Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C22H44N6O10 |
| Molecular Weight | 552.619 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 14 / 14 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
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
InChI
InChIKey=MKKYBZZTJQGVCD-XTCKQBCOSA-N
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
| Molecular Formula | C22H44N6O10 |
| Molecular Weight | 552.619 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 14 / 14 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27104010 | https://www.ncbi.nlm.nih.gov/pubmed/25298740 | http://adisinsight.springer.com/drugs/800038442 | http://adis.springer.com/drugs/800038522
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27104010 | https://www.ncbi.nlm.nih.gov/pubmed/25298740 | http://adisinsight.springer.com/drugs/800038442 | http://adis.springer.com/drugs/800038522
Arbekacin is a broad-spectrum aminoglycoside used to treat methicillin-resistant Staphylococcus aureus (MRSA). Arbekacin has antibacterial activities against high-level gentamicin-resistant Enterococci, multidrug-resistant Pseudomonas aeruginosa, and Acinetobacter baumannii et al. In a cell-free system, habekacin (arbekacin) interfered with polypeptide synthesis, caused codon misreading, and inhibited translocation of N-acetylphenylalanyl-tRNA from the acceptor site to the donor site on ribosomes. Arbekacin bound to both 50S and 30S ribosomal subunits. Arbekacin has been approved as an injectable formulation in Japan since 1990, under the trade name Habekacin, for the treatment of patients with pneumonia and sepsis caused by MRSA. Meiji Seika Pharma is developing an inhaled aerosol formulation of arbekacin for the treatment of hospital-acquired bacterial pneumonia and ventilator-associated bacterial pneumonia. Nobelpharma is developing an intravenous formulation of arbekacin sulfate, known as nonsense readthrough compound or NPC 14, for the treatment of Duchenne muscular dystrophy.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2363135 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | HABEKACIN Approved UseArbekacin is a broad-spectrum aminoglycoside used to treat methicillin-resistant Staphylococcus aureus (MRSA) Launch Date1989 |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Evaluation of the clinical application of cystatin C, a new marker of the glomerular filtration rate, for the initial dose-setting of arbekacin. | 2008-06 |
|
| Population pharmacokinetics of arbekacin in burn patients. | 2008-06 |
|
| Influences of dosage regimen and co-administration of low-molecular weight proteins and basic peptides on renal accumulation of arbekacin in mice. | 2008-03 |
|
| [Analysis of factors in selecting anti-methicillin-resistant Staphylococcus aureus drugs by doctors]. | 2008-01 |
|
| Prediction of aminoglycoside response against methicillin-resistant Staphylococcus aureus infection in burn patients by artificial neural network modeling. | 2008-01 |
|
| Microbiological and clinical study of methicillin-resistant Staphylococcus aureus (MRSA) carrying VraS mutation: changes in susceptibility to glycopeptides and clinical significance. | 2008-01 |
|
| History and evolution of antibiotic resistance in coagulase-negative staphylococci: Susceptibility profiles of new anti-staphylococcal agents. | 2007-12 |
|
| Susceptibilities of healthcare- and community-associated methicillin-resistant staphylococci to the novel des-F(6)-quinolone DX-619. | 2007-12 |
|
| Effect of varying the 4''-position of arbekacin derivatives on antibacterial activity against MRSA and Pseudomonas aeruginosa. | 2007-11-15 |
|
| Impact of reduced vancomycin susceptibility on the therapeutic outcome of MRSA bloodstream infections. | 2007-10-30 |
|
| [In vitro activity of arbekacin against clinical isolates of Staphylococcus species and gram-negative bacilli]. | 2007-08 |
|
| Synthesis and antibacterial activity of 5-deoxy-5-episubstituted arbekacin derivatives. | 2007-07-01 |
|
| Conspicuous endoscopic appearance of ventriculitis caused by coagulase-negative staphylococci. | 2007-06 |
|
| Relationship between the usage of carbapenem antibiotics and the incidence of imipenem-resistant Pseudomonas aeruginosa. | 2007-06 |
|
| The bactericidal effects of anti-MRSA agents with rifampicin and sulfamethoxazole-trimethoprim against intracellular phagocytized MRSA. | 2007-06 |
|
| [Appropriate usage of antibiotics by therapeutic drug monitoring]. | 2007-06 |
|
| 16S rRNA methylase-producing, gram-negative pathogens, Japan. | 2007-04 |
|
| Biosynthesis of butirosin: transfer and deprotection of the unique amino acid side chain. | 2007-04 |
|
| Trends in the gentamicin and arbekacin susceptibility of methicillin-resistant Staphylococcus aureus and the genes encoding aminoglycoside-modifying enzymes. | 2007-04 |
|
| [Appropriate use of anti-MRSA drugs (discussion)]. | 2007-02 |
|
| Clinical features of head and neck cancer patients with methicillin-resistant Staphylococcus aureus. | 2007-02 |
|
| Synthesis and antibacterial activity of novel neamine derivatives. | 2006-12-15 |
|
| Comparative evaluation of the in vitro antimycobacterial activities of six aminoglycoside antibiotics using an agar dilution method. | 2006-12 |
|
| Dissemination of 16S rRNA methylase-mediated highly amikacin-resistant isolates of Klebsiella pneumoniae and Acinetobacter baumannii in Korea. | 2006-11 |
|
| In vitro activity effects of combinations of cephalothin, dicloxacillin, imipenem, vancomycin and amikacin against methicillin-resistant Staphylococcus spp. strains. | 2006-10-12 |
|
| [Surveillance on Pseudomonas aeruginosa isolated in Gifu prefecture (2004)]. | 2006-10 |
|
| [Susceptibilities of bacteria isolated from patients with lower respiratory infectious diseases to antibiotics (2004)]. | 2006-10 |
|
| [Comparative studies on activities of antimicrobial agents against causative organisms isolated from patients with urinary tract infections (2004). III. Secular changes in susceptibility]. | 2006-08 |
|
| Coagulase-negative staphylococcal infections in the neonate and child: an update. | 2006-07 |
|
| A review of daptomycin for injection (Cubicin) in the treatment of complicated skin and skin structure infections. | 2006-06 |
|
| [Comparative studies on activities of antimicrobial agents against causative organisms isolated from patients with urinary tract infections (2004). I. Susceptibility distribution]. | 2006-06 |
|
| Trends of arbekacin-resistant MRSA strains in Japanese hospitals (1979 to 2000). | 2006-04 |
|
| Synergy of arbekacin-based combinations against vancomycin hetero-intermediate Staphylococcus aureus. | 2006-04 |
|
| Synergistic effect of [10]-gingerol and aminoglycosides against vancomycin-resistant enterococci (VRE). | 2006-03 |
|
| [Antimicrobial susceptibilities of organisms isolated from patients with urinary tract infections in 2002]. | 2006-02 |
|
| Nasopharyngeal decolonization of methicillin-resistant Staphylococcus aureus can reduce PEG peristomal wound infection. | 2006-02 |
|
| Combined effects of panipenem and aminoglycosides on methicillin-resistant Staphylococcus aureus and Pseudomonas aeruginosa in vitro. | 2005-10 |
|
| Inhibitory effect of antimicrobial agents and anisodamine on the staphylococcal superantigenic toxin-induced overproduction of proinflammatory cytokines by human peripheral blood mononuclear cells. | 2005-08 |
|
| Factors influencing neonatal therapeutic effect of anti-MRSA drugs. | 2005-07 |
|
| [Susceptibilities of bacteria isolated from patients with lower respiratory infectious diseases to antibiotics (2003)]. | 2005-06 |
|
| Global spread of multiple aminoglycoside resistance genes. | 2005-06 |
|
| [Combination effect of pazufloxacin and anti-mrsa drugs against beta-lactam antibiotic induced vancomycin-resistant MRSA (BIVR)]. | 2005-02 |
|
| Synergistic effect of fosfomycin and arbekacin on a methicillin-resistant Staphylococcus aureus-induced biofilm in a rat model. | 2005-01 |
|
| Dosage regimen of arbekacin for methicillin-resistant Staphylococcus aureus infection in newborns and infants. | 2004-12 |
|
| Phenotypic and genotypic aminoglycoside resistance in blood culture isolates of coagulase-negative staphylococci from a single neonatal intensive care unit, 1989-2000. | 2004-11 |
|
| Effect of arbekacin on a methicillin-resistant Staphylococcus aureus-induced biofilm in a rat model. | 2004-10 |
|
| Characterization of a bifunctional aminoglycoside-modifying enzyme with novel substrate specificity and its gene from a clinical isolate of methicillin-resistant Staphylococcus aureus with high arbekacin resistance. | 2004-10 |
|
| Clinical glycopeptide-intermediate staphylococci tested against arbekacin, daptomycin, and tigecycline. | 2004-10 |
|
| [In vitro indirect pathogenesis of Pseudomonas aeruginosa against anti MRSA chemotherapy]. | 2004-09 |
|
| [Bacterial interaction and indirect pathogenesis of Pseudomonas aeruginosa at the growth of MRSA]. | 2004-09 |
Sample Use Guides
The recommend initial dose of arbekacin at 5-6 mg/kg or higher and the dosage regimen should be adjusted to achieve C (peak) at 10-15 μg/mL or higher in the treatment of patients with pneumonia or sepsis caused by methicillin-resistant Staphylococcus aureus.
Route of Administration:
Intravenous
| Substance Class |
Chemical
Created
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| Record UNII |
G7V6SLI20L
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Validated (UNII)
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C2363
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ACTIVE MOIETY |
