nirvanol

{{Short description|Chemical compound}}

{{Drugbox

| synonyms = 5-Ethyl-5-phenylhydantoin

| IUPAC_name = 5-Ethyl-5-phenylimidazolidine-2,4-dione

| image = Nirvanol.svg

| width = 125

| CAS_number = 631-07-2

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 23SM1FA1AK

| PubChem = 91480

| ChemSpiderID = 82605

| ATC_prefix = None

| C = 11 | H = 12 | N = 2 | O = 2

| StdInChI = 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)

| StdInChIKey = UDTWZFJEMMUFLC-UHFFFAOYSA-N

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| routes_of_administration = By mouth{{cite journal | vauthors = Theodore WH, Newmark ME, Desai BT, Kupferberg HJ, Penry JK, Porter RJ, Yonekawa WD | title = Disposition of mephenytoin and its metabolite, nirvanol, in epileptic patients | journal = Neurology | volume = 34 | issue = 8 | pages = 1100–2 | date = August 1984 | pmid = 6431315 | doi = 10.1212/wnl.34.8.1100 | s2cid = 7925715 }}

| smiles = CCC1(C(=O)NC(=O)N1)C2=CC=CC=C2

}}

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.{{Cite journal |last=Read |first=William T. | name-list-style = vanc |title=Researches on hydantoins. Synthesis of the soporific, 4,4-phenylethyl-hydantoin (nirvanol) |journal=J. Am. Chem. Soc. |volume=44 |issue=8 |pages=1746–55 |date=August 1922 |doi=10.1021/ja01429a017 |url=https://zenodo.org/record/1428800 }} It is useful in the treatment of chorea.{{cite journal | vauthors = Ashby HT | title = Treatment of Chorea by Nirvanol | journal = Archives of Disease in Childhood | volume = 5 | issue = 25 | pages = 42–3 | date = February 1930 | pmid = 21031794 | pmc = 1975064 | doi = 10.1136/adc.5.25.42 }}

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.{{cite journal | vauthors = Küpfer A, Patwardhan R, Ward S, Schenker S, Preisig R, Branch RA | title = Stereoselective metabolism and pharmacogenetic control of 5-phenyl-5-ethylhydantoin (nirvanol) in humans | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 230 | issue = 1 | pages = 28–33 | date = July 1984 | pmid = 6747829 | url = http://jpet.aspetjournals.org/content/230/1/28.abstract }}{{cite journal | vauthors = Butler TC | title = Quantitative studies of the physiological disposition of 3-methyl-5-ethyl-5-phenyl hydantoin (mesantoin) and 5-ethyl-5-phenyl hydantoin (nirvanol) | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 109 | issue = 3 | pages = 340–5 | date = November 1953 | pmid = 13109695 | url = http://jpet.aspetjournals.org/cgi/content/abstract/109/3/340 }}

References

{{Reflist}}