ContaminantDB: Methimazole

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-20 16:10:35 UTC

Update Date

2016-11-09 01:15:19 UTC

Accession Number

CHEM016009

Identification

Common Name

Methimazole

Class

Small Molecule

Description

Methimazole is a thionamide antithyroid agent that inhibits the synthesis of thyroid hormones. It was first introduced as an antithyroid agent in 1949 and is now commonly used in the management of hyperthyroidism, particularly in those for whom more aggressive options such as surgery or radioactive iodine therapy are inappropriate. On a weight basis, methimazole is 10 times more potent than the other major antithyroid thionamide used in North America, , and is the active metabolite of the pro-drug , which is an antithyroid medication used in the United Kingdom and parts of the former British Commonwealth. Traditionally, methimazole has been preferentially used over propylthiouracil due to the risk of fulminant hepatotoxicity carried by the latter, with propylthiouracil being preferred in pregnancy due to a perceived lower risk of teratogenic effects. Despite documented teratogenic effects in its published labels, the true teratogenicity of methimazole appears to be unclear and its place in therapy may change in the future.

Contaminant Sources

HMDB Contaminants - Urine
IARC Carcinogens Group 3
STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-METHYL-1,3-dihydro-2H-imidazole-2-thione	ChEBI
1-Methylimidazole-2(3H)-thione	ChEBI
Danantizol	ChEBI
Favistan	ChEBI
Strumazol	ChEBI
Tapazole	ChEBI
Thacapzol	ChEBI
Thiamazol	ChEBI
Thiamazole	ChEBI
Thiamazolum	ChEBI
Tiamazol	ChEBI
USAF el-30	ChEBI
Mercaptazole	HMDB
Mercasolyl	HMDB
Mercazole	HMDB
Mercazolyl	HMDB
Merkazolil	HMDB
Metazolo	HMDB
Methamazole	HMDB
Methiamazole	HMDB
Methimazol	HMDB
Metothyrin	HMDB
Metothyrine	HMDB
Thimazole	HMDB
Thymidazol	HMDB
Thymidazole	HMDB
1 Methyl 2 mercaptoimidazole	HMDB
1-Methyl-2-mercaptoimidazole	HMDB
Mercazol	HMDB
Metisol	HMDB
Nourypharma brand OF methimazole	HMDB
Philopharm brand OF methimazole	HMDB
Eli lilly brand OF methimazole	HMDB
Henning, thiamazol	HMDB
Merck brand OF methimazole	HMDB
Methylmercaptoimidazole	HMDB
Methymazol	HMDB
Sanofi synthelabo brand OF methimazole	HMDB
Thiamazol hexal	HMDB
Tirodril	HMDB
Estedi brand OF methimazole	HMDB
Henning berlin brand OF methimazole	HMDB
Hexal, thiamazol	HMDB
Methizol	HMDB
Metizol	HMDB
Thiamazol henning	HMDB
Thimazol	HMDB
Hexal brand OF methimazole	HMDB
Jones brand OF methimazole	HMDB
Temmler brand OF methimazole	HMDB
Thyrozol	HMDB

Chemical Formula

C₄H₆N₂S

Average Molecular Mass

114.169 g/mol

Monoisotopic Mass

114.025 g/mol

CAS Registry Number

60-56-0

IUPAC Name

1-methyl-2,3-dihydro-1H-imidazole-2-thione

Traditional Name

methimazole

SMILES

CN1C=CNC1=S

InChI Identifier

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

InChI Key

PMRYVIKBURPHAH-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as imidazolethiones. These are aromatic compounds containing an imidazole ring which bears a thioketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azolines

Sub Class

Imidazolines

Direct Parent

Imidazolethiones

Alternative Parents

Substituents

N-substituted imidazole
Imidazole-2-thione
Heteroaromatic compound
Imidazole
Azole
Thiourea
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organosulfur compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

imidazoles (CHEBI:50673 )
thioureas (CHEBI:50673 )
a small molecule (CPD-11282 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	11.3 g/L	ALOGPS
logP	-0.38	ALOGPS
logP	0.75	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	10.41	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	15.27 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	33.23 m³·mol⁻¹	ChemAxon
Polarizability	11.64 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-9400000000-2a587b1850e13e97c2cf	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-066r-8900000000-9230df83b87c13377bfb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-0900000000-275f9771b8d1d7486052	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-0900000000-1763fdc1a812fa765250	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-0900000000-78877e6d65fda61a0e67	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-1900000000-c979e7cdbceb656b6a1e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-1900000000-1447e5774eda5dc3fe26	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-066r-9300000000-41d253a513ee17fed774	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-9000000000-11684a341cebaa28c427	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a60-9000000000-7637560408e70990bc27	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - -1V, Positive	splash10-066r-8900000000-9230df83b87c13377bfb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-014i-0900000000-374ccd1b69e853438841	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0900000000-c6da240ee4f95cf882f2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0900000000-275f9771b8d1d7486052	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-014i-0900000000-1763fdc1a812fa765250	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-fb071a5f16c608333fba	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-78877e6d65fda61a0e67	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-3e543dd0166f52789fcd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0900-9300000000-90c58541a936c6fdd275	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-9a1c61f319838c2ebce9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-022c-9200000000-3ef9cd647246e770cc65	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03k9-9800000000-4cd0298581c2529c50e7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-7f5fe02e4938bb18ff53	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-810e7a010dd805f3251d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-5900000000-e88140069cbfa61f9c51	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-3969b3a3102e9214d562	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum