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(S)-MEPHENYTOIN

Product Name
(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
Formula Weight
218.25
MOL File
70989-04-7.mol
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(S)-MEPHENYTOIN Property

Melting point:
135-138 °C
Density 
1.154±0.06 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
DMSO: soluble
pka
8.07±0.70(Predicted)
form 
solid
color 
off-white
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Safety

Hazard Codes 
Xn
Risk Statements 
22-36/37/38
Safety Statements 
26-36
WGK Germany 
2
HS Code 
29332100
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
UC175
Product name
(S)-(+)-Mephenytoin
Purity
solid, ≥98% (HPLC)
Packaging
5mg
Price
$898
Updated
2024/03/01
Sigma-Aldrich
Product number
UC175
Product name
(S)-(+)-Mephenytoin
Purity
solid, ≥98% (HPLC)
Packaging
10mg
Price
$1570
Updated
2024/03/01
Cayman Chemical
Product number
11913
Product name
(S)-Mephenytoin
Purity
≥98%
Packaging
1mg
Price
$39
Updated
2024/03/01
Cayman Chemical
Product number
11913
Product name
(S)-Mephenytoin
Purity
≥98%
Packaging
5mg
Price
$96
Updated
2024/03/01
Cayman Chemical
Product number
11913
Product name
(S)-Mephenytoin
Purity
≥98%
Packaging
10mg
Price
$173
Updated
2024/03/01
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(S)-MEPHENYTOIN Chemical Properties,Usage,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 Suppliers

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70989-04-7, (S)-MEPHENYTOINRelated Search:


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  • (S)-(+)-Mephenytoin solid, >=98% (HPLC)
  • 70989-04-7
  • Hydantoins and Derivatives
  • Hydantoins & Derivatives
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Heterocycles