(S)-Mephenytoin

Names

[ Name ]:
(S)-Mephenytoin

[Synonym ]:
S(+)-5-Ethyl-3-methyl-5-phenylhydantoin
S(+)-5-Ethyl-1-methyl-5-phenylbarbituric acid
S-mephenytoin
(+)-Mephobarbitol
5-ethyl-3-methyl-5-phenylimidazolidine-2,4-dione
5-éthyl-3-méthyl-5-phénylimidazolidine-2,4-dione
5-Ethyl-3-methyl-5-phenyl-2,4-imidazolidinedione
(S)-Mephenytoin
mephenytoin
(5S)-5-Ethyl-3-methyl-5-phenyl-2,4-imidazolidinedione
[14C]-(+)-Mephenytoin
UNII:R420KW629U
5-Ethyl-3-methyl-5-phenylimidazolidin-2,4-dion
2,4,6(1H,3H,5H)-Pyrimidinetrione,5-ethyl-1-methyl-5-phenyl-,(S)
(+)-Mephobarbital
Gerot-Epilan
(5R)-mephobarbital
(S)-5-Ethyl-1-methyl-5-phenyl-2,4,6(1H,3H,5H)-pyrimidinetrione
2,4-Imidazolidinedione, 5-ethyl-3-methyl-5-phenyl-
(S)-Methylphenobarbital
UNII-5NC67NU76B component ALARQZQTBTVLJV-ZDUSSCGKSA-N
2,4-Imidazolidinedione, 5-ethyl-3-methyl-5-phenyl-, (5S)-

Biological Activity

[Description]:

(S)-Mephenytoin ((+)-Mephenytoin) is an anticonvulsive agent. (S)-Mephenytoin is a substrate of the cytochrome P450 (CYP) isoform CYP2C19. (S)-Mephenytoin can be used for the analysis of cytochrome P450 metabolism[1][2].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Neurological Disease

[In Vitro]

In the presence of cytochrome b5, the Km for S-mephenytoin is 1.25 mM with all five purified cytochrome P-450s preparations[1].

[References]

[1]. Shimada T, et, al. 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 Biol Chem. 1986 Jan 15;261(2):909-21.

[2]. Goldstein JA, et, al. Evidence that CYP2C19 is the major (S)-mephenytoin 4'-hydroxylase in humans. Biochemistry. 1994 Feb 22;33(7):1743-52.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Melting Point ]:
135-138ºC

[ Molecular Formula ]:
C₁₂H₁₄N₂O₂

[ Molecular Weight ]:
218.252

[ Exact Mass ]:
218.105530

[ PSA ]:
49.41000

[ LogP ]:
1.40

[ Index of Refraction ]:
1.541

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
22-36/37/38

[ Safety Phrases ]:
26-36

[ RIDADR ]:
NONH for all modes of transport

Precursor & DownStream

Precursor

DownStream

Articles

CYP450 phenotyping and accurate mass identification of metabolites of the 8-aminoquinoline, anti-malarial drug primaquine.

Malaria Journal 11 , 259, (2012)

The 8-aminoquinoline (8AQ) drug primaquine (PQ) is currently the only approved drug effective against the persistent liver stage of the hypnozoite forming strains Plasmodium vivax and Plasmodium ovale...

Trade herbal products and induction of CYP2C19 and CYP2E1 in cultured human hepatocytes.

Basic Clin Pharmacol Toxicol. 105(1) , 58-63, (2009)

The aim of this study was to evaluate in vitro the dose-dependent induction potential of six commonly used trade herbal products on CYP2C19 and CYP2E1 metabolic activities in cultured human hepatocyte...