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.
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
Equivalent identifiers for this same structure in other resources.
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 |
Resistance mechanisms
4 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 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
Provenance
Seeded by scripts/seed_from_sources.py from the committed
inventories in data/raw/.
View the record.