Kanamycin
Structural Formula Vector Image
Title: Kanamycin
CAS Registry Number: 8063-07-8
Literature References: Antibiotic complex produced by Streptomyces kanamyceticus Okami & Umezawa from Japanese soil: Umezawa et al., J. Antibiot. 10A, 181 (1957); US 2931798 (1960). Comprised of three components, kanamycin A, the major component (usually designated as kanamycin) and kanamycins B and C, two minor congeners. Isoln and purification of kanamycins A and B and their salts: Johnson et al., and Johnson, Hardcastle, US 2936307 and US 2967177 (1960, 1961 both to Bristol-Myers). Separation process: Rothrock, Putter, US 3032547 (1962 to Merck & Co.). Prepn of kanamycin C: Murase et al., J. Antibiot. 14A, 156 (1961). Studies on kanamycin B: Wakazawa et al., ibid. 180, 187. Structure of kanamycin A: Ogawa et al., ibid. 11A, 169 (1958); Cron et al., J. Am. Chem. Soc. 80, 4741 (1958). Structure of kanamycin B: Ito et al., J. Antibiot. 17A, 189 (1964). Structure of kanamycin C: Murase, ibid. 14A, 367 (1961). Abs config of kanamycin A: Hichens, Rinehart, J. Am. Chem. Soc. 85, 1547 (1963); Umezawa et al., Bull. Chem. Soc. Jpn. 39, 1244 (1966). Crystal structure of kanamycin A: Koyama et al., Tetrahedron Lett. 1968, 1875. Monograph: Ann. N.Y. Acad. Sci. 76, 17-408 (1958). Synthesis of kanamycin A: Umezawa et al., J. Antibiot. 21, 367 (1968); Nakajima et al., Tetrahedron Lett. 1968, 623; Umezawa et al., Bull. Chem. Soc. Jpn. 42, 533 (1969). Synthesis of kanamycin B: eidem, J. Antibiot. 21, 424 (1968); Bull. Chem. Soc. Jpn. 42, 537 (1969). Chemical conversion of kanamycin B to kanamycin C: S. Toda et al., J. Antibiot. 30, 1002 (1977). Synthesis of kanamycin C: Umezawa et al., Bull. Chem. Soc. Jpn. 41, 533 (1968); J. Antibiot. 21, 162 (1968). Effects on protein synthesis: Suzuki et al., ibid. 23, 99 (1970). Toxicity data (kanamycin A sulfate): Zel'tser et al., Antibiotiki 19, 552 (1974). Comprehensive description: P. J. Claes et al., Anal. Profiles Drug Subs. 6, 259-296 (1977).
 
Derivative Type: Kanamycin A
CAS Registry Number: 59-01-8
Additional Names: O-3-Amino-3-deoxy-a-D-glucopyranosyl-(1®6)-O-[6-amino-6-deoxy-a-D-glucopyranosyl-(1®4)]-2-deoxy-D-streptamine
Molecular Formula: C18H36N4O11
Molecular Weight: 484.50
Percent Composition: C 44.62%, H 7.49%, N 11.56%, O 36.32%
Properties: Crystals from methanol + ethanol. [a]D24 +146° (0.1N H2SO4). LD50 i.v. in mice: 583 mg/kg (Wakazawa).
Optical Rotation: [a]D24 +146° (0.1N H2SO4)
Toxicity data: LD50 i.v. in mice: 583 mg/kg (Wakazawa)
 
Derivative Type: Kanamycin A sulfate
CAS Registry Number: 25389-94-0
Trademarks: Cantrex; Cristalomicina; Enterokanacin (Sidus); Kamycine (BMS); Kamynex; Kanacedin; Kanamytrex (Basotherm); Kanasig; Kanatrol (Lusofarmaco); Kanicin; Kannasyn; Kantrex (Apothecon); Klebcil (SKB); Otokalixin; Resistomycin (Bayer); Kanescin (Torlan); Kanaqua (Andromaco)
Properties: (U.S.P. requires that kanamycin sulfate contains not less than 75% kanamycin A on an anhydr basis). Irregular prisms, dec over a wide range above 250°C. Freely sol in water. Practically insol in the common alcohols and nonpolar solvents. LD50 in mice: 20.7 g/kg orally; 1450 mg/kg i.p. (Zel'tser).
Toxicity data: LD50 in mice: 20.7 g/kg orally; 1450 mg/kg i.p. (Zel'tser)
 
Derivative Type: Kanamycin B
CAS Registry Number: 4696-76-8
Additional Names: Bekanamycin; aminodeoxykanamycin
Manufacturers' Codes: NK-1006
Molecular Formula: C18H37N5O10
Molecular Weight: 483.51
Percent Composition: C 44.71%, H 7.71%, N 14.48%, O 33.09%
Properties: Crystals, mp 178-182° (dec). [a]D18 +130° (c = 0.5 in water). [a]D21 +114° (c = 0.98 in water). Sol in water, formamide; slightly sol in chloroform, isopropyl alcohol. Practically insol in the common alcohols and nonpolar solvents. LD50 i.v. in mice: 136 mg/kg (Wakazawa).
Melting point: mp 178-182° (dec)
Optical Rotation: [a]D18 +130° (c = 0.5 in water); [a]D21 +114° (c = 0.98 in water)
Toxicity data: LD50 i.v. in mice: 136 mg/kg (Wakazawa)
 
Derivative Type: Kanamycin B sulfate
CAS Registry Number: 29701-07-3
Trademarks: Coltericin (Quimica Argentia); Kanendomycin (Meiji); Kanendos (Crinos)
Literature References: Pharmacokinetics: F. Di Nola et al., Minerva Med. 70, 1803 (1979).
 
Derivative Type: Kanamycin C
CAS Registry Number: 2280-32-2
Molecular Formula: C18H36N4O11
Molecular Weight: 484.50
Percent Composition: C 44.62%, H 7.49%, N 11.56%, O 36.32%
Properties: Crystals from methanol + ethanol, dec above 270°. [a]D20 +126° (H2O). Sol in water; slightly sol in formamide. Practically insol in the common alcohols and nonpolar solvents.
Optical Rotation: [a]D20 +126° (H2O)
 
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antibacterial.
Keywords: Antibacterial (Antibiotics); Aminoglycosides.

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