Ethyl 3-methyl-2-thionoimidazoline-1-carboxylate is used as thyroid inhibitor.
Thionamide antithyroid drug.
Carbimazole, a prodrug of Methimazole (M260300), is used in the treatment of hyperthyroidism.
ChEBI: A member of the class of imidazoles that is methimazole in which the nitrogen bearing a hydrogen is converted into its ethoxycarbonyl derivative. A prodrug for methimazol, carbimazole is used for the treatment of hyperthyroidism.
0.1 mol of 1-methyl-2-mercaptoglyoxaline is dissolved in the minimum
quantity of pyridine at 0°C 0.1 mol of ethyl chloroformate is added drop wise
with stirring. More pyridine is added, if necessary, to keep the mixture semi-fluid. The sludge is then placed in an ice bath for 30 minutes. The crystals are
filtered off and washed firstly with a little ethanol and secondly with ethanol
and water. The non-basic desired ethyl 3-methyl-2-thioimidazoline-1-
carboxylate is the colourless needles having a melting point of 122°-123°C.
Treatment of hyperthyroidism
Carbimazole, the ethyl ester of 3-methyl-2-thioimidazolin-1-carboxylic acid
(25.2.7), is synthesized by a simultaneous reaction of ethylenacetal of bromoacetaldehyde
with methylamine and potassium isocyanate, forming 3-methyl-2-imidazolthione (25.2.6),
which is further acylated at the nitrogen atom by ethyl chloroformiate, giving the desired
product (25.2.7).
Veterinary Drugs and Treatments
Carbimazole (a pro-drug of methimazole) or methimazole are
considered by most clinicians to be the agents of choice when using
drugs to treat feline hyperthyroidism. Propylthiouracil has significantly higher incidences of adverse reactions when compared to
methimazole.
Methimazole and therefore, carbimazole, may be useful for the
prophylactic prevention of cisplatin-induced nephrotoxicity in dogs.
Carbimazole is rapidly metabolised to thiamazole,
which is concentrated in the thyroid gland. Over 90%
of orally administered carbimazole is excreted in the
urine as thiamazole or its metabolites. The remainder
appears in faeces. There is 10% enterohepatic circulation.
Thiamazole is metabolised, probably by the liver,
and excreted in the urine. Less than 12% of a dose of
thiamazole may be excreted as unchanged drug
