Chemical substance record

Nitrofurantoin

67-20-9C₈H₆N₄O₅238.159 g/mol

Organic/Inorganic Small MoleculeChEBI source record

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

Safety references

Safety documents & references

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Identity & molecular properties

Source-linked values

CAS number	67-20-9	ChEBI ↗
Molecular formula	C₈H₆N₄O₅	ChEBI ↗
Molar mass	238.159 g/mol	ChEBI ↗
Monoisotopic mass	238.03382 Da	ChEBI ↗
Formal charge	0	ChEBI ↗
ChEBI identifier	CHEBI:71415	ChEBI ↗

Cross-source molecular data

PubChem

Molar mass	238.16 g/mol	PubChem ↗
Exact mass	238.03381930 Da	PubChem ↗
Computed XLogP	-0.5	PubChem ↗
Topological polar surface area (Å²)	121	PubChem ↗
H-bond donors	1	PubChem ↗
H-bond acceptors	6	PubChem ↗
Rotatable bonds	2	PubChem ↗

PubChem computed values are shown separately from the ChEBI record. An exact InChIKey match was used to connect the records. Molecular descriptors do not describe a supplied product’s purity, particle size or performance.

Names & structural identifiers

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Source preferred name

nitrofurantoin

IUPAC name

1-{[(5-nitro-2-furyl)methylene]amino}imidazolidine-2,4-dione

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+

Names & synonyms

1-{[(5-nitro-2-furyl)methylene]amino}imidazolidine-2,4-dionenitrofurantoinanitrofurantoinenitrofurantoinum

Names are supplied by ChEBI. Trade names and related synonyms may describe a broader product context.

Classification & relationships

ChEBI ontology

imidazolidine-2,4-dioneChEBI parent class · 24628 ↗organonitrogen heterocyclic antibioticChEBI parent class · 25558 ↗organooxygen heterocyclic antibioticChEBI parent class · 25807 ↗nitrofuran antibioticChEBI parent class · 87230 ↗

organic heterocyclic compound organic molecular entity

Roles recorded in ChEBI

antimicrobial agentantibacterial agentantiinfective agentantibacterial drughepatotoxic agent

Database role annotations describe reported biological or chemical roles; they are not product approvals or recommendations for use.

Mass ↔ amount of substance

Calculated from sourced mass

Amount

Input unit

Equivalent amount

0.00419888 mol

Uses 238.159 g/mol from ChEBI. Assumes the substance described by this record; no purity or concentration correction is applied.

Elemental composition

Theoretical mass fractions

C

Carbon · 8 atoms

40.35%

O

Oxygen · 5 atoms

33.59%

N

Nitrogen · 4 atoms

23.53%

H

Hydrogen · 6 atoms

2.54%

Calculated theoretical mass fractions from the reported formula and PubChem periodic-table atomic masses. These are not assay or purity results.

Research & patent references

Selected source associations

Risk factors for urosepsis following percutaneous nephrolithotomy: role of 1 week of nitrofurantoin in reducing the risk of urosepsis. ↗Urological research · 2012 Feb · PMID 21567157

Prediction of the mode of interaction between monoterpenes and the nitroreductase from Enterobacter cloacae by docking simulation. ↗Computers in biology and medicine · 2012 Apr · PMID 22240115

US2610181 · Patent reference ↗Patent cross-reference supplied by ChEBI. Association alone does not establish claim scope.

US2898335 · Patent reference ↗Patent cross-reference supplied by ChEBI. Association alone does not establish claim scope.

US2927110 · Patent reference ↗Patent cross-reference supplied by ChEBI. Association alone does not establish claim scope.

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Sources & record history

Checked 27 Sep 2026

Identity, formula, mass, synonyms & ontologyEMBL-EBI ChEBI · CHEBI:71415

Release 255, 9 September 2026. ChEBI three-star (manually annotated) source entry. View original record ↗ · CC BY 4.0

Additional molecular descriptorsNCBI PubChem · CID 6604200 · retrieved 2026-09-27

PubCAS formats source data, connects references and computes explicitly labelled conversions. CAS cross-references are supplied by ChEBI; they do not constitute CAS verification or endorsement.

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