(S)-Mephenytoin

A substrate of CYP2C19

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1mg

￥525.00

420.00

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5mg

￥1287.00

1030.00

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10mg

￥2312.00

1850.00

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25mg

￥5087.00

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货号: ajci13214
CAS: 70989-04-7
别名: 甲秦皮素,(S)-5-Ethyl-3-methyl-5-phenylhydantoin
分子式: C12H14N2O2
分子量: 218.3
纯度: >98%
溶解度: 15mg/ml in ethanol;25mg/ml in DMSO;25mg/ml in dimethyl formamide
储存: Store at -20°C
库存: 现货

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]

参考文献:
[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.

S-Mephenytoin (5-phenyl-5-ethyl-N-methylhydantoin) 是一种抗惊厥药，通过 N-去甲基化和 4-羟基化（芳环）代谢。 CYP2C19 基因型是 S-美芬妥英代谢的主要决定因素。 S-Mephenytoin 的代谢物 4X-hydroxymephenytoin 的形成依赖于 CYP2C19 基因型。^[1][2]

美苯妥英（3-甲基-5-苯基-5 乙基乙内酰脲；美山妥英）的 4'-羟基化缺陷的发现揭示了 CYP2C19 的遗传多态性。使用外消旋美苯妥英作为表型药物，人类可被表征为弱代谢者 (PM) 或强代谢者 (EM)，并且 CYP2C19 已被确定为人类中主要的 S-美芬妥英 (S-MP) 羟化酶。这种多态性影响许多其他临床重要药物的代谢，例如地西泮、奥美拉唑 (OP)、丙咪嗪、普萘洛尔和氯胍。^[1]

兔抗人细胞色素 b5 抑制人肝微粒体中的 NADH-细胞色素-c 还原酶和 S-美芬妥英 4-羟化酶活性。在细胞色素 b5 存在的情况下，所有五种纯化的细胞色素 P-450 制剂的 S-美芬妥英的 Km 值为 1.25 mM，Vmax 值为每分钟/nmol P-450 形成的 4-羟基产物 0.8-1.25 nmol。 P-45OMP 是一种相对选择性的 P-450 形式，可以很好地代谢取代的乙内酰脲。^[2]