Mephenytoin

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
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
    Chemical and physical data
    FormulaC12H14N2O2
    Molar mass218.252 g/mol g·mol−1
    3D model (JSmol)
      (verify)

    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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