thiamazole ๐Ÿถ Veterinary Use | 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 ยตM/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 324.90 14.11 124 8000 21297 50575703
Thyrotoxic crisis 221.69 14.11 45 8079 707 50596293
Hyperthyroidism 200.83 14.11 75 8049 12100 50584900
Antithyroid arthritis syndrome 66.33 14.11 9 8115 4 50596996
Hypothyroidism 66.16 14.11 50 8074 34075 50562925
Choanal atresia 59.11 14.11 9 8115 20 50596980
Exophthalmos 45.64 14.11 14 8110 1236 50595764
Blood thyroid stimulating hormone decreased 35.46 14.11 16 8108 4156 50592844
Drug-induced liver injury 35.26 14.11 32 8092 28063 50568937
Neutropenia 34.00 14.11 74 8050 147891 50449109
Dysmorphism 30.85 14.11 12 8112 2155 50594845
Anti-neutrophil cytoplasmic antibody positive vasculitis 30.04 14.11 12 8112 2310 50594690
Goitre 28.85 14.11 15 8109 5305 50591695
Pulmonary alveolar haemorrhage 26.67 14.11 13 8111 4014 50592986
Cardiac arrest 26.64 14.11 48 8076 83603 50513397
Mucocutaneous candidiasis 26.56 14.11 4 8120 8 50596992
Endocrine ophthalmopathy 26.39 14.11 7 8117 366 50596634
Polyarthritis 25.79 14.11 16 8108 7911 50589089
Oropharyngeal pain 25.23 14.11 45 8079 77756 50519244
Aplasia cutis congenita 25.23 14.11 5 8119 69 50596931
Neuroglycopenia 25.23 14.11 5 8119 69 50596931
Thyroxine free increased 25.18 14.11 8 8116 793 50596207
Drug intolerance 24.85 14.11 3 8121 219101 50377899
Toxic nodular goitre 24.51 14.11 4 8120 16 50596984
Drug interaction 22.67 14.11 77 8047 199544 50397456
Eosinophilic pleural effusion 20.85 14.11 4 8120 46 50596954
Thyroid haemorrhage 20.19 14.11 4 8120 55 50596945
Acquired epidermolysis bullosa 20.13 14.11 4 8120 56 50596944
Toxic goitre 19.92 14.11 3 8121 6 50596994
Sopor 19.92 14.11 20 8104 19859 50577141
Thyroidectomy 19.70 14.11 7 8117 977 50596023
Electrocardiogram QT prolonged 19.43 14.11 32 8092 51854 50545146
Autoimmune neutropenia 19.29 14.11 4 8120 70 50596930
Functional residual capacity increased 19.13 14.11 4 8120 73 50596927
Insulin autoimmune syndrome 19.08 14.11 4 8120 74 50596926
Thyroid disorder 19.04 14.11 16 8108 12661 50584339
Hypoglycaemia 18.68 14.11 32 8092 53549 50543451
Stevens-Johnson syndrome 18.41 14.11 20 8104 21732 50575268
Respiratory syncytial virus infection 18.40 14.11 11 8113 5091 50591909
Jaundice cholestatic 18.38 14.11 11 8113 5100 50591900
Symptom masked 18.25 14.11 6 8118 663 50596337
Hypersensitivity vasculitis 18.07 14.11 10 8114 4005 50592995
Clinodactyly 18.05 14.11 4 8120 97 50596903
Thyroxine free abnormal 16.86 14.11 3 8121 22 50596978
Rheumatoid arthritis 16.42 14.11 6 8118 202544 50394456
Cardiac failure 16.27 14.11 37 8087 76003 50520997
Metabolic function test abnormal 16.05 14.11 4 8120 163 50596837
Microscopic polyangiitis 16.00 14.11 4 8120 165 50596835
Atrial fibrillation 15.98 14.11 44 8080 101701 50495299
Arthropathy 15.98 14.11 3 8121 157903 50439097
Spigelian hernia 15.60 14.11 3 8121 35 50596965
Kidney transplant rejection 15.44 14.11 9 8115 3978 50593022
Febrile neutropenia 15.11 14.11 42 8082 97625 50499375
Acute generalised exanthematous pustulosis 14.93 14.11 12 8112 8926 50588074
Mucosal erosion 14.42 14.11 6 8118 1281 50595719
Hepatitis cholestatic 14.19 14.11 10 8114 6107 50590893

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 160.00 19.42 54 3568 8554 29562351
Agranulocytosis 76.53 19.42 41 3581 20299 29550606
Thyrotoxic periodic paralysis 66.56 19.42 11 3611 67 29570838
Hypothyroidism 54.09 19.42 30 3592 15876 29555029
Thyrotoxic crisis 49.81 19.42 11 3611 348 29570557
Kounis syndrome 48.32 19.42 15 3607 1814 29569091
Polymerase chain reaction 43.64 19.42 8 3614 95 29570810
Exomphalos 33.96 19.42 7 3615 158 29570747
Albumin urine present 33.38 19.42 8 3614 365 29570540
Cholestatic liver injury 32.88 19.42 11 3611 1686 29569219
Urine leukocyte esterase positive 32.72 19.42 8 3614 397 29570508
Goitre 30.39 19.42 10 3612 1457 29569448
Haemoglobinuria 29.75 19.42 8 3614 581 29570324
Mouth swelling 29.68 19.42 10 3612 1566 29569339
Pericarditis fungal 28.37 19.42 6 3616 154 29570751
Respiratory tract haemorrhage 25.86 19.42 8 3614 956 29569949
Autoimmune thyroiditis 25.29 19.42 8 3614 1028 29569877
Urine ketone body present 25.20 19.42 8 3614 1040 29569865
Axial spondyloarthritis 25.13 19.42 6 3616 269 29570636
Glycosuria 24.38 19.42 8 3614 1154 29569751
Loss of proprioception 23.30 19.42 6 3616 368 29570537
Tracheo-oesophageal fistula 22.47 19.42 6 3616 424 29570481
Blood cyanide increased 22.10 19.42 4 3618 44 29570861
Coagulation time shortened 21.17 19.42 5 3617 214 29570691
Blood sodium decreased 20.72 19.42 16 3606 14751 29556154
Electrolyte imbalance 19.83 19.42 14 3608 11260 29559645
Urinary bladder rupture 19.59 19.42 4 3618 86 29570819

FDA Adverse Event Reporting System (Geriatric)

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 357.87 13.38 158 10513 38071 64449990
Hyperthyroidism 282.27 13.38 108 10563 18071 64469990
Thyrotoxic crisis 252.95 13.38 54 10617 1062 64486999
Hypothyroidism 103.56 13.38 71 10600 40386 64447675
Antithyroid arthritis syndrome 66.06 13.38 9 10662 4 64488057
Thyrotoxic periodic paralysis 60.41 13.38 11 10660 90 64487971
Exophthalmos 50.30 13.38 16 10655 1544 64486517
Drug-induced liver injury 46.67 13.38 48 10623 47595 64440466
Goitre 44.66 13.38 20 10651 4953 64483108
Anti-neutrophil cytoplasmic antibody positive vasculitis 43.94 13.38 17 10654 2919 64485142
Polymerase chain reaction 39.31 13.38 8 10663 123 64487938
Kounis syndrome 36.51 13.38 15 10656 3010 64485051
Endocrine ophthalmopathy 30.06 13.38 8 10663 411 64487650
Polyarthritis 27.11 13.38 18 10653 9697 64478364
Albumin urine present 26.45 13.38 8 10663 653 64487408
Pericarditis fungal 25.97 13.38 6 10665 171 64487890
Blood thyroid stimulating hormone decreased 25.85 13.38 14 10657 5216 64482845
Haemoglobinuria 25.64 13.38 8 10663 725 64487336
Cardiac failure 25.55 13.38 63 10608 132310 64355751
Autoimmune thyroiditis 24.87 13.38 12 10659 3516 64484545
Neuroglycopenia 24.69 13.38 5 10666 75 64487986
Neutropenia 24.38 13.38 91 10580 239533 64248528
Toxic goitre 24.20 13.38 4 10667 17 64488044
Jaundice cholestatic 24.03 13.38 16 10655 8654 64479407
Cardiac arrest 23.32 13.38 67 10604 153997 64334064
Thyroxine free increased 22.40 13.38 8 10663 1099 64486962
Drug interaction 22.06 13.38 118 10553 361965 64126096
Cholestatic liver injury 21.45 13.38 11 10660 3668 64484393
Mucocutaneous candidiasis 21.24 13.38 4 10667 40 64488021
Electrocardiogram QT prolonged 21.15 13.38 43 10628 79405 64408656
Drug intolerance 21.12 13.38 3 10668 187989 64300072
Blood cyanide increased 20.90 13.38 4 10667 44 64488017
Atrial fibrillation 20.87 13.38 69 10602 171020 64317041
Respiratory tract haemorrhage 20.12 13.38 8 10663 1476 64486585
Urine leukocyte esterase positive 19.34 13.38 10 10661 3393 64484668
Hepatitis cholestatic 19.20 13.38 16 10655 12139 64475922
Sopor 19.02 13.38 24 10647 29637 64458424
Oropharyngeal pain 18.97 13.38 44 10627 88823 64399238
Functional residual capacity increased 18.81 13.38 4 10667 77 64487984
Thyroid haemorrhage 18.71 13.38 4 10667 79 64487982
Completed suicide 18.49 13.38 7 10664 224407 64263654
Acquired epidermolysis bullosa 18.39 13.38 4 10667 86 64487975
Urinary bladder rupture 18.05 13.38 4 10667 94 64487967
Pulmonary alveolar haemorrhage 17.89 13.38 14 10657 9724 64478337
Glycosuria 17.54 13.38 8 10663 2066 64485995
Thyroidectomy 16.92 13.38 6 10665 807 64487254
Coagulation time shortened 16.87 13.38 5 10666 381 64487680
Jaundice 16.30 13.38 29 10642 48483 64439578
Thyroid dermatopathy 16.22 13.38 3 10668 27 64488034
Immune-mediated hepatitis 16.15 13.38 8 10663 2481 64485580
Ventricular septal defect 15.91 13.38 5 10666 464 64487597
Mouth swelling 15.56 13.38 10 10661 5097 64482964
Metabolic function test abnormal 15.52 13.38 4 10667 181 64487880
Tri-iodothyronine increased 15.44 13.38 4 10667 185 64487876
Antineutrophil cytoplasmic antibody 15.43 13.38 3 10668 36 64488025
Hypersensitivity vasculitis 15.27 13.38 11 10660 6750 64481311
Toxic nodular goitre 15.21 13.38 3 10668 39 64488022
Bradycardia 14.69 13.38 48 10623 118171 64369890
Symptom masked 14.63 13.38 6 10665 1198 64486863
Respiratory syncytial virus infection 14.56 13.38 11 10660 7257 64480804
Tonsillitis 14.37 13.38 10 10661 5810 64482251
Cholestasis 14.03 13.38 26 10645 44846 64443215
Urine ketone body present 14.01 13.38 8 10663 3299 64484762
Eosinophilic pleural effusion 13.98 13.38 4 10667 269 64487792
Pure white cell aplasia 13.77 13.38 3 10668 65 64487996
Hepatitis 13.74 13.38 26 10645 45556 64442505
Hypoglycaemia 13.50 13.38 39 10632 89853 64398208
Oedema mucosal 13.44 13.38 6 10665 1473 64486588

FDA Adverse Event Reporting System (Pediatric)

None

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 drugs

Drug Use | Suggest Off label Use Form| |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




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

ProductApplicantIngredients
Felimazole Dechra, Ltd. 1

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
Lactoperoxidase Enzyme IC50 5.08 CHEMBL
Dopamine beta-hydroxylase Enzyme Ki 4.35 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
DB00763 DRUGBANK_ID
6649 IUPHAR_LIGAND_ID
554Z48XN5E UNII
1349907 PUBCHEM_CID
224936 RXNORM
2293 MMSL
31962 MMSL
5073 MMSL
d00290 MMSL
002139 NDDF
37656002 SNOMEDCT_US
404864000 SNOMEDCT_US
D008713 MESH_DESCRIPTOR_UI
4198 INN_ID

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 23155-070 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 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 49884-640 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 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
Methimazole HUMAN PRESCRIPTION DRUG LABEL 1 62135-205 TABLET 5 mg ORAL ANDA 12 sections
Methimazole HUMAN PRESCRIPTION DRUG LABEL 1 62135-206 TABLET 10 mg ORAL ANDA 12 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