Clinical data | |
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Trade names | Zithromax, others[1] |
Other names | 9-deoxy-9α-aza-9α-methyl-9α-homoerythromycin A |
AHFS/Drugs.com | Monograph |
MedlinePlus | a697037 |
License data |
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Pregnancy category |
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Routes of administration | By mouth, intravenous, eye drops |
Drug class | Macrolide antibiotic |
ATC code | |
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Pharmacokinetic data | |
Bioavailability | 38% for 250 mg capsules |
Metabolism | Liver |
Elimination half-life | 68 h |
Excretion | Bile duct[8] |
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IUPHAR/BPS | |
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KEGG | |
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ChEMBL | |
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CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.126.551 |
Chemical and physical data | |
Formula | C38H72N2O12 |
Molar mass | 748.996 g·mol−1 |
3D model (JSmol) | |
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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.[10] This includes middle ear infections, strep throat, pneumonia, traveler's diarrhea, and certain other intestinal infections.[10] Along with other medications, it may also be used for malaria.[10] It is administered by mouth, into a vein, or into the eye.[10]
Common side effects include nausea, vomiting, diarrhea and upset stomach.[10] An allergic reaction, such as anaphylaxis, or a type of diarrhea caused by Clostridioides difficile is possible.[10] Azithromycin causes QT prolongation that may cause life-threatening arrhythmias such as torsades de pointes.[11] No harm has been found with its use during pregnancy.[10] Its safety during breastfeeding is not confirmed, but it is likely safe.[12] Azithromycin is an azalide, a type of macrolide antibiotic.[10] It works by decreasing the production of protein, thereby stopping bacterial growth.[10][13]
Azithromycin was discovered in Yugoslavia (present day Croatia) in 1980 by the pharmaceutical company Pliva and approved for medical use in 1988.[14][15] It is on the World Health Organization's List of Essential Medicines.[16] 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).[17] It is available as a generic medication[18] and is sold under many brand names worldwide.[1] In 2022, it was the 78th most commonly prescribed medication in the United States, with more than 8 million prescriptions.[19][20]
Zithromax FDA label
was invoked but never defined (see the help page).