Nirvanol

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Nirvanol

Systematic (IUPAC) name
5-ethyl-5-phenylimidazolidine-2,4-dione
Clinical data
Legal status	?
Routes	oral^[1]
Identifiers
CAS number	631-07-2
ATC code	None
PubChem	CID 91480
ChemSpider	82605
Synonyms	5-ethyl-5-phenylhydantoin
Chemical data
Formula	C₁₁H₁₂N₂O₂
Mol. mass	204.22518
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, 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. 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): 1746–1755. 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): 340–345. PMID 13109695.

External links

Anticonvulsants (N03)

GABA_A receptor agonist

Barbiturates	Barbexaclone Metharbital Methylphenobarbital Pentobarbital Phenobarbital^# Primidone

Benzodiazepines	Clobazam Clonazepam Clorazepate Diazepam^# Flutoprazepam Lorazepam Midazolam Nimetazepam Nitrazepam Temazepam

Other GABA agents

Aromatic allylic alcohols	Stiripentol

Carbonic anhydrase inhibitor

Sulfa drugs	Acetazolamide Ethoxzolamide Sultiame Zonisamide

Channel blockers

Primarily sodium

Hydantoins	Ethotoin Fosphenytoin Mephenytoin Phenytoin^#

Carboxamides	Carbamazepine^# Eslicarbazepine acetate Oxcarbazepine Oxitriptyline Rufinamide

Primarily calcium

Succinimides	Ethosuximide^# Mesuximide Phensuximide

AMPA receptor

Perampanel

Unknown/ungrouped

Phenyltriazine (Lamotrigine), Oxazolidinediones (Ethadione
Paramethadione
Trimethadione), Ureas (Phenacemide
Pheneturide), Monosaccharide (Topiramate)

Channel openers

Potassium	Retigabine

Indirect GABA agents

Carboxylic acids/ Fatty acid derivatives	GABA transaminase inhibitor: Valproic acid^# (Sodium valproate & Valproate semisodium) Valpromide Valnoctamide Valproate pivoxil GABA reuptake inhibitor: Tiagabine

GABA analogs	Gabapentin Pregabalin Progabide Tolgabide Vigabatrin

Unknown/multiple/
unsorted

Carbamates/sulfamates	Carisbamate^† Emylcamate Felbamate JNJ-26990990^§ Meprobamate Topiramate

Pyrrolidines	Brivaracetam Levetiracetam Nefiracetam Seletracetam

Propionates	Beclamide Lacosamide

Aldehydes	Paraldehyde

Bromides	Potassium bromide Sodium bromide

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

M: CNS

anat (n/s/m/p/4/e/b/d/c/a/f/l/g)/phys/devp

noco (m/d/e/h/v/s)/cong/tumr, sysi/epon, injr

proc, drug (N1A/2AB/C/3/4/7A/B/C/D)

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