Amoxicillin

WorldBrand briefing

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Original synthesis to sit alongside the encyclopedia article below. Not part of Wikipedia; verify facts on Wikipedia when precision matters.

Amoxicillin is a widely used semi-synthetic beta-lactam antibiotic in the penicillin family, used to treat a range of bacterial infections including respiratory tract, ear, skin, and urinary tract infections. It works by blocking the synthesis of bacterial cell walls to eliminate susceptible bacteria.

Key moments

  • 1960sDeveloped by British researchers at Beecham Group as a semi-synthetic penicillin derivative
  • 1972First approved and marketed for medical use globally
  • Late 20th centuryBecame one of the most commonly prescribed antibiotics worldwide
  • 2020s (ongoing)Remains a core essential medicine per WHO, with growing focus on addressing antibiotic resistance from overuse

Global Healthcare Role

Amoxicillin is a foundational medication in global public health, included on the World Health Organization's List of Essential Medicines. Its oral bioavailability makes it ideal for outpatient treatment, especially for pediatric patients, who are among the most frequent users of the drug.

Resistance and Stewardship

Over decades of widespread use, amoxicillin has become a prominent example of antibiotic resistance, with many bacterial strains now developing reduced susceptibility. This has spurred global efforts to promote prudent antibiotic prescribing and infection prevention to preserve the drug's long-term effectiveness.

Brand and Generic Landscape

Though originally sold under several brand names including Amoxil and Augmentin (when combined with clavulanic acid to block bacterial beta-lactamase enzymes), amoxicillin is now predominantly available as an affordable generic, expanding access to the drug for low-income and middle-income communities through global health initiatives.

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.[15][16]

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.[19]

Respiratory infections

Most sinusitis infections are caused by viruses, for which amoxicillin and amoxicillin-clavulanate are ineffective,[20] and the small benefit gained by amoxicillin may be overridden by the adverse effects.[21] Amoxicillin is considered the first-line empirical treatment for most cases of uncomplicated bacterial sinusitis in children and adults when culture data is unavailable.[22][23][24] 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.[25] Research suggests that is as effective as co-amoxiclav (a broad-spectrum antibiotic) for people admitted to hospital with pneumonia, regardless of its severity.[26][27] The World Health Organization (WHO) recommends amoxicillin as first-line treatment for pneumonia that is not "severe".[28] Amoxicillin is used in post-exposure inhalation of anthrax to prevent disease progression and for prophylaxis.[17]

H. pylori

It is effective as one part of a multi-drug regimen for the 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.[29] One old article suggests using amoxicillin with bismuth subsalicylate (pepto bismol) which does work.[30]

Lyme borreliosis

Amoxicillin is effective for the treatment of early cutaneous Lyme borreliosis; the effectiveness and safety of oral amoxicillin is neither better nor worse than common alternatively-used antibiotics.[31]

Odontogenic infections

Amoxicillin is used to treat odontogenic infections, infections of the tongue, lips, and other oral tissues. It may be prescribed following a tooth extraction, particularly in those with compromised immune systems.[32]

Skin infections

Amoxicillin is occasionally used for the treatment of skin infections,[17] such as acne vulgaris.[33] It is often an effective treatment for cases of acne vulgaris that have responded poorly to other antibiotics, such as doxycycline and minocycline.[34]

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.[35]

Prevention of bacterial endocarditis

It is also used to prevent bacterial endocarditis and as a pain-reliever in high-risk people having dental work done, to prevent Streptococcus pneumoniae and other encapsulated bacterial infections in those without spleens, people with damaged spleens (such as some with sickle-cell disease), and for both the prevention and the treatment of anthrax.[8] The United Kingdom recommends against its use for infectious endocarditis prophylaxis.[36] These recommendations do not appear to have changed the rates of infection for infectious endocarditis.[37]

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.[38]

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.[39] Some E. coli and most clinical strains of Staphylococcus aureus have developed resistance to amoxicillin to varying degrees.[40]

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][41][43][44] Amoxicillin-induced neurotoxicity has been especially associated with concentrations of greater than 110mg/L.[45]

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; a skin rash with intense itching (often beginning in the fingertips and around the 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.[8]

Use of the amoxicillin/clavulanic acid combination for more than one week has caused a drug-induced immunoallergic-type hepatitis in some patients. Young children having ingested acute overdoses of amoxicillin manifested lethargy, vomiting, and renal dysfunction.[46][47]

There is poor reporting of adverse effects of amoxicillin from clinical trials. For this reason, the severity and frequency of adverse effects from amoxicillin are probably higher than reported in clinical trials.[10]

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 and may rarely be a component of the DRESS syndrome.[48]

The rash is described as maculopapular or morbilliform (measles-like; therefore, in medical literature, it is called "amoxicillin-induced morbilliform rash".[49]). 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.[50][51]

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.[52]

Interactions

Amoxicillin may interact with these drugs:

When given intravenously or intramuscularly:[9]

  • Anticoagulants (dabigatran, warfarin).[17][53][54]
  • Methotrexate (chemotherapy and immunosuppressant).[54]
  • Typhoid, Cholera and BCG vaccines.[55][54]
  • Probenecid reduces renal excretion and increases blood levels of amoxicillin.[55][54]
  • Oral contraceptives potentially become less effective.[56]
  • Allopurinol (gout treatment).[55][54][57]
  • Mycophenolate (immunosuppressant)[54]
  • It should not be mixed with blood products, or proteinaceous fluids (including protein hydrolysates) or with intravenous lipid emulsions
  • aminoglycoside should be injected at a separate site from amoxicillin if the patient is prescribed both medications at the same time. Neither drug should be mixed in a syringe. Neither should they be mixed in an intravenous fluid container or giving set because of loss of activity of the aminoglycoside under these conditions.
  • ciprofloxacin should not be mixed with amoxicillin.
  • Infusions containing dextran or bicarbonate should not be mixed with amoxicillin solutions.

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 β-lactam antibiotic.[59] 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).[60]

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.

An extended-release is available.[5][72] The intravenous form of amoxicillin is not sold in the United States.[73] When an intravenous aminopenicillin is required in the United States, ampicillin is typically used. When there is an adequate response to ampicillin, the course of antibiotic therapy may often be completed with oral amoxicillin.[74]

Research with mice indicated successful delivery using intraperitoneally injected amoxicillin-bearing microparticles.[75]

Names

Amoxicillin is the international nonproprietary name (INN),[76] British Approved Name (BAN), Australian Approved Name (AAN), and United States Adopted Name (USAN), while amoxycillin is the former AAN.[77]

Amoxicillin is one of the semisynthetic penicillins discovered by the former pharmaceutical company Beecham Group. The patent for amoxicillin has expired, thus amoxicillin and co-amoxiclav preparations are marketed under various brand names across the world.[78]

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

References

  1. Amoxil Vials for Injection 500mg - Summary of Product Characteristics (SmPC) (emc), 4 November 2021, retrieved 8 October 2022^
  2. Amoxil (amoxicillin) Capsules, Tablets, Chewable Tablets, and Powder for Oral Suspension DailyMed, retrieved 8 October 2022^
  3. Amoxil: FDA-Approved Drugs U.S. Food and Drug Administration (FDA), retrieved 8 October 2022^
  4. Trimox: FDA-Approved Drugs U.S. Food and Drug Administration (FDA), retrieved 8 October 2022^
  5. Moxatag (amoxicillin extended-release) Tablets Initial U.S. Approval: 1974 DailyMed, retrieved 8 October 2022^
  6. Amoxicillin: Uses, Interactions, Mechanism of Action DrugBank Online, 18 January 1974, retrieved 5 November 2024^
  7. Amoxicillin www.chemsrc.com, retrieved 8 May 2018^
  8. Amoxicillin Drugs.com, The American Society of Health-System Pharmacists, 3 January 2022, retrieved 24 November 2022^
  9. Amoxicillin Sodium for Injection EMC, 10 February 2016, retrieved 26 October 2016^
  10. Common harms from amoxicillin: a systematic review and meta-analysis of randomized placebo-controlled trials for any indication CMAJ, January 2016^
  11. Analogue-based Drug Discovery John Wiley & Sons, 2006^
  12. An introduction to pharmaceutical sciences production, chemistry, techniques and technology Woodhead Pub., 2012^
  13. The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023) World Health Organization, 2023^
  14. Diseases of the liver and biliary system in children Wiley-Blackwell, 2008^
  15. Top 300 of 2023 ClinCalc, retrieved 12 August 2025^
  16. Amoxicillin Drug Usage Statistics, United States, 2014 - 2023 ClinCalc, retrieved 12 August 2025^
  17. Amoxicillin Davis, 2017, retrieved 22 March 2017^
  18. Antibiotics for acute otitis media in children The Cochrane Database of Systematic Reviews, November 2023^
  19. Once or twice daily versus three times daily amoxicillin with or without clavulanate for the treatment of acute otitis media The Cochrane Database of Systematic Reviews, December 2013^
  20. Five Things Physicians and Patients Should Question Choosing Wisely: An Initiative of the ABIM Foundation, American Academy of Allergy, Asthma, and Immunology, retrieved 14 August 2012^
  21. Antibiotics for acute maxillary sinusitis in adults The Cochrane Database of Systematic Reviews, February 2014^
  22. Uncomplicated acute sinusitis and rhinosinusitis in adults: Treatment UpToDate, retrieved 13 November 2023^
  23. ^
  24. ^
  25. Pneumonia: Diagnosis and Management of Community– and Hospital-Acquired Pneumonia in Adults National Institute for Health and Care Excellence (UK), 2014^
  26. No evidence of difference in mortality with amoxicillin versus co-amoxiclav for hospital treatment of community-acquired pneumonia The Journal of Infection, June 2024^
  27. Amoxicillin is effective for many people hospitalised with pneumonia NIHR Evidence, 22 November 2024^
  28. Revised WHO Classification and Treatment of Pneumonia in Children at Health Facilities - NCBI Bookshelf World Health Organization, 2014^
  29. ACG Clinical Guideline: Treatment of Helicobacter pylori Infection The American Journal of Gastroenterology, February 2017^
  30. Efficacy and Tolerability of Two Quadruple Regimens: Bismuth, Omeprazole, Metronidazole with Amoxicillin or Tetracycline as First-Line Treatment for Eradication of Helicobacter Pylori in Patients with Duodenal Ulcer: A Randomized Clinical Trial PLOS ONE, 2018^
  31. Efficacy and Safety of Antibiotic Therapy in Early Cutaneous Lyme Borreliosis: A Network Meta-analysis JAMA Dermatology, November 2018^
  32. Amoxicillin/Clavulanic Acid for the Treatment of Odontogenic Infections: A Randomised Study Comparing Efficacy and Tolerability versus Clindamycin International Journal of Dentistry, 2015^
  33. Adolescent Acne: Management^
  34. Amoxicillin and Acne Vulgaris scienceofacne.com, 5 September 2012, retrieved 17 August 2012^
  35. Guideline: Managing Possible Serious Bacterial Infection in Young Infants When Referral Is Not Feasible - NCBI Bookshelf World Health Organization, 2015^
  36. CG64 Prophylaxis against infective endocarditis: Full guidance NICE, retrieved 8 June 2011^
  37. Impact of the NICE guideline recommending cessation of antibiotic prophylaxis for prevention of infective endocarditis: before and after study BMJ, May 2011^
  38. Amoxicillin Susceptibility and Resistance Data retrieved 20 July 2013^
  39. Amoxicillin spectrum of bacterial susceptibility and Resistance retrieved 8 April 2012^
  40. Antimicrobial resistance in Africa: a systematic review BMC Infectious Diseases, September 2017^
  41. Complications associated with antibiotic administration: neurological adverse events and interference with antiepileptic drugs Int J Antimicrob Agents, July 2017^
  42. Evidence for interplay among antibacterial-induced gut microbiota disturbance, neuro-inflammation, and anxiety in mice Mucosal Immunol, September 2018^
  43. Catching the seizure culprit: drugs on the differential Orthopedics, September 2010^
  44. Evidence for neurotoxicity associated with amoxicillin in juvenile rats Hum Exp Toxicol, August 2016^
  45. Amoxicillin-Induced Neurotoxicity: Contribution of a Healthcare Data Warehouse to the Determination of a Toxic Concentration Threshold Antibiotics, March 2023^
  46. Amoxicillin-clavulanic acid-induced hepatitis American Journal of Otolaryngology, January 2007^
  47. Disposition of Toxic Drugs and Chemicals in Man Biomedical Publications, 2008^
  48. Amoxicillin Rash Tufts Medical Center, Tufts Medicine MelroseWakefield Hospital, retrieved 24 June 2023^
  49. Role of delayed cellular hypersensitivity and adhesion molecules in amoxicillin-induced morbilliform rashes Archives of Dermatology, April 1997^
  50. A review of evidence supporting the American Academy of Pediatrics recommendation for prescribing cephalosporin antibiotics for penicillin-allergic patients Pediatrics, April 2005^
  51. Your child's health: the parents' one-stop reference guide to symptoms, emergencies, common illnesses, behavior problems, healthy development Bantam Books, 2005^
  52. Ampicillin rash The Western Journal of Medicine, April 1977^
  53. British National Formulary 57 March 2009^
  54. Pharmacology in Clinical Neurosciences: A Quick Guide Springer, 2020^
  55. Pharmacotherapeutics for Advanced Practice: A Practical Approach LWW, 17 August 2016^
  56. Antibiotic and oral contraceptive drug interactions: Is there a need for concern? The Canadian Journal of Infectious Diseases, November 1999^
  57. Textbook of Family Medicine W.B. Saunders, January 2012^
  58. Amoxicillin, a new penicillin antibiotic Antimicrobial Agents and Chemotherapy, February 1973^
  59. Microbes and Society: An Introduction to Microbiology Jones & Bartlett Learning, 2003^
  60. Application of Nanotechnology in Drug Delivery INTECH, 2016, retrieved 24 July 2019^
  61. The penicillins Mayo Clin Proc, March 1999^
  62. Physicochemical properties of antibiotics: A review with an emphasis on detection in the aquatic environment Water Environ Res, February 2020^
  63. Amoxicillin PubChem, retrieved 15 October 2024^
  64. Lung penetration and pneumococcal target binding of antibiotics in lower respiratory tract infection Curr Med Res Opin, December 2022^
  65. Penicillins^
  66. Penicillins^
  67. Introduction: historical perspective and development of amoxicillin/clavulanate International Journal of Antimicrobial Agents, December 2007^
  68. The Evolution of Drug Discovery Wiley-VCH, 2014^
  69. Synthesis of β-lactam antibiotics Springer, 2001^
  70. Penn Clinical Manual of Urology E-Book Elsevier Health Sciences, 2014, retrieved 18 March 2023^
  71. How Much Do Antibiotics Cost Without Insurance in 2021? retrieved 4 December 2022^
  72. Drug Approval Package: Moxatag (amoxicillin extended-release) NDA #050813 retrieved 25 December 2018^
  73. Pediatric Dentistry: Infancy Through Adolescence Saunders, 2018^
  74. A Quick Guide to Switch: Antibiotics: IV to Oral Safetyandquality.gov.au, retrieved 1 March 2022^
  75. Amoxicillin-bearing microparticles: potential in the treatment of Listeria monocytogenes infection in Swiss albino mice Bioscience Reports, August 2011^
  76. Amoxicillin [INN] pubchem.ncbi.nlm.nih.gov, retrieved 3 June 2024^
  77. Updating medicine ingredient names - list of affected ingredients Therapeutic Goods Administration, 5 April 2023, retrieved 15 October 2025^
  78. International brand names for amoxicillin Drugs.com, retrieved 15 November 2016^
  79. Amoxicillin fao.org, Food and Agriculture Organization of the United Nations, retrieved 8 November 2019^