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.

Label unavailable CHEBI:24628
organonitrogen heterocyclic antibiotic CHEBI:25558
Label unavailable CHEBI:25807
nitrofuran antibiotic CHEBI:87230
nitrofuran antibiotic 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

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.

Activity roles

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

antimicrobial agent CHEBI:33281
antibacterial drug 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

Activity spectrum

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

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

Activity observations
Organism	Activity	MIC	Disk diffusion	Assay	Strain	Sample/genome	Evidence
Enterobacter cloacae complex NCBITaxon:354276	—	128.0 mg/L	—	Broth microdilution nitrofurantoin MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	1151	BioSample SAMN34111338	Evidence Page data (JSON.gz)
Klebsiella pneumoniae NCBITaxon:573	—	>128.0 mg/L	—	Broth microdilution nitrofurantoin MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	1153	BioSample SAMN34111340	Evidence Page data (JSON.gz)
Klebsiella pneumoniae NCBITaxon:573	—	>128.0 mg/L	—	Broth microdilution nitrofurantoin MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	1158	BioSample SAMN34111344	Evidence Page data (JSON.gz)
Klebsiella pneumoniae NCBITaxon:573	—	>128.0 mg/L	—	Broth microdilution nitrofurantoin MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	1163	BioSample SAMN34111349	Evidence Page data (JSON.gz)

Resistance mechanisms

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

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
RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories
CURATED_RESISTANT_TAXA 2026-09-13 · codex · LLM-assisted
Added 4 stable-URL CDC/FDA AR Isolate Bank nitrofurantoin-resistant Multi-Mechanism panel MIC observations for AR-1151, AR-1153, AR-1158, and AR-1163.
STRUCTURED_ACTIVITY_BIOSAMPLE_ACCESSIONS 2026-09-26 · codex · LLM-assisted
Structured BioSample accessions on 4 activity_spectrum observation(s) where evidence notes already named exactly one accession.

Provenance

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

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