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Methylthiouracil
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    Methylthiouracil

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    Methylthiouracil
    Methylthiouracil.svg
    Methylthiouracil-3D-balls.png
    Clinical data
    AHFS/Drugs.com International Drug Names
    ATC code
    Identifiers
    • 6-methyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one
    CAS Number
    PubChem CID
    ChemSpider
    UNII
    KEGG
    ChEMBL
    CompTox Dashboard (EPA)
    ECHA InfoCard 100.000.230
    Chemical and physical data
    Formula C5H6N2OS
    Molar mass 142.18 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 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.

    Synthesis

    Methylthiouracil synthesis:

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

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


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