Amoxicillin

Amoxicillin is an antibiotic used to treat some bacterial infections.^[3] It is one of the most common antibiotics given to children.^[4]

Amoxicillin

Clinical data
Pronunciation	/əˌmɒksɪˈsɪlɪn/
Trade names	Hundreds of names[1]
Synonyms	Amoxycillin, amox, Amoxycillin (AAN AU)
AHFS/Drugs.com	Monograph
MedlinePlus	a685001
License data	US DailyMed: Amoxicillin
Pregnancy category	AU: A
Routes of administration	By mouth, intravenous
Drug class	β-lactam antibiotic
ATC code	J01CA04 (WHO) QG51AA03 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only) US: ℞-only In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	95% by mouth
Metabolism	less than 30% biotransformed in liver
Elimination half-life	61.3 minutes
Excretion	Kidneys
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	26787-78-0 Y
PubChem CID	33613
DrugBank	DB01060 Y
ChemSpider	31006 Y
UNII	9EM05410Q9
KEGG	D07452 Y
ChEBI	CHEBI:2676 Y
ChEMBL	ChEMBL1082 Y
ECHA InfoCard	100.043.625
Chemical and physical data
Formula	C16H19N3O5S
Molar mass	365.40 g·mol−1
3D model (JSmol)	Interactive image
Density	1.6±0.1 [2] 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
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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

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. "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.