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]
Therapeutic Class
Antithyroid Agents
Affected Organisms
Humans and other mammals
ATC Code
H03BB02: Methimazole
H03BB: Sulfur-containing imidazole derivatives
H03B: ANTITHYROID PREPARATIONS
H03: THYROID THERAPY
H: SYSTEMIC HORMONAL PREPARATIONS, EXCL. SEX HORMONES AND INSULINS
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
CHEMBL1515
CAS Number
60-56-0
UNII
554Z48XN5E
DrugBank ID
DB00763
TTD ID
D0S4BR
VARIDT ID
DR00667
ACDINA ID
D00410
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

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]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Dimethylaniline oxidase 2 (FMO2)
Main DME 		DEIASEZ FMO2_HUMAN Substrate [7]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Albumin (ALB) OTVMM513 ALBU_HUMAN Gene/Protein Processing [8]
Bile salt export pump (ABCB11) OTRU7THO ABCBB_HUMAN Gene/Protein Processing [9]
C-C motif chemokine 2 (CCL2) OTAD2HEL CCL2_HUMAN Gene/Protein Processing [10]
Consortin (CNST) OTOUCB98 CNST_HUMAN Gene/Protein Processing [10]
DNA-binding protein inhibitor ID-3 (ID3) OTUULW5Z ID3_HUMAN Gene/Protein Processing [10]
Flavin-containing monooxygenase 1 (FMO1) OTTHSQKP FMO1_HUMAN Biotransformations [11]
Flavin-containing monooxygenase 2 (FMO2) OTUJUL9S FMO2_HUMAN Biotransformations [12]
Flavin-containing monooxygenase 3 (FMO3) OT1G2EV3 FMO3_HUMAN Regulation of Drug Effects [13]
Integrin beta-5 (ITGB5) OT21MF51 ITB5_HUMAN Gene/Protein Processing [10]
Interleukin-8 (CXCL8) OTS7T5VH IL8_HUMAN Gene/Protein Processing [9]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

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) Jump to Detail Molecular Expression Atlas of This Drug

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]
⏷ Show the Full List of 13 DDI Information of This Drug

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
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
Jump to Detail Pharmaceutical Formulation Page of This Drug

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 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.
10 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.
11 Evaluation of xenobiotic N- and S-oxidation by variant flavin-containing monooxygenase 1 (FMO1) enzymes. Toxicol Sci. 2004 Apr;78(2):196-203.
12 Haplotype and functional analysis of four flavin-containing monooxygenase isoform 2 (FMO2) polymorphisms in Hispanics. Pharmacogenet Genomics. 2005 Apr;15(4):245-56. doi: 10.1097/01213011-200504000-00008.
13 Identification and functional analysis of common human flavin-containing monooxygenase 3 genetic variants. J Pharmacol Exp Ther. 2007 Jan;320(1):266-73. doi: 10.1124/jpet.106.112268. Epub 2006 Oct 18.
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.