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 NONE
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

Description
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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DILANTIN-125

Approved Use

Dilantin (phenytoin) is indicated for the control of tonic-clonic (grand mal) and psychomotor (temporal lobe) seizures

Launch Date

1953
Primary
CEREBYX

Approved Use

CEREBYX 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 Date

1996
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse events​
600 mg single, oral
Highest studied dose
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)
Hypotension (severe, 1 patient)
Sources:
5 g single, oral
Overdose
Dose: 5 g
Route: oral
Route: single
Dose: 5 g
Sources:
unhealthy, 49 years
n = 1
Health Status: unhealthy
Age Group: 49 years
Sex: M
Population Size: 1
Sources:
Other AEs: Acute respiratory failure...
Other AEs:
Acute respiratory failure (1 patient)
Sources:
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...
Other AEs:
Encephalopathy (1 patient)
Sources:
2 g single, oral
Overdose
Dose: 2 g
Route: oral
Route: single
Dose: 2 g
Sources:
unhealthy, adult
Other AEs: Nystagmus, Ataxia...
Other AEs:
Nystagmus (grade 5)
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)
Sources:
10 mg/kg single, intramuscular (starting)
Dose: 10 mg/kg
Route: intramuscular
Route: single
Dose: 10 mg/kg
Sources:
unhealthy, adult
Other AEs: Hypotension, Cardiac arrhythmias...
Other AEs:
Hypotension (severe)
Cardiac arrhythmias
Sources:
10 mg/kg single, intravenous (starting)
Dose: 10 mg/kg
Route: intravenous
Route: single
Dose: 10 mg/kg
Sources:
unhealthy, adult
Other AEs: Hypotension, Cardiac arrhythmias...
Other AEs:
Hypotension (severe)
Cardiac arrhythmias
Sources:
AEs

AEs

AESignificanceDosePopulation
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
Dose: 5 g
Route: oral
Route: single
Dose: 5 g
Sources:
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
Blurred vision grade 5
2 g single, oral
Overdose
Dose: 2 g
Route: oral
Route: single
Dose: 2 g
Sources:
unhealthy, adult
Dysarthria grade 5
2 g single, oral
Overdose
Dose: 2 g
Route: oral
Route: single
Dose: 2 g
Sources:
unhealthy, adult
Hyperreflexia grade 5
2 g single, oral
Overdose
Dose: 2 g
Route: oral
Route: single
Dose: 2 g
Sources:
unhealthy, adult
Lethargy grade 5
2 g single, oral
Overdose
Dose: 2 g
Route: oral
Route: single
Dose: 2 g
Sources:
unhealthy, adult
Nausea grade 5
2 g single, oral
Overdose
Dose: 2 g
Route: oral
Route: single
Dose: 2 g
Sources:
unhealthy, adult
Nystagmus grade 5
2 g single, oral
Overdose
Dose: 2 g
Route: oral
Route: single
Dose: 2 g
Sources:
unhealthy, adult
Slurred speech grade 5
2 g single, oral
Overdose
Dose: 2 g
Route: oral
Route: single
Dose: 2 g
Sources:
unhealthy, adult
Tremor grade 5
2 g single, oral
Overdose
Dose: 2 g
Route: oral
Route: single
Dose: 2 g
Sources:
unhealthy, adult
Vomiting grade 5
2 g single, oral
Overdose
Dose: 2 g
Route: oral
Route: single
Dose: 2 g
Sources:
unhealthy, adult
Cardiac arrhythmias
10 mg/kg single, intramuscular (starting)
Dose: 10 mg/kg
Route: intramuscular
Route: single
Dose: 10 mg/kg
Sources:
unhealthy, adult
Hypotension severe
10 mg/kg single, intramuscular (starting)
Dose: 10 mg/kg
Route: intramuscular
Route: single
Dose: 10 mg/kg
Sources:
unhealthy, adult
Cardiac arrhythmias
10 mg/kg single, intravenous (starting)
Dose: 10 mg/kg
Route: intravenous
Route: single
Dose: 10 mg/kg
Sources:
unhealthy, adult
Hypotension severe
10 mg/kg single, intravenous (starting)
Dose: 10 mg/kg
Route: intravenous
Route: single
Dose: 10 mg/kg
Sources:
unhealthy, adult
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
weak
yes [IC50 145 uM]
yes [IC50 280 uM]
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
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

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
yes
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

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
The influence of aldosterone and anticonvulsant drugs on electroencephalographic and clinical disturbances induced by the spirolactone derivative, potassium canrenoate.
1975 Jan
Diphenylhydantoin teratogenicity: ocular manifestations and related deformities.
1978 May-Jun
Spasticity due to phenytoin toxicity.
1979 Mar 10
Paradoxical seizures in phenytoin toxicity.
1999 Apr
A common mutation in the methylenetetrahydrofolate reductase gene is a determinant of hyperhomocysteinemia in epileptic patients receiving anticonvulsants.
1999 Aug
Expression and inducibility of the human bilirubin UDP-glucuronosyltransferase UGT1A1 in liver and cultured primary hepatocytes: evidence for both genetic and environmental influences.
1999 Aug
Cognitive dysfunction induced by phenytoin and valproate in rats: effect of nitric oxide.
1999 Jul
Distinct features of seizures induced by cocaine and amphetamine analogs.
1999 Jul 21
Dyskinesia induced by phenytoin.
1999 Jun
Ephedrine-induced complete atrioventricular block with ventricular asystole during rapid concomitant phenytoin infusion: a case report.
1999 Mar
Retro-peritoneal cystic lymphangioma in association with fetal hydantoin syndrome.
1999 Mar-Apr
Fetal hydantoin syndrome with rheumatic valvular heart disease.
1999 Mar-Apr
Tuberous sclerosis associated with MDR1 gene expression and drug-resistant epilepsy.
1999 Oct
Side effects and mortality associated with use of phenytoin for early posttraumatic seizure prophylaxis.
1999 Oct
Incidence and clinical consequence of the purple glove syndrome in patients receiving intravenous phenytoin.
1999 Oct 22
Fetal anticonvulsant syndrome and mutation in the maternal MTHFR gene.
1999 Sep
Frequency of cytochrome P450 CYP2C9 variants in a Turkish population and functional relevance for phenytoin.
1999 Sep
[Phenytoin-induced hypersensitivity reaction with liver failure].
2000 Apr 13
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
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
Sodium valproate inhibits production of TNF-alpha and IL-6 and activation of NF-kappaB.
2000 Feb 28
Images in clinical medicine. Gingival hyperplasia induced by phenytoin.
2000 Feb 3
Immunolocalizaiton of c-Myc and bcl-2 proto-oncogene products in gingival hyperplasia induced by nifedipine and phenytoin.
2000 Jan
An embryoprotective role for glucose-6-phosphate dehydrogenase in developmental oxidative stress and chemical teratogenesis.
2000 Jan
Phenytoin poisoning after using Chinese proprietary medicines.
2000 Jul
Refractory idiopathic absence status epilepticus: A probable paradoxical effect of phenytoin and carbamazepine.
2000 Jul
Phenytoin and cyclosporin A suppress the expression of MMP-1, TIMP-1, and cathepsin L, but not cathepsin B in cultured gingival fibroblasts.
2000 Jun
Catalytic activity of three variants (Ile, Leu, and Thr) at amino acid residue 359 in human CYP2C9 gene and simultaneous detection using single-strand conformation polymorphism analysis.
2000 Jun
Seizure-inducing paradoxical reaction to antiepileptic drugs.
2000 Jun
Temporal and spatial expression of Hoxa-2 during murine palatogenesis.
2000 Jun
Gabapentin prophylaxis of clozapine-induced seizures.
2000 Mar
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
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
The teratogenicity of anticonvulsant drugs.
2001 Apr 12
Refractory idiopathic status epilepticus.
2001 Feb
Antiepileptic drug withdrawal in patients with temporal lobe epilepsy undergoing presurgical video-EEG monitoring.
2001 Feb
Phenytoin intoxication induced by fluvoxamine.
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
Inhibition of human cytochrome P450 isoforms by nonnucleoside reverse transcriptase inhibitors.
2001 Jan
Ritonavir-induced carbamazepine toxicity.
2001 Jan
Effects of antiepileptic drugs on rat platelet aggregation: ex vivo and in vitro study.
2001 Jan
Fosphenytoin in infants of extremely low birth weight.
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
Patents

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.
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 [USAN]
Common Name English
LEPITOIN
Common Name English
PHENYTOIN [JAN]
Common Name English
PHENYTOIN [USP IMPURITY]
Common Name English
DILANTIN
Brand Name English
NSC-8722
Code English
PHENYTOIN [EP MONOGRAPH]
Common Name English
ZENTROPIL
Common Name English
PHENYTOIN [IARC]
Common Name English
PHENYTOIN [USP MONOGRAPH]
Common Name English
5,5-Diphenylhydantoin
Systematic Name English
PHENYTOIN [MART.]
Common Name English
Phenytoin [WHO-DD]
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
PHENYTOINUM [WHO-IP LATIN]
Common Name English
2,4-IMIDAZOLIDINEDIONE, 5,5-DIPHENYL-
Systematic Name English
Classification Tree Code System Code
WHO-ESSENTIAL MEDICINES LIST 05
Created by admin on Fri Dec 15 14:59:53 GMT 2023 , Edited by admin on Fri Dec 15 14:59:53 GMT 2023
WHO-VATC QN03AB52
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NDF-RT N0000008486
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FDA ORPHAN DRUG 43490
Created by admin on Fri Dec 15 14:59:53 GMT 2023 , Edited by admin on Fri Dec 15 14:59:53 GMT 2023
WHO-VATC QN03AB02
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LIVERTOX NBK548889
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NDF-RT N0000175753
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CFR 21 CFR 862.3350
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NCI_THESAURUS C264
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IARC Phenytoin
WHO-ATC N03AB52
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NCI_THESAURUS C93038
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WHO-ATC N03AB02
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Code System Code Type Description
DAILYMED
6158TKW0C5
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PRIMARY
NSC
8722
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PRIMARY
NDF-RT
N0000190118
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PRIMARY Cytochrome P450 3A Inducers [MoA]
ECHA (EC/EINECS)
200-328-6
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PRIMARY
NDF-RT
N0000191267
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PRIMARY Cytochrome P450 2D6 Inducers [MoA]
RS_ITEM_NUM
1535008
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PRIMARY
PUBCHEM
1775
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PRIMARY
SMS_ID
100000092104
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PRIMARY
ChEMBL
CHEMBL16
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PRIMARY
NDF-RT
N0000187063
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PRIMARY Cytochrome P450 2C8 Inducers [MoA]
CHEBI
8107
Created by admin on Fri Dec 15 14:59:53 GMT 2023 , Edited by admin on Fri Dec 15 14:59:53 GMT 2023
PRIMARY
LACTMED
Phenytoin
Created by admin on Fri Dec 15 14:59:53 GMT 2023 , Edited by admin on Fri Dec 15 14:59:53 GMT 2023
PRIMARY
HSDB
3160
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PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
PHENYTOIN
Created by admin on Fri Dec 15 14:59:53 GMT 2023 , Edited by admin on Fri Dec 15 14:59:53 GMT 2023
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
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PRIMARY Merck Index
NDF-RT
N0000185607
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PRIMARY Cytochrome P450 2C19 Inducers [MoA]
INN
416
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PRIMARY
RXCUI
8183
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PRIMARY RxNorm
CAS
57-41-0
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PRIMARY
WIKIPEDIA
PHENYTOIN
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PRIMARY
DRUG BANK
DB00252
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PRIMARY
NDF-RT
N0000191266
Created by admin on Fri Dec 15 14:59:53 GMT 2023 , Edited by admin on Fri Dec 15 14:59:53 GMT 2023
PRIMARY Cytochrome P450 1A2 Inducers [MoA]
EPA CompTox
DTXSID8020541
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PRIMARY
EVMPD
SUB12211MIG
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PRIMARY
NDF-RT
N0000185507
Created by admin on Fri Dec 15 14:59:53 GMT 2023 , Edited by admin on Fri Dec 15 14:59:53 GMT 2023
PRIMARY Cytochrome P450 2C9 Inducers [MoA]
NCI_THESAURUS
C741
Created by admin on Fri Dec 15 14:59:53 GMT 2023 , Edited by admin on Fri Dec 15 14:59:53 GMT 2023
PRIMARY
DRUG CENTRAL
2152
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PRIMARY
IUPHAR
2624
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PRIMARY
FDA UNII
6158TKW0C5
Created by admin on Fri Dec 15 14:59:53 GMT 2023 , Edited by admin on Fri Dec 15 14:59:53 GMT 2023
PRIMARY
NDF-RT
N0000187064
Created by admin on Fri Dec 15 14:59:53 GMT 2023 , Edited by admin on Fri Dec 15 14:59:53 GMT 2023
PRIMARY Cytochrome P450 2B6 Inducers [MoA]
MESH
D010672
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PRIMARY