Amoxicillin

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Amoxicillin
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Systematic (IUPAC) name
(2S,5R,6R)-6-{[(2R)-2-amino-2-(4-hydroxyphenyl)-acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Clinical data
Trade names Actimoxi, Alphamox, Amocla,Tycil, Amoxil, Trimox, among others
AHFS/Drugs.com Template:Drugs.com
MedlinePlus a685001
Pregnancy cat. A (AU)Template:SpB (US)Template:Sp
Legal status POMTemplate:Sp(UK)Template:Sp-onlyTemplate:Sp(US)Template:Sp
Routes Oral, intravenous
Pharmacokinetic data
Bioavailability 95% oral
Metabolism less than 30% biotransformed in liver
Half-life 61.3 minutes
Excretion renal
Identifiers
CAS number 26787-78-0Template:Cascite
ATC code J01CA04 Template:ATCvet
PubChem CID 33613
DrugBank DB01060
ChemSpider 31006Template:Chemspidercite
UNII 9EM05410Q9Template:Fdacite
KEGG D07452Template:Keggcite
ChEBI CHEBI:2676 Template:Tick
ChEMBL CHEMBL1082 Template:Tick
Chemical data
Formula Template:OrganicBox atomTemplate:OrganicBox atomTemplate:OrganicBox atomTemplate:OrganicBox atomTemplate:OrganicBox atom 
Mol. mass 365.4 g/mol
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Template:Main other

Amoxicillin BP

Amoxicillin (INN), formerly amoxycillin (BAN), and abbreviated amox, is a moderate-spectrum, bacteriolytic, β-lactam antibiotic in the aminopenicillin family used to treat bacterial infections caused by susceptible microorganisms. It is usually the drug of choice within the class because it is better-absorbed, following oral administration, than other β-lactam antibiotics. Amoxicillin is one of the most common antibiotics prescribed for children. The drug first became available in 1972.

Amoxicillin is susceptible to degradation by β-lactamase-producing bacteria, which are resistant to a narrow spectrum of β-lactam antibiotics, such as penicillin. For this reason, it is often combined with clavulanic acid, a β-lactamase inhibitor. This increases effectiveness by reducing its susceptibility to β-lactamase resistance.[1]

Medical uses

Amoxicillin is used in the treatment of a number of infections, including acute otitis media, streptococcal pharyngitis, pneumonia, skin infections, urinary tract infections, Salmonella infections, Lyme disease, and chlamydia infections.[2] It is also used to prevent bacterial endocarditis in high-risk people having dental work done, to prevent Streptococcus pneumoniae and other encapsulated bacterial infections in those without spleens, such as people with sickle-cell disease, and for both the prevention and the treatment of anthrax.[2] The United Kingdom recommends against its use for infectious endocarditis prophylaxis.[3] These recommendations have not appeared to have changed the rates of infection.[4]

Amoxicillin and amoxicillin-clavulanate are recommended by guidelines as the first-choice drug for bacterial sinusitis, but most sinusitis is caused by viruses, for which amoxicillin and amoxicillin-clavulanate are ineffective.[5][6] Amoxicillin is occasionally used for the treatment of skin infections, such as acne vulgaris.[7] It is often an effective treatment for cases of acne vulgaris that have responded poorly to other antibiotics, such as doxycycline and minocycline.[8]

Adverse effects

Side-effects are similar to those for other beta-lactam antibiotics, including nausea, vomiting, rashes, and antibiotic-associated colitis. Loose bowel movements (diarrhea) may also occur. Rarer side-effects include mental changes, lightheadedness, insomnia, confusion, anxiety, sensitivity to lights and sounds, and unclear thinking. Immediate medical care is required upon the first signs of these side-effects.

The onset of an allergic reaction to amoxicillin can be very sudden and intense; emergency medical attention must be sought as quickly as possible. The initial phase of such a reaction often starts with a change in mental state, skin rash with intense itching (often beginning in fingertips and around groin area and rapidly spreading), and sensations of fever, nausea, and vomiting. Any other symptoms that seem even remotely suspicious must be taken very seriously. However, more mild allergy symptoms, such as a rash, can occur at any time during treatment, even up to a week after treatment has ceased. For some people allergic to amoxicillin, the side-effects can be deadly.

Use of the amoxicillin/clavulanic acid combination for more than one week has caused mild hepatitis in some patients. Young children having ingested acute overdoses of amoxicillin-manifested lethargy, vomiting, and renal dysfunction.[9][10]

Nonallergic amoxicillin rash

Between 3 and 10% of children taking amoxicillin (or ampicillin) show a late-developing (>72 hours after beginning medication and having never taken penicillin-like medication previously) rash, which is sometimes referred to as the "amoxicillin rash". The rash can also occur in adults.

The rash is described as maculopapular or morbilliform (measles-like; therefore, in medical literature, it is called "amoxicillin-induced morbilliform rash".[11]) It starts on the trunk and can spread from there. This rash is unlikely to be a true allergic reaction, and is not a contraindication for future amoxicillin usage, nor should the current regimen necessarily be stopped. However, this common amoxicillin rash and a dangerous allergic reaction cannot easily be distinguished by inexperienced persons, so a healthcare professional is often required to distinguish between the two.[12][13]

A nonallergic amoxicillin rash may also be an indicator of infectious mononucleosis. Some studies indicate about 80-90% of patients with acute Epstein Barr virus infection treated with amoxicillin or ampicillin develop such a rash.[14]

Interaction

Amoxicillin may interact with these drugs:

Mechanism of action

{{#invoke:main|main}} This drug acts by inhibiting the synthesis of bacterial cell walls. It inhibits cross-linkage between the linear peptidoglycan polymer chains that make up a major component of the cell walls of both Gram-positive and Gram-negative bacteria.

It has two ionizable groups in the physiological range (the amino group in alpha-position to the amide carbonyl group and the carboxyl group).

Spectrum of microorganism susceptibility and resistance

In general, Streptococcus, Bacillus subtilis, Enterococcus, Haemophilus, Helicobacter, and Moraxella are susceptible to amoxicillin, whereas Citrobacter, Klebsiella and Pseudomonas aeruginosa are resistant to it.[16] Some E. coli and most clinical isolates of Staphylococcus aureus have developed resistance to amoxicillin to varying degrees.

History

{{#invoke:see also|seealso}} Amoxicillin was one of several semisynthetic derivatives of 6-aminopenicillanic acid (6-APA) developed at Beecham in the 1960s. It became available in 1972, and was the second aminopenicillin to reach the market (after ampicillin in 1961).[17][18] Co-amoxiclav became available in 1981.[17]

Formulations

Modes of delivery

Pharmaceutical manufacturers make amoxicillin in trihydrate form, available as capsules, chewable and dispersible tablets, syrup and pediatric suspension for oral use, and as the sodium salt for intravenous administration.

Amoxicillin is most commonly taken orally. The liquid forms are helpful where the patient might find it difficult to take tablets or capsules.

Research with mice indicated successful delivery using intraperitoneally injected amoxicillin-bearing microparticles.[19]

Brand names

Novamoxin prescription drug—500mg Amoxicillin trihydrate

Amoxicillin is one of the semisynthetic penicillins discovered by Beecham scientists. The patent for amoxicillin has expired, thus amoxicillin and co-amoxiclav preparations are marketed under many trade names and/or have several synonyms across the world, such as:

  • Actimoxi[20]
  • Alphamox
  • Amimox
  • Amocla
  • AMK
  • Amoksiklav
  • Amorion
  • Amoxibos
  • Amoxiclav
  • Amoxidal
  • Amoxil
  • Amoxin
  • Amoxibiotic[21]
  • Amoxicilina
  • Amoxidal
  • Apo-Amoxi
  • Arsogil[22]
  • Augmentin
  • Bactox
  • Bioxidona[23]
  • Cilamox
  • Clamoxyl
  • Clavamox
  • Clonamox
  • Curam
  • Dedoxil
  • Dispermox
  • Duomox
  • Defender[24]
  • E-Mox[25]
  • Enhancin
  • Ezymox[26]
  • Gimalxina
  • Geramox
  • Hiconcil
  • Isimoxin[27]
  • Klavax
  • Klavocin
  • Klavox
  • Lamoxy
  • Largopen
  • MOX
  • Moxatag
  • Moxilen
  • Moxypen
  • Moxyvit
  • Nobactam
  • Novamoxin
  • Optamox
  • Ospamox
  • Pamoxicillin
  • Panklav
  • Polymox
  • Senox [28]
  • Sinacilin
  • Skymox[29]
  • Spektramox
  • Starmox[30]
  • Trimox
  • Tolodina[31]
  • Tormoxin
  • Tyclav[32]
  • Unimox
  • Wedemox
  • Wymox
  • Yucla
  • Zerrsox
  • Zimox
  • Zoxicillin[33]

Names without individual reference are referenced at.[34]

References

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  10. {{#invoke:citation/CS1|citation |CitationClass=book }}
  11. Template:Cite web
  12. {{#invoke:Citation/CS1|citation |CitationClass=journal }}
  13. {{#invoke:citation/CS1|citation |CitationClass=book }}
  14. {{#invoke:Citation/CS1|citation |CitationClass=journal }}
  15. British National Formulary 57 March 2009
  16. Template:Cite web
  17. 17.0 17.1 {{#invoke:citation/CS1|citation |CitationClass=book }}
  18. {{#invoke:citation/CS1|citation |CitationClass=book }}
  19. {{#invoke:Citation/CS1|citation |CitationClass=journal }}
  20. Catalog.md: Actimoxi Linked 2013-12-09
  21. Catalog.md: Amoxibiotic Linked 2013-12-09
  22. Aversi (Georgia): Arsogil Linked 2013-12-09
  23. Catalog.md: Bioxidona Linked 2013-12-09
  24. DrugsUpdate India: Defender from Sac Pharma Linked 2013-12-09
  25. Eipico (Egypt): E-Mox Linked 2013-12-09
  26. DrugsUpdate India: Ezymox from Sac Pharma Linked 2013-12-09
  27. Catalog.md: Isimoxin Linked 2013-12-09
  28. BioPortal: Senox Linked 2013-12-09
  29. PalMediNet: Skymox Linked 2013-12-09
  30. Sarthak Biotech India: Starmox Linked 2013-12-09
  31. Catalog.md: Tolodina Linked 2013-12-09
  32. Beximco Pharma, Bangladesh: Tyclav Linked 2013-12-09
  33. PakMediNet (Pakistan): Zoxicillin Linked 2013-12-09
  34. Drugs.com: Amoxicillin Linked 2013-12-09

Further reading

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External links

Template:PenicillinAntiBiotics Template:GlaxoSmithKline