| Chemical Information | |
| Antiviral agent ID | DrugRepV_0727 | |
| Antiviral agent name | Dirithromycin |  |
| IUPAC Name | (1S,2R,4R,5R,6S,7S,8R,11R,12R,13R,15R,17S)-5-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-11-ethyl-4,12-dihydroxy-7-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-15-(2-methoxyethoxymethyl)-2,4,6,8,12,17-hexamethyl-10,14-dioxa-16-azabicyclo[11.3.1]heptadecan-9-one |  |
| SMILES (canonical) | CCC1C(C2C(C(C(CC(C(C(C(C(C(=O)O1)C)OC3CC(C(C(O3)C)O)(C)OC)C)OC4C(C(CC(O4)C)N(C)C)O)(C)O)C)NC(O2)COCCOC)C)(C)O | |
| SMILES (isomeric) | CC[C@@H]1[C@@]([C@H]2[C@H]([C@H]([C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]3C[C@@]([C@H]([C@@H](O3)C)O)(C)OC)C)O[C@H]4[C@@H]([C@H](C[C@H](O4)C)N(C)C)O)(C)O)C)N[C@H](O2)COCCOC)C)(C)O | |
| Molecular Formula | C42H78N2O14 | |
| Molecular Weight (g/mol) | 835.09 | |
| InChl | InChI=1S/C42H78N2O14/c1-15-29-42(10,49)37-24(4)32(43-30(56-37)21-52-17-16-50-13)22(2)19-40(8,48)36(58-39-33(45)28(44(11)12)18-23(3)53-39)25(5)34(26(6)38(47)55-29)57-31-20-41(9,51-14)35(46)27(7)54-31/h22-37,39,43,45-46,48-49H,15-21H2,1-14H3/t22-,23-,24+,25+,26-,27+,28+,29-,30-,31+,32+,33-,34+,35+,36-,37-,39+,40-,41-,42-/m1/s1 | |
| Common Name | Dirithromycin | |
| Synonyms | (9S)-9-deoxo-11-deoxy-9,11-(imino((1R)-2-(2-methoxyethoxy)ethylidene)oxy)erythromycin | LY-237216 | Dirithromycine | Dynabac | |
| Structural Information | |
 |
|
| Clinical Information | |
|
Category | Antiinfectives For Systemic Use
| |
|
Primary Indication (Clinical trial phases) | Approved
|  |
| Biological Information | |
|
Primary Indication (Disease Category) | Infectious Disease
| |
|
Primary Indication (Disease) | Bacterial infections
| |
|
Secondary Indication | Ebola virus (EBOV) NA ma-EBOV |   |
|
Secondary Indication (Approaches) | Experimental | |
| Secondary Indication (Methods) | In-vivo | |
|
Secondary Indication (Model system) [cell lines/ animal models] | Balb/c
| |
|
Secondary Indication (Mode of viral infection) | Intraperitoneal
| |
|
Secondary Indication (Viral titer) | 1000 PFU
| |
|
Secondary Indication (Mode of drug delivery) | Intraperitoneal
| |
|
Secondary Indication (Time of drug delivery) | Post infection (0 day)
| |
|
Secondary Indication (Duration of drug delivery) | 7 days
| |
|
Secondary Indication (Drug concentration) | 50 mg/kg/ twice a day
| |
|
Secondary Indication (Change) | No significant effect
| |
|
Secondary Indication (Type of Inhibition) | Percentage survival [ NA NA ] | |
|
Reference | Madrid PB, Chopra S, Manger ID, Gilfillan L, Keepers TR, Shurtleff AC, Green CE, Iyer LV, Dilks HH,.A systematic screen of FDA-approved drugs for inhibitors of biological threat agents..PLoS One. 2013;8(4):e60579. doi: 10.1371/journal.pone.0060579. Epub 2013 Apr 5. PMID:23577127
|  |
|
Comment | 1012 FDA-approved drugs for off-label broad-spectrum efficacy against Bacillus anthracis; Francisella tularensis; Coxiella burnetii; and Ebola, Marburg, and Lassa fever viruses using in vitro cell culture assays. Multiple virus-specific inhibitors were identified, the most noteworthy antiviral compound identified was chloroquine, which disrupted entry and replication of two or more viruses in vitro and protected mice against Ebola virus challenge in vivo. The feasibility of repurposing existing drugs to face novel threats is demonstrated and this represents the first effort to apply this approach to high containment bacteria and viruses.
| |