Jump to content
 







Main menu
   


Navigation  



Main page
Contents
Current events
Random article
About Wikipedia
Contact us
Donate
 




Contribute  



Help
Learn to edit
Community portal
Recent changes
Upload file
 








Search  

































Create account

Log in
 









Create account
 Log in
 




Pages for logged out editors learn more  



Contributions
Talk
 



















Contents

   



(Top)
 


1 Synthesis  





2 References  














Methylthiouracil






Čeština
Magyar
Bahasa Melayu
Српски / srpski
Srpskohrvatski / српскохрватски
ி
 

Edit links
 









Article
Talk
 

















Read
Edit
View history
 








Tools
   


Actions  



Read
Edit
View history
 




General  



What links here
Related changes
Upload file
Special pages
Permanent link
Page information
Cite this page
Get shortened URL
Download QR code
Wikidata item
 




Print/export  



Download as PDF
Printable version
 
















Appearance
   

 






From Wikipedia, the free encyclopedia
 


Methylthiouracil
Clinical data
AHFS/Drugs.comInternational 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 InfoCard100.000.230 Edit 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 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[edit]

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[edit]

  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.
  • ^ Vorbrüggen H, Ruh-Pohlenz C (April 2004). "Synthesis of nucleosides". Organic reactions. 55: 1–630. doi:10.1002/0471264180.or055.01.

  • Retrieved from "https://en.wikipedia.org/w/index.php?title=Methylthiouracil&oldid=1207053011"

    Categories: 
    Antithyroid drugs
    IARC Group 2B carcinogens
    Pyrimidones
    Thioureas
    Nucleobases
    Hidden categories: 
    Articles with short description
    Short description matches Wikidata
    ECHA InfoCard ID from Wikidata
    Chemical pages without DrugBank identifier
    Drugs with no legal status
     



    This page was last edited on 13 February 2024, at 21:16 (UTC).

    Text is available under the Creative Commons Attribution-ShareAlike License 4.0; additional terms may apply. By using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc., a non-profit organization.



    Privacy policy

    About Wikipedia

    Disclaimers

    Contact Wikipedia

    Code of Conduct

    Developers

    Statistics

    Cookie statement

    Mobile view



    Wikimedia Foundation
    Powered by MediaWiki