Amoxicillin

Amoxicillin

Clinical data
Pronunciation	/əˌmɒksᵻˈsɪlᵻn/
Trade names	Hundreds of names
AHFS/Drugs.com	Monograph
MedlinePlus	a685001
Pregnancy category	AU: A US: B (No risk in non-human studies)
Routes of administration	By mouth, intravenous
ATC code	J01CA04 (WHO) QG51AA03 (WHO)
Legal status
Legal status	UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	95% oral
Metabolism	less than 30% biotransformed in liver
Biological half-life	61.3 minutes
Excretion	renal
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-24-carboxylic acid
Synonyms	amoxicillin (INN, USAN); amoxycillin (BAN); amox
CAS Number	26787-78-0 Y
PubChem (CID)	33613
DrugBank	DB01060 Y
ChemSpider	31006 Y
UNII	9EM05410Q9 Y
KEGG	D07452 Y
ChEBI	CHEBI:2676 Y
ChEMBL	CHEMBL1082 Y
ECHA InfoCard	100.043.625
Chemical and physical data
Formula	C16H19N3O5S
Molar mass	365.4 g/mol
3D model (Jmol)	Interactive image
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

Amoxicillin is an antibiotic useful for the treatment of a number of bacterial infections. It is the first line treatment for middle ear infections. It may also be used for strep throat, pneumonia, skin infections, and urinary tract infections among others. It is taken by mouth, or less commonly by injection.

Common side effects include nausea and rash. It may also increase the risk of yeast infections and, when used in combination with clavulanic acid, diarrhea. It should not be used in those who are allergic to penicillin. While usable in those with kidney problems, the dose may need to be decreased. Its use in pregnancy and breastfeeding does not appear to be harmful.

Amoxicillin was discovered in 1958 and came into medical use in 1972. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. It is one of the most commonly prescribed antibiotics in children. Amoxicillin is available as a generic medication. It has a wholesale cost in the developing world of between 0.02 and 0.05 USD per pill. In the United States ten days of treatment costs about 16 USD.

Amoxicillin is used in the treatment of a number of infections, including acute otitis media, , pneumonia, skin infections, urinary tract infections, Salmonella infections, Lyme disease, and chlamydia infections.