2-Thiouracil

Thiouracil Structural Formula.V2.svg 120px 2-Sulfanylidene-2,3-dihydropyrimidin-4(1H)-one correct chemspider 1066108 correct FDA 59X161SCYL 1/C4H4N2OS/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8) ZEMGGZBWXRYJHK-UHFFFAOYAK correct EBI 345768 correct chemspider 1S/C4H4N2OS/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8) correct chemspider ZEMGGZBWXRYJHK-UHFFFAOYSA-N correct CAS 141-90-2 1269845 correct EBI 348530 O=C1C=CNC(=S)N1 Thiouracil correct kegg C19304 4 4 2 1 1 340 decomposition 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.Rostkowska H. Szczepaniak K. Nowak M. J. Leszczynski J. Kubulat K. Person Willis B. Thiouracils. 2. Tautomerism and infrared spectra of thiouracils. Matrix-isolation and ab initio studies Journal of the American Chemical Society 1990 112 6 2147–2160 10.1021/ja00162a016 1990JAChS.112.2147R 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.10.1001/jama.251.13.1743 Landmark article May 8, 1943: Treatment of hyperthyroidism with thiourea and thiouracil. By E.B. Astwood 1984 Astwood E. B. JAMA: The Journal of the American Medical Association 251 13 1743–1746 6422063 10.1530/EJE-18-0678 Antithyroid drug therapy: 70 years later 2018 Burch Henry B. Cooper David S. European Journal of Endocrinology 179 5 R261–R274 30320502 https://books.google.com/books?id=LLoOUP-y54YC&dq=parry+struma&pg=PA152 Gerabek, W. Enzyklopädie Medizingeschichte 152 2005 Walter de Gruyter 978-3-11-015714-7 Thiouracil inhibits thyroid activity by blocking the enzyme thyroid peroxidase. 10.1210/jcem-43-1-152 Effect of Antithyroid Agents 6-Propyl-2-Thiouracil and l-Methyl-2-Mercaptoimidazole on Human Thyroid Iodide Peroxidase 1976 Nagasaka A. Hidaka H. Journal of Clinical Endocrinology & Metabolism 43 152–8 947933 1 Its use in recent times has been replaced by advent of more potent and safer antithyroid drugs.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.https://pubchem.ncbi.nlm.nih.gov/compound/thiouracil 2-Thiouracil References Category:Pyrimidines Category:IARC Group 2B carcinogens Category:Thioureas Category:Nucleobases