Nirvanol

Nirvanol
Clinical data
Other names	5-Ethyl-5-phenylhydantoin
Routes of; administration	By mouth[1]
ATC code	None;
Identifiers
	IUPAC name 5-Ethyl-5-phenylimidazolidine-2,4-dione;
CAS Number	631-07-2;
PubChem CID	91480;
ChemSpider	82605;
UNII	23SM1FA1AK;
CompTox Dashboard (EPA)	DTXSID80874185 ;
ECHA InfoCard	100.010.138
Chemical and physical data
Formula	C11H12N2O2
Molar mass	204.22518 g·mol−1
3D model (JSmol)	Interactive image;
	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.[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

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[Theodore1984-1] 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.

[Read1922-2] 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.

[Ashby1930-3] 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.

[Kupfer1984-4] 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.

[Butler1953-5] 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.