Nitrofurantoin
Athanor · official
C8H6N4O5 · 238.16 g/mol
IUPAC name: 1-[(5-nitrofuran-2-yl)methylideneamino]imidazolidine-2,4-dione
Also called Macrobid, Macrodantin, urinary antibiotic
Names and identifiers
- IUPAC name
- 1-[(5-nitrofuran-2-yl)methylideneamino]imidazolidine-2,4-dione
- Synonyms
- Macrobid, Macrodantin, urinary antibiotic
+ 40 more
Furantoin, RefChem:921925, 1-[(5-nitro-2-furanyl)methylideneamino]imidazolidine-2,4-dione, C8H6N4O5, Spectrum_001003, Prestwick0_000168, Prestwick1_000168, Spectrum2_001046, Spectrum3_000517, Spectrum4_000075, Oprea1_199544, Oprea1_513843, SCHEMBL29472, KBioGR_000629, KBioSS_001483, DivK1c_000224, SPBio_000972, SPBio_001956, orb1309017, CHEMBL1605821, KBio1_000224, KBio2_001483, KBio2_004051, KBio2_006619, KBio3_001573, NINDS_000224, HMS2231I15, HMS3259E21, HMS3374M07, Nitrofurantoin - Bio-X trade mark, s4536, AKOS028110053, NC00521, 1-(5'-nitrofurfurylideneamino)hydantoin, FN182931, SY076779, DB-054997, NS00001691, Q27167045, 1-[(5-nitro-2-furyl)methyleneamino]imidazolidine-2,4-dione
- Molecular formula
- C8H6N4O5
- Empirical formula
- C8H6N4O5
- Molecular weight
- 238.16 g/mol
- Exact mass
- 238.03382
- CAS number
- 67-20-9
- PubChem CID
- 4509
- Canonical SMILES
- C1C(=O)NC(=O)N1N=CC2=CC=C(O2)[N+](=O)[O-]
- Isomeric SMILES
- C1C(=O)NC(=O)N1N=CC2=CC=C(O2)[N+](=O)[O-]
- 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)
- InChIKey
- NXFQHRVNIOXGAQ-UHFFFAOYSA-N
- Molfile
Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.
Calculated
- Heavy atoms
- 17
- Rings
- 2
- Aromatic rings
- 1
- Fraction sp³ carbons (Fsp3)
- 0.12
- H-bond donors
- 1
- H-bond acceptors
- 6
- Rotatable bonds
- 3 computed here · PubChem 2
- TPSA (Ų)
- 118.1 computed here · PubChem 121
- Formal charge
- 0
- XLogP3
- -0.5 PubChem
- Complexity
- 390 PubChem
- Stereocenters
- None
- Double-bond geometry
- None specified
- Point group
- Cs of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)
Elemental analysis
- C40.35%
- H2.54%
- N23.53%
- O33.59%
Isotope pattern
Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.
Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.
Predicted
- log P
- 0.07 Crippen (Wildman and Crippen 1999)
- log S (water solubility)
- -1.38 ESOL (Delaney 2004), log mol/L
- Synthetic accessibility
- 2.94 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)
Drug-likeness: Lipinski’s rule of five
- Molecular weight ≤ 500: 238.16
- log P ≤ 5 (Crippen): 0.07
- H-bond donors ≤ 5: 1
- H-bond acceptors ≤ 10: 6
Passes all four rules.
¹³C NMR shifts, predicted
Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.
Safety
No GHS hazard classification was found in the sources.
Safety data sheets on the supplier’s page: A2B Chem, Angene Chemical, AKos Consulting & Solutions.
Always read the supplier’s safety data sheet before working with it.
Spectra
- LC-MSMassBank Europe (TripleTOF 5600 SCIEX · LC-ESI-QTOF · POSITIVE) · MassBank Europe (TripleTOF 5600 SCIEX · LC-ESI-QTOF · POSITIVE) · MassBank Europe (TripleTOF 5600 SCIEX · LC-ESI-QTOF · POSITIVE) · MassBank Europe (Q Exactive Plus · LC-ESI-QFT · POSITIVE) · MassBank Europe (Q Exactive Plus · LC-ESI-QFT · POSITIVE) · MassBank Europe (Q Exactive Plus · LC-ESI-QFT · POSITIVE)
Experimental spectra held by these sources; each link opens the source's own record.
Literature
Reading PubChem, OpenAlex and GSRS…
Bioactivity
Reading ChEMBL…
References
- [1]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
- ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
- ·Literature on PubChem
Data last updated 2026-10-14.