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Methylthiouracil

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Methylthiouracil
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • 6-methyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.000.230Edit this at Wikidata
Chemical and physical data
FormulaC5H6N2OS
Molar mass142.18 g·mol−1
3D model (JSmol)
  • CC1=CC(=O)NC(=S)N1
  • 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)

Methylthiouracil is anorganosulfur compound that is used antithyroid preparation. It is athioamide, closely related topropylthiouracil. 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.

Synthesis

[edit]
Methylthiouracil synthesis:[1]

Methylthiouracil is prepared quite simply by condensation ofethyl acetoacetate withthiourea.[2]

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

References

[edit]
  1. ^List R (1886)."I. Zur Condensation von Thioharnstoff und Acetessigäther".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.ISBN 978-0-471-26418-7.
Thyroid therapy (H03)
Thyroid hormones
Antithyroid preparations
Thyroid peroxidase
inhibitors (thioamide)
Blockconversion of
T4 toT3
Sodium-iodide symporter
inhibitor
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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
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