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UC177

Sigma-Aldrich

(±)-Mephenytoin

Synonym(s):

(±)-5-Ethyl-3-methyl-5-phenyl-2,4-imidazolidinedione, (±)-5-Ethyl-3-methyl-5-phenylhydantoin

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About This Item

Empirical Formula (Hill Notation):
C12H14N2O2
CAS Number:
50-12-4
Molecular Weight:
218.25
EC Number:
200-012-8
MDL number:
MFCD00022407
UNSPSC Code:
12161501
PubChem Substance ID:
329827653
Pricing and availability is not currently available.

form

crystals

Quality Level

200

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

Gene Information

human ... SCN10A(6336) , SCN11A(11280) , SCN1A(6323) , SCN2A(6326) , SCN3A(6328) , SCN4A(6329) , SCN5A(6331) , SCN7A(6332) , SCN8A(6334) , SCN9A(6335)

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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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
561-020-2V
561-020-2
023M3904V
023M3904
561-20-2V

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Yasuhiro Uno et al.
The Journal of veterinary medical science, 72(2), 225-228 (2009-11-27)
The macaque is widely used for investigation of drug metabolism due to its evolutionary closeness to the human. However, the genetic backgrounds of drug-metabolizing enzymes have not been fully investigated; therefore, identification and characterization of drug-metabolizing enzyme genes are important
Susanne Löfgren et al.
Drug metabolism and disposition: the biological fate of chemicals, 36(5), 955-962 (2008-02-16)
CYP2C19 is an important enzyme for human drug metabolism, and it also participates in the metabolism of endogenous substrates, whereas the CYP2C18 enzyme is not expressed in human liver despite high mRNA expression. Mice transgenic for the human CYP2C18 and
Huijuan Wang et al.
Drug metabolism and disposition: the biological fate of chemicals, 39(5), 830-837 (2011-02-18)
CYP2C19 is a highly polymorphic enzyme that affects the metabolism of a wide range of therapeutic drugs. Almost all the identified alleles of CYP2C19 are derived from nonsynonymous single nucleotide polymorphisms (nsSNPs). The objective of this study was to functionally
Michael Zientek et al.
Journal of pharmacological and toxicological methods, 58(3), 206-214 (2008-07-19)
Inhibition of cytochrome P450 (CYP) is a principal mechanism for metabolism-based drug-drug interactions (DDIs). This article describes a robust, high-throughput CYP-mediated DDI assay using a cocktail of 5 clinically relevant probe substrates with quantification by liquid chromatography/tandem mass spectrometry (LC/MS-MS).
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
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Chromatograms

application for HPLC

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