nitrofurantoin

CHEBI:71415 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

An imidazolidine-2,4-dione that is hydantoin substituted at position 1 by a [(5-nitro-2-furyl)methylene]amino group. An antibiotic that damages bacterial DNA. — 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

nitrofuran antibioticARO:3004116

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:24628 CHEBI:24628
CHEBI:25558 CHEBI:25558
CHEBI:25807 CHEBI:25807
CHEBI:87230 CHEBI:87230
ARO:3004116 ARO:3004116

Chemical structure

Computed structure properties
Molecular formula	C8H6N4O5
Charge	0
Average mass	238.159 Da
Monoisotopic mass	238.03382 Da
Source	ChEBI
InChIKey	NXFQHRVNIOXGAQ-YCRREMRBSA-N

SMILES

O=C1CN(/N=C/c2ccc([N+](=O)[O-])o2)C(=O)N1

InChI

InChI=1S/C8H6N4O5/c13-6-4-11(8(14)10-6)9-3-5-1-2-7(17-5)12(15)16/h1-3H,4H2,(H,10,13,14)/b9-3+

Also called

nitrofurantoina (INN)— chebi
nitrofurantoine (INN)— chebi
nitrofurantoinum (INN)— chebi
1-{[(5-nitro-2-furyl)methylene]amino}imidazolidine-2,4-dione (EXACT_SYNONYM)— chebi
1-((5-Nitrofurfurylidene)amino)hydantoin (EXACT_SYNONYM)— chebi
1-(5-Nitro-2-furfurylidenamino)hydantoin (EXACT_SYNONYM)— chebi
1-(5-Nitro-2-furfurylideneamino)hydantoin (EXACT_SYNONYM)— chebi
1-[(5-Nitrofurfurylidene)amino]hydantoin (EXACT_SYNONYM)— chebi
5-Nitrofurantoin (EXACT_SYNONYM)— chebi
N-(5-Nitrofurfurylidene)-1-aminohydantoin (EXACT_SYNONYM)— chebi
Chemiofuran (EXACT_SYNONYM)— aro
Cistofuran (EXACT_SYNONYM)— aro
Furadantin (EXACT_SYNONYM)— aro
Furadantine (EXACT_SYNONYM)— aro
Furalan (EXACT_SYNONYM)— aro
Macrobid (EXACT_SYNONYM)— aro
Macrodantin (EXACT_SYNONYM)— aro
Macrodantina (EXACT_SYNONYM)— aro
Nitrofuradantin (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:0000075
cas:67-20-9
drugbank:DB00698
drugcentral:1949
kegg.compound:C07268
kegg.drug:D00439
patent:US2610181
patent:US2898335
patent:US2927110
patent:WO2006019844
patent:WO2008103673
patent:WO2010065110
reaxys:8132135
wikipedia.en:Nitrofurantoin
chembl:CHEMBL572
pubchem.compound:6604200

Activity roles

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

CHEBI:33281 CHEBI:33281
CHEBI:36047 CHEBI:36047

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:0000075`	nitrofurantoin	`antibioticmech:aro-2e74497393`	2026-08-30
CHEBI	`CHEBI:71415`	nitrofurantoin	`antibioticmech:chebi-4ae399c673`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

deoxyribonucleic acid NUCLEIC_ACID ATTACKED_COMPONENT

ARO:3000738

CARD/ARO database assertion; target organism, strain, and assay are not specified. ARO describes DNA strand damage or transcription interference. Evidence status: DATABASE_ASSERTION_ONLY. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3000738 (CARD/ARO asserts targeted_by_antibiotic ARO:0000075 (nitrofurantoin); database assertion, not a primary citation.)

Mechanism summary

Clinical status: APPROVED

Resistance mechanisms

3 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 2

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Escherichia coli nfsA mutations conferring resistance to nitrofurantoin	ARO:3003751	not organism-specific	—	ARO:3003751 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000075 (nitrofurantoin); database assertion, not a primary citation.)
Escherichia coli nfsB with mutation conferring resistance to nitrofurantoin	ARO:3003756	not organism-specific	—	ARO:3003756 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000075 (nitrofurantoin); database assertion, not a primary citation.)

ANTIBIOTIC_EFFLUX 1

ANTIBIOTIC_EFFLUX
Determinant	ARO ID	Organism	Gene families	Evidence
oqxAB	ARO:3003921	not organism-specific	—	ARO:3003921 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000075 (nitrofurantoin); 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 2026-08-31 · 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.