pyrazinecarboxamide

CHEBI:45285 ·resolve ·ANTIMYCOBACTERIAL ·EXACT SEEDED

A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of pyrazinoic acid (pyrazine-2-carboxylic acid) with ammonia. A prodrug for pyrazinoic acid, pyrazinecarboxamide is used as part of multidrug regimens for the treatment of tuberculosis. — 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

pyrazine antibioticARO:3007155

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:29347 CHEBI:29347
CHEBI:38314 CHEBI:38314
CHEBI:83628 CHEBI:83628
ARO:3007155 ARO:3007155

Chemical structure

Computed structure properties
Molecular formula	C5H5N3O
Charge	0
Average mass	123.115 Da
Monoisotopic mass	123.04326 Da
Source	ChEBI
InChIKey	IPEHBUMCGVEMRF-UHFFFAOYSA-N

SMILES

NC(=O)c1cnccn1

InChI

InChI=1S/C5H5N3O/c6-5(9)4-3-7-1-2-8-4/h1-3H,(H2,6,9)

Also called

pyrazinamida (INN)— chebi
pyrazinamide (INN)— chebi
pyrazinamidum (INN)— chebi
pyrazine-2-carboxamide (EXACT_SYNONYM)— chebi
2-carbamylpyrazine (EXACT_SYNONYM)— chebi
2-pyrazinecarboxamide (EXACT_SYNONYM)— chebi
PYRAZINE-2-CARBOXAMIDE (EXACT_SYNONYM)— chebi
Pyrazinamide (EXACT_SYNONYM)— chebi
Pyrazinoic acid amide (EXACT_SYNONYM)— chebi
pyrazine carboxamide (EXACT_SYNONYM)— chebi
pyrazineamide (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3003413
beilstein:112306
cas:98-96-4
drugbank:DB00339
drugcentral:2328
gmelin:279021
hmdb:HMDB0014483
kegg.compound:C01956
kegg.drug:D00144
lincs.smallmolecule:LSM-5425
pdb-ccd:PZA
reaxys:112306
wikipedia.en:Pyrazinamide
chembl:CHEMBL614
pubchem.compound:1046

Activity roles

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

CHEBI:33231 CHEBI:33231

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:3003413`	pyrazinamide	`antibioticmech:aro-27a9b8cfeb`	2026-08-30
CHEBI	`CHEBI:45285`	pyrazinecarboxamide	`antibioticmech:chebi-b8efc47dfc`	2026-08-30

Mechanism summary

Clinical status: APPROVED

Resistance mechanisms

12 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 12

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Mycobacterium tuberculosis Rv0191 mutations confer resistance to pyrazinamide	ARO:3004981	not organism-specific	—	ARO:3004981 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3003413 (pyrazinamide); database assertion, not a primary citation.)
Mycobacterium tuberculosis Rv1258c mutations confer resistance to pyrazinamide, isoniazid, and streptomycin	ARO:3007186	not organism-specific	—	ARO:3007186 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3003413 (pyrazinamide); database assertion, not a primary citation.)
Mycobacterium tuberculosis Rv1667 mutations confer resistance to pyrazinamide	ARO:3004984	not organism-specific	—	ARO:3004984 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3003413 (pyrazinamide); database assertion, not a primary citation.)
Mycobacterium tuberculosis Rv2731 mutations confer resistance to pyrazinamide	ARO:3004987	not organism-specific	—	ARO:3004987 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3003413 (pyrazinamide); database assertion, not a primary citation.)
Mycobacterium tuberculosis Rv3169 mutations confer resistance to pyrazinamide	ARO:3004993	not organism-specific	—	ARO:3004993 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3003413 (pyrazinamide); database assertion, not a primary citation.)
Mycobacterium tuberculosis clpC1 with mutation conferring resistance to pyrazinamide	ARO:3004957	not organism-specific	—	ARO:3004957 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3003413 (pyrazinamide); database assertion, not a primary citation.)
Mycobacterium tuberculosis gpsI with mutations conferring resistance to pyrazinamide	ARO:3004977	not organism-specific	—	ARO:3004977 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3003413 (pyrazinamide); database assertion, not a primary citation.)
Mycobacterium tuberculosis mas mutations confer resistance to pyrazinamide	ARO:3004978	not organism-specific	—	ARO:3004978 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3003413 (pyrazinamide); database assertion, not a primary citation.)
Mycobacterium tuberculosis pncA mutations conferring resistance to pyrazinamide	ARO:3003394	not organism-specific	—	ARO:3003394 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3003413 (pyrazinamide); database assertion, not a primary citation.)
Mycobacterium tuberculosis ppsC mutations confer resistance to pyrazinamide	ARO:3004975	not organism-specific	—	ARO:3004975 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3003413 (pyrazinamide); database assertion, not a primary citation.)
Mycobacterium tuberculosis ppsD mutations confer resistance to pyrazinamide	ARO:3004976	not organism-specific	—	ARO:3004976 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3003413 (pyrazinamide); database assertion, not a primary citation.)
Mycobacterium tuberculosis rpsA mutations conferring resistance to pyrazinamide	ARO:3004721	not organism-specific	—	ARO:3004721 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3003413 (pyrazinamide); 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

Provenance

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