Beta-lactam antibiotic
Amoxicillin Pronunciation Trade names Amoxil, Trimox, others[ 1] Other names Amoxycillin, amox, Amoxycillin (AAN AU ) AHFS /Drugs.com Monograph MedlinePlus a685001 License data
Pregnancy category Routes of administration By mouth , Bolus IV , Intramuscular injection Drug class β-lactam antibiotic, aminopenicillin ATC code Legal status
Bioavailability 95% by mouth Metabolism less than 30% biotransformed in liver Elimination half-life 61.3 minutes Excretion Kidneys
(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
CAS Number PubChem CID DrugBank ChemSpider UNII KEGG ChEBI ChEMBL CompTox Dashboard (EPA ) ECHA InfoCard 100.043.625 Formula C 16 H 19 N 3 O 5 S Molar mass 365.40 g·mol−1 3D model (JSmol ) Density 1.6±0.1 [ 7] g/cm3
O=C(O)[C@@H]2N3C(=O)[C@@H](NC(=O)[C@@H](c1ccc(O)cc1)N)[C@H]3SC2(C)C
InChI=1S/C16H19N3O5S/c1-16(2)11(15(23)24)19-13(22)10(14(19)25-16)18-12(21)9(17)7-3-5-8(20)6-4-7/h3-6,9-11,14,20H,17H2,1-2H3,(H,18,21)(H,23,24)/t9-,10-,11+,14-/m1/s1
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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 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 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,[ 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]
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^ "Amoxil (amoxicillin) Capsules, Tablets, Chewable Tablets, and Powder for Oral Suspension" . DailyMed . Archived from the original on 9 October 2022. Retrieved 8 October 2022 .
^ a b "Amoxil: FDA-Approved Drugs" . U.S. Food and Drug Administration (FDA) . Archived from the original on 9 October 2022. Retrieved 8 October 2022 .
^ a b "Trimox: FDA-Approved Drugs" . U.S. Food and Drug Administration (FDA) . Archived from the original on 9 October 2022. Retrieved 8 October 2022 .
^ "Moxatag (amoxicillin extended-release) Tablets Initial U.S. Approval: 1974" . DailyMed . Archived from the original on 9 October 2022. Retrieved 8 October 2022 .
^ "Amoxicillin" . www.chemsrc.com . Archived from the original on 19 May 2017. Retrieved 8 May 2018 .
^ a b c d e f g h i "Amoxicillin" . Drugs.com, The American Society of Health-System Pharmacists. 3 January 2022. Archived from the original on 24 November 2022. Retrieved 24 November 2022 .
^ "Amoxicillin Sodium for Injection" . EMC . 10 February 2016. Archived from the original on 27 October 2016. Retrieved 26 October 2016 .
^ Gillies M, Ranakusuma A, Hoffmann T, Thorning S, McGuire T, Glasziou P, et al. (January 2016). "Common harms from amoxicillin: a systematic review and meta-analysis of randomized placebo-controlled trials for any indication" . CMAJ . 187 (1): E21–E31. doi :10.1503/cmaj.140848 . PMC 4284189 . PMID 25404399 .
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery . John Wiley & Sons. p. 490. ISBN 978-3-527-60749-5 . Archived from the original on 8 September 2017.
^ Roy J (2012). An introduction to pharmaceutical sciences production, chemistry, techniques and technology . Cambridge: Woodhead Pub. p. 239. ISBN 978-1-908818-04-1 . Archived from the original on 8 September 2017.
^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019 . Geneva: World Health Organization. hdl :10665/325771 . WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021) . Geneva: World Health Organization. hdl :10665/345533 . WHO/MHP/HPS/EML/2021.02.
^ Kelly D (2008). Diseases of the liver and biliary system in children (3 ed.). Chichester, UK: Wiley-Blackwell. p. 217. ISBN 978-1-4443-0054-3 . Archived from the original on 8 September 2017.
^ "The Top 300 of 2021" . ClinCalc . Archived from the original on 15 January 2024. Retrieved 14 January 2024 .
^ "Amoxicillin - Drug Usage Statistics" . ClinCalc . Archived from the original on 11 April 2020. Retrieved 14 January 2024 .