arbekacin   Click here for help

GtoPdb Ligand ID: 7345

Synonyms: arbekacin sulfate | habekacin | ME1100 | NPC-14
Approved drug PDB Ligand
arbekacin is an approved drug
Compound class: Synthetic organic
Comment: Arbekacin is a semisynthetic aminoglycoside antibacterial compound that was originally derived from dibekacin [1]. It has activity against both Gram-positive and Gram-negative bacteria [3].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 16
Hydrogen bond donors 11
Rotatable bonds 11
Topological polar surface area 297.27
Molecular weight 552.31
XLogP -5.86
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES NCCC(C(=O)NC1CC(N)C(C(C1OC1OC(CO)C(C(C1O)N)O)O)OC1OC(CN)CCC1N)O
Isomeric SMILES NCC[C@@H](C(=O)N[C@@H]1C[C@H](N)[C@H]([C@@H]([C@H]1O[C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)N)O)O)O[C@H]1O[C@H](CN)CC[C@H]1N)O
InChI InChI=1S/C22H44N6O10/c23-4-3-12(30)20(34)28-11-5-10(26)18(37-21-9(25)2-1-8(6-24)35-21)17(33)19(11)38-22-16(32)14(27)15(31)13(7-29)36-22/h8-19,21-22,29-33H,1-7,23-27H2,(H,28,34)/t8-,9+,10-,11+,12-,13+,14-,15+,16+,17-,18+,19-,21+,22+/m0/s1
InChI Key MKKYBZZTJQGVCD-XTCKQBCOSA-N
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Summary of Clinical Use Click here for help
Arbekacin is a potent aminoglycoside antibiotic already approved in some countries to treat multidrug-resistant bacteria. An inhalation solution of arbekacin (ME1100) is being developed for the treatment of hospital-acquired and ventilator-associated bacterial pneumonia.

Several aminoglycoside antibiotics, including arbekacin, have been reported to have the ability to promote mRNA translation even in the presence of premature termination codons (PTCs) in mutated genes. In the absence of pharmaceutical intervention, the ribosomal translation process produces truncated, often non-functional protein products. However, in the presence of such compounds the ribosomes 'readthrough' the PTCs, producing increased amounts of full-length, functional protein. This developing pharmaceutical intervention has been termed 'readthrough strategy' and has led to a repurposing effort, with the compound now being evaluated in clinical trial as a treatment for Duchenne muscular dystrophy (DMD), in patients where the inherited genetic mutation causes production of truncated, non-functional dystrophin. Dystrophin is a protein critical for muscle function. For more information regarding current clinical trials testing arbekacin, visit www.clinicaltrials.gov.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Arbekacin promotes ribosomal readthrough of PTCs, thereby increasing transcription of full-length, functional proteins.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT02459158 A Study to Assess the Pharmacokinetic Profile, the Safety, and the Tolerability of ME1100 Inhalation Solution in Patients With Mechanically Ventilated Bacterial Pneumonia Phase 1 Interventional Meiji Seika Pharma Co., Ltd. 2
NCT01918384 Phase II Study of NPC-14 (Arbekacin Sulfate) to Explore Safety, Tolerability, and Efficacy in Duchenne Muscular Dystrophy Phase 2 Interventional Kobe University