Carbimazole
Identification
- Name
- Carbimazole
- Accession Number
- DB00389
- Description
An imidazole antithyroid agent. Carbimazole is metabolized to methimazole, which is responsible for the antithyroid activity.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
- Weight
- Average: 186.232
Monoisotopic: 186.046298264 - Chemical Formula
- C7H10N2O2S
- Synonyms
- Athyromazole
- Carbethoxymethimazole
- Carbimazol
- Carbimazole
- Carbimazolo
- Carbimazolum
- Carbinazole
- Ethyl 3-methyl-2-thioimidazoline-1-carboxylate
- External IDs
- CG 1
Pharmacology
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- Indication
For the treatment of hyperthyroidism and thyrotoxicosis. It is also used to prepare patients for thyroidectomy.
- Associated Conditions
- Contraindications & Blackbox Warnings
- Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects
- Pharmacodynamics
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.
- 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.
Target Actions Organism AThyroid peroxidase inhibitorHumans - Absorption
- Not Available
- Volume of distribution
- Not Available
- Protein binding
85%
- Metabolism
- Not Available
- Route of elimination
- Not Available
- Half-life
- Not Available
- Clearance
- Not Available
- Adverse Effects
- Reduce medical errorsand improve treatment outcomes with our comprehensive & structured data on drug adverse effects.Reduce medical errors & improve treatment outcomes with our adverse effects data
- Toxicity
- Not Available
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbciximab Carbimazole may increase the anticoagulant activities of Abciximab. Acalabrutinib The therapeutic efficacy of Carbimazole can be decreased when used in combination with Acalabrutinib. Acebutolol The risk or severity of adverse effects can be increased when Acebutolol is combined with Carbimazole. Acenocoumarol Carbimazole may increase the anticoagulant activities of Acenocoumarol. Acetohexamide The therapeutic efficacy of Acetohexamide can be decreased when used in combination with Carbimazole. Acetyldigitoxin The serum concentration of Acetyldigitoxin can be increased when it is combined with Carbimazole. Acipimox The risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Carbimazole is combined with Acipimox. Afatinib The therapeutic efficacy of Carbimazole can be decreased when used in combination with Afatinib. Aldesleukin The therapeutic efficacy of Carbimazole can be decreased when used in combination with Aldesleukin. Alectinib The therapeutic efficacy of Carbimazole can be decreased when used in combination with Alectinib. Improve patient outcomesBuild effective decision support tools with the industry’s most comprehensive drug-drug interaction checker.Learn more - Food Interactions
- Not Available
Products
- Comprehensive & structured drug product infoFrom application numbers to product codes, connect different identifiers through our commercial datasets.Easily connect various identifiers back to our datasets
- International/Other Brands
- Camen (Dalim) / Carbimazol (Sanofi-Aventis) / Carbinom (XL Lab) / Carbizol (Square) / Neomercazole (Abbott) / Neomerdin (MedChoice) / Newmazole (Genuine) / Thyrocab (Abbott) / Thyrostat (Ni-The) / Tyrazol (Orion) / Upha Carbimazole (CCM)
Categories
- ATC Codes
- H03BB01 — Carbimazole
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as carbonylimidazoles. These are substituted imidazoles in which the imidazole ring bears a carbonyl group.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Azoles
- Sub Class
- Imidazoles
- Direct Parent
- Carbonylimidazoles
- Alternative Parents
- N-substituted imidazoles / Imidazolethiones / Heteroaromatic compounds / Thioureas / Organic carbonic acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organic oxides show 1 more
- Substituents
- Aromatic heteromonocyclic compound / Azacycle / Carbonic acid derivative / Heteroaromatic compound / Hydrocarbon derivative / Imidazole-1-carbonyl group / Imidazole-2-thione / N-substituted imidazole / Organic nitrogen compound / Organic oxide show 6 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- carbamate ester, imidazoles, thioureas (CHEBI:617099)
Chemical Identifiers
- UNII
- 8KQ660G60G
- CAS number
- 22232-54-8
- InChI Key
- CFOYWRHIYXMDOT-UHFFFAOYSA-N
- InChI
- InChI=1S/C7H10N2O2S/c1-3-11-7(10)9-5-4-8(2)6(9)12/h4-5H,3H2,1-2H3
- IUPAC Name
- ethyl 3-methyl-2-sulfanylidene-2,3-dihydro-1H-imidazole-1-carboxylate
- SMILES
- CCOC(=O)N1C=CN(C)C1=S
References
- General References
- Carbimazole 5 mg Tablets - Summary of Product Characteristics - eMC [Link]
- External Links
- Human Metabolome Database
- HMDB0014533
- KEGG Drug
- D07616
- KEGG Compound
- C07615
- PubChem Compound
- 31072
- PubChem Substance
- 46506359
- ChemSpider
- 28829
- BindingDB
- 50275889
- 2020
- ChEBI
- 617099
- ChEMBL
- CHEMBL508102
- ZINC
- ZINC000000001091
- Therapeutic Targets Database
- DAP000762
- PharmGKB
- PA164742970
- Wikipedia
- Carbimazole
- MSDS
- Download (57.5 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Treatment Paediatric Thyrotoxicosis 1 3 Unknown Status Treatment Graves Diseases / Hyperthyroidism 1 Not Available Active Not Recruiting Not Available Hyperthyroidism 1 Not Available Completed Treatment Endocrine ophthalmopathy 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet, film coated Oral Tablet - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 123.5 °C PhysProp logP 0.4 Not Available - Predicted Properties
Property Value Source Water Solubility 3.14 mg/mL ALOGPS logP 0.78 ALOGPS logP 1.35 ChemAxon logS -1.8 ALOGPS pKa (Strongest Basic) -3 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 1 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 32.78 Å2 ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 49.17 m3·mol-1 ChemAxon Polarizability 18.71 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9157 Blood Brain Barrier + 0.9725 Caco-2 permeable + 0.5 P-glycoprotein substrate Non-substrate 0.8746 P-glycoprotein inhibitor I Non-inhibitor 0.7055 P-glycoprotein inhibitor II Non-inhibitor 0.8618 Renal organic cation transporter Non-inhibitor 0.8473 CYP450 2C9 substrate Non-substrate 0.7914 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.7238 CYP450 1A2 substrate Inhibitor 0.9107 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9383 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.925 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7529 Ames test Non AMES toxic 0.7087 Carcinogenicity Non-carcinogens 0.853 Biodegradation Not ready biodegradable 0.9614 Rat acute toxicity 2.7924 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9875 hERG inhibition (predictor II) Non-inhibitor 0.813
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS Not Available MS/MS Spectrum - , positive LC-MS/MS splash10-014i-0900000000-c5aaa0a285a7152c688a
Targets

- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Peroxidase activity
- Specific Function
- Iodination and coupling of the hormonogenic tyrosines in thyroglobulin to yield the thyroid hormones T(3) and T(4).
- Gene Name
- TPO
- Uniprot ID
- P07202
- Uniprot Name
- Thyroid peroxidase
- Molecular Weight
- 102961.63 Da
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- Guilhem I, Massart C, Poirier JY, Maugendre D: Differential evolution of thyroid peroxidase and thyrotropin receptor antibodies in Graves' disease: thyroid peroxidase antibody activity reverts to pretreatment level after carbimazole withdrawal. Thyroid. 2006 Oct;16(10):1041-5. [PubMed:17042691]
- Magnusson RP, Taurog A, Dorris ML: Mechanism of iodide-dependent catalatic activity of thyroid peroxidase and lactoperoxidase. J Biol Chem. 1984 Jan 10;259(1):197-205. [PubMed:6706930]
- Taurog A: The mechanism of action of the thioureylene antithyroid drugs. Endocrinology. 1976 Apr;98(4):1031-46. [PubMed:1278093]
- Perrild H, Gruters-Kieslich A, Feldt-Rasmussen U, Grant D, Martino E, Kayser L, Delange F: Diagnosis and treatment of thyrotoxicosis in childhood. A European questionnaire study. Eur J Endocrinol. 1994 Nov;131(5):467-73. [PubMed:7952157]
- Orgiazzi J, Millot L: [Theoretical aspects of the treatment with antithyroid drugs]. Ann Endocrinol (Paris). 1994;55(1):1-5. [PubMed:7528484]
- Nakashima T, Taurog A: Rapid conversion of carbimazole to methimazole in serum; evidence for an enzymatic mechanism. Clin Endocrinol (Oxf). 1979 Jun;10(6):637-48. [PubMed:476986]
- Humar M, Dohrmann H, Stein P, Andriopoulos N, Goebel U, Roesslein M, Schmidt R, Schwer CI, Loop T, Geiger KK, Pahl HL, Pannen BH: Thionamides inhibit the transcription factor nuclear factor-kappaB by suppression of Rac1 and inhibitor of kappaB kinase alpha. J Pharmacol Exp Ther. 2008 Mar;324(3):1037-44. Epub 2007 Nov 30. [PubMed:18055877]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Oxygen binding
- Specific Function
- Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
- Gene Name
- CYP19A1
- Uniprot ID
- P11511
- Uniprot Name
- Aromatase
- Molecular Weight
- 57882.48 Da
References
- Ayub M, Levell MJ: Structure-activity relationships of the inhibition of human placental aromatase by imidazole drugs including ketoconazole. J Steroid Biochem. 1988 Jul;31(1):65-72. [PubMed:3398530]
Drug created on June 13, 2005 13:24 / Updated on March 04, 2021 11:11