Nitrofurantoin (CHEM002123)

Record Information
Version1.0
Creation Date2009-07-15 20:48:38 UTC
Update Date2026-05-14 16:46:23 UTC
Accession NumberCHEM002123
Identification
Common NameNitrofurantoin
ClassSmall Molecule
Description
A bacteriostatic or bactericidal agent depending on the concentration and susceptibility of the infecting organism. Nitrofurantoin is active against some gram positive organisms such as S. aureus, S. epidermidis, S. saprophyticus, Enterococcus faecalis, S. agalactiae, group D streptococci, viridians streptococci and Corynebacterium. Its spectrum of activity against gram negative organisms includes E. coli, Enterobacter, Neisseria, Salmonella and Shigella. It may be used as an alternative to trimethoprim/sulfamethoxazole for treating urinary tract infections though it may be less effective at eradicating vaginal bacteria. May also be used in females as prophylaxis against recurrent cystitis related to coitus. Nitrofurantoin is highly stable to the development of bacterial resistance, a property thought to be due to its multiplicity of mechanisms of action.
Contaminant Sources
  • HMDB Contaminants - Urine
  • IARC Carcinogens Group 3
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Amine
  • Anti-Infective Agent
  • Anti-Infective Agent, Urinary
  • Drug
  • Human Neurotoxin
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
FuradantineHMDB
FuradonineHMDB
MacrodantinHMDB
Nitrofurantoin, monohydrateHMDB
FuradoineHMDB
Monohydrate nitrofurantoinHMDB
Nitrofurantoin sodium saltHMDB
FurantoinHMDB
FuradantinMeSH
Chemical FormulaC8H6N4O5
Average Molecular Mass238.157 g/mol
Monoisotopic Mass238.034 g/mol
CAS Registry Number67-20-9
IUPAC Name1-[(Z)-[(5-nitrofuran-2-yl)methylidene]amino]imidazolidine-2,4-dione
Traditional Namenitrofurantoin
SMILES[O-][N+](=O)C1=CC=C(O1)\C=N/N1CC(=O)NC1=O
InChI IdentifierInChI=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-
InChI KeyNXFQHRVNIOXGAQ-OQFOIZHKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydantoins. These are heterocyclic compounds containing an imidazolidine substituted by ketone group at positions 2 and 4.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzolidines
Sub ClassImidazolidines
Direct ParentHydantoins
Alternative Parents
Substituents
  • Hydantoin
  • Alpha-amino acid or derivatives
  • Nitroaromatic compound
  • 2-nitrofuran
  • Semicarbazone
  • Dicarboximide
  • Furan
  • Heteroaromatic compound
  • Semicarbazide
  • C-nitro compound
  • Carbonic acid derivative
  • Organic nitro compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Azacycle
  • Oxacycle
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid derivative
  • Organic oxoazanium
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic zwitterion
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceSolid (1).
Experimental Properties
PropertyValue
Melting Point223-228°C
Boiling PointNot Available
Solubility79.5 mg/L (at 24°C)
Predicted Properties
PropertyValueSource
Water Solubility0.42 g/LALOGPS
logP0.03ALOGPS
logP-0.22ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)9.23ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area120.73 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity53.11 m³·mol⁻¹ChemAxon
Polarizability19.75 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureOral. Readily absorbed in GI tract primarily in small intestine. Enhanced by food or delayed gastric emptying via enhanced dissolution rate of the drug.
Mechanism of ToxicityNitrofurantoin is activated by bacterial flavoproteins (nitrofuran reductase) to active reduced reactive intermediates that are thought to modulate and damage ribosomal proteins or other macromolecules, especially DNA, causing inhibition of DNA, RNA, protein, and cell wall synthesis. Nitrofurantoin inhibits bacterial acetyl-coenzyme A, interfering with the organism's carbohydrate metabolism. The drug also can disrupt bacterial cell wall formation. The overall effect is inhibition of bacterial growth or cell death.
MetabolismHepatic (75%) (3). Partially metabolized in liver to aminofurantoin. Half Life: 0.3-1 hour
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (2)
Uses/SourcesMay be used as an alternative in the treatment of urinary tract infections. May be used by females pericoitally for prophylaxis against recurrent cystitis related to coitus.
Minimum Risk LevelNot Available
Health EffectsSialadenitis, pancreatitis, peripheral neuropathy, Asthenia, vertigo, and nystagmus, benign intracranial hypertension (pseudotumor cerebri), confusion, depression, optic neuritis, and psychotic reactions (1).
SymptomsAcute toxicity may cause vomiting. Adverse effects include nausea and urine discolouration. Rare hepatotoxic and hypersensitivity reactions have occurred. Hemolytic anemia is a risk in patients with G6PD deficiency. Ascending polyneuropathy may occur with prolonged therapy or in patients with low creatinine clearance.
TreatmentThere is no specific antidote, but a high fluid intake should be maintained to promote urinary excretion of the drug. Nitrofurantoin is dialyzable. (4)
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0014836
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNitrofurantoin
Chemspider ID4510228
ChEBI ID1039679
PubChem Compound ID5353830
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Tara Bielski, Kerry Benson, “Novel orally administrable formulation of nitrofurantoin and a method for preparing said formulation.” U.S. Patent US20050202079, issued September 15, 2005.

MSDSLink
General References