Details
Stereochemistry | ACHIRAL |
Molecular Formula | C4H6N2S |
Molecular Weight | 114.1701 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cn1ccnc1S
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 | 114.1701 |
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 |
---|---|---|
[Recovery from pancytopenia and liver dysfunction after administration of thiamazole for hyperthyroidism]. | 2000 Nov |
|
Thyroid function and intellectual development of infants nursed by mothers taking methimazole. | 2000 Sep |
|
[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 |
|
Coexistence of Graves' disease and struma ovarii: case report and literature review. | 2001 Apr |
|
A case of pulmonary metastatic thyroid cancer complicated with Graves' disease. | 2001 Apr |
|
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 |
|
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 |
|
Basedow's disease and chronic ulcerative colitis: a case report and review of the Japanese literature. | 2001 Jan |
|
Cloning, sequencing, tissue distribution, and heterologous expression of rat flavin-containing monooxygenase 3. | 2001 Jul 1 |
|
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 |
|
Effect of altered thyroid status on neurotrophin gene expression during postnatal development of the mouse cerebellum. | 2001 Mar |
|
Efficacy of single daily dosage of methimazole vs. propylthiouracil in the induction of euthyroidism. | 2001 Mar |
|
[Effect of thyroxine upon prevention of recurrence of Graves' disease treated with antithyroid drugs]. | 2001 Mar 10 |
|
Clinical, endocrinological and radiography features in a child with McCune-Albright syndrome and pituitary adenoma. | 2001 May |
|
Bronchial asthma induced by an antithyroid drug. | 2001 May |
|
Methimazole-induced pulmonary hemorrhage associated with antimyeloperoxidase-antineutrophil cytoplasmic antibody: a case report. | 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 |
|
Methimazole as an antioxidant and immunomodulator in thyroid cells: mechanisms involving interferon-gamma signaling and H(2)O(2) scavenging. | 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 |
|
Thyroid hormone regulates oxidative phosphorylation in the cerebral cortex and striatum of neonatal rats. | 2001 Sep |
|
The effect of methimazole on thyroid uptake of pertechnetate and radioiodine in normal cats. | 2001 Sep-Oct |
|
Dermatomyositis and Graves' disease. | 2001 Sep-Oct |
|
Clinical features and outcomes in children with antineutrophil cytoplasmic autoantibody-positive glomerulonephritis associated with propylthiouracil treatment. | 2002 Feb |
|
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 |
|
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 Jun 25 20:56:55 UTC 2021
by
admin
on
Fri Jun 25 20:56:55 UTC 2021
|
Record UNII |
554Z48XN5E
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
IARC | Methimazole | ||
|
LIVERTOX |
617
Created by
admin on Fri Jun 25 20:56:55 UTC 2021 , Edited by admin on Fri Jun 25 20:56:55 UTC 2021
|
||
|
CFR |
21 CFR 520.1372
Created by
admin on Fri Jun 25 20:56:55 UTC 2021 , Edited by admin on Fri Jun 25 20:56:55 UTC 2021
|
||
|
EPA PESTICIDE CODE |
600093
Created by
admin on Fri Jun 25 20:56:55 UTC 2021 , Edited by admin on Fri Jun 25 20:56:55 UTC 2021
|
||
|
NDF-RT |
N0000175918
Created by
admin on Fri Jun 25 20:56:55 UTC 2021 , Edited by admin on Fri Jun 25 20:56:55 UTC 2021
|
||
|
FDA ORPHAN DRUG |
539116
Created by
admin on Fri Jun 25 20:56:55 UTC 2021 , Edited by admin on Fri Jun 25 20:56:55 UTC 2021
|
||
|
WHO-ATC |
H03BB52
Created by
admin on Fri Jun 25 20:56:55 UTC 2021 , Edited by admin on Fri Jun 25 20:56:55 UTC 2021
|
||
|
WHO-ATC |
H03BB02
Created by
admin on Fri Jun 25 20:56:55 UTC 2021 , Edited by admin on Fri Jun 25 20:56:55 UTC 2021
|
||
|
NDF-RT |
N0000175917
Created by
admin on Fri Jun 25 20:56:55 UTC 2021 , Edited by admin on Fri Jun 25 20:56:55 UTC 2021
|
||
|
WHO-VATC |
QH03BB02
Created by
admin on Fri Jun 25 20:56:55 UTC 2021 , Edited by admin on Fri Jun 25 20:56:55 UTC 2021
|
||
|
FDA ORPHAN DRUG |
523216
Created by
admin on Fri Jun 25 20:56:55 UTC 2021 , Edited by admin on Fri Jun 25 20:56:55 UTC 2021
|
||
|
WHO-VATC |
QH03BB52
Created by
admin on Fri Jun 25 20:56:55 UTC 2021 , Edited by admin on Fri Jun 25 20:56:55 UTC 2021
|
||
|
NCI_THESAURUS |
C885
Created by
admin on Fri Jun 25 20:56:55 UTC 2021 , Edited by admin on Fri Jun 25 20:56:55 UTC 2021
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
6649
Created by
admin on Fri Jun 25 20:56:55 UTC 2021 , Edited by admin on Fri Jun 25 20:56:55 UTC 2021
|
PRIMARY | |||
|
1411005
Created by
admin on Fri Jun 25 20:56:55 UTC 2021 , Edited by admin on Fri Jun 25 20:56:55 UTC 2021
|
PRIMARY | USP-RS | ||
|
DB00763
Created by
admin on Fri Jun 25 20:56:55 UTC 2021 , Edited by admin on Fri Jun 25 20:56:55 UTC 2021
|
PRIMARY | |||
|
SUB10967MIG
Created by
admin on Fri Jun 25 20:56:55 UTC 2021 , Edited by admin on Fri Jun 25 20:56:55 UTC 2021
|
PRIMARY | |||
|
C641
Created by
admin on Fri Jun 25 20:56:55 UTC 2021 , Edited by admin on Fri Jun 25 20:56:55 UTC 2021
|
PRIMARY | |||
|
60-56-0
Created by
admin on Fri Jun 25 20:56:55 UTC 2021 , Edited by admin on Fri Jun 25 20:56:55 UTC 2021
|
PRIMARY | |||
|
3361
Created by
admin on Fri Jun 25 20:56:55 UTC 2021 , Edited by admin on Fri Jun 25 20:56:55 UTC 2021
|
PRIMARY | |||
|
6835
Created by
admin on Fri Jun 25 20:56:55 UTC 2021 , Edited by admin on Fri Jun 25 20:56:55 UTC 2021
|
PRIMARY | RxNorm | ||
|
1745
Created by
admin on Fri Jun 25 20:56:55 UTC 2021 , Edited by admin on Fri Jun 25 20:56:55 UTC 2021
|
PRIMARY | |||
|
60-56-0
Created by
admin on Fri Jun 25 20:56:55 UTC 2021 , Edited by admin on Fri Jun 25 20:56:55 UTC 2021
|
PRIMARY | |||
|
554Z48XN5E
Created by
admin on Fri Jun 25 20:56:55 UTC 2021 , Edited by admin on Fri Jun 25 20:56:55 UTC 2021
|
PRIMARY | |||
|
CHEMBL1515
Created by
admin on Fri Jun 25 20:56:55 UTC 2021 , Edited by admin on Fri Jun 25 20:56:55 UTC 2021
|
PRIMARY | |||
|
D008713
Created by
admin on Fri Jun 25 20:56:55 UTC 2021 , Edited by admin on Fri Jun 25 20:56:55 UTC 2021
|
PRIMARY | |||
|
Methimazole
Created by
admin on Fri Jun 25 20:56:55 UTC 2021 , Edited by admin on Fri Jun 25 20:56:55 UTC 2021
|
PRIMARY | |||
|
4198
Created by
admin on Fri Jun 25 20:56:55 UTC 2021 , Edited by admin on Fri Jun 25 20:56:55 UTC 2021
|
PRIMARY | |||
|
200-482-4
Created by
admin on Fri Jun 25 20:56:55 UTC 2021 , Edited by admin on Fri Jun 25 20:56:55 UTC 2021
|
PRIMARY | |||
|
M7313
Created by
admin on Fri Jun 25 20:56:55 UTC 2021 , Edited by admin on Fri Jun 25 20:56:55 UTC 2021
|
PRIMARY | Merck Index | ||
|
1349907
Created by
admin on Fri Jun 25 20:56:55 UTC 2021 , Edited by admin on Fri Jun 25 20:56:55 UTC 2021
|
PRIMARY | |||
|
METHIMAZOLE
Created by
admin on Fri Jun 25 20:56:55 UTC 2021 , Edited by admin on Fri Jun 25 20:56:55 UTC 2021
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
TRANSPORTER -> INHIBITOR |
Related Record | Type | Details | ||
---|---|---|---|---|
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (GC)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (GC)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (GC)
EP
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |