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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:39:50 UTC
HMDB IDHMDB0014533
Secondary Accession Numbers
  • HMDB14533
Metabolite Identification
Common NameCarbimazole
DescriptionCarbimazole is only found in individuals that have used or taken this drug. It is an imidazole antithyroid agent. Carbimazole is metabolized to methimazole, which is responsible for the antithyroid activity. [PubChem]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.
Structure
Data?1582753190
Synonyms
ValueSource
AthyromazoleChEBI
CarbethoxymethimazoleChEBI
CarbimazolChEBI
CarbimazolumChEBI
CarbinazoleChEBI
Ethyl 3-methyl-2-thioimidazoline-1-carboxylateChEBI
ThyrostatChEBI
Carbimazol henningKegg
Ethyl 3-methyl-2-thioimidazoline-1-carboxylic acidGenerator
Henning berlin brand OF carbimazoleHMDB
Neo-mercazoleHMDB
Neo-thyreostatHMDB
Tarbis brand OF carbimazoleHMDB
Carbimazole henningHMDB
Herbrand brand OF carbimazoleHMDB
Neo tomizolHMDB
NeomercazoleHMDB
Roche brand OF carbimazoleHMDB
Sanofi synthelabo brand OF carbimazoleHMDB
Chemical FormulaC7H10N2O2S
Average Molecular Weight186.232
Monoisotopic Molecular Weight186.046298264
IUPAC Nameethyl 3-methyl-2-sulfanylidene-2,3-dihydro-1H-imidazole-1-carboxylate
Traditional Namecarbimazole
CAS Registry Number22232-54-8
SMILES
CCOC(=O)N1C=CN(C)C1=S
InChI Identifier
InChI=1S/C7H10N2O2S/c1-3-11-7(10)9-5-4-8(2)6(9)12/h4-5H,3H2,1-2H3
InChI KeyCFOYWRHIYXMDOT-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as carbonylimidazoles. These are substituted imidazoles in which the imidazole ring bears a carbonyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassImidazoles
Direct ParentCarbonylimidazoles
Alternative Parents
Substituents
  • Imidazole-1-carbonyl group
  • Imidazole-2-thione
  • N-substituted imidazole
  • Heteroaromatic compound
  • Carbonic acid derivative
  • Thiourea
  • Azacycle
  • Organic nitrogen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point123.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.14 g/LNot Available
LogP0.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.14 g/LALOGPS
logP0.78ALOGPS
logP1.35ChemAxon
logS-1.8ALOGPS
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area32.78 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity49.17 m³·mol⁻¹ChemAxon
Polarizability18.71 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03fr-9800000000-2e330ed34af7d6805540Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-014i-0900000000-c5aaa0a285a7152c688aSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-0900000000-c5aaa0a285a7152c688aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-8efb8d1fbe7fc1a7a09aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-4900000000-f4b3057782e7db8f051aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-9100000000-b5e879644f210d623b8aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1900000000-65e89752436d63c36374Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9300000000-40a049b6c43878ed4c0bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9100000000-f4973203090a82eda608Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00389 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00389 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00389
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID28829
KEGG Compound IDC07615
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCarbimazole
METLIN IDNot Available
PubChem Compound31072
PDB IDNot Available
ChEBI ID617099
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in calcium ion binding
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
Molecular weight:
102961.63
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. 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 ]
  3. 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 ]
  4. Taurog A: The mechanism of action of the thioureylene antithyroid drugs. Endocrinology. 1976 Apr;98(4):1031-46. [PubMed:1278093 ]
  5. 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 ]
  6. Orgiazzi J, Millot L: [Theoretical aspects of the treatment with antithyroid drugs]. Ann Endocrinol (Paris). 1994;55(1):1-5. [PubMed:7528484 ]
  7. 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 ]
  8. 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 ]
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:
CYP19A1
Uniprot ID:
P11511
Molecular weight:
57882.48
References
  1. 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 ]