Azithromycin

Azithromycin
Clinical data
Trade names	Zithromax, Azithrocin, Sumamed, others
Other names	9-deoxy-9α-aza-9α-methyl-9α-homoerythromycin A
AHFS/Drugs.com	Monograph
MedlinePlus	a697037
License data	US DailyMed: Azithromycin;
Pregnancy; category	AU: B1;
Routes of; administration	By mouth (capsule, tablet or suspension), intravenous, eye drop
Drug class	Macrolide antibiotic
ATC code	J01FA10 (WHO) S01AA26 (WHO) J01RA07 (WHO);
Legal status
Legal status	US: WARNINGRx-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	38% for 250 mg capsules
Metabolism	Liver
Elimination half-life	11–14 h (small doses) 68 h (large or multiple dosing)
Excretion	Bile duct, kidney (4.5%)
Identifiers
	IUPAC name (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-15-oxo- 11-{[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy}-1-oxa-6-azacyclopentadec-13-yl 2,6-dideoxy-3C-methyl-3-O-methyl-α-L-ribo-hexopyranoside;
CAS Number	83905-01-5 ;
PubChem CID	55185;
IUPHAR/BPS	6510;
DrugBank	DB00207 ;
ChemSpider	10482163 ;
UNII	J2KLZ20U1M;
KEGG	D07486 ;
ChEBI	CHEBI:2955 ;
ChEMBL	ChEMBL529 ;
NIAID ChemDB	007311;
CompTox Dashboard (EPA)	DTXSID8030760 ;
ECHA InfoCard	100.126.551
Chemical and physical data
Formula	C38H72N2O12
Molar mass	748.996 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN(C)[C@H]3C[C@@H](C)O[C@@H](O[C@@H]2[C@@H](C)[C@H](O[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1)[C@@H](C)C(=O)O[C@H](CC)[C@@](C)(O)[C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@]2(C)O)[C@@H]3O;
	InChI InChI=1S/C38H72N2O12/c1-15-27-38(10,46)31(42)24(6)40(13)19-20(2)17-36(8,45)33(52-35-29(41)26(39(11)12)16-21(3)48-35)22(4)30(23(5)34(44)50-27)51-28-18-37(9,47-14)32(43)25(7)49-28/h20-33,35,41-43,45-46H,15-19H2,1-14H3/t20-,21-,22+,23-,24-,25+,26+,27-,28+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1 ; Key:MQTOSJVFKKJCRP-BICOPXKESA-N ;
	GLAH&page2=Azithromycin (verify)

Azithromycin, sold under the brand names Zithromax (in oral form) and Azasite (as an eye drop), is an antibiotic medication used for the treatment of a number of bacterial infections. This includes middle ear infections, strep throat, pneumonia, traveler's diarrhea, and certain other intestinal infections. Along with other medications, it may also be used for malaria. It can be taken by mouth or intravenously.

Common side effects include nausea, vomiting, diarrhea and upset stomach. An allergic reaction, such as anaphylaxis, QT prolongation, or a type of diarrhea caused by Clostridium difficile is possible. No harm has been found with its use during pregnancy. Its safety during breastfeeding is not confirmed, but it is likely safe. Azithromycin is an azalide, a type of macrolide antibiotic. It works by decreasing the production of protein, thereby stopping bacterial growth.

Azithromycin was discovered in Croatia in 1980 by the pharmaceutical company Pliva and approved for medical use in 1988 under the brand name Sumamed. It is on the World Health Organization's List of Essential Medicines. The World Health Organization classifies it as critically important for human medicine. It is available as a generic medication and is sold under many trade names worldwide. In 2021, it was the 97th most commonly prescribed medication in the United States, with more than 7 million prescriptions.

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