Thiouracil

Thiouracil

Names
IUPAC name 2-Thioxo-1H-pyrimidin-4-one
Identifiers
CAS Number	141-90-2
3D model (Jmol)	Interactive image
ChEBI	CHEBI:348530
ChEMBL	ChEMBL345768
ChemSpider	1066108
KEGG	C19304
MeSH	Thiouracil
PubChem	1269845
UNII	59X161SCYL
InChI InChI=1S/C4H4N2OS/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8) Key: ZEMGGZBWXRYJHK-UHFFFAOYSA-N InChI=1/C4H4N2OS/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8) Key: ZEMGGZBWXRYJHK-UHFFFAOYAK
SMILES O=C1\C=C/NC(=S)N1
Properties
Chemical formula	C4H4N2OS
Molar mass	128.15 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Thiouracil refers both to a specific molecule consisting of a sulfated uracil, and a family of molecules based upon that structure.

Medical use

The substance is a historically relevant anti-thyroid preparation. Astwood E.B. used it in 1943 as therapy of Graves' disease for the first time.^[1] It remains in use.

Thiouracil inhibits thyroid activity by blocking the enzyme thyroid peroxidase.^[2] Its use in recent times has been replaced by advent of more potent and safer antithyroid drugs.

References

1. Gerabek, W. (2005). Enzyklopädie Medizingeschichte. p. 152. ISBN 9783110157147.
2. Nagasaka, A.; Hidaka, H. (1976). "Effect of Antithyroid Agents 6-Propyl-2-Thiouracil and l-Methyl-2-Mercaptoimidazole on Human Thyroid Iodide Peroxidase". Journal of Clinical Endocrinology & Metabolism. 43 (1): 152–8. doi:10.1210/jcem-43-1-152. PMID 947933.