ChemDB: Kanamycin Sulfate

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  • Chemical Name: Kanamycin monosulfate (a mixture of kanamycin A, B, and C sulfates)
  • Molecular Formula:
    • Kanamycin A: C₁₈H₃₆N₄O₁₁·H₂SO₄
    • Kanamycin B: C₁₈H₃₇N₅O₁₀·H₂SO₄
  • Molecular Weight:
    • Kanamycin A sulfate: 582.58 g/mol
    • Kanamycin B sulfate: 583.60 g/mol
  • Appearance: White to off-white crystalline powder
  • Solubility:
    • Water: ~50 mg/mL (clear, colorless solution at 20 mg/mL)
    • DMSO: Slightly soluble (~5 mg/mL)
    • Ethanol: Insoluble (<1 mg/mL)
  • Stability:
    • Stable in dry form at room temperature
    • Aqueous solutions stable at pH 2–9 for 24 hours
    • Degrades in strong acids/bases or upon prolonged heating
  • Mechanism of Action: 
    • Primary Target: 30S ribosomal subunit → disrupts protein synthesis
    • Binds irreversibly to the 16S rRNA (A-site) → misreading of mRNA
    • Bactericidal at high concentrations
  • Spectrum of Activity:
    • Gram-negative: Escherichia coli, Klebsiella, Enterobacter, Salmonella
    • Gram-positive: Limited activity (some Staphylococcus strains)
    • Mycobacteria: Mycobacterium tuberculosis (second-line drug)
  • Resistance Mechanisms:
    • Enzymatic modification: Aminoglycoside-modifying enzymes (e.g., aphA, aac, aad genes)
    • Ribosomal mutation: Alterations in 16S rRNA (less common)
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