Structure via PubChem · Public domain (PubChem)
methylthiouracil
Sign in to saveAlso known as 6-Methyl-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone, 6-Methyl-2-thiouracil
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.
Chemical data
- Formula
- C5H6N2OS
- Molecular weight
- 142.18 g/mol
- IUPAC name
- 6-methyl-2-sulfanylidene-1H-pyrimidin-4-one
- SMILES
- CC1=CC(=O)NC(=S)N1
- InChIKey
- HWGBHCRJGXAGEU-UHFFFAOYSA-N
- XLogP
- -0.2
- Polar surface area
- 73.2 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
- Indications
- Abnormality of the thyroid gland
via ChEMBL · EBI
Research
1,076 papers- [Methylthiouracil dermatitis].Medizinische Klinik · 1950
- [Methylthiouracil in cardiology].El Dia medico · 1950
- Methylthiouracil in the treatment of thyrotoxicosis.The Journal of clinical endocrinology and metabolism · 1948
- [Agranulocytosis and methylthiouracil].Schweizerische medizinische Wochenschrift · 1953
- Methylthiouracil; an antithyroid agent.The Lahey Clinic bulletin · 1949
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Has part
- sulfur
- Mass
- 142.02
Show 6 more facts
- subject has role
- carcinogen
- chemical formula
- C₅H₆N₂OS
- canonical SMILES
- CC1=CC(=O)NC(=S)N1
- medical condition treated
- thyrotoxicosis
- World Health Organisation international non-proprietary name
- methylthiouracil
- has characteristic
- bitterness
Sources (7)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- Synthesis
- References
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== thumb|center|700px|Methylthiouracil synthesis: Methylthiouracil is prepared quite simply by condensation of ethyl acetoacetate with thiourea.
Excerpted from Wikipedia’s “methylthiouracil” article, available under the CC BY-SA 4.0 licence.