ContaminantDB: Mephenytoin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 18:21:05 UTC

Update Date

2016-11-09 01:17:26 UTC

Accession Number

CHEM022130

Identification

Common Name

Mephenytoin

Class

Small Molecule

Description

An imidazolidine-2,4-dione (hydantoin) in which the imidazolidine nucleus carries a methyl group at N-3 and has ethyl and phenyl substituents at C-5. An anticonvulsant, it is no longer available in the USA or the UK but is still studied largely because of its interesting hydroxylation polymorphism.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
DL-Mephenytoin	ChEBI
Mefenitoina	ChEBI
Mephenytoine	ChEBI
Mephenytoinum	ChEBI
Methylphenetoin	ChEBI
Phenylethylmethylhydantoin	ChEBI
Mesantoin	Kegg
Mephentoin	HMDB
Methyl hydantoin	HMDB
5 Ethyl 3 methyl 5 phenylhydantoin	MeSH, HMDB
5-Ethyl-3-methyl-5-phenylhydantoin	MeSH, HMDB
Phenetoin, methyl	MeSH, HMDB
Methoin	MeSH, HMDB
Methyl phenetoin	MeSH, HMDB
Phenantoin	MeSH, HMDB
Mefenetoin	MeSH, HMDB

Chemical Formula

C₁₂H₁₄N₂O₂

Average Molecular Mass

218.252 g/mol

Monoisotopic Mass

218.106 g/mol

CAS Registry Number

50-12-4

IUPAC Name

5-ethyl-3-methyl-5-phenylimidazolidine-2,4-dione

Traditional Name

mephenytoin

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 Key

GMHKMTDVRCWUDX-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azolidines

Sub Class

Imidazolidines

Direct Parent

Phenylhydantoins

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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.97 g/L	ALOGPS
logP	1.64	ALOGPS
logP	1.67	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	11.18	ChemAxon
pKa (Strongest Basic)	-8.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.41 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	59.54 m³·mol⁻¹	ChemAxon
Polarizability	22.67 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0f79-2900000000-af8712fc36e2b911e9a8	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0f79-2900000000-af8712fc36e2b911e9a8	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ue9-1900000000-76ba03e4694ef29def3b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0159-3901000000-d726d8591f6fd6b87a0a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0159-3901000000-d726d8591f6fd6b87a0a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0490000000-8c8bcd12840df6ae00f2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0920000000-360996524b6c1cdc8fe3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ue9-6900000000-5f6a566d2e8972a3e79c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0290000000-de9e2d95bc7cf0aea9ac	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-7590000000-9cb9accf3f7737fa1483	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000x-9600000000-a00ec47fefbdc60a200a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0190000000-8b9cb11606c241146d8b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00lr-1900000000-a867b49304e4c2814177	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-6900000000-2fd710ba16d058127ae9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0090000000-4f94e1f66d72d6972b8a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-2900000000-be298ddea23898cbfbc6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01ox-6900000000-8676a25532452b4ac29b	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00532

HMDB ID

HMDB0257078

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Mephenytoin

Chemspider ID

3920

ChEBI ID

6757

PubChem Compound ID

Not Available

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not 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

Mephenytoin (CHEM022130)

Structure for CHEM022130: Mephenytoin