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

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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