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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:45 UTC
HMDB IDHMDB0014836
Secondary Accession Numbers
  • HMDB14836
Metabolite Identification
Common NameNitrofurantoin
DescriptionA 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.
Structure
Data?1582753225
Synonyms
ValueSource
FuradantineHMDB
FuradonineHMDB
MacrodantinHMDB
Nitrofurantoin, monohydrateHMDB
FuradoineHMDB
Monohydrate nitrofurantoinHMDB
Nitrofurantoin sodium saltHMDB
FurantoinHMDB
FuradantinMeSH
Chemical FormulaC8H6N4O5
Average Molecular Weight238.157
Monoisotopic Molecular Weight238.033819322
IUPAC Name1-[(Z)-[(5-nitrofuran-2-yl)methylidene]amino]imidazolidine-2,4-dione
Traditional Namenitrofurantoin
CAS Registry Number67-20-9
SMILES
[O-][N+](=O)C1=CC=C(O1)\C=N/N1CC(=O)NC1=O
InChI Identifier
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-
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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point263 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.42 g/LNot Available
LogP-0.1Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+149.28130932474
DeepCCS[M-H]-147.11730932474
DeepCCS[M-2H]-180.35630932474
DeepCCS[M+Na]+155.19330932474
AllCCS[M+H]+150.432859911
AllCCS[M+H-H2O]+146.532859911
AllCCS[M+NH4]+154.132859911
AllCCS[M+Na]+155.232859911
AllCCS[M-H]-149.132859911
AllCCS[M+Na-2H]-148.832859911
AllCCS[M+HCOO]-148.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Nitrofurantoin[O-][N+](=O)C1=CC=C(O1)\C=N/N1CC(=O)NC1=O2956.7Standard polar33892256
Nitrofurantoin[O-][N+](=O)C1=CC=C(O1)\C=N/N1CC(=O)NC1=O2373.9Standard non polar33892256
Nitrofurantoin[O-][N+](=O)C1=CC=C(O1)\C=N/N1CC(=O)NC1=O2488.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Nitrofurantoin,1TMS,isomer #1C[Si](C)(C)N1C(=O)CN(/N=C\C2=CC=C([N+](=O)[O-])O2)C1=O2455.9Semi standard non polar33892256
Nitrofurantoin,1TMS,isomer #1C[Si](C)(C)N1C(=O)CN(/N=C\C2=CC=C([N+](=O)[O-])O2)C1=O2387.6Standard non polar33892256
Nitrofurantoin,1TMS,isomer #1C[Si](C)(C)N1C(=O)CN(/N=C\C2=CC=C([N+](=O)[O-])O2)C1=O3814.8Standard polar33892256
Nitrofurantoin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)CN(/N=C\C2=CC=C([N+](=O)[O-])O2)C1=O2713.6Semi standard non polar33892256
Nitrofurantoin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)CN(/N=C\C2=CC=C([N+](=O)[O-])O2)C1=O2604.6Standard non polar33892256
Nitrofurantoin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)CN(/N=C\C2=CC=C([N+](=O)[O-])O2)C1=O3726.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Nitrofurantoin GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dl-5910000000-28fa036f18e5a73e73b82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nitrofurantoin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nitrofurantoin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitrofurantoin 10V, Positive-QTOFsplash10-000i-0190000000-2f95bb616fd4cad3f7292016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitrofurantoin 20V, Positive-QTOFsplash10-000i-0390000000-c768fb1045d9566a1d4b2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitrofurantoin 40V, Positive-QTOFsplash10-0002-9500000000-c45d8a5e217cd30457412016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitrofurantoin 10V, Negative-QTOFsplash10-000i-1090000000-f108972dd03c2012672f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitrofurantoin 20V, Negative-QTOFsplash10-0006-9000000000-b1f3423dbacafe623fb22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nitrofurantoin 40V, Negative-QTOFsplash10-0006-9000000000-7491a417b52b7d6d99d22016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00698 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00698 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4510228
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNitrofurantoin
METLIN IDNot Available
PubChem Compound5353830
PDB IDNot Available
ChEBI ID1039679
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
This enzyme is required for electron transfer from NADP to cytochrome P450 in microsomes. It can also provide electron transfer to heme oxygenase and cytochrome B5.
Gene Name:
POR
Uniprot ID:
P16435
Molecular weight:
77047.575
References
  1. Wang Y, Gray JP, Mishin V, Heck DE, Laskin DL, Laskin JD: Role of cytochrome P450 reductase in nitrofurantoin-induced redox cycling and cytotoxicity. Free Radic Biol Med. 2008 Mar 15;44(6):1169-79. doi: 10.1016/j.freeradbiomed.2007.12.013. Epub 2007 Dec 23. [PubMed:18206659 ]

Transporters

General function:
Involved in ATP binding
Specific function:
Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from the brain. May be involved in brain-to-blood efflux. Appears to play a major role in the multidrug resistance phenotype of several cancer cell lines. When overexpressed, the transfected cells become resistant to mitoxantrone, daunorubicin and doxorubicin, display diminished intracellular accumulation of daunorubicin, and manifest an ATP- dependent increase in the efflux of rhodamine 123
Gene Name:
ABCG2
Uniprot ID:
Q9UNQ0
Molecular weight:
72313.5
References
  1. Perez M, Real R, Mendoza G, Merino G, Prieto JG, Alvarez AI: Milk secretion of nitrofurantoin, as a specific BCRP/ABCG2 substrate, in assaf sheep: modulation by isoflavones. J Vet Pharmacol Ther. 2009 Oct;32(5):498-502. doi: 10.1111/j.1365-2885.2008.01050.x. [PubMed:19754918 ]