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Arbekacin

Catalog No. DB06696 Name DrugBank
CAS Number 51025-85-5 Website http://www.ualberta.ca/
M. F. C22H44N6O10 Telephone (780) 492-3111
M. W. 552.61896 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 4434

SYNONYMS

IUPAC name
4-amino-N-(5-amino-2-{[4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[3-amino-6-(aminomethyl)oxan-2-yl]oxy}-3-hydroxycyclohexyl)-2-hydroxybutanamide
IUPAC Traditional name
4-amino-N-(5-amino-2-{[4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[3-amino-6-(aminomethyl)oxan-2-yl]oxy}-3-hydroxycyclohexyl)-2-hydroxybutanamide
Synonyms
Arbekacine
Arbekacina
Haberacin
Habekacin
Arbekacinum

DATABASE IDS

CAS Number 51025-85-5

PROPERTIES

DETAILS

Description (English)
Item Information
Drug Groups approved
Description 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.
Indication Arbekacin is used for the short term treatment of multi-resistant bacterial infections, such as methicillin-resistant Staphylococcus aureus (MRSA).
Pharmacology 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.
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
Absorption Aminoglycosides are not well absorbed from the gastrointestinal tract. Their absorption is markedly improved by parenteral administration.
Half Life 3 hours
Protein Binding 3-12%
References
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]
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]
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]
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":http://aac.asm.org/cgi/content/full/44/7/1925
External Links
Wikipedia

REFERENCES

  • 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
  • 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
  • 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
  • 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":http://aac.asm.org/cgi/content/full/44/7/1925