Arbekacin

Arbekacin

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Arbekacin
Category Antibiotics
Catalog number BBF-00560
CAS 51025-85-5
Molecular Weight 552.31
Molecular Formula C22H44N6O10
Purity >98%

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Description

Arbekacin(INN) is a semisynthetic aminoglycoside antibiotic. It is primarily used for the treatment of infections caused by multi-resistant bacteria including methicillin-resistant Staphylococcus aureus(MRSA).

Specification

Related CAS 104931-87-5 (sulfate)
Storage Store at -20°C
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
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
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

Properties

Appearance Colorless Crystal
Antibiotic Activity Spectrum bacteria
Density 1.47 g/cm3
Solubility Soluble in DMSO

Reference Reading

1.[Susceptibilities of bacteria isolated from patients with lower respiratory infectious diseases to antibacterial agents (2010)].
Goto H, Iwasaki M. Jpn J Antibiot. 2015 Apr;68(2):85-104.
From October 2010 to September 2011, we collected the specimen from 361 patients with lower respiratory tract infections in 16 institutions in Japan, and investigated the susceptibilities of isolated bacteria to various antibacterial agents and patients' characteristics. All of 399 strains that were isolated from specimen (mainly from sputum) and assumed to be bacteria causing in infection, were examined. The isolated bacteria were: Staphylococcus aureus 70, Streptococcus pneumoniae 65, Haemophilus influenzae 72, Pseudomonas aeruginosa (non-mucoid) 47, P. aeruginosa (mucoid) 14, Klebsiella pneumoniae 30, and Moraxella catarrhalis 39. Of 70 S. aureus strains, those with 2 μg/mL or less of MIC of oxacillin (methicillin-susceptible S. aureus: MSSA) and those with 4 μg/mL or more of MIC of oxacillin (methicillin-resistant S. aureus: MRSA) were 45 (64.3%) and 25 (35.7%) strains, respectively. Against MSSA, imipenem had the most potent antibacterial activity and inhibited the growth of all strains at 0.
2.Anti-inflammatory effects of linezolid on carrageenan-induced paw edema in rats.
Matsumoto K1, Obara S2, Kuroda Y2, Kizu J2. J Infect Chemother. 2015 Dec;21(12):889-91. doi: 10.1016/j.jiac.2015.08.004. Epub 2015 Sep 9.
The immunomodulatory activity of linezolid has recently been reported using in vitro experimental models. However, the anti-inflammatory activity of linezolid has not yet been demonstrated using in vivo experimental models. Therefore, the aim of the present study was to demonstrate the anti-inflammatory activity of linezolid and other anti-MRSA agents using the carrageenan-induced rat paw edema model. The pretreatment with 50 mg/kg linezolid significantly suppressed edema rates, compared with control (5% glucose), with edema rates at 0.5 and 3 h after the administration of carrageenan being 17.3 ± 3.5 and 30.8 ± 3.0%, respectively. On the other hand, edema rates were not suppressed by the pretreatments with 50 mg/kg vancomycin, teicoplanin, arbekacin, and daptomycin. Furthermore, we demonstrated that linezolid exhibited anti-inflammatory activity in a concentration-dependent manner. These effects were observed at linezolid concentrations that are achievable in human serum with conventional dosing.
3.Phenotypic and genomic comparisons of highly vancomycin-resistant Staphylococcus aureus strains developed from multiple clinical MRSA strains by in vitro mutagenesis.
Ishii K1, Tabuchi F1, Matsuo M2, Tatsuno K3, Sato T3, Okazaki M4, Hamamoto H1, Matsumoto Y1, Kaito C1, Aoyagi T5, Hiramatsu K2, Kaku M5, Moriya K3, Sekimizu K1. Sci Rep. 2015 Nov 25;5:17092. doi: 10.1038/srep17092.
The development of vancomycin (VCM) resistance in Staphylococcus aureus threatens global health. Studies of the VCM-resistance mechanism and alternative therapeutic strategies are urgently needed. We mutagenized S. aureus laboratory strains and methicillin-resistant S. aureus (MRSA) with ethyl methanesulfonate, and isolated mutants that exhibited high resistance to VCM (minimum inhibitory concentration = 32 μg/ml). These VCM-resistant strains were sensitive to linezolid and rifampicin, and partly to arbekacin and daptomycin. Beta-lactams had synergistic effects with VCM against these mutants. VCM-resistant strains exhibited a 2-fold increase in the cell wall thickness. Several genes were commonly mutated among the highly VCM-resistant mutants. These findings suggest that MRSA has a potential to develop high VCM resistance with cell wall thickening by the accumulation of mutations.
4.Clinical Evaluation of Pharmacist Interventions in Patients Treated with Anti-methicillin-Resistant Staphylococcus aureus Agents in a Hematological Ward.
Okada N1, Fushitani S, Azuma M, Nakamura S, Nakamura T, Teraoka K, Watanabe H, Abe M, Kawazoe K, Ishizawa K. Biol Pharm Bull. 2016;39(2):295-300. doi: 10.1248/bpb.b15-00774.
The therapeutic effects of anti-methicillin-resistant Staphylococcus aureus (MRSA) agents, vancomycin (VCM), teicoplanin (TEIC), and arbekacin (ABK), depend on their concentrations in blood. Therefore, therapeutic drug monitoring (TDM) is important when these antibiotics are used. In the hematological ward at Tokushima University Hospital, pharmacists have ordered the measurement of blood VCM, TEIC, and ABK concentrations to promote the use of TDM in accordance with an agreed protocol since 2013. Moreover, the infection control team includes several medical disciplines and has advised on the optimal treatment using VCM, TEIC, and ABK since 2013. This study aimed to investigate the clinical effectiveness of these pharmacist interventions. We retrospectively studied 145 cases in which patients were treated with VCM, TEIC, or ABK between January 2012 and December 2013 in the hematological ward at Tokushima University Hospital. The patients were divided into a control group (71 cases) and an intervention group (74 cases), and their clinical outcomes were compared.

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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