Basic information
- CAS
22232-54-8- Standard SMILES
CCOC(=O)n1ccn(C)c1=S- InChIKey
CFOYWRHIYXMDOT-UHFFFAOYSA-N- Molecular formula
- C7H10N2O2S
- Average molar mass
- 186.23 g/mol
- Monoisotopic mass
- 186.04629874
Overview
Carbimazole is 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. It has a role as a prodrug and an antithyroid drug. It is a member of 1,3-dihydroimidazole-2-thiones and a carbamate ester.
Names & identifiers
- Preferred name
- Carbimazole
- IUPAC
- ethyl 3-methyl-2-sulfanylideneimidazole-1-carboxylate
- English name
- Carbimazole
- Molecular formula
- C7H10N2O2S
- Molecular weight
- 186.23
Names & synonyms
Carbimazole22232-54-8AthyromazoleCarbimazolCarbethoxymethimazoleCarbinazoleCarbimazolumEthyl 3-methyl-2-thioimidazoline-1-carboxylateCarbimazol henningDTXSID9022736NSC-758966CHEBI:617099
Show more names
Ethyl 3-methyl-2-thioxo-2,3-dihydro-1H-imidazole-1-carboxylateCG1NUPL2TyrazolBasolestNeomercazole
8KQ660G60Gethyl 3-methyl-2-sulfanylidene-2,3-dihydro-1H-imidazole-1-carboxylate1H-Imidazole-1-carboxylic acid, 2,3-dihydro-3-methyl-2-thioxo, ethyl esterDTXCID902736CarbimazoloNeo-mercazole 5Neo-mercazole 20RefChem:54713
Database identifiers
- CAS
22232-54-8- PubChem CID
- 31072
- DTXSID
DTXSID9022736- ChEMBL
CHEMBL508102- ChEBI
CHEBI:617099- UNII
- 8KQ660G60G
- EC Number
- 244-854-4
Properties
Computed structural properties
- XLogP
- 0.7
- Topological polar surface area
- 64.9 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 240
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals
LogP0.4
Solubility3.14e+00 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antithyroid Agents; Thionamides
Thyroid hormones and antithyroid medicines
Animal DrugsPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Melting Point123.5 °C
Physical DescriptionSolid
Collision Cross Section
148.0 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID9022736]
143.69 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
134.4 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H302 (18.6%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P260, P261, P264, P264+P265, P270, P272, P273, P280, P301+P317, P302+P352, P305+P351+P338, P318, P319, P321, P330, P333+P317, P337+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 43 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
H360D: May damage the unborn child [Danger Reproductive toxicity]
Hazard information
Regulatory InformationCarbimazole: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Other Safety InformationIMAP assessments - 1H-Imidazole-1-carboxylic acid, 2,3-dihydro-3-methyl-2-thioxo-, ethyl ester: Environment tier I assessment
Hazard Classes and Categories
Acute Tox. 4 (18.6%)
Reproductive toxicity - category 1B
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
CARBIMAZOLE
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Chemistry & industry
Pharmacology
ATC Code
H - Systemic hormonal preparations, excl. sex hormones and insulins
QH - Systemic hormonal preparations, excl. sex hormones and insulin
Protein Binding85%
PharmacodynamicsCarbimazole 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.
Mechanism of Action
Carbimazole is an aitithyroid agent that decreases the uptake and concentration of inorganic iodine by thyroid, it also reduces the formation of di-iodotyrosine and thyroxine. Once converted to its active form of methimazole, it 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.
MeSH Pharmacological ClassificationAgents that are used to treat hyperthyroidism by reducing the excessive production of thyroid hormones.
Cellular LocationsMembrane
Uses & manufacturing
UsesUse (kg; approx.) in Germany (2009): >250
Use ClassificationPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Applications
UsesCarbimazole, a prodrug of Methimazole (M260300), is used in the treatment of hyperthyroidism.
UsesThionamide antithyroid drug.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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