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Merck

UC126

Sigma-Aldrich

4-Hydroxymephenytoin

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C12H14N2O3
Número de CAS:
Peso molecular:
234.25
MDL number:
UNSPSC Code:
12161501
PubChem Substance ID:
NACRES:
NA.77

form

solid

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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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)
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)
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
Paul D Rainville et al.
Rapid communications in mass spectrometry : RCM, 22(9), 1345-1350 (2008-04-03)
The measurement of cytochrome P450 (CYP450) isoenzyme inhibition is often done during evaluation of new chemical entities in drug discovery. Typical assay protocol consists of multiple CYP450 probe substrates incubated with selected drug candidates and CYP450. Results of the assay
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

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