1528. Butirosin
Nomenclature
Description and references
Aminoglycosidic antibiotic complex obtained from fermentation filtrates of mucoid strains of Bacillus circulans (NRRL B-3312 and B-3313). Consists of two components, butirosin A (80-85%) and butirosin B (15-20%), isomers which differ only in the configuration at one carbon atom in the pentose moiety. Prepn: P. W. K. Woo et al., DE 1914527; eidem, US 3541078 (1969, 1970 both to Parke, Davis). Isoln and characterization: Dion et al., Antimicrob. Agents Chemother. 2, 84 (1972). Structures: Woo et al., Tetrahedron Lett. 1971, 2617, 2621, 2625. Activity: Howells et al., Antimicrob. Agents Chemother. 2, 79 (1972); Heifetz et al., ibid. 89. Synthesis of butirosin B: Ikeda et al., J. Antibiot. 25, 741 (1972); Akita et al., ibid. 26, 365 (1973). Proposed biosynthetic pathway to the butirosins: K. Takeda et al., ibid. 31, 250 (1978).
Derivative
Butirosin sulfate dihydrate.Nomenclature
Properties
No sharp mp, dec ≈225°. [α]D25 +29° (c = 2 in water). pKa′ (water): 5.5, 7.2, 8.5, 9.4. Very sol in water; moderately sol in methanol; slightly sol in ethanol. LD50 i.v. in mice: 450-500 mg/kg (Howells).Derivative
Butirosin A.Nomenclature
Properties
White, amorphous solid, melts with dec over wide range, beginning at ≈149°. [α]D25 +26° (c = 1.46 in water). pKa′ (water): 5.6, 7.3, 8.7, 9.8.Derivative
Butirosin B.Nomenclature
Properties
Occurs as a dihydrate, melts over wide range beginning at 146°. [α]D25 +33° (c = 1.5 in water). pKa′ (water): 5.3, 7.1, 8.6, 9.8.Therapeutic Category
Antibacterial.
Keywords
Antibacterial (Antibiotics); Aminoglycosides