Azithromycin

Azithromycin
Clinical data
Trade namesZithromax, others
Other names9-deoxy-9α-aza-9α-methyl-9α-homoerythromycin A
AHFS/Drugs.comMonograph
MedlinePlusa697037
License data
Pregnancy
category
  • AU: B1
Routes of
administration
By mouth, intravenous, eye drops
Drug classMacrolide antibiotic
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability38% for 250 mg capsules
MetabolismLiver
Elimination half-life68 h
ExcretionBile duct
Identifiers
  • (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
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
ECHA InfoCard100.126.551
Chemical and physical data
FormulaC38H72N2O12
Molar mass748.996 g·mol−1
3D model (JSmol)
  • 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=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
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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 several bacterial infections. This includes middle ear infections, strep throat, pneumonia, traveler's diarrhea, STI and certain other intestinal infections. Along with other medications, it may also be used for malaria. It is administered by mouth, into a vein, or into the eye.

Common side effects include nausea, vomiting, diarrhea and upset stomach. An allergic reaction, such as anaphylaxis, or a type of diarrhea caused by Clostridioides difficile is possible. Azithromycin causes QT prolongation that may cause life-threatening arrhythmias such as torsades de pointes. While some studies claim that no harm has been found with use during pregnancy, more recent studies with mice during late pregnancy has shown adverse effects on embryonic testicular and neural development of prenatal azithromycin exposure (PAzE). However, there need to be more well-controlled studies in pregnant women. 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 Yugoslavia (present day Croatia) in 1980 by the pharmaceutical company Pliva and approved for medical use in 1988. It is on the World Health Organization's List of Essential Medicines. The World Health Organization lists it as an example under "Macrolides and ketolides" in its Critically Important Antimicrobials for Human Medicine (designed to help manage antimicrobial resistance). It is available as a generic medication and is sold under many brand names worldwide. In 2022, it was the 78th most commonly prescribed medication in the United States, with more than 8 million prescriptions.