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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.

Chemical structure

Computed structure properties
Molecular formulaC8H10N2S
Charge0
Average mass166.249 Da
Monoisotopic mass166.05647 Da
SourceChEBI
InChIKeyAEOCXXJPGCBFJA-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

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

Activity roles

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

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
SourceNative IDLabelMinted CURIEVersion
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).

Mechanism summary

Clinical status
APPROVED

Activity spectrum

Measured or curated activity against specific taxa. A number without a method is not an observation — every row here carries an assay.

283 observations · Browse all observations · Complete record (JSON.gz)

Observations 1–20 of 283

Activity observations
OrganismActivityMICDisk diffusionAssayStrainSample/genomeEvidence
Mycobacterium tuberculosis complex RESISTANT — — CRyPTIC DST; CLIRES2020; liquid media; MGIT; MGIT960 — 1382 source isolates
1382 measurements
Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex SUSCEPTIBLE — — CRyPTIC DST; CLIRES2020; liquid media; MGIT; MGIT960 — 2935 source isolates
2935 measurements
Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex SUSCEPTIBLE — — CRyPTIC DST; CLIRES2020; liquid media; microdilution plate; MODS — 1 source isolates
1 measurements
Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex SUSCEPTIBLE — — CRyPTIC DST; CLIRES2020; not specified — 8 source isolates
8 measurements
Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex INTERMEDIATE — — CRyPTIC DST; CLIRES2020; solid media — 4 source isolates
4 measurements
Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex RESISTANT — — CRyPTIC DST; CLIRES2020; solid media — 362 source isolates
362 measurements
Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex SUSCEPTIBLE — — CRyPTIC DST; CLIRES2020; solid media — 804 source isolates
804 measurements
Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex INTERMEDIATE — — CRyPTIC DST; CLIRES2023; liquid media; MGIT; MGIT960 — 1 source isolates
1 measurements
Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex RESISTANT — — CRyPTIC DST; CLIRES2023; liquid media; MGIT; MGIT960 — 264 source isolates
264 measurements
Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex SUSCEPTIBLE — — CRyPTIC DST; CLIRES2023; liquid media; MGIT; MGIT960 — 650 source isolates
650 measurements
Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex SUSCEPTIBLE — — CRyPTIC DST; CLIRES2023; not specified — 1 source isolates
1 measurements
Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex INTERMEDIATE — — CRyPTIC DST; CLIRES2023; solid media — 1 source isolates
1 measurements
Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex RESISTANT — — CRyPTIC DST; CLIRES2023; solid media — 211 source isolates
211 measurements
Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex SUSCEPTIBLE — — CRyPTIC DST; CLIRES2023; solid media — 644 source isolates
644 measurements
Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex SUSCEPTIBLE 0.5 mg/L — CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 4.0 mg/L — 833 source isolates
833 measurements
Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex SUSCEPTIBLE 0.5 mg/L — CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 4.0 mg/L — 69 source isolates
69 measurements
Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex SUSCEPTIBLE 0.5 mg/L — CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 4.0 mg/L — 170 source isolates
170 measurements
Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex SUSCEPTIBLE 1.0 mg/L — CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 4.0 mg/L — 2103 source isolates
2103 measurements
Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex SUSCEPTIBLE 1.0 mg/L — CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 4.0 mg/L — 126 source isolates
126 measurements
Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex SUSCEPTIBLE 1.0 mg/L — CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 4.0 mg/L — 449 source isolates
449 measurements
Evidence Page data (JSON.gz)

Resistance mechanisms

6 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

ANTIBIOTIC_TARGET_ALTERATION 6
ANTIBIOTIC_TARGET_ALTERATION
DeterminantARO IDOrganismGene familiesEvidence
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

  1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

    Seeded from data/raw/ inventories (ARO, CHEBI)

  2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  3. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  4. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  5. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  6. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  7. RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  8. RESEEDED_FROM_SOURCES 2026-09-26 · seed_from_sources

    Re-seeded; changed: activity_spectrum (CRYPTIC 3.4.0). Upstream retrieval date 2026-08-30, unchanged.

  9. RESEEDED_FROM_SOURCES 2026-10-05 · seed_from_sources

    Re-seeded; changed: activity_membership_collections (CRYPTIC 3.4.0). Upstream retrieval date 2026-08-30, unchanged.

Provenance

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

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