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Showing metabocard for Carbimazole (HMDB0014533)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
enzymes (2) Show 2 proteins
Record Information
Version3.6
Creation Date2012-09-06 15:16:49 UTC
Update Date2017-08-16 08:46:19 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
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
AthyromazoleChEBI
CarbethoxymethimazoleChEBI
CarbimazolChEBI
CarbimazolumChEBI
CarbinazoleChEBI
Ethyl 3-methyl-2-thioimidazoline-1-carboxylateChEBI
ThyrostatChEBI
Ethyl 3-methyl-2-thioimidazoline-1-carboxylic acidGenerator
Henning berlin brand OF carbimazoleMeSH
neo-MercazoleMeSH
neo-ThyreostatMeSH
Tarbis brand OF carbimazoleMeSH
Carbimazole henningMeSH
Herbrand brand OF carbimazoleMeSH
neo TomizolMeSH
NeomercazoleMeSH
Roche brand OF carbimazoleMeSH
Sanofi synthelabo brand OF carbimazoleMeSH
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
DescriptionThis compound belongs to the class of chemical entities known as carbonylimidazoles. These are substituted imidazoles in which the imidazole ring bears a carbonyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassAzoles
Direct ParentCarbonylimidazoles
Alternative Parents
Substituents
  • Imidazole-1-carbonyl group
  • N-substituted imidazole
  • Imidazole-2-thione
  • Heteroaromatic compound
  • Thiourea
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Antithyroid Agents
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point123.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.14e+00 g/LNot Available
LogP0.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.14 mg/mLALOGPS
logP0.78ALOGPS
logP1.35ChemAxon
logS-1.8ALOGPS
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area32.78 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity49.17 m3·mol-1ChemAxon
Polarizability18.71 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-0900000000-c5aaa0a285a7152c688aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID28829
KEGG Compound IDC07615
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCarbimazole
NuGOwiki LinkHMDB0014533
METLIN IDNot Available
PubChem Compound31072
PDB IDNot Available
ChEBI ID617099
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Thyroid peroxidase
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 ]
Enzyme Details
2. Cytochrome P450 19A1
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 ]