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Mephenytoin

Mephenytoin
Structural formula of mephenytoin
Space-filling model of the mephenytoin molecule
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa611020
Pregnancy
category
  • US: C (Risk not ruled out)
Routes of
administration
Oral
ATC code
Pharmacokinetic data
MetabolismCYP2C19
Elimination half-life7 hours
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.012 Edit this at Wikidata
Chemical and physical data
FormulaC12H14N2O2
Molar mass218.252 g/mol g·mol−1
3D model (JSmol)
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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