| Identification | Back Directory | [Name]
(S)-MEPHENYTOIN | [CAS]
70989-04-7 | [Synonyms]
Mephenitoin S
(S)-MEPHENYTOIN
(S)-Mephenytoine
(S)-(+)-MEPHENYTOIN
(S)-5-ETHYL-3-METHYL-5-PHENYLHYDANTOIN
(5S)-5-Ethyl-3-methyl-5-phenylhydantoin
(5S)-5β-Ethyl-3-methyl-5-phenylhydantoin
(S)-(+)-5-ETHYL-3-METHYL-5-PHENYLHYDANTOIN
(S)-5-ethyl-3-Methyl-5-phenyliMidazolidine-2,4-dione
(5S)-5-ethyl-3-methyl-5-phenylimidazolidine-2,4-dione
(5S)-5-Ethyl-3-Methyl-5-phenyl-2,4-iMidazolidinedione
(5S)-5-ethyl-3-methyl-5-phenyl-imidazolidine-2,4-dione
(S)-(+)-5-ETHYL-3-METHYL-5-PHENYL-2,4-IMIDAZOLIDINEDIONE
2,4-IMidazolidinedione, 5-ethyl-3-Methyl-5-phenyl-, (5S)-
(S)-(+)-5-Ethyl-3-methyl-5-phenyl-2,4-imidazolidinedione, (S)-(+)-5-Ethyl-3-methyl-5-phenylhydantoin | [Molecular Formula]
C12H14N2O2 | [MDL Number]
MFCD00270025 | [MOL File]
70989-04-7.mol | [Molecular Weight]
218.25 |
| Chemical Properties | Back Directory | [Appearance]
White Crystalline Solid | [Melting point ]
135-138 °C
| [density ]
1.154±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C
| [solubility ]
DMSO: soluble | [form ]
solid
| [pka]
8.07±0.70(Predicted) | [color ]
off-white
|
| Hazard Information | Back Directory | [Chemical Properties]
White Crystalline Solid | [Uses]
Used as an anticonvulsant agent | [Definition]
ChEBI: (S)-Mephenytoin is an imidazolidine-2,4-dione. | [Biological Activity]
(s)-mephenytoin is an anticonvulsive drug which is metabolized by n-demethylation and 4-hydroxylation (of the aromatic ring). (s)-mephenytoin is a substrate of the cytochrome p450 (cyp) isoform cyp2c19, also known as mephenytoin 4-hydroxylase [1].cyp2c19 is the main mephenytoin 4-hydroxylase in humans implicated in metabolizing a variety of therapeutic agents, such as omeprazole, proguanil, diazepam, propranolol, citalopram, imipramine, and certain barbiturates [2]. | [Biochem/physiol Actions]
CYP2B6 & CYP2C19 substrate. Methenytoin isomer. Anticonvulsant; antiepileptic. | [in vitro]
in the presence of cytochrome b5, the km value for s-mephenytoin was 1.25 mm with all five purified cytochrome p-450s preparations, and vmax values were 0.8-1.25 nmol of 4-hydroxy product formed per min/nmol of p-450 [1]. | [References]
[1] shimada t, misono k s, guengerich f p. human liver microsomal cytochrome p-450 mephenytoin 4-hydroxylase, a prototype of genetic polymorphism in oxidative drug metabolism. purification and characterization of two similar forms involved in the reaction[j]. journal of biological chemistry, 1986, 261(2): 909-921.
[2] ferguson r j, de morais s m f, benhamou s, et al. a new genetic defect in human cyp2c19: mutation of the initiation codon is responsible for poor metabolism of s-mephenytoin[j]. journal of pharmacology and experimental therapeutics, 1998, 284(1): 356-361. |
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