Structure via PubChem · Public domain (PubChem)
arbekacin
Sign in to saveAlso known as arbekacin sulfate, NPC-14, ABK, Haberacin, Arbekacinum, Arbekacine, Habekacin
Arbekacin (INN) is a semisynthetic aminoglycoside antibiotic which was derived from kanamycin. It is primarily used for the treatment of infections caused by multi-resistant bacteria including methicillin-resistant Staphylococcus aureus (MRSA). Arbekacin was originally synthesized from dibekacin in 1973 by Hamao Umezawa and collaborators. It has been registered and marketed in Japan since 1990 under the trade name Habekacin. Arbekacin is no longer covered by patent and generic versions of the drug are also available under such trade names as Decontasin and Blubatosine.
Chemical data
- Formula
- C22H44N6O10
- Molecular weight
- 552.6 g/mol
- IUPAC name
- (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
- 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
- InChIKey
- MKKYBZZTJQGVCD-XTCKQBCOSA-N
- XLogP
- -6.8
- Polar surface area
- 297 Ų
- H-bond donors
- 11
- H-bond acceptors
- 15
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
- Indications
- bacterial disease, bacterial pneumonia
via ChEMBL · EBI
Research
475 papers- Clinical Usefulness of Arbekacin.Infection & chemotherapy · 2016
- Evaluation of once-daily dosing and target concentrations in therapeutic drug monitoring for arbekacin: A meta-analysis.Journal of infection and chemotherapy : official journal of the Japan Society of Chemotherapy · 2021
- Kanamycin and its derivative, arbekacin: significance and impact.The Journal of antibiotics · 2018
- Increased Arbekacin Clearance in Patients With Febrile Neutropenia.Therapeutic drug monitoring · 2020
- Arbekacin.International journal of antimicrobial agents · 1995
via PubMed
Wikidata facts
- Subclass of
- aminoglycoside antibiotic
- Mass
- 552.312
- Has use
- medication
Show 8 more facts
- chemical formula
- C₂₂H₄₄N₆O₁₀
- canonical SMILES
- C1CC(C(OC1CN)OC2C(CC(C(C2O)OC3C(C(C(C(O3)CO)O)N)O)NC(=O)C(CCN)O)N)N
- World Health Organisation international non-proprietary name
- arbekacin
- defined daily dose
- 0.2
- NCI Thesaurus ID
- C76145
- isomeric 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]3O[C@H](CO)[C@@H](O)[C@H](N)[C@H]3O
- subject has role
- bactericide
- Commons category
- Arbekacin
Sources (3)
via Wikidata · CC0
~3 min read
Encyclopedic overview
6 sectionsContents
- Pharmacology
- Pharmacodynamics
- Mechanism of action
- Absorption
- Toxicity
- References
Arbekacin (INN) is a semisynthetic aminoglycoside antibiotic which was derived from kanamycin. It is primarily used for the treatment of infections caused by multi-resistant bacteria including methicillin-resistant Staphylococcus aureus (MRSA). Arbekacin was originally synthesized from dibekacin in 1973 by Hamao Umezawa and collaborators. It has been registered and marketed in Japan since 1990 under the trade name Habekacin. Arbekacin is no longer covered by patent and generic versions of the drug are also available under such trade names as Decontasin and Blubatosine.
==Pharmacology== Arbekacin is approved for the treatment of pneumonia and sepsis caused by methicillin-resistant Staphylococcus aureus (MRSA). Because of its synergistic effect with beta-lactams, arbekacin also holds promise as a treatment for multidrug-resistant Gram-negative bacterial infections such as multidrug-resistant Pseudomonas aeruginosa and Acinetobacter baumannii.
Excerpted from Wikipedia’s “arbekacin” article, available under the CC BY-SA 4.0 licence.