Structure via PubChem · Public domain (PubChem)
ethylphenylhydantoin
Sign in to saveAlso known as nirvanol
Nirvanol, also known as ethylphenylhydantoin, is a derivative of hydantoin with anticonvulsant properties. Its 5-ethyl-5-phenyl substitution pattern is similar to that of phenobarbital. It is useful in the treatment of chorea.
Chemical data
- Formula
- C11H12N2O2
- Molecular weight
- 204.22 g/mol
- IUPAC name
- 5-ethyl-5-phenylimidazolidine-2,4-dione
- SMILES
- CCC1(C(=O)NC(=O)N1)C2=CC=CC=C2
- InChIKey
- UDTWZFJEMMUFLC-UHFFFAOYSA-N
- XLogP
- 1.5
- Polar surface area
- 58.2 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
41 papers- Induction of a pleiotropic response by phenobarbital and related compounds. Response in various inbred strains of rats, response in various species and the induction of aldehyde dehydrogenase in Copenhagen rats.Biochemical pharmacology · 1992
- [Experimental ophthalmopathic syndrome in guinea pigs caused by prolonged administration of 3-methyl-5-ethylphenylhydantoin].Rivista di anatomia patologica e di oncologia · 1961
- Comparative actions of phenytoin and other anticonvulsant drugs on potassium- and veratridine-stimulated calcium uptake in synaptosomes.The Journal of pharmacology and experimental therapeutics · 1982
- [Ophthalmopathic changes observed in the offspring of guinea pigs treated by the administration of 3-methyl-5,5-ethylphenylhydantoin 7 months before conception].Rivista di anatomia patologica e di oncologia · 1964
- Genetic polymorphism of mephenytoin metabolism.Progress in clinical and biological research · 1986
via PubMed
Wikidata facts
- Subclass of
- medication
- Mass
- 204.089878
Show 3 more facts
- chemical formula
- C₁₁H₁₂N₂O₂
- canonical SMILES
- CCC1(C(=O)NC(=O)N1)C2=CC=CC=C2
- subject has role
- anticonvulsant agent
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Metabolism
- References
- External links
Nirvanol, also known as ethylphenylhydantoin, is a derivative of hydantoin with anticonvulsant properties. Its 5-ethyl-5-phenyl substitution pattern is similar to that of phenobarbital. It is useful in the treatment of chorea.
==Metabolism== Metabolism of nirvanol is stereoselective, with the (S)- enantiomer undergoing roughly 14 times more hydroxylation at the 4 position of the phenyl group than the (R)-enantiomer.
Excerpted from Wikipedia’s “ethylphenylhydantoin” article, available under the CC BY-SA 4.0 licence.