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

InChIKey

CFOYWRHIYXMDOT-UHFFFAOYSA-N

CAS DataBase Reference

22232-54-8(CAS DataBase Reference)

NIST Chemistry Reference

Carbimazole(22232-54-8)

Safety Information

Risk Statements 

22-36-43

Safety Statements 

22-36/37/39

RIDADR 

3335

WGK Germany 

3

RTECS 

NJ2441000

HS Code 

2933.29.9000

MSDS

• Language:English Provider:ALFA

Carbimazole Usage And Synthesis

Chemical Properties

White Solid

Originator

Carbimazol,Cid Co.

Uses

Carbimazole, a prodrug of Methimazole (M260300), is used in the treatment of hyperthyroidism.

Uses

Thionamide antithyroid drug.

Uses

Ethyl 3-methyl-2-thionoimidazoline-1-carboxylate is used as thyroid inhibitor.

Definition

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.

Manufacturing Process

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.

Therapeutic Function

Thyroid inhibitor

Clinical Use

Treatment of hyperthyroidism

Synthesis

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.

Metabolism

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

Carbimazole(22232-54-8)Related Product Information

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