U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C15H12N2O2
Molecular Weight 252.268
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENYTOIN

SMILES

O=C1NC(=O)C(N1)(C2=CC=CC=C2)C3=CC=CC=C3

InChI

InChIKey=CXOFVDLJLONNDW-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C15H12N2O2
Molecular Weight 252.268
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

PubMed

PubMed

TitleDatePubMed
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
Cognitive dysfunction induced by phenytoin and valproate in rats: effect of nitric oxide.
1999 Jul
[Acute liver failure by diphenylhydantoin].
2000
Anticonvulsant-induced suppression of IFN-gamma production by lymphocytes obtained from cervical lymph nodes in glioma-bearing mice.
2000 Apr
[Phenytoin-induced hypersensitivity reaction with liver failure].
2000 Apr 13
Protection from phenytoin-induced cognitive deficit by Bacopa monniera, a reputed Indian nootropic plant.
2000 Aug
Acute fulminant hepatic failure in a woman treated with phenytoin and trimethoprim-sulfamethoxazole.
2000 Dec
Effects of anticonvulsants on local anaesthetic-induced neurotoxicity in rats.
2000 Feb
A multicenter randomized controlled trial on the clinical impact of therapeutic drug monitoring in patients with newly diagnosed epilepsy. The Italian TDM Study Group in Epilepsy.
2000 Feb
Felbamate in experimental model of status epilepticus.
2000 Feb
Immunolocalizaiton of c-Myc and bcl-2 proto-oncogene products in gingival hyperplasia induced by nifedipine and phenytoin.
2000 Jan
Phenytoin poisoning after using Chinese proprietary medicines.
2000 Jul
Cerebral edema with herniation during acetaminophen-induced fulminant hepatic failure.
2000 Jul
Refractory idiopathic absence status epilepticus: A probable paradoxical effect of phenytoin and carbamazepine.
2000 Jul
Incidence of intravenous site reactions in neurotrauma patients receiving valproate or phenytoin.
2000 Jun
Seizure-inducing paradoxical reaction to antiepileptic drugs.
2000 Jun
Gabapentin prophylaxis of clozapine-induced seizures.
2000 Mar
Purple glove syndrome caused by oral administration of phenytoin.
2000 Nov
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
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
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
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
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
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
Patents

Sample Use Guides

In Vivo Use Guide
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: Oral, Intravenous
In Vitro Use Guide
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.
Substance Class Chemical
Created
by admin
on Mon Oct 21 21:40:59 UTC 2019
Edited
by admin
on Mon Oct 21 21:40:59 UTC 2019
Record UNII
6158TKW0C5
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHENYTOIN
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INN   USAN  
Official Name English
PHENYTOIN [MI]
Common Name English
PHENYTOIN [USP-RS]
Common Name English
EPAMIN
Brand Name English
SM-88 COMPONENT PHENYTOIN
Code English
PHENYTOIN [WHO-DD]
Common Name English
PHENYTOIN [USAN]
Common Name English
LEPITOIN
Common Name English
PHENYTOIN [JAN]
Common Name English
DILANTIN
Brand Name English
NSC-8722
Code English
ZENTROPIL
Common Name English
PHENYTOIN [IARC]
Common Name English
5,5-DIPHENYLHYDANTOIN
Systematic Name English
PHENYTOIN [MART.]
Common Name English
PHENYTOIN [INN]
Common Name English
PHENYTOIN [HSDB]
Common Name English
PHENYTOIN [WHO-IP]
Common Name English
PHENYTOIN [VANDF]
Common Name English
PHENYTOIN [ORANGE BOOK]
Common Name English
DIPHENYLHYDANTOIN
Systematic Name English
PHENYTOINUM [WHO-IP LATIN]
Common Name English
PHENYTOIN [USP]
Common Name English
2,4-IMIDAZOLIDINEDIONE, 5,5-DIPHENYL-
Systematic Name English
PHENYTOIN [EP]
Common Name English
Classification Tree Code System Code
WHO-ESSENTIAL MEDICINES LIST 05
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
WHO-VATC QN03AB52
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
NDF-RT N0000008486
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
FDA ORPHAN DRUG 43490
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
WHO-VATC QN03AB02
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
LIVERTOX 775
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
NDF-RT N0000175753
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
CFR 21 CFR 862.3350
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
NCI_THESAURUS C264
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
IARC Phenytoin
WHO-ATC N03AB52
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
NCI_THESAURUS C93038
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
WHO-ATC N03AB02
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
Code System Code Type Description
NDF-RT
N0000190118
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
PRIMARY Cytochrome P450 3A Inducers [MoA]
ECHA (EC/EINECS)
200-328-6
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
PRIMARY
NDF-RT
N0000191267
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
PRIMARY Cytochrome P450 2D6 Inducers [MoA]
LactMed
57-41-0
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
PRIMARY
PUBCHEM
1775
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
PRIMARY
ChEMBL
CHEMBL16
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
PRIMARY
NDF-RT
N0000187063
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
PRIMARY Cytochrome P450 2C8 Inducers [MoA]
HSDB
57-41-0
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
PHENYTOIN
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
PRIMARY Description: A white, crystalline powder; odourless. Solubility: Practically insoluble in water; sparingly soluble in ethanol (~750 g/l) TS; slightly soluble in ether R. Category: Anticonvulsant. Storage: Phenytoin should be kept in a tightly closed container, protected from light. Definition: Phenytoin contains not less than 98.0% and not more than 101.0% of C15H12N2O2, calculated with reference to thedried substance.
MERCK INDEX
M8703
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
PRIMARY Merck Index
NDF-RT
N0000185607
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
PRIMARY Cytochrome P450 2C19 Inducers [MoA]
INN
416
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
PRIMARY
RXCUI
8183
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
PRIMARY RxNorm
CAS
57-41-0
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
PRIMARY
WIKIPEDIA
PHENYTOIN
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
PRIMARY
DRUG BANK
DB00252
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
PRIMARY
NDF-RT
N0000191266
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
PRIMARY Cytochrome P450 1A2 Inducers [MoA]
EPA CompTox
57-41-0
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
PRIMARY
EVMPD
SUB12211MIG
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
PRIMARY
NDF-RT
N0000185507
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
PRIMARY Cytochrome P450 2C9 Inducers [MoA]
NCI_THESAURUS
C741
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
PRIMARY
IUPHAR
2624
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
PRIMARY
NDF-RT
N0000187064
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
PRIMARY Cytochrome P450 2B6 Inducers [MoA]
MESH
D010672
Created by admin on Mon Oct 21 21:40:59 UTC 2019 , Edited by admin on Mon Oct 21 21:40:59 UTC 2019
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
TRANSPORTER -> SUBSTRATE
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> INDUCER
METABOLIC ENZYME -> INDUCER
METABOLIC ENZYME -> INDUCER
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
TRANSPORTER -> INDUCER
METABOLIC ENZYME -> INDUCER
POTENT
Related Record Type Details
METABOLITE -> PARENT
UGT1A isoforms (UGT1A1, UGT1A4, UGT1A6, and UGT1A9) are involved in the glucuronosyltransferase activity of 4?-HPPH in humans
MAJOR
PLASMA
METABOLITE INACTIVE -> PARENT
(1:1) R:S, by CYP2C19
Scientific Literature
METABOLITE INACTIVE -> PARENT
major metabolite, mainly by CYP2C9
MAJOR
Scientific Literature
Related Record Type Details
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 1.7
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 1.4
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC Population
PHARMACOKINETIC
Population
PHARMACOKINETIC
Population
PHARMACOKINETIC
Population
PHARMACOKINETIC
Population
PHARMACOKINETIC