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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:06 UTC
HMDB IDHMDB0014673
Secondary Accession Numbers
  • HMDB14673
Metabolite Identification
Common NameMephenytoin
DescriptionMephenytoin, also known as methylphenetoin or mesantoin, belongs to the class of organic compounds known as phenylhydantoins. These are heterocyclic aromatic compounds containing an imiazolidinedione moiety substituted by a phenyl group. Mephenytoin is a drug which is used for the treatment of refractory partial epilepsy. Mephenytoin is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, mephenytoin is involved in ibuprofen action pathway. Mephenytoin is a potentially toxic compound. Mephenytoin is a solid. As such, these agents should not be used concurrently. Mephenytoin is an antiepileptic drug which can be useful in the treatment of epilepsy. Mephenytoin reduces the maximal activity of brain stem centers responsible for the tonic phase of tonic-clonic (grand mal) seizures. Mephenytoin is a hydantoin-derivative anticonvulsant used to control various partial seizures. These are heterocyclic aromatic compounds containing an imiazolidinedione moiety substituted by a phenyl group.
Structure
Data?1582753206
Synonyms
ValueSource
DL-MephenytoinChEBI
MefenitoinaChEBI
MephenytoineChEBI
MephenytoinumChEBI
MethylphenetoinChEBI
PhenylethylmethylhydantoinChEBI
MesantoinKegg
MephentoinHMDB
Methyl hydantoinHMDB
5 Ethyl 3 methyl 5 phenylhydantoinHMDB
5-Ethyl-3-methyl-5-phenylhydantoinHMDB
Phenetoin, methylHMDB
MethoinHMDB
Methyl phenetoinHMDB
PhenantoinHMDB
MefenetoinHMDB
Chemical FormulaC12H14N2O2
Average Molecular Weight218.2518
Monoisotopic Molecular Weight218.105527702
IUPAC Name5-ethyl-3-methyl-5-phenylimidazolidine-2,4-dione
Traditional Namemephenytoin
CAS Registry Number50-12-4
SMILES
CCC1(NC(=O)N(C)C1=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C12H14N2O2/c1-3-12(9-7-5-4-6-8-9)10(15)14(2)11(16)13-12/h4-8H,3H2,1-2H3,(H,13,16)
InChI KeyGMHKMTDVRCWUDX-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
  • 5-phenylhydantoin
  • Phenylimidazolidine
  • Alpha-amino acid or derivatives
  • 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 nitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point135 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.97 g/LNot Available
LogP1.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.97 g/LALOGPS
logP1.64ALOGPS
logP1.67ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)11.18ChemAxon
pKa (Strongest Basic)-8.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.41 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity59.54 m³·mol⁻¹ChemAxon
Polarizability22.67 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f79-2900000000-af8712fc36e2b911e9a8Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f79-2900000000-af8712fc36e2b911e9a8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ue9-1900000000-76ba03e4694ef29def3bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0159-3901000000-d726d8591f6fd6b87a0aSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0159-3901000000-d726d8591f6fd6b87a0aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0490000000-8c8bcd12840df6ae00f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0920000000-360996524b6c1cdc8fe3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-6900000000-5f6a566d2e8972a3e79cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0290000000-de9e2d95bc7cf0aea9acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-7590000000-9cb9accf3f7737fa1483Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-9600000000-a00ec47fefbdc60a200aSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00532 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00532 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00532
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3920
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMephenytoin
METLIN IDNot Available
PubChem Compound4060
PDB IDNot Available
ChEBI ID6757
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available