Carbimazole

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

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Carbimazole (DB00389)

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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

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Indication

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

Associated Conditions

• Hyperthyroidism

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.

Target	Actions	Organism
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

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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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abciximab	Carbimazole may increase the anticoagulant activities of Abciximab.
Acalabrutinib	The therapeutic efficacy of Carbimazole can be decreased when used in combination with Acalabrutinib.
Acebutolol	The risk or severity of adverse effects can be increased when Acebutolol is combined with Carbimazole.
Acenocoumarol	Carbimazole may increase the anticoagulant activities of Acenocoumarol.
Acetohexamide	The therapeutic efficacy of Acetohexamide can be decreased when used in combination with Carbimazole.
Acetyldigitoxin	The serum concentration of Acetyldigitoxin can be increased when it is combined with Carbimazole.
Acipimox	The risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Carbimazole is combined with Acipimox.
Afatinib	The therapeutic efficacy of Carbimazole can be decreased when used in combination with Afatinib.
Aldesleukin	The therapeutic efficacy of Carbimazole can be decreased when used in combination with Aldesleukin.
Alectinib	The therapeutic efficacy of Carbimazole can be decreased when used in combination with Alectinib.

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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

• H03BB — Sulfur-containing imidazole derivatives
• H03B — ANTITHYROID PREPARATIONS
• H03 — THYROID THERAPY
• H — SYSTEMIC HORMONAL PREPARATIONS, EXCL. SEX HORMONES AND INSULINS

Drug Categories

• Agents Causing Muscle Toxicity
• Antithyroid agents
• Hormone Antagonists
• Hormones, Hormone Substitutes, and Hormone Antagonists
• Imidazoles
• Sulfur-Containing Imidazole Derivatives
• Systemic Hormonal Preparations, Excl. Sex Hormones and Insulins
• Thyroid Products

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 / Hydrocarbon derivatives

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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 / Organic oxygen compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Organosulfur compound / Thiourea

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]

External Links

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

Phase	Status	Purpose	Conditions	Count
3	Completed	Treatment	Paediatric Thyrotoxicosis	1
3	Unknown Status	Treatment	Graves Diseases / Hyperthyroidism	1
Not Available	Active Not Recruiting	Not Available	Hyperthyroidism	1
Not Available	Completed	Treatment	Endocrine ophthalmopathy	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Tablet, film coated	Oral
Tablet

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	123.5 °C	PhysProp
logP	0.4	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	3.14 mg/mL	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	No	ChemAxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9157
Blood Brain Barrier	+	0.9725
Caco-2 permeable	+	0.5
P-glycoprotein substrate	Non-substrate	0.8746
P-glycoprotein inhibitor I	Non-inhibitor	0.7055
P-glycoprotein inhibitor II	Non-inhibitor	0.8618
Renal organic cation transporter	Non-inhibitor	0.8473
CYP450 2C9 substrate	Non-substrate	0.7914
CYP450 2D6 substrate	Non-substrate	0.9116
CYP450 3A4 substrate	Non-substrate	0.7238
CYP450 1A2 substrate	Inhibitor	0.9107
CYP450 2C9 inhibitor	Non-inhibitor	0.9071
CYP450 2D6 inhibitor	Non-inhibitor	0.9383
CYP450 2C19 inhibitor	Non-inhibitor	0.9026
CYP450 3A4 inhibitor	Non-inhibitor	0.925
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.7529
Ames test	Non AMES toxic	0.7087
Carcinogenicity	Non-carcinogens	0.853
Biodegradation	Not ready biodegradable	0.9614
Rat acute toxicity	2.7924 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9875
hERG inhibition (predictor II)	Non-inhibitor	0.813

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	Not Available
MS/MS Spectrum - , positive	LC-MS/MS	splash10-014i-0900000000-c5aaa0a285a7152c688a

Targets

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Details1. Thyroid peroxidase

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]

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