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HomeProduct name listCarbimazole

Carbimazole

Synonym(s):Carbimazole;Carbimazol;Ethyl 3-methyl-2-thioimidazoline-1-carboxylate;1-Ethoxycarbonyl-3-methyl-2-thio-4-imidazoline;1-Methyl-3-carbethoxy-2-thioglyoxalone

  • CAS NO.:22232-54-8
  • Empirical Formula: C7H10N2O2S
  • Molecular Weight: 186.23
  • MDL number: MFCD00027421
  • EINECS: 244-854-4
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-19 20:33:22
Carbimazole Structural

What is Carbimazole?

Chemical properties

White Solid

Originator

Carbimazol,Cid Co.

The Uses of Carbimazole

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

The Uses of Carbimazole

Thionamide antithyroid drug.

The Uses of Carbimazole

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

Indications

For the treatment of hyperthyroidism and thyrotoxicosis. It is also used to prepare patients for thyroidectomy.

Background

An imidazole antithyroid agent. Carbimazole is metabolized to methimazole, which is responsible for the antithyroid activity.

What are the applications of Application

Carbimazole is a suppressor of thyroid hormone production

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

Pharmacokinetics

Carbimazole is a carbethoxy derivative of methimazole. Its antithyroid action is due to its conversion to methimazole after absorption. It is used to treat hyperthyroidism and thyrotoxicosis.

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).

Synthesis_22232-54-8

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

Not Available

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

Properties of Carbimazole

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
CAS DataBase Reference 22232-54-8(CAS DataBase Reference)
NIST Chemistry Reference Carbimazole(22232-54-8)

Safety information for Carbimazole

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H317:Sensitisation, Skin
H319:Serious eye damage/eye irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P321:Specific treatment (see … on this label).
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Carbimazole

InChIKey CFOYWRHIYXMDOT-UHFFFAOYSA-N

Carbimazole manufacturer

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