Investigational Drug Details

Drug ID: D025
Drug Name: Azithromycin
Synonyms: Azithromycin
Type: Chemical drug
DrugBank ID: DB00207
DrugBank Description: Azithromycin is a broad-spectrum macrolide antibiotic with a long half-life and a high degree of tissue penetration . It was initially approved by the FDA in 1991 . It is primarily used for the treatment of respiratory, enteric and genitourinary infections and may be used instead of other macrolides for some sexually transmitted and enteric infections. It is structurally related to erythromycin . Azithromycin is a part of the _azalide_ subclass of macrolides, and contains a 15-membered ring, with a methyl-substituted nitrogen instead of a carbonyl group at the 9a position on the aglycone ring, which allows for the prevention of its metabolism. This differentiates azithromycin from other types of macrolides . In March 2020, a small study was funded by the French government to investigate the treatment of COVID-19 with a combination of azithromycin and the anti-malaria drug . The results were positive, all patients taking the combination were virologically cured within 6 days of treatment, however, larger studies are required.
PubChem ID: 447043
CasNo: 83905-01-5
Repositioning for NAFLD: Yes
SMILES: O([C@@H]1[C@@H](C)[C@H](O[C@H]2C[C@](OC)(C)[C@H]([C@@H](O2)C)O)[C@@H](C)C(=O)O[C@H](CC)[C@@]([C@@H]([C@H](N(C[C@@H](C[C@@]1(C)O)C)C)C)O)(C)O)[C@H]1[C@H](O)[C@@H](N(C)C)C[C@H](O1)C
Structure:
InChiKey: MQTOSJVFKKJCRP-BICOPXKESA-N
Molecular Weight: 748.996
DrugBank Targets: 23S ribosomal RNA inhibitor; Protein-arginine deiminase type-4 inhibitor
DrugBank MoA: In order to replicate, bacteria require a specific process of protein synthesis, enabled by ribosomal proteins . Azithromycin binds to the 23S rRNA of the bacterial 50S ribosomal subunit. It stops bacterial protein synthesis by inhibiting the transpeptidation/translocation step of protein synthesis and by inhibiting the assembly of the 50S ribosomal subunit , . This results in the control of various bacterial infections , . The strong affinity of macrolides, including azithromycin, for bacterial ribosomes, is consistent with their broad‐spectrum antibacterial activities . Azithromycin is highly stable at a low pH, giving it a longer serum half-life and increasing its concentrations in tissues compared to erythromycin .
DrugBank Pharmacology: Macrolides stop bacterial growth by inhibiting protein synthesis and translation, treating bacterial infections . Azithromycin has additional immunomodulatory effects and has been used in chronic respiratory inflammatory diseases for this purpose .
DrugBank Indication: Azithromycin should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria in order to prevent the development antimicrobial resistance and maintain the efficacy of azithromycin . Azithromycin is indicated for the treatment of patients with mild to moderate infections caused by susceptible strains of the microorganisms listed in the specific conditions below. Recommended dosages, duration of therapy and considerations for various patient populations may vary among these infections. Refer to the FDA label and "Indications" section of this drug entry for detailed information . **Adults**: Acute bacterial exacerbations of chronic obstructive pulmonary disease due to _Haemophilus influenzae_, _Moraxella catarrhalis_ or _Streptococcus pneumoniae_ Acute bacterial sinusitis due to _Haemophilus influenzae_, _Moraxella catarrhalis_ or _Streptococcus pneumoniae_ Community-acquired pneumonia due to _Chlamydophila pneumoniae_, _Haemophilus influenzae_, _Mycoplasma pneumoniae_ or _Streptococcus pneumoniae_ in patients appropriate for oral therapy Pharyngitis/tonsillitis caused by _Streptococcus pyogenes_ as an alternative to first-line therapy in individuals who cannot use first-line therapy. Uncomplicated skin and skin structure infections due to _Staphylococcus aureus_, _Streptococcus pyogenes_, or _Streptococcus agalactiae_. Abscesses usually require surgical drainage. Urethritis and cervicitis due to _Chlamydia trachomatis_ or _Neisseria gonorrhoeae_. Genital ulcer disease in men due to _Haemophilus ducreyi_ (chancroid). Due to the small number of women included in clinical trials, the efficacy of azithromycin in the treatment of chancroid in women has not been established. **Pediatric Patients** Acute otitis media caused by _Haemophilus influenzae_, _Moraxella catarrhalis_ or _Streptococcus pneumoniae_ Community-acquired pneumonia due to _Chlamydophila pneumoniae_, _Haemophilus influenzae_, _Mycoplasma pneumoniae_ or _Streptococcus pneumoniae_ in patients appropriate for oral therapy. Pharyngitis/tonsillitis caused by _Streptococcus pyogenes_ as an alternative to first-line therapy in individuals who cannot use first-line therapy.
Targets: --
Therapeutic Category: --
Clinical Trial Progress: Phase 2 completed (NCT01876108)
Latest Progress: Under clinical trials

Trial ID Source ID Phases Status Study Results Start Date Last Update Posted
L0116 NCT01876108 Phase 2 Completed No Results Available July 2012 July 8, 2013 Details
L0926 JPRN-UMIN000009265 Phase 3 Not Recruiting No Results Available 10/11/2012 2 April 2019 Details

Target ID Target Name GENE Action Class UniProtKB ID Entry Name

Strategy ID Strategy Synonyms Related Targets Related Drugs
S05 Anti-inflammatory inflammatory Bile acid; TNF-a inhibitor; Dual PPAR-α and -δ agonists; Toll-Like Receptor; (TLR)-4 antagonist; Caspase inhibitor; ASK-1 inhibitor Ursodeoxycholic Acid; Pentoxifylline; Elafibranor; JKB-121; Emricasan; Selonsertib; Details

Article ID PMID Source Title
A02768 34250613 J Clin Periodontol Elimination of Porphyromonas gingivalis inhibits liver fibrosis and inflammation in NASH. Details
A37867 12911686 J Clin Pharm Ther Is oral azithromycin effective for the treatment of cyclosporine-induced gingival hyperplasia in cardiac transplant recipients? Details