Human Metabolome Database: Showing metabocard for Carbimazole (HMDB0014533)

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

enzymes (2) Show 2 proteins

Record Information

Version

4.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2017-12-07 02:46:08 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 SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Athyromazole	ChEBI
Carbethoxymethimazole	ChEBI
Carbimazol	ChEBI
Carbimazolum	ChEBI
Carbinazole	ChEBI
Ethyl 3-methyl-2-thioimidazoline-1-carboxylate	ChEBI
Thyrostat	ChEBI
Ethyl 3-methyl-2-thioimidazoline-1-carboxylic acid	Generator
Henning berlin brand OF carbimazole	MeSH
neo-Mercazole	MeSH
neo-Thyreostat	MeSH
Tarbis brand OF carbimazole	MeSH
Carbimazole henning	MeSH
Herbrand brand OF carbimazole	MeSH
neo Tomizol	MeSH
Neomercazole	MeSH
Roche brand OF carbimazole	MeSH
Sanofi synthelabo brand OF carbimazole	MeSH

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

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

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

Disposition

Biological location:

Subcellular:

Biofluid and excreta:

Role

Industrial application:

Drug

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental 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

Predicted 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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03fr-9800000000-2e330ed34af7d6805540	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-014i-0900000000-c5aaa0a285a7152c688a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-014i-0900000000-c5aaa0a285a7152c688a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-8efb8d1fbe7fc1a7a09a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-4900000000-f4b3057782e7db8f051a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014l-9100000000-b5e879644f210d623b8a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-1900000000-65e89752436d63c36374	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9300000000-40a049b6c43878ed4c0b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9100000000-f4973203090a82eda608	View in MoNA

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Location

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

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

FoodDB 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

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)

Structure for HMDB0014533 (Carbimazole)

Enzymes

References

References