7754. Probenecid

Nomenclature

CAS number: 57-66-9
4-[(Dipropylamino)sulfonyl]benzoic acid; p-(dipropylsulfamoyl)benzoic acid; p-(dipropylsulfamyl)benzoic acid; Benemid (Merck & Co.); Probecid (Astra); Proben (SCS).
C13H19NO4S; mol wt 285.36.
C 54.72%, H 6.71%, N 4.91%, O 22.43%, S 11.24%.

Description and references

Prepn from p-carboxybenzenesulfonyl chloride and dipropylamine: C. S. Miller, US 2608507 (1952 to Sharp & Dohme). Study of metabolites: Z. H. Israili et al., J. Med. Chem. 15, 709 (1972). Clinical pharmacokinetics: R. F. Cunningham et al., Clin. Pharmacokinet. 6, 135 (1981). Toxicology studies: S. E. McKinney et al., J. Pharmacol. Exp. Ther. 102, 208 (1951); NTP Technical Report 395 (PB92-129584, 1991) 220 pp. Comprehensive description: A. A. Al-Badr, H. A. El-Obeid, Anal. Profiles Drug Subs. 10, 639-663 (1981).

Chemical structure

Properties

Crystals from dilute alcohol, mp 194-196°. uv max (0.1N NaOH): 242.5 nm. pKa 5.8. Slightly bitter taste, pleasant aftertaste. Sol in chloroform, in dil solns of NaOH buffered to pH 7.4. Nearly insol in water.

Derivative

Sodium salt.

Nomenclature

CAS number: 23795-03-1
C13H18NNaO4S; mol wt 307.34.
C 50.80%, H 5.90%, N 4.56%, Na 7.48%, O 20.82%, S 10.43%.

Properties

LD50 in mice (mg/kg): 458 i.v., 1156 s.c., 1666 orally; in rats (mg/kg): 394 i.p., 611 s.c., 1604 orally (McKinney).

Therapeutic Category

Uricosuric.

Keywords

Antigout; Uricosuric