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(S)-Mephenytoin
(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].
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.
Physical Appearance | A crystalline solid |
Storage | Store at -20°C |
M.Wt | 218.3 |
Cas No. | 70989-04-7 |
Formula | C12H14N2O2 |
Synonyms | (S)-5-Ethyl-3-methyl-5-phenylhydantoin |
Solubility | ≤15mg/ml in ethanol;25mg/ml in DMSO;25mg/ml in dimethyl formamide |
Chemical Name | (5S)-5-ethyl-3-methyl-5-phenyl-2,4-imidazolidinedione |
SDF | Download SDF |
Canonical SMILES | O=C1[C@@](C2=CC=CC=C2)(CC)NC(N1C)=O |
Shipping Condition | Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice. |
General tips | We do not recommend long-term storage for the solution, please use it up soon. |
Quality Control & MSDS
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Purity = 98.00%
- COA (Certificate Of Analysis)
- MSDS (Material Safety Data Sheet)
- Datasheet