Chemistry:2-Thiouracil

From HandWiki

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

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.[2][3][4]

Thiouracil inhibits thyroid activity by blocking the enzyme thyroid peroxidase.[5] Its use in recent times has been replaced by advent of more potent and safer antithyroid drugs.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

  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. doi:10.1021/ja00162a016. Bibcode1990JAChS.112.2147R. 
  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. https://books.google.com/books?id=LLoOUP-y54YC&dq=parry+struma&pg=PA152. 
  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". https://pubchem.ncbi.nlm.nih.gov/compound/thiouracil.