9366. 2-Thiouracil

Nomenclature

CAS number: 141-90-2
2,3-Dihydro-2-thioxo-4(1H)-pyrimidinone; 2-mercapto-4-hydroxypyrimidine; 4-hydroxy-2(1H)-pyrimidinethione; 2-mercapto-4(1H)-pyrimidinone; 6-hydroxy-2-mercaptopyrimidine; 2-mercapto-4-pyrimidone; Deracil.
C4H4N2OS; mol wt 128.15.
C 37.49%, H 3.15%, N 21.86%, O 12.48%, S 25.02%.

Description and references

Occurs in seeds of Brassica, Cruciferae: Purves, Br. J. Exp. Pathol. 22, 241 (1941). Prepd by condensing ethyl formylacetate with thiourea: Wheeler, Liddle, Am. Chem. J. 40, 550 (1908). Antithyroid activity results from its interference with the iodination of thyroxine precursors: see Maloof, Soodak, Pharmacol. Rev. 15, 72-79 (1963). Inhibition of nucleic acid metabolism: Cardeilhac, Proc. Soc. Exp. Biol. Med. 125, 692 (1967). Toxicology: K. K. Carroll, R. L. Noble, J. Pharmacol. Exp. Ther. 97, 478 (1949).

Chemical structure

Properties

Minute, bitter crystals, no definite mp. Very slightly soluble in water (1:2000); practically insol in alcohol, ether, acids. Readily sol in alkaline solns. LD100 i.p. in rats: 1500 mg/kg (Carroll, Noble).

Therapeutic Category

Treatment of hyperthyroidism; angina pectoris; congestive heart failure.

Therapeutic Category (Veterinary)

Thyroid depressant. In hyperthyroidism and to promote fattening.

Keywords

Antihyperthyroid