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

Details

Stereochemistry ACHIRAL
Molecular Formula C15H12N2O2
Molecular Weight 252.2685
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENYTOIN

SMILES

c1ccc(cc1)C2(c3ccccc3)C(=NC(=N2)O)O

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

-5.36025596E11
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

8.3911678E11
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
Reversible renal failure and myositis caused by phenytoin hypersensitivity.
1976 Dec 13
Psychopharmacological studies on (--)-nuciferine and its Hofmann degradation product atherosperminine.
1978 Sep 15
A common mutation in the methylenetetrahydrofolate reductase gene is a determinant of hyperhomocysteinemia in epileptic patients receiving anticonvulsants.
1999 Aug
Neurotoxic effects of phenytoin on postnatal mouse brain development following neonatal administration.
1999 Jan-Feb
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
[Atrioventricular junctional arrhythmia due to oral phenytoin intoxication].
1999 Mar 15
Developmental effects of phenytoin may differ depending on sex of offspring.
1999 Mar-Apr
Frequency of cytochrome P450 CYP2C9 variants in a Turkish population and functional relevance for phenytoin.
1999 Sep
Felbamate in experimental model of status epilepticus.
2000 Feb
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
Temporal and spatial expression of Hoxa-2 during murine palatogenesis.
2000 Jun
Activation of cytochrome P450 gene expression in the rat brain by phenobarbital-like inducers.
2000 Sep
Drugs for discoid lupus erythematosus.
2001
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
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
The effects of concomitant phenytoin administration on the steady-state pharmacokinetics of quetiapine.
2001 Feb
Inhibition of human cytochrome P450 isoforms by nonnucleoside reverse transcriptase inhibitors.
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
Volume-selective proton MR spectroscopy for in-vitro quantification of anticonvulsants.
2001 Mar
Influence of retigabine on the anticonvulsant activity of some antiepileptic drugs against audiogenic seizures in DBA/2 mice.
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 [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
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 [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
PHENYTOIN [USP]
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 Jun 25 20:53:12 UTC 2021 , Edited by admin on Fri Jun 25 20:53:12 UTC 2021
WHO-VATC QN03AB52
Created by admin on Fri Jun 25 20:53:12 UTC 2021 , Edited by admin on Fri Jun 25 20:53:12 UTC 2021
NDF-RT N0000008486
Created by admin on Fri Jun 25 20:53:11 UTC 2021 , Edited by admin on Fri Jun 25 20:53:11 UTC 2021
FDA ORPHAN DRUG 43490
Created by admin on Fri Jun 25 20:53:11 UTC 2021 , Edited by admin on Fri Jun 25 20:53:11 UTC 2021
WHO-VATC QN03AB02
Created by admin on Fri Jun 25 20:53:12 UTC 2021 , Edited by admin on Fri Jun 25 20:53:12 UTC 2021
LIVERTOX 775
Created by admin on Fri Jun 25 20:53:11 UTC 2021 , Edited by admin on Fri Jun 25 20:53:11 UTC 2021
NDF-RT N0000175753
Created by admin on Fri Jun 25 20:53:11 UTC 2021 , Edited by admin on Fri Jun 25 20:53:11 UTC 2021
CFR 21 CFR 862.3350
Created by admin on Fri Jun 25 20:53:11 UTC 2021 , Edited by admin on Fri Jun 25 20:53:11 UTC 2021
NCI_THESAURUS C264
Created by admin on Fri Jun 25 20:53:11 UTC 2021 , Edited by admin on Fri Jun 25 20:53:11 UTC 2021
IARC Phenytoin
WHO-ATC N03AB52
Created by admin on Fri Jun 25 20:53:11 UTC 2021 , Edited by admin on Fri Jun 25 20:53:11 UTC 2021
NCI_THESAURUS C93038
Created by admin on Fri Jun 25 20:53:11 UTC 2021 , Edited by admin on Fri Jun 25 20:53:11 UTC 2021
WHO-ATC N03AB02
Created by admin on Fri Jun 25 20:53:11 UTC 2021 , Edited by admin on Fri Jun 25 20:53:11 UTC 2021
Code System Code Type Description
NDF-RT
N0000190118
Created by admin on Fri Jun 25 20:53:11 UTC 2021 , Edited by admin on Fri Jun 25 20:53:11 UTC 2021
PRIMARY Cytochrome P450 3A Inducers [MoA]
ECHA (EC/EINECS)
200-328-6
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PRIMARY
NDF-RT
N0000191267
Created by admin on Fri Jun 25 20:53:11 UTC 2021 , Edited by admin on Fri Jun 25 20:53:11 UTC 2021
PRIMARY Cytochrome P450 2D6 Inducers [MoA]
PUBCHEM
1775
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PRIMARY
ChEMBL
CHEMBL16
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PRIMARY
NDF-RT
N0000187063
Created by admin on Fri Jun 25 20:53:11 UTC 2021 , Edited by admin on Fri Jun 25 20:53:11 UTC 2021
PRIMARY Cytochrome P450 2C8 Inducers [MoA]
LACTMED
Phenytoin
Created by admin on Fri Jun 25 20:53:11 UTC 2021 , Edited by admin on Fri Jun 25 20:53:11 UTC 2021
PRIMARY
HSDB
3160
Created by admin on Fri Jun 25 20:53:11 UTC 2021 , Edited by admin on Fri Jun 25 20:53:11 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
PHENYTOIN
Created by admin on Fri Jun 25 20:53:12 UTC 2021 , Edited by admin on Fri Jun 25 20:53:12 UTC 2021
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
Created by admin on Fri Jun 25 20:53:11 UTC 2021 , Edited by admin on Fri Jun 25 20:53:11 UTC 2021
PRIMARY RxNorm
CAS
57-41-0
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PRIMARY
WIKIPEDIA
PHENYTOIN
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PRIMARY
USP_CATALOG
1535008
Created by admin on Fri Jun 25 20:53:11 UTC 2021 , Edited by admin on Fri Jun 25 20:53:11 UTC 2021
PRIMARY USP-RS
DRUG BANK
DB00252
Created by admin on Fri Jun 25 20:53:11 UTC 2021 , Edited by admin on Fri Jun 25 20:53:11 UTC 2021
PRIMARY
NDF-RT
N0000191266
Created by admin on Fri Jun 25 20:53:11 UTC 2021 , Edited by admin on Fri Jun 25 20:53:11 UTC 2021
PRIMARY Cytochrome P450 1A2 Inducers [MoA]
EPA CompTox
57-41-0
Created by admin on Fri Jun 25 20:53:11 UTC 2021 , Edited by admin on Fri Jun 25 20:53:11 UTC 2021
PRIMARY
EVMPD
SUB12211MIG
Created by admin on Fri Jun 25 20:53:11 UTC 2021 , Edited by admin on Fri Jun 25 20:53:11 UTC 2021
PRIMARY
NDF-RT
N0000185507
Created by admin on Fri Jun 25 20:53:11 UTC 2021 , Edited by admin on Fri Jun 25 20:53:11 UTC 2021
PRIMARY Cytochrome P450 2C9 Inducers [MoA]
NCI_THESAURUS
C741
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PRIMARY
DRUG CENTRAL
2152
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PRIMARY
IUPHAR
2624
Created by admin on Fri Jun 25 20:53:11 UTC 2021 , Edited by admin on Fri Jun 25 20:53:11 UTC 2021
PRIMARY
FDA UNII
6158TKW0C5
Created by admin on Fri Jun 25 20:53:11 UTC 2021 , Edited by admin on Fri Jun 25 20:53:11 UTC 2021
PRIMARY
NDF-RT
N0000187064
Created by admin on Fri Jun 25 20:53:11 UTC 2021 , Edited by admin on Fri Jun 25 20:53:11 UTC 2021
PRIMARY Cytochrome P450 2B6 Inducers [MoA]
MESH
D010672
Created by admin on Fri Jun 25 20:53:11 UTC 2021 , Edited by admin on Fri Jun 25 20:53:11 UTC 2021
PRIMARY