Amoxicillin

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Amoxicillin
Amoxicillin.svg
Amoxicillin-from-xtal-3D-bs-17.png
Clinical data
Pronunciation/əˌmɒksɪˈsɪlɪn/
Trade namesHundreds of names[1]
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
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
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, and urinary tract infections among others.[3] It is taken by mouth, or less commonly by injection.[3][5]

Common bad side 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 and its use started in 1972.[7][8] It is on the (WHO) World Health Organization's List of Essential Medicines.[9]

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. 3.0 3.1 3.2 3.3 3.4 3.5 3.6 "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.