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
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
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
Title | Date | PubMed |
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[Carbimazole and leukocytoclastic vasculitis: apropos of a case]. | 1999 Apr |
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Neutropenia and anaemia due to carbimazole-dependent antibodies. | 2000 Apr |
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[Problems in the management of thyrotoxicosis in Black Africa: the Tongolese experience]. | 2001 Dec |
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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 |
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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 |
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Congenital thyrotoxicosis in premature infants. | 2001 Mar |
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Risk of torsades de pointes from oral erythromycin with concomitant carbimazole (methimazole) administration. | 2001 Oct |
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Teratogen update: antithyroid drugs-methimazole, carbimazole, and propylthiouracil. | 2002 Jan |
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Controversies in radioiodine therapy: relation to ophthalmopathy, the possible radioprotective effect of antithyroid drugs, and use in large goitres. | 2002 Jul |
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[Differentiated thyroid gland carcinoma in a scintigraphically hot thyroid nodule: diagnosis and interdisciplinary therapeutic management]. | 2002 Jun 14 |
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Thyrotoxic periodic paralysis in a white woman. | 2002 Nov |
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[Vasculitis with renal and pulmonary involvement in a patient receiving benzylthiouracil for Graves disease]. | 2002 Oct |
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Cerebral venous sinus thrombosis precipitated by Graves' disease and Factor V Leiden mutation. | 2003 Feb |
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Leukocytoclastic vasculitis and interstitial nephritis with carbimazole treatment. | 2003 Feb |
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Childhood thrombocytopenia associated with Graves disease is distinct from idiopathic thrombocytopenic purpura. | 2003 Jan-Feb |
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Weight gain in patients after therapy for hyperthyroidism. | 2003 Jul |
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Excessive weight gain following therapy for hyperthyroidism--a major problem. | 2003 Jul |
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CD1a expression in psoriatic skin following treatment with propylthiouracil, an antithyroid thioureylene. | 2003 Jul 3 |
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Hidden hyperthyroidism in a young male patient. | 2003 Jun |
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Treatment of carbimazole-induced agranulocytosis and sepsis with granulocyte colony stimulating factor. | 2003 Mar |
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Pregnancy with hyperthyroidism. | 2003 May |
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The efficacy of low-dose radioactive iodine without a thionamide in the treatment of thyrotoxicosis. | 2003 May-Jun |
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Homocysteine and its relation to B-vitamins in Graves' disease before and after treatment: effect modification by smoking. | 2003 Nov |
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Cholestatic jaundice caused by sequential carbimazole and propylthiouracil treatment for thyrotoxicosis. | 2003 Oct |
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[Thyrotoxic hypokalaemic periodic paralysis in a Caucasian male]. | 2004 |
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Thyrotoxicosis presenting with complete heart block. | 2004 Dec |
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Hypokalaemic thyrotoxic periodic paralysis in an Asian man in the United Kingdom. | 2004 Jan |
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Low failure rate of fixed administered activity of 400 MBq 131I with pre-treatment with carbimazole for thyrotoxicosis: the Gateshead Protocol. | 2004 Jul |
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Recurrent gestational thyrotoxicosis presenting as recurrent hyperemesis gravidarum--report of two cases. | 2004 Oct |
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Reactions of 1-methyl-2-mercaptoimidazole with hypochlorous acid and superoxide. | 2004 Oct |
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Thyrotoxic, hypokalaemic periodic paralysis. | 2005 Aug |
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Thyrotoxicosis and pulmonary hypertension. | 2005 Aug |
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Benchmark calculations for perchlorate from three human cohorts. | 2005 Aug |
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Carbimazole induced eosinophilic granulomatous vasculitis localized to the stomach. | 2005 Aug |
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Radioiodine uptake and thyroid hormone levels on or off simultaneous carbimazole medication: a prospective paired comparison. | 2005 Feb |
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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
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:23:22 GMT 2023
by
admin
on
Fri Dec 15 15:23:22 GMT 2023
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Record UNII |
8KQ660G60G
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Record Status |
Validated (UNII)
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Record Version |
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WHO-VATC |
QH03BB01
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WHO-ATC |
H03BB01
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NCI_THESAURUS |
C885
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244-854-4
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Carbimazole
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C83590
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8KQ660G60G
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323
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CARBIMAZOLE
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CHEMBL508102
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m3069
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D002231
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8KQ660G60G
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100000092278
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DB00389
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SUB06127MIG
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TARGET -> INHIBITOR |
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ACTIVE MOIETY |