Amoxicillin/clavulanic acid

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Amoxicillin/clavulanic acid
Co-amoxiclav2DCSD.svg
Combination of
Amoxicillin Penicillin antibiotic
Clavulanic acid Beta-lactamase inhibitor
Clinical data
Trade names Augmentin, Clavamox, Tyclav
AHFS/Drugs.com monograph
MedlinePlus a685024
Licence data US FDA:link
Pregnancy cat. B1 (AU) B (US)
Legal status Prescription Only (S4) (AU) -only (CA) POM (UK) -only (US)
Routes oral, intravenous
Identifiers
CAS number 74469-00-4 N
ATC code J01CR02
PubChem CID 6435923
ChemSpider 4940608 YesY
ChEMBL CHEMBL1697738 N
 N (what is this?)  (verify)

Amoxicillin/clavulanic acid (INN) or co-amoxiclav (BAN) is an antibiotic useful for the treatment of a number of bacterial infections. It 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), Tyclav (by Beximco Pharma), and many others.

It is on the World Health Organization's List of Essential Medicines, a list of the most important medications needed in a basic health system.[2]

Medical uses[edit]

Amoxicillin/clavulanic acid is widely used to treat or prevent many infections caused by susceptible bacteria, such as:

Adverse effects[edit]

Possible side effects include diarrhea, vomiting, nausea, thrush, and skin rash. These do not usually require medical attention. As with all antimicrobial agents, antibiotic-associated diarrhea due to Clostridium difficile infection—sometimes leading to pseudomembranous colitis—may occur during or after treatment with amoxicillin/clavulanic acid.[3]

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 one in 100,000 exposures.[3] 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.[3][4]

History[edit]

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 1985.[5]

Augmentin is the original name used by its inventor.

Preparations[edit]

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][6]

An intravenous preparation has been available in the UK since 1985,[7] but no parenteral preparation is 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[edit]

Amoxicillin/clavulanic acid is used in numerous animals for a variety of conditions.

Dogs[8][9]

Cats

  • urinary tract infections
  • skin and soft tissue infections

Calves

Cattle

Pigs

In combination with prednisolone, it is used for intramammary 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 observed.

Bacterial resistance[edit]

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.[10]

Trade names[edit]

  • Axitin (Clarion medicals Limited (Nigeria)
  • Amokav (Kepler Healthcare Pvt. Ltd.,India)
  • Alviclav 625 (Alvis Health Care; India)
  • Amoclav (Rowex Ltd., Ireland)
  • Amoklavin-BID (deva, Turkey)
  • Amoksiklav (by Novartis Slovenia, 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)
  • Amoxiclavulan (by 1A Pharma; Austria)
  • Amoxycillin-clavulanate (AU)
  • AugMaxcil (Triomed; South Africa)
  • Augmentin (GlaxoSmithKline [originally Beecham]; Hungary; Pakistan, Romania, Philippines; United States, Australia, Switzerland, Czech Republic, Turkey)
  • Augpen (Zuventus; India)
  • Clamovid (Hovid)
  • Clamoxyl Duo Oral Suspension (Australia)
  • Topclav 625/375 (Indswift; India)
  • CLAMP (Dr. Reddy's, India)[11]
  • Claneksi (Sanbe Farma, Indonesia)
  • Clavamox (Sandoz, Austria)
  • Clavituf (Intas, India)
  • Clavulin (Canada, Brazil)
  • Co-amoxiclav (UK, KSA, Ireland, South Africa, Iran)[12]
  • Curam (Sandoz)
  • Curam Duo (New Zealand)
  • Clavam (Alkem Laboratories Ltd; India)
  • Enhancin (Ranbaxy, Malaysia)
  • Fleming (Medreich, India)
  • Finemox (Finecure, India)[13]
  • Forcid (Astellas)
  • Julmentin 2x (Julphar; Egypt; UAE)
  • Klamentin (CTCP Duoc Hau Giang, Vietnam)
  • Klamoks ( Bilim Pharmaceuticals, Turkey)
  • Klavocin (Pliva - Croatia)
  • Klavon ( Bilim Pharmaceuticals, Turkey)
  • Klavox (Bahrain and Oman)
  • Mega-CV (Aristo, India)
  • Magnabiotic (Egypt, Sedico)
  • MoxClav (Ranbaxy, India)
  • Moxiclav (Medochemie LTD, Cyprus)
  • Moxiclav Duo (Australia)
  • Moxikind (Mankind Pharma, India)
  • Natravox (Natrapharm, Inc., Philippines)
  • Noroclav (Norbrook, UK)
  • New-Clav (Egypt, Alandalous)
  • Panklav (Hemofarm - Serbia)
  • Optamox (Laboratorios Roemmers, Argentina)
  • Penilan DT (Portugal)
  • Polyclav 625 (India)
  • Sinergia (LIFE, Ecuador)
  • Ratio Aclavulanate 500/125 (Canada)
  • xcilan (ovia pharma pvt. ltd. India)
  • Xiclav (GL-Pharma, Austria)
  • Аугментин (Russia)
  • Zakutex (South Korea)
  • Klavox (Kingdom of Saudi Arabia)
  • Penom Clav 625 (India)

References[edit]

  1. ^ a b c d British National Formulary (57 ed.). March 2009. 
  2. ^ "WHO Model List of EssentialMedicines". World Health Organization. October 2013. Retrieved 22 April 2014. 
  3. ^ 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. 
  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. 
  5. ^ US 4441609 
  6. ^ "Augmentin -- Prescribing Information" (PDF). December 2006. 
  7. ^ 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. doi:10.1111/j.1365-2125.1988.tb03395.x. PMC 1386558. PMID 3190988. 
  8. ^ "Canine Infectious Tracheobronchitis (Kennel Cough)". Archived from the original on 2006-05-21. Retrieved 2013-05-30. 
  9. ^ "Kennel Cough - Symptoms and Treatment". Retrieved 2013-05-30. 
  10. ^ Federation of Veterinarians in Europe Position Paper: Antibiotic Resistance & Prudent Use of Antibiotics in Veterinary Medicine
  11. ^ "India Product List". Dr. Reddy's. Retrieved 2011-07-24. 
  12. ^ "Gererics Product List C-E". Almus. Retrieved 2014-02-06. 
  13. ^ "Amoxy Clav Formulations". Finecurepharmaceuticalsltd. Retrieved 2012-03-27. 

External links[edit]