PT  - JOURNAL ARTICLE
AU  - JAMES W. TRACY
AU  - EDWARD H. FAIRCHILD
AU  - SAMUEL V. LUCAS
AU  - LESLIE T. WEBSTER, JR.
TI  - Isolation, Characterization, and Synthesis of an Immunoregulatory Metabolite of Niridazole: 1-Thiocarbamoyl-2-Imidazolidinone
DP  - 1980 Sep 01
TA  - Molecular Pharmacology
PG  - 313--319
VI  - 18
IP  - 2
4099  - http://molpharm.aspetjournals.org/content/18/2/313.short
4100  - http://molpharm.aspetjournals.org/content/18/2/313.full
SO  - Mol Pharmacol1980 Sep 01; 18
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.