Chemistry:Nirvanol
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Short description: Chemical compound
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| Other names | 5-Ethyl-5-phenylhydantoin |
| Routes of administration | By mouth[1] |
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| Formula | C11H12N2O2 |
| Molar mass | 204.22518 g·mol−1 |
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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
- ↑ "Disposition of mephenytoin and its metabolite, nirvanol, in epileptic patients". Neurology 34 (8): 1100–2. August 1984. 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. https://zenodo.org/record/1428800.
- ↑ "Treatment of Chorea by Nirvanol". Archives of Disease in Childhood 5 (25): 42–3. February 1930. doi:10.1136/adc.5.25.42. PMID 21031794.
- ↑ "Stereoselective metabolism and pharmacogenetic control of 5-phenyl-5-ethylhydantoin (nirvanol) in humans". The Journal of Pharmacology and Experimental Therapeutics 230 (1): 28–33. July 1984. PMID 6747829. http://jpet.aspetjournals.org/content/230/1/28.abstract.
- ↑ "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. November 1953. PMID 13109695. http://jpet.aspetjournals.org/cgi/content/abstract/109/3/340.
External links
- Comparative Toxicogenomics Database: ethylphenylhydantoin
- MeSH Supplementary Concept Data: ethylphenylhydantoin
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