Carbimazole

Names

[ Name ]:
Carbimazole

[Synonym ]:
Carbimazolum
Ethyl 3-methyl-2-thioxo-2,3-dihydro-1H-imidazole-1-carboxylate
EINECS 244-854-4
Carbimazol
Carbimazole
Neo-Thyreostat
3-Methyl-2-thioxo-2,3-dihydro-imidazol-1-carbonsaeure-aethylester
1-Methyl-3-carbethoxy-2-thioglyoxalone
1H-Imidazole-1-carboxylic acid, 2,3-dihydro-3-methyl-2-thioxo-, ethyl ester
CG 1
Thyrostat
ethyl 3-methyl-2-thionoimidazoline-1-carboxylate
Carbethoxymethimazole
3-methyl-2-thioxo-2,3-dihydro-imidazole-1-carboxylic acid ethyl ester
ethyl 3-methyl-2-sulfanylideneimidazole-1-carboxylate
3-methyl-1-ethoxycarbonylimidazoline-2-thione
Carbinazole
2,3-Dihydro-3-methyl-2-thioxo-1H-imidazole-1-carboxylic Acid Ethyl Ester
Athyromazole
1-Ethoxycarbonyl-3-methyl-2-thioxo-4-imidazoline
MFCD00027421
Neomercazole
1-Ethoxycarbonyl-3-methyl-2-thio-4-imidazoline

Biological Activity

[Description]:

Carbimazole is an imidazole antithyroid agent. Target: OthersCarbimazole is an effective thyroid hormone inhibitor under a class of drugs known as pro-drugs. It is considered a pro-drug because it converts to methimazole after being absorbed by the body, generating an antithyroid action that works against hyperthyroidism (excessive production of thyroid hormones) and thyrotoxicosis (inflammation of the thyroid gland) [1]. Methimazole prevents the thyroid peroxidase enzyme from coupling and iodinating the tyrosine residues on thyroglobulin, hence reducing the production of the thyroid hormones T3 and T4 (thyroxine) [2].Carbimazole (CBZ) is one of the major drugs currently used for the treatment of Graves' disease. Experiments with [35S] CBZ in rats showed that the drug is so rapidly transformed to MMI after i.v. injection (within 3 min) that very little of the unchanged drug would be expected to reach the thyroid gland. The antithyroid action of CBZ in rats, therefore, can be ascribed entirely to the MMI to which it is rapidly converted [3].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Endocrinology

[References]

[1]. Taurog, A., The mechanism of action of the thioureylene antithyroid drugs. Endocrinology, 1976. 98(4): p. 1031-46.

[2]. Magnusson, R.P., A. Taurog, and M.L. Dorris, Mechanism of iodide-dependent catalatic activity of thyroid peroxidase and lactoperoxidase. J Biol Chem, 1984. 259(1): p. 197-205.

[3]. Nakashima, T. and A. Taurog, Rapid conversion of carbimazole to methimazole in serum; evidence for an enzymatic mechanism. Clin Endocrinol (Oxf), 1979. 10(6): p. 637-48.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
240.4±23.0 °C at 760 mmHg

[ Melting Point ]:
124°C

[ Molecular Formula ]:
C₇H₁₀N₂O₂S

[ Molecular Weight ]:
186.232

[ Flash Point ]:
99.2±22.6 °C

[ Exact Mass ]:
186.046295

[ PSA ]:
68.25000

[ LogP ]:
0.34

[ Vapour Pressure ]:
0.0±0.5 mmHg at 25°C

[ Index of Refraction ]:
1.612

[ Storage condition ]:
Refrigerator

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NJ2441000

CHEMICAL NAME :: 4-Imidazoline-1-carboxylic acid, 3-methyl-2-thioxo-, ethyl ester

CAS REGISTRY NUMBER :: 22232-54-8

BEILSTEIN REFERENCE NO. :: 0144339

LAST UPDATED :: 199612

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C7-H10-N2-O2-S

MOLECULAR WEIGHT :: 186.25

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 703 mg/kg/17W-I

TOXIC EFFECTS :: Sense Organs and Special Senses (Ear) - change in acuity Sense Organs and Special Senses (Ear) - tinnitus

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 25 mg/kg/6W-I

TOXIC EFFECTS :: Liver - hepatitis (hepatocellular necrosis), diffuse

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 23 mg/kg/5W-I

TOXIC EFFECTS :: Liver - jaundice, cholestatic

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Parenteral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 1 mg/kg/1D-I

TOXIC EFFECTS :: Liver - jaundice, other or unclassified

MUTATION DATA

TYPE OF TEST :: Mutation in microorganisms

TEST SYSTEM :: Yeast - Saccharomyces cerevisiae

DOSE/DURATION :: 1 gm/L

REFERENCE :: CHINAG Chemistry and Industry (London). (Royal Soc. of Chemistry, Distribution Centre, Blackhorse Rd., Letchworth, Herts SG6 1HN, UK) V.1- 1923- Volume(issue)/page/year: (21),847,1980

Safety Information

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
S22-S36/37/39

[ RIDADR ]:
3335

[ RTECS ]:
NJ2441000

[ HS Code ]:
2922499915

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933290090

[ Summary ]:
2933290090. other compounds containing an unfused imidazole ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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Related Compounds

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