770. Arbekacin

Nomenclature

CAS number: 51025-85-5
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-d-streptamine; 1-N-[(S)-4-amino-2-hydroxybutyryl]dibekacin; 1-N-[(S)-4-amino-2-hydroxybutyryl]-3′,4′-dideoxykanamycin B; HBK.
C22H44N6O10; mol wt 552.62.
C 47.82%, H 8.03%, N 15.21%, O 28.95%.

Description and 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).

Chemical structure

Derivative

Sulfate.

Nomenclature

CAS number: 104931-87-5
1665-RB; Habekacin (Meiji Seika).
C22H44N6O10.H2SO4; mol wt 650.70.
C 40.61%, H 7.13%, N 12.92%, O 34.42%, S 4.93%.

Derivative

Dicarbonate.
C24H48N6O16; mol wt 676.67.
C 42.60%, H 7.15%, N 12.42%, O 37.83%.

Properties

Colorless, crystalline powder, mp 178° (dec). [α]D24 +86.8° (c = 0.77 in water). LD50 i.v. in mice: >150 mg/kg (Umezawa, 1978).

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Antibiotics); Aminoglycosides