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(R)-Mephenytoin

(Synonyms: 美芬妥英,(–)-Mephenytoin) 目录号 : GC18286

An enantiomer of mephenytoin

(R)-Mephenytoin Chemical Structure

Cas No.:71140-51-7

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1mg
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10mg
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25mg
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产品描述

(R)-Mephenytoin is the (R) enantiomer of the anticonvulsant mephenytoin.[1] (R)-Mephenytoin can be demethylated by the cytochrome P450 (CYP) isoform CYP2C9 to form the active metabolite 5-ethyl-5-phenylhydantoin (nirvanol). [2][3]The ratio of (S)-mephenytoin to (R)-mephenytoin in urine following administration of the racemic mixture has been used to detect polymorphisms in drug metabolism by CYP2C19, as only (S)-mephenytoin is a substrate of CYP2C19.[4][5][2]

Reference:
[1]. Meier, U.T., Kronbach, T., and Meyer, U.A. Assay of mephenytoin metabolism in human liver microsomes by high-performance liquid chromatography. Anal. Biochem. 151(2), 286-291 (1985).
[2]. Lewis, D.F., Dickins, M., Weaver, R.J., et al. Molecular modelling of human CYP2C subfamily enzymes CYP2C9 and CYP2C19: Rationalization of substrate specificity and site-directed mutagenesis experiments in the CYP2C subfamily. Xenobiotica. 28(3), 235-268 (1998).
[3]. Wong, P.T.H., Tan, S.F., and Lee, H.S. N-demethylation of methyl and dimethyl derivatives of phenytoin and their anticonvulsant activities in mice. Japanese Journal of Pharmacology 48(4), 473-478 (1988).
[4]. Ferguson, R.J., de Morais, S.M., Benhamou, S., et al. A new genetic defect in human CYP2C19: Mutation of the initiation codon is responsible for poor metabolism of S-mephenytoin. Journal of Pharmacology and Experimental Therapeutics 284(1), 356-361 (1998).
[5]. Guttendorf, R.J., Britto, M., Blouin, R.A., et al. Rapid screening for polymorphisms in dextromethorphan and mephenytoin metabolism. British Journal of Clinical Pharmacology 29(4), 373-380 (1990).

Chemical Properties

Cas No. 71140-51-7 SDF
别名 美芬妥英,(–)-Mephenytoin
化学名 (5R)-5-ethyl-3-methyl-5-phenyl-2,4-imidazolidinedione
Canonical SMILES O=C1[C@@](CC)(C2=CC=CC=C2)NC(N1C)=O
分子式 C12H14N2O2 分子量 218.3
溶解度 15mg/mL in ethanol, 25mg/mL in DMSO, or in DMF 储存条件 Store at -20°C
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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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