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User:Mr. Ibrahem/Amoxicillin

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Not to be confused with Ampicillin.
Mr. Ibrahem/Amoxicillin
Clinical data
Pronunciation/əˌmɒksɪˈsɪlɪn/
Trade namesHundreds of names
SynonymsAmoxycillin, amox, amoxycillin (AAN AU)
AHFS/Drugs.comMonograph
MedlinePlusa685001
License data
Pregnancy
category
  • AU: A
Routes of
administration		By mouth, intravenous
Drug classβ-lactam antibiotic
Legal status
Legal status
  • UK: POM (Prescription only)
  • US: ℞-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability95% by mouth
Metabolismless than 30% biotransformed in liver
Elimination half-life61.3 minutes
ExcretionKidneys
Identifiers
  • (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
Chemical and physical data
FormulaC16H19N3O5S
Molar mass365.40 g·mol−1
3D model (JSmol)
Density1.6±0.1 [1] 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 checkY
  • Key:LSQZJLSUYDQPKJ-NJBDSQKTSA-N checkY
  (verify)

Amoxicillin is an antibiotic used to treat a number of bacterial infections.[2] These include middle ear infection, strep throat, pneumonia, skin infections, and urinary tract infections among others.[4][2] It is taken by mouth, or less commonly by injection.[2][5]

Common adverse effects include nausea and rash.[2] It may also increase the risk of yeast infections and, when used in combination with clavulanic acid, diarrhea.[6] It should not be used in those who are allergic to penicillin.[2] While usable in those with kidney problems, the dose may need to be decreased.[2] Its use in pregnancy and breastfeeding does not appear to be harmful.[2] Amoxicillin is in the beta-lactam family of antibiotics.[2]

Amoxicillin was discovered in 1958 and came into medical use in 1972.[7][8] It is on the World Health Organization's List of Essential Medicines.[9] It is one of the most commonly prescribed antibiotics in children.[10] Amoxicillin is available as a generic medication and is relatively inexpensive.[2] In 2017, it was the 18th most commonly prescribed medication in the United States, with more than 27 million prescriptions.[11][12]

References

[change | change source]
  1. ↑ "Amoxicillin". www.chemsrc.com. Archived from the original on 2017-05-19. Retrieved 2018-05-08.
  2. ↑ 2.00 2.01 2.02 2.03 2.04 2.05 2.06 2.07 2.08 2.09 2.10 "Amoxicillin". The American Society of Health-System Pharmacists. Archived from the original on 5 September 2015. Retrieved 1 August 2015.
  3. ↑ "WHOCC - ATC/DDD Index". www.whocc.no. Archived from the original on 7 October 2020. Retrieved 22 September 2020.
  4. ↑ Ritter, James M.; Flower, Rod; Henderson, Graeme; Loke, Yoon Kong; Robinson, Emma; Fullerton, James (2024). "52. Antibacterial drugs". Rang & Dale's Pharmacology (10th ed.). Elsevier. p. 707. ISBN 978-0-7020-7448-6. Archived from the original on 2024-02-10. Retrieved 2024-01-30.
  5. ↑ "Amoxicillin Sodium for Injection". EMC. 10 February 2016. Archived from the original on 27 October 2016. Retrieved 26 October 2016.
  6. ↑ Gillies, M; Ranakusuma, A; Hoffmann, T; Thorning, S; McGuire, T; Glasziou, P; Del Mar, C (17 November 2014). "Common harms from amoxicillin: a systematic review and meta-analysis of randomized placebo-controlled trials for any indication". CMAJ : Canadian Medical Association Journal. 187 (1): E21–31. doi:10.1503/cmaj.140848. PMC 4284189. PMID 25404399.
  7. ↑ Fischer, Janos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 490. ISBN 9783527607495. Archived from the original on 2017-09-08.
  8. ↑ Roy, Jiben (2012). An introduction to pharmaceutical sciences production, chemistry, techniques and technology. Cambridge: Woodhead Pub. p. 239. ISBN 9781908818041. Archived from the original on 2017-09-08.
  9. ↑ 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.
  10. ↑ Kelly, Deirdre (2008). Diseases of the liver and biliary system in children (3 ed.). Chichester, UK: Wiley-Blackwell. p. 217. ISBN 9781444300543. Archived from the original on 2017-09-08.
  11. ↑ "The Top 300 of 2020". ClinCalc. Archived from the original on 18 March 2020. Retrieved 11 April 2020.
  12. ↑ "Amoxicillin Drug Usage Statistics". ClinCalc. 1 December 1981. Archived from the original on 11 April 2020. Retrieved 11 April 2020.
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