Product Name

Phenytoin

CAS Number

57-41-0

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Product Name:
Phenytoin
CAS Number:
57-41-0
Indication:
For the control of generalized tonic-clonic (grand mal) and complex partial (psychomotor, temporal lobe) seizures and prevention and treatment of seizures occurring during or following neurosurgery.
Mode of Action:

Phenytoin acts on sodium channels on the neuronal cell membrane, limiting the spread of seizure activity and reducing seizure propagation. By promoting sodium efflux from neurons, phenytoin tends to stabilize the threshold against hyperexcitability caused by excessive stimulation or environmental changes capable of reducing membrane sodium gradient. This includes the reduction of post-tetanic potentiation at synapses. Loss of post-tetanic potentiation prevents cortical seizure foci from detonating adjacent cortical areas.

Pharmacodynamics:

Phenytoin is an antiepileptic drug which can be useful in the treatment of epilepsy. The primary site of action appears to be the motor cortex where spread of seizure activity is inhibited. Phenytoin reduces the maximal activity of brain stem centers responsible for the tonic phase of tonic-clonic (grand mal) seizures. Phenytoin acts to dampen the unwanted, runaway brain activity seen in seizure by reducing electrical conductance among brain cells. It lacks the sedation effects associated with phenobarbital. There are some indications that phenytoin has other effects, including anxiety control and mood stabilization, although it has never been approved for those purposes by the FDA. Phenytoin is primarily metabolized by CYP2C9.

Metabolism:

Primarily hepatic

Toxicity:

Oral, mouse: LD50 = 150 mg/kg; Oral, rat: LD50 = 1635 mg/kg. Symptoms of overdose include coma, difficulty in pronouncing words correctly, involuntary eye movement, lack of muscle coordination, low blood pressure, nausea, sluggishness, slurred speech, tremors, and vomiting.

IUPAC:
5, 5-diphenylimidazolidine-2, 4-dione
ATC:
N03AB02 N03AB04 N03AB05
DrugBank:
DB00252 (APRD00241)
Formula:
C10H16Br2N2O2
Molecular Mass:
252.268
Synonyms:
5,5-diphenylhydantoin 5,5-Dwufenylohydantoina Difenilhidantoina [Spanish] Dihydantoin Diphenylan Sodium Diphenylhydantoin Diphenylhydantoine [French] Diphenylhydatanoin Fenitoina [INN-Spanish] Phenytoin Sodium Phenytoine Phenytoine [INN-French] Phenytoinum [INN-Latin]
SMILES:
O=C1NC(=O)C(N1)(C1=CC=CC=C1)C1=CC=CC=C1
AHFS Code:
28:12.1
InChi:
CXOFVDLJLONNDW-UHFFFAOYSA-N

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