Ethionamide (CED0004307)

Record Information
Version1.0
Creation Date2016-05-22 03:26:50 UTC
Update Date2026-08-24 11:29:18 UTC
Accession NumberCHEM016305
Identification
Common NameEthionamide
ClassSmall Molecule
Description
Ethionamide belongs to the pyridines and derivatives, a class of organoheterocyclic compounds within the organic compounds. This compound has the chemical formula C8H10N2S and an average molecular weight of 166.24 g/mol. Ethionamide is found in or released from ten recorded sources. Within healthcare, pharmaceuticals, and veterinary products, it is utilized as a drug for the treatment of tuberculosis. Other recorded sources include indoor air via air, dust, and atmospheric transport; the preparation of malt within food, food processing, and cookware; household cleaning and consumer products such as pipe accessories, ash trays, and other smoking requisites; and electrical and electronic equipment, specifically communication cables or conductors, power cables, antennas, and video games. Exposure to the compound occurs through oral and inhalation routes. At the molecular level, ethionamide interacts with three recorded protein targets. It acts as an inhibitor or otherwise affects catalase-peroxidase (katG), enoyl-[acyl-carrier-protein] reductase [NADH] (inhA), and nuclear factor erythroid 2-related factor 2 (NFE2L2).
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
2-Ethyl-4-thiopyridylamideChEBI
ETHChEBI
EthinamideChEBI
EthionamidumChEBI
EthioniamideChEBI
EthylisothiamideChEBI
EthyonomideChEBI
EtionamidChEBI
EtionamidaChEBI
EtionamideChEBI
EtioniamidChEBI
ETPChEBI
TrecatorChEBI
ABBR etoKegg
Trecator-SCHMDB
Ethionamid prothionamidHMDB
Wyeth brand OF ethionamideHMDB
AmidazineHMDB
Trecator SCHMDB
Chemical FormulaC8H10N2S
Average Molecular Mass166.243 g/mol
Monoisotopic Mass166.056 g/mol
CAS Registry Number536-33-4
IUPAC Name2-ethylpyridine-4-carbothioamide
Traditional Nameethionamide
SMILESCCC1=NC=CC(=C1)C(N)=S
InChI IdentifierInChI=1S/C8H10N2S/c1-2-7-5-6(8(9)11)3-4-10-7/h3-5H,2H2,1H3,(H2,9,11)
InChI KeyAEOCXXJPGCBFJA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyridines and derivatives. Pyridines and derivatives are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassNot Available
Direct ParentPyridines and derivatives
Alternative Parents
Substituents
  • Pyridine
  • Heteroaromatic compound
  • Thioamide
  • Azacycle
  • Thiocarboxylic acid amide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Thiocarbonyl group
  • Organosulfur compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.84 g/LALOGPS
logP1.88ALOGPS
logP1.33ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)11.89ChemAxon
pKa (Strongest Basic)5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.91 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity50.19 m³·mol⁻¹ChemAxon
Polarizability17.99 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0pw9-3900000000-263ea10a0631f3806479Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-66bf96cc96715b3d5326Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-1900000000-afd158837fc707e8fb01Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9200000000-dcd5e9f885fdaa4b6be0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9000000000-10fa8785304c67e3f37cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9000000000-78e21f4e886c1dbc2f13Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-4f9e673cda59e1bc62eeNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-1900000000-8adf72703aaa8ef481a2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-1900000000-44e982c330b6d64a6be4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-055f-0900000000-84eddf78775359274c7dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00kf-0900000000-7cc8eb00a5c2549dc2f5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000x-0900000000-fc1226426db462b86e63Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-5b5b860c07ddf55cacb7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014l-0900000000-fb94236c6babbb910b90Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-adc07c3f2262dea21f0cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9000000000-7ec1b7cee36ce6378c2dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9000000000-32379f7dd10be4ffea50Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000x-0900000000-8d392e3fe50cec3a35fdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9100000000-b518e636d5c5a3b8c8d6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0aor-9600000000-a824886082888c479700Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-363b8746b33c560312eeNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-c06a7f8c70c19736b28cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ue9-2900000000-65ccd0d496f10810f52fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00lr-0900000000-8a32dd98293192dd197bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0api-2900000000-e349b9c8e22e145fe305Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a59-9400000000-c3ca9dd395c1e4d8a6a6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0uxr-0900000000-45a6d64e9fc3198e228bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0uxr-0900000000-2419af7691c17aa48027Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9600000000-453c8342dcae457962d7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0900000000-5386f4adb155cb78a6c7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0aor-9700000000-34c19d0732929168dc1cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9000000000-286b63d3516de7d14a12Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
255.0Log mg/kg[140:450]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
19Indoor airAir, dust & atmospheric transportNot Available
349Drugs for treatment of tuberculosisHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
510Communication Cables Or ConductorsElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
554Ash TraysHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
598Fertiliser DistributorsAgriculture & land managementNot Available
633Azo DyesTextiles, leather & furnishingsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Lysine-specific demethylase 5C structureClick to view 3D structureLysine-specific demethylase 5CP41229HumansPredicted (SEA)5.44945
Lysine-specific demethylase 4C structureClick to view 3D structureLysine-specific demethylase 4CQ9H3R0HumansPredicted (SEA)14.48
Lysine-specific demethylase 5B structureClick to view 3D structureLysine-specific demethylase 5BQ9UGL1HumansPredicted (SEA)9.57545
Lysine-specific demethylase 5A structureClick to view 3D structureLysine-specific demethylase 5AP29375HumansPredicted (SEA)10.5096
Lysine-specific demethylase 6A structureClick to view 3D structureLysine-specific demethylase 6AO15550HumansPredicted (SEA)1.16774
Lysine-specific demethylase 2B structureClick to view 3D structureLysine-specific demethylase 2BQ8NHM5HumansPredicted (SEA)5.3716
Lysine-specific demethylase 6B structureClick to view 3D structureLysine-specific demethylase 6BO15054HumansPredicted (SEA)11.1324
Lysine-specific demethylase 4A structureClick to view 3D structureLysine-specific demethylase 4AO75164HumansPredicted (SEA)19.4623
Click to view 3D structureLysine-specific demethylase 3AQ9Y4C1HumansPredicted (SEA)17.5161
Lysine-specific demethylase 2A structureClick to view 3D structureLysine-specific demethylase 2AQ9Y2K7HumansPredicted (SEA)31.9182
Lysine-specific demethylase 4E structureClick to view 3D structureLysine-specific demethylase 4EB2RXH2HumansPredicted (SEA)94.2754
Lysine-specific demethylase 4B structureClick to view 3D structureLysine-specific demethylase 4BO94953HumansPredicted (SEA)16.9711
Click to view 3D structureBeta-lactamaseQ44079Aeromonas hydrophilaPredicted (SEA)35.6549
Lysine-specific demethylase 5D structureClick to view 3D structureLysine-specific demethylase 5DQ9BY66HumansPredicted (SEA)1.16774
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)4979.63
Click to view 3D structurePhospholipase A2 group VP51433Rattus norvegicusPredicted (SEA)204.821
Ribonucleoside-diphosphate reductase subunit M2 structureClick to view 3D structureRibonucleoside-diphosphate reductase subunit M2P31350HumansPredicted (SEA)2.56902
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)6382.08
3-phosphoinositide-dependent protein kinase 1 structureClick to view 3D structure3-phosphoinositide-dependent protein kinase 1O15530HumansPredicted (SEA)4695.09
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)6823.56
Mitogen-activated protein kinase 8 structureClick to view 3D structureMitogen-activated protein kinase 8P45983HumansPredicted (SEA)5362.02
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)6677.44
Click to view 3D structureAcrosinP08001Sus scrofaPredicted (SEA)52.7818
Urokinase-type plasminogen activator structureClick to view 3D structureUrokinase-type plasminogen activatorP00749HumansPredicted (SEA)1608.99
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform structureClick to view 3D structurePhosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoformP42336HumansPredicted (SEA)4142.12
Concentrations
Not Available
External Links
DrugBank IDDB00609
HMDB IDHMDB0014747
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEthionamide
Chemspider ID2041901
ChEBI ID4885
PubChem Compound ID2761171
Kegg Compound IDC07665
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=14651620
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15673755
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15850780