Amoxicillin

Amoxicillin
Clinical data
Pronunciation	/əˌmɒksɪˈsɪlɪn/
Trade names	Hundreds of names
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 ;
PubChem CID	33613;
DrugBank	DB01060 ;
ChemSpider	31006 ;
UNII	9EM05410Q9;
KEGG	D07452 ;
ChEBI	CHEBI:2676 ;
ChEMBL	ChEMBL1082 ;
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 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 ; Key:LSQZJLSUYDQPKJ-NJBDSQKTSA-N ;
(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

↑ "International brand names for amoxicillin". www.drugs.com. Drugs.com. Archived from the original on 29 May 2016. Retrieved 15 November 2016.
↑ "Amoxicillin". www.chemsrc.com.
↑ ^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.
↑ 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.
↑ "Amoxicillin Sodium for Injection". EMC. 10 February 2016. Archived from the original on 27 October 2016. Retrieved 26 October 2016.
↑ 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.
↑ 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.
↑ 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.
↑ 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.

[brands-1] "International brand names for amoxicillin". www.drugs.com. Drugs.com. Archived from the original on 29 May 2016. Retrieved 15 November 2016.

[chemsrc-2] "Amoxicillin". www.chemsrc.com.

[AHFS2015-3] 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.

[Common_harms_from_amoxicillin:_a_sy-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.

[WHO21st-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.

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