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Merck

UC126

4-Hydroxymephenytoin

Cytochrome P450 inhibitor, solid

Synonym(s):

(±)-5-Ethyl-5-(4-hydroxyphenyl)-3-methylhydantoin, (±)-5-Ethyl-5-(4-hydroxyphenyl)-3-methylimididazolidine-2,4-dione

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About This Item

Empirical Formula (Hill Notation):
C12H14N2O3
CAS Number:
61837-65-8
Molecular Weight:
234.25
UNSPSC Code:
12161501
PubChem Substance ID:
24724640
NACRES:
NA.77
MDL number:
MFCD00142316

Key Documents

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Product Name

4-Hydroxymephenytoin,

SMILES string

CCC1(NC(=O)N(C)C1=O)c2ccc(O)cc2

InChI key

OQPLORUDZLXXPD-UHFFFAOYSA-N

InChI

1S/C12H14N2O3/c1-3-12(8-4-6-9(15)7-5-8)10(16)14(2)11(17)13-12/h4-7,15H,3H2,1-2H3,(H,13,17)

form

solid

color

white

mp

153-154 °C

storage temp.

2-8°C

Quality Level

200

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General description

CYP2C19 metabolite of mephenytoin.

Application

4-Hydroxymephenytoin has been used for developing ultra performance LC (UPLC)- tandem mass spectrometry (MS/MS) assays for evaluating cytochrome P450 (CYP) probe drugs and their relevant metabolites in human urine or plasma samples. 4-hydroxymephenytoin has also been used for developing sub-2-micron particle LC/MS/MS-based methods for analyzing CYP450 probe substrate metabolites.

Biochem/physiol Actions

4-Hydroxymephenytoin catabolism displays genetic polymorphism and is a direct indicator of Cytochrome P450 2C19 (CYP2C19) activity. Detection and quantification of 4-hydroxymephenytoin in biological samples by HPLC method is well optimized.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000252424
0000252424
0000210551
0000194514
0000195106

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Simple and selective assay of 4-hydroxymephenytoin in human urine using solid-phase extraction and high-performance liquid chromatography with electrochemical detection and its preliminary application to phenotyping test
Tanaka M, et al.
Journal of Chromatography. B, Biomedical Sciences and Applications, 676(1), 87-94 (1996)
Nicolas A Stewart et al.
The Analyst, 136(3), 605-612 (2010-11-26)
The efficiency of drug metabolism by a single enzyme can be measured as the fractional metabolic clearance which can be used as a measure of whole body activity for that enzyme. Measurement of activity of multiple enzymes simultaneously is feasible
High-performance liquid chromatographic determination of urinary 4?-hydroxymephenytoin, a metabolic marker for the hepatic enzyme CYP2C19, in humans
Xie HG, et al.
Journal of Chromatography. B, Biomedical Sciences and Applications, 668(1), 125-131 (1995)
J K Coller et al.
British journal of clinical pharmacology, 48(2), 158-167 (1999-07-27)
To compare the oxidative metabolism of (S)-mephenytoin and proguanil in vitro and to determine the involvement of various cytochrome P450 isoforms. The kinetics of the formation of 4'-hydroxymephenytoin and cycloguanil in human liver microsomes from 10 liver samples were determined
M Tanaka et al.
Clinical pharmacology and therapeutics, 62(6), 619-628 (1998-01-20)
To assess the possible relationship between the metabolic disposition of pantoprazole and genetically determined S-mephenytoin 4'-hydroxylation phenotype and genotype. The pharmacokinetic disposition of pantoprazole was investigated in 14 Japanese male volunteers (seven extensive and seven poor metabolizers of S-mephenytoin). All
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