Mephenytoin

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Mephenytoin
Systematic (IUPAC) name
5-ethyl-3-methyl-5-phenyl-imidazolidine-2,4-dione
Identifiers
CAS number	50-12-4
ATC code	N03AB04
PubChem	4060
DrugBank	APRD00512
Chemical data
Formula	C12H14N2O2
Mol. weight	218.256
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	7 hours
Excretion	?
Therapeutic considerations
Pregnancy cat.	C (USA)
Legal status
Routes	Oral

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.

[edit] 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) edit

Barbiturates: Barbexaclone, Metharbital, Methylphenobarbital, Phenobarbital, Primidone Hydantoins: Ethotoin, Fosphenytoin, Mephenytoin, Phenytoin Oxazolidinediones: Ethadione, Paramethadione, Trimethadione Succinimides: Ethosuximide, Mesuximide, Phensuximide Benzodiazepines: Clobazam, Clonazepam, Clorazepate, Diazepam, Lorazepam, Midazolam, Nitrazepam, Temazepam Carboxamides: Carbamazepine, Oxcarbazepine, Rufinamide Fatty acid derivatives: Valpromide, Valnoctamide Carboxylic acids: Valproic acid (Sodium valproate & Valproate semisodium), Tiagabine -- GABA analogs: Gabapentin, Pregabalin, Progabide, Vigabatrin Others:- Monosaccharides: Topiramate -- Aromatic allylic alcohols: Stiripentol -- Ureas: Phenacemide, Pheneturide -- Phenyltriazines: Lamotrigine Carbamates: Emylcamate, Felbamate, Meprobamate -- Pyrrolidines: Brivaracetam, Levetiracetam, Nefiracetam, Seletracetam Sulfa drugs: Acetazolamide, Ethoxzolamide, Sultiame, Zonisamide -- Propionates: Beclamide -- Aldehydes: Paraldehyde -- Bromides: Potassium bromide, Sodium bromide