5649. Mafenide

Nomenclature

CAS number: 138-39-6
4-(Aminomethyl)benzenesulfonamide; α-amino-p-toluenesulfonamide; p-(aminomethyl)benzenesulfonamide; 4-homosulfanilamide; maphenide; Marfanil; Mesudrin; Mesudin; Sulfamylon (Winthrop); Homosulfamine; Ambamide; Neofamid; Septicid; Emilene; Homonal (SS Pharm.); Paramenyl.
C7H10N2O2S; mol wt 186.23.
C 45.15%, H 5.41%, N 15.04%, O 17.18%, S 17.22%.

Description and references

Prepn: Miller et al., J. Am. Chem. Soc. 62, 2099 (1940); Klarer, US 2288531 (1942 to Winthrop); Bergeim, Braker, J. Am. Chem. Soc. 66, 1459 (1944); Kusami et al., J. Pharm. Soc. Jpn. 64, no. 9a, 51 (1944); Komokina et al., J. Appl. Chem. USSR 21, 681 (1948); Angyal, Jenkin, Aust. J. Sci. Res. 3A, 461 (1950). Toxicity study: T. W. Skulan, J. O. Hoppe, Life Sci. 5, 2279 (1966). Comprehensive description: A. K. Dash, S. Saha, Anal. Profiles Drug Subs. Excip. 24, 277-305 (1996).

Chemical structure

Properties

Crystals from alc, mp 151-152°. Sol in dil alkali, acid.

Derivative

Hydrochloride.

Nomenclature

CAS number: 138-37-4
C7H10N2O2S.HCl; mol wt 222.69.
C 37.75%, H 4.98%, N 12.58%, O 14.37%, S 14.40%, Cl 15.92%.

Properties

Crystals from 95% alc, mp 256°. Neutral in soln. LD50 in rats, mice (mg/kg): 1170, 900 i.v. (Skulan, Hoppe).

Derivative

Acetate.

Nomenclature

CAS number: 13009-99-9
Mafatate (Torii); Mefamide (Bayer).
C7H10N2O2S.C2H4O2; mol wt 246.28.
C 43.89%, H 5.73%, N 11.37%, O 25.99%, S 13.02%.

Properties

mp 151-152°. Freely sol in water, methanol. LD50 in rats, mice (mg/kg): 2040, 1580 i.v. (Skulan, Hoppe).

Derivative

Propionate.

Nomenclature

CAS number: 12001-72-8
Sulfomyl.
C7H10N2O2S.C3H6O2; mol wt 260.31.
C 46.14%, H 6.20%, N 10.76%, O 24.59%, S 12.32%.

Properties

Crystals, mp 158°. Readily sol in water.

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Synthetic); Sulfonamides