| Compound Information | SONAR Target prediction |
| Name: | DIRITHROMYCIN |
| Unique Identifier: | SPE01504144 |
| MolClass: | Checkout models in ver1.5 and ver1.0 |
| Molecular Formula: | |
| Molecular Weight: | 756.454 g/mol |
| X log p: | -2.064 (online calculus) |
| Lipinksi Failures | 2 |
| TPSA | 103.38 |
| Hydrogen Bond Donor Count: | 0 |
| Hydrogen Bond Acceptors Count: | 16 |
| Rotatable Bond Count: | 12 |
| Canonical Smiles: | CCC1OC(=O)C(C)C(OC2CC(C)(OC)C(O)C(C)O2)C(C)C(OC2OC(C)CC(C2O)N(C)C)C(C) (O)CC(C)C2NC(COCCOC)OC(C2C)C1(C)O |
| Source: | semisynthetic |
| Reference: | Drugs 61: 443 (2001) |
| Therapeutics: | antibacterial |
| Generic_name: | Dirithromycin |
| Chemical_iupac_name: | 9-(4-dimethylamino-3-hydroxy-6-methyl-oxan-2-yl)oxy-3-ethyl-2,10-dihydroxy-7-(5-hydr oxy-4-methoxy-4,6-dimethyl-oxan-2-yl)oxy-15-(2-methoxyethoxymethyl)-2,6,8,10,12,17-h examethyl-4,16-dioxa-14-azabicyclo[11.3.1]heptadecan-5-one |
| Drug_type: | Approved Drug |
| Pharmgkb_id: | PA449368 |
| Drugbank_id: | APRD00931 |
| H2o_solubility: | Poor |
| Logp: | 2.833 |
| Cas_registry_number: | 62013-04-1 |
| Drug_category: | Anti-infectives; Macrolides; ATC:J01FA13 |
| 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. |
| 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: Staphylococcus aureus (methicillin-susceptible strains only), Streptococcus pneumoniae, Streptococcus pyogenes, Haemophilus influenzae, Legionella pneumophila, Moraxella catarrhalis, and Mycoplasma pneumoniae. |
| Mechanism_of_action: | 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. |
| Organisms_affected: | Enteric bacteria and other eubacteria |
| Found: 205 nonactive as graph: single | with analogs | [1] << Back 1 2 3 4 5 6 7 8 9 10 Next >> [205] |
| Species: | 4932 |
| Condition: | BY4743 |
| Replicates: | 2 |
| Raw OD Value: r im | 1.0080±0 |
| Normalized OD Score: sc h | 0.9902±0 |
| Z-Score: | 0.3781±0 |
| p-Value: | 0.705362 |
| Z-Factor: | -15.7718 |
| Fitness Defect: | 0.349 |
| Bioactivity Statement: | Nonactive |
| ps |
| DBLink | Rows returned: 7 | 1 2 Next >> |
| 462481 | (2R,3R,6R,7S,9R,10R,12R,13S,15R,17S)-9-(4-dimethylamino-3-hydroxy-6-methyl-oxan-2-yl)oxy-3-ethyl-2,10-di hydroxy-7-(5-hydroxy-4-methoxy-4,6-dimethyl-oxan-2-yl)oxy-15-(2-methoxyethoxymethyl)-2,6,8,10,12,17-hexa methyl-4,16-dioxa-14-azabicyclo[11.3.1]heptadecan-5-one |
| 4580358 | 9-(4-dimethylamino-3-hydroxy-6-methyl-oxan-2-yl)oxy-3-ethyl-2,10-dihydroxy-7-(5-hydroxy-4-methoxy-4,6-di methyl-oxan-2-yl)oxy-15-(2-methoxyethoxymethyl)-2,6,8,10,12,17-hexamethyl-4,16-dioxa-14-azabicyclo[11.3. 1]heptadecan-5-one |
| 5464388 | (2R,3R,6R,7S,8S,9R,10R,12R,13S,15R,17S)-9-[(2S,3R,4S,6R)-4-dimethylamino-3-hydroxy-6-methyl-oxan-2-yl]ox y-3-ethyl-2,10-dihydroxy-7-[(2S,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-oxan-2-yl]oxy-15-(2-methoxyet hoxymethyl)-2,6,8,10,12,17-hexamethyl-4,16-dioxa-14-azabicyclo[11.3.1]heptadecan-5-one |
| 6473883 | (1R,2R,3R,6R,7S,8S,9R,10R,12R,13S,15R,17S)-9-[(2S,3R,4S,6R)-4-dimethylamino-3-hydroxy-6-methyl-oxan-2-yl ]oxy-3-ethyl-2,10-dihydroxy-7-[(2S,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-oxan-2-yl]oxy-15-(2-methox yethoxymethyl)-2,6,8,10,12,17-hexamethyl-4,16-dioxa-14-azabicyclo[11.3.1]heptadecan-5-one |
| 6604422 | (1R,2R,3S,6R,7R,8S,9S,10R,12S,13S,15S,17R)-9-[(2S,3S,4R,6S)-4-dimethylamino-3-hydroxy-6-methyl-oxan-2-yl ]oxy-3-ethyl-2,10-dihydroxy-7-[(2R,4S,5R,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-oxan-2-yl]oxy-15-(2-methox yethoxymethyl)-2,6,8,10,12,17-hexamethyl-4,16-dioxa-14-azabicyclo[11.3.1]heptadecan-5-one |
| 6713946 | (2R,3S,6R,7R,8R,9R,10S,12R,13S,15S,17S)-9-[(2S,3R,4S,6R)-4-dimethylamino-3-hydroxy-6-methyl-oxan-2-yl]ox y-3-ethyl-2,10-dihydroxy-7-[(2S,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-oxan-2-yl]oxy-15-(2-methoxyet hoxymethyl)-2,6,8,10,12,17-hexamethyl-4,16-dioxa-14-azabicyclo[11.3.1]heptadecan-5-one |
| internal high similarity DBLink | Rows returned: 0 |
| nonactive | Cluster 14145 | Additional Members: 11 | Rows returned: 10 | 1 2 Next >> |
| Prest923 | 0.320754716981132 |
| SPE01503276 | 0.264705882352941 |
| Prest1046 | 0.264705882352941 |
| SPE01500279 | 0.221052631578947 |
| SPE01503679 | 0.206521739130435 |
| SPE01501176 | 0.195652173913043 |
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