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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:39:35 UTC
HMDB IDHMDB0014397
Secondary Accession Numbers
  • HMDB14397
Metabolite Identification
Common NamePhenytoin
DescriptionAn anticonvulsant that is used in a wide variety of seizures. It is also an anti-arrhythmic and a muscle relaxant. The mechanism of therapeutic action is not clear, although several cellular actions have been described including effects on ion channels, active transport, and general membrane stabilization. The mechanism of its muscle relaxant effect appears to involve a reduction in the sensitivity of muscle spindles to stretch. Phenytoin has been proposed for several other therapeutic uses, but its use has been limited by its many adverse effects and interactions with other drugs. [PubChem]
Structure
Data?1582753175
Synonyms
ValueSource
5,5-Diphenyl-imidazolidine-2,4-dioneChEBI
5,5-Diphenylimidazolidine-2,4-dioneChEBI
5,5-Diphenyltetrahydro-1H-2,4-imidazoledioneChEBI
DILANTINChEBI
FenitoinaChEBI
PHENTYTOINChEBI
PhenytoineChEBI
PhenytoinumChEBI
5,5-DiphenylhydantoinHMDB
5,5-DwufenylohydantoinaHMDB
DihydantoinHMDB
Diphenylan sodiumHMDB
DiphenylhydantoinHMDB
DiphenylhydatanoinHMDB
Phenytoin sodiumHMDB
DifeninHMDB
Diphenylhydantoinate, sodiumHMDB
Park davis brand OF phenytoinHMDB
Pfizer brand OF phenytoinHMDB
Sodium diphenylhydantoinateHMDB
DihydanHMDB
EpaminHMDB
Phenytoin pfizer brandHMDB
AntisacerHMDB
EpanutinHMDB
HydantolHMDB
Phenytoin phizer brandHMDB
FenitoinHMDB
Phizer brand OF phenytoinHMDB
Chemical FormulaC15H12N2O2
Average Molecular Weight252.268
Monoisotopic Molecular Weight252.089877638
IUPAC Name5,5-diphenylimidazolidine-2,4-dione
Traditional Namesilantin
CAS Registry Number57-41-0
SMILES
O=C1NC(=O)C(N1)(C1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C15H12N2O2/c18-13-15(17-14(19)16-13,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H,(H2,16,17,18,19)
InChI KeyCXOFVDLJLONNDW-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylhydantoins. These are heterocyclic aromatic compounds containing an imiazolidinedione moiety substituted by a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzolidines
Sub ClassImidazolidines
Direct ParentPhenylhydantoins
Alternative Parents
Substituents
  • Diphenylmethane
  • 5-phenylhydantoin
  • Phenylimidazolidine
  • Alpha-amino acid or derivatives
  • 5-monosubstituted hydantoin
  • N-acyl urea
  • Ureide
  • Monocyclic benzene moiety
  • Benzenoid
  • Dicarboximide
  • Urea
  • Carbonic acid derivative
  • Carboxylic acid derivative
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Process

Naturally occurring process:

Role

Indirect biological role:

Environmental role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point286 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.071 g/LNot Available
LogP2.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.071 g/LALOGPS
logP2.26ALOGPS
logP2.15ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)8.49ChemAxon
pKa (Strongest Basic)-9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.2 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity70.18 m³·mol⁻¹ChemAxon
Polarizability25.48 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-003r-7930000000-447969b9c242748dd943Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0udi-0090000000-4176043a7a73caee2667Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0zgi-5960000000-e1dcb47a1c082f04f456Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0udi-1390000000-22c71a7e4dbf9c7acab5Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0udi-2190000000-50174e33af92b04d1a6eSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-003r-7930000000-447969b9c242748dd943Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0udi-0090000000-4176043a7a73caee2667Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0zgi-5960000000-e1dcb47a1c082f04f456Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0udi-1390000000-22c71a7e4dbf9c7acab5Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0udi-2190000000-50174e33af92b04d1a6eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00lr-0920000000-edf72a4c297e405a2600Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-001i-0950000000-a80521d4dc3976a29b2cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0ue9-2900000000-a58471ae75fa7319c03dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0udi-0090000000-aaae845342f345f89695Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0udi-0390000000-f8da1896c569c120faa2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0udi-0920000000-07c872b05aade63c402bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0udi-0900000000-be6790637be99260525eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0udi-0900000000-9a17fa0b243c8282f3baSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0udi-0900000000-69302626996b2b24c153Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0fai-0690000000-f9eeceb82d117127f6eaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-001i-0910000000-9edcfc62014a6aa7778fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-001i-0900000000-d4dde5db680fb7722a49Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0ue9-0900000000-482874b33812389ae726Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-0900000000-44f07dc29daf8cdf80c2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-1900000000-1241292d531ed37544c7Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-0950000000-a80521d4dc3976a29b2cSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0ue9-2900000000-a58471ae75fa7319c03dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0290000000-168825c4263cc790be0bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-0950000000-27e345a92f7734114654Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uyi-1900000000-5828317e8dac2d03e548Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-e1551530faa59a549515Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1190000000-354c210fa308dab349f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9700000000-d5833bfc084997249fe4Spectrum
MSMass Spectrum (Electron Ionization)splash10-0f89-4940000000-2a0dda513d9f63dc6610Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00252 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00252 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 IDDB00252
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID1710
KEGG Compound IDC07443
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhenytoin
METLIN IDNot Available
PubChem Compound1775
PDB IDNot Available
ChEBI ID8107
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. PharmGKB [Link]