Mafenide acetate Chemical Properties

Melting point:

151-152°C

storage temp. 

Inert atmosphere,2-8°C

solubility 

DMSO: soluble1mg/mL

form 

Solid

color 

white

CAS DataBase Reference

13009-99-9(CAS DataBase Reference)

Safety Information

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2935904000

Toxicity

LD50 in rats, mice (mg/kg): 2040, 1580 i.v. (Skulan, Hoppe)

MSDS

• Language:English Provider:SigmaAldrich

Mafenide acetate Usage And Synthesis

Chemical Properties

Crystalline Solid

Originator

Sulfamylon,Winthrop,US,1949

Uses

Antibacterial.

Definition

ChEBI: Mafenide acetate is a carboxylic acid.

Manufacturing Process

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.

brand name

Sulfamylon (Sterling Winthrop).

Therapeutic Function

Antibacterial

General Description

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.

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