rac N-desmethyl mephenytoin

CAS: 631-07-2

Ref. 3D-FR27558

Product Information

• Name: rac N-desmethyl mephenytoin
• Synonyms: (+/-)-Nirvanol(+/-)-5-Ethyl-5-phenylhydantoin(RS)-5-ethyl-5-phenyl-2,4-imidazolidinedione, (5R)-5-ethyl-5-phenylimidazolidine-2,4-dione, (5S)-5-ethyl-5-phenylimidazolidine-2,4-dione, (RS)-5-Ethyl-5-phenyl-2,4-imidazolidinedione, 2,4-Imidazolidinedione, 5-ethyl-5-phenyl-, 2,4-Imidazolidinedione, 5-ethyl-5-phenyl- (9CI), 5-Ethyl-5-Phenylimidazolidine-2,4-Dione, 5-Ethyl-5-phenyl-2,4-imidazolidinedione, 5-Ethyl-5-phenyl-2,4-imidazolidinedione (9CI), 5-Ethyl-5-phenylhydantoin, 5-Phenyl-5-ethylhydantoin, Desmethylmephenytoin, Ethylphenylhydantoin, Hydantoin, 5-ethyl-5-phenyl-, NSC 33388, Nirvanol, Normephenytoin, Nsc 150466

Description

Rac-N-desmethyl mephenytoin is a prodrug of carbamazepine that has been shown to be a potent inducer of the hepatic enzymes CYP2C9 and CYP3A4. This drug is not metabolized in humans, but undergoes metabolic conversion in vitro by esterases, as well as oxidation and reduction reactions. Rac-N-desmethyl mephenytoin is also an enantiomer of carbamazepine, which has been shown to be more potent than its counterpart. Rac-N-desmethyl mephenytoin has a low solubility in water and is mainly taken up by the liver cells after oral administration. It binds to growth factors (e.g., epidermal growth factor) on the cell surface and induces cell proliferation via hydrogen bonding interactions.

• Brand: Biosynth

Chemical properties

• Molecular weight: 204.23 g/mol
• Formula: C₁₁H₁₂N₂O₂
• Purity: Min. 95%
• InChI: InChI=1S/C11H12N2O2/c1-2-11(8-6-4-3-5-7-8)9(14)12-10(15)13-11/h3-7H,2H2,1H3,(H2,12,13,14,15)
• InChI key: InChIKey=UDTWZFJEMMUFLC-UHFFFAOYSA-N
• SMILES: CCC1(c2ccccc2)NC(=O)NC1=O