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Amoxicillin is an antibiotic often used for the treatment of a number of bacterial infections.
Common adverse effects include nausea and rash.
Amoxicillin was discovered in 1958 and came into medical use in 1972.
Contents
1 Medical uses
1.1 Acute otitis media
1.2 Respiratory infections
1.3 H. pylori
1.4 Lyme borreliosis
1.5 Skin infections
1.6 Infections in infants in resource-limited settings
1.7 Prevention of bacterial endocarditis
1.8 Combination treatment
1.9 Spectrum of activity
2 Adverse effects
2.1 Nonallergic rash
3 Interactions
4 Pharmacology
5 History
6 Society and culture
6.1 Modes of delivery
6.2 Names
7 References
8 Further reading
9 External links
Medical uses
Amoxicillin BP
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.
Acute otitis media
Children with acute otitis media who are younger than 6 months of age are generally treated with amoxicillin or other antibiotic. Although most children with acute otitis media who are older than two years old do not benefit from treatment with amoxicillin or other antibiotic, such treatment may be helpful in children younger than two years old with acute otitis media that is bilateral or accompanied by ear drainage.
Respiratory infections
Amoxicillin and amoxicillin-clavulanate have been recommended by guidelines as the drug of choice for bacterial sinusitis and other respiratory infections.
Amoxicillin is recommended as the preferred first-line treatment for community-acquired pneumonia in adults by the National Institute for Health and Care Excellence, either alone (mild to moderate severity disease) or in combination with a macrolide.
H. pylori
It is effective as one part of a multi-drug regimen for treatment of stomach infections of Helicobacter pylori. It is typically combined with a proton-pump inhibitor (such as omeprazole ) and a macrolide antibiotic (such as clarithromycin ); other drug combinations are also effective.
Lyme borreliosis
Amoxicillin is effective for treatment of early cutaneous Lyme borreliosis ; the effectiveness and safety of oral amoxicillin is neither better nor worse than common alternatively-used antibiotics.
Skin infections
Amoxicillin is occasionally used for the treatment of skin infections,
Infections in infants in resource-limited settings
Amoxicillin is recommended by the World Health Organization for the treatment of infants with signs and symptoms of pneumonia in resource-limited situations when the parents are unable or unwilling to accept hospitalization of the child. Amoxicillin in combination with gentamicin is recommended for the treatment of infants with signs of other severe infections when hospitalization is not an option.
Prevention of bacterial endocarditis
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.
Combination treatment
Amoxicillin is susceptible to degradation by β-lactamase -producing bacteria, which are resistant to most β-lactam antibiotics, such as penicillin. For this reason, it may be combined with clavulanic acid, a β-lactamase inhibitor. This drug combination is commonly called co-amoxiclav.
Spectrum of activity
It is a moderate-spectrum, bacteriolytic, β-lactam antibiotic in the aminopenicillin family used to treat susceptible Gram-positive and Gram-negative bacteria. It is usually the drug of choice within the class because it is better-absorbed, following oral administration, than other β-lactam antibiotics.
In general, Streptococcus, Bacillus subtilis, Enterococcus, Haemophilus, Helicobacter, and Moraxella are susceptible to amoxicillin, whereas Citrobacter, Klebsiella and Pseudomonas aeruginosa are resistant to it. Some E. coli and most clinical strains of Staphylococcus aureus have developed resistance to amoxicillin to varying degrees.
Adverse effects
Adverse effects are similar to those for other β-lactam antibiotics, including nausea, vomiting, rashes, and antibiotic-associated colitis. Loose bowel movements (diarrhea) may also occur. Rarer adverse 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 adverse 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 adverse effects can be fatal due to anaphylaxis.
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.
There is poor reporting of adverse effects of amoxicillin from clinical trials. For this reason, the severity and frequency of adverse effects from amoxicillin is probably higher than reported from clinical trials.
Nonallergic 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”.
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.
Nonallergic amoxicillin rash eight days after first dose: This photo was taken 24 hours after the rash began.
Eight hours after the first photo, individual spots have grown and begun to merge.
At 23 hours after the first photo, the color appears to be fading, and much of rash has spread to confluence.
Interactions
Amoxicillin may interact with these drugs:
Anticoagulants ( dabigatran, warfarin ).
Cancer treatment ( methotrexate ).
Uricosuric drugs.
Typhoid vaccine
Probenecid reduces renal excretion and increases the blood levels of amoxicillin.
Oral contraceptives may become less effective.
Allopurinol (gout treatment).
Endocarditis prevention.
Pharmacology
Amoxicillin (α-amino-p-hydroxybenzyl penicillin) is a semisynthetic derivative of penicillin with a structure similar to ampicillin but with better absorption when taken by mouth, thus yielding higher concentrations in blood and in urine.
Amoxicillin attaches to the cell wall of susceptible bacteria and results in their death. It also is a bactericidal compound. It is effective against streptococci, pneumococci, enterococci, Haemophilus influenzae, Escherichia coli, Proteus mirabilis, Neisseria meningitidis, Neisseria gonorrhoeae, Shigella, Chlamydia trachomatis, Salmonella, Borrelia burgdorferi, and Helicobacter pylori. It inhibits cross-linkage between the linear peptidoglycan polymer chains that make up a major component of the bacterial cell wall.
It has two ionizable groups in the physiological range (the amino group in alpha-position to the amide carbonyl group and the carboxyl group).
History
See also: Timeline of antibiotics
Amoxicillin was one of several semisynthetic derivatives of 6-aminopenicillanic acid ( 6-APA ) developed at Beecham, England in the 1960s. It became available in 1972 and was the second aminopenicillin to reach the market (after ampicillin in 1961).
Society and culture
Modes of delivery
Pharmaceutical manufacturers make amoxicillin in tri hydrate form, for oral use available as capsules, regular, 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.
The intravenous form of amoxicillin is not sold in the USA.
Research with mice indicated successful delivery using intraperitoneally injected amoxicillin-bearing microparticles.
Names
“Amoxicillin” is the INN, BAN, and USAN, while “amoxycillin” is the AAN.
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 various trade names across the world.

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