ethionamide 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 ┬ÁM/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 201.66 56.12 32 125 2592 2355336
Vomiting 92.27 56.12 31 126 71571 2286357
Anaemia 90.93 56.12 26 131 34766 2323162
Tuberculosis 73.31 56.12 13 144 1922 2356006
Electrocardiogram QT prolonged 60.54 56.12 14 143 7800 2350128
Neuropathy peripheral 60.27 56.12 15 142 11417 2346511

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
Tuberculosis 95.56 48.44 18 173 1848 1744742
Drug resistance 91.54 48.44 19 172 3211 1743379
Anaemia 76.87 48.44 26 165 29431 1717159
Vomiting 73.94 48.44 27 164 38288 1708302
Neuropathy peripheral 62.14 48.44 17 174 9236 1737354
Electrocardiogram QT prolonged 60.50 48.44 15 176 5530 1741060
Hypothyroidism 54.87 48.44 12 179 2548 1744042

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 agent
CHEBI has role CHEBI:35679 antilipemic drug
CHEBI has role CHEBI:35816 leprostatic drug
CHEBI has role CHEBI:50266 prodrug
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 (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

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

External reference:

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

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Trecator HUMAN PRESCRIPTION DRUG LABEL 1 0008-4117 TABLET, FILM COATED 250 mg ORAL NDA 13 sections