Methylthiouracil

Methylthiouracil

Systematic (IUPAC) name
6-methyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one
Clinical data
AHFS/Drugs.com	International Drug Names
Identifiers
CAS Number	56-04-2
ATC code	H03BA01 (WHO)
PubChem	CID 667493
ChemSpider	580871
UNII	QW24888U5F
KEGG	C19265
ChEMBL	CHEMBL1330588
Chemical data
Formula	C5H6N2OS
Molar mass	142.18 g/mol
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)

Methylthiouracil is an 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.

Side effects

Like with any drug a wide variety of side effects can occur, but four topics should be kept in mind and the patient informed:

Agranulocytosis - develops rapidly, sore throat and fever are hallmark symptoms. Can be fatal if drug is not discontinued promptly.

Allergic skin reactions the most dangerous of which is Exfoliative Dermatitis, it rapidly can get out of control, notify the physician should a skin eruption occur.

Hepatitis - yellowing of the skin, nausea, yellowing of the whites of the eyes, flu-like symptoms.

Thrombocytopenia - unusual bruising or bleeding.

Synthesis

Methylthiouracil synthesis:^[1]

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.

References

1. R. List, Justus Liebigs Ann. Chem., 236, 1 (1886).

External links

see link on discussion of Hyperthyrodism: http://www.merck.com/mmpe/sec12/ch152/ch152e.html#S12_CH152_T002