Title: Ribostamycin
CAS Registry Number: 25546-65-0
CAS Name: O-2,6-Diamino-2,6-dideoxy-a-D-glucopyranosyl-(1®4)-O-[b-D-ribofuranosyl-(1®5)]-2-deoxy-D-streptamine
Manufacturers' Codes: SF-733 antibiotic
Molecular Formula: C17H34N4O10
Molecular Weight: 454.47
Percent Composition: C 44.93%, H 7.54%, N 12.33%, O 35.20%
Literature References: Aminocyclitol antibiotic belonging to the neomycin, q.v., group of antibiotics. Produced by Streptomyces ribosidificus (formerly called S. thermoflavus). Taxonomy, isoln and toxicity data: T. Shomura et al., J. Antibiot. 23, 155 (1970). Prepn: eidem, DE 1814735 corresp to US 3661892, US 3799842 (1969, 1972, 1974 all to Meiji). Structure: E. Akita et al., J. Antibiot. 23, 173 (1970). Synthesis from neamine, q.v.: Ito et al., Antimicrob. Agents Chemother. 1970, 33; eidem, Agric. Biol. Chem. 34, 980 (1970); V. Kumar, W. A. Remers, J. Org. Chem. 43, 3327 (1978); 46, 4298 (1981). Total synthesis: H. Fukami et al., Tetrahedron Lett. 1976, 545; eidem, Agric. Biol. Chem. 41, 1689 (1977). In vitro antibacterial activity: E. Yourassowsky, M. P. Vander Linden, Arzneim.-Forsch. 26, 184 (1976).
Properties: Colorless needles from methanol, mp 192-195°. Also reported as monohydrate from water-methanol-ethanol, mp 175-180° (dec). [a]D23 +42°. pKa¢ 7.70. Stable in neutral and alkaline solns; slightly unstable in acidic media. Sol in water; slightly sol in methanol. Practically insol in acetone, n-butanol, ethyl acetate, benzene, hexane, ether.
Melting point: mp 192-195°; mp 175-180° (dec)
pKa: pKa¢ 7.70
Optical Rotation: [a]D23 +42°
Derivative Type: Sulfate
CAS Registry Number: 53797-35-6
Trademarks: Ibistacin (IBI); Landamycine (Delalande); Ribostamin (Delalande); Ribomycine (Delalande); Vistamycin (Meiji)
Properties: White or yellowish powder. [a]D20 +39° (c = 1). LD50 i.v. in mice: 225 mg/kg (Shomura).
Optical Rotation: [a]D20 +39° (c = 1)
Toxicity data: LD50 i.v. in mice: 225 mg/kg (Shomura)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); Aminoglycosides. |