Identification

Name
Carbimazole
Accession Number
DB00389
Description

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

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 186.232
Monoisotopic: 186.046298264
Chemical Formula
C7H10N2O2S
Synonyms
  • Athyromazole
  • Carbethoxymethimazole
  • Carbimazol
  • Carbimazole
  • Carbimazolo
  • Carbimazolum
  • Carbinazole
  • Ethyl 3-methyl-2-thioimidazoline-1-carboxylate
External IDs
  • CG 1

Pharmacology

Pharmacology
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Indication

For the treatment of hyperthyroidism and thyrotoxicosis. It is also used to prepare patients for thyroidectomy.

Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
Contraindications & Blackbox Warnings
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Pharmacodynamics

Carbimazole 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 action

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.

TargetActionsOrganism
AThyroid peroxidase
inhibitor
Humans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding

85%

Metabolism
Not Available
Route of elimination
Not Available
Half-life
Not Available
Clearance
Not Available
Adverse Effects
Medicalerrors
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Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbciximabCarbimazole may increase the anticoagulant activities of Abciximab.
AcalabrutinibThe therapeutic efficacy of Carbimazole can be decreased when used in combination with Acalabrutinib.
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Carbimazole.
AcenocoumarolCarbimazole may increase the anticoagulant activities of Acenocoumarol.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Carbimazole.
AcetyldigitoxinThe serum concentration of Acetyldigitoxin can be increased when it is combined with Carbimazole.
AcipimoxThe risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Carbimazole is combined with Acipimox.
AfatinibThe therapeutic efficacy of Carbimazole can be decreased when used in combination with Afatinib.
AldesleukinThe therapeutic efficacy of Carbimazole can be decreased when used in combination with Aldesleukin.
AlectinibThe therapeutic efficacy of Carbimazole can be decreased when used in combination with Alectinib.
Interactions
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Food Interactions
Not Available

Products

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International/Other Brands
Camen (Dalim) / Carbimazol (Sanofi-Aventis) / Carbinom (XL Lab) / Carbizol (Square) / Neomercazole (Abbott) / Neomerdin (MedChoice) / Newmazole (Genuine) / Thyrocab (Abbott) / Thyrostat (Ni-The) / Tyrazol (Orion) / Upha Carbimazole (CCM)

Categories

ATC Codes
H03BB01 — Carbimazole
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
N-substituted imidazoles / Imidazolethiones / Heteroaromatic compounds / Thioureas / Organic carbonic acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organic oxides
show 1 more
Substituents
Aromatic heteromonocyclic compound / Azacycle / Carbonic acid derivative / Heteroaromatic compound / Hydrocarbon derivative / Imidazole-1-carbonyl group / Imidazole-2-thione / N-substituted imidazole / Organic nitrogen compound / Organic oxide
show 6 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
carbamate ester, imidazoles, thioureas (CHEBI:617099)

Chemical Identifiers

UNII
8KQ660G60G
CAS number
22232-54-8
InChI Key
CFOYWRHIYXMDOT-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

References

General References
  1. Carbimazole 5 mg Tablets - Summary of Product Characteristics - eMC [Link]
Human Metabolome Database
HMDB0014533
KEGG Drug
D07616
KEGG Compound
C07615
PubChem Compound
31072
PubChem Substance
46506359
ChemSpider
28829
BindingDB
50275889
RxNav
2020
ChEBI
617099
ChEMBL
CHEMBL508102
ZINC
ZINC000000001091
Therapeutic Targets Database
DAP000762
PharmGKB
PA164742970
Wikipedia
Carbimazole
MSDS
Download (57.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentPaediatric Thyrotoxicosis1
3Unknown StatusTreatmentGraves Diseases / Hyperthyroidism1
Not AvailableActive Not RecruitingNot AvailableHyperthyroidism1
Not AvailableCompletedTreatmentEndocrine ophthalmopathy1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, film coatedOral
Tablet
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)123.5 °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 RuleNoChemAxon
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 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9383
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-014i-0900000000-c5aaa0a285a7152c688a

Targets

Drugtargets
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Peroxidase activity
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
Uniprot Name
Thyroid peroxidase
Molecular Weight
102961.63 Da
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]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxygen binding
Specific Function
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name
CYP19A1
Uniprot ID
P11511
Uniprot Name
Aromatase
Molecular Weight
57882.48 Da
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]

Drug created on June 13, 2005 13:24 / Updated on March 04, 2021 11:11