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UC175

Sigma-Aldrich

(S)-(+)-Mephenytoin

≥98% (HPLC), solid, CYP2B6 & CYP2C19 substrate

Synonym(s):

(S)-(+)-5-Ethyl-3-methyl-5-phenyl-2,4-imidazolidinedione, (S)-(+)-5-Ethyl-3-methyl-5-phenylhydantoin

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About This Item

Empirical Formula (Hill Notation):
C12H14N2O2
CAS Number:
70989-04-7
Molecular Weight:
218.25
MDL number:
MFCD00270025
UNSPSC Code:
12161501
PubChem Substance ID:
24724646
NACRES:
NA.77

product name

(S)-(+)-Mephenytoin, solid, ≥98% (HPLC)

Quality Level

200

assay

≥98% (HPLC)

form

solid

color

off-white

mp

135-138 °C

solubility

DMSO: soluble

storage temp.

2-8°C

SMILES string

CC[C@]1(NC(=O)N(C)C1=O)c2ccccc2

InChI

1S/C12H14N2O2/c1-3-12(9-7-5-4-6-8-9)10(15)14(2)11(16)13-12/h4-8H,3H2,1-2H3,(H,13,16)/t12-/m0/s1

InChI key

GMHKMTDVRCWUDX-LBPRGKRZSA-N

Application

S-Mephenytoin has been used as a CYP2C19 substrate for the analysis of cytochrome P450 metabolism. S-Mephenytoin has also been used as probe substrates for LC/MS-based analysis of relative activity factor (RAF).

Biochem/physiol Actions

CYP2B6 & CYP2C19 substrate. Methenytoin isomer. Anticonvulsant; antiepileptic.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Preparation Note

(S)-(+)-Mephenytoin is soluble in DMSO.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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Brandon S Pybus et al.
Malaria journal, 11, 259-259 (2012-08-04)
The 8-aminoquinoline (8AQ) drug primaquine (PQ) is currently the only approved drug effective against the persistent liver stage of the hypnozoite forming strains Plasmodium vivax and Plasmodium ovale as well as Stage V gametocytes of Plasmodium falciparum. To date, several
Bent H Hellum et al.
Basic & clinical pharmacology & toxicology, 105(1), 58-63 (2009-04-18)
The aim of this study was to evaluate in vitro the dose-dependent induction potential of six commonly used trade herbal products on CYP2C19 and CYP2E1 metabolic activities in cultured human hepatocytes. S-mephenytoin and chlorzoxazone were used as specific CYP substrates
Stefan J Dekker et al.
British journal of pharmacology, 176(3), 466-477 (2018-11-18)
The aim of this study was to characterize the human cytochrome P450s (CYPs) involved in oxidative bioactivation of flucloxacillin to 5-hydroxymethyl flucloxacillin, a metabolite with high cytotoxicity towards biliary epithelial cells. The CYPs involved in hydroxylation of flucloxacillin were characterized

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