70989-04-7 Usage
Description
(S)-Mephenytoin, also known as mephenytoin, is a chiral compound that is the active isomer of the anticonvulsant drug mephenytoin. It is a white crystalline solid with a molecular formula of C12H13NO2 and a molecular weight of 207.24 g/mol. (S)-Mephenytoin is known for its ability to inhibit the activity of cytochrome P450 enzymes, particularly CYP2C19, making it a useful tool in the study of drug metabolism and pharmacogenetics.
Used in Pharmaceutical Industry:
(S)-Mephenytoin is used as an anticonvulsant agent for the treatment of epilepsy and seizures. It works by stabilizing the inactivated state of voltage-gated sodium channels, thereby reducing the spread of seizure activity in the brain.
Used in Research and Development:
(S)-Mephenytoin is used as a CYP2C19 substrate for the analysis of cytochrome P450 metabolism. This allows researchers to study the genetic variations in the CYP2C19 enzyme and their impact on drug metabolism and response.
Used in Analytical Chemistry:
(S)-Mephenytoin has been used as probe substrates for LC/MS-based analysis of relative activity factor (RAF). This helps in the evaluation of the activity of cytochrome P450 enzymes and their role in drug metabolism and drug-drug interactions.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 70989-04-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,0,9,8 and 9 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 70989-04:
(7*7)+(6*0)+(5*9)+(4*8)+(3*9)+(2*0)+(1*4)=157
157 % 10 = 7
So 70989-04-7 is a valid CAS Registry Number.
InChI:InChI=1/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
70989-04-7Relevant articles and documents
Pseudoephedrine-Directed Asymmetric α-Arylation of α-Amino Acid Derivatives
Atkinson, Rachel C.,Fernández-Nieto, Fernando,Mas Rosell?, Josep,Clayden, Jonathan
supporting information, p. 8961 - 8965 (2015/08/03)
Available α-amino acids undergo arylation at their α position in an enantioselective manner on treatment with base of N′-aryl urea derivatives ligated to pseudoephedrine as a chiral auxiliary. In situ silylation and enolization induces diastereoselective migration of the N′-aryl group to the α position of the amino acid, followed by ring closure to a hydantoin with concomitant explulsion of the recyclable auxiliary. The hydrolysis of the hydantoin products provides derivatives of quaternary amino acids. The arylation avoids the use of heavy-metal additives, and is successful with a range of amino acids and with aryl rings of varying electronic character.
Racemic and Optically Active Hydantoins from Disubstituted Cyanoacetic Acids
Knabe, Joachim,Wunn, Wolfgang
, p. 538 - 543 (2007/10/02)
Starting from the chiral disubstituted cyanoacetic acids 1 the racemates and some enantiomers of the 5,5-disubstituted hydantoins 6 and of the 3-methylhydantoins 7 are synthesized via the isocyanates 3.Their absolute configurations are determined.
