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UC175

Sigma-Aldrich

(S)-(+)-Mephenytoin

solid, ≥98% (HPLC)

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Synonym(s):
(S)-(+)-5-Ethyl-3-methyl-5-phenyl-2,4-imidazolidinedione, (S)-(+)-5-Ethyl-3-methyl-5-phenylhydantoin
Empirical Formula (Hill Notation):
C12H14N2O2
CAS Number:
Molecular Weight:
218.25
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

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This Item
UC126UC180SML0248
(S)-(+)-Mephenytoin solid, ≥98% (HPLC)

UC175

(S)-(+)-Mephenytoin

4-Hydroxymephenytoin

UC126

4-Hydroxymephenytoin

(S)-(+)-Nirvanol

UC180

(S)-(+)-Nirvanol

Zolmitriptan ≥98% (HPLC)

SML0248

Zolmitriptan

form

solid

form

solid

form

solid

form

powder

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

solubility

DMSO: soluble

solubility

-

solubility

DMF: soluble

solubility

DMSO: ≥5 mg/mL

color

off-white

color

white

color

off-white

color

white to beige

mp

135-138 °C

mp

153-154 °C

mp

-

mp

-

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

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


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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
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

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