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
Review of the outcome of management of Graves' disease in children and adolescents.
2001 Apr
Haematopoietic growth factor in antithyroid-drug-induced agranulocytosis.
2001 Aug
[Problems in the management of thyrotoxicosis in Black Africa: the Tongolese experience].
2001 Dec
[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
Graves' disease presenting as hemiparkinsonism.
2001 Mar
Congenital thyrotoxicosis in premature infants.
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
Pancytopenia responding to treatment of hyperthyroidism: a clinical case and review of the literature.
2002 Dec
Choanal atresia: the result of maternal thyrotoxicosis or fetal carbimazole?
2002 Jul 22
[Differentiated thyroid gland carcinoma in a scintigraphically hot thyroid nodule: diagnosis and interdisciplinary therapeutic management].
2002 Jun 14
Lingual thyroid and hyperthyroidism: a new case and review of the literature.
2002 Mar
Graves disease in childhood: a review of the options for diagnosis and treatment.
2003
Drug-related taste disturbances.
2003 Aug
Successful radioiodine treatment in a 3 year old child with Graves' disease following antithyroid medication induced neutropenia.
2003 Feb
Thyrotoxicosis.
2003 Jan-Feb
Treatment of carbimazole-induced agranulocytosis and sepsis with granulocyte colony stimulating factor.
2003 Mar
[Methimazole and choanal atresia].
2003 May
Pregnancy with hyperthyroidism.
2003 May
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
Wrong emphasis in case report on cholestatic jaundice.
2004 Feb
Rapid preparation of severe uncontrolled thyrotoxicosis due to Graves' disease with Iopanoic acid--a case report.
2004 Jan
Propylthiouracil and carbimazole associated-antineutrophil cytoplasmic antibodies (ANCA) in patients with Graves' disease.
2004 Jun
Recurrent gestational thyrotoxicosis presenting as recurrent hyperemesis gravidarum--report of two cases.
2004 Oct
Reactions of 1-methyl-2-mercaptoimidazole with hypochlorous acid and superoxide.
2004 Oct
Benchmark calculations for perchlorate from three human cohorts.
2005 Aug
[Treatment of hyperthyroidisms in Brazzaville Teaching Hospital, Congo].
2005 Jun
Ongoing queries: Interpretation of serology in asymptomatic or atypical chronic Q fever.
2006 Apr
Patents

Patents

Substance Class Chemical
Created
by admin
on Wed Jul 05 22:53:48 UTC 2023
Edited
by admin
on Wed Jul 05 22:53:48 UTC 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 Wed Jul 05 22:53:48 UTC 2023 , Edited by admin on Wed Jul 05 22:53:48 UTC 2023
WHO-ATC H03BB01
Created by admin on Wed Jul 05 22:53:48 UTC 2023 , Edited by admin on Wed Jul 05 22:53:48 UTC 2023
NCI_THESAURUS C885
Created by admin on Wed Jul 05 22:53:48 UTC 2023 , Edited by admin on Wed Jul 05 22:53:48 UTC 2023
Code System Code Type Description
ECHA (EC/EINECS)
244-854-4
Created by admin on Wed Jul 05 22:53:48 UTC 2023 , Edited by admin on Wed Jul 05 22:53:48 UTC 2023
PRIMARY
LACTMED
Carbimazole
Created by admin on Wed Jul 05 22:53:48 UTC 2023 , Edited by admin on Wed Jul 05 22:53:48 UTC 2023
PRIMARY
NCI_THESAURUS
C83590
Created by admin on Wed Jul 05 22:53:48 UTC 2023 , Edited by admin on Wed Jul 05 22:53:48 UTC 2023
PRIMARY
CHEBI
617099
Created by admin on Wed Jul 05 22:53:48 UTC 2023 , Edited by admin on Wed Jul 05 22:53:48 UTC 2023
PRIMARY
DAILYMED
8KQ660G60G
Created by admin on Wed Jul 05 22:53:48 UTC 2023 , Edited by admin on Wed Jul 05 22:53:48 UTC 2023
PRIMARY
NSC
758966
Created by admin on Wed Jul 05 22:53:48 UTC 2023 , Edited by admin on Wed Jul 05 22:53:48 UTC 2023
PRIMARY
PUBCHEM
31072
Created by admin on Wed Jul 05 22:53:48 UTC 2023 , Edited by admin on Wed Jul 05 22:53:48 UTC 2023
PRIMARY
RXCUI
2020
Created by admin on Wed Jul 05 22:53:48 UTC 2023 , Edited by admin on Wed Jul 05 22:53:48 UTC 2023
PRIMARY RxNorm
INN
323
Created by admin on Wed Jul 05 22:53:48 UTC 2023 , Edited by admin on Wed Jul 05 22:53:48 UTC 2023
PRIMARY
WIKIPEDIA
CARBIMAZOLE
Created by admin on Wed Jul 05 22:53:48 UTC 2023 , Edited by admin on Wed Jul 05 22:53:48 UTC 2023
PRIMARY
ChEMBL
CHEMBL508102
Created by admin on Wed Jul 05 22:53:48 UTC 2023 , Edited by admin on Wed Jul 05 22:53:48 UTC 2023
PRIMARY
CAS
22232-54-8
Created by admin on Wed Jul 05 22:53:48 UTC 2023 , Edited by admin on Wed Jul 05 22:53:48 UTC 2023
PRIMARY
DRUG CENTRAL
497
Created by admin on Wed Jul 05 22:53:48 UTC 2023 , Edited by admin on Wed Jul 05 22:53:48 UTC 2023
PRIMARY
MERCK INDEX
M3069
Created by admin on Wed Jul 05 22:53:48 UTC 2023 , Edited by admin on Wed Jul 05 22:53:48 UTC 2023
PRIMARY Merck Index
MESH
D002231
Created by admin on Wed Jul 05 22:53:48 UTC 2023 , Edited by admin on Wed Jul 05 22:53:48 UTC 2023
PRIMARY
FDA UNII
8KQ660G60G
Created by admin on Wed Jul 05 22:53:48 UTC 2023 , Edited by admin on Wed Jul 05 22:53:48 UTC 2023
PRIMARY
SMS_ID
100000092278
Created by admin on Wed Jul 05 22:53:48 UTC 2023 , Edited by admin on Wed Jul 05 22:53:48 UTC 2023
PRIMARY
DRUG BANK
DB00389
Created by admin on Wed Jul 05 22:53:48 UTC 2023 , Edited by admin on Wed Jul 05 22:53:48 UTC 2023
PRIMARY
EPA CompTox
DTXSID9022736
Created by admin on Wed Jul 05 22:53:48 UTC 2023 , Edited by admin on Wed Jul 05 22:53:48 UTC 2023
PRIMARY
EVMPD
SUB06127MIG
Created by admin on Wed Jul 05 22:53:48 UTC 2023 , Edited by admin on Wed Jul 05 22:53:48 UTC 2023
PRIMARY
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