N-butyl-5-(4-hydroxyphenyl)-6-oxo-1,6-dihydropyrazine-2-carboxamide

CHEBI:167182 ·resolve ·ANTIMYCOBACTERIAL ·EXACT SEEDED

A pyrazinecarboxamide in which a 6-oxo-1,6-dihydropyrazine nucleus is substituted on C-5 by a 4-hydroxyphenyl group and on C-2 by a butylcarbamyl group. A synthetic determinant of cefadroxil, it is a promising tool for determining in vitro cross-reactivity to cefadroxil in amoxicillin-allergic patients. — 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

Strictly broader compounds or drug classes this molecule belongs to.

pyrazinecarboxamide CHEBI:45285

Chemical structure

Computed structure properties
Molecular formula	C15H17N3O3
Charge	0
Average mass	287.319 Da
Monoisotopic mass	287.12699 Da
Source	ChEBI
InChIKey	HURXYEZMLXEXLD-UHFFFAOYSA-N

SMILES

CCCCNC(=O)c1cnc(-c2ccc(O)cc2)c(=O)n1

InChI

InChI=1S/C15H17N3O3/c1-2-3-8-16-14(20)12-9-17-13(15(21)18-12)10-4-6-11(19)7-5-10/h4-7,9,19H,2-3,8H2,1H3,(H,16,20)(H,18,21)

Also called

N-butyl-1,6-dihydro-5-(4-hydroxyphenyl)-6-oxo-2-pyrazinecarboxamide (EXACT_SYNONYM)— chebi

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
CHEBI	`CHEBI:167182`	N-butyl-5-(4-hydroxyphenyl)-6-oxo-1,6-dihydropyrazine-2-carboxamide	`antibioticmech:chebi-211858339d`	2026-08-30

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (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.