Startseite>>Lipids>> P450>>(S)-Mephenytoin

(S)-Mephenytoin (Synonyms: (S)-5-Ethyl-3-methyl-5-phenylhydantoin)

Katalog-Nr.GC14486

(S)-Mephenytoin ((+)-Mephenytoin) ist ein Antikonvulsivum.

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(S)-Mephenytoin Chemische Struktur

Cas No.: 70989-04-7

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Sample solution is provided at 25 µL, 10mM.

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Product Documents

Quality Control & SDS

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Background

S-Mephenytoin (5-phenyl-5-ethyl-N-methylhydantoin) is an anticonvulsive drug which is metabolized by N-demethylation and 4-hydroxylation (of the aromatic ring). CYP2C19 genotype is a major determined factor for metabolisms of S-Mephenytoin. The formations of 4X-hydroxymephenytoin, S-Mephenytoin’s metabolite is CYP2C19 genotype dependent.[1][2]

The genetic polymorphism of CYP2C19 was revealed by the discovery of deficient 4’-hydroxylation of mephenytoin (3-methyl-5-phenyl-5 ethylhydantoin; Mesantoin). Human can be characterized as poor (PM) or extensive metabolizers (EM) with use of racemic mephenytoin as a phenotyping drug, and CYP2C19 has been identified as the major S-Mephenytoin (S-MP) hydroxylase in human. This polymorphism affects the metabolism of many other clinically important drugs such as diazepam, omeprazole (OP), imipramine, propranolol, and chloroguanide.[1]

Rabbit anti-human cytochrome b5 inhibited NADH-cytochrome-c reductase and S-Mephenytoin 4-hydroxylase activities in human liver microsomes. 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. P-45OMP is a relatively selective P-450 form that metabolizes substituted hydantoins well.[2]

References:
[1]. Zhou HH. CYP2C19 genotype determines enzyme activity and inducibility of S-Mephenytoin hydroxylase. Clin Chim Acta. 2001 Nov;313(1-2):203-8.
[2]. 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.

Chemical Properties

Cas No. 70989-04-7 SDF
Überlieferungen (S)-5-Ethyl-3-methyl-5-phenylhydantoin
Chemical Name (5S)-5-ethyl-3-methyl-5-phenyl-2,4-imidazolidinedione
Canonical SMILES O=C1[C@@](C2=CC=CC=C2)(CC)NC(N1C)=O
Formula C12H14N2O2 M.Wt 218.3
Löslichkeit 15mg/ml in ethanol;25mg/ml in DMSO;25mg/ml in dimethyl formamide Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table

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1 mg 5 mg 10 mg
1 mM 4.5809 mL 22.9043 mL 45.8085 mL
5 mM 0.9162 mL 4.5809 mL 9.1617 mL
10 mM 0.4581 mL 2.2904 mL 4.5809 mL
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