Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C15H11N2O2.Na |
| Molecular Weight | 274.2498 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].O=C1NC(C(=O)[N-]1)(C2=CC=CC=C2)C3=CC=CC=C3
InChI
InChIKey=FJPYVLNWWICYDW-UHFFFAOYSA-M
InChI=1S/C15H12N2O2.Na/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);/q;+1/p-1
DescriptionCurator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020450s020lbl.pdf
Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020450s020lbl.pdf
Phenytoin is an anti-epileptic drug. Phenytoin has been used with much clinical success against all types of epileptiform seizures, except petit mal epilepsy. Phenytoin is a available for oral administration (tablets, capsules, suspension). CEREBYX® (fosphenytoin sodium injection) is a prodrug intended for parenteral administration; its active metabolite is phenytoin. CEREBYX should be used only when oral phenytoin administration is not possible. Although several potential targets for phenytoin action have been identified within the CNS (Na-K-ATPase, the GABAA receptor complex, ionotropic glutamate receptors, calcium channels and sigma binding sites) to date, though, the best evidence hinges on the inhibition of voltage-sensitive Na+ channels in the plasma membrane of neurons undergoing seizure activity.
CNS Activity
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL4187 |
10.4 µM [EC50] | ||
Target ID: CHEMBL5163 |
52.5 µM [EC50] | ||
Target ID: CHEMBL5202 |
20.0 µM [EC50] | ||
Target ID: CHEMBL1845 |
19.9 µM [EC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | DILANTIN-125 Approved UseDilantin (phenytoin) is indicated for the control of tonic-clonic (grand mal) and psychomotor (temporal lobe) seizures Launch Date1953 |
|||
| Primary | CEREBYX Approved UseCEREBYX is indicated for the control of generalized tonic-clonic status epilepticus and prevention and treatment of seizures occurring during neurosurgery. CEREBYX can also be substituted, short-term, for oral phenytoin. CEREBYX should be used only when oral phenytoin administration is not possible. CEREBYX must not be given orally. Launch Date1996 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.176 μg/mL |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHENYTOIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
32.172 μg × h/mL |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHENYTOIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
15.49 h |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHENYTOIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
600 mg single, oral Highest studied dose Dose: 600 mg Route: oral Route: single Dose: 600 mg Sources: |
unhealthy, 31 years n = 15 Health Status: unhealthy Condition: epilepsy Age Group: 31 years Sex: M+F Population Size: 15 Sources: |
|
20 g single, oral Overdose Dose: 20 g Route: oral Route: single Dose: 20 g Co-administed with:: glibenclamide(500 mg) Sources: |
unhealthy, 41 years n = 1 Health Status: unhealthy Age Group: 41 years Sex: F Population Size: 1 Sources: |
Other AEs: Sinus bradycardia, Hypotension... Other AEs: Sinus bradycardia (1 patient) Sources: Hypotension (severe, 1 patient) |
5 g single, oral Overdose |
unhealthy, 49 years n = 1 Health Status: unhealthy Age Group: 49 years Sex: M Population Size: 1 Sources: |
Other AEs: Acute respiratory failure... |
60 mg/kg multiple, intravenous (total) Overdose Dose: 60 mg/kg Route: intravenous Route: multiple Dose: 60 mg/kg Sources: |
unhealthy, 7 years n = 1 Health Status: unhealthy Age Group: 7 years Sex: M Population Size: 1 Sources: |
Other AEs: Encephalopathy... |
2 g single, oral Overdose Dose: 2 g Route: oral Route: single Dose: 2 g Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Other AEs: Nystagmus, Ataxia... Other AEs: Nystagmus (grade 5) Sources: Ataxia (grade 5) Dysarthria (grade 5) Tremor (grade 5) Hyperreflexia (grade 5) Lethargy (grade 5) Slurred speech (grade 5) Blurred vision (grade 5) Nausea (grade 5) Vomiting (grade 5) |
10 mg/kg single, intramuscular (starting) Dose: 10 mg/kg Route: intramuscular Route: single Dose: 10 mg/kg Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Other AEs: Hypotension, Cardiac arrhythmias... Other AEs: Hypotension (severe) Sources: Cardiac arrhythmias |
10 mg/kg single, intravenous (starting) Dose: 10 mg/kg Route: intravenous Route: single Dose: 10 mg/kg Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Other AEs: Hypotension, Cardiac arrhythmias... Other AEs: Hypotension (severe) Sources: Cardiac arrhythmias |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Sinus bradycardia | 1 patient | 20 g single, oral Overdose Dose: 20 g Route: oral Route: single Dose: 20 g Co-administed with:: glibenclamide(500 mg) Sources: |
unhealthy, 41 years n = 1 Health Status: unhealthy Age Group: 41 years Sex: F Population Size: 1 Sources: |
| Hypotension | severe, 1 patient | 20 g single, oral Overdose Dose: 20 g Route: oral Route: single Dose: 20 g Co-administed with:: glibenclamide(500 mg) Sources: |
unhealthy, 41 years n = 1 Health Status: unhealthy Age Group: 41 years Sex: F Population Size: 1 Sources: |
| Acute respiratory failure | 1 patient | 5 g single, oral Overdose |
unhealthy, 49 years n = 1 Health Status: unhealthy Age Group: 49 years Sex: M Population Size: 1 Sources: |
| Encephalopathy | 1 patient | 60 mg/kg multiple, intravenous (total) Overdose Dose: 60 mg/kg Route: intravenous Route: multiple Dose: 60 mg/kg Sources: |
unhealthy, 7 years n = 1 Health Status: unhealthy Age Group: 7 years Sex: M Population Size: 1 Sources: |
| Ataxia | grade 5 | 2 g single, oral Overdose Dose: 2 g Route: oral Route: single Dose: 2 g Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
| Blurred vision | grade 5 | 2 g single, oral Overdose Dose: 2 g Route: oral Route: single Dose: 2 g Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
| Dysarthria | grade 5 | 2 g single, oral Overdose Dose: 2 g Route: oral Route: single Dose: 2 g Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
| Hyperreflexia | grade 5 | 2 g single, oral Overdose Dose: 2 g Route: oral Route: single Dose: 2 g Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
| Lethargy | grade 5 | 2 g single, oral Overdose Dose: 2 g Route: oral Route: single Dose: 2 g Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
| Nausea | grade 5 | 2 g single, oral Overdose Dose: 2 g Route: oral Route: single Dose: 2 g Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
| Nystagmus | grade 5 | 2 g single, oral Overdose Dose: 2 g Route: oral Route: single Dose: 2 g Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
| Slurred speech | grade 5 | 2 g single, oral Overdose Dose: 2 g Route: oral Route: single Dose: 2 g Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
| Tremor | grade 5 | 2 g single, oral Overdose Dose: 2 g Route: oral Route: single Dose: 2 g Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
| Vomiting | grade 5 | 2 g single, oral Overdose Dose: 2 g Route: oral Route: single Dose: 2 g Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
| Cardiac arrhythmias | 10 mg/kg single, intramuscular (starting) Dose: 10 mg/kg Route: intramuscular Route: single Dose: 10 mg/kg Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
|
| Hypotension | severe | 10 mg/kg single, intramuscular (starting) Dose: 10 mg/kg Route: intramuscular Route: single Dose: 10 mg/kg Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
| Cardiac arrhythmias | 10 mg/kg single, intravenous (starting) Dose: 10 mg/kg Route: intravenous Route: single Dose: 10 mg/kg Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
|
| Hypotension | severe | 10 mg/kg single, intravenous (starting) Dose: 10 mg/kg Route: intravenous Route: single Dose: 10 mg/kg Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| no | ||||
Page: 6.0 |
weak | |||
Page: 7.0 |
yes [IC50 145 uM] | |||
Page: 7.0 |
yes [IC50 280 uM] | |||
Page: 7.0 |
yes [IC50 607 uM] | |||
| yes | ||||
| yes | likely (co-administration study) Comment: See https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/084427s042lbl.pdf#page=10 |
|||
| yes | likely (co-administration study) Comment: See https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/084427s042lbl.pdf#page=10 |
|||
Page: 46.0 |
yes | likely (co-administration study) Comment: See https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/084427s042lbl.pdf#page=11 Page: 46.0 |
||
| yes | likely (co-administration study) Comment: See https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/084427s042lbl.pdf#page=9 |
|||
| yes | likely (co-administration study) Comment: See https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/084427s042lbl.pdf#page=11 |
|||
| yes | yes (co-administration study) Comment: mean AUC(0-24) of losartan was insignificantly increased by 17% when losartan was coadministered with phenytoin. See more on https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/084427s042lbl.pdf#page=9 |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 6.0 |
no | |||
| yes | ||||
Page: 7.0 |
yes | |||
| yes | likely (co-administration study) Comment: See https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/084427s042lbl.pdf#page=9 |
|||
| yes | yes (co-administration study) Comment: Coadministration of losartan had no effect on the pharmacokinetics of phenytoin. See more on https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/084427s042lbl.pdf#page8 Page: 8.0 |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Harmful effect of megadoses of vitamins: electroencephalogram abnormalities and seizures induced by intravenous folate in drug-treated epileptics. | 1975 Jan |
|
| The influence of aldosterone and anticonvulsant drugs on electroencephalographic and clinical disturbances induced by the spirolactone derivative, potassium canrenoate. | 1975 Jan |
|
| Procainamide and phenytoin. Comparative study of their antiarrhythmic effects at apparent therapeutic plasma levels. | 1975 Jul |
|
| Anticonvulsant-induced suppression of IFN-gamma production by lymphocytes obtained from cervical lymph nodes in glioma-bearing mice. | 2000 Apr |
|
| Acute fulminant hepatic failure in a woman treated with phenytoin and trimethoprim-sulfamethoxazole. | 2000 Dec |
|
| Phenytoin, midazolam, and naloxone protect against fentanyl-induced brain damage in rats. | 2000 Dec |
|
| Phenytoin poisoning after using Chinese proprietary medicines. | 2000 Jul |
|
| Purple glove syndrome caused by oral administration of phenytoin. | 2000 Nov |
|
| Effects of combined administration of zonisamide and valproic acid or phenytoin to nitric oxide production, monoamines and zonisamide concentrations in the brain of seizure-susceptible EL mice. | 2000 Sep 15 |
|
| Drugs for discoid lupus erythematosus. | 2001 |
|
| II. An altered proliferation response due to the anticonvulsant phenytoin (PHT) in epileptic patients. | 2001 |
|
| I. The modulatory effect in genotoxic responses due to age and duration of PHT-therapy in epileptic patients. | 2001 |
|
| Evaluation of the neuroprotective effects of sodium channel blockers after spinal cord injury: improved behavioral and neuroanatomical recovery with riluzole. | 2001 Apr |
|
| Performance characteristics of four free phenytoin immunoassays. | 2001 Apr |
|
| Rocuronium-induced neuromuscular blockade is affected by chronic phenytoin therapy. | 2001 Apr |
|
| Stereoselective determination of p-hydroxyphenyl-phenylhydantoin enantiomers in rat liver microsomal incubates by reversed-phase high-performance liquid chromatography using beta-cyclodextrin as chiral mobile phase additives. | 2001 Apr |
|
| Decreases in phenytoin hydroxylation activities catalyzed by liver microsomal cytochrome P450 enzymes in phenytoin-treated rats. | 2001 Apr |
|
| Inhibition of phenytoin hydroxylation in human liver microsomes by several selective serotonin re-uptake inhibitors. | 2001 Apr |
|
| The teratogenicity of anticonvulsant drugs. | 2001 Apr 12 |
|
| Nitroso-urea-cisplatin-based chemotherapy associated with valproate: increase of haematologic toxicity. | 2001 Feb |
|
| Determination of the antiepileptics vigabatrin and gabapentin in dosage forms and biological fluids using Hantzsch reaction. | 2001 Feb |
|
| Refractory idiopathic status epilepticus. | 2001 Feb |
|
| Cardiac arrest after fast intravenous infusion of phenytoin mistaken for fosphenytoin. | 2001 Feb |
|
| Antiepileptic drug withdrawal in patients with temporal lobe epilepsy undergoing presurgical video-EEG monitoring. | 2001 Feb |
|
| Fosphenytoin: pharmacokinetics and tolerance of intramuscular loading doses. | 2001 Feb |
|
| Glutamate receptor antagonists differentially affect the protective activity of conventional antiepileptics against amygdala-kindled seizures in rats. | 2001 Feb |
|
| Phenytoin intoxication induced by fluvoxamine. | 2001 Feb |
|
| The effects of concomitant phenytoin administration on the steady-state pharmacokinetics of quetiapine. | 2001 Feb |
|
| Rufinamide: a double-blind, placebo-controlled proof of principle trial in patients with epilepsy. | 2001 Feb |
|
| Possible function of astrocyte cytochrome P450 in control of xenobiotic phenytoin in the brain: in vitro studies on murine astrocyte primary cultures. | 2001 Feb |
|
| [Maintenance dose requirement for phenytoin is lowered in genetically impaired drug metabolism independent of concommitant use of other antiepileptics]. | 2001 Feb 17 |
|
| [Febrile convulsions, Treatment and prognosis]. | 2001 Feb 19 |
|
| Interferon-alpha2a and 13-cis-retinoic acid with radiation treatment for high-grade glioma. | 2001 Jan |
|
| Inhibition of human cytochrome P450 isoforms by nonnucleoside reverse transcriptase inhibitors. | 2001 Jan |
|
| Electrophysiological and pharmacological properties of the human brain type IIA Na+ channel expressed in a stable mammalian cell line. | 2001 Jan |
|
| Hair analysis for pharmaceutical drugs. I. Effective extraction and determination of phenobarbital, phenytoin and their major metabolites in rat and human hair. | 2001 Jan |
|
| Ritonavir-induced carbamazepine toxicity. | 2001 Jan |
|
| Treatment of nonfebrile status epilepticus in Rochester, Minn, from 1965 through 1984. | 2001 Jan |
|
| Effects of antiepileptic drugs on rat platelet aggregation: ex vivo and in vitro study. | 2001 Jan |
|
| Effects of phenytoin on glutathione status and oxidative stress biomarker gene mRNA levels in cultured precision human liver slices. | 2001 Jan |
|
| Successful treatment of antiepileptic drug hypersensitivity syndrome with intravenous immune globulin. | 2001 Jan |
|
| [Lamotrigine in refractory partial and general epilepsies]. | 2001 Jan 1-15 |
|
| Myotoxicity studies of injectable biodegradable in-situ forming drug delivery systems. | 2001 Jan 5 |
|
| N6-cyclohexyladenosine and 3-(2-carboxypiperazine-4-yl)-1-propenyl-1-phosphonic acid enhance the effect of antiepileptic drugs against induced seizures in mice. | 2001 Jan-Apr |
|
| Volume-selective proton MR spectroscopy for in-vitro quantification of anticonvulsants. | 2001 Mar |
|
| Fosphenytoin in infants of extremely low birth weight. | 2001 Mar |
|
| Influence of retigabine on the anticonvulsant activity of some antiepileptic drugs against audiogenic seizures in DBA/2 mice. | 2001 Mar |
|
| Phenytoin-induced cleft palate: evidence for embryonic cardiac bradyarrhythmia due to inhibition of delayed rectifier K+ channels resulting in hypoxia-reoxygenation damage. | 2001 Mar |
|
| Interaction of plasma proteins with cytochromes P450 mediated metabolic reactions: inhibition by human serum albumin and alpha-globulins of the debrisoquine 4-hydroxylation (CYP2D) in liver microsomes of human, hamster and rat. | 2001 Mar 8 |
|
| Efficacy of levetiracetam versus fosphenytoin for the recurrence of seizures after status epilepticus. | 2017 Jun |
Sample Use Guides
Dilantin-125® (Phenytoin Oral Suspension, USP), each 5 ml of suspension contains 125 mg of phenytoin: Patients who have received no previous treatment may be started on one teaspoonful (5 mL) of Dilantin-125 Suspension three times daily, and the dose is then adjusted to suit individual requirements. An increase to five teaspoonfuls daily may be made, if necessary.
CEREBYX® (fosphenytoin sodium injection) is a prodrug intended for parenteral administration; its active metabolite is phenytoin. 1.5 mg of fosphenytoin sodium is equivalent to
1 mg phenytoin sodium, and is referred to as 1 mg phenytoin sodium equivalents (PE). CEREBYX should be used only when oral phenytoin administration is not possible.
Dosage (Status Epilepticus): The loading dose of CEREBYX is 15 to 20 mg PE/kg administered at 100 to 150 mg PE/min.
Route of Administration:
Other
Exposure of human adult keratinocytes (HaCaT cells) for 48 h to alkyd nanoemulsions producing phenytoin concentrations of 3.125-200 μg/mL resulted in relative cell viability readings using tetrazolium dye 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide of 100% confirming nontoxicity and suggesting cell proliferation activity.
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| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
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NCI_THESAURUS |
C264
Created by
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NCI_THESAURUS |
C93038
Created by
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CFR |
21 CFR 522.900
Created by
admin on Fri Dec 15 16:38:53 GMT 2023 , Edited by admin on Fri Dec 15 16:38:53 GMT 2023
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| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
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4182431BJH
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PRIMARY | |||
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657302
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71227
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630-93-3
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4182431BJH
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DBSALT000139
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SUB03787MIG
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PHENYTOIN SODIUM
Created by
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PRIMARY | Description: A white powder; odourless. Solubility: Soluble in water, giving a slightly turbid solution owing to partial hydrolysis; soluble in ethanol (~750 g/l) TS; practicallyinsoluble in ether R. Category: Anticonvulsant. Storage: Phenytoin sodium should be kept in a tightly closed container. Additional information: Phenytoin sodium is somewhat hygroscopic and on exposure to air gradually absorbs carbon dioxide. Definition: Phenytoin sodium contains not less than 98.5% and not more than 101.0% of C15H11N2NaO2, calculated withreference to the dried substance. | ||
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1535507
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211-148-2
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CHEMBL16
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C48011
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100000089972
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m8703
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757274
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ACTIVE MOIETY
SUBSTANCE RECORD
