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Merck
CN

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
MDL number:
MFCD00142316
UNSPSC Code:
12161501
PubChem Substance ID:
24724640
NACRES:
NA.77

Key Documents

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Product Name

4-Hydroxymephenytoin,

form

solid

Quality Level

200

color

white

mp

153-154 °C

storage temp.

2-8°C

SMILES string

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

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)

InChI key

OQPLORUDZLXXPD-UHFFFAOYSA-N

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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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000252424
0000252424
0000210551
0000194514
0000195106

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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
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)
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)
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
A Adedoyin et al.
Clinical pharmacology and therapeutics, 64(1), 8-17 (1998-08-08)
Drug metabolism is influenced by liver disease because of the central role that the liver plays in metabolic activities in the body. However, it is still unclear how activities of specific drug-metabolizing enzymes are influenced by the presence and severity
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