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PubChem
| Name: | Azithromycin |
|---|---|
| PubChem Compound ID: | 11969951 |
| Description: | A semi-synthetic macrolide antibiotic structurally related to ERYTHROMYCIN. It has been used in the treatment of Mycobacterium avium intracellulare infections, toxoplasmosis, and cryptosporidiosis. |
| Molecular formula: | C38H72N2O12 |
| Molecular weight: | 748.985 g/mol |
| Synonyms: |
Azithromycin; NSC643732
|
DrugBank
Identification
| Name: | Azithromycin |
|---|---|
| Name (isomeric): | DB00207 |
| Drug Type: | small molecule |
| Description: | A semi-synthetic macrolide antibiotic structurally related to ERYTHROMYCIN. It has been used in the treatment of Mycobacterium avium intracellulare infections, toxoplasmosis, and cryptosporidiosis. |
| Synonyms: |
Aritromicina [Spanish]; Azithramycine; Azithromycinum [Latin]; Azithromycine [French]; Azithromycin Dihydrate
|
| Brand: | Vinzam, Zifin, Aztrin, Setron, Zitrocin, Zitrim, Mixoterin, Tobil, Zitrotek, Azenil, Zitromax, Zithromax, Zithrax, Azibiot, Azifine, Aziwok, Misultina, Hemomycin, Sumamed, Zeto, Tromix, Zmax, Azitromax |
| Category: | Anti-Bacterial Agents, Other Macrolides, Macrolides |
| CAS number: | 83905-01-5 |
Pharmacology
| Indication: | For the treatment of patients with mild to moderate infections caused by susceptible strains of the designated microorganisms in the specific conditions: <i>H. influenzae</i>, <i>M. catarrhalis</i>, <i>S. pneumoniae</i>, <i>C. pneumoniae</i>, <i>M. pneumoniae</i>, <i>S. pyogenes</i>, <i>S. aureus</i>, <i>S. agal</i> |
|---|---|
| Pharmacology: |
Azithromycin, a semisynthetic antibiotic belonging to the macrolide subgroup of azalides, is used to treat STDs due to chlamydia and gonorrhea, community-acquired pneumonia, pelvic inflammatory disease, pediatric otitis media and pharyngitis, and Mycobacterium avium complex (MAC) in patients with advanced HIV disease. Similar in structure to...
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| Mechanism of Action: | Azithromycin binds to the 50S subunit of the 70S bacterial ribosomes, and therefore inhibits RNA-dependent protein synthesis in bacterial cells. |
| Absorption: | Bioavailability is 37% following oral administration. Absorption is not affected by food. Azithromycin is extensively distributed in tissues with tissue concentrations reaching up to 50 times greater than plasma concentrations. Drug becomes concentrated within macrophages and polymorphonucleocytes giving it good activity against Chlamydia trachomatis. |
| Protein binding: | Serum protein binding is variable in the concentration range approximating human exposure, decreasing from 51% at 0.02 µg/mL to 7% at 2 µg/mL. |
| Biotransformation: | Hepatic. In vitro and in vivo studies to assess the metabolism of azithromycin have not been performed. |
| Route of elimination: | Biliary excretion of azithromycin, predominantly as unchanged drug, is a major route of elimination. |
| Half Life: | 68 hours |
| Clearance: | apparent plasma cl=630 mL/min [following single 500 mg oral and i.v. doses] |
| Toxicity: | Potentially serious side effects of angioedema and cholestatic jaundice were reported |
| Affected organisms: | Enteric bacteria and other eubacteria |
Interactions
| Food interaction: |
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