RT Journal Article
SR Electronic
T1 Isolation, Characterization, and Synthesis of an Immunoregulatory Metabolite of Niridazole: 1-Thiocarbamoyl-2-Imidazolidinone
JF Molecular Pharmacology
JO Mol Pharmacol
FD American Society for Pharmacology and Experimental Therapeutics
SP 313
OP 319
VO 18
IS 2
A1 JAMES W. TRACY
A1 EDWARD H. FAIRCHILD
A1 SAMUEL V. LUCAS
A1 LESLIE T. WEBSTER, JR.
YR 1980
UL http://molpharm.aspetjournals.org/content/18/2/313.abstract
AB An immunoactive substance, called niridazole immunoregulatory factor (NIF), has been isolated in chromotographically pure form from the urine of patients treated with the antihelminthic drug, niridazole. The isolate was shown to be a single compound which displayed ultraviolet, infrared, proton magnetic resonance, and mass spectral properties consistent with the structure, 1-thiocarbamoyl-2-imidazolidinone, a previously unreported metabolite of niridazole. The structural assignment was confirmed by chemical synthesis of 1-thiocarbamoyl-2-imidazolidinone from 2-chloroethylisocyanate and thiourea. Both the isolated and the synthetic compounds had identical spectral characteristics and suppressed delayed contact hypersensitivity of mice to 2,4-dinitrofluorobenzene at an optimal dose range of 10-10 to 10-11 g/kg.