Repositioning Candidate Details

Candidate ID: R0344
Source ID: DB00954
Source Type: experimental
Compound Type: small molecule
Compound Name: Dirithromycin
Synonyms: (9S)-9-deoxo-11-deoxy-9,11-(imino((1R)-2-(2-methoxyethoxy)ethylidene)oxy)erythromycin; Dirithromycin
Molecular Formula: C42H78N2O14
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)[C@@H]2N[C@@H](COCCOC)O[C@H]([C@H]2C)[C@]1(C)O
Structure:
DrugBank Description: Dirithromycin is a macrolide glycopeptide antibiotic used to treat many different types of bacterial infections, such as bronchitis, pneumonia, tonsillitis, and even skin infections.
CAS Number: 62013-04-1
Molecular Weight: 835.086
DrugBank Indication: For the treatment of the following mild-to-moderate infections caused by susceptible strains of microorganisms: acute bacterial exacerbations of chronic bronchitis, secondary bacterial infection of acute bronchitis, community-acquired pneumonia, pharyngitis/tonsilitis, and uncomplicated skin and skin structure infections.
DrugBank Pharmacology: Dirithromycin is a pro-drug which is converted non-enzymatically during intestinal absorption into the microbiologically active moiety erythromycylamine. Erythromycylamine exerts its activity by binding to the 50S ribosomal subunits of susceptible mircoorganisms resulting in inhibition of protein synthesis. Dirithromycin/erythromycylamine has been shown to be active against most strains of the following microorganisms both in vitro and in clinical infections: <i>Staphylococcus aureus</i> (methicillin-susceptible strains only), <i>Streptococcus pneumoniae</i>, <i>Streptococcus pyogenes</i>, <i>Haemophilus influenzae</i>, <i>Legionella pneumophila</i>, <i>Moraxella catarrhalis</i>, and <i>Mycoplasma pneumoniae</i>.
DrugBank MoA: Dirithromycin prevents bacteria from growing, by interfering with their protein synthesis. Dirithromycin binds to the 50S subunit of the 70S bacterial ribosome, and thus inhibits the translocation of peptides. Dirithromycin has over 10 times higher affinity to the subunit 50S than erythromycin. In addition, dirithromycin binds simultaneously in to two domains of 23S RNA of the ribosomal subunit 50S, where older macrolides bind only in one. Dirithromycin can also inhibit the formation of ribosomal subunits 50S and 30S.
Targets: 23S ribosomal RNA inhibitor
Inclusion Criteria: Indication associated