2-Thiouracil

Chemical compound From Wikipedia, the free encyclopedia

2-Thiouracil

2-Thiouracil is a chemical derivative of uracil in which the oxygen atom in the 2-position of the ring is substituted by sulfur.

Quick Facts Names, Identifiers ...
2-Thiouracil
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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) Y
    Key: ZEMGGZBWXRYJHK-UHFFFAOYSA-N Y
  • 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).
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Medical use

The substance is a historically relevant anti-thyroid preparation. Edwin Astwood used it in 1943 as therapy for Graves' disease for the first time.[1][2][3]

Thiouracil inhibits thyroid activity by blocking the enzyme thyroid peroxidase.[4] Its use in recent times has been replaced by advent of more potent and safer antithyroid drugs.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.[5]

References

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