Chemical substance record

Ethionamide

536-33-4C₈H₁₀N₂S166.249 g/mol

Organic/Inorganic Small MoleculeChEBI source record

A thiocarboxamide that is pyridine-4-carbothioamide substituted by an ethyl group at position 2. A prodrug that undergoes metabolic activation by conversion to the corresponding S-oxide. — ChEBI

Safety references

Safety documents & references

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Identity & molecular properties

Source-linked values

CAS number	536-33-4	ChEBI ↗
Molecular formula	C₈H₁₀N₂S	ChEBI ↗
Molar mass	166.249 g/mol	ChEBI ↗
Monoisotopic mass	166.05647 Da	ChEBI ↗
Formal charge	0	ChEBI ↗
ChEBI identifier	CHEBI:4885	ChEBI ↗

Cross-source molecular data

PubChem

Molar mass	166.25 g/mol	PubChem ↗
Exact mass	166.05646950 Da	PubChem ↗
Computed XLogP	1.1	PubChem ↗
Topological polar surface area (Å²)	71	PubChem ↗
H-bond donors	1	PubChem ↗
H-bond acceptors	2	PubChem ↗
Rotatable bonds	2	PubChem ↗

PubChem computed values are shown separately from the ChEBI record. An exact InChIKey match was used to connect the records. Molecular descriptors do not describe a supplied product’s purity, particle size or performance.

Names & structural identifiers

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Source preferred name

ethionamide

IUPAC name

2-ethylpyridine-4-carbothioamide

InChIKey

AEOCXXJPGCBFJA-UHFFFAOYSA-N

SMILES

CCc1cc(C(N)=S)ccn1

InChI

InChI=1S/C8H10N2S/c1-2-7-5-6(8(9)11)3-4-10-7/h3-5H,2H2,1H3,(H2,9,11)

Names & synonyms

2-ethylpyridine-4-carbothioamideethionamidumetionamidaTrecator

Names are supplied by ChEBI. Trade names and related synonyms may describe a broader product context.

Classification & relationships

ChEBI ontology

pyridinesChEBI parent class · 26421 ↗thiocarboxamideChEBI parent class · 47956 ↗

organic heterocyclic compound organic molecular entity

Roles recorded in ChEBI

antitubercular agentantilipemic drugleprostatic drugfatty acid synthesis inhibitorprodrug

Database role annotations describe reported biological or chemical roles; they are not product approvals or recommendations for use.

Mass ↔ amount of substance

Calculated from sourced mass

Amount

Input unit

Equivalent amount

0.00601507 mol

Uses 166.249 g/mol from ChEBI. Assumes the substance described by this record; no purity or concentration correction is applied.

Elemental composition

Theoretical mass fractions

C

Carbon · 8 atoms

57.80%

S

Sulfur · 1 atom

19.29%

N

Nitrogen · 2 atoms

16.85%

H

Hydrogen · 10 atoms

6.06%

Calculated theoretical mass fractions from the reported formula and PubChem periodic-table atomic masses. These are not assay or purity results.

Research & patent references

Selected source associations

EthR, a repressor of the TetR/CamR family implicated in ethionamide resistance in mycobacteria, octamerizes cooperatively on its operator. ↗Molecular microbiology · 2004 Jan · PMID 14651620

Altered NADH/NAD+ ratio mediates coresistance to isoniazid and ethionamide in mycobacteria. ↗Antimicrobial agents and chemotherapy · 2005 Feb · PMID 15673755

GB800250 · Patent reference ↗Patent cross-reference supplied by ChEBI. Association alone does not establish claim scope.

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Sources & record history

Checked 27 Sep 2026

Identity, formula, mass, synonyms & ontologyEMBL-EBI ChEBI · CHEBI:4885

Release 255, 9 September 2026. ChEBI three-star (manually annotated) source entry. View original record ↗ · CC BY 4.0

Additional molecular descriptorsNCBI PubChem · CID 2761171 · retrieved 2026-09-27

PubCAS formats source data, connects references and computes explicitly labelled conversions. CAS cross-references are supplied by ChEBI; they do not constitute CAS verification or endorsement.

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