Amoxicillin

Not to be confused with Ampicillin.

Amoxicillin
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 (bolus), intramuscular
Drug classβ-Lactam antibiotic; Aminopenicillin
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityOral: 60%[7]
Protein binding17%[7]
MetabolismHydroxylation, oxidative deamination, aliphatic chain oxidation, decarboxylation, glucuronidation[7]
MetabolitesSeven[7]
Onset of action≤1.3–1.5 hours (TmaxTooltip time to peak concentrations)[7]
Elimination half-life61.3 minutes (~1 hour)[7]
ExcretionUrine: 70–78% (after 6 hours)[7]
Identifiers
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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.043.625
Chemical and physical data
FormulaC16H19N3O5S
Molar mass365.40 g·mol−1
3D model (JSmol)
Density1.6±0.1 [8] g/cm3
SMILES
  • O=C(O)[C@@H]2N3C(=O)[C@@H](NC(=O)[C@@H](c1ccc(O)cc1)N)[C@H]3SC2(C)C
InChI
  • 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 Y
  • Key:LSQZJLSUYDQPKJ-NJBDSQKTSA-N Y
  (verify)

Amoxicillin is an antibiotic medication belonging to the aminopenicillin class of the penicillin family. The drug is used to treat bacterial infections[9] such as middle ear infection, strep throat, pneumonia, skin infections, odontogenic infections, and urinary tract infections.[9] 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.[9][10]

Common adverse effects include nausea and rash.[9] It may also increase the risk of yeast infections and, when used in combination with clavulanic acid, diarrhea.[11] It should not be used in those who are allergic to penicillin.[9] While usable in those with kidney problems, the dose may need to be decreased.[9] Its use in pregnancy and breastfeeding does not appear to be harmful.[9] Amoxicillin is in the β-lactam family of antibiotics.[9]

Amoxicillin was discovered in 1958 and came into medical use in 1972.[12][13] 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 World Health Organization's List of Essential Medicines.[14] It is one of the most commonly prescribed antibiotics in children.[15] Amoxicillin is available as a generic medication.[9] In 2022, it was the 26th most commonly prescribed medication in the United States, with more than 20 million prescriptions.[16][17]

  1. ^ Cite error: The named reference brands was invoked but never defined (see the help page).
  2. ^ a b "Amoxil Vials for Injection 500mg - Summary of Product Characteristics (SmPC)". (emc). 4 November 2021. Archived from the original on 10 October 2022. Retrieved 8 October 2022.
  3. ^ "Amoxil (amoxicillin) Capsules, Tablets, Chewable Tablets, and Powder for Oral Suspension". DailyMed. Archived from the original on 9 October 2022. Retrieved 8 October 2022. Central Nervous System: Reversible hyperactivity, agitation, anxiety, insomnia, confusion, convulsions, behavioral changes, and/or dizziness have been reported rarely.
  4. ^ 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.
  5. ^ 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.
  6. ^ "Moxatag (amoxicillin extended-release) Tablets Initial U.S. Approval: 1974". DailyMed. Archived from the original on 9 October 2022. Retrieved 8 October 2022.
  7. ^ a b c d e f g "Amoxicillin: Uses, Interactions, Mechanism of Action". DrugBank Online. 18 January 1974. Retrieved 5 November 2024.
  8. ^ "Amoxicillin". www.chemsrc.com. Archived from the original on 19 May 2017. Retrieved 8 May 2018.
  9. ^ 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.
  10. ^ "Amoxicillin Sodium for Injection". EMC. 10 February 2016. Archived from the original on 27 October 2016. Retrieved 26 October 2016.
  11. ^ 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.
  12. ^ 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.
  13. ^ 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.
  14. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  15. ^ 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.
  16. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  17. ^ "Amoxicillin Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
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