Methylthiouracil

Methylthiouracil is an organosulfur compound that is used antithyroid preparation. It is a thioamide, closely related to propylthiouracil. Methylthiouracil is not used clinically in the United States, it has a similar mechanism of action and side effect to that of propylthiouricil. The drug acts to decrease the formation of stored thyroid hormone, as thyroglobulin in the thyroid gland. The clinical effects of the drug to treat the hyperthyroid state can have a lag period of up to two weeks, depending on the stores of thyroglobulin and other factors.

Methylthiouracil
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
IUPAC name
  • 6-methyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.230
Chemical and physical data
FormulaC5H6N2OS
Molar mass142.18 g·mol−1
3D model (JSmol)
SMILES
  • CC1=CC(=O)NC(=S)N1
InChI
  • InChI=1S/C5H6N2OS/c1-3-2-4(8)7-5(9)6-3/h2H,1H3,(H2,6,7,8,9)
  • Key:HWGBHCRJGXAGEU-UHFFFAOYSA-N
  (verify)

Synthesis
Methylthiouracil synthesis:[1]

Methylthiouracil is prepared quite simply by condensation of ethyl acetoacetate with thiourea.[2]

Further work in this series shows that better activity was obtained by incorporation of a lipophilic side chain.

References
  1. List R (1886). "I. Zur Condensation von Thioharnstoff und Acetessigäther" (PDF). Justus Liebigs Annalen der Chemie. 236 (1–2): 1–32. doi:10.1002/jlac.18862360102.
  2. Vorbrüggen H, Ruh-Pohlenz C (April 2004). "Synthesis of nucleosides". Organic reactions. 55: 1–630. doi:10.1002/0471264180.or055.01.
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