Basic information
- Standard SMILES
NCC[C@H](O)C(=O)N[C@@H]1C[C@H](N)[C@@H](O[C@H]2O[C@H](CN)CC[C@H]2N)[C@H](O)[C@H]1O[C@H]1O[C@H](CO)[C@@H](O)[C@H](N)[C@H]1O- InChIKey
MKKYBZZTJQGVCD-XTCKQBCOSA-N- Molecular formula
- C22H44N6O10
- Average molar mass
- 552.6 g/mol
- Monoisotopic mass
- 552.31189161
Overview
Arbekacin is a kanamycin that is kanamycin B bearing an N-(2S)-4-amino-2-hydroxybutyryl group on the aminocyclitol ring. It has a role as an antimicrobial agent, an antibacterial agent, an antibacterial drug and a protein synthesis inhibitor. It is a member of kanamycins and an aminoglycoside. It is functionally related to a kanamycin B.
Names & identifiers
- Preferred name
- Arbekacin
- IUPAC
- (2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxybutanamide
- English name
- Arbekacin
- Molecular formula
- C22H44N6O10
- Molecular weight
- 552.62
Names & synonyms
Show more names
Database identifiers
- CAS
51025-85-5- PubChem CID
- 68682
- DTXSID
DTXSID8048319- ChEMBL
CHEMBL426926- ChEBI
CHEBI:37922- UNII
- G7V6SLI20L
- Nikkaji
- J33.173B
Properties
Computed structural properties
- XLogP
- -6.8
- Topological polar surface area
- 297 Ų
- Hydrogen bond donors
- 11
- Hydrogen bond acceptors
- 15
- Rotatable bonds
- 10
- Heavy atoms
- 38
- Formal charge
- 0
- Complexity
- 757
Experimental & physicochemical properties
Physicochemical properties
- Boiling point
- 904 · 904.0±65.0 °C(Predicted)
- Density
- 1.47 · 1.47±0.1 g/cm3(Predicted)
- pka
- 13.07 · 13.07±0.70(Predicted)
- CAS DataBase Reference
- 51025 · 51025-85-5(CAS DataBase Reference)
- FDA UNII
- 7 V6SLI20L · G7V6SLI20L
- ATC code
- 1 GB12 · J01GB12
Safety & regulation
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Arbekacin
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Chemistry & industry
Pharmacology
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Pharmacodynamics
Arbekacin is an aminoglycoside. Aminoglycosides function by binding to bacterial 30S ribosomal subunits, causing t-RNA misreads, and preventing the production of proteins. Anaerobes are less susceptible to aminoglycosides because they do not spend as much energy as aerobes on taking up chemicals like aminoglycosides. Aminoglycosides are useful primarily in infections involving aerobic, gram-negative bacteria, such as Pseudomonas, Acinetobacter, and Enterobacter.
Mechanism of Action
Arbekacin irreversibly binds bacterial 30S and 16S ribosomal subunits inhibiting protein synthesis. Arbekacin binds to 4 nucleotides of the 16S subunit and 1 amino acid of protein S12 to interfere with the decoding site around nucleotide 1400 in the 16S subunit. Interference with the decoding site interferes with its interaction with the wobble base of tRNA. This hindered interaction causes mRNA to be misread and the incorrect amino acids are inserted into protein. These error filled proteins are not able to function or may even be toxic.
Applications
DescriptionArbekacin is a semi-synthetic derivative of dibekacin useful in the treatment of bacterial infections. This aminoglycoside is active against a broad spectrum of bacteria, including some of the gentamycin-, kanamycin-, and tobramycin-resistant pathogens. Compared to amikacin and dibekacin, ototoxicity is reportedly milder.
UsesArbekacin exhibits strong antibacterial activity against kanamycin, gentamicin, and amikacin-resistant bacteria. It is used for sepsis and pneumonia caused by susceptible bacteria.
Upstream & downstream products
Upstream raw materials
Suppliers32 total
Additional notes
DefinitionChEBI: A kanamycin that is kanamycin B bearing an N-(2S)-4-amino-2-hydroxybutyryl group on the aminocyclitol ring.
Related reactions
No reaction records under the current filter.
Linked notes
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