70989-04-7 Usage
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 academic research and scientific papers
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.
Chromatographic Resolutions of Racemates, XI. Comparison of Optically Active Polyamides and Cellulose Triacetate
Blaschke, Gottfried,Kraft, Horst Peter,Markgraf, Hildegunde
, p. 3611 - 3617 (2007/10/02)
On optically active polyacrylic and polymethacrylic amides (1a-e) as well as on microcrystalline cellulose triacetate (2), numerous racemates including drugs are separated at least partially, the amide 4f completely on cellulose triacetate.By repeated chromatography on the polyamide 1a, (+)- and (-)-mandelic acid (4a) and (+)-hexobarbital (9d) also were obtained optically pure.
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.
