Mephenytoin

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Mephenytoin

Systematic (IUPAC) name
5-ethyl-3-methyl-5-phenyl-imidazolidine-2,4-dione
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a611020
Pregnancy cat.	C (US)
Legal status	?
Routes	Oral
Pharmacokinetic data
Half-life	7 hours
Identifiers
CAS number	50-12-4^Y
ATC code	N03AB04
PubChem	CID 4060
DrugBank	DB00532
ChemSpider	3920^Y
UNII	R420KW629U^Y
KEGG	D00375^Y
ChEMBL	CHEMBL861^Y
Chemical data
Formula	C₁₂H₁₄N₂O₂
Mol. mass	218.252
SMILES O=C2N(C(=O)NC2(c1ccccc1)CC)C
InChI InChI=1S/C12H14N2O2/c1-3-12(9-7-5-4-6-8-9)10(15)14(2)11(16)13-12/h4-8H,3H2,1-2H3,(H,13,16)^Y Key:GMHKMTDVRCWUDX-UHFFFAOYSA-N^Y
Y (what is this?) (verify)

Mephenytoin (marketed as Mesantoin by Novartis) is a hydantoin, used as an anticonvulsant. It was introduced approximately 10 years after phenytoin, in the late 1940s. The significant metabolite of mephenytoin is nirvanol (5-ethyl-5-phenylhydantoin), which was the first hydantoin (briefly used as a hypnotic). However, nirvanol is quite toxic and mephenytoin was only considered after other less toxic anticonvulsants had failed. It can cause potentially fatal blood dyscrasia in 1% of patients.

Mephenytoin is no longer available in the US or the UK. It is still studied largely because of its interesting hydroxylation polymorphism.

References

The Treatment of Epilepsy edited by S. D. Shorvon, David R. Fish, Emilio Perucca, W. Edwin Dodson. Blackwell Publishing. 2004. ISBN 0-632-06046-8
The Medical Treatment of Epilepsy by Stanley R Resor. Published by Marcel Dekker (1991). ISBN 0-8247-8549-5.
The Comparative Toxicogenomics Database: Mephenytoin

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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