An anticonvulsant agent
Related Products
Labeled Version(s)
33245Phenytoin-d10
Pro-drug Form(s)
23889Fosphenytoin (sodium salt)
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Phenytoin

Item No. 24037

Product Insert (PDF)GC-MS (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5,5-diphenyl-2,4-imidazolidinedione
CAS Number
57-41-0
Synonyms
  • 5,5-Diphenylhydantoin
  • NSC 8722
Molecular Formula
C15H12N2O2
Formula Weight
252.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 25 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/mlEthanol: 15 mg/ml
SMILES
O=C(C(C1=CC=CC=C1)(C2=CC=CC=C2)N3)NC3=O
InChi Code
InChI=1S/C15H12N2O2/c18-13-15(17-14(19)16-13,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H,(H2,16,17,18,19)
InChi Key
CXOFVDLJLONNDW-UHFFFAOYSA-N
Shipping & Storage Information
Storage
4°C
Shipping
Wet ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    50 g

    $32

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    100 g

    $54

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    250 g

    $128

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    Product Description

    Phenytoin is an anticonvulsant agent and active metabolite of fosphenytoin (Item No. 23889). Phenytoin is formed from fosphenytoin by tissue phosphatases.1 It inhibits neuronal voltage-gated sodium channels in a voltage-dependent manner.2 Phenytoin reduces the neuronal firing frequency and decreases the amplitude of excitatory post-synaptic potentials (EPSPs) in electrically stimulated rat corticostriatal slices (EC50s = 42.8 and 33.5 µM, respectively).3 It protects against seizures induced by maximal electroshock (MES) in mice (ED50 = 10 mg/kg).4 Formulations containing phenytoin have been used in the treatment of tonic-clonic seizures and status epilepticus.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Boucher, B.A. Fosphenytoin: A novel phenytoin prodrug. Pharmacotherapy 16(5), 777-791 (1996).

    2. Yaari, Y., Selzer, M.E., and Pincus, J.H. Phenytoin: Mechanisms of its anticonvulsant action. Ann. Neurol. 20(2), 171-184 (1986).

    3. Calabresi, P., Centonze, D., Marfia, G.A., et al. An in vitro electrophysiological study on the effects of phenytoin, lamotrigine and gabapentin on striatal neurons. Br. J. Pharmacol. 126(3), 689-696 (1999).

    4. Brouillette, W.J., Jestkov, V.P., Akhtar, M.S., et al. Bicyclic hydantoins with a bridgehead nitrogen. Comparison of anticonvulsant activities with binding to the neuronal voltage-dependent sodium channel. J. Med. Chem. 37(20), 3289-3293 (1994).