Grundinformationen
- CAS
22232-54-8- Standard-SMILES
CCOC(=O)n1ccn(C)c1=S- InChIKey
CFOYWRHIYXMDOT-UHFFFAOYSA-N- Summenformel
- C7H10N2O2S
- Durchschnittliche Molmasse
- 186,23 g/mol
- Monoisotopische Masse
- 186,04629874
Überblick
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.
Namen und Bezeichner
- Bevorzugter Name
- Carbimazole
- IUPAC
- ethyl 3-methyl-2-sulfanylideneimidazole-1-carboxylate
- Lokaler Name
- Carbimazol
- Englischer Name
- Carbimazole
- Summenformel
- C7H10N2O2S
- Molmasse
- 186.23
Namen und Synonyme
Carbimazole22232-54-8AthyromazoleCarbimazolCarbethoxymethimazoleCarbinazoleCarbimazolumEthyl 3-methyl-2-thioimidazoline-1-carboxylateCarbimazol henningDTXSID9022736NSC-758966CHEBI:617099
Weitere Namen anzeigen
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
Datenbank-Bezeichner
- CAS
22232-54-8- PubChem CID
- 31072
- DTXSID
DTXSID9022736- ChEMBL
CHEMBL508102- ChEBI
CHEBI:617099- UNII
- 8KQ660G60G
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,7
- Polarare Oberfläche (TPSA)
- 64,9 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 12
- Formalladung
- 0
- Komplexität
- 240
Experimentelle und physikochemische Eigenschaften
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]
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
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]
Gefahrenhinweise
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
Toxikologische Informationen
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
Chemie und Industrie
Pharmakologische Informationen
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
Verwendung und Herstellung
UsesUse (kg; approx.) in Germany (2009): >250
Use ClassificationPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Anwendungen
VerwendenCarbimazole, a prodrug of Methimazole (M260300), is used in the treatment of hyperthyroidism.
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