65567-34-2

Basic information

• Product Name: (S)-(+)-NIRVANOL
• Synonyms: (S)-(+)-NIRVANOL;S-(+)-N-DESMETHYLMEPHENTOIN;S-(+)-DESMETHYLMEPHENTOIN;(S)-(+)-5-ETHYL-5-PHENYL-2,4-IMIDAZOLIDINEDIONE;(S)-(+)-5-ETHYL-5-PHENYLHYDANTOIN;(+)-hydantoi;5-ethyl-5-phenyl-4-imidazolidinedion(s)-;S-(+)-N-Desmethyl Mephenytoin
• CAS NO: 65567-34-2
• Molecular Formula: C₁₁H₁₂N₂O₂
• Molecular Weight: 204.23
• Product Categories: Miscellaneous Natural Products;Various Metabolites and Impurities;Hydantoins & Derivatives;Metabolites;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 65567-34-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 195-200°C
• Appearance: off-white/
• Storage Temp.: 2-8°C
• Solubility: DMF: soluble
• CAS DataBase Reference: (S)-(+)-NIRVANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-NIRVANOL(65567-34-2)
• EPA Substance Registry System: (S)-(+)-NIRVANOL(65567-34-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 26-37/39-36
• WGK Germany: 2
• RTECS: MU2452000
• Hazardous Substances Data: 65567-34-2(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

An anticonvulsant, hypnotic. A metabolite of Mephentoin

InChI:InChI=1/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)

Upstream product

• 33875-36-4 2-Isocyanato-2-phenyl-butyronitrile 
• 75356-44-4 (1-Cyano-1-phenyl-propyl)-urea 
• 70989-04-7 S-mephenytoin 
• 220599-90-6 (+/-)-2-formylamino-2-phenyl-butyric acid 
• 220599-84-8 (S)-2-formylamino-2-phenyl-butyric acid 
• 52247-77-5 (S)-2‐amino‐2‐phenylbutyric acid 
• 5438-07-3 2-amino-2-phenylbutanoic acid 
• 33875-36-4 2-Isocyanato-2-phenyl-butyronitrile 
• 2216-93-5 5-ethyl-5-phenyl-imidazolidine-2,4-dione 
• 75356-44-4 (1-Cyano-1-phenyl-propyl)-urea 
• 57-13-6 urea 
• 52165-63-6 ethyl (S)-2-amino-2-phenylbutanoate 

Relevant articles and documents

Retrorsine, but not monocrotaline, is a mechanism-based inactivator of P450 3A4

Retrorsine (RTS) and monocrotaline (MCT) cause severe toxicities via P450-mediated metabolic activation. The screening of mechanism-based inhibitors showed RTS inactivated 3A4 in the presence of NADPH. Unlike RTS, MCT failed to inhibit P450 3A4 and other enzymes tested. Further studies showed the loss of P450 3A4 activity occurred in a time- and concentration-dependent way, which was not recovered after dialysis. Dextromethorphan, a P450 3A4 substrate, protected the enzyme from the inactivation. Exogenous nucleophile glutathione (GSH) and reactive oxygen species scavengers catalase and superoxide dismutase did not protect P450 3A4 from the inactivation. GSH trapping experiments showed both P450 3A4 and 2C19 converted RTS and MCT to the corresponding electrophilic metabolites which could be trapped by GSH to form 7-GSH-DHP conjugate. We conclude that RTS and MCT are metabolically activated by P450 3A4 and 2C19, and that RTS, but not MCT, is a mechanism-based inactivator of P450 3A4.

Racemic and Optically Active Hydantoins from Disubstituted Cyanoacetic Acids

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.