Movatterモバイル変換

[0]ホーム
URL:

Jump to content
WikipediaThe Free Encyclopedia
Search

2-Thiouracil

From Wikipedia, the free encyclopedia
2-Thiouracil
Names
Preferred IUPAC name
2-Sulfanylidene-2,3-dihydropyrimidin-4(1H)-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.005.008Edit this at Wikidata
KEGG
MeSHThiouracil
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 mass128.15 g·mol−1
Melting point340 °C (644 °F; 613 K) decomposition
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

2-Thiouracil is a chemical derivative ofuracil in which the oxygen atom in the 2-position of the ring issubstituted by sulfur. It is classified as a thiourea.[1]

Medical use

[edit]

The substance is a historically relevant anti-thyroid preparation.Edwin Astwood used it in 1943 as therapy forGraves' disease for the first time.[2][3][4]

Thiouracil inhibits thyroid activity by blocking the enzymethyroid peroxidase.[5] Its use in recent times has been replaced by advent of more potent and safer antithyroid drugs.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.[6]

References

[edit]
  1. ^Rostkowska, H.; Szczepaniak, K.; Nowak, M. J.; Leszczynski, J.; Kubulat, K.; Person, Willis B. (1990). "Thiouracils. 2. Tautomerism and infrared spectra of thiouracils. Matrix-isolation and ab initio studies".Journal of the American Chemical Society.112 (6):2147–2160.Bibcode:1990JAChS.112.2147R.doi:10.1021/ja00162a016.
  2. ^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.
  3. ^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.
  4. ^Gerabek, W. (2005).Enzyklopädie Medizingeschichte. Walter de Gruyter. p. 152.ISBN 978-3-11-015714-7.
  5. ^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.
  6. ^"2-Thiouracil".
Thyroid therapy (H03)
Thyroid hormones
Antithyroid preparations
Thyroid peroxidase
inhibitors (thioamide)
Blockconversion of
T4 toT3
Sodium-iodide symporter
inhibitor
Other
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
Others
Stub icon

This article about aheterocyclic compound is astub. You can help Wikipedia byadding missing information.

Retrieved from "https://en.wikipedia.org/w/index.php?title=2-Thiouracil&oldid=1304550498"
Categories:
Hidden categories:
[8]ページ先頭
©2009-2026 Movatter.jp