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Record Information
Version5.0
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

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point123.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.14 g/LNot Available
LogP0.4Not Available
Experimental Spectral Properties

Experimental Collision Cross Sections

PredictorAdduct TypeData SourceCCS Value (Å2)Reference
AllCCS[M+H]+Not Available134.362http://allccs.zhulab.cn/database/detail?ID=AllCCS00001095
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.14 g/LALOGPS
logP10(0.78) g/LALOGPS
logP10(1.35) g/LChemAxon
logS10(-1.8) g/LALOGPS
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
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+141.32231661259
DarkChem[M-H]-136.93831661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Carbimazole GC-MS (Non-derivatized) - 70eV, Positivesplash10-03fr-9800000000-2e330ed34af7d68055402017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Carbimazole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbimazole LC-ESI-qTof , Positive-QTOFsplash10-014i-0900000000-c5aaa0a285a7152c688a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbimazole , positive-QTOFsplash10-014i-0900000000-c5aaa0a285a7152c688a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbimazole 75V, Positive-QTOFsplash10-066r-9600000000-5be17fd1f01632c6cb9c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbimazole 90V, Positive-QTOFsplash10-0a4i-9300000000-16b74f9a3d11f6bb48fc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbimazole 45V, Positive-QTOFsplash10-014i-1900000000-11854a1d68ea7f2eadd72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbimazole 60V, Positive-QTOFsplash10-014i-4900000000-a77f532e6287ed5f76712021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbimazole 30V, Positive-QTOFsplash10-014i-0900000000-d03c5bb78707544deb242021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carbimazole 15V, Positive-QTOFsplash10-014i-0900000000-d986f63d8ddb8fe7b98c2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carbimazole 10V, Positive-QTOFsplash10-014i-0900000000-8efb8d1fbe7fc1a7a09a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carbimazole 20V, Positive-QTOFsplash10-014i-4900000000-f4b3057782e7db8f051a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carbimazole 40V, Positive-QTOFsplash10-014l-9100000000-b5e879644f210d623b8a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carbimazole 10V, Negative-QTOFsplash10-000i-1900000000-65e89752436d63c363742016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carbimazole 20V, Negative-QTOFsplash10-00di-9300000000-40a049b6c43878ed4c0b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carbimazole 40V, Negative-QTOFsplash10-00di-9100000000-f4973203090a82eda6082016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carbimazole 10V, Positive-QTOFsplash10-014i-0900000000-b88a8d120a4c3e96464c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carbimazole 20V, Positive-QTOFsplash10-014i-2900000000-bce3206f9004009a58a82021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carbimazole 40V, Positive-QTOFsplash10-0a4i-9100000000-b6859c046396330cc13c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carbimazole 10V, Negative-QTOFsplash10-03di-2900000000-08caa8807d232304699e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carbimazole 20V, Negative-QTOFsplash10-03dj-9700000000-e8eb5699a75bd0fa066e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carbimazole 40V, Negative-QTOFsplash10-0002-9200000000-8b02cfc0c0779bdd72fc2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00389 details
UrineExpected but not QuantifiedNot QuantifiedNot 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
FooDB 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
MarkerDB IDNot Available
Good Scents 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 ]