Nirvanol
 | |
| Clinical data | |
|---|---|
| Routes of administration | By mouth[1] |
| ATC code | None |
| Identifiers | |
| |
| Synonyms | 5-Ethyl-5-phenylhydantoin |
| CAS Number | 631-07-2 |
| PubChem (CID) | 91480 |
| ChemSpider | 82605 |
| ECHA InfoCard | 100.010.138 |
| Chemical and physical data | |
| Formula | C11H12N2O2 |
| Molar mass | 204.22518 |
| 3D model (Jmol) | Interactive image |
| |
| |
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, W. H.; Newmark, M. E.; Desai, B. T.; Kupferberg, H. J.; Penry, J. K.; Porter, R. J.; Yonekawa, W. D. (1 August 1984). "Disposition of mephenytoin and its metabolite, nirvanol, in epileptic patients". Neurology. 34 (8): 1100–1102. doi:10.1212/wnl.34.8.1100. PMID 6431315.
- ↑ Read, William T. (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, Hugh T. (February 1930). "Treatment of Chorea by Nirvanol". J. Pharmacol. Exp. Ther. 5 (25): 42–43. doi:10.1136/adc.5.25.42.
- ↑ Küpfer, A.; Patwardhan, R.; Ward, S.; Schenker, S.; Preisig, R.; Branch, R. A. (July 1984). "Stereoselective metabolism and pharmacogenetic control of 5-phenyl-5-ethylhydantoin (nirvanol) in humans". J. Pharmacol. Exp. Ther. 230 (1): 28–33. PMID 6747829.
- ↑ Butler, Thomas C. (November 1953). "Quantitative studies of the physiological disposition of 3-methyl-5-ethyl-5-phenyl hydantoin (mesantoin) and 5-ethyl-5-phenyl hydantoin (nirvanol)". J. Pharmacol. Exp. Ther. 109 (3): 340–5. PMID 13109695.
External links
- Comparative Toxicogenomics Database: ethylphenylhydantoin
- MeSH Supplementary Concept Data: ethylphenylhydantoin
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