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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:36 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
Disposition

Biological location

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point286 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.071 g/LNot Available
LogP2.2Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available158.381http://allccs.zhulab.cn/database/detail?ID=AllCCS00000953
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+158.47531661259
DarkChem[M-H]-156.59931661259
DeepCCS[M+H]+155.07930932474
DeepCCS[M-H]-152.72130932474
DeepCCS[M-2H]-185.60630932474
DeepCCS[M+Na]+161.17230932474
AllCCS[M+H]+157.632859911
AllCCS[M+H-H2O]+153.532859911
AllCCS[M+NH4]+161.332859911
AllCCS[M+Na]+162.432859911
AllCCS[M-H]-159.532859911
AllCCS[M+Na-2H]-158.832859911
AllCCS[M+HCOO]-158.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PhenytoinO=C1NC(=O)C(N1)(C1=CC=CC=C1)C1=CC=CC=C13545.4Standard polar33892256
PhenytoinO=C1NC(=O)C(N1)(C1=CC=CC=C1)C1=CC=CC=C12415.1Standard non polar33892256
PhenytoinO=C1NC(=O)C(N1)(C1=CC=CC=C1)C1=CC=CC=C12380.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Phenytoin,1TMS,isomer #1C[Si](C)(C)N1C(=O)NC(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O2374.4Semi standard non polar33892256
Phenytoin,1TMS,isomer #1C[Si](C)(C)N1C(=O)NC(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O2298.6Standard non polar33892256
Phenytoin,1TMS,isomer #1C[Si](C)(C)N1C(=O)NC(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O3348.5Standard polar33892256
Phenytoin,1TMS,isomer #2C[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC=CC=C1)C1=CC=CC=C12407.6Semi standard non polar33892256
Phenytoin,1TMS,isomer #2C[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC=CC=C1)C1=CC=CC=C12347.5Standard non polar33892256
Phenytoin,1TMS,isomer #2C[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC=CC=C1)C1=CC=CC=C13555.9Standard polar33892256
Phenytoin,2TMS,isomer #1C[Si](C)(C)N1C(=O)N([Si](C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O2163.8Semi standard non polar33892256
Phenytoin,2TMS,isomer #1C[Si](C)(C)N1C(=O)N([Si](C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O2332.8Standard non polar33892256
Phenytoin,2TMS,isomer #1C[Si](C)(C)N1C(=O)N([Si](C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O2948.4Standard polar33892256
Phenytoin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)NC(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O2684.1Semi standard non polar33892256
Phenytoin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)NC(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O2509.6Standard non polar33892256
Phenytoin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)NC(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O3377.5Standard polar33892256
Phenytoin,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC=CC=C1)C1=CC=CC=C12655.2Semi standard non polar33892256
Phenytoin,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC=CC=C1)C1=CC=CC=C12539.5Standard non polar33892256
Phenytoin,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(=O)NC(=O)C1(C1=CC=CC=C1)C1=CC=CC=C13524.0Standard polar33892256
Phenytoin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O2665.4Semi standard non polar33892256
Phenytoin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O2746.6Standard non polar33892256
Phenytoin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)C(C2=CC=CC=C2)(C2=CC=CC=C2)C1=O3008.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Phenytoin EI-B (Non-derivatized)splash10-003r-7930000000-447969b9c242748dd9432017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Phenytoin CI-B (Non-derivatized)splash10-0udi-0090000000-4176043a7a73caee26672017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Phenytoin EI-B (Non-derivatized)splash10-0zgi-5960000000-e1dcb47a1c082f04f4562017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Phenytoin CI-B (Non-derivatized)splash10-0udi-1390000000-22c71a7e4dbf9c7acab52017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Phenytoin CI-B (Non-derivatized)splash10-0udi-2190000000-50174e33af92b04d1a6e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Phenytoin EI-B (Non-derivatized)splash10-003r-7930000000-447969b9c242748dd9432018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Phenytoin CI-B (Non-derivatized)splash10-0udi-0090000000-4176043a7a73caee26672018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Phenytoin EI-B (Non-derivatized)splash10-0zgi-5960000000-e1dcb47a1c082f04f4562018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Phenytoin CI-B (Non-derivatized)splash10-0udi-1390000000-22c71a7e4dbf9c7acab52018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Phenytoin CI-B (Non-derivatized)splash10-0udi-2190000000-50174e33af92b04d1a6e2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phenytoin GC-MS (Non-derivatized) - 70eV, Positivesplash10-00lr-0920000000-edf72a4c297e405a26002017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phenytoin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phenytoin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0f89-4940000000-2a0dda513d9f63dc66102014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenytoin LC-ESI-qTof , Positive-QTOFsplash10-001i-0950000000-a80521d4dc3976a29b2c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenytoin LC-ESI-qTof , Positive-QTOFsplash10-0ue9-2900000000-a58471ae75fa7319c03d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenytoin LC-ESI-QFT , negative-QTOFsplash10-0udi-0090000000-aaae845342f345f896952017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenytoin LC-ESI-QFT , negative-QTOFsplash10-0udi-0390000000-f8da1896c569c120faa22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenytoin LC-ESI-QFT , negative-QTOFsplash10-0udi-0920000000-07c872b05aade63c402b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenytoin LC-ESI-QFT , negative-QTOFsplash10-0udi-0900000000-be6790637be99260525e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenytoin LC-ESI-QFT , negative-QTOFsplash10-0udi-0900000000-9a17fa0b243c8282f3ba2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenytoin LC-ESI-QFT , negative-QTOFsplash10-0udi-0900000000-69302626996b2b24c1532017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenytoin LC-ESI-QFT , positive-QTOFsplash10-0fai-0690000000-f9eeceb82d117127f6ea2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenytoin LC-ESI-QFT , positive-QTOFsplash10-001i-0910000000-9edcfc62014a6aa7778f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenytoin LC-ESI-QFT , positive-QTOFsplash10-001i-0900000000-d4dde5db680fb7722a492017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenytoin LC-ESI-QFT , positive-QTOFsplash10-0ue9-0900000000-482874b33812389ae7262017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenytoin LC-ESI-QFT , positive-QTOFsplash10-0udi-0900000000-44f07dc29daf8cdf80c22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenytoin LC-ESI-QFT , positive-QTOFsplash10-0udi-1900000000-1241292d531ed37544c72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenytoin , positive-QTOFsplash10-001i-0950000000-a80521d4dc3976a29b2c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenytoin , positive-QTOFsplash10-0ue9-2900000000-a58471ae75fa7319c03d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenytoin 45V, Negative-QTOFsplash10-0udi-0920000000-97a0af331da9afcf54b82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenytoin 60V, Negative-QTOFsplash10-0udi-0900000000-9918b159c9e50b11016f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Phenytoin 90V, Negative-QTOFsplash10-0udi-0900000000-c2ba734800c5db1b68cf2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenytoin 10V, Positive-QTOFsplash10-0udi-0290000000-168825c4263cc790be0b2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenytoin 20V, Positive-QTOFsplash10-0f89-0950000000-27e345a92f77341146542016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenytoin 40V, Positive-QTOFsplash10-0uyi-1900000000-5828317e8dac2d03e5482016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenytoin 10V, Negative-QTOFsplash10-0udi-0090000000-e1551530faa59a5495152016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenytoin 20V, Negative-QTOFsplash10-0udi-1190000000-354c210fa308dab349f32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenytoin 40V, Negative-QTOFsplash10-0006-9700000000-d5833bfc084997249fe42016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00252 details
UrineExpected but not QuantifiedNot QuantifiedNot 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
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. PharmGKB [Link]