ethionamide ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
1083 536-33-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • ethioniamide
  • amidazine
  • ethionamide
A second-line antitubercular agent that inhibits mycolic acid synthesis.
  • Molecular weight: 166.24
  • Formula: C8H10N2S
  • CLOGP: 1.73
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 1
  • TPSA: 38.91
  • ALOGS: -2.30
  • ROTB: 2

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
0.75 g O

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 100.45 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 80 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
April 30, 1965 FDA WYETH PHARMS INC

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
Drug resistance 205.57 43.86 50 783 18939 50585352
Drug reaction with eosinophilia and systemic symptoms 75.29 43.86 25 808 28399 50575892
Electrocardiogram QT prolonged 44.15 43.86 20 813 51866 50552425

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
Drug resistance 120.22 38.17 39 899 21501 29552088
Electrocardiogram QT prolonged 56.64 38.17 26 912 36111 29537478
Tuberculoma of central nervous system 40.57 38.17 7 931 241 29573348

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
Drug resistance 284.88 37.88 83 1793 35019 64461837
Electrocardiogram QT prolonged 88.43 37.88 44 1832 79404 64417452
Drug reaction with eosinophilia and systemic symptoms 84.85 37.88 38 1838 54179 64442677
Neuropathy peripheral 69.72 37.88 43 1833 117482 64379374
Tuberculoma of central nervous system 67.41 37.88 12 1864 542 64496314
Anaemia 56.85 37.88 62 1814 378618 64118238
Vomiting 48.51 37.88 69 1807 551048 63945808
Hypothyroidism 46.68 37.88 23 1853 40434 64456422
Drug-induced liver injury 43.12 37.88 23 1853 47620 64449236

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC J04AD03 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIMYCOBACTERIALS
DRUGS FOR TREATMENT OF TUBERCULOSIS
Thiocarbamide derivatives
FDA EPC N0000175483 Antimycobacterial
CHEBI has role CHEBI:33231 antitubercular agents
CHEBI has role CHEBI:35679 antilipemic drugs
CHEBI has role CHEBI:35816 leprostatic drugs
CHEBI has role CHEBI:50185 fatty acid synthesis inhibitors
CHEBI has role CHEBI:50266 Prodrugs
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000963 Antimetabolites
MeSH PA D000995 Antitubercular Agents
MeSH PA D054872 Fatty Acid Synthesis Inhibitors
MeSH PA D000960 Hypolipidemic Agents

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Acute tuberculosis indication 25629007
Pulmonary tuberculosis indication 154283005 DOID:2957
Pulmonary Mycobacterium avium complex infection indication 186342000
Tuberculosis of meninges off-label use 58437007
Leprosy off-label use 81004002 DOID:1024
Atypical mycobacterial infection off-label use 111812000
Alcoholism contraindication 7200002
Hypothyroidism contraindication 40930008 DOID:1459
Hepatic failure contraindication 59927004
Diabetes mellitus contraindication 73211009 DOID:9351
Disease of liver contraindication 235856003 DOID:409




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 11.43 acidic
pKa2 5.85 Basic

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
Enoyl-[acyl-carrier-protein] reductase [NADH] Enzyme INHIBITOR DRUGBANK CHEMBL
Catalase-peroxidase Enzyme WOMBAT-PK
Polyphenol oxidase 2 Enzyme IC50 5.40 CHEMBL

External reference:

IDSource
4018059 VUID
N0000146400 NUI
D00591 KEGG_DRUG
4018059 VANDF
C0015021 UMLSCUI
CHEBI:4885 CHEBI
CHEMBL1441 ChEMBL_ID
DB00609 DRUGBANK_ID
D005000 MESH_DESCRIPTOR_UI
2761171 PUBCHEM_CID
867 INN_ID
OAY8ORS3CQ UNII
4127 RXNORM
4700 MMSL
d01100 MMSL
002851 NDDF
32800009 SNOMEDCT_US
414148003 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Trecator HUMAN PRESCRIPTION DRUG LABEL 1 0008-4117 TABLET, FILM COATED 250 mg ORAL NDA 25 sections