13-01148. p-(Benzylsulfonamido)benzoic Acid [Archived]

Nomenclature

CAS number: 536-95-8
4-[[(Phenylmethyl)sulfonyl]amino]benzoic acid; p-α-toluenesulfonamidobenzoic acid; 4′-carboxyphenylmethanesulfonanilide; Carinamide; Caronamide.
C14H13NO4S; mol wt 291.32.
C 57.72%, H 4.50%, N 4.81%, O 21.97%, S 11.01%.

Description and references

Prepn: GB 666546 (1952 to Sharp & Dohme). Toxicity study: Beyer et al., J. Pharmacol. Exp. Ther. 91, 263 (1947).

Chemical structure

Properties

Crystals, mp 229-230°. uv max (0.1N NaOH): 280-281 nm. Moderately sol in alcohol, acetone, propylene glycol. Very slightly sol in water, carbon tetrachloride, chloroform, benzene. Both the mono- and disodium salts are very sol in water. Aq solns may be prepared by dissolving the acid in an equivalent amount of sodium carbonate or sodium hydroxide soln. It is relatively stable to hydrolysis with acid or base. LD50 in mice (g/kg): 2.45 orally; in mice, dogs, rabbits (g/kg): 1.405, 1.575, 1.32 i.v. (Beyer).

Therapeutic Category

Adjunct in penicillin therapy.

Status

This monograph has been retired and is no longer subject to revision or update.