Amoxicillin is an antibiotic medication belonging to the aminopenicillin class of the penicillin family. The drug is used to treat bacterial infections such as middle ear infection, strep throat, pneumonia, skin infections, odontogenic infections, and urinary tract infections. It is taken orally (swallowed by mouth), or less commonly by either intramuscular injection or by an IV bolus injection, which is a relatively quick intravenous injection lasting from a couple of seconds to a few minutes.[8][9]
Common adverse effects include nausea and rash.[8] It may also increase the risk of yeast infections, and when used in combination with clavulanic acid, diarrhea.[10] It should not be used in those who are allergic to penicillin.[8] While usable in those with kidney problems, the dose may need to be decreased.[8] Its use in pregnancy and breastfeeding does not appear to be harmful.[8] Amoxicillin is in the β-lactam family of antibiotics.[8]
Amoxicillin was discovered in 1958 and came into medical use in 1972.[11][12] Amoxil was approved for medical use in the United States in 1974,[3][4] and in the United Kingdom in 1977.[1] It is on the World Health Organization's List of Essential Medicines.[13] It is one of the most commonly prescribed antibiotics in children.[14] Amoxicillin is available as a generic medication.[8] In 2023, it was the 23rd most commonly prescribed medication in the United States, with more than 23million prescriptions.
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.[8][17]
Acute otitis media
Children with acute otitis media who are younger than six months of age are generally treated with amoxicillin or other antibiotics. Although most children with acute otitis media who are older than two years old do not benefit from treatment with amoxicillin or other antibiotics, such treatment may be helpful in children younger than two years old with acute otitis media that is bilateral or accompanied by ear drainage.[18] In the past, amoxicillin was dosed three times daily when used to treat acute otitis media, which resulted in missed doses in routine ambulatory practice. There is now evidence that two-times daily dosing or once-daily dosing has similar effectiveness.
Adverse effects
Adverse effects are similar to those for other β-lactam antibiotics, including nausea, vomiting, rashes, and antibiotic-associated colitis. Diarrhea (loose bowel movements) may also occur.
Rarer adverse effects include mental and behavioral changes, lightheadedness, insomnia, hyperactivity, agitation, confusion, anxiety, sensitivity to lights and sounds, and unclear thinking.[2][41][42] Immediate medical care is required upon the first signs of these adverse effects.[8] Similarly to other penicillins, amoxicillin has been associated with an increased risk of seizures.[2]
Interactions
Amoxicillin may interact with these drugs:
When given intravenously or intramuscularly:[9]
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.[58] Amoxicillin diffuses easily into tissues and body fluids. It will cross the placenta and is excreted into breastmilk in small quantities. It is metabolized by the liver and excreted into the urine. It has an onset of 30 minutes and a half-life of 3.7 hours in newborns and 1.4 hours in adults.[17]
Amoxicillin attaches to the cell wall of susceptible bacteria and results in their death. 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.[17] As a derivative of ampicillin, amoxicillin is a member of the penicillin family and, like penicillins, is a
Chemistry
Amoxicillin is a β-lactam and aminopenicillin antibiotic in terms of chemical structure.[61] It is structurally related to ampicillin.[61]
The experimental log P of amoxicillin is 0.87.[62][63] It is described as an "ambiphilic"—between hydrophilic and lipophilic—antibiotic.[64]
History
Amoxicillin was one of several semisynthetic derivatives of 6-aminopenicillanic acid (6-APA) developed by the Beecham Group in the 1960s. It was invented by Anthony Alfred Walter Long and John Herbert Charles Nayler, two British scientists.[65][66] It became available in 1972 and was the second aminopenicillin to reach the market (after ampicillin in 1961).[67][68][69] Co-amoxiclav became available in 1981.[68]
Society and culture
Economics
Amoxicillin is relatively inexpensive.[70] In 2022, a survey of eight generic antibiotics commonly prescribed in the United States found their average cost to be about $42.67, while amoxicillin was sold for $12.14 on average.[71]
Modes of delivery
Pharmaceutical manufacturers make amoxicillin in trihydrate 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.
Veterinary uses
Amoxicillin is also sometimes used as an antibiotic for animals. The use of amoxicillin for animals intended for human consumption (chickens, cattle, and swine for example) has been approved.[79]
Further reading
External links
References
- Amoxil Vials for Injection 500mg - Summary of Product Characteristics (SmPC) (emc), 4 November 2021, retrieved 8 October 2022^
- Amoxil (amoxicillin) Capsules, Tablets, Chewable Tablets, and Powder for Oral Suspension DailyMed, retrieved 8 October 2022^
- Amoxil: FDA-Approved Drugs