Arbekacin

Title: Arbekacin
CAS Registry Number: 51025-85-5
CAS Name: O-3-Amino-3-deoxy-a-D-glucopyranosyl-(1®6)-O-[2,6-diamino-2,3,4,6-tetradeoxy-a-D-erythro-hexopyranosyl-(1®4)]-N1-[(2S)-4-amino-2-hydroxy-1-oxobutyl]-2-deoxy-D-streptamine
Additional Names: 1-N-[(S)-4-amino-2-hydroxybutyryl]dibekacin; 1-N-[(S)-4-amino-2-hydroxybutyryl]-3¢,4¢-dideoxykanamycin B; HBK
Molecular Formula: C22H44N6O10
Molecular Weight: 552.62
Percent Composition: C 47.82%, H 8.03%, N 15.21%, O 28.95%
Literature References: Aminoglycoside antibiotic; derivative of kanamycin B, q.v. Prepn and antibacterial activity: S. Kondo et al., J. Antibiot. 26, 412 (1973); H. Umezawa et al., DE 2350169; eidem, US 4107424 (1974, 1978 both to Microbiochem. Res. Found.). Mechanism of action: N. Tanaka et al., Antimicrob. Agents Chemother. 24, 797 (1983); K. Matsunaga et al., J. Antibiot. 37, 596 (1984). Pharmacology: J. Stewens et al., Arzneim.-Forsch. 35, 1440 (1985); M. Kurebe et al., ibid. 36, 1511 (1986). Series of articles on antibacterial activity, pharmacology, pharmacokinetics, and clinical experience: Chemotherapy 34, Suppl. 1, pp 1-670 (1986). Review: Y. Kobayashi et al., Int. J. Antimicrob. Agents 5, 227-230 (1995).
Derivative Type: Sulfate
CAS Registry Number: 104931-87-5
Manufacturers' Codes: 1665-RB
Trademarks: Habekacin (Meiji Seika)
Molecular Formula: C22H44N6O10.H2SO4
Molecular Weight: 650.70
Percent Composition: C 40.61%, H 7.13%, N 12.92%, O 34.42%, S 4.93%
Derivative Type: Dicarbonate
Molecular Formula: C24H48N6O16
Molecular Weight: 676.67
Percent Composition: C 42.60%, H 7.15%, N 12.42%, O 37.83%
Properties: Colorless, crystalline powder, mp 178° (dec). [a]D24 +86.8° (c = 0.77 in water). LD50 i.v. in mice: >150 mg/kg (Umezawa, 1978).
Melting point: mp 178° (dec)
Optical Rotation: [a]D24 +86.8° (c = 0.77 in water)
Toxicity data: LD50 i.v. in mice: >150 mg/kg (Umezawa, 1978)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); Aminoglycosides.
Arborescin Arbutamine Arbutin Ardeparin Areca

Arbekacin
Arbekacin.png
Systematic (IUPAC) name
(2S)-4-amino-N-[(1R,2S,3R,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
Clinical data
AHFS/Drugs.com International Drug Names
Legal status Prescription only
Routes Intramuscular, intravenous
Pharmacokinetic data
Metabolism minimal
Excretion Renal
Identifiers
CAS number 51025-85-5 YesY
ATC code J01GB12
PubChem CID 11398765
DrugBank DB06696
ChemSpider 9573665 YesY
UNII G7V6SLI20L YesY
KEGG D07462 YesY
ChEMBL CHEMBL233430 YesY
Chemical data
Formula C22H44N6O10 
Mol. mass 552.62 g/mol
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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).[1][2] Arbekacin was originally synthesized from dibekacin in 1973. It has been registered and marketed in Japan since 1990 under the trade name Habekacin.[3] Arbekacin is no longer covered by patent and generic versions of the drug are also available under such trade names as Decontasin and Blubatosine.