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UC126

Sigma-Aldrich

4-Hydroxymephenytoin

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

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 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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