Mephenytoin (CED0006470)

Record Information
Version1.0
Creation Date2016-05-25 18:21:05 UTC
Update Date2026-08-18 17:43:55 UTC
Accession NumberCHEM022130
Identification
Common NameMephenytoin
ClassSmall Molecule
Description
Mephenytoin is an organic compound with the chemical formula C12H14N2O2 and an average molecular weight of 218.25 g/mol. Mephenytoin belongs to the imidazolidines, a subclass of azolidines within the organic compounds. It is categorized under the superclass of organoheterocyclic compounds. The compound is found in or released from seven recorded sources. These include healthcare, pharmaceuticals and veterinary products, specifically as antiepileptics, as well as electrical and electronic equipment such as television systems and electrically stimulated smoking devices. Additionally, it is associated with household cleaning and consumer products, including tobacco smoke filters and perfumes within soaps and detergents, and food, food processing and cookware, specifically in processing meats and food preservation. The recorded exposure route for this substance is oral. In terms of biological activity, mephenytoin is associated with two recorded protein targets. It acts as an activator or inhibitor of the sodium channel protein type 5 subunit alpha (SCN5A) and interacts with the nuclear receptor subfamily 1 group I member 2 (NR1I2).
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
DL-MephenytoinChEBI
MefenitoinaChEBI
MephenytoineChEBI
MephenytoinumChEBI
MethylphenetoinChEBI
PhenylethylmethylhydantoinChEBI
MesantoinKegg
MephentoinHMDB
Methyl hydantoinHMDB
5 Ethyl 3 methyl 5 phenylhydantoinMeSH, HMDB
5-Ethyl-3-methyl-5-phenylhydantoinMeSH, HMDB
Phenetoin, methylMeSH, HMDB
MethoinMeSH, HMDB
Methyl phenetoinMeSH, HMDB
PhenantoinMeSH, HMDB
MefenetoinMeSH, HMDB
Chemical FormulaC12H14N2O2
Average Molecular Mass218.252 g/mol
Monoisotopic Mass218.106 g/mol
CAS Registry Number50-12-4
IUPAC Name5-ethyl-3-methyl-5-phenylimidazolidine-2,4-dione
Traditional Namemephenytoin
SMILESCCC1(NC(=O)N(C)C1=O)C1=CC=CC=C1
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-0f79-2900000000-af8712fc36e2b911e9a8Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0f79-2900000000-af8712fc36e2b911e9a8Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0ue9-1900000000-76ba03e4694ef29def3bNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0159-3901000000-d726d8591f6fd6b87a0aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0159-3901000000-d726d8591f6fd6b87a0aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0490000000-8c8bcd12840df6ae00f2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0920000000-360996524b6c1cdc8fe3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ue9-6900000000-5f6a566d2e8972a3e79cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0290000000-de9e2d95bc7cf0aea9acNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-7590000000-9cb9accf3f7737fa1483Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000x-9600000000-a00ec47fefbdc60a200aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0190000000-8b9cb11606c241146d8bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00lr-1900000000-a867b49304e4c2814177Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-6900000000-2fd710ba16d058127ae9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0090000000-4f94e1f66d72d6972b8aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-2900000000-be298ddea23898cbfbc6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01ox-6900000000-8676a25532452b4ac29bNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
925.0Log mg/kg[520:1600]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
371AntiepilepticsHealthcare, pharmaceuticals & veterinary productsNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Beta-secretase 1 structureClick to view 3D structureBeta-secretase 1P56817HumansPredicted (SEA)151.417
Click to view 3D structurePalmitoyl-protein thioesterase ABHD10, mitochondrialQ6PE15Mus musculusPredicted (SEA)0.155698
Click to view 3D structureSodium-dependent serotonin transporterP31652Rattus norvegicusPredicted (SEA)321.984
5-hydroxytryptamine receptor 1A structureClick to view 3D structure5-hydroxytryptamine receptor 1AP08908HumansPredicted (SEA)972.882
5-hydroxytryptamine receptor 7 structureClick to view 3D structure5-hydroxytryptamine receptor 7P34969HumansPredicted (SEA)732.717
5-hydroxytryptamine receptor 6 structureClick to view 3D structure5-hydroxytryptamine receptor 6P50406HumansPredicted (SEA)785.499
Mu-type opioid receptor structureClick to view 3D structureMu-type opioid receptorP35372HumansPredicted (SEA)1235.78
Beta-secretase 2 structureClick to view 3D structureBeta-secretase 2Q9Y5Z0HumansPredicted (SEA)73.8011
Adenosine receptor A2b structureClick to view 3D structureAdenosine receptor A2bP29275HumansPredicted (SEA)430.195
Click to view 3D structureAlpha-1D adrenergic receptorP23944Rattus norvegicusPredicted (SEA)245.381
Plasmepsin II structureClick to view 3D structurePlasmepsin IIP46925Plasmodium falciparumPredicted (SEA)71.232
Click to view 3D structureAdenosine receptor A1P25099Rattus norvegicusPredicted (SEA)419.763
Click to view 3D structureSodium-dependent dopamine transporterP23977Rattus norvegicusPredicted (SEA)522.446
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)4324.13
Click to view 3D structureAlpha-1A adrenergic receptorP43140Rattus norvegicusPredicted (SEA)659.694
Click to view 3D structureAdenosine receptor A2aP30543Rattus norvegicusPredicted (SEA)432.141
72 kDa type IV collagenase structureClick to view 3D structure72 kDa type IV collagenaseP08253HumansPredicted (SEA)1426.43
D(2) dopamine receptor structureClick to view 3D structureD(2) dopamine receptorP14416HumansPredicted (SEA)2711.49
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)1839.03
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)2753.53
Click to view 3D structureAdenosine receptor A1P28190Bos taurusPredicted (SEA)183.101
Muscarinic acetylcholine receptor M2 structureClick to view 3D structureMuscarinic acetylcholine receptor M2P08172HumansPredicted (SEA)1534.25
Cathepsin D structureClick to view 3D structureCathepsin DP07339HumansPredicted (SEA)392.827
Glycogen synthase kinase-3 beta structureClick to view 3D structureGlycogen synthase kinase-3 betaP49841HumansPredicted (SEA)3911.3
Click to view 3D structure1-deoxy-D-xylulose-5-phosphate synthase, chloroplasticQ38854Arabidopsis thalianaPredicted (SEA)12.8451
Concentrations
Not Available
External Links
DrugBank IDDB00532
HMDB IDHMDB0257078
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMephenytoin
Chemspider ID3920
ChEBI ID6757
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11422005
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15282764
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=25797720
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=29438107