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Molecular Pharmacology, Vol 18, 313-319, Copyright © 1980 by the American Society for Pharmacology and Experimental Therapeutics

Isolation, Characterization, and Synthesis of an Immunoregulatory Metabolite of Niridazole: 1-Thiocarbamoyl-2-Imidazolidinone

JAMES W. TRACY 1, EDWARD H. FAIRCHILD 1, SAMUEL V. LUCAS 1, and LESLIE T. WEBSTER JR. 1

1 Department of Pharmacology, School of Medicine, Case Western Reserve University, Cleveland, Ohio 44106

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.

Submitted on March 7, 1980
Accepted on May 8, 1980






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