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AZITHROMYCIN USP

IUPAC Name: (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one

Molecular Formula: C38H72N2O12

Molecular weight: 749.0 g/mol

CAS No: 83905-01-5

ATC Code: J01FA10

Drug Class: Macrolide antibiotics

General Properties:

Azithromycin belongs to the class of drugs known as macrolide antibiotics. It works by killing bacteria or preventing their growth. However, this medicine will not work for colds, flu, or other virus infections. This medicine is available only with your doctor’s prescription.

Indication:

Azithromycin is a broad-spectrum macrolide antimicrobial and is among the most prescribed antimicrobial drugs in the United States. It is a derivative of erythromycin with greatly enhanced activity against gram-negative bacteria (including Enterobacteriaceae) and provides coverage of many gram-positive organisms.

  • As an inhibitor of bacterial protein synthesis (rather than a peptidoglycan cell-wall inhibitor like beta-lactam agents), azithromycin is effective against many “atypical” bacteria such as chlamydiae (e.g., Chlamydia trachomatis and Chlamydophila psittaci), legionella (i.e., Legionella pneumophila), mycoplasma (e.g., Mycoplasma pneumoniae), and mycobacteria (e.g., Mycobacterium avium).
  • Together with its activity against Streptococcus pneumoniaeHemophilus influenzae, and Moraxella catarrhalis, azithromycin is indicated—and FDA approved—for the treatment of community-acquired pneumonia (CAP).
  • Azithromycin also has approval for use in other upper respiratory infectious processes, including acute otitis media and acute exacerbation of chronic obstructive pulmonary disease (COPD).
  • Additionally, azithromycin has approval for the treatment of pharyngitis caused by Streptococcus pyogenesas an alternative to a beta-lactam agent; skin or skin structure infection due to  pyogenesStreptococcus agalactiae, or Staphylococcus aureus M. avium complex (MAC) infection treatment and prophylaxis for patients with advanced acquired immunodeficiency syndrome (AIDS); and sexually transmitted infections including chlamydia, gonococcal disease, chancroid (caused by Hemophilus ducreyi), and Mycoplasma genitalium.
  • Azithromycin also has efficacy against some protozoal organisms such as Babesia sp.(e.g.,  microti), Plasmodium sp. (i.e., malaria), and Toxoplasma gondii and is sometimes used off-label for the treatment of these parasitic diseases in combination with antiprotozoal drugs (e.g., atovaquone).
  • The role of azithromycin in the treatment of viral infections, including the respiratory syncytial virus and novel coronavirus SARS-CoV-2, is indeterminate.
  • Lastly, azithromycin is also used off-label as long-term prophylaxis for bronchiolitis obliterans (BO) in patients who have undergone lung transplantation.

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