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
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).
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) |
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
Basil Drugs AND Pharmaceuticals Pvt Ltd
VCS Chem Tech Pvt Ltd
Maithri Drugs Pvt Ltd
SETV ASRV LLP
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