Carbimazole

Carbimazole
  • CAS No.:22232-54-8
Other grades of this product :
Carbimazole Basic information
Product Name:Carbimazole
Synonyms:CARBIMAZOLE;ETHYL 3-METHYL-2-THIOMIDAZOLINE-1-CARBOXYLATE;ETHYL 3-METHYL-2-THIONOIMIDAZOLINE-1-CARBOXYLATE;LABOTEST-BB LT00455569;Ethyl 3-methyl-2-thioxo-4-imidazoline-1-carboxylate;1-Methyl-2-imidazolethiol ethyl carbamate;3-methyl-2-thionoimidazoline-1-carboxylic acid ethyl ester;1-ETHOXYCARBONYL-3-METHYL-2-THIOXO-4-IMIDAZOLINE
CAS:22232-54-8
MF:C7H10N2O2S
MW:186.23
EINECS:244-854-4
Product Categories:API;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
Mol File:22232-54-8.mol
Carbimazole Chemical Properties
Melting point 124°C
Boiling point 240.4±23.0 °C(Predicted)
density 1.2900 (rough estimate)
refractive index 1.5400 (estimate)
storage temp. Sealed in dry,Room Temperature
solubility DMSO: soluble5mg/mL, clear (warmed)
form powder
pka-1.70±0.20(Predicted)
color white to beige
Water Solubility Soluble in water, ethanol, chloroform and acetone. Sightly soluble in water.
Sensitive Light Sensitive
Merck 14,1798
BRN 144339
InChIKeyCFOYWRHIYXMDOT-UHFFFAOYSA-N
CAS DataBase Reference22232-54-8(CAS DataBase Reference)
NIST Chemistry ReferenceCarbimazole(22232-54-8)
Safety Information
Risk Statements 22-36-43
Safety Statements 22-36/37/39
RIDADR 3335
WGK Germany 3
RTECS NJ2441000
MSDS Information
ProviderLanguage
ALFA English
Carbimazole Usage And Synthesis
Chemical PropertiesWhite Solid
OriginatorCarbimazol,Cid Co.
UsesCarbimazole, a prodrug of Methimazole (M260300), is used in the treatment of hyperthyroidism.
UsesThionamide antithyroid drug.
UsesEthyl 3-methyl-2-thionoimidazoline-1-carboxylate is used as thyroid inhibitor.
DefinitionChEBI: 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.
Manufacturing Process0.1 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.
Therapeutic FunctionThyroid inhibitor
Clinical UseTreatment of hyperthyroidism
SynthesisCarbimazole, 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 TreatmentsCarbimazole (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.
Drug interactionsPotentially hazardous interactions with other drugs None known
MetabolismCarbimazole 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

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