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2-Thiouracil

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2-Thiouracil
Names
Preferred IUPAC name 2-Sulfanylidene-2,3-dihydropyrimidin-4(1H)-one
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.008 Edit this at Wikidata
KEGG
MeSH Thiouracil
PubChem CID
UNII
CompTox Dashboard (EPA)
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=C1C=CNC(=S)N1
Properties
Chemical formula C4H4N2OS
Molar mass 128.15 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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

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.

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 Its use in recent times has been replaced by advent of more potent and safer antithyroid drugs.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

References

  1. Astwood, E. B. (1984). "Landmark article May 8, 1943: Treatment of hyperthyroidism with thiourea and thiouracil. By E.B. Astwood". JAMA: The Journal of the American Medical Association. 251 (13): 1743–1746. doi:10.1001/jama.251.13.1743. PMID 6422063.
  2. Burch, Henry B.; Cooper, David S. (2018). "Antithyroid drug therapy: 70 years later". European Journal of Endocrinology. 179 (5): R261 – R274. doi:10.1530/EJE-18-0678. PMID 30320502.
  3. Gerabek, W. (2005). Enzyklopädie Medizingeschichte. Walter de Gruyter. p. 152. ISBN 978-3-11-015714-7.
  4. 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.
  5. "2-Thiouracil".
Thyroid therapy (H03)
Thyroid hormones
Antithyroid preparations
Thyroid peroxidase
inhibitors (thioamide)
Block conversion of
T4 to T3
Sodium-iodide symporter
inhibitor
Other
Thyroid hormone receptor modulators
Receptor
(ligands)
THRTooltip Thyroid hormone receptor
Agonists
Thyromimetics
(selective agonists)
Antagonists
Transporter
(blockers)
NISTooltip Sodium-iodide symporter
 
Enzyme
(inhibitors)
TPOTooltip Thyroid peroxidase
DIOTooltip Iodothyronine deiodinase
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