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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2018-05-20 20:10:12 UTC
HMDB IDHMDB0014747
Secondary Accession Numbers
  • HMDB14747
Metabolite Identification
Common NameEthionamide
DescriptionEthionamide is only found in individuals that have used or taken this drug. It is a second-line antitubercular agent that inhibits mycolic acid synthesis. It also may be used for treatment of leprosy. (From Smith and Reynard, Textbook of Pharmacology, 1992, p868)Ethionamide may be bacteriostatic or bactericidal in action, depending on the concentration of the drug attained at the site of infection and the susceptibility of the infecting organism. Ethionamide, like prothionamide and pyrazinamide, is a nicotinic acid derivative related to isoniazid. It is thought that ethionamide undergoes intracellular modification and acts in a similar fashion to isoniazid. Isoniazid inhibits the synthesis of mycoloic acids, an essential component of the bacterial cell wall. Specifically isoniazid inhibits InhA, the enoyl reductase from Mycobacterium tuberculosis, by forming a covalent adduct with the NAD cofactor. It is the INH-NAD adduct that acts as a slow, tight-binding competitive inhibitor of InhA.
Structure
Thumb
Synonyms
ValueSource
2-Ethyl-4-thiopyridylamideChEBI
ETHChEBI
EthinamideChEBI
EthionamidumChEBI
EthioniamideChEBI
EthylisothiamideChEBI
EthyonomideChEBI
EtionamidChEBI
EtionamidaChEBI
EtionamideChEBI
EtioniamidChEBI
ETPChEBI
TrecatorChEBI
Ethionamid prothionamidHMDB
Wyeth brand OF ethionamideMeSH
AmidazineMeSH
Trecator SCMeSH
Trecator-SCMeSH
Chemical FormulaC8H10N2S
Average Molecular Weight166.243
Monoisotopic Molecular Weight166.05646902
IUPAC Name2-ethylpyridine-4-carbothioamide
Traditional Nameethionamide
CAS Registry Number536-33-4
SMILES
CCC1=NC=CC(=C1)C(N)=S
InChI Identifier
InChI=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
DescriptionThis compound belongs to the class of organic compounds known as pyridines and derivatives. These 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
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point163 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.84 g/LNot Available
LogP0.5Not 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pw9-3900000000-263ea10a0631f3806479View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-66bf96cc96715b3d5326View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-1900000000-afd158837fc707e8fb01View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9200000000-dcd5e9f885fdaa4b6be0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-10fa8785304c67e3f37cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-78e21f4e886c1dbc2f13View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-0900000000-4f9e673cda59e1bc62eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-363b8746b33c560312eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-c06a7f8c70c19736b28cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-2900000000-65ccd0d496f10810f52fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00lr-0900000000-8a32dd98293192dd197bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0api-2900000000-e349b9c8e22e145fe305View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-9400000000-c3ca9dd395c1e4d8a6a6View in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00609 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00609 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00609
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2041901
KEGG Compound IDC07665
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEthionamide
METLIN IDNot Available
PubChem Compound2761171
PDB IDNot Available
ChEBI ID4885
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available