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Mephenytoin

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Mephenytoin

Mephenytoin
Structural formula of mephenytoin
Space-filling model of the mephenytoin molecule
Systematic (IUPAC) name
5-ethyl-3-methyl-5-phenyl-imidazolidine-2,4-dione
Clinical data
AHFS/Drugs.com
MedlinePlus
Pregnancy
category
  • US: C (Risk not ruled out)
Routes of
administration
Oral
Pharmacokinetic data
Biological half-life 7 hours
Identifiers
CAS Registry Number  YesY
ATC code N03
PubChem CID:
IUPHAR/BPS
DrugBank  YesY
ChemSpider  YesY
UNII  YesY
KEGG  YesY
ChEMBL  YesY
Chemical data
Formula C12H14N2O2
Molecular mass
Documentation

 YesY   

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


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