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.

Label unavailable CHEBI:29347
Label unavailable CHEBI:38314
Label unavailable CHEBI:83628
pyrazine antibiotic 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

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.

wikipedia.en:Pyrazinamide

Activity roles

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

antitubercular agent 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

Activity spectrum

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

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

Activity observations
Organism	Activity	MIC	Disk diffusion	Assay	Strain	Sample/genome	Evidence
Mycobacterium tuberculosis complex	INTERMEDIATE	—	—	CRyPTIC DST; CLIRES2020; liquid media; MGIT; MGIT960	—	2 source isolates 2 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; CLIRES2020; liquid media; MGIT; MGIT960	—	168 source isolates 168 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; CLIRES2020; liquid media; MGIT; MGIT960	—	410 source isolates 410 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; CLIRES2020; not specified	—	88 source isolates 88 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; CLIRES2020; not specified	—	320 source isolates 320 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	INTERMEDIATE	—	—	CRyPTIC DST; CLIRES2020; solid media	—	2 source isolates 2 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; CLIRES2020; solid media	—	357 source isolates 357 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; CLIRES2020; solid media	—	466 source isolates 466 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	INTERMEDIATE	—	—	CRyPTIC DST; CLIRES2023; liquid media; MGIT; MGIT960	—	2 source isolates 2 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; CLIRES2023; liquid media; MGIT; MGIT960	—	44 source isolates 44 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; CLIRES2023; liquid media; MGIT; MGIT960	—	60 source isolates 60 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; CLIRES2023; not specified	—	3 source isolates 3 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; CLIRES2023; not specified	—	2 source isolates 2 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	INTERMEDIATE	—	—	CRyPTIC DST; CLIRES2023; solid media	—	2 source isolates 2 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; CLIRES2023; solid media	—	196 source isolates 196 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; CLIRES2023; solid media	—	476 source isolates 476 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; KMMYKROBE2025; not specified	—	2 source isolates 2 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; KMMYKROBE2025; not specified	—	8 source isolates 8 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; KMVALIDATION2025; not specified	—	1470 source isolates 1470 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; KMVALIDATION2025; not specified	—	4379 source isolates 4379 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; LID2015; liquid media; MGIT; MGIT960; critical concentration WHO mg/L	—	187 source isolates 187 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; LID2015; liquid media; MGIT; MGIT960; critical concentration WHO mg/L	—	2697 source isolates 2697 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; LID2015; solid media; marks biphasic method; critical concentration WHO mg/L	—	52 source isolates 52 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; LID2015; solid media; marks biphasic method; critical concentration WHO mg/L	—	454 source isolates 454 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; NEJM2018; liquid media; MGIT; MGIT960; critical concentration 100.0 mg/L	—	692 source isolates 692 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; NEJM2018; liquid media; MGIT; MGIT960; critical concentration 100.0 mg/L	—	5303 source isolates 5303 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; NEJM2018; liquid media; MGIT; MGIT960	—	20 source isolates 20 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; NEJM2018; liquid media; MGIT; MGIT960	—	152 source isolates 152 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; NEJM2018; solid media; LJ; proportion method; critical concentration 100.0 mg/L	—	145 source isolates 145 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; NEJM2018; solid media; LJ; proportion method; critical concentration 100.0 mg/L	—	258 source isolates 258 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; NEJM2018; solid media; marks biphasic method	—	282 source isolates 282 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; NEJM2018; solid media; marks biphasic method	—	942 source isolates 942 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; PHE2019; liquid media; MGIT; MGIT960; critical concentration WHO mg/L	—	152 source isolates 152 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; PHE2019; liquid media; MGIT; MGIT960; critical concentration WHO mg/L	—	1405 source isolates 1405 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; PHE2019; solid media; marks biphasic method; critical concentration WHO mg/L	—	115 source isolates 115 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; PHE2019; solid media; marks biphasic method; critical concentration WHO mg/L	—	2540 source isolates 2540 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; SEQTREAT2020; liquid media; MGIT; BACTEC460; critical concentration 100.0 mg/L	—	2 source isolates 2 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; SEQTREAT2020; liquid media; MGIT; BACTEC460; critical concentration 100.0 mg/L	—	68 source isolates 68 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; SEQTREAT2020; liquid media; MGIT; MGIT960; critical concentration 100.0 mg/L	—	221 source isolates 221 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; SEQTREAT2020; liquid media; MGIT; MGIT960; critical concentration 100.0 mg/L	—	2606 source isolates 2606 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	—	—	—	CRyPTIC DST; SEQTREAT2020; liquid media; MGIT; MGIT960; critical concentration 100.0 mg/L	—	19 source isolates 19 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; SEQTREAT2020; liquid media; MGIT; MGIT960; critical concentration WHO mg/L	—	146 source isolates 146 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; SEQTREAT2020; liquid media; MGIT; MGIT960; critical concentration WHO mg/L	—	356 source isolates 356 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	—	—	—	CRyPTIC DST; SEQTREAT2020; liquid media; MGIT; MGIT960; critical concentration WHO mg/L	—	254 source isolates 254 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; SEQTREAT2020; liquid media; MGIT; critical concentration WHO mg/L	—	676 source isolates 676 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; SEQTREAT2020; liquid media; MGIT; critical concentration WHO mg/L	—	733 source isolates 733 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	—	—	—	CRyPTIC DST; SEQTREAT2020; liquid media; MGIT; critical concentration WHO mg/L	—	71 source isolates 71 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; SEQTREAT2020; not specified	—	10 source isolates 10 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; SEQTREAT2020; not specified	—	479 source isolates 479 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	—	—	—	CRyPTIC DST; SEQTREAT2020; not specified	—	71 source isolates 71 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; SEQTREAT2020; solid media; LJ; critical concentration WHO mg/L	—	51 source isolates 51 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; SEQTREAT2020; solid media; LJ; critical concentration WHO mg/L	—	70 source isolates 70 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	—	—	—	CRyPTIC DST; SEQTREAT2020; solid media; LJ; critical concentration WHO mg/L	—	57 source isolates 57 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; WHO2019; liquid media; MGIT; MGIT960; critical concentration 100.0 mg/L	—	70 source isolates 70 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; WHO2019; liquid media; MGIT; MGIT960; critical concentration 100.0 mg/L	—	104 source isolates 104 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; WHO2019; liquid media; MGIT; MGIT960; critical concentration WHO mg/L	—	317 source isolates 317 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; WHO2019; liquid media; MGIT; MGIT960; critical concentration WHO mg/L	—	618 source isolates 618 measurements	Evidence Page data (JSON.gz)

Resistance mechanisms

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

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
RESEEDED_FROM_SOURCES 2026-09-10 · 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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