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Nirvanol

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Chemical compound Pharmaceutical compound
Nirvanol
Clinical data
Other names5-Ethyl-5-phenylhydantoin
Routes of
administration		By mouth
ATC code
  • None
Identifiers
IUPAC name
  • 5-Ethyl-5-phenylimidazolidine-2,4-dione
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.010.138 Edit this at Wikidata
Chemical and physical data
FormulaC11H12N2O2
Molar mass204.229 g·mol
3D model (JSmol)
SMILES
  • CCC1(C(=O)NC(=O)N1)C2=CC=CC=C2
InChI
  • 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)
  • Key:UDTWZFJEMMUFLC-UHFFFAOYSA-N

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.

References

  1. Theodore WH, Newmark ME, Desai BT, Kupferberg HJ, Penry JK, Porter RJ, Yonekawa WD (August 1984). "Disposition of mephenytoin and its metabolite, nirvanol, in epileptic patients". Neurology. 34 (8): 1100–2. doi:10.1212/wnl.34.8.1100. PMID 6431315. S2CID 7925715.
  2. Read WT (August 1922). "Researches on hydantoins. Synthesis of the soporific, 4,4-phenylethyl-hydantoin (nirvanol)". J. Am. Chem. Soc. 44 (8): 1746–55. doi:10.1021/ja01429a017.
  3. Ashby HT (February 1930). "Treatment of Chorea by Nirvanol". Archives of Disease in Childhood. 5 (25): 42–3. doi:10.1136/adc.5.25.42. PMC 1975064. PMID 21031794.
  4. Küpfer A, Patwardhan R, Ward S, Schenker S, Preisig R, Branch RA (July 1984). "Stereoselective metabolism and pharmacogenetic control of 5-phenyl-5-ethylhydantoin (nirvanol) in humans". The Journal of Pharmacology and Experimental Therapeutics. 230 (1): 28–33. PMID 6747829.
  5. Butler TC (November 1953). "Quantitative studies of the physiological disposition of 3-methyl-5-ethyl-5-phenyl hydantoin (mesantoin) and 5-ethyl-5-phenyl hydantoin (nirvanol)". The Journal of Pharmacology and Experimental Therapeutics. 109 (3): 340–5. PMID 13109695.

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