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Compound Summary

General Compound Information

Methimazole

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Description

Methimazole is a member of the class of imidazoles that it imidazole-2-thione in which a methyl group replaces the hydrogen which is attached to a nitrogen. It has a role as an antithyroid drug.

Synonyms

methimazole; 60-56-0; thiamazole; Tapazole; 2-Mercapto-1-methylimidazole;

1-Methylimidazole-2-thiol;Mercazolyl;Favistan;Mercazole;Metazolo;Methimazol;Thymidazol;Thymidazole;1-Methyl-1H-imidazole-2-thiol;Mercaptazole;Merkazolil;Metothyrin;Metothyrine;Strumazol;Thiamazol;Thycapzol;Basolan;Danantizol;Frentirox;Merkastan;Metotirin;Thacapzol;Thycapsol;Metizol;Mercasolyl;Methylmercaptoimidazole;1-Methyl-2-mercaptoimidazole;Methiamazole;3-methyl-1H-imidazole-2-thione;Usaf el-30;2H-Imidazole-2-thione, 1,3-dihydro-1-methyl-;N-Methyl-2-mercaptoimidazole;Tapuzole;Thimazole;1-Methyl-1H-imidazole-2(3H)-thione;1-Methyl-2-imidazolethiol;1-METHYL-1,3-DIHYDRO-2H-IMIDAZOLE-2-THIONE;2-Mercaptomethylimidazole;1,3-Dihydro-1-methyl-2H-imidazole-2-thione;1-Methylimidazole-2(3H)-thione;Imidazole-2-thiol, 1-methyl-;1-Metylo 2 merkaptoimidazolem;Mercaptizole;1-Methyl-1,3-dihydroimidazole-2-thione;4-Imidazoline-2-thione, 1-methyl-;MFCD00179321;Thiamazole [INN];Methimazole (USP);Methimazole [USP];NSC-38608;Tiamazol;CHEMBL1515;Mercazolylum;Methimazolum;DTXSID4020820;Metimazol;1-methyl-2,3-dihydro-1H-imidazole-2-thione;CHEBI:50673;Imidazole, 1-methyl-2-mercapto-;554Z48XN5E;NSC38608;223768-14-7;CAS-60-56-0;Tiamazolo [DCIT];NCGC00016273-01;Methamazole;Thiamazolum;Strumazole;Tiamazolo;Thiamazol [INN-French];Tiamazol [INN-Spanish];Thiamazolum [INN-Latin];85916-84-3;MMZ;DTXCID20820;Felimazole;Tapazole (TN);SMR000058376;1-Metylo 2 merkaptoimidazolem [Polish];HSDB 3361;SR-05000001672;EINECS 200-482-4;NSC 38608;1-Methyl-imidazole-2-thiol;tiamazole;UNII-554Z48XN5E;AI3-60285;1,3-Dihydro-1-Methyl-2H-Imidazol-2-Thione;Thiamazole,(S);2-Mercapto-1-methyl-1H-imidazole;Prestwick_1010;Spectrum_000995;METHIMAZOLE [MI];THIAMAZOLE [JAN];Prestwick0_000786;Prestwick1_000786;Prestwick2_000786;Prestwick3_000786;Spectrum2_001273;Spectrum3_000495;Spectrum4_000048;Spectrum5_000954;M0868;METHIMAZOLE [HSDB];METHIMAZOLE [IARC];Thiamazole (JP17/INN);1-methylimidazole-2-thione;METHIMAZOLE [VANDF];Methimazole-d3(methyl-d3);N-methyl imidazole-2-thiol;THIAMAZOLE [MART.];2-mecapto 1-methylimidazole;2-Mercapto-1-methylimidazol;THIAMAZOLE [WHO-DD];2-mercapto-N-methylimidazole;SCHEMBL41647;2-mercapto-3-methylimidazole;BSPBio_000892;BSPBio_001989;KBioGR_000515;KBioSS_001475;METHIMAZOLE [USP-RS];MLS000028413;MLS002548853;BIDD:GT0163;DivK1c_000188;SPECTRUM1500396;WLN: T5N CNJ A BSH;1-methyl-2-mercapto-imidazole;2-mercapto-1-methyl-imidazole;SPBio_001266;SPBio_002831;1-Methyl-2-mercapto imidazole;Imidazole-2-thio, 1-methyl-;BPBio1_000982;GTPL6649;Methimazole, analytical standard;Methimazole (Tapazole, Northyx);1-methyl-1H-immidazole-2-thiol;1-methyl-3H-imidazole-2-thione;HMS500J10;KBio1_000188;KBio2_001475;KBio2_004043;KBio2_006611;KBio3_001489;METHIMAZOLE [ORANGE BOOK];THIAMAZOLE [EP MONOGRAPH];1-methyl-1-H-imidazole-2-thiol;NINDS_000188;HMS1570M14;HMS1920L17;HMS2090B17;HMS2091D12;HMS2094C05;HMS2097M14;HMS3259L09;HMS3651I13;HMS3714M14;Pharmakon1600-01500396;METHIMAZOLE [USP MONOGRAPH];1-Methyl-1H-imidazole-2-thiol #;AMY11202;BCP02147;HY-B0208;STR03572;ZINC1187543;Tox21_110341;Tox21_201341;Tox21_300532;AC-785;BDBM50241361;CCG-39656;NSC757111;s1609;STK300018;STK802184;AKOS000119427;AKOS000269708;Tox21_110341_1;BS-3743;CCG-220786;DB00763;NC00636;NSC-757111;2-Mercapto-1-methylimidazole, >=99%;IDI1_000188;NCGC00016273-02;NCGC00016273-03;NCGC00094721-01;NCGC00094721-02;NCGC00094721-03;NCGC00094721-04;NCGC00094721-05;NCGC00094721-06;NCGC00094721-07;NCGC00178875-01;NCGC00254307-01;NCGC00258893-01;Methimazol 100 microg/mL in Acetonitrile;SBI-0206922.P001;SBI-0206922.P004;DB-053649;2H-Imidazole-2-thione,3-dihydro-1-methyl-;FT-0603253;SW197088-3;EN300-18327;C07190;D00401;H10722;AB00443630-03;AB00443630-04;AB00443630_06;AB00443630_07;Methimazole, VETRANAL(TM), analytical standard;A832780;Q419663;SR-01000695434;Q-201364;SR-01000695434-2;SR-05000001672-1;SR-05000001672-2;BRD-K54416256-001-15-7;Z57901905;F0001-2396;F1679-0258;Thiamazole, European Pharmacopoeia (EP) Reference Standard;Methimazole, United States Pharmacopeia (USP) Reference Standard;

FlavorDB ID

33

PUBCHEM ID

1349907

Molecular Weight

114.17

Molecular Formula

C4H6N2S

Openeye Can Smiles

CN1C=CNC1=S

IUPAC Inchikey

PMRYVIKBURPHAH-UHFFFAOYSA-N

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Similarity

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Compound Classification

Classification (Parent Nodes)

ClassyFire Ontology

Compound Quality

Quality information of this compound is not available!

Compound Toxicity and Food Additive Safety (OFAS)

Toxicity Summary
Link to the Distributed Structure-Searchable Toxicity (DSSTox) Database
The oral LD50 of methimazole in rats is 2250 mg/kg.[L8333] Signs and symptoms of methimazole overdose may include gastrointestinal distress, headache, fever, joint pain, pruritus, and edema. More serious adverse effects, such as aplastic anemia or agranulocytosis, may manifest within hours to days.[L8336,L8339] Hepatitis, nephrotic syndrome, exfoliative dermatitis, and CNS effects such as neuropathy or CNS depression/stimulation are also potential, albeit less frequent, results of overdose.[L8336,L8339] Management of overdose involves supportive treatment as dictated by the patient"s status.[L8336,L8339] This may involve monitoring of the patient"s vital signs, blood gases, serum electrolytes, or bone marrow function as indicated.[L8339]
Source: DrugBank or Hazardous Substances Data Bank (HSDB)

Receptors

Receptor	REFERENCE	EC50 [µM]	Effective Concentration [µM]
TAS2R38	details	Activated

Consensus Spectra

Spectrum Type	Spectrum View	Description	Polarity
Experimental LCMS	view	LCMS_Positive	positive