Originator
Sulfamylon,Winthrop,US,1949
Definition
ChEBI: Mafenide is an aromatic amine.
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
Pharmaceutical Applications
p-Aminomethylbenzene sulfonamide; Sulfamylon.
A topical agent formerly used extensively in burns, especially
for its action in suppressing Ps. aeruginosa. It is rapidly
absorbed through burned skin and is unusual in that it is not neutralized by p-aminobenzoic acid or by tissue exudates.
Disadvantages of its use are local pain and burning, a variety
of allergic reactions including erythema multiforme and
its capacity to inhibit carbonic anhydrase, necessitating careful
observation to detect the development of metabolic acidosis.
Its metabolite, p-carboxybenzene sulfonamide, also
inhibits carbonic anhydrase but has no antibacterial activity.
Mafenide propionate was formerly used in ophthalmic
preparations.
Synthesis
Maphenide, n-(aminomethyl)-benzenesulfamide (33.1.48), is structurally somewhat different from all drugs examined above in that the amino group in the p-position to the
sulfonamide group is distanced from the benzene ring by one methyl group. This drug is synthesized from N-benzylacetamide, subsequent reaction of which with chlorosulfonic acid and
then with ammonia gives 4-(acetamidomethyl)-benzene-sulfonamide (33.1.47). Hydrolyzing
this product with a base gives maphenid.
Synonyms of this drug are marfanil, mezudin, ambamide, septicid, and others.
