prothionamide

CHEBI:32066 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

Prothionamide is a thioamide derivative with antibacterial properties. It increases cell wall permeability and decreases cell wall damage resistance by inhibition of mycolic acid synthesis, resulting in cell death. It is particularly used to treat M. tuberculosis and M. leprae infections. — PMID:6459296

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.

thioamide antibiotic ARO:3007156

Chemical structure

Computed structure properties
Molecular formula	C9H12N2S
Charge	0
Average mass	180.276 Da
Monoisotopic mass	180.07212 Da
Source	ChEBI
InChIKey	VRDIULHPQTYCLN-UHFFFAOYSA-N

SMILES

CCCc1cc(C(N)=S)ccn1

InChI

InChI=1S/C9H12N2S/c1-2-3-8-6-7(9(10)12)4-5-11-8/h4-6H,2-3H2,1H3,(H2,10,12)

Also called

protionamide (EXACT_SYNONYM)— aro

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.

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:3004025`	prothionamide	`antibioticmech:aro-399b14c9b0`	2026-08-30

Activity spectrum

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

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

Activity observations
Organism	Activity	MIC	Disk diffusion	Assay	Strain	Sample/genome	Evidence
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; CLIRES2020; liquid media; MGIT; MGIT960	—	1 source isolates 1 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; CLIRES2020; liquid media; MGIT; MGIT960	—	5 source isolates 5 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; CLIRES2020; not specified	—	2 source isolates 2 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; CLIRES2020; solid media	—	11 source isolates 11 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; CLIRES2020; solid media	—	757 source isolates 757 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; CLIRES2023; liquid media; MGIT; MGIT960	—	1 source isolates 1 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; CLIRES2023; liquid media; MGIT; MGIT960	—	1 source isolates 1 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	RESISTANT	—	—	CRyPTIC DST; PHE2019; liquid media; MGIT; MGIT960; critical concentration WHO mg/L	—	45 source isolates 45 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; PHE2019; liquid media; MGIT; MGIT960; critical concentration WHO mg/L	—	149 source isolates 149 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; SEQTREAT2020; liquid media; MGIT; MGIT960; critical concentration WHO mg/L	—	246 source isolates 246 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; SEQTREAT2020; liquid media; MGIT; MGIT960; critical concentration WHO mg/L	—	214 source isolates 214 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	—	—	—	CRyPTIC DST; SEQTREAT2020; liquid media; MGIT; MGIT960; critical concentration WHO mg/L	—	296 source isolates 296 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; SEQTREAT2020; liquid media; MGIT; critical concentration WHO mg/L	—	535 source isolates 535 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; SEQTREAT2020; liquid media; MGIT; critical concentration WHO mg/L	—	888 source isolates 888 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	—	—	—	CRyPTIC DST; SEQTREAT2020; liquid media; MGIT; critical concentration WHO mg/L	—	57 source isolates 57 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; SEQTREAT2020; solid media; LJ; critical concentration WHO mg/L	—	83 source isolates 83 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; SEQTREAT2020; solid media; LJ; critical concentration WHO mg/L	—	80 source isolates 80 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	—	—	—	CRyPTIC DST; SEQTREAT2020; solid media; LJ; critical concentration WHO mg/L	—	15 source isolates 15 measurements	Evidence Page data (JSON.gz)

Resistance mechanisms

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

ANTIBIOTIC_TARGET_ALTERATION 4

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Mycobacterium tuberculosis ethA mutations conferring resistance to prothionamide	ARO:3005106	not organism-specific	—	ARO:3005106 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3004025 (prothionamide); database assertion, not a primary citation.)
Mycobacterium tuberculosis fabG1 with mutations conferring resistance to prothionamide	ARO:3007811	not organism-specific	—	ARO:3007811 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3004025 (prothionamide); database assertion, not a primary citation.)
Mycobacterium tuberculosis katG mutations conferring resistance to prothionamide	ARO:3005102	not organism-specific	—	ARO:3005102 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3004025 (prothionamide); database assertion, not a primary citation.)
Mycobacterium tuberculosis mshA mutations conferring resistance to prothionamide	ARO:3005108	not organism-specific	—	ARO:3005108 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3004025 (prothionamide); 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 2026-09-26 · seed_from_sources
Re-seeded; changed: activity_spectrum (CRYPTIC 3.4.0). Upstream retrieval date 2026-08-30, unchanged.
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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