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QuickView for Phenytoin (compound)


PubChem
Name: Phenytoin
PubChem Compound ID: 1775
Description: An anticonvulsant that is used in a wide variety of seizures. It is also an anti-arrhythmic and a muscle relaxant. The mechanism of therapeutic action is not clear, although several cellular actions have been described including effects on ion channels, active transport, and general membrane stabilization. The mechanism of its muscle relaxant effect appears to involve a reduction in the sensitivity of muscle spindles to stretch. Phenytoin has been proposed for several other therapeutic uses, but its use has been limited by its many adverse effects and interactions with other drugs.
Molecular formula: C15H12N2O2
Molecular weight: 252.268 g/mol
Synonyms:
Hidantina vitoria; Phenytoin AWD; Fenitoina [INN-Spanish]; Diphenylhydatanoin; 5,5-diphenylimidazolidine-2,4-dione; Dihycon; Saceril; Auranile; Comitoina; NSC8722.
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DrugBank
Identification
Name: Phenytoin
Name (isomeric): DB00252
Drug Type: small molecule
Description: An anticonvulsant that is used in a wide variety of seizures. It is also an anti-arrhythmic and a muscle relaxant. The mechanism of therapeutic action is not clear, although several cellular actions have been described including effects on ion channels, active transport, and general membrane stabilization. The mechanism of its muscle relaxant effect appears to involve a reduction in the sensitivity of muscle spindles to stretch. Phenytoin has been proposed for several other therapeutic uses, but its use has been limited by its many adverse effects and interactions with other drugs.
Synonyms:
Fenitoina [INN-Spanish]; 5,5-diphenylhydantoin; 5,5-Dwufenylohydantoina; Diphenylhydatanoin; Dihydantoin; Phenytoinum [INN-Latin]; Diphenylhydantoine [French]; Difenilhidantoina [Spanish]; Phenytoine; Diphenylan Sodium.
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Brand: Epinat, Dilantine, Difenilhidantoina, Dantinal, Hidantina, Phenhydan, Dihycon, Dilantin acid, Hydantal, Citrulliamon, Sylantoic, Lehydan, Zentronal, Dintoin, Hydantin, Aleviatin, Hidantina senosian, Phenitoin, Epilan, Zentropil, Diphenylan, Hydantoinal, Denyl, Didan TDC 250, Diphenine, Fenytoin Dak, Epihydan, Eptal, Hydantoin, Phenatine, Hidantilo, Neos-Hidantoina, Ditoinate, Fenidantoin s, Sodantoin, Diphentoin, Epdantoin Simple, Saceril, Dilantin, Tacosal, Comital, Epilan D, Sodanthon, Danten, Hidan, Solantin, Di-Lan, Difenin, Ritmenal, Om-Hydantoine, Solantyl, Ictalis simple, Iphenylhydantoin, Dillantin, Fenylepsin, Solantoin, Phanatine, Toin unicelles, Fentoin, Enkelfel, Phentytoin, Diphedan, Minetoin, Oxylan, Epised, Kessodanten, Causoin, Lepsin, TOIN, Novantoina, Convul, Hidantal, Phenhydanin, Prompt Phenytoin Sodium, Diphedal, Diphenin, Dilantin-125, Di-Hydan, Mesantoin, Phenatoine, Novophenytoin, Thilophenyl, Epamin, Lepitoin, Epifenyl, Sanepil, Epilan-D, Eptoin, Diphenat, Antisacer, Labopal, Epdantoine simple, Difhydan, Sinergina, Epilantin, Ekko, Phanantin, Om hidantoina simple, Hidantina vitoria, Hydantol, Fenantoin, Epanutin, Phenytoin AWD, Auranile, Citrullamon, Dintoina, Diphentyn, Idantoin, Dilabid, Silantin, Epasmir 5, Dantoinal, Fenytoine, Diphantoin, Phentoin, Dantoine, Idantoil, Phenytex, Epelin, Sodanton, Elepsindon, Difetoin, Neosidantoina, Hindatal, Di-Phetine, Dantoinal klinos, Comitoina, Phenytoin-Gerot, Hidantomin, Gerot-epilan-D
Brand name mixture: Dilantin W Phenobarbital 30mg Cap(Phenobarbital + Phenytoin Sodium), Dilantin W Phenobarbital 15mg(Phenobarbital + Phenytoin Sodium)
Category: Anticonvulsants
CAS number: 57-41-0
Pharmacology
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.
Pharmacology:
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 ...
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Mechanism 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...
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Absorption: Bioavailability 70-100% oral, 24.4% for rectal and intravenous administration. Rapid rate of absorption with peak blood concentration expected in 1½ to 3 hours.
Protein binding: Highly protein bound, 90%
Biotransformation: Primarily hepatic
Route of elimination: Most of the drug is excreted in the bile as inactive metabolites which are then reabsorbed from the intestinal tract and excreted in the urine. Urinary excretion of phenytoin and its metabolites occurs partly with glomerular filtration but, more importantly, by tubular secretion.
Half Life: 22 hours (range of 7 to 42 hours)
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.
Affected organisms: Humans and other mammals
Interactions
Food interaction:
Avoid alcohol.
Take with food to increase bioavailability and reduce irritation.
Do not take calcium, aluminum, magnesium or Iron supplements within 2 hours of taking this medication.
Drug interaction:
PrednisoloneThe enzyme inducer, phenytoin, may decrease the effect of the corticosteroid, prednisolone.
Ethinyl EstradiolThis product may cause a slight decrease of contraceptive effect
TipranavirPhenytoin decreases the concentration of Tipranavir. Monitor for decreased Tipranavir efficacy.
SucralfateSucralfate decreases the effect of hydantoin
CapecitabineCapecitabine increases the effect of hydantoin
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