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Details

Stereochemistry ACHIRAL
Molecular Formula C7H10N2O2S
Molecular Weight 186.231
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARBIMAZOLE

SMILES

CCOC(=O)N1C=CN(C)C1=S

InChI

InChIKey=CFOYWRHIYXMDOT-UHFFFAOYSA-N
InChI=1S/C7H10N2O2S/c1-3-11-7(10)9-5-4-8(2)6(9)12/h4-5H,3H2,1-2H3

HIDE SMILES / InChI
Carbimazole is a prodrug for methimazole used to treat hyperthyroidism and thyrotoxicosis during pregnancy and breast breastfeeding. Carbimazole is rapidly metabolized to methimazole, which is responsible for the antithyroid activity. Carbimazole is an antithyroid agent that decreases the uptake and concentration of inorganic iodine by the 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. Doses of carbimazole of 30 mg daily or 50 mg weekly have not adversely affected the few breastfed infants studied and no cases of thyroid function alteration have been reported among infants exposed to methimazole via breastmilk. Carbimazole is not approved for marketing in the United States by the U.S. Food and Drug Administration but is available in other countries.

Approval Year

PubMed

PubMed

TitleDatePubMed
[Carbimazole and leukocytoclastic vasculitis: apropos of a case].
1999 Apr
[Characterization of therapy failures in radioiodine therapy of Graves' disease without simultaneous antithyroid agents].
2001 Feb
Clinical validity of a new commercial method for detection of TSH-receptor binding antibodies in sera from patients with Graves' disease treated with antithyroid drugs.
2001 Feb
Risk of torsades de pointes from oral erythromycin with concomitant carbimazole (methimazole) administration.
2001 Oct
Successful treatment with carbimazole of a hyperthyroid pregnancy with hepatic impairment after propylthiouracil administration: a case report.
2002
Radioiodine therapy and thyrostatic drugs and iodine.
2002 Aug
Pancytopenia responding to treatment of hyperthyroidism: a clinical case and review of the literature.
2002 Dec
Teratogen update: antithyroid drugs-methimazole, carbimazole, and propylthiouracil.
2002 Jan
Controversies in radioiodine therapy: relation to ophthalmopathy, the possible radioprotective effect of antithyroid drugs, and use in large goitres.
2002 Jul
Methimazole-induced hepatotoxicity.
2002 May-Jun
Thyrotoxic periodic paralysis in a white woman.
2002 Nov
Thyrotoxicosis--surgical management in the era of evidence-based medicine: experience in western India with 752 cases.
2002 Oct
[Vasculitis with renal and pulmonary involvement in a patient receiving benzylthiouracil for Graves disease].
2002 Oct
Graves disease in childhood: a review of the options for diagnosis and treatment.
2003
Effects of carbimazole on morphology of rat adrenals.
2003 Feb
Cerebral venous sinus thrombosis precipitated by Graves' disease and Factor V Leiden mutation.
2003 Feb
Leukocytoclastic vasculitis and interstitial nephritis with carbimazole treatment.
2003 Feb
Successful radioiodine treatment in a 3 year old child with Graves' disease following antithyroid medication induced neutropenia.
2003 Feb
Childhood thrombocytopenia associated with Graves disease is distinct from idiopathic thrombocytopenic purpura.
2003 Jan-Feb
Carbimazole-related gastroschisis.
2003 Jun
Cholestatic jaundice caused by sequential carbimazole and propylthiouracil treatment for thyrotoxicosis.
2003 Oct
Levels of autoantibodies against human TSH receptor predict relapse of hyperthyroidism in Graves' disease.
2004 Feb
Low failure rate of fixed administered activity of 400 MBq 131I with pre-treatment with carbimazole for thyrotoxicosis: the Gateshead Protocol.
2004 Jul
[Does antithyroidal drug dose influence relapse of treated Graves-Basedow disease?].
2004 May
Carbimazole induced eosinophilic granulomatous vasculitis localized to the stomach.
2005 Aug
Carbimazole embryopathy: an emerging phenotype.
2005 Jan 15
[Treatment of hyperthyroidisms in Brazzaville Teaching Hospital, Congo].
2005 Jun
Patents

Patents

Name Type Language
CARBIMAZOL HENNING
Preferred Name English
CARBIMAZOLE
EP   INN   MART.   MI   WHO-DD  
INN  
Official Name English
carbimazole [INN]
Common Name English
NSC-758966
Code English
CARBIMAZOLE [EP MONOGRAPH]
Common Name English
CARBIMAZOLE [MART.]
Common Name English
3-METHYL-2-THIOI-MIDAZOLINE-1-CARBOXYLATE
Common Name English
CARBIMAZOLE [MI]
Common Name English
Carbimazole [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-VATC QH03BB01
Created by admin on Mon Mar 31 17:56:04 GMT 2025 , Edited by admin on Mon Mar 31 17:56:04 GMT 2025
WHO-ATC H03BB01
Created by admin on Mon Mar 31 17:56:04 GMT 2025 , Edited by admin on Mon Mar 31 17:56:04 GMT 2025
NCI_THESAURUS C885
Created by admin on Mon Mar 31 17:56:04 GMT 2025 , Edited by admin on Mon Mar 31 17:56:04 GMT 2025
Code System Code Type Description
ECHA (EC/EINECS)
244-854-4
Created by admin on Mon Mar 31 17:56:04 GMT 2025 , Edited by admin on Mon Mar 31 17:56:04 GMT 2025
PRIMARY
LACTMED
Carbimazole
Created by admin on Mon Mar 31 17:56:04 GMT 2025 , Edited by admin on Mon Mar 31 17:56:04 GMT 2025
PRIMARY
NCI_THESAURUS
C83590
Created by admin on Mon Mar 31 17:56:04 GMT 2025 , Edited by admin on Mon Mar 31 17:56:04 GMT 2025
PRIMARY
CHEBI
617099
Created by admin on Mon Mar 31 17:56:04 GMT 2025 , Edited by admin on Mon Mar 31 17:56:04 GMT 2025
PRIMARY
DAILYMED
8KQ660G60G
Created by admin on Mon Mar 31 17:56:04 GMT 2025 , Edited by admin on Mon Mar 31 17:56:04 GMT 2025
PRIMARY
NSC
758966
Created by admin on Mon Mar 31 17:56:04 GMT 2025 , Edited by admin on Mon Mar 31 17:56:04 GMT 2025
PRIMARY
PUBCHEM
31072
Created by admin on Mon Mar 31 17:56:04 GMT 2025 , Edited by admin on Mon Mar 31 17:56:04 GMT 2025
PRIMARY
RXCUI
2020
Created by admin on Mon Mar 31 17:56:04 GMT 2025 , Edited by admin on Mon Mar 31 17:56:04 GMT 2025
PRIMARY RxNorm
INN
323
Created by admin on Mon Mar 31 17:56:04 GMT 2025 , Edited by admin on Mon Mar 31 17:56:04 GMT 2025
PRIMARY
WIKIPEDIA
CARBIMAZOLE
Created by admin on Mon Mar 31 17:56:04 GMT 2025 , Edited by admin on Mon Mar 31 17:56:04 GMT 2025
PRIMARY
ChEMBL
CHEMBL508102
Created by admin on Mon Mar 31 17:56:04 GMT 2025 , Edited by admin on Mon Mar 31 17:56:04 GMT 2025
PRIMARY
CAS
22232-54-8
Created by admin on Mon Mar 31 17:56:04 GMT 2025 , Edited by admin on Mon Mar 31 17:56:04 GMT 2025
PRIMARY
DRUG CENTRAL
497
Created by admin on Mon Mar 31 17:56:04 GMT 2025 , Edited by admin on Mon Mar 31 17:56:04 GMT 2025
PRIMARY
MERCK INDEX
m3069
Created by admin on Mon Mar 31 17:56:04 GMT 2025 , Edited by admin on Mon Mar 31 17:56:04 GMT 2025
PRIMARY Merck Index
MESH
D002231
Created by admin on Mon Mar 31 17:56:04 GMT 2025 , Edited by admin on Mon Mar 31 17:56:04 GMT 2025
PRIMARY
FDA UNII
8KQ660G60G
Created by admin on Mon Mar 31 17:56:04 GMT 2025 , Edited by admin on Mon Mar 31 17:56:04 GMT 2025
PRIMARY
SMS_ID
100000092278
Created by admin on Mon Mar 31 17:56:04 GMT 2025 , Edited by admin on Mon Mar 31 17:56:04 GMT 2025
PRIMARY
DRUG BANK
DB00389
Created by admin on Mon Mar 31 17:56:04 GMT 2025 , Edited by admin on Mon Mar 31 17:56:04 GMT 2025
PRIMARY
EPA CompTox
DTXSID9022736
Created by admin on Mon Mar 31 17:56:04 GMT 2025 , Edited by admin on Mon Mar 31 17:56:04 GMT 2025
PRIMARY
EVMPD
SUB06127MIG
Created by admin on Mon Mar 31 17:56:04 GMT 2025 , Edited by admin on Mon Mar 31 17:56:04 GMT 2025
PRIMARY