Compound ID | 1846

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Arbekacin

Synonym(s): ME1100

Class: Aminoglycoside

Spectrum of activity: Gram-positive & Gram-negative
Details of activity: Inhibits protein synthesis by binding to the 30S subunit of the bacterial ribosome. Active against Gram-positive and Gram-negative bacteria
Description: Semisynthetic, derived from dibekacin. Marketed in Japan for systemic use to treat MRSA infections, developed for inhalation in the US (since 2018)
Institute where first reported: Meiji Seika Pharma
Year first mentioned: 1973
Highest development stage: Phase 1 for inhalation (since 2013)
Development status: Approved, off-patent
Chemical structure(s):
Click here for structure editor
Molecular weight: 552.62
Iso. SMILES: C1C[C@H]([C@H](O[C@@H]1CN)O[C@@H]2[C@H](C[C@H]([C@@H]([C@H]2O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)N)O)NC(=O)[C@H](CCN)O)N)N
InChI Key: MKKYBZZTJQGVCD-XTCKQBCOSA-N
Can. SMILES: C1C[C@H]([C@H](O[C@@H]1CN)O[C@@H]2[C@H](C[C@H]([C@@H]([C@H]2O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)N)O)NC(=O)[C@H](CCN)O)N)N
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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/68682
Guide to Pharmacology: arbekacin
Citations:
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4432132/
  • https://pubmed.ncbi.nlm.nih.gov/4782059/

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