(S)-MEPHENYTOIN Chemical Properties

Melting point:

135-138 °C

Density 

1.154±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

DMSO: soluble

pka

8.07±0.70(Predicted)

form 

solid

color 

off-white

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-36

WGK Germany 

2

HS Code 

29332100

MSDS

• Language:English Provider:SigmaAldrich

(S)-MEPHENYTOIN Usage And Synthesis

Chemical Properties

White Crystalline Solid

Uses

S-Mephenytoin has been used as a CYP2C19 substrate for the analysis of cytochrome P450 metabolism. S-Mephenytoin has also been used as probe substrates for LC/MS-based analysis of relative activity factor (RAF).

Uses

(S)-Mephenytoin can be used as an anticonvulsant agent.

Definition

ChEBI: (S)-Mephenytoin is an imidazolidine-2,4-dione.

Biological Activity

(s)-mephenytoin is an anticonvulsive drug which is metabolized by n-demethylation and 4-hydroxylation (of the aromatic ring). (s)-mephenytoin is a substrate of the cytochrome p450 (cyp) isoform cyp2c19, also known as mephenytoin 4-hydroxylase [1].cyp2c19 is the main mephenytoin 4-hydroxylase in humans implicated in metabolizing a variety of therapeutic agents, such as omeprazole, proguanil, diazepam, propranolol, citalopram, imipramine, and certain barbiturates [2].

Biochem/physiol Actions

CYP2B6 & CYP2C19 substrate. Methenytoin isomer. Anticonvulsant; antiepileptic.

in vitro

in the presence of cytochrome b5, the km value for s-mephenytoin was 1.25 mm with all five purified cytochrome p-450s preparations, and vmax values were 0.8-1.25 nmol of 4-hydroxy product formed per min/nmol of p-450 [1].

References

[1] shimada t, misono k s, guengerich f p. human liver microsomal cytochrome p-450 mephenytoin 4-hydroxylase, a prototype of genetic polymorphism in oxidative drug metabolism. purification and characterization of two similar forms involved in the reaction[j]. journal of biological chemistry, 1986, 261(2): 909-921.
[2] ferguson r j, de morais s m f, benhamou s, et al. a new genetic defect in human cyp2c19: mutation of the initiation codon is responsible for poor metabolism of s-mephenytoin[j]. journal of pharmacology and experimental therapeutics, 1998, 284(1): 356-361.

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