Details of the Drug

General Information of Drug (ID: DM25FL8)

Drug Name

Methimazole

Synonyms

methimazole; 60-56-0; thiamazole; Tapazole; 2-Mercapto-1-methylimidazole; Mercazolyl; 1-Methylimidazole-2-thiol; Thymidazole; Mercazole; Methimazol; Thymidazol; Thiamazol; Metazolo; Thycapzol; Metothyrine; Metothyrin; Merkazolil; Mercaptazole; Strumazol; Favistan; Basolan; Thycapsol; Metotirin; Danantizol; Thacapzol; Merkastan; Frentirox; Metizol; Tiamazol; Mercasolyl; 1-Methyl-1H-imidazole-2-thiol; Methylmercaptoimidazole; 1-Methyl-2-mercaptoimidazole; Methiamazole; Usaf el-30; Methimazolum; Mercazolylum; Tapuzole; Metimazol; Thimazole; Basolan; MMZ; Mercazol; Methamazole; Methizol; Methymazol; Metisol; Strumazole; Thiamazole; Thiamazolum; Thimazol; Thyrozol; Tiamazolo; Tirodril; EliLilly Brand of Methimazole; Estedi Brand of Methimazole; Henning Berlin Brand of Methimazole; Hexal Brand of Methimazole; Jones Brand of Methimazole; Merck Brand of Methimazole; Nourypharma Brand of Methimazole; Philopharm Brand of Methimazole; Sanofi Synthelabo Brand of Methimazole; Temmler Brand of Methimazole; Thiamazol Henning; Thiamazol Hexal; Tiamazolo [DCIT]; M0868; Henning, Thiamazol; Hexal, Thiamazol; Methimazole (USP); Methimazole [USAN:BAN]; Tapazole (TN); Thiamazol [INN-French]; Thiamazolum [INN-Latin]; Tiamazol [INN-Spanish]; Mestinon, Regonol, Pyridostigmine Bromide;Thiamazole (JP15/INN); N-Methyl-2-mercaptoimidazole; 1 Methyl 2 mercaptoimidazole; 1,3-Dihydro-1-Methyl-2H-Imidazol-2-Thione; 1,3-Dihydro-1-methyl-2H-imidazole-2-thione; 1-METHYL-1,3-DIHYDRO-2H-IMIDAZOLE-2-THIONE; 1-Methyl-1,3-dihydroimidazole-2-thione; 1-Methyl-2-Imidazolethione; 1-Methyl-2-imidazolethiol; 1-Methyl-imidazole-2-thiol; 1-Methylimidazole-2(3H)-thione; 1-Metylo 2 merkaptoimidazolem; 1-Metylo 2 merkaptoimidazolem [Polish]; 2-Mercaptomethylimidazole; 3-methyl-1H-imidazole-2-thione

Indication

Disease Entry	ICD 11	Status	REF
Hyperthyroidism	5A02	Approved	[1]
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Therapeutic Class

Antithyroid Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

114.17

Logarithm of the Partition Coefficient (xlogp)

-0.3

Rotatable Bond Count (rotbonds)

0

Hydrogen Bond Donor Count (hbonddonor)

1

Hydrogen Bond Acceptor Count (hbondacc)

1

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [2]
Bioavailability: 93% of drug becomes completely available to its intended biological destination(s) [3]
Clearance: The drug present in the plasma can be removed from the body at the rate of 3.7 mL/min/kg [4]
Half-life: The concentration or amount of drug in body reduced by one-half in 2.4 hours [4]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 8.75888 micromolar/kg/day [5]
Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.86 L/kg [4]

Chemical Identifiers

Formula: C4H6N2S
IUPAC Name: 3-methyl-1H-imidazole-2-thione
Canonical SMILES: CN1C=CNC1=S
InChI: InChI=1S/C4H6N2S/c1-6-3-2-5-4(6)7/h2-3H,1H3,(H,5,7)
InChIKey: PMRYVIKBURPHAH-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 1349907
ChEBI ID: CHEBI:50673
CAS Number: 60-56-0
DrugBank ID: DB00763
TTD ID: D0S4BR
VARIDT ID: DR00667
ACDINA ID: D00410

Combinatorial Drugs (CBD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Thyroid peroxidase (TPO)	TT52XDZ	PERT_HUMAN	Inhibitor	[6]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Dimethylaniline oxidase 2 (FMO2)_{Main DME}	DEIASEZ	FMO2_HUMAN	Substrate	[7]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMGCR)	OTRT3F3U	HMDH_HUMAN	Gene/Protein Processing	[8]
Albumin (ALB)	OTVMM513	ALBU_HUMAN	Gene/Protein Processing	[8]
Alpha-fetoprotein (AFP)	OT9GG3ZI	FETA_HUMAN	Gene/Protein Processing	[8]
Angiotensin-converting enzyme 2 (ACE2)	OTTRZGU7	ACE2_HUMAN	Gene/Protein Processing	[9]
Bile salt export pump (ABCB11)	OTRU7THO	ABCBB_HUMAN	Gene/Protein Processing	[10]
C-C motif chemokine 2 (CCL2)	OTAD2HEL	CCL2_HUMAN	Gene/Protein Processing	[11]
Caspase-3 (CASP3)	OTIJRBE7	CASP3_HUMAN	Gene/Protein Processing	[8]
Catalase (CAT)	OTHEBX9R	CATA_HUMAN	Gene/Protein Processing	[12]
Consortin (CNST)	OTOUCB98	CNST_HUMAN	Gene/Protein Processing	[11]
Cytochrome P450 2A6 (CYP2A6)	OT52TWG3	CP2A6_HUMAN	Regulation of Drug Effects	[13]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

Hyperthyroidism

ICD Disease Classification

5A02

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Thyroid peroxidase (TPO)	DTT	TPO	3.83E-01	1.09	1.43

Molecular Expression Atlas (MEA)

MEA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Methimazole (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Remdesivir	DMBFZ6L	Moderate	Increased risk of hepatotoxicity by the combination of Methimazole and Remdesivir.	1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019]	[14]
Bedaquiline	DM3906J	Moderate	Increased risk of hepatotoxicity by the combination of Methimazole and Bedaquiline.	Antimicrobial drug resistance [MG50-MG52]	[15]
Pexidartinib	DMS2J0Z	Major	Increased risk of hepatotoxicity by the combination of Methimazole and Pexidartinib.	Bone/articular cartilage neoplasm [2F7B]	[16]
Cannabidiol	DM0659E	Moderate	Increased risk of hepatotoxicity by the combination of Methimazole and Cannabidiol.	Epileptic encephalopathy [8A62]	[17]
Brentuximab vedotin	DMWLC57	Moderate	Increased risk of hepatotoxicity by the combination of Methimazole and Brentuximab vedotin.	Hodgkin lymphoma [2B30]	[18]
Mipomersen	DMGSRN1	Major	Increased risk of hepatotoxicity by the combination of Methimazole and Mipomersen.	Hyper-lipoproteinaemia [5C80]	[19]
Teriflunomide	DMQ2FKJ	Major	Increased risk of hepatotoxicity by the combination of Methimazole and Teriflunomide.	Hyper-lipoproteinaemia [5C80]	[20]
BMS-201038	DMQTAGO	Major	Increased risk of hepatotoxicity by the combination of Methimazole and BMS-201038.	Hyper-lipoproteinaemia [5C80]	[21]
Calaspargase pegol	DMQZBXI	Moderate	Increased risk of hepatotoxicity by the combination of Methimazole and Calaspargase pegol.	Malignant haematopoietic neoplasm [2B33]	[22]
Idelalisib	DM602WT	Moderate	Increased risk of hepatotoxicity by the combination of Methimazole and Idelalisib.	Mature B-cell leukaemia [2A82]	[23]
Leflunomide	DMR8ONJ	Major	Increased risk of hepatotoxicity by the combination of Methimazole and Leflunomide.	Rheumatoid arthritis [FA20]	[20]
Trabectedin	DMG3Y89	Moderate	Increased risk of hepatotoxicity by the combination of Methimazole and Trabectedin.	Solid tumour/cancer [2A00-2F9Z]	[17]
Prednisolone	DMQ8FR2	Moderate	Increased metabolism of Methimazole caused by Prednisolone mediated induction of CYP450 enzyme.	Solid tumour/cancer [2A00-2F9Z]	[14]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Methimazole 10 mg tablet	10 mg	Oral Tablet	Oral
Methimazole 5 mg tablet	5 mg	Oral Tablet	Oral

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References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 6649).
2	BDDCS predictions, self-correcting aspects of BDDCS assignments, BDDCS assignment corrections, and classification for more than 175 additional drugs
3	Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
4	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
6	Diagnosis and treatment of thyrotoxicosis in childhood. A European questionnaire study. Eur J Endocrinol. 1994 Nov;131(5):467-73.
7	Drug metabolism by flavin-containing monooxygenases of human and mouse. Expert Opin Drug Metab Toxicol. 2017 Feb;13(2):167-181.
8	Low-expressional IGF1 mediated methimazole-induced liver developmental toxicity in fetal mice. Toxicology. 2018 Sep 1;408:70-79. doi: 10.1016/j.tox.2018.07.004. Epub 2018 Jul 7.
9	Effect of common medications on the expression of SARS-CoV-2 entry receptors in liver tissue. Arch Toxicol. 2020 Dec;94(12):4037-4041. doi: 10.1007/s00204-020-02869-1. Epub 2020 Aug 17.
10	Blood cell oxidative stress precedes hemolysis in whole blood-liver slice co-cultures of rat, dog, and human tissues. Toxicol Appl Pharmacol. 2010 May 1;244(3):354-65. doi: 10.1016/j.taap.2010.01.017. Epub 2010 Feb 6.
11	Monitoring of deiodinase deficiency based on transcriptomic responses in SH-SY5Y cells. Arch Toxicol. 2013 Jun;87(6):1103-13. doi: 10.1007/s00204-013-1018-4. Epub 2013 Feb 10.
12	Hepatocellular peroxisomes in human alcoholic and drug-induced hepatitis: a quantitative study. Hepatology. 1991 Nov;14(5):811-7.
13	Role of CYP2A6 in Methimazole Bioactivation and Hepatotoxicity. Chem Res Toxicol. 2021 Dec 20;34(12):2534-2539. doi: 10.1021/acs.chemrestox.1c00300. Epub 2021 Nov 17.
14	Cerner Multum, Inc. "Australian Product Information.".
15	Product Information. Sirturo (bedaquiline). Janssen Pharmaceuticals, Titusville, NJ.
16	Product Information. Turalio (pexidartinib). Daiichi Sankyo, Inc., Parsippany, NJ.
17	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
18	Product Information. Adcetris (brentuximab vedotin). Seattle Genetics Inc, Bothell, WA.
19	Product Information. Kynamro (mipomersen). Genzyme Corporation, Cambridge, MA.
20	Canadian Pharmacists Association.
21	Product Information. Juxtapid (lomitapide). Aegerion Pharmaceuticals Inc, Cambridge, MA.
22	Al-Nawakil C, Willems L, Mauprivez C, et.al "Successful treatment of l-asparaginase-induced severe acute hepatotoxicity using mitochondrial cofactors." Leuk Lymphoma 55 (2014): 1670-4. [PMID: 24090500]
23	Product Information. Zydelig (idelalisib). Gilead Sciences, Foster City, CA.