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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2023-02-21 17:18:13 UTC

HMDB ID

HMDB0014533

Secondary Accession Numbers

HMDB14533

Metabolite Identification

Common Name

Carbimazole

Description

Carbimazole 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 389                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       8.458   0.931   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       4.414  -1.808   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       7.081  -1.808   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       6.518   2.872   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       5.748   0.502   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       6.993   1.407   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.501   1.407   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.978   2.872   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.423   4.118   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.748  -1.038   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414  -3.348   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.080  -4.118   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2   10   11                                                       
CONECT    3   10                                                            
CONECT    4    6    8    9                                                  
CONECT    5    6    7   10                                                  
CONECT    6    1    4    5                                                  
CONECT    7    5    8                                                       
CONECT    8    4    7                                                       
CONECT    9    4                                                            
CONECT   10    2    3    5                                                  
CONECT   11    2   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Athyromazole	ChEBI
Carbethoxymethimazole	ChEBI
Carbimazol	ChEBI
Carbimazolum	ChEBI
Carbinazole	ChEBI
Ethyl 3-methyl-2-thioimidazoline-1-carboxylate	ChEBI
Thyrostat	ChEBI
Carbimazol henning	Kegg
Ethyl 3-methyl-2-thioimidazoline-1-carboxylic acid	Generator
Henning berlin brand OF carbimazole	HMDB
Neo-mercazole	HMDB
Neo-thyreostat	HMDB
Tarbis brand OF carbimazole	HMDB
Carbimazole henning	HMDB
Herbrand brand OF carbimazole	HMDB
Neo tomizol	HMDB
Neomercazole	HMDB
Roche brand OF carbimazole	HMDB
Sanofi synthelabo brand OF carbimazole	HMDB

Chemical Formula

C₇H₁₀N₂O₂S

Average Molecular Weight

186.232

Monoisotopic Molecular Weight

186.046298264

IUPAC Name

ethyl 3-methyl-2-sulfanylidene-2,3-dihydro-1H-imidazole-1-carboxylate

Traditional Name

carbimazole

CAS Registry Number

22232-54-8

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 Key

CFOYWRHIYXMDOT-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Imidazoles

Direct Parent

Carbonylimidazoles

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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

carbamate ester (CHEBI:617099 )
imidazoles (CHEBI:617099 )
thioureas (CHEBI:617099 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0014533)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	123.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	3.14 g/L	Not Available
LogP	0.4	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	134.362	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001095

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.14 g/L	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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	141.322	31661259
DarkChem	[M-H]-	136.938	31661259
DeepCCS	[M+H]+	141.411	30932474
DeepCCS	[M-H]-	138.055	30932474
DeepCCS	[M-2H]-	174.877	30932474
DeepCCS	[M+Na]+	150.238	30932474
AllCCS	[M+H]+	139.4	32859911
AllCCS	[M+H-H2O]+	135.4	32859911
AllCCS	[M+NH4]+	143.2	32859911
AllCCS	[M+Na]+	144.3	32859911
AllCCS	[M-H]-	137.8	32859911
AllCCS	[M+Na-2H]-	139.1	32859911
AllCCS	[M+HCOO]-	140.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Carbimazole	CCOC(=O)N1C=CN(C)C1=S	2453.1	Standard polar	33892256
Carbimazole	CCOC(=O)N1C=CN(C)C1=S	1613.3	Standard non polar	33892256
Carbimazole	CCOC(=O)N1C=CN(C)C1=S	1735.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Carbimazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-03fr-9800000000-2e330ed34af7d6805540	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carbimazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbimazole LC-ESI-qTof , Positive-QTOF	splash10-014i-0900000000-c5aaa0a285a7152c688a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbimazole , positive-QTOF	splash10-014i-0900000000-c5aaa0a285a7152c688a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbimazole 75V, Positive-QTOF	splash10-066r-9600000000-5be17fd1f01632c6cb9c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbimazole 90V, Positive-QTOF	splash10-0a4i-9300000000-16b74f9a3d11f6bb48fc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbimazole 45V, Positive-QTOF	splash10-014i-1900000000-11854a1d68ea7f2eadd7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbimazole 60V, Positive-QTOF	splash10-014i-4900000000-a77f532e6287ed5f7671	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbimazole 30V, Positive-QTOF	splash10-014i-0900000000-d03c5bb78707544deb24	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Carbimazole 15V, Positive-QTOF	splash10-014i-0900000000-d986f63d8ddb8fe7b98c	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbimazole 10V, Positive-QTOF	splash10-014i-0900000000-8efb8d1fbe7fc1a7a09a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbimazole 20V, Positive-QTOF	splash10-014i-4900000000-f4b3057782e7db8f051a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbimazole 40V, Positive-QTOF	splash10-014l-9100000000-b5e879644f210d623b8a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbimazole 10V, Negative-QTOF	splash10-000i-1900000000-65e89752436d63c36374	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbimazole 20V, Negative-QTOF	splash10-00di-9300000000-40a049b6c43878ed4c0b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbimazole 40V, Negative-QTOF	splash10-00di-9100000000-f4973203090a82eda608	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbimazole 10V, Positive-QTOF	splash10-014i-0900000000-b88a8d120a4c3e96464c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbimazole 20V, Positive-QTOF	splash10-014i-2900000000-bce3206f9004009a58a8	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbimazole 40V, Positive-QTOF	splash10-0a4i-9100000000-b6859c046396330cc13c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbimazole 10V, Negative-QTOF	splash10-03di-2900000000-08caa8807d232304699e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbimazole 20V, Negative-QTOF	splash10-03dj-9700000000-e8eb5699a75bd0fa066e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbimazole 40V, Negative-QTOF	splash10-0002-9200000000-8b02cfc0c0779bdd72fc	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00389	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00389	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00389

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28829

KEGG Compound ID

C07615

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Carbimazole

METLIN ID

Not Available

PubChem Compound

31072

PDB ID

Not Available

ChEBI ID

617099

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not 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

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 ]

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

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 ]

Showing metabocard for Carbimazole (HMDB0014533)

MOL for HMDB0014533 (Carbimazole)

3D MOL for HMDB0014533 (Carbimazole)

3D SDF for HMDB0014533 (Carbimazole)

3D-SDF for HMDB0014533 (Carbimazole)

PDB for HMDB0014533 (Carbimazole)

3D PDB for HMDB0014533 (Carbimazole)

SMILES for HMDB0014533 (Carbimazole)

INCHI for HMDB0014533 (Carbimazole)

Structure for HMDB0014533 (Carbimazole)

3D Structure for HMDB0014533 (Carbimazole)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

References

References