Nirvanol
Chemical compound
- None
- 5-Ethyl-5-phenylimidazolidine-2,4-dione
- 631-07-2
- 91480
- 82605
- 23SM1FA1AK
- DTXSID80874185
- Interactive image
- 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.[2] It is useful in the treatment of chorea.[3]
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.[4][5]
References
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
External links
- Comparative Toxicogenomics Database: ethylphenylhydantoin
- MeSH Supplementary Concept Data: ethylphenylhydantoin
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Anticonvulsants (N03)
| GABAAR PAMs |
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| GABA-T inhibitors |
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| Others |
modulators
| CA inhibitors |
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| Others |
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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