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Amoxicillin

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Amoxicillin
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
TradenameAmoxil, Trimox, others
Drugs.commonograph, amoxicillin
Legal AUS4
Legal CARx-only / OTC
Legal UKPOM / P
Legal USRx-only / OTC
Routes of administrationBy mouth, intravenous
Bioavailability95% (oral)
Protein bound17–20%
Metabolism< 10% hepatic
Elimination half-life61.3 minutes
ExcretionKidney (80%)

Amoxicillin is a widely used antibiotic belonging to the aminopenicillin class within the broader beta-lactam antibiotic family. It is effective against a variety of bacterial infections by inhibiting cell wall synthesis. First developed by Beecham in 1972, it is on the World Health Organization's List of Essential Medicines.

Medical uses

It is primarily prescribed for treating infections caused by susceptible Gram-positive and Gram-negative bacteria. Common indications include otitis media, streptococcal pharyngitis, pneumonia, skin infections, and urinary tract infections. It is also a key component, combined with clarithromycin and a proton-pump inhibitor, in the eradication of Helicobacter pylori for treating peptic ulcer disease. In dentistry, it is used for odontogenic infections and antibiotic prophylaxis for patients at risk of infective endocarditis, as per guidelines from the American Heart Association. It is often the first-line agent for Lyme disease in its early stages, particularly for erythema migrans.

Adverse effects

Common side effects include nausea, vomiting, rash, and antibiotic-associated diarrhea. A significant concern is the potential for hypersensitivity reactions, ranging from mild maculopapular rash to severe anaphylaxis, especially in patients with a history of penicillin allergy. Prolonged use can lead to Clostridioides difficile infection, causing severe colitis. High doses have been associated with crystalluria and interstitial nephritis. The appearance of a rash during treatment for infectious mononucleosis, often caused by the Epstein–Barr virus, is common but not typically a true allergy.

Pharmacology

As a beta-lactam antibiotic, it acts by binding to penicillin-binding proteins, thereby inhibiting the final step of peptidoglycan synthesis in the bacterial cell wall, leading to cell lysis and death. It is stable in gastric acid and is well-absorbed from the gastrointestinal tract, with absorption unaffected by food. It is distributed widely into most body tissues and fluids, including the middle ear, lungs, and prostate. It is excreted largely unchanged by the kidneys via glomerular filtration and tubular secretion; concomitant use of probenecid can delay this excretion. Its spectrum is extended when combined with clavulanic acid, marketed as Augmentin, which inhibits beta-lactamase enzymes produced by resistant bacteria like Staphylococcus aureus.

History

It was discovered by scientists at the British pharmaceutical company Beecham in 1972. Its development followed the successful introduction of ampicillin, aiming to improve oral bioavailability and spectrum. It received approval from the U.S. Food and Drug Administration and rapidly became one of the most prescribed antibiotics globally. The development of the combination with clavulanate potassium in the 1980s, pioneered by researchers at Beecham Research Laboratories, marked a significant advancement in overcoming bacterial resistance. Its inclusion on the World Health Organization's List of Essential Medicines underscores its global public health importance.

Society and culture

It is available under numerous brand names worldwide, including Amoxil and Trimox, and is often dispensed as a generic medication. Its widespread use has contributed significantly to the global issue of antimicrobial resistance, prompting initiatives like those from the Centers for Disease Control and Prevention to promote antibiotic stewardship. In many countries, it is available only by prescription, though some nations permit limited over-the-counter sale. It has been involved in several major drug recall incidents due to manufacturing concerns. The World Health Organization considers it a critical medicine for basic healthcare systems. Category:World Health Organization essential medicines Category:Penicillin antibiotics Category:Discoveries by Beecham Group