apramycin   Click here for help

GtoPdb Ligand ID: 10760

Synonyms: EBL-1003 | EL-857 | EL857 | nebramycin factor 2 | nebramycin II
PDB Ligand
Comment: Apramycin is an aminoglycoside antibacterial compound that was originally isolated from Streptomyces tenebrarius. The compound has activity against Gram-negative bacteria [2,4].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 16
Hydrogen bond donors 11
Rotatable bonds 6
Topological polar surface area 283.64
Molecular weight 539.28
XLogP -4.99
No. Lipinski's rules broken 2
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Canonical SMILES CN[C@@H]1[C@H](O[C@@H]2[C@@H]([C@@H]1O)O[C@@H]([C@@H](C2)N)O[C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O)N)O[C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)N
Isomeric SMILES CN[C@@H]1[C@H](O[C@@H]2[C@@H]([C@@H]1O)O[C@@H]([C@@H](C2)N)O[C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O)N)O[C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)N
InChI InChI=1S/C21H41N5O11/c1-26-11-14(30)18-8(33-20(11)37-21-16(32)13(29)10(25)9(4-27)34-21)3-7(24)19(36-18)35-17-6(23)2-5(22)12(28)15(17)31/h5-21,26-32H,2-4,22-25H2,1H3/t5-,6+,7-,8+,9-,10-,11+,12+,13+,14-,15-,16-,17-,18+,19+,20-,21-/m1/s1
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Summary of Clinical Use Click here for help
Apramycin is used in veterinary medicine. The drug is not approved for use in humans but has progressed to clinical evaluation [5].
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT05590728 Safety of Intravenous Apramycin in Adults Phase 1 Interventional National Institute of Allergy and Infectious Diseases (NIAID)
NCT04105205 First-In-Human Study of Apramycin Phase 1 Interventional Juvabis AG This first-in-human study, designed to evaluate the safety, tolerability and pharmacokinetics of apramycin in healthy volunteers, has been completed. 3,5