7869. Propylthiouracil

Nomenclature

CAS number: 51-52-5
2,3-Dihydro-6-propyl-2-thioxo-4(1H)pyrimidinone; 6-propyl-2-thiouracil; 2-thio-4-oxo-6-propyl-1,3-pyrimidine; 2-thio-6-propyl-1,3-pyrimidin-4-one; Propacil (Chugai); Propycil (Kali-Chemie); Propyl-Thyracil (Frosst); Thyreostat II (Herbrand).
C7H10N2OS; mol wt 170.23.
C 49.39%, H 5.92%, N 16.46%, O 9.40%, S 18.84%.

Description and references

Prepd by the condensation of ethyl β-oxocaproate with thiourea: Anderson et al., J. Am. Chem. Soc. 67, 2197 (1945). Comprehensive description: H. Y. Aboul-Enein, Anal. Profiles Drug Subs. 6, 457-486 (1977). Review of pharmacology and clinical experience: D. S. Cooper et al., N. Engl. J. Med. 311, 1353-1362 (1984).

Chemical structure

Properties

White, bitter cryst powder of starch-like appearance to the eye and to the touch, mp 219-221°. uv max (methanol): 275, 214 nm (ε 15800, 15600); (methanolic KOH): 315.5, 260, 207.5 nm (ε 10900, 10700, 15400). One part dissolves in ≈900 parts water at 20°, in 100 parts boiling water, in 60 parts ethyl alcohol, in 60 parts acetone. Practically insol in ether, chloroform, benzene. Freely sol in aq solns of ammonia and alkali hydroxides. A satd aq soln is neutral or slightly acid to litmus.

Caution

This substance is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-227.

Therapeutic Category

Antihyperthyroid.

Therapeutic Category (Veterinary)

Antihyperthyroid. Has been used to promote fattening.

Keywords

Antihyperthyroid