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UC177

Sigma-Aldrich

(±)-Mephenytoin

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Synonym(s):
(±)-5-Ethyl-3-methyl-5-phenyl-2,4-imidazolidinedione, (±)-5-Ethyl-3-methyl-5-phenylhydantoin
Empirical Formula (Hill Notation):
C12H14N2O2
CAS Number:
Molecular Weight:
218.25
EC Number:
MDL number:
PubChem Substance ID:

form

crystals

color

off-white

mp

115-118 °C
135-137 °C

solubility

DMSO: soluble

storage temp.

2-8°C

SMILES string

CCC1(NC(=O)N(C)C1=O)c2ccccc2

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

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Biochem/physiol Actions

CYP2B6 and CYP2C19 substrate; anticonvulsive, antiepileptic.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Preparation Note

(±)-Mephenytoin is soluble in DMSO.

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Robert S Foti et al.
Drug metabolism and disposition: the biological fate of chemicals, 36(3), 523-528 (2007-12-01)
Understanding the potential for cytochrome P450 (P450)-mediated drug-drug interactions is a critical part of the drug discovery process. Factors such as nonspecific binding, atypical kinetics, poor effector solubility, and varying ratios of accessory proteins may alter the kinetic behavior of
Doaa A Elsherbiny et al.
Journal of pharmacokinetics and pharmacodynamics, 35(2), 203-217 (2008-03-20)
The study aim was to assess the inductive properties of artemisinin antimalarials using mephenytoin as a probe for CYP2B6 and CYP2C19 enzymatic activity. The population pharmacokinetics of S-mephenytoin and its metabolites S-nirvanol and S-4'-hydroxymephenytoin, including enzyme turn-over models for induction
Annalise Di Marco et al.
Drug metabolism and disposition: the biological fate of chemicals, 35(10), 1737-1743 (2007-06-30)
A rapid and sensitive radiometric assay for assessing the potential of drugs to inhibit cytochrome P450 (P450) 2C19 in human liver microsomes is described. The new assay, which does not require high-performance liquid chromatography (HPLC) separation or mass spectrometric detection
Robert S Foti et al.
Journal of medicinal chemistry, 55(3), 1205-1214 (2012-01-14)
A series of omeprazole-based analogues was synthesized and assessed for inhibitory activity against CYP2C19. The data was used to build a CYP2C19 inhibition pharmacophore model for the series. The model was employed to design additional analogues with inhibitory potency against
Yajing Hu et al.
Pharmacogenetics and genomics, 23(2), 78-83 (2012-12-18)
We investigated whether human pharmacogenetic factors could be characterized using chimeric NOG mice expressing a thymidine kinase transgene (TK-NOG) with 'humanized' livers. The rate of human-specific metabolism of two drugs was measured in chimeric mice reconstituted with human hepatocytes with

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