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

• ChemBase ID: 4434
• Molecular Formular: C22H44N6O10
• Molecular Mass: 552.61896
• Monoisotopic Mass: 552.31189164
• SMILES: C1CC(C(OC1CN)OC1C(CC(C(C1O)OC1C(C(C(C(O1)CO)O)N)O)NC(=O)C(CCN)O)N)N
• Canonical SMILES: NCCC(C(=O)NC1CC(N)C(C(C1OC1OC(CO)C(C(C1O)N)O)O)OC1OC(CN)CCC1N)O
• 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)
• InChIKey: MKKYBZZTJQGVCD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• 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: Habekacin; Haberacin; Arbekacina; Arbekacine; Arbekacinum; Arbekacin

Database IDs

• CAS Number: 51025-85-5
• PubChem SID: 160967866
• PubChem CID: 2226

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.491436
• H Acceptors: 15
• H Donor: 11
• LogD (pH = 5.5): -21.487917
• LogD (pH = 7.4): -15.613873
• Log P: -6.853272
• Molar Refractivity: 129.0835 cm^3
• Polarizability: 54.020226 Å^3
• Polar Surface Area: 297.27 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -2.93
• LOG S: -1.13
• Solubility (Water): 4.10e+01 g/l

DETAILS

DrugBank - DB06696

• 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