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
Ongoing queries: Interpretation of serology in asymptomatic or atypical chronic Q fever.
2006-04
Thyrotoxic, hypokalaemic periodic paralysis.
2005-08
Thyrotoxicosis and pulmonary hypertension.
2005-08
Benchmark calculations for perchlorate from three human cohorts.
2005-08
Carbimazole induced eosinophilic granulomatous vasculitis localized to the stomach.
2005-08
Platysmal myoclonus in subclinical hyperthyroidism.
2005-08
[Treatment of hyperthyroidisms in Brazzaville Teaching Hospital, Congo].
2005-06
Pyoderma gangraenosum associated with autoimmune thyreopathy and hyperandrogenic syndrome.
2005-06
Outcomes of pregnancy complicated by thyroid disease.
2005-06
Prescription drugs: uses and effects. Thyroid disorders: symptom control.
2005-03-09
Amiodarone-induced thyrotoxicosis due to destructive thyroiditis: therapeutic recommendations.
2005-03
Necrotizing glomerulonephritis and pulmonary hemorrhage associated with carbimazole therapy.
2005-03
Radioiodine uptake and thyroid hormone levels on or off simultaneous carbimazole medication: a prospective paired comparison.
2005-02
Carbimazole embryopathy: an emerging phenotype.
2005-01-15
The detrimental effect of anti-thyroid drugs on the outcome of radioiodine therapy is not directly due to decreased radioiodine uptake.
2005-01
Manifestation, management and molecular analysis of candidate genes in two rare cases of thyrotoxic hypokalemic periodic paralysis.
2005
Thyrotoxicosis presenting with complete heart block.
2004-12
Graves' disease in DiGeorge syndrome: patient report with a review of endocrine autoimmunity associated with 22q11.2 deletion.
2004-11
Spontaneous reporting of adverse reactions to carbimazole and propylthiouracil in the UK.
2004-11
[Unclear weight loss. Basedow's disease resp. Graves' disease].
2004-10-13
Recurrent gestational thyrotoxicosis presenting as recurrent hyperemesis gravidarum--report of two cases.
2004-10
Reactions of 1-methyl-2-mercaptoimidazole with hypochlorous acid and superoxide.
2004-10
Low failure rate of fixed administered activity of 400 MBq 131I with pre-treatment with carbimazole for thyrotoxicosis: the Gateshead Protocol.
2004-07
Propylthiouracil and carbimazole associated-antineutrophil cytoplasmic antibodies (ANCA) in patients with Graves' disease.
2004-06
[Does antithyroidal drug dose influence relapse of treated Graves-Basedow disease?].
2004-05
Role of thyroxine in chronic urticaria and angio-oedema.
2004-05
Testicular germ cell tumour presenting as thyrotoxicosis.
2004-05
[Severe neonatal hyperthyroidism which reveals a maternal Graves' disease].
2004-04
Paroxysmal kinesigenic dyskinesia manifestation of hyperthyroidism.
2004-03
Levels of autoantibodies against human TSH receptor predict relapse of hyperthyroidism in Graves' disease.
2004-02
Wrong emphasis in case report on cholestatic jaundice.
2004-02
Thyrotoxic hypokalaemic paralysis in a pregnant Afro-Caribbean woman. A case report and review of the literature.
2004-01
Hypokalaemic thyrotoxic periodic paralysis in an Asian man in the United Kingdom.
2004-01
Rapid preparation of severe uncontrolled thyrotoxicosis due to Graves' disease with Iopanoic acid--a case report.
2004-01
[Thyrotoxic hypokalaemic periodic paralysis in a Caucasian male].
2004
[Subacute motor neuropathy induced by T3 hyperthyroidism].
2003-11
Homocysteine and its relation to B-vitamins in Graves' disease before and after treatment: effect modification by smoking.
2003-11
T4 but not T3 administration is associated with increased recurrence of Graves' disease after successful medical therapy.
2003-10
An unusual case of Marine-Lenhart syndrome.
2003-10
Cholestatic jaundice caused by sequential carbimazole and propylthiouracil treatment for thyrotoxicosis.
2003-10
Drug-related taste disturbances.
2003-08
The efficacy of low-dose radioactive iodine without a thionamide in the treatment of thyrotoxicosis.
2003-07-10
CD1a expression in psoriatic skin following treatment with propylthiouracil, an antithyroid thioureylene.
2003-07-03
Weight gain in patients after therapy for hyperthyroidism.
2003-07
Excessive weight gain following therapy for hyperthyroidism--a major problem.
2003-07
Carbimazole-related gastroschisis.
2003-06
Hidden hyperthyroidism in a young male patient.
2003-06
[Hyperthyroid rheumatism. Review of the literature and a case report].
2003-05-24
[Methimazole and choanal atresia].
2003-05
Detection of cell-drug (hapten)-antibody complexes by the gel test.
1992-07-01
Patents

Patents

Substance Class Chemical
Created
by admin
on Mon Mar 31 17:56:04 GMT 2025
Edited
by admin
on Mon Mar 31 17:56:04 GMT 2025
Record UNII
8KQ660G60G
Record Status Validated (UNII)
Record Version
  • Download
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
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