ethionamide   Click here for help

GtoPdb Ligand ID: 12954

Synonyms: 1314 TH | Bayer 5312 | Trecator®
Approved drug PDB Ligand
ethionamide is an approved drug (FDA (1965))
Compound class: Synthetic organic
Comment: Ethionamide is a thioamide compound with potent antibacterial activity against mycobacteria. It is a prodrug that requires intracellular activation, by the monooxygenase EthA, in Mycobacterium tuberculosis [1]. Ethionamide is used in the treatment of multidrug-resistant tuberculosis (MDR-TB) and extensively drug-resistant tuberculosis (XDR-TB).

ethionamide is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 70.47
Molecular weight 166.24
XLogP -0.23
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CCC1=CC(=CC=N1)C(=S)N
Isomeric SMILES CCC1=NC=CC(=C1)C(=S)N
InChI InChI=1S/C8H10N2S/c1-2-7-5-6(8(9)11)3-4-10-7/h3-5H,2H2,1H3,(H2,9,11)
InChI Key AEOCXXJPGCBFJA-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. FDA (1965)
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
2-ethylpyridine-4-carbothioamide
International Nonproprietary Names Click here for help
INN number INN
867 ethionamide
Synonyms Click here for help
1314 TH | Bayer 5312 | Trecator®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Ethionamide
Other databases
BindingDB Ligand 50239976
CAS Registry No. 536-33-4 (source: Scifinder)
ChEBI CHEBI:4885
ChEMBL Ligand CHEMBL1441
DrugBank Ligand DB00609
DrugCentral Ligand 1083
GtoPdb PubChem SID 485206075
PubChem CID 2761171
RCSB PDB Ligand 1JA
Search Google for chemical match using the InChIKey AEOCXXJPGCBFJA-UHFFFAOYSA-N
Search Google for chemicals with the same backbone AEOCXXJPGCBFJA
Search PubMed clinical trials ethionamide
Search PubMed titles ethionamide
Search PubMed titles/abstracts ethionamide
UniChem Compound Search for chemical match using the InChIKey AEOCXXJPGCBFJA-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey AEOCXXJPGCBFJA-UHFFFAOYSA-N
Wikipedia Ethionamide

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MedChemExpress
Ethionamide (links to external site)
Cat. No. HY-B0276