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药品详细

Arbekacin(阿贝卡星)

化学结构式图
中文名
阿贝卡星
英文名
Arbekacin
分子式
C22H44N6O10
化学名
(2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-2-{[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy}-3-hydroxycyclohexyl]-2-hydroxybutanamide
分子量
Average: 552.619
Monoisotopic: 552.311891658
CAS号
51025-85-5
ATC分类
J01G 未知
药物类型
small molecule
阶段
approved
商品名
同义名
基本介绍

An semisynthetic aminoglycoside antibiotic. Often used for treatment of multi-resistant bacterial infection such as methicillin-resistant Staphylococcus aureus (MRSA).
Amikacin is also nephrotoxic and ototoxic.

生产厂家
    封装厂家
    参考
    Synthesis Reference Not Available
    General Reference
    1. Inoue M, Nonoyama M, Okamoto R, Ida T: Antimicrobial activity of arbekacin, a new aminoglycoside antibiotic, against methicillin-resistant Staphylococcus aureus. Drugs Exp Clin Res. 1994;20(6):233-9. Pubmed
    2. Morikawa K, Nonaka M, Yoshikawa Y, Torii I: Synergistic effect of fosfomycin and arbekacin on a methicillin-resistant Staphylococcus aureus-induced biofilm in a rat model. Int J Antimicrob Agents. 2005 Jan;25(1):44-50. Pubmed
    3. Doi Y, Yokoyama K, Yamane K, Wachino J, Shibata N, Yagi T, Shibayama K, Kato H, Arakawa Y.Plasmid-mediated 16S rRNA methylase in Serratia marcescens conferring high-level resistance to aminoglycosides.Antimicrob Agents Chemother. 2004 Feb;48(2):491-6.Pubmed
    4. Akins RL, and Rybak MJ.In Vitro Activities of Daptomycin, Arbekacin, Vancomycin, and Gentamicin Alone and/or in Combination against Glycopeptide Intermediate-Resistant Staphylococcus aureus in an Infection Model. Antimicrobial Agents and Chemotherapy.July 2000, p. 1925-1929, Vol. 44, No. 7 Antimicrobial agents and Chemotherapy
    剂型
    规格
    化合物类型
    Type small molecule
    Classes Not Available
    Substructures Not Available
    适应症
    药理
    Indication Arbekacin is used for the short term treatment of multi-resistant bacterial infections, such as methicillin-resistant Staphylococcus aureus (MRSA).
    Pharmacodynamics Aminoglycosides, such as Arbekacin, work by binding to the bacterial 30S ribosomal subunit, causing misreading of t-RNA which consequently, leaves the bacterium unable to synthesize proteins vital to its growth. Energy is needed for aminoglycoside uptake into the bacterial cell. Anaerobes have less energy available for this uptake, so aminoglycosides are less active against anaerobes. Aminoglycosides are useful primarily in infections involving aerobic, gram-negative bacteria, such as Pseudomonas, Acinetobacter, and Enterobacter.
    Mechanism of action Aminoglycosides, such as Arbekacin, inhibit protein synthesis in susceptible bacteria by irreversibly binding to bacterial 30S and 16S ribosomal subunits. Specifically Arbekacin binds to four nucleotides of 16S rRNA and a single amino acid of protein S12. This interferes with decoding site in the vicinity of nucleotide 1400 in 16S rRNA of 30S subunit. This region interacts with the wobble base in the anticodon of tRNA. This leads to misreading of mRNA so incorrect amino acids are inserted into the polypeptide leading to nonfunctional or toxic peptides and the breakup of polysomes into nonfunctional monosomes.
    Absorption Aminoglycosides are not well absorbed from the gastrointestinal tract. Their absorption is markedly improved by parenteral administration.
    Volume of distribution Not Available
    Protein binding 3-12%
    Metabolism
    Not Available
    Route of elimination Not Available
    Half life 3 hours
    Clearance Not Available
    Toxicity Ototoxicity and nephrotoxicity are the most serious adverse effects of aminoglycoside therapy and are more likely to occur in patients with a history of renal impairment or who are receiving other ototoxic and/or nephrotoxic drugs. Normal duration of IM or IV aminoglycoside therapy is 7-10 days. Although a longer duration may be necessary in some cases, toxicity is more likely to occur when aminoglycoside treatment is continued for longer than 10 days.
    Affected organisms
    • Enteric bacteria and other eubacteria
    Pathways Not Available
    理化性质
    Properties
    State solid
    Experimental Properties
    Property Value Source
    melting point 178 Not Available
    Predicted Properties
    Property Value Source
    water solubility 4.10e+01 g/l ALOGPS
    logP -2.9 ALOGPS
    logP -6.9 ChemAxon
    logS -1.1 ALOGPS
    pKa (strongest acidic) 12.49 ChemAxon
    pKa (strongest basic) 9.99 ChemAxon
    physiological charge 5 ChemAxon
    hydrogen acceptor count 15 ChemAxon
    hydrogen donor count 11 ChemAxon
    polar surface area 297.27 ChemAxon
    rotatable bond count 10 ChemAxon
    refractivity 129.08 ChemAxon
    polarizability 56.65 ChemAxon
    药物相互作用
    食物相互作用
    Not Available

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