Details
Stereochemistry | ACHIRAL |
Molecular Formula | C4H6N2S |
Molecular Weight | 114.169 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1C=CNC1=S
InChI
InChIKey=PMRYVIKBURPHAH-UHFFFAOYSA-N
InChI=1S/C4H6N2S/c1-6-3-2-5-4(6)7/h2-3H,1H3,(H,5,7)
DescriptionSources: http://www.drugbank.ca/drugs/DB00763Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/cdi/methimazole.html
Sources: http://www.drugbank.ca/drugs/DB00763
Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/cdi/methimazole.html
Methimazole (also known as Tapazole or Thiamazole or MMI) is an antithyroid drug. Methimazole binds to thyroid peroxidase and thereby inhibits the conversion of iodide to iodine. Thyroid peroxidase normally converts iodide to iodine (via hydrogen peroxide as a cofactor) and also catalyzes the incorporation of the resulting iodide molecule onto both the 3 and/or 5 positions of the phenol rings of tyrosines found in thyroglobulin. Thyroglobulin is degraded to produce thyroxine (T4) and tri-iodothyronine (T3), which are the main hormones produced by the thyroid gland. So methimazole effectively inhibits the production of new thyroid hormones. Methimazole is used for the treatment of hyperthyroidism, goiter, Graves disease and psoriasis.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14982270
Curator's Comment: In 1949, Stanley and Astwood first introduced methimazole
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1839 Sources: http://www.drugbank.ca/drugs/DB00763 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Tapazole Approved UseTAPAZOLE is indicated:
In patients with Graves’ disease with hyperthyroidism or toxic multinodular goiter for whom surgery or radioactive iodine therapy is not an appropriate treatment option.
To ameliorate symptoms of hyperthyroidism in preparation for thyroidectomy or radioactive iodine therapy. Launch Date-6.1646399E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
248 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4042519/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
METHIMAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
213 ng/mL |
0.17 mg/kg bw single, oral dose: 0.17 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
METHIMAZOLE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
299 ng/mL |
0.21 mg/kg bw single, oral dose: 0.21 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
METHIMAZOLE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
380 ng/mL |
0.3 mg/kg bw single, oral dose: 0.3 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
METHIMAZOLE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
803 ng/mL |
0.57 mg/kg bw single, oral dose: 0.57 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
METHIMAZOLE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1661 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4042519/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
METHIMAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
2657 ng × h/mL |
0.17 mg/kg bw single, oral dose: 0.17 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
METHIMAZOLE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
3228 ng × h/mL |
0.21 mg/kg bw single, oral dose: 0.21 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
METHIMAZOLE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
4773 ng × h/mL |
0.3 mg/kg bw single, oral dose: 0.3 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
METHIMAZOLE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
7136 ng × h/mL |
0.57 mg/kg bw single, oral dose: 0.57 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
METHIMAZOLE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
1833 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4042519/ |
10 mg single, intravenous dose: 10 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
METHIMAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
2450 ng × h/mL |
0.16 mg/kg bw single, intravenous dose: 0.16 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered: |
METHIMAZOLE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
2922 ng × h/mL |
0.21 mg/kg bw single, intravenous dose: 0.21 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered: |
METHIMAZOLE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4042519/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
METHIMAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
14 h |
0.17 mg/kg bw single, oral dose: 0.17 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
METHIMAZOLE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
14 h |
0.21 mg/kg bw single, oral dose: 0.21 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
METHIMAZOLE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
20.1 h |
0.3 mg/kg bw single, oral dose: 0.3 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
METHIMAZOLE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
15 h |
0.57 mg/kg bw single, oral dose: 0.57 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
METHIMAZOLE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
5.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4042519/ |
10 mg single, intravenous dose: 10 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
METHIMAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
20.7 h |
0.16 mg/kg bw single, intravenous dose: 0.16 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered: |
METHIMAZOLE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
18.5 h |
0.21 mg/kg bw single, intravenous dose: 0.21 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered: |
METHIMAZOLE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
major [IC50 14 uM] | ||||
no [IC50 >/=1000 uM] | ||||
no [IC50 >/=1000 uM] | ||||
no [IC50 >/=1000 uM] | ||||
no [IC50 >/=1000 uM] | ||||
weak [IC50 100 uM] | ||||
weak [IC50 100 uM] | ||||
weak [Inhibition 50 uM] | ||||
weak [Ki 7500 uM] |
PubMed
Title | Date | PubMed |
---|---|---|
Body, heart, thyroid gland and skeletal muscle weight changes in rats with altered thyroid status. | 2001 |
|
Drug-induced congenital defects: strategies to reduce the incidence. | 2001 |
|
[Ablative therapy for immune hyperthyroidism in patients with ophthalmopathy]. | 2001 |
|
The activity of antioxidant enzymes and the content of uncoupling protein-1 in the brown adipose tissue of hypothyroid rats: comparison with effects of iopanoic acid. | 2001 |
|
Identification of the gene encoding Brain Cell Membrane Protein 1 (BCMP1), a putative four-transmembrane protein distantly related to the Peripheral Myelin Protein 22 / Epithelial Membrane Proteins and the Claudins. | 2001 |
|
Coexistence of Graves' disease and struma ovarii: case report and literature review. | 2001 Apr |
|
Malignant hyperthermia in a patient with Graves' disease during subtotal thyroidectomy. | 2001 Apr |
|
Morning granulocytopenia in a case of Graves' disease. | 2001 Apr |
|
A case of pulmonary metastatic thyroid cancer complicated with Graves' disease. | 2001 Apr |
|
Graves' disease presenting as elephantiasic pretibial myxedema and nodules of the hands. | 2001 Apr |
|
[Simultaneous occurrence of Basedow's disease and autoimmune hemolytic anemia]. | 2001 Apr |
|
Estimation of antithyroid drug dose in Graves' disease: value of quantification of thyroid blood flow with color duplex sonography. | 2001 Aug |
|
Remission and recurrence of hyperthyroid Graves' disease during and after methimazole treatment when assessed by IgE and interleukin 13. | 2001 Aug |
|
The effect of methimazole pretreatment on the efficacy of radioactive iodine therapy in Graves' hyperthyroidism: one-year follow-up of a prospective, randomized study. | 2001 Aug |
|
Clinical practice. Subclinical hyperthyroidism. | 2001 Aug 16 |
|
Protracted expression of serotonin transporter and altered thalamocortical projections in the barrelfield of hypothyroid rats. | 2001 Dec |
|
Impact of hyperthyroidism and its correction on vascular reactivity in humans. | 2001 Dec 18 |
|
The systolic function of the left ventricle of the heart in patients with hyperthyroidism during therapy. | 2001 Feb |
|
Antioxidants in the treatment of Graves disease. | 2001 Feb |
|
Effects of thyroid hormones on cardiac structure: a tissue characterization study in patients with thyroid disorders before and after treatment. | 2001 Jul |
|
Cloning, sequencing, tissue distribution, and heterologous expression of rat flavin-containing monooxygenase 3. | 2001 Jul 1 |
|
Interplay of pregnancy, lactation, and hyperthyroidism leading to severe osteoporosis in a young woman. | 2001 Jul-Aug |
|
A case of thyrotoxicosis with pancytopenia. | 2001 Jun |
|
Cross-bridge and calcium behavior in ferret papillary muscle in different thyroid states. | 2001 Jun |
|
Serum levels of cytokines in children and adolescents with Graves' disease and non-toxic nodular goiter. | 2001 Jun |
|
Influence of hypothyroid state on 45Ca(2+) influx and sensitivity of rat uterus to nifedipine and diltiazem. | 2001 Jun 15 |
|
[Effect of thyroxine upon prevention of recurrence of Graves' disease treated with antithyroid drugs]. | 2001 Mar 10 |
|
[Efficacy of quinagolide in the treatment of a patient with hypophyseal resistance to thyroid hormones]. | 2001 May |
|
Bronchial asthma induced by an antithyroid drug. | 2001 May |
|
Method for the analysis of thyreostats in meat tissue using gas chromatography with nitrogen phosphorus detection and tandem mass spectrometric confirmation. | 2001 May |
|
Methimazole-induced pulmonary hemorrhage associated with antimyeloperoxidase-antineutrophil cytoplasmic antibody: a case report. | 2001 Nov |
|
Different role of insulin in GLUT-1 and -4 regulation in heart and skeletal muscle during perinatal hypothyroidism. | 2001 Nov |
|
Apoptosis, necrosis, and cell proliferation induced by S-(1,2-dichlorovinyl)-L-cysteine in primary cultures of human proximal tubular cells. | 2001 Nov 15 |
|
Risk of torsades de pointes from oral erythromycin with concomitant carbimazole (methimazole) administration. | 2001 Oct |
|
Suppression of serum TSH by Graves' Ig: evidence for a functional pituitary TSH receptor. | 2001 Oct |
|
Use of oral cholecystographic agents in the treatment of amiodarone-induced hyperthyroidism. | 2001 Oct |
|
Thyroid hormone-deficient period prior to the onset of hearing is associated with reduced levels of beta-tectorin protein in the tectorial membrane: implication for hearing loss. | 2001 Oct 19 |
|
Thyroid hormone regulates oxidative phosphorylation in the cerebral cortex and striatum of neonatal rats. | 2001 Sep |
|
Ca(2+)/nicotinamide adenine dinucleotide phosphate-dependent H(2)O(2) generation is inhibited by iodide in human thyroids. | 2001 Sep |
|
Neonatal hyperthyroidism in infants of mothers previously thyroidectomized due to Graves' disease. | 2001 Sep-Oct |
|
Severe embryopathy and exposure to methimazole in early pregnancy. | 2002 Feb |
|
Cell necrosis and apoptosis are differentially regulated during goitre development and iodine-induced involution. | 2002 Feb |
|
Influence of hypothyroidism on circulating concentrations and liver expression of IGF-binding proteins mRNA from neonatal and adult rats. | 2002 Feb |
|
Clinical features and outcomes in children with antineutrophil cytoplasmic autoantibody-positive glomerulonephritis associated with propylthiouracil treatment. | 2002 Feb |
|
Depigmentation of brown Guinea pig skin by topical application of methimazole. | 2002 Jan |
|
Severe and mild neonatal hypothyroidism mediate opposite effects on Leydig cells of rats. | 2002 Jan |
|
Identification of active flavin-containing monooxygenase isoform 2 in human lung and characterization of expressed protein. | 2002 Jan |
|
Polarization IR spectra of model crystals containing cyclic N-H...S bonded dimers: 2-mercaptothiazoline and 2-mercapto-1-methylimidazole. | 2002 Jan 15 |
|
Streptozotocin diabetes protects against arrhythmias in rat isolated hearts: role of hypothyroidism. | 2002 Jan 25 |
|
Subclinical hyperthyroidism. | 2002 Jan 3 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/methimazole.html
Usual Adult Dose for Hyperthyroidism
Initial:
Mild hyperthyroidism: 5 mg orally every 8 hours.
Moderately severe hyperthyroidism: 10 mg orally every 8 hours (up to 40 mg per day).
Severe hyperthyroidism: 20 mg orally every 8 hours.
Maintenance:
5 to 15 mg orally daily.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11243251
Methimazole had the strongest antioxidative properties in human erythrocytes at the concentration level of 0.5 mM
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Classification Tree | Code System | Code | ||
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IARC | Methimazole | ||
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LIVERTOX |
NBK548406
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CFR |
21 CFR 520.1372
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EPA PESTICIDE CODE |
600093
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NDF-RT |
N0000175918
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FDA ORPHAN DRUG |
539116
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WHO-ATC |
H03BB52
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WHO-ATC |
H03BB02
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NDF-RT |
N0000175917
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WHO-VATC |
QH03BB02
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FDA ORPHAN DRUG |
523216
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WHO-VATC |
QH03BB52
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NCI_THESAURUS |
C885
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6649
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100000082416
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DB00763
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SUB10967MIG
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C641
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DTXSID4020820
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3361
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6835
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1745
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1411005
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60-56-0
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554Z48XN5E
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CHEMBL1515
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38608
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50673
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D008713
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Methimazole
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554Z48XN5E
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4198
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200-482-4
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M7313
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PRIMARY | Merck Index | ||
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1349907
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METHIMAZOLE
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PRIMARY |
ACTIVE MOIETY