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)
Molecular Formula | C4H6N2S |
Molecular Weight | 114.169 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
---|---|---|
Sequencing, expression, and characterization of cDNA expressed flavin-containing monooxygenase 2 from mouse. | 2001 |
|
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 |
|
Role of thyroid hormones in the maturation and organisation of rat barrel cortex. | 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 |
|
[Graves-Basedow disease associated with unusual variation of thyroid papillary carcinoma: a clinical case]. | 2001 Apr-Jun |
|
Estimation of antithyroid drug dose in Graves' disease: value of quantification of thyroid blood flow with color duplex sonography. | 2001 Aug |
|
[Long-term results of ultrasound-guided ethanol injections in patients with autonomous thyroid nodules and hyperthyroidism]. | 2001 Aug 15 |
|
Clinical practice. Subclinical hyperthyroidism. | 2001 Aug 16 |
|
Protracted expression of serotonin transporter and altered thalamocortical projections in the barrelfield of hypothyroid rats. | 2001 Dec |
|
Hypothyroidism induces type I iodothyronine deiodinase expression in tilapia liver. | 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 |
|
A case of thyrotoxicosis with pancytopenia. | 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 |
|
Methimazole-induced pulmonary hemorrhage associated with antimyeloperoxidase-antineutrophil cytoplasmic antibody: a case report. | 2001 Nov |
|
Hyperemesis gravidarum associated with thyrotoxicosis and a past history of an eating disorder. | 2001 Nov |
|
Influence of nicotinamide on the radiosensitivity of normal and goitrous thyroid in the rat. | 2001 Nov |
|
Adverse effects of prenatal methimazole exposure. | 2001 Nov |
|
Effect of eicosapentaenoic acid ethyl ester on hypothyroid function. | 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 |
|
Effects of neonatal hypothyroidism on the expressions of growth cone proteins and axon guidance molecules related genes in the hippocampus. | 2001 Nov 26 |
|
Severe myocardial ischemia following hormone replacement in two cases of hypothyroidism with normal coronary arteriogram. | 2001 Oct |
|
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 |
|
Selective effect of hypothyroidism on expression of myelin markers during development. | 2001 Oct 15 |
|
Thyroid hormones modify susceptibility to lidocaine-kindling in rats. | 2001 Oct 19 |
|
Antithyroid drugs as a factor influencing the outcome of radioiodine therapy in Graves' disease and toxic nodular goitre? | 2001 Sep |
|
Effect of losartan on sodium appetite of hypothyroid rats subjected to water and sodium depletion and water, sodium and food deprivation. | 2001 Sep |
|
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 |
|
The effect of methimazole on thyroid uptake of pertechnetate and radioiodine in normal cats. | 2001 Sep-Oct |
|
Neonatal hyperthyroidism in infants of mothers previously thyroidectomized due to Graves' disease. | 2001 Sep-Oct |
|
Dermatomyositis and 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 |
|
Teratogen update: antithyroid drugs-methimazole, carbimazole, and propylthiouracil. | 2002 Jan |
|
Methimazole-induced asthma? | 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
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 16:03:04 UTC 2022
by
admin
on
Fri Dec 16 16:03:04 UTC 2022
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Record UNII |
554Z48XN5E
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Record Status |
Validated (UNII)
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Record Version |
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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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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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TRANSPORTER -> INHIBITOR |
Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (GC)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (GC)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (GC)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |