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Amoxicillin

From Simple English Wikipedia, the free encyclopedia
Amoxicillin
Clinical data
Pronunciation/əˌmɒksɪˈsɪlɪn/
Trade namesHundreds of names[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
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • 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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.043.625 Edit this at Wikidata
Chemical and physical data
FormulaC16H19N3O5S
Molar mass365.40 g·mol−1
3D model (JSmol)
Density1.6±0.1 [2] 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 some bacterial infections.[3] It is one of the most common antibiotics given to children.[4]

It may be given for middle ear infection, strep throat, pneumonia, skin infections, infections caused by Helicobacter pylori, and urinary tract infections among others.[3] It is taken by mouth, or less commonly by injection.[3][5]

Common adverse effects are nausea and a rash.[3] It can also make yeast infections more likely. When taken with clavulanic acid, it can cause diarrhea.[6] It should not be used on someone allergic to penicillin. [3] It can be used for people with kidney problems, but less should be given than normal.[3] It may be used on pregnant women or women who are breastfeeding.[3]

Amoxicillin was discovered in 1958 by Anthony Alfred Walter Long and John Herbert Charles Nayler. Its use started in 1972.[7][8] It is on the (WHO) World Health Organization's List of Essential Medicines.[9] Amoxicillin is cheap and commonly used.[10]

References

[change | change source]
  1. ↑ "International brand names for amoxicillin". www.drugs.com. Drugs.com. Archived from the original on 29 May 2016. Retrieved 15 November 2016.
  2. ↑ "Amoxicillin". www.chemsrc.com.
  3. 1 2 3 4 5 6 7 "Amoxicillin". The American Society of Health-System Pharmacists. Archived from the original on 5 September 2015. Retrieved 1 August 2015.
  4. ↑ 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.
  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 (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.
  7. ↑ 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.
  8. ↑ 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.
  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. ↑ Hanno, Philip M.; Guzzo, Thomas J.; Malkowicz, S. Bruce; Wein, Alan J. (2014-01-26). Penn Clinical Manual of Urology E-Book: Expert Consult - Online. Elsevier Health Sciences. ISBN 978-0-323-24466-4.