Gantrisin Acetyl ,Roche ,US ,1954
Sulfisoxazole Acetyl is an antibiotic used in the prevention of infection especially when used in conjunction with erythromycin.
ChEBI: Sulfisoxazole acetyl is a sulfonamide and a member of benzenes.
267 grams (1 mol) of sulfisoxazole were suspended in 400 ml of acetone and
79 grams (1 mol) of dry pyridine at 20-25°C in a round-bottom flask equipped
with a stirrer and thermometer. 132 grams (1 mol) of acetic anhydride were
added within 3 minutes with stirring. The sulfisoxazole dissolved in the
mixture and a clear solution resulted. The temperature rose to 39-40°C. After
stirring for several minutes, the product started to crystallize as a white
crystalline mush. The temperature rose to 42-43°C maintained itself at this
temperature for 15-30 minutes, and then started to drop. Stirring was
continued for 5 hours and the mixture was then allowed to stand for 10 hours.
One liter of 2.5-3.0% ice-cold aqueous ammonia and some fresh ice were
then added while stirring and the crystals were filtered without delay. The
crystals were washed on the filter with 1 liter of ice-cold 1% ammonia and
then with 1 liter of water. The material on the filter was well pressed off,
washed with 200-300 ml of alcohol and dried at 70°C to constant weight. The
N-monoacetyl sulfisoxazole melted at 193-194°C and showed a positive
Bratton-Marshall reaction and a positive Hucknall-Turfat reaction.
The product is in the form of colorless crystals which are somewhat water
repellent. It is insoluble in alkali but is saponified upon standing in alkaline
suspension (3% ammonia). It is soluble in strong acids (20-36% HCl or 10 N
H2SO4) and is rapidly saponified upon standing.
Sulfisoxazole acetyl shares the actions and usesof the parent compound, sulfisoxazole. The acetyl derivativeis tasteless and, therefore, suitable for oral administration, especiallyin liquid preparations. The acetyl compound is splitin the intestinal tract and absorbed as sulfisoxazole; that is, itis a prodrug for sulfisoxazole.
