Kanamycin

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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Kanamycin
Kanamycin A.svg
Kanamycin ball-and-stick.png
Systematic (IUPAC) name
2-(aminomethyl)- 6-[4,6-diamino-3- [4-amino-3,5-dihydroxy-6-(hydroxymethyl) tetrahydropyran-2-yl]oxy- 2-hydroxy- cyclohexoxy]- tetrahydropyran- 3,4,5-triol
Clinical data
AHFS/Drugs.com monograph
Pregnancy cat. D
Legal status  ?
Routes Oral, intravenous, intramuscular
Pharmacokinetic data
Bioavailability very low after oral delivery
Metabolism Unknown
Half-life 2 hours 30 minutes
Excretion Urine (as unchanged drug)
Identifiers
CAS number 59-01-8 YesY
ATC code A07AA08 J01GB04 S01AA24
PubChem CID 6032
DrugBank DB01172
ChemSpider 5810 YesY
UNII RUC37XUP2P YesY
ChEBI CHEBI:17630 YesY
ChEMBL CHEMBL1384 YesY
Chemical data
Formula C18H36N4O11 
Mol. mass 484.499
 YesY (what is this?)  (verify)

Kanamycin (also known as kanamycin A) is an aminoglycoside bacteriocidal antibiotic, available in oral, intravenous, and intramuscular forms, and used to treat a wide variety of infections. Kanamycin is isolated from the bacterium Streptomyces kanamyceticus[1] and its most commonly used form is kanamycin sulfate.