U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

Molecular Formula C7H10N2O2S
Molecular Weight 186.231
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Detection of cell-drug (hapten)-antibody complexes by the gel test.
1992 Jul-Aug
[Carbimazole and leukocytoclastic vasculitis: apropos of a case].
1999 Apr
Drug-dependent antibodies against the prodrug carbimazole do not react with the metabolite thiamazole.
2001 Apr 1
Haematopoietic growth factor in antithyroid-drug-induced agranulocytosis.
2001 Aug
Change from propylthiouracil to carbimazole proves fatal.
2001 Dec 14
Changing drugs--only when necessary.
2001 Dec 14
Graves' disease presenting as hemiparkinsonism.
2001 Mar
SIMS evidence that carbimazole enhances spatial heterogeneity of thyroid iodine storage and targeting in a woman with Graves' disease.
2001 May
Risk of torsades de pointes from oral erythromycin with concomitant carbimazole (methimazole) administration.
2001 Oct
Comparison of various characteristics of women who do and do not attend for breast cancer screening.
2002
Controversies in radioiodine therapy: relation to ophthalmopathy, the possible radioprotective effect of antithyroid drugs, and use in large goitres.
2002 Jul
Choanal atresia: the result of maternal thyrotoxicosis or fetal carbimazole?
2002 Jul 22
Lingual thyroid and hyperthyroidism: a new case and review of the literature.
2002 Mar
Successful treatment of amiodarone-induced thyrotoxicosis.
2002 Mar 19
Aplasia cutis congenita and antithyroid drugs.
2002 Nov
Thyrotoxic periodic paralysis in a white woman.
2002 Nov
[Vasculitis with renal and pulmonary involvement in a patient receiving benzylthiouracil for Graves disease].
2002 Oct
Prevalence of diaphragmatic muscle weakness and dyspnoea in Graves' disease and their reversibility with carbimazole therapy.
2002 Sep
Graves disease in childhood: a review of the options for diagnosis and treatment.
2003
Acute liver failure with concurrent bupropion and carbimazole therapy.
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
Thyrotoxicosis.
2003 Jan-Feb
CD1a expression in psoriatic skin following treatment with propylthiouracil, an antithyroid thioureylene.
2003 Jul 3
[Subacute motor neuropathy induced by T3 hyperthyroidism].
2003 Nov
Homocysteine and its relation to B-vitamins in Graves' disease before and after treatment: effect modification by smoking.
2003 Nov
T4 but not T3 administration is associated with increased recurrence of Graves' disease after successful medical therapy.
2003 Oct
An unusual case of Marine-Lenhart syndrome.
2003 Oct
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
Wrong emphasis in case report on cholestatic jaundice.
2004 Feb
Thyrotoxic hypokalaemic paralysis in a pregnant Afro-Caribbean woman. A case report and review of the literature.
2004 Jan
Hypokalaemic thyrotoxic periodic paralysis in an Asian man in the United Kingdom.
2004 Jan
Rapid preparation of severe uncontrolled thyrotoxicosis due to Graves' disease with Iopanoic acid--a case report.
2004 Jan
Paroxysmal kinesigenic dyskinesia manifestation of hyperthyroidism.
2004 Mar
[Does antithyroidal drug dose influence relapse of treated Graves-Basedow disease?].
2004 May
Testicular germ cell tumour presenting as thyrotoxicosis.
2004 May
Thyrotoxicosis and pulmonary hypertension.
2005 Aug
Benchmark calculations for perchlorate from three human cohorts.
2005 Aug
Prescription drugs: uses and effects. Thyroid disorders: symptom control.
2005 Feb 16-22
Amiodarone-induced thyrotoxicosis due to destructive thyroiditis: therapeutic recommendations.
2005 Mar
Patents

Patents

Substance Class Chemical
Created
by admin
on Fri Dec 15 15:23:22 GMT 2023
Edited
by admin
on Fri Dec 15 15:23:22 GMT 2023
Record UNII
8KQ660G60G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
CARBIMAZOL HENNING
Brand 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 Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
WHO-ATC H03BB01
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
NCI_THESAURUS C885
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
244-854-4
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY
LACTMED
Carbimazole
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY
NCI_THESAURUS
C83590
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY
CHEBI
617099
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY
DAILYMED
8KQ660G60G
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY
NSC
758966
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY
PUBCHEM
31072
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY
RXCUI
2020
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY RxNorm
INN
323
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY
WIKIPEDIA
CARBIMAZOLE
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY
ChEMBL
CHEMBL508102
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY
CAS
22232-54-8
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY
DRUG CENTRAL
497
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY
MERCK INDEX
m3069
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY Merck Index
MESH
D002231
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY
FDA UNII
8KQ660G60G
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY
SMS_ID
100000092278
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY
DRUG BANK
DB00389
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY
EPA CompTox
DTXSID9022736
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY
EVMPD
SUB06127MIG
Created by admin on Fri Dec 15 15:23:22 GMT 2023 , Edited by admin on Fri Dec 15 15:23:22 GMT 2023
PRIMARY
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