Chemistry:Amoxicillin

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Short description: Beta-lactam antibiotic
Amoxicillin
Amoxicillin.svg
Amoxicillin-from-xtal-3D-bs-17.png
Clinical data
Pronunciation/əˌmɒksɪˈsɪlɪn/
Trade namesAmoxil, Trimox, others[1]
Other namesAmoxycillin, amox, Amoxycillin (AAN AU)
AHFS/Drugs.comMonograph
MedlinePlusa685001
License data
Pregnancy
category
  • AU: A
Routes of
administration		By mouth, intravenous
Drug classβ-lactam antibiotic, aminopenicillin
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability95% by mouth
Metabolismless than 30% biotransformed in liver
Elimination half-life61.3 minutes
ExcretionKidneys
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC16H19N3O5S
Molar mass365.40 g·mol−1
3D model (JSmol)
Density1.6±0.1 [7] g/cm3
  (verify)

Amoxicillin is an antibiotic medication belonging to the aminopenicillin class of the penicillin family. The drug is used to treat bacterial infections[8] such as middle ear infection, strep throat, pneumonia, skin infections, odontogenic infections, and urinary tract infections.[8] It is taken by mouth, or less commonly by injection.[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,[4][5] and in the United Kingdom in 1977.[2] It is on the (WHO) World Health Organization's List of Essential Medicines.[13][14] It is one of the most commonly prescribed antibiotics in children.[15] Amoxicillin is available as a generic medication.[8] In 2021, it was the 38th most commonly prescribed medication in the United States, with more than 16 million prescriptions.[16][17]

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.[8][18]

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.[19] 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.[20]

Respiratory infections

Most sinusitis infections are caused by viruses, for which amoxicillin and amoxicillin-clavulanate are ineffective,[21] and the small benefit gained by amoxicillin may be overridden by the adverse effects.[22] Amoxicillin is considered the first-line empirical treatment for most cases of uncomplicated bacterial sinusitis in children and adults when culture data is unavailable.[23][24][25] 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.[26] The World Health Organization (WHO) recommends amoxicillin as first-line treatment for pneumonia that is not "severe".[27] Amoxicillin is used in post-exposure inhalation of anthrax to prevent disease progression and for prophylaxis.[18]

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.[28]

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.[29]

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.[30]

Skin infections

Amoxicillin is occasionally used for the treatment of skin infections,[18] such as acne vulgaris.[31] It is often an effective treatment for cases of acne vulgaris that have responded poorly to other antibiotics, such as doxycycline and minocycline.[32]

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.[33]

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, such as people 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.[34] These recommendations do not appear to have changed the rates of infection for infectious endocarditis.[35]

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.[36]

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.[37] Some E. coli and most clinical strains of Staphylococcus aureus have developed resistance to amoxicillin to varying degrees.[38]

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.[8]

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.[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.[39][40]

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.[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.[41]

The rash is described as maculopapular or morbilliform (measles-like; therefore, in medical literature, it is called "amoxicillin-induced morbilliform rash".[42]). 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.[43][44]

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.[45]

  • 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:

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.[51] 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.[18]

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.[18] As a derivative of ampicillin, amoxicillin is a member of the penicillin family and, like penicillins, is a β-lactam antibiotic.[52] 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).[53]

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.[54][55] It became available in 1972 and was the second aminopenicillin to reach the market (after ampicillin in 1961).[56][57][58] Co-amoxiclav became available in 1981.[57]

Society and culture

Economics

Amoxicillin is relatively inexpensive.[59] In 2022, a survey of 8 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.[60]

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.[6][61] The intravenous form of amoxicillin is not sold in the United States.[62] 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.[63]

Research with mice indicated successful delivery using intraperitoneally injected amoxicillin-bearing microparticles.[64]

Names

"Amoxicillin" is the International Nonproprietary Name (INN), British Approved Name (BAN), and United States Adopted Name (USAN), while "amoxycillin" is the Australian Approved Name (AAN).[citation needed]

Amoxicillin is one of the semisynthetic penicillins discovered by 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.[1]

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.[65]

References

  1. ↑ 1.0 1.1 "International brand names for amoxicillin". https://www.drugs.com/international/amoxicillin.html. 
  2. ↑ 2.0 2.1 "Amoxil Vials for Injection 500mg - Summary of Product Characteristics (SmPC)". 4 November 2021. https://www.medicines.org.uk/emc/product/94/smpc. 
  3. ↑ "Amoxil (amoxicillin) Capsules, Tablets, Chewable Tablets, and Powder for Oral Suspension". https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=49302. 
  4. ↑ 4.0 4.1 "Amoxil: FDA-Approved Drugs". https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=050459. 
  5. ↑ 5.0 5.1 "Trimox: FDA-Approved Drugs". https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=061885. 
  6. ↑ 6.0 6.1 "Moxatag (amoxicillin extended-release) Tablets Initial U.S. Approval: 1974". https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=364489. 
  7. ↑ "Amoxicillin". https://www.chemsrc.com/en/cas/26787-78-0_946616.html. 
  8. ↑ 8.00 8.01 8.02 8.03 8.04 8.05 8.06 8.07 8.08 8.09 8.10 8.11 8.12 "Amoxicillin". Drugs.com, The American Society of Health-System Pharmacists. 3 January 2022. https://www.drugs.com/amoxicillin.html. 
  9. ↑ "Amoxicillin Sodium for Injection". 10 February 2016. https://www.medicines.org.uk/emc/medicine/5359. 
  10. ↑ 10.0 10.1 "Common harms from amoxicillin: a systematic review and meta-analysis of randomized placebo-controlled trials for any indication". CMAJ 187 (1): E21–E31. January 2016. doi:10.1503/cmaj.140848. PMID 25404399. 
  11. ↑ Analogue-based Drug Discovery. John Wiley & Sons. 2006. p. 490. ISBN 978-3-527-60749-5. https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA490. 
  12. ↑ An introduction to pharmaceutical sciences production, chemistry, techniques and technology. Cambridge: Woodhead Pub.. 2012. p. 239. ISBN 978-1-908818-04-1. https://books.google.com/books?id=0IdmAgAAQBAJ&pg=PA239. 
  13. ↑ World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. 2019. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO. 
  14. ↑ World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. 2021. WHO/MHP/HPS/EML/2021.02. 
  15. ↑ Diseases of the liver and biliary system in children (3 ed.). Chichester, UK: Wiley-Blackwell. 2008. p. 217. ISBN 978-1-4443-0054-3. https://books.google.com/books?id=z7nO3OrNXckC&pg=PA217. 
  16. ↑ "The Top 300 of 2021". https://clincalc.com/DrugStats/Top300Drugs.aspx. 
  17. ↑ "Amoxicillin - Drug Usage Statistics". https://clincalc.com/DrugStats/Drugs/Amoxicillin. 
  18. ↑ 18.0 18.1 18.2 18.3 18.4 18.5 "Amoxicillin". Davis. 2017. http://davisplus.fadavis.com/3976/meddeck/pdf/amoxicillin.pdf. 
  19. ↑ Venekamp, Roderick P.; Sanders, Sharon L.; Glasziou, Paul P.; Rovers, Maroeska M. (15 November 2023). "Antibiotics for acute otitis media in children". The Cochrane Database of Systematic Reviews 11 (11): CD000219. doi:10.1002/14651858.CD000219.pub5. ISSN 1469-493X. PMID 37965923. 
  20. ↑ "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 (12): CD004975. December 2013. doi:10.1002/14651858.CD004975.pub3. PMID 24338106. 
  21. ↑ "Five Things Physicians and Patients Should Question". Choosing Wisely: An Initiative of the ABIM Foundation (American Academy of Allergy, Asthma, and Immunology). http://choosingwisely.org/wp-content/uploads/2012/04/5things_12_factsheet_AAAAI.pdf. Retrieved 14 August 2012. 
  22. ↑ "Antibiotics for acute maxillary sinusitis in adults". The Cochrane Database of Systematic Reviews (2): CD000243. February 2014. doi:10.1002/14651858.CD000243.pub3. PMID 24515610.  (Retracted, see doi:10.1002/14651858.cd000243.pub4. If this is an intentional citation to a retracted paper, please replace {{Retracted}} with {{Retracted|intentional=yes}}.)
  23. ↑ "Uncomplicated acute sinusitis and rhinosinusitis in adults: Treatment". https://www.uptodate.com/contents/uncomplicated-acute-sinusitis-and-rhinosinusitis-in-adults-treatment. 
  24. ↑  , Wikidata Q38897648
  25. ↑  , Wikidata Q104102440
  26. ↑ National Clinical Guideline Centre (UK) (2014). Pneumonia: Diagnosis and Management of Community– and Hospital-Acquired Pneumonia in Adults. National Institute for Health and Care Excellence: Clinical Guidelines, No. 191. National Institute for Health and Care Excellence (UK). https://www.ncbi.nlm.nih.gov/pubmedhealth/PMH0071334/. 
  27. ↑ Revised WHO Classification and Treatment of Pneumonia in Children at Health Facilities - NCBI Bookshelf. WHO Guidelines Approved by the Guidelines Review Committee. World Health Organization. 2014. ISBN 978-92-4-150781-3. https://www.ncbi.nlm.nih.gov/books/NBK264162/. 
  28. ↑ "ACG Clinical Guideline: Treatment of Helicobacter pylori Infection". The American Journal of Gastroenterology 112 (2): 212–239. February 2017. doi:10.1038/ajg.2016.563. PMID 28071659. 
  29. ↑ "Efficacy and Safety of Antibiotic Therapy in Early Cutaneous Lyme Borreliosis: A Network Meta-analysis". JAMA Dermatology 154 (11): 1292–1303. November 2018. doi:10.1001/jamadermatol.2018.3186. PMID 30285069. 
  30. ↑ "Amoxicillin/Clavulanic Acid for the Treatment of Odontogenic Infections: A Randomised Study Comparing Efficacy and Tolerability versus Clindamycin". International Journal of Dentistry 2015: 472470. 2015. doi:10.1155/2015/472470. PMID 26300919. 
  31. ↑ "Adolescent Acne: Management". http://www.medscape.com/viewarticle/430534_5. 
  32. ↑ "Amoxicillin and Acne Vulgaris". scienceofacne.com. 5 September 2012. http://scienceofacne.com/amoxicillin/. 
  33. ↑ Guideline: Managing Possible Serious Bacterial Infection in Young Infants When Referral Is Not Feasible - NCBI Bookshelf. WHO Guidelines Approved by the Guidelines Review Committee. World Health Organization. 2015. ISBN 978-92-4-150926-8. https://www.ncbi.nlm.nih.gov/books/NBK321136/. 
  34. ↑ "CG64 Prophylaxis against infective endocarditis: Full guidance". NICE. http://www.nice.org.uk/nicemedia/live/11938/40039/40039.pdf. 
  35. ↑ "Impact of the NICE guideline recommending cessation of antibiotic prophylaxis for prevention of infective endocarditis: before and after study". BMJ 342: d2392. May 2011. doi:10.1136/bmj.d2392. PMID 21540258. 
  36. ↑ "Amoxicillin Susceptibility and Resistance Data". http://www.toku-e.com/Assets/MIC/AmoxicillinClavulanate%20augmentin.pdf. 
  37. ↑ "Amoxicillin spectrum of bacterial susceptibility and Resistance". http://www.toku-e.com/Assets/MIC/Amoxicillin%20sodium%20salt.pdf. 
  38. ↑ "Antimicrobial resistance in Africa: a systematic review". BMC Infectious Diseases 17 (1): 616. September 2017. doi:10.1186/s12879-017-2713-1. PMID 28893183. 
  39. ↑ "Amoxicillin-clavulanic acid-induced hepatitis". American Journal of Otolaryngology 28 (1): 28–30. January 2007. doi:10.1016/j.amjoto.2006.06.007. PMID 17162128. 
  40. ↑ Disposition of Toxic Drugs and Chemicals in Man (8th ed.). Foster City, CA: Biomedical Publications. 2008. pp. 81–83. 
  41. ↑ "Amoxicillin Rash". Tufts Medicine MelroseWakefield Hospital. https://hhma.org/healthadvisor/pa-ampirash-hhg/. 
  42. ↑ "Role of delayed cellular hypersensitivity and adhesion molecules in amoxicillin-induced morbilliform rashes". Archives of Dermatology 133 (4): 481–6. April 1997. doi:10.1001/archderm.1997.03890400081011. INIST:2654598. PMID 9126012. 
  43. ↑ "A review of evidence supporting the American Academy of Pediatrics recommendation for prescribing cephalosporin antibiotics for penicillin-allergic patients". Pediatrics 115 (4): 1048–57. April 2005. doi:10.1542/peds.2004-1276. PMID 15805383. 
  44. ↑ Your child's health: the parents' one-stop reference guide to symptoms, emergencies, common illnesses, behavior problems, healthy development (2nd ed.). New York: Bantam Books. 2005. ISBN 978-0-553-38369-0. https://archive.org/details/yourchildshealth00bart. 
  45. ↑ "Ampicillin rash". The Western Journal of Medicine 126 (4): 333–5. April 1977. PMID 855325. 
  46. ↑ British National Formulary 57 March 2009
  47. ↑ 47.0 47.1 47.2 47.3 47.4 Pharmacotherapeutics for Advanced Practice: A Practical Approach. LWW. 17 August 2016. ISBN 978-1-496-31996-8. https://books.google.com/books?id=FBJRDAAAQBAJ&pg=PT770. 
  48. ↑ 48.0 48.1 48.2 48.3 48.4 48.5 "Antibiotics" (in en), Pharmacology in Clinical Neurosciences: A Quick Guide (Singapore: Springer): pp. 265–497, 2020, doi:10.1007/978-981-15-3591-8_10, ISBN 978-981-15-3591-8, https://doi.org/10.1007/978-981-15-3591-8_10, retrieved 9 April 2023 
  49. ↑ "Antibiotic and oral contraceptive drug interactions: Is there a need for concern?". The Canadian Journal of Infectious Diseases 10 (6): 429–433. November 1999. doi:10.1155/1999/539376. PMID 22346401. 
  50. ↑ "Chapter 32 - Rheumatology and Musculoskeletal Problems" (in en), Textbook of Family Medicine (Philadelphia: W.B. Saunders): pp. 648–689, January 2012, doi:10.1016/b978-1-4377-1160-8.10032-6, ISBN 978-1-4377-1160-8 
  51. ↑ "Amoxicillin, a new penicillin antibiotic". Antimicrobial Agents and Chemotherapy 3 (2): 262–5. February 1973. doi:10.1128/AAC.3.2.262. PMID 4208282. 
  52. ↑ Microbes and Society: An Introduction to Microbiology. Jones & Bartlett Learning. 2003. p. 198. ISBN 978-0-7637-1430-7. https://books.google.com/books?id=oRAZd3AlTlkC&pg=PA198. 
  53. ↑ Application of Nanotechnology in Drug Delivery. INTECH. 2016. p. 423. ISBN 978-953-51-1628-8. https://books.google.com/books?id=XiShDwAAQBAJ&pg=PA423. Retrieved 24 July 2019. 
  54. ↑ & Harry Smith"Penicillins" GB patent 978178, published 1964-12-16, assigned to Beecham Research Laboratories Ltd
  55. ↑ Long AA, Nayler JH, "Penicillins", GB patent 1241844, published 1971-08-04, assigned to Beecham Group LTD
  56. ↑ "Introduction: historical perspective and development of amoxicillin/clavulanate". International Journal of Antimicrobial Agents 30 (Suppl 2): S109-12. December 2007. doi:10.1016/j.ijantimicag.2007.07.015. PMID 17900874. 
  57. ↑ 57.0 57.1 The Evolution of Drug Discovery. Weinheim: Wiley-VCH. 2014. p. 262. ISBN 978-3-527-32669-3. 
  58. ↑ Synthesis of β-lactam antibiotics. Springer. 2001. p. 17. ISBN 978-0-7923-7060-4. 
  59. ↑ Penn Clinical Manual of Urology E-Book. Elsevier Health Sciences. 2014. p. 122. ISBN 978-0-323-24466-4. https://books.google.com/books?id=OQTbAgAAQBAJ&pg=PA122. 
  60. ↑ "How Much Do Antibiotics Cost Without Insurance in 2021?". https://www.talktomira.com/post/how-much-antibiotics-cost-without-insurance. 
  61. ↑ "Drug Approval Package: Moxatag (amoxicillin extended-release) NDA #050813". https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/050813_moxatag_toc.cfm. 
  62. ↑ Pediatric Dentistry: Infancy Through Adolescence. Saunders. 2018. ISBN 978-0-323-60826-8. 
  63. ↑ "A Quick Guide to Switch : Antibiotics: IV to Oral". https://www.safetyandquality.gov.au/wp-content/uploads/2012/02/4.3-A-Quick-Guide-to-Switch_Southern-Health.pdf. 
  64. ↑ "Amoxicillin-bearing microparticles: potential in the treatment of Listeria monocytogenes infection in Swiss albino mice". Bioscience Reports 31 (4): 265–72. August 2011. doi:10.1042/BSR20100027. PMID 20687896. 
  65. ↑ "Amoxicillin". Food and Agriculture Organization of the United Nations. http://www.fao.org/fileadmin/user_upload/vetdrug/docs/12-2012-amoxicillin.pdf. 

Further reading



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