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Ethambutol dihydrochloride

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Ethambutol dihydrochloride Basic information
Ethambutol dihydrochloride Chemical Properties
  • Melting point:198-200°C
  • alpha D25 +7.6° (c = 2 in water)
  • storage temp. 2-8°C
  • solubility H2O: soluble50mg/mL
  • form powder
  • color white
  • optical activity[α]25/D 6.0 to 6.7°, c = 10 in water
  • Water Solubility Slightly soluble in water
  • Merck 14,3720
  • CAS DataBase Reference1070-11-7(CAS DataBase Reference)
Safety Information
MSDS
Ethambutol dihydrochloride Usage And Synthesis
  • Chemical PropertiesWhite Powder
  • OriginatorMyambutol,Lederle,US,1967
  • UsesAntibacterial (tuberculostatic)
  • UsesAntituberculous
  • DefinitionChEBI: The dihydrchloride salt of ethambutol. A bacteriostatic antimycobacterial drug, it is effective against Mycobacterium tuberculosis and some other mycobacteria. It is used in combination with other antituberculous drugs in the treatment of pulm nary and extrapulmonary tuberculosis; resistant strains of M. tuberculosis are readily produced if ethambutol dihydrochloride is used alone.
  • Manufacturing ProcessTo 27 grams (2.55 mols) of 2-amino-1-butanol was added 100 grams (1.0 mol) of ethylene dichloride. The mixture was heated at reflux and in a few minutes, the exothermic reaction required the removal of exterior heating. After 10 minutes, exterior heating was recommenced for an additional 20 minutes. The hot mixture was then treated with 300 ml of methanol and then cautiously with 84 grams (2.1 mols) of sodium hydroxide in 80 ml of water.
    The precipitated sodium chloride was removed by filtration. The excess 2- amino-1-butanol distilled as light yellow oil at 83° to 87°C/13 mm. The viscous residue distilled at 165° to 170°C/0.6 mm as a light yellow oil which tended to solidify in the air condenser; yield, 108 grams.
    Recrystallization by dissolving in 80 ml of hot ethanol, adding about 150 ml of petroleum ether (BP 90° to 100°C) and cooling at 5°C overnight, gave 64 grams of white crystals melting at 128° to 132.5°C. This, on recrystallization from 100 ml of 95% ethanol, gave 35 grams of white crystals melting at 134.5° to 136°C and a second crop of 10 grams melting at 132.5° to 134°C which is the meso base. Its dihydrochloride melts at 202° to 203°C.
    From the ethanolic filtrates upon addition of 130 ml of about 4 N ethanolic hydrochloric acid and cooling, there was obtained 55 grams of white crystals melting at 176.5° to 178°C and a second crop of 10 grams melting at 171.5° to 174.5°C. This is the dl racemate dihydrochloride.
  • brand nameMyambutol (Stat Trade).
  • Therapeutic FunctionAntitubercular
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