2-Thiouracil
Names
Preferred IUPAC name
2-Sulfanylidene-2,3-dihydropyrimidin-4(1H)-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.008
KEGG
MeSH Thiouracil
UNII
  • InChI=1S/C4H4N2OS/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8) checkY
    Key: ZEMGGZBWXRYJHK-UHFFFAOYSA-N checkY
  • InChI=1/C4H4N2OS/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8)
    Key: ZEMGGZBWXRYJHK-UHFFFAOYAK
  • O=C1C=CNC(=S)N1
Properties
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).
☒N verify (what is checkY☒N ?)
Infobox references

2-Thiouracil is a specific molecule consisting of a sulfated uracil.

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Thiouracil inhibits thyroid activity by blocking the enzyme thyroid peroxidase.[2] Its use in recent times has been replaced by advent of more potent and safer antithyroid drugs. It occurs in seeds of Brassica and Crucifera species. Thiouracil has been used as antithyroid, coronary vasodilator, and in congestive heart failure although its use has been largely supplanted by other drugs.[3]

References

  1. ↑ Gerabek, W. (2005). Enzyklopädie Medizingeschichte. Walter de Gruyter. p. 152. ISBN 978-3-11-015714-7.
  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.
  3. ↑ "2-Thiouracil".
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