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Record Information
Version3.6
Creation Date2012-09-06 15:16:50 UTC
Update Date2016-02-11 01:29:28 UTC
HMDB IDHMDB14673
Secondary Accession NumbersNone
Metabolite Identification
Common NameMephenytoin
DescriptionMephenytoin is a hydantoin-derivative anticonvulsant used to control various partial seizures. It is generally reserved for treatment of individuals refractory to less toxic agents. Mephenytoin and oxazolidinedione derivatives are associated with higher incidences of blood dyscrasias compared to other anticonvulsants. As such, these agents should not be used concurrently.
Structure
Thumb
Synonyms
ValueSource
MesantoinKegg
MephentoinHMDB
Methyl hydantoinHMDB
MethylphenetoinHMDB
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 KeyInChIKey=GMHKMTDVRCWUDX-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Ureide
  • Benzenoid
  • Monocyclic benzene moiety
  • Urea
  • Tertiary amine
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Anticonvulsants
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point135 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility9.70e-01 g/LNot Available
LogP1.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.97 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity59.54 m3·mol-1ChemAxon
Polarizability22.67 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00532
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00532
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00532
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3920
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMephenytoin
NuGOwiki LinkHMDB14673
Metagene LinkHMDB14673
METLIN IDNot Available
PubChem Compound4060
PDB IDNot Available
ChEBI ID166016
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available