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Arbekacin

Arbekacin Structure
CAS No.
51025-85-5
Chemical Name:
Arbekacin
Synonyms
1665RB;AHB-DKB;AHB[1KB;HABA-DKB;haberacin;habekacin;ARBEKACIN;Decontasin;Blubatosine;Arbekacin USP/EP/BP
CBNumber:
CB7347991
Molecular Formula:
C22H44N6O10
Molecular Weight:
552.62
MOL File:
51025-85-5.mol
MSDS File:
SDS
Modify Date:
2022/12/21 16:56:50

Arbekacin Properties

Boiling point 904.0±65.0 °C(Predicted)
Density 1.47±0.1 g/cm3(Predicted)
pka 13.07±0.70(Predicted)
CAS DataBase Reference 51025-85-5(CAS DataBase Reference)

Arbekacin Chemical Properties,Uses,Production

Description

Arbekacin is a semi-synthetic derivative of dibekacin useful in the treatment of bacterial infections. This aminoglycoside is active against a broad spectrum of bacteria, including some of the gentamycin-, kanamycin-, and tobramycin-resistant pathogens. Compared to amikacin and dibekacin, ototoxicity is reportedly milder.

Definition

ChEBI: A kanamycin that is kanamycin B bearing an N-(2S)-4-amino-2-hydroxybutyryl group on the aminocyclitol ring.

Antimicrobial activity

The 1-N-(4-amino-2-hydroxybutyryl) derivative of dibekacin, to which it bears the same relation as amikacin bears to kanamycin A. Supplied as the sulfate.
Activity and stability to aminoglycoside-modifying enzymes are comparable with those of amikacin. It is active against many strains of methicillin-resistant Staph. aureus, either alone or in combination with β-lactam or other agents. Synergy with ampicillin has been observed for high-level gentamicin- and vancomycin-resistant enterococci.
A 3 mg/kg intravenous dose achieved a peak concentration of c. 8 mg/L after 1 h. The plasma half-life is about 2 h and protein binding 3–12%.
About 85% of the dose can be recovered from urine over 48 h. It is retained in renal failure, but moderately well removed by hemodialysis with a plasma half-life of 2–4 h. Peak concentrations of 10.9 mg/L and trough concentrations of 1.7 mg/L have been reported in patients treated for MRSA infection where Cmax:MIC ratios of >25 and AUC:MIC ratios of >186 were associated with improved cure rates, and both Cmin and AUC were associated with the incidence of nephrotoxicity.
Toxicity and side effects are typical of the aminoglycoside class. It is used in severe infection cause by susceptible microorganisms, but is not widely available.

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ARBEKACIN (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 (2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[(2R,3R,6S)-3-amino-6-(aminomethyl)tetrahydropyran-2-yl]oxy-2-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methylol-tetrahydropyran-2-yl]oxy-3-hydroxy-cyclohexyl]-2-hydroxy-butyramide (2S)-N-[(1R,2S,3S,4R,5S)-4-[(2R,3R,6S)-6-(aminomethyl)-3-azanyl-oxan-2-yl]oxy-5-azanyl-2-[(2S,3R,4S,5S,6R)-4-azanyl-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxy-cyclohexyl]-4-azanyl-2-hydroxy-butanamide (s)-oxy-1-oxobutyl)-2-deoxy 3,4,6-tetradeoxy-alpha-d-erythro-hexopyranosyl-(1-4))-n(sup1)-(4-amino-2-hydr habekacin haberacin (S)-O-3-Amino-3-deoxy-α-D-glucopyranosyl-(1→6)-O-[2,6-diamino-。2,3,4,6-tetradeoxy-α-D-erythro-hexopyranosyl-(1→4)-]- N^<1>^-(4-amino-2-hydroxy-1-oxobutyl)-2-deoxy-D-streptarnine 1665RB 1-N-[(S)-4-Amino-2-hydroxybutyryl]-3',4'-dideoxykanamycin B AHB-DKB D-Streptamine, O-3-amino-3-deoxy-α-D-glucopyranosyl-(1→6)-O-[2,6-diamino-2,3,4,6-tetradeoxy-α-D-erythro-hexopyranosyl-(1→4)]-N1-[(2S)-4-amino-2-hydroxy-1-oxobutyl]-2-deoxy- HABA-DKB (2S)-4-Amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-[(2R,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxy-cyclohexyl]-2-hydroxy-butanamide AHB[1KB Blubatosine Decontasin 4-O-[3-Amino-3-deoxy-α-D-glucopyranosyl]-6-O-[2,6-diamino-2,3,4,6-tetradeoxy-α-D-erythro-hexopyranosyl]-N'-[(2S)-4-amino-2-hydroxy-1-oxobutyl]-2-deoxy-L-streptamine 6-O-(3-Amino-3-deoxy-α-D-glucopyranosyl)-4-O-(2,6-diamino-2,3,4,6-tetradeoxy-α-D-erythro-hexopyranosyl)-N1-[(S)-4-amino-2-hydroxybutyryl]-2-deoxy-D-streptamine 2-[3-(4-bromophenyl)-2-cyclohexylimino-4-oxo-5-thiazolidinyl]acetic acid Arbekacin USP/EP/BP 51025-85-5 C22H44N6O10