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
[Carbimazole and leukocytoclastic vasculitis: apropos of a case].
1999 Apr
Neutropenia and anaemia due to carbimazole-dependent antibodies.
2000 Apr
[Problems in the management of thyrotoxicosis in Black Africa: the Tongolese experience].
2001 Dec
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
Clinical value of a new TSH binding inihibitory activity assay using human TSH receptors in the follow-up of antithyroid drug treated Graves' disease. Comparison with thyroid stimulating antibody bioassay.
2001 Jan
Congenital thyrotoxicosis in premature infants.
2001 Mar
Risk of torsades de pointes from oral erythromycin with concomitant carbimazole (methimazole) administration.
2001 Oct
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
[Differentiated thyroid gland carcinoma in a scintigraphically hot thyroid nodule: diagnosis and interdisciplinary therapeutic management].
2002 Jun 14
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
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
Childhood thrombocytopenia associated with Graves disease is distinct from idiopathic thrombocytopenic purpura.
2003 Jan-Feb
Weight gain in patients after therapy for hyperthyroidism.
2003 Jul
Excessive weight gain following therapy for hyperthyroidism--a major problem.
2003 Jul
CD1a expression in psoriatic skin following treatment with propylthiouracil, an antithyroid thioureylene.
2003 Jul 3
Hidden hyperthyroidism in a young male patient.
2003 Jun
Treatment of carbimazole-induced agranulocytosis and sepsis with granulocyte colony stimulating factor.
2003 Mar
Pregnancy with hyperthyroidism.
2003 May
The efficacy of low-dose radioactive iodine without a thionamide in the treatment of thyrotoxicosis.
2003 May-Jun
Homocysteine and its relation to B-vitamins in Graves' disease before and after treatment: effect modification by smoking.
2003 Nov
Cholestatic jaundice caused by sequential carbimazole and propylthiouracil treatment for thyrotoxicosis.
2003 Oct
[Thyrotoxic hypokalaemic periodic paralysis in a Caucasian male].
2004
Thyrotoxicosis presenting with complete heart block.
2004 Dec
Hypokalaemic thyrotoxic periodic paralysis in an Asian man in the United Kingdom.
2004 Jan
Low failure rate of fixed administered activity of 400 MBq 131I with pre-treatment with carbimazole for thyrotoxicosis: the Gateshead Protocol.
2004 Jul
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
Thyrotoxic, hypokalaemic periodic paralysis.
2005 Aug
Thyrotoxicosis and pulmonary hypertension.
2005 Aug
Benchmark calculations for perchlorate from three human cohorts.
2005 Aug
Carbimazole induced eosinophilic granulomatous vasculitis localized to the stomach.
2005 Aug
Radioiodine uptake and thyroid hormone levels on or off simultaneous carbimazole medication: a prospective paired comparison.
2005 Feb
The detrimental effect of anti-thyroid drugs on the outcome of radioiodine therapy is not directly due to decreased radioiodine uptake.
2005 Jan
[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 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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