Azithromycin

Azithromycin

Clinical data
Trade names	Zithromax, Azithrocin, others
AHFS/Drugs.com	Monograph
MedlinePlus	a697037
License data	US FDA: Azithromycin
Pregnancy category	AU: B1 US: B (No risk in non-human studies)
Routes of administration	(capsule, tablet or suspension), intravenous, ophthalmic
ATC code	J01FA10 (WHO) S01AA26 (WHO)
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Bioavailability	38% for 250 mg capsules
Metabolism	Hepatic
Biological half-life	11–14 h (single dose) 68 h (multiple dosing)
Excretion	Biliary, renal (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-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranoside
Synonyms	9-deoxy-9α-aza-9α-methyl-9α-homoerythromycin A
CAS Number	83905-01-5 Y
PubChem CID	55185
IUPHAR/BPS	6510
DrugBank	DB00207 Y
ChemSpider	10482163 Y
UNII	J2KLZ20U1M
KEGG	D07486 Y
ChEBI	CHEBI:2955 Y
ChEMBL	CHEMBL529 Y
NIAID ChemDB	007311
ECHA InfoCard	100.126.551
Chemical and physical data
Formula	C38H72N2O12
Molar mass	748.984 g·mol−1
3D model (Jmol)	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 Y Key:MQTOSJVFKKJCRP-BICOPXKESA-N Y

11–14 h (single dose)

Azithromycin is an antibiotic useful 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. It may also be used for a number of sexually transmitted infections including chlamydia and gonorrhea infections. Along with other medications, it may also be used for malaria. It can be taken by mouth or intravenously with doses once per day.

Common side effects include nausea, vomiting, diarrhea and upset stomach. An allergic reaction 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, thus stopping bacterial growth.

Azithromycin was first made in 1980. 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 available as a generic medication and is sold under many trade names worldwide. The wholesale cost in the developing world is about 0.18 to 2.98 USD per dose. In the United States it is about 33 USD for a course of treatment.