Investigational Drug Details
| Drug ID: | D055 |
| Drug Name: | Azithromycin |
| Synonyms: | |
| Type: | small molecule |
| DrugBank ID: | DB00207 |
| DrugBank Description: | Azithromycin is a broad-spectrum macrolide antibiotic with a long half-life and a high degree of tissue penetration [A174172]. It was initially approved by the FDA in 1991 [A174175]. 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 [A174169]. Azithromycin [9-deoxo-9a-aza-9a-methyl-9a-homoerythromycin] 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 [A174175]. |
| PubChem ID: | 447043 |
| CasNo: | 83905-01-5 |
| Repositioning for NAFLD: | Yes |
| SMILES: | CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C)(O)C[C@@H](C)CN(C)[C@H](C)[C@@H](O)[C@]1(C)O |
| Structure: |
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| InChiKey: | MQTOSJVFKKJCRP-BICOPXKESA-N |
| Molecular Weight: | 748.9845 |
| DrugBank Targets: | 23S ribosomal RNA; Protein-arginine deiminase type-4 |
| DrugBank MoA: | In order to replicate, bacteria require a specific process of protein synthesis, enabled by ribosomal proteins [A6505]. 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 [FDA label], [A14179]. This results in the control of various bacterial infections [A174193], [FDA label]. The strong affinity of macrolides, including azithromycin, for bacterial ribosomes, is consistent with their broadâspectrum antibacterial activities [A174193]. Azithromycin is highly stable at a low pH, giving it a longer serum half-life and increasing its concentrations in tissues compared to erythromycin [A174175]. |
| DrugBank Pharmacology: | Macrolides stop bacterial growth by inhibiting protein synthesis and translation, treating bacterial infections [A174175]. Azithromycin has additional immunomodulatory effects and has been used in chronic respiratory inflammatory diseases for this purpose [A174172]. |
| 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 [FDA label]. 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 [FDA label]. **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: | |
| Latest Progress: |
| Trial ID | Source ID | Phases | Status | Study Results | Start Date | Last Update Posted | |
|---|---|---|---|---|---|---|---|
| L6849 | NCT01972893 | PHASE1 | COMPLETED | NO | 2011-02 | 2013-10-31 | Details |
| L6900 | NCT00393705 | PHASE4 | COMPLETED | YES | 2006-10 | 2010-07-20 | Details |
| Target ID | Target Name | GENE | Action | Class | UniProtKB ID | Entry Name | |
|---|---|---|---|---|---|---|---|
| T03 | Angiotensin-converting enzyme | ACE | INHIBITOR | Target is a single protein chain | P12821 | ACE_HUMAN | Details |
| T47 | Sialin | SLC17A5 | Target is a single protein chain | Q9NRA2 | SLC17A5_HUMAN | Details | |
| T06 | Sulfonylurea receptor 1 | ABCC8 | Target is a single protein chain | Q09428 | ABCC8_HUMAN | Details | |
| T15 | Steryl-sulfatase | STS | INHIBITOR | Hydrolase | P08842 | STS_HUMAN | Details |
| Strategy ID | Strategy | Synonyms | Related Targets | Related Drugs | |
|---|---|---|---|---|---|
| S11 | digital therapeutics | Percutaneous left atrial appendage occlusion (LAAO); Antiplatelet therapy; inhibition of PAPP-A; gut microbiota modulation; innovative absorption-based approach; application of the effective antimicrobial agents against Aeromonas under the supervision of infectious doctors; percutaneous catheter-directed treatment approach; application of adequate drug policy measures; appropriate antibiotics; Digital therapeutics; digitalis; preventing inappropriate ESA use | C3; CD20 | oral anticoagulation; antiplatelet therapy; a monoclonal antibody that blocks the proteolytic activity of PAPP-A against IGFBP4; synbiotic; cephalosporins; thrombolytics; rosuvastatin; warfarin; ""appropriate antibiotics""; ""high-dose steroid therapy""; antimetabolics; anti-CD20; antiarrhythmic agents; digitalis; direct oral anticoagulants; antidepressants; Erythropoiesis-stimulating agents; originator ESA; biosimilars | Details |
| Article ID | PMID | Source | Title |
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