
- Klamentin (CTCP Duoc Hau Giang, Vietnam)
- Klavocin (Pliva - Croatia)
- Magnabiotic (Egypt,sedico)
- MoxClav (Ranbaxy, India)
- Moxiclav Duo (Australia)
- Moxikind (Mankind Pharma; India)
- Panklav (Hemofarm - Serbia)
- Polyclav 625 (India)
- Ratio Aclavulanate 500/125 (Canada) AMC 500/125 (with potassium clavulanate)
- xcilan (ovia pharma pvt. ltd. india)
- Xiclav (GL-Pharma, Austria)
- Аугментин (Russia)
- Zakutex (South Korea)
- Alviclav 625 (Alvis Health Care, India)
References
- ^ a b c d British National Formulary (57 ed.). March 2009.
- ^ a b c d Gordon D (2010). "Amoxicillin–Clavulanic Acid (Co-Amoxiclav)". In Grayson ML et al (eds). Kucers' the Use of Antibiotics: a Clinical Review of Antibacterial, Antifungal, Antiparasitic and Antiviral Drugs. London: Hodder Arnold/ASM Press. pp. 193–4. ISBN 0-340-92767-4.
- ^ Harr T, French LE (2010). "Toxic epidermal necrolysis and Stevens-Johnson syndrome". Orphanet J Rare Dis 5: 39. doi:10.1186/1750-1172-5-39. PMC 3018455. PMID 21162721. //www.ncbi.nlm.nih.gov/pmc/articles/PMC3018455/.
- ^ US 4441609
- ^ "Augmentin -- Prescribing Information" (PDF). December 2006. http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050575s037550597s044050725s025050726s019lbl.pdf.
- ^ Davies BE, Boon R, Horton R, Reubi FC, Descoeudres CE (October 1988). "Pharmacokinetics of amoxycillin and clavulanic acid in haemodialysis patients following intravenous administration of Augmentin". Br J Clin Pharmacol 26 (4): 385–90. PMC 1386558. PMID 3190988. //www.ncbi.nlm.nih.gov/pmc/articles/PMC1386558/.
- ^ , http://www.sheltermedicine.com/portal/is_infectious_tracheobronchitis_canine.shtml[dead link]
- ^ , http://www.dogchatforum.com/kennel-cough2.htm
- ^ Federation of Veterinarians in Europe Position Paper: Antibiotic Resistance & Prudent Use of Antibiotics in Veterinary Medicine
- ^ "India Product List". Dr. Reddy's. http://www.drreddys.com/products/popups/gen_ind_productlist.html. Retrieved 2011-07-24.
- ^ "Amoxy Clav Formulations". Finecurepharmaceuticalsltd. http://www.finecurepharma.com/beta-lactamase-lnhibitors.htm. Retrieved 2012-03-27.
- http://www.merckmanuals.com/professional/print/lexicomp/amoxicillin%20and%20clavulanate%20potassium.html
External links
- Augmentin website GlaxoSmithKline
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GlaxoSmithKline plc
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| Corporate directors: |
- Chris Gent
- Andrew Witty
- Roy Anderson
- Stephanie Burns
- Stacey Cartwright
- Lawrence Culp
- Crispin Davis
- Simon Dingemans
- Judy Lewent
- Deryck Maughan
- James Murdoch
- Daniel Podolsky
- Moncef Slaoui
- Tom de Swaan
- Robert Wilson
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| Products: |
- Amoxicillin/clavulanic acid (Augmentin)
- Bupropion (Zyban)
- Paroxetine (Paxil, Seroxat, Aropax)
- Rosiglitazone (Avandia)
- Sumatriptan (Imitrex)
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Antibacterials: cell envelope antibiotics (J01C-J01D)
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| Intracellular |
- inhibit peptidoglycan subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
- DADAL/AR inhibitors (Cycloserine)
- bactoprenol inhibitors (Bacitracin)
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| Glycopeptide |
- inhibit PG chain elongation: Vancomycin# (Oritavancin
- Telavancin)
- Teicoplanin (Dalbavancin)
- Ramoplanin
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β-lactams/
(inhibit PBP
cross-links) |
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Penicillins
(penams)
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Extended sp.
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- aminopenicillins: Amoxicillin#
- Ampicillin# (Pivampicillin
- Hetacillin
- Bacampicillin
- Metampicillin
- Talampicillin)
- Epicillin
- carboxypenicillins: Carbenicillin (Carindacillin)
- Ticarcillin
- Temocillin
- ureidopenicillins: Azlocillin
- Piperacillin
- Mezlocillin
- other: Mecillinam (Pivmecillinam)
- Sulbenicillin
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Narrow sp.
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β-lactamase sensitive
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- Benzylpenicillin (G)#: Clometocillin
- Benzathine benzylpenicillin#
- Procaine benzylpenicillin#
- Azidocillin
- Penamecillin
- Phenoxymethylpenicillin (V)#: Propicillin
- Benzathine phenoxymethylpenicillin
- Pheneticillin
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β-lactamase resistant
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- Cloxacillin# (Dicloxacillin
- Flucloxacillin)
- Oxacillin
- Meticillin
- Nafcillin
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Penems
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Carbapenems
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- Biapenem
- Ertapenem
- antipseudomonal (Doripenem
- Imipenem
- Meropenem)
- Panipenem
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Cephalosporins/Cephamycins
(cephems)
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1st (PEcK)
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- Cefazolin#
- Cefacetrile
- Cefadroxil
- Cefalexin
- Cefaloglycin
- Cefalonium
- Cefaloridine
- Cefalotin
- Cefapirin
- Cefatrizine
- Cefazedone
- Cefazaflur
- Cefradine
- Cefroxadine
- Ceftezole
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2nd (HEN)
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- Cefaclor
- Cefamandole
- Cefminox
- Cefonicid
- Ceforanide
- Cefotiam
- Cefprozil
- Cefbuperazone
- Cefuroxime
- Cefuzonam
- cephamycin (Cefoxitin
- Cefotetan
- Cefmetazole)
- carbacephem (Loracarbef)
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3rd
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- Cefixime#
- Ceftriaxone#
- antipseudomonal (Ceftazidime#
- Cefoperazone)
- Cefcapene
- Cefdaloxime
- Cefdinir
- Cefditoren
- Cefetamet
- Cefmenoxime
- Cefodizime
- Cefotaxime
- Cefpimizole
- Cefpiramide
- Cefpodoxime
- Cefsulodin
- Cefteram
- Ceftibuten
- Ceftiolene
- Ceftizoxime
- oxacephem (Flomoxef
- Latamoxef ‡)
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4th (antips-)
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- Cefepime
- Cefozopran
- Cefpirome
- Cefquinome
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5th
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- Ceftobiprole
- Ceftaroline fosamil
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Veterinary
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- Ceftiofur
- Cefquinome
- Cefovecin
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Monobactams
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- Aztreonam
- Tigemonam
- Carumonam
- Nocardicin A
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β-lactamase inh.
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- penam (Sulbactam
- Tazobactam)
- clavam (Clavulanic acid)
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Combinations
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- Amoxicillin/clavulanic acid#
- Imipenem/cilastatin#
- Ampicillin/flucloxacillin
- Ampicillin/sulbactam (Sultamicillin)
- Piperacillin/tazobactam
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| Other |
- polymyxins/detergent (Colistin
- Polymyxin B)
- depolarizing (Daptomycin)
- hydrolyze NAM-NAG (Lysozyme)
- Gramicidin
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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gr+f/gr+a (t)/gr-p (c)/gr-o
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drug (J1p, w, n, m, vacc)
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