Sulfamylon,Winthrop,US,1949
ChEBI: Mafenide acetate is a carboxylic acid.
For the preparation of mafenide 50 g of acetylbenzylamine are introduced
while stirring into 150 cc of chlorosulfonic acid, whereby the temperature is
kept below 40°C by external cooling. After several hours' storing at ordinary temperature the mixture is heated for 1 hour in the boiling water-bath and
after cooling, poured on to ice. Thereupon the 4-acetylaminoethylbenzenesulfonic acid chloride precipitates at first in an oily form, but solidifies
after short stirring to crystals. The product sucked off and washed with cold
water is introduced into a 10% aqueous ammonia solution. Thereby
dissolution takes place while heating and after a short time the 4-
acetylaminomethyl-benzenesulfonic acid amide precipitates in a crystalline
form. After heating to 70°C for 30 minutes the solution is cooled, filtered with
suction and washed out. The product is obtained when recrystallized from
water or dilute alcohol in colorless crystals melting at 177%. It is readily
soluble in warm water, extremely readily soluble in dilute sodium hydroxide
solution.
Sulfamylon (Sterling Winthrop).
4-(Aminomethyl)benzenesulfonamide acetate (Sulfamylon)is a homologue of the sulfanilamide molecule. It is not atrue sulfanilamide-type compound, as it is not inhibited byPABA. Its antibacterial action involves a mechanism thatdiffers from that of true sulfanilamide-type compounds.
This compound is particularly effective against Clostridiumwelchii in topical application and was used duringWorld War II by the German army for prophylaxis ofwounds. It is not effective orally. It is currently used aloneor with antibiotics in the treatment of slow-healing, infectedwounds.
Some patients treated for burns with large quantities ofthis drug have developed metabolic acidosis. To overcomethis adverse effect, a series of new organic salts was prepared. The acetate in an ointment base proved to be themost efficacious.
