Repositioning Candidate Details
| Candidate ID: | R0610 |
| Source ID: | DB04626 |
| Source Type: | experimental; vet_approved |
| Compound Type: | small molecule |
| Compound Name: | Apramycin |
| Synonyms: | 4-O-((8R)-2-amino-8-O-(4-amino-4-deoxy-α-D-glucopyranosyl)-2,3,7-trideoxy-7-(methylamino)-D-glycero-α-D-allo-octodialdo-1,5:8,4-dipyranos-1-yl)-2-deoxy-D-streptamine; 4-O-(3α-amino-6α-((4-amino-4-deoxy-α-D-glucopyranosyl)oxy)-2,3,4,5aβ,6,7,8,8aα-octahydro-8β-hydroxy-7β-(methylamino)pyrano(3,2-b)pyran-2α-yl)-2-deoxy-D-streptamine; Apramycin; Nebramycin II |
| Molecular Formula: | C21H41N5O11 |
| SMILES: | CN[C@H]1[C@@H](O)[C@H]2O[C@H](O[C@@H]3[C@@H](N)C[C@@H](N)[C@H](O)[C@H]3O)[C@H](N)C[C@@H]2O[C@@H]1O[C@H]1O[C@H](CO)[C@@H](N)[C@H](O)[C@H]1O |
| Structure: |
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| DrugBank Description: | Apramycin is an aminoglycoside antibiotic and has a bactericidal action against many gram-negative bacteria. Apramycin is a structurally unique antibiotic that contains a bicyclic sugar moiety and a monosubstituted deoxystreptamine. It is not approved for use in humans. |
| CAS Number: | 37321-09-8 |
| Molecular Weight: | 539.5771 |
| DrugBank Indication: | For the treatment of bacterial infections in animals. |
| DrugBank Pharmacology: | -- |
| DrugBank MoA: | Apramycin stands out among aminoglycosides for its mechanism of action which is based on blocking translocation and its ability to bind also to the eukaryotic decoding site despite differences in key residues required for apramycin recognition by the bacterial target. The drug binds in the deep groove of the RNA which forms a continuously stacked helix comprising non-canonical C.A and G.A base pairs and a bulged-out adenine. The binding mode of apramycin at the human decoding-site RNA is distinct from aminoglycoside recognition of the bacterial target, suggesting a molecular basis for the actions of apramycin in eukaryotes and bacteria. |
| Targets: | 16S ribosomal RNA |
| Inclusion Criteria: | Indication associated |
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