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
S (Water solubility) 0.84 mg/mL Bocci G, Oprea TI, Benet LZ
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Bocci G, Oprea TI, Benet LZ

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 205.42 45.40 50 817 22883 63465272
Drug reaction with eosinophilia and systemic symptoms 75.59 45.40 25 842 33811 63454344
Electrocardiogram QT prolonged 51.63 45.40 22 845 59508 63428647

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 165.15 41.43 53 1158 25874 34929846
Electrocardiogram QT prolonged 72.68 41.43 33 1178 40919 34914801
Neuropathy peripheral 50.69 41.43 33 1178 83230 34872490
Urinary tract inflammation 42.35 41.43 7 1204 169 34955551
Neuropsychiatric symptoms 42.03 41.43 9 1202 893 34954827

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 328.24 35.79 95 2062 42118 79700113
Electrocardiogram QT prolonged 113.09 35.79 53 2104 90333 79651898
Neuropathy peripheral 85.48 35.79 51 2106 141254 79600977
Drug reaction with eosinophilia and systemic symptoms 81.28 35.79 38 2119 64206 79678025
Tuberculoma of central nervous system 67.58 35.79 12 2145 575 79741656
Anaemia 62.52 35.79 68 2089 444947 79297284
Pathogen resistance 51.53 35.79 18 2139 14324 79727907
Vomiting 45.07 35.79 71 2086 665757 79076474
Hypothyroidism 42.62 35.79 23 2134 52369 79689862
Toxic optic neuropathy 42.04 35.79 9 2148 1144 79741087
Conductive deafness 41.76 35.79 7 2150 238 79741993
Multiple-drug resistance 39.27 35.79 13 2144 8795 79733436
Drug-induced liver injury 37.64 35.79 23 2134 66094 79676137

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
1JA PDB_CHEM_ID
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