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

Details

Stereochemistry ACHIRAL
Molecular Formula C4H6N2S
Molecular Weight 114.169
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHIMAZOLE

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)

HIDE SMILES / InChI

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

1950
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
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
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
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
Variable effects of goitrogens in inducing precocious metamorphosis in sea lampreys (Petromyzon marinus).
2001 Apr 15
[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
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
[Long-term results of ultrasound-guided ethanol injections in patients with autonomous thyroid nodules and hyperthyroidism].
2001 Aug 15
The systolic function of the left ventricle of the heart in patients with hyperthyroidism during therapy.
2001 Feb
Side-effects of iodized oil administration in patients with simple goiter.
2001 Feb
Hyperthyroid dementia: clinicoradiological findings and response to treatment.
2001 Feb 15
[Arthritis and antithyroid agents].
2001 Feb 28
Impact of neonatal hypothyroidism on Leydig cell number, plasma, and testicular interstitial fluid sex steroids concentration.
2001 Feb-May
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
Purification and catalytic properties of the chlorophenol 4-monooxygenase from Burkholderia cepacia strain AC1100.
2001 Jun 11
Neuronal expression of synaptotagmin-related gene 1 is regulated by thyroid hormone during cerebellar development.
2001 Jun 15
Effect of chronic oral administration of a low dose of captopril on sodium appetite of hypothyroid rats. Influence of aldosterone treatment.
2001 Mar
[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
Thyroid storm in a child following radioactive iodine (RAI) therapy: a consequence of RAI versus withdrawal of antithyroid medication.
2001 May
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
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
Thyroid hormones modify susceptibility to lidocaine-kindling in rats.
2001 Oct 19
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
Antithyroid drugs as a factor influencing the outcome of radioiodine therapy in Graves' disease and toxic nodular goitre?
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
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
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

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
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 [WHO-DD]
Common Name English
thiamazole [INN]
Common Name English
MERCAPTIZOLE
Brand Name English
METHIMAZOLE [USP MONOGRAPH]
Common Name English
METHIMAZOLE [HSDB]
Common Name English
METHIMAZOLE [IARC]
Common Name English
THIAMAZOLE [JAN]
Common Name English
Classification Tree Code System Code
IARC Methimazole
LIVERTOX NBK548406
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CFR 21 CFR 520.1372
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
EPA PESTICIDE CODE 600093
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
NDF-RT N0000175918
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FDA ORPHAN DRUG 539116
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
WHO-ATC H03BB52
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
WHO-ATC H03BB02
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
NDF-RT N0000175917
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
WHO-VATC QH03BB02
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
FDA ORPHAN DRUG 523216
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
WHO-VATC QH03BB52
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NCI_THESAURUS C885
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
Code System Code Type Description
IUPHAR
6649
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PRIMARY
SMS_ID
100000082416
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PRIMARY
DRUG BANK
DB00763
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PRIMARY
EVMPD
SUB10967MIG
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
PRIMARY
NCI_THESAURUS
C641
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
PRIMARY
EPA CompTox
DTXSID4020820
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PRIMARY
HSDB
3361
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
PRIMARY
RXCUI
6835
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
PRIMARY RxNorm
DRUG CENTRAL
1745
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PRIMARY
RS_ITEM_NUM
1411005
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PRIMARY
CAS
60-56-0
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
PRIMARY
FDA UNII
554Z48XN5E
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
PRIMARY
ChEMBL
CHEMBL1515
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
PRIMARY
NSC
38608
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PRIMARY
CHEBI
50673
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
PRIMARY
MESH
D008713
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
PRIMARY
LACTMED
Methimazole
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
PRIMARY
DAILYMED
554Z48XN5E
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
PRIMARY
INN
4198
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PRIMARY
ECHA (EC/EINECS)
200-482-4
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
PRIMARY
MERCK INDEX
m7313
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
PRIMARY Merck Index
PUBCHEM
1349907
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
PRIMARY
WIKIPEDIA
METHIMAZOLE
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
PRIMARY