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Identification
NameCarbimazole
Accession NumberDB00389  (APRD00503)
TypeSmall Molecule
GroupsApproved
Description

An imidazole antithyroid agent. Carbimazole is metabolized to methimazole, which is responsible for the antithyroid activity. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
1H-Imidazole-1-carboxylic acid, 2,3-dihydro-3-methyl-2-thioxo-, ethyl ester Ethyl 3-methyl-2-thioimidazoline-1-carboxylateNot AvailableWHO
AthyromazoleNot AvailableIS
CarbethoxymethimazoleNot AvailableNot Available
CarbimazolFrench/German/SpanishDCF, BAN
CarbimazoloNot AvailableDCIT
CarbimazolumLatinINN
CarbinazoleNot AvailableNot Available
Ethyl 3-methyl-2-thioimidazoline-1-carboxylateNot AvailableNot Available
ThyrostatNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
CamenDalim
CarbimazolSanofi-Aventis
CarbinomXL Lab
CarbizolSquare
NeomercazoleAbbott
NeomerdinMedChoice
NewmazoleGenuine
ThyrocabAbbott
ThyrostatNi-The
TyrazolOrion
Upha CarbimazoleCCM
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number22232-54-8
WeightAverage: 186.232
Monoisotopic: 186.046298264
Chemical FormulaC7H10N2O2S
InChI KeyCFOYWRHIYXMDOT-UHFFFAOYSA-N
InChI
InChI=1S/C7H10N2O2S/c1-3-11-7(10)9-5-4-8(2)6(9)12/h4-5H,3H2,1-2H3
IUPAC Name
ethyl 3-methyl-2-sulfanylidene-2,3-dihydro-1H-imidazole-1-carboxylate
SMILES
CCOC(=O)N1C=CN(C)C1=S
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as imidazolethiones. These are aromatic compounds containing an imidazole ring which bears a thioketone group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzolines
Sub ClassImidazolines
Direct ParentImidazolethiones
Alternative Parents
Substituents
  • N-substituted imidazole
  • Imidazole-2-thione
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Thiourea
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of hyperthyroidism and thyrotoxicosis. It is also used to prepare patients for thyroidectomy.
PharmacodynamicsCarbimazole is a carbethoxy derivative of methimazole. Its antithyroid action is due to its conversion to methimazole after absorption. It is used to treat hyperthyroidism and thyrotoxicosis.
Mechanism of actionCarbimazole 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein binding85%
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9157
Blood Brain Barrier+0.9725
Caco-2 permeable+0.5
P-glycoprotein substrateNon-substrate0.8746
P-glycoprotein inhibitor INon-inhibitor0.7055
P-glycoprotein inhibitor IINon-inhibitor0.8618
Renal organic cation transporterNon-inhibitor0.8473
CYP450 2C9 substrateNon-substrate0.7914
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.7238
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 substrateNon-inhibitor0.9071
CYP450 2D6 substrateNon-inhibitor0.9383
CYP450 2C19 substrateNon-inhibitor0.9026
CYP450 3A4 substrateNon-inhibitor0.925
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7529
Ames testNon AMES toxic0.7087
CarcinogenicityNon-carcinogens0.853
BiodegradationNot ready biodegradable0.9614
Rat acute toxicity2.7924 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9875
hERG inhibition (predictor II)Non-inhibitor0.813
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point123.5 °CPhysProp
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
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesH03BB01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (57.5 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Thyroid peroxidase

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Thyroid peroxidase P07202 Details

References:

  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  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
  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
  4. Taurog A: The mechanism of action of the thioureylene antithyroid drugs. Endocrinology. 1976 Apr;98(4):1031-46. Pubmed
  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
  6. Orgiazzi J, Millot L: [Theoretical aspects of the treatment with antithyroid drugs] Ann Endocrinol (Paris). 1994;55(1):1-5. Pubmed
  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
  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

Enzymes

1. Cytochrome P450 19A1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 19A1 P11511 Details

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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:10