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(S)-MEPHENYTOIN

CAS No.
70989-04-7
Chemical Name:
(S)-MEPHENYTOIN
Synonyms
Mephenitoin S;(S)-MEPHENYTOIN;(S)-Mephenitoin;(S)-Mephenytoine;(S)-(+)-MEPHENYTOIN;Mephenytoin Impurity 2;(S)-5-ETHYL-3-METHYL-5-PHENYLHYDANTOIN;(5S)-5-Ethyl-3-methyl-5-phenylhydantoin;(S)-(+)-Mephenytoin solid, >=98% (HPLC);(5S)-5β-Ethyl-3-methyl-5-phenylhydantoin
CBNumber:
CB7257425
Molecular Formula:
C12H14N2O2
Molecular Weight:
218.25
MDL Number:
MFCD00270025
MOL File:
70989-04-7.mol
MSDS File:
SDS
Last updated:2023-09-04 15:51:00

(S)-MEPHENYTOIN Properties

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
FDA UNII D9818430MW

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P261-P264-P270-P301+P312-P302+P352-P305+P351+P338
Hazard Codes  Xn
Risk Statements  22-36/37/38
Safety Statements  26-36
WGK Germany  2
HS Code  29332100
NFPA 704
0
2 0

(S)-MEPHENYTOIN price More Price(25)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich UC175 (S)-(+)-Mephenytoin solid, ≥98% (HPLC) 70989-04-7 5mg $898 2024-03-01 Buy
Sigma-Aldrich UC175 (S)-(+)-Mephenytoin solid, ≥98% (HPLC) 70989-04-7 10mg $1570 2024-03-01 Buy
Cayman Chemical 11913 (S)-Mephenytoin ≥98% 70989-04-7 1mg $39 2024-03-01 Buy
Cayman Chemical 11913 (S)-Mephenytoin ≥98% 70989-04-7 5mg $96 2024-03-01 Buy
Cayman Chemical 11913 (S)-Mephenytoin ≥98% 70989-04-7 10mg $173 2024-03-01 Buy
Product number Packaging Price Buy
UC175 5mg $898 Buy
UC175 10mg $1570 Buy
11913 1mg $39 Buy
11913 5mg $96 Buy
11913 10mg $173 Buy

(S)-MEPHENYTOIN Chemical Properties,Uses,Production

Chemical Properties

White Crystalline Solid

Uses

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).

Uses

(S)-Mephenytoin can be 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.

(S)-MEPHENYTOIN Preparation Products And Raw materials

Raw materials

Preparation Products

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(S)-MEPHENYTOIN Spectrum

(S)-(+)-5-Ethyl-3-methyl-5-phenyl-2,4-imidazolidinedione, (S)-(+)-5-Ethyl-3-methyl-5-phenylhydantoin (5S)-5-Ethyl-3-methyl-5-phenylhydantoin (5S)-5β-Ethyl-3-methyl-5-phenylhydantoin Mephenitoin S (5S)-5-ethyl-3-methyl-5-phenyl-imidazolidine-2,4-dione (5S)-5-ethyl-3-methyl-5-phenylimidazolidine-2,4-dione (S)-(+)-MEPHENYTOIN (S)-(+)-5-ETHYL-3-METHYL-5-PHENYL-2,4-IMIDAZOLIDINEDIONE (S)-(+)-5-ETHYL-3-METHYL-5-PHENYLHYDANTOIN (S)-5-ETHYL-3-METHYL-5-PHENYLHYDANTOIN (5S)-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-phenyliMidazolidine-2,4-dione (S)-Mephenytoine (S)-MEPHENYTOIN Mephenytoin Impurity 2 (S)-Mephenitoin inhibit,(+)-Mephenytoin,cytochrome,Inhibitor,(S)Mephenytoin,CYP2C19,(S) Mephenytoin,P450,(S)-Mephenytoin,anticonvulsive (S)-(+)-Mephenytoin solid, >=98% (HPLC) 70989-04-7 Hydantoins and Derivatives Hydantoins & Derivatives Intermediates & Fine Chemicals Pharmaceuticals Heterocycles