ChemicalBook > CAS DataBase List > 4-(AMINOMETHYL)BENZENESULFONAMIDE

4-(AMINOMETHYL)BENZENESULFONAMIDE

CAS No.138-39-6
Chemical Name:4-(AMINOMETHYL)BENZENESULFONAMIDE
CBNumber:CB7347830
Molecular Formula:C7H10N2O2S
Formula Weight:186.23
MOL File:138-39-6.mol

4-(AMINOMETHYL)BENZENESULFONAMIDE Property

Melting point 177-178℃ (decomposition)
Boiling point 382.0±44.0 °C(Predicted)
Density 1.345±0.06 g/cm3(Predicted)
storage temp. 2-8°C
solubility DMSO (Slightly), Methanol (Slightly)
form Solid
pka 10.16±0.10(Predicted)
color Light Beige to Beige
EWG's Food Scores 1
FDA UNII 58447S8P4L

Safety

HazardClass :IRRITANT

NFPA 704:

	0
2		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H302-H315-H319-H332-H335
Precautionary statements P280-P305+P351+P338-P310

4-(AMINOMETHYL)BENZENESULFONAMIDE Chemical Properties,Usage,Production

Originator Sulfamylon,Winthrop,US,1949
Uses antibacterial
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.