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QuickView for Azithromycin (compound)


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:
Take on empty stomach: 1 hour before or 2 hours after meals.
Do not take Aluminum or magnesium antacids or supplements while on this medication.
Drug interaction:
LumefantrineAdditive QTc-prolongation may occur. Concomitant therapy should be avoided.
AnisindioneAzithromycin may increase the anticoagulant effect of anisindione by increasing its serum concentration.
DicumarolAzithromycin may increase the anticoagulant effect of dicumarol by increasing its serum concentration.
VorinostatAdditive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
ZuclopenthixolAdditive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
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