U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of METHIMAZOLE

SMILES

Cn1ccnc1S

InChI

InChIKey=PMRYVIKBURPHAH-UHFFFAOYSA-N
InChI=1S/C4H6N2S/c1-6-3-2-5-4(6)7/h2-3H,1H3,(H,5,7)

HIDE SMILES / InChI

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

Description
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

Curator's Comment:: In 1949, Stanley and Astwood first introduced methimazole

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Tapazole

Approved Use

TAPAZOLE 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

Cmax

ValueDoseCo-administeredAnalytePopulation
248 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
1661 μg × h/L
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
5.3 h
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
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

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​
PubMed

PubMed

TitleDatePubMed
[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

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
Methimazole had the strongest antioxidative properties in human erythrocytes at the concentration level of 0.5 mM
Substance Class Chemical
Created
by admin
on Fri Jun 25 20:56:55 UTC 2021
Edited
by admin
on Fri Jun 25 20:56:55 UTC 2021
Record UNII
554Z48XN5E
Record Status Validated (UNII)
Record Version
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Name Type Language
METHIMAZOLE
HSDB   MI   ORANGE BOOK   USP   USP-RS   VANDF  
Common Name English
1-METHYLIMIDAZOLE-2-THIOL
Systematic Name English
METHIMAZOLE [MI]
Common Name English
METHIMAZOLE [VANDF]
Common Name English
METHIMAZOLE [ORANGE BOOK]
Common Name English
METHIMAZOLE [USP-RS]
Common Name English
NSC-38608
Code English
2H-IMIDAZOLE-2-THIONE, 1,3-DIHYDRO-1-METHYL-
Systematic Name English
TAPAZOLE
Brand Name English
THIAMAZOLE [MART.]
Common Name English
THIAMAZOLE
EP   INN   MART.   WHO-DD  
INN  
Official Name English
THIAMAZOLE [EP MONOGRAPH]
Common Name English
THIAMAZOLE [INN]
Common Name English
MERCAPTIZOLE
Brand Name English
METHIMAZOLE [USP MONOGRAPH]
Common Name English
THIAMAZOLE [WHO-DD]
Common Name English
METHIMAZOLE [HSDB]
Common Name English
METHIMAZOLE [IARC]
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
IUPHAR
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
USP_CATALOG
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
DRUG BANK
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
EVMPD
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
NCI_THESAURUS
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
EPA CompTox
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
HSDB
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
RXCUI
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
DRUG CENTRAL
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
CAS
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
FDA UNII
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
ChEMBL
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
MESH
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
LACTMED
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
INN
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
ECHA (EC/EINECS)
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
MERCK INDEX
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
PUBCHEM
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
WIKIPEDIA
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