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UC126

4-Hydroxymephenytoin

Name: 4-Hydroxymephenytoin
Brand: SIGMA

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

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.

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)

A UPLC-MS/MS assay of the "Pittsburgh cocktail": six CYP probe-drug/metabolites from human plasma and urine using stable isotope dilution.

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

Analysis of mephenytoin, 4-hydroxymephenytoin and 4-hydroxyphenytoin enantiomers in human urine by cyclodextrin micellar electrokinetic capillary chromatography: simple determination of a hydroxylation polymorphism in man.

C Desiderio et al.

Electrophoresis, 15(1), 87-93 (1994-01-01)

Using cyclodextrin micellar electrokinetic capillary chromatography (CD-MECC), baseline separation of mephenytoin, 4-hydroxymephenytoin and 4-hydroxyphenytoin enantiomers in urine was effected with beta-cyclodextrin. After single-dose administration of 100 mg of racemic mephenytoin, the 0-8 h urine was collected, and enzymatically hydrolyzed urine

Comparison of (S)-mephenytoin and proguanil oxidation in vitro: contribution of several CYP isoforms.

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

Metabolic disposition of pantoprazole, a proton pump inhibitor, in relation to S-mephenytoin 4'-hydroxylation phenotype and genotype.

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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