thiamazole Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
1745 60-56-0

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • methimazole
  • methylimidazolethiol
  • thyrozol
  • thymidazole
  • thymidazol
  • thycapzol
  • thiamazole
  • tapazole
  • methymazol
A thioureylene antithyroid agent that inhibits the formation of thyroid hormones by interfering with the incorporation of iodine into tyrosyl residues of thyroglobulin. This is done by interfering with the oxidation of iodide ion and iodotyrosyl groups through inhibition of the peroxidase enzyme.
  • Molecular weight: 114.17
  • Formula: C4H6N2S
  • CLOGP: -0.34
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 1
  • TPSA: 15.27
  • ALOGS: -1
  • ROTB: 0

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
10 mg O

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 8.76 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Hosey CM, Chan R, Benet LZ
BA (Bioavailability) 93 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.86 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 3.70 mL/min/kg Lombardo F, Berellini G, Obach RS
t_half (Half-life) 2.40 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
June 21, 1950 FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Agranulocytosis 374.02 13.49 144 8465 22041 46655412
Hyperthyroidism 329.15 13.49 111 8498 11600 46665853
Thyrotoxic crisis 198.59 13.49 42 8567 703 46676750
Hypothyroidism 68.15 13.49 52 8557 31286 46646167
Choanal atresia 63.19 13.49 10 8599 26 46677427
Antithyroid arthritis syndrome 57.55 13.49 8 8601 4 46677449
Exophthalmos 53.47 13.49 16 8593 1129 46676324
Anti-neutrophil cytoplasmic antibody positive vasculitis 41.45 13.49 15 8594 1920 46675533
Toxic nodular goitre 38.68 13.49 6 8603 13 46677440
Goitre 38.27 13.49 19 8590 5312 46672141
Polyarthritis 37.39 13.49 20 8589 6522 46670931
Endocrine ophthalmopathy 32.37 13.49 8 8601 273 46677180
Dysmorphism 30.72 13.49 12 8597 1895 46675558
Pulmonary alveolar haemorrhage 30.37 13.49 15 8594 4147 46673306
Neuroglycopenia 26.29 13.49 5 8604 47 46677406
Oropharyngeal pain 26.01 13.49 48 8561 74120 46603333
Mucocutaneous candidiasis 26.00 13.49 4 8605 8 46677445
Kidney duplex 25.66 13.49 5 8604 54 46677399
Insulin autoimmune syndrome 25.42 13.49 5 8604 57 46677396
Drug-induced liver injury 25.04 13.49 27 8582 25341 46652112
Aplasia cutis congenita 24.53 13.49 5 8604 69 46677384
Rheumatoid arthritis 24.46 13.49 7 8602 240208 46437245
Renal infarct 24.38 13.49 9 8600 1218 46676235
Clinodactyly 22.74 13.49 5 8604 101 46677352
Hypoglycaemia 22.71 13.49 38 8571 54311 46623142
Blood thyroid stimulating hormone decreased 22.25 13.49 12 8597 3977 46673476
Neutropenia 21.88 13.49 67 8542 143137 46534316
Sopor 21.16 13.49 22 8587 19806 46657647
Eosinophilic pleural effusion 20.63 13.49 4 8605 42 46677411
Hypoaldosteronism 19.81 13.49 5 8604 186 46677267
Thyroid haemorrhage 19.64 13.49 4 8605 55 46677398
Toxic goitre 19.50 13.49 3 8606 6 46677447
Autoimmune neutropenia 19.25 13.49 4 8605 61 46677392
Ecthyma 18.98 13.49 5 8604 221 46677232
Hypersensitivity vasculitis 18.92 13.49 11 8598 4210 46673243
Symptom masked 18.27 13.49 6 8603 574 46676879
Atrial fibrillation 18.25 13.49 51 8558 103539 46573914
Pyrexia 18.09 13.49 118 8491 348684 46328769
Drug interaction 17.52 13.49 79 8530 203015 46474438
Jaundice cholestatic 17.14 13.49 11 8598 5018 46672435
Acute generalised exanthematous pustulosis 16.98 13.49 14 8595 9391 46668062
Stevens-Johnson syndrome 16.64 13.49 21 8588 23276 46654177
Microscopic polyangiitis 16.43 13.49 4 8605 128 46677325
Cardiac arrest 16.41 13.49 45 8564 90354 46587099
Metabolic function test abnormal 15.64 13.49 4 8605 157 46677296
Drug intolerance 15.49 13.49 4 8605 147045 46530408
Large for dates baby 15.44 13.49 5 8604 458 46676995
Thyroidectomy 15.39 13.49 6 8603 943 46676510
Respiratory syncytial virus infection 15.07 13.49 10 8599 4825 46672628
Spigelian hernia 14.96 13.49 3 8606 38 46677415
Tonsillitis 14.83 13.49 10 8599 4954 46672499
Haemoptysis 14.71 13.49 21 8588 26168 46651285
Hepatitis cholestatic 14.33 13.49 11 8598 6666 46670787
Febrile neutropenia 14.19 13.49 44 8565 94583 46582870
Kidney transplant rejection 14.02 13.49 9 8600 4109 46673344
Retinal vasculitis 13.61 13.49 5 8604 667 46676786

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Hyperthyroidism 344.87 20.41 94 3246 8004 29941134
Thyrotoxic crisis 67.72 20.41 14 3326 354 29948784
Agranulocytosis 66.12 20.41 37 3303 21905 29927233
Thyrotoxic periodic paralysis 62.32 20.41 10 3330 55 29949083
Kounis syndrome 51.03 20.41 15 3325 1658 29947480
Hypothyroidism 49.93 20.41 27 3313 14936 29934202
Polymerase chain reaction 46.02 20.41 8 3332 76 29949062
Goitre 39.19 20.41 12 3328 1524 29947614
Urine leukocyte esterase positive 34.96 20.41 8 3332 328 29948810
Albumin urine present 33.77 20.41 8 3332 382 29948756
Haemoglobinuria 30.95 20.41 8 3332 548 29948590
Mouth swelling 30.46 20.41 10 3330 1589 29947549
Thyroiditis 30.28 20.41 10 3330 1619 29947519
Exomphalos 28.57 20.41 6 3334 164 29948974
Pericarditis fungal 28.10 20.41 6 3334 178 29948960
Tracheo-oesophageal fistula 27.92 20.41 7 3333 424 29948714
Respiratory tract haemorrhage 27.62 20.41 8 3332 839 29948299
Urine ketone body present 26.47 20.41 8 3332 971 29948167
Cholestatic liver injury 26.47 20.41 9 3331 1592 29947546
Glycosuria 24.17 20.41 8 3332 1303 29947835
Electrolyte imbalance 23.20 20.41 15 3325 11485 29937653
Autoimmune thyroiditis 21.96 20.41 7 3333 1013 29948125
Coagulation time shortened 21.82 20.41 5 3335 206 29948932

Pharmacologic Action:

SourceCodeDescription
ATC H03BB02 SYSTEMIC HORMONAL PREPARATIONS, EXCL. SEX HORMONES AND INSULINS
THYROID THERAPY
ANTITHYROID PREPARATIONS
Sulfur-containing imidazole derivatives
ATC H03BB52 SYSTEMIC HORMONAL PREPARATIONS, EXCL. SEX HORMONES AND INSULINS
THYROID THERAPY
ANTITHYROID PREPARATIONS
Sulfur-containing imidazole derivatives
MeSH PA D013956 Antithyroid Agents
MeSH PA D006727 Hormone Antagonists
FDA MoA N0000175917 Thyroid Hormone Synthesis Inhibitors
FDA EPC N0000175918 Thyroid Hormone Synthesis Inhibitor
CHEBI has role CHEBI:50671 antithyroid agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Hyperthyroidism indication 34486009 DOID:7998
Thyrotoxic crisis off-label use 29028009 DOID:12837
Agranulocytosis contraindication 17182001 DOID:12987
Hypothyroidism contraindication 40930008 DOID:1459
Factor II deficiency contraindication 73975000
Leukopenia contraindication 84828003 DOID:615
Pancytopenia contraindication 127034005 DOID:12450
Liver function tests abnormal contraindication 166603001
Drug-induced hepatitis contraindication 235876009
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Bone marrow depression contraindication 307762000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 10.7 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Thyroid peroxidase Enzyme INHIBITOR IC50 5.57 WOMBAT-PK CHEMBL
Lactoperoxidase Enzyme IC50 4.93 CHEMBL
Dopamine beta-hydroxylase Unclassified Ki 4.35 CHEMBL
Lactoperoxidase Enzyme IC50 5.08 CHEMBL

External reference:

IDSource
4017434 VUID
N0000145822 NUI
D00401 KEGG_DRUG
4017434 VANDF
C0025644 UMLSCUI
CHEBI:50673 CHEBI
MMZ PDB_CHEM_ID
CHEMBL1515 ChEMBL_ID
D008713 MESH_DESCRIPTOR_UI
DB00763 DRUGBANK_ID
6649 IUPHAR_LIGAND_ID
4198 INN_ID
554Z48XN5E UNII
1349907 PUBCHEM_CID
224936 RXNORM
2293 MMSL
31962 MMSL
5073 MMSL
d00290 MMSL
002139 NDDF
37656002 SNOMEDCT_US
404864000 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Methimazole HUMAN PRESCRIPTION DRUG LABEL 1 0185-0205 TABLET 5 mg ORAL ANDA 19 sections
Methimazole HUMAN PRESCRIPTION DRUG LABEL 1 0185-0210 TABLET 10 mg ORAL ANDA 19 sections
Methimazole HUMAN PRESCRIPTION DRUG LABEL 1 23155-070 TABLET 5 mg ORAL ANDA 19 sections
Methimazole HUMAN PRESCRIPTION DRUG LABEL 1 23155-071 TABLET 10 mg ORAL ANDA 19 sections
Methimazole HUMAN PRESCRIPTION DRUG LABEL 1 42254-008 TABLET 5 mg ORAL ANDA 18 sections
Methimazole HUMAN PRESCRIPTION DRUG LABEL 1 42254-009 TABLET 10 mg ORAL ANDA 18 sections
Methimazole HUMAN PRESCRIPTION DRUG LABEL 1 49884-640 TABLET 5 mg ORAL ANDA 19 sections
Methimazole HUMAN PRESCRIPTION DRUG LABEL 1 49884-641 TABLET 10 mg ORAL ANDA 19 sections
Methimazole HUMAN PRESCRIPTION DRUG LABEL 1 50090-2366 TABLET 5 mg ORAL ANDA 19 sections
Methimazole HUMAN PRESCRIPTION DRUG LABEL 1 50090-3334 TABLET 5 mg ORAL ANDA 20 sections
Methimazole HUMAN PRESCRIPTION DRUG LABEL 1 51293-820 TABLET 5 mg ORAL ANDA 18 sections
Methimazole HUMAN PRESCRIPTION DRUG LABEL 1 51293-821 TABLET 10 mg ORAL ANDA 18 sections
Methimazole HUMAN PRESCRIPTION DRUG LABEL 1 53808-0850 TABLET 10 mg ORAL ANDA 18 sections
Methimazole HUMAN PRESCRIPTION DRUG LABEL 1 53808-0949 TABLET 10 mg ORAL ANDA 18 sections
METHIMAZOLE HUMAN PRESCRIPTION DRUG LABEL 1 53808-1044 TABLET 10 mg ORAL ANDA 18 sections
Methimazole HUMAN PRESCRIPTION DRUG LABEL 1 54868-5135 TABLET 10 mg ORAL ANDA 18 sections
Methimazole HUMAN PRESCRIPTION DRUG LABEL 1 54868-6071 TABLET 5 mg ORAL ANDA 18 sections
Methimazole HUMAN PRESCRIPTION DRUG LABEL 1 60429-380 TABLET 5 mg ORAL ANDA 19 sections
Methimazole HUMAN PRESCRIPTION DRUG LABEL 1 60429-381 TABLET 10 mg ORAL ANDA 19 sections
Methimazole HUMAN PRESCRIPTION DRUG LABEL 1 60687-357 TABLET 5 mg ORAL ANDA 19 sections
Methimazole HUMAN PRESCRIPTION DRUG LABEL 1 60687-370 TABLET 10 mg ORAL ANDA 19 sections
TAPAZOLE HUMAN PRESCRIPTION DRUG LABEL 1 60793-104 TABLET 5 mg ORAL ANDA 21 sections
TAPAZOLE HUMAN PRESCRIPTION DRUG LABEL 1 60793-105 TABLET 10 mg ORAL ANDA 21 sections
Methimazole HUMAN PRESCRIPTION DRUG LABEL 1 63629-2026 TABLET 5 mg ORAL ANDA 18 sections
Methimazole HUMAN PRESCRIPTION DRUG LABEL 1 63629-2027 TABLET 10 mg ORAL ANDA 18 sections
Methimazole HUMAN PRESCRIPTION DRUG LABEL 1 63629-2224 TABLET 10 mg ORAL ANDA 19 sections
Methimazole HUMAN PRESCRIPTION DRUG LABEL 1 63629-2225 TABLET 5 mg ORAL ANDA 19 sections
Methimazole HUMAN PRESCRIPTION DRUG LABEL 1 63629-6408 TABLET 10 mg ORAL ANDA 19 sections
Methimazole HUMAN PRESCRIPTION DRUG LABEL 1 63629-8347 TABLET 5 mg ORAL ANDA 19 sections
Methimazole HUMAN PRESCRIPTION DRUG LABEL 1 64980-260 TABLET 5 mg ORAL ANDA 19 sections