ethionamide

CHEBI:4885 ·resolve ·ANTIMYCOBACTERIAL ·EXACT SEEDED

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

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

thioamide antibioticARO:3007156

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:26421 CHEBI:26421
CHEBI:47956 CHEBI:47956
ARO:3007156 ARO:3007156

Chemical structure

Computed structure properties
Molecular formula	C8H10N2S
Charge	0
Average mass	166.249 Da
Monoisotopic mass	166.05647 Da
Source	ChEBI
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)

Also called

Trecator (BRAND_NAME)— chebi
ethionamidum (INN)— chebi
etionamida (INN)— chebi
2-ethylpyridine-4-carbothioamide (EXACT_SYNONYM)— chebi
2-ethyl-4-thiopyridylamide (EXACT_SYNONYM)— chebi
ETH (EXACT_SYNONYM)— chebi
ETP (EXACT_SYNONYM)— chebi
Ethinamide (EXACT_SYNONYM)— chebi
Ethionamide (EXACT_SYNONYM)— chebi
Ethioniamide (EXACT_SYNONYM)— chebi
Ethylisothiamide (EXACT_SYNONYM)— chebi
Ethyonomide (EXACT_SYNONYM)— chebi
Etionamid (EXACT_SYNONYM)— chebi
Etionamide (EXACT_SYNONYM)— chebi
Etioniamid (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3003474
cas:536-33-4
drugbank:DB00609
drugcentral:1083
hmdb:HMDB0014747
kegg.compound:C07665
kegg.drug:D00591
lincs.smallmolecule:LSM-5620
patent:GB800250
reaxys:116474
wikipedia.en:Ethionamide
chembl:CHEMBL1441
pubchem.compound:2761171

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:33231 CHEBI:33231
CHEBI:35816 CHEBI:35816

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
ARO	`ARO:3003474`	ethionamide	`antibioticmech:aro-64cc27ec2b`	2026-08-30
CHEBI	`CHEBI:4885`	ethionamide	`antibioticmech:chebi-276193be4e`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

Antibiotic sensitive ethA PROTEIN REQUIRED_UPTAKE_OR_ACTIVATION_FACTOR

ARO:3003475

CARD/ARO database assertion; target organism, strain, and assay are not specified. EthA activates thiocarbamide prodrugs into cytotoxic species. Evidence status: DATABASE_ASSERTION_ONLY. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3003475 (CARD/ARO asserts targeted_by_antibiotic ARO:3003474 (ethionamide); database assertion, not a primary citation.)

Mechanism summary

Clinical status: APPROVED

Resistance mechanisms

6 known routes by which microbes resist this compound, grounded in ARO where CARD models them. Grouped by mechanism type — expand a group to see its determinants.

ANTIBIOTIC_TARGET_ALTERATION 6

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Mycobacterium tuberculosis Rv0565c mutation conferring resistance to ethionamide	ARO:3004955	not organism-specific	—	ARO:3004955 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3003474 (ethionamide); database assertion, not a primary citation.)
Mycobacterium tuberculosis ethA with mutation conferring resistance to ethionamide	ARO:3003458	not organism-specific	—	ARO:3003458 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3003474 (ethionamide); database assertion, not a primary citation.)
Mycobacterium tuberculosis fabG1 mutation conferring resistance to ethionamide	ARO:3004933	not organism-specific	—	ARO:3004933 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3003474 (ethionamide); database assertion, not a primary citation.)
Mycobacterium tuberculosis inhA mutations conferring resistance to ethionamide	ARO:3004876	not organism-specific	—	ARO:3004876 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3003474 (ethionamide); database assertion, not a primary citation.)
Mycobacterium tuberculosis mshC mutations conferring resistance to ethionamide	ARO:3004934	not organism-specific	—	ARO:3004934 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3003474 (ethionamide); database assertion, not a primary citation.)
Mycobacterium tuberculosis nudC mutations conferring resistance to ethionamide	ARO:3004935	not organism-specific	—	ARO:3004935 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3003474 (ethionamide); database assertion, not a primary citation.)

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (ARO, CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.