PHENYTOIN

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Trade Names
Synonyms
Status
Molecule Category Free-form
ATC N03AB02
UNII 6158TKW0C5
EPA CompTox DTXSID8020541

Structure

InChI Key CXOFVDLJLONNDW-UHFFFAOYSA-N
Smiles O=C1NC(=O)C(c2ccccc2)(c2ccccc2)N1
InChI
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)

Physicochemical Descriptors

Property Name Value
Molecular Formula C15H12N2O2
Molecular Weight 252.27
AlogP 1.97
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 2.0
Polar Surface Area 61.69
Molecular species ACID
Aromatic Rings 2.0
Heavy Atoms 19.0

Metabolites Network

visNetwork

Bioactivity

Mechanism of Action Action Reference
Sodium channel alpha subunit blocker BLOCKER PubMed PubMed FDA
Protein: Sodium channel alpha subunit
Description: Sodium channel protein type 1 subunit alpha
Organism : Homo sapiens
P35498 ENSG00000144285
Protein: Sodium channel alpha subunit
Description: Sodium channel protein type 4 subunit alpha
Organism : Homo sapiens
P35499 ENSG00000007314
Protein: Sodium channel alpha subunit
Description: Sodium channel protein type 5 subunit alpha
Organism : Homo sapiens
Q14524 ENSG00000183873
Protein: Sodium channel alpha subunit
Description: Sodium channel protein type 9 subunit alpha
Organism : Homo sapiens
Q15858 ENSG00000169432
Protein: Sodium channel alpha subunit
Description: Sodium channel protein type 2 subunit alpha
Organism : Homo sapiens
Q99250 ENSG00000136531
Protein: Sodium channel alpha subunit
Description: Sodium channel protein type 3 subunit alpha
Organism : Homo sapiens
Q9NY46 ENSG00000153253
Protein: Sodium channel alpha subunit
Description: Sodium channel protein type 11 subunit alpha
Organism : Homo sapiens
Q9UI33 ENSG00000168356
Protein: Sodium channel alpha subunit
Description: Sodium channel protein type 8 subunit alpha
Organism : Homo sapiens
Q9UQD0 ENSG00000196876
Protein: Sodium channel alpha subunit
Description: Sodium channel protein type 10 subunit alpha
Organism : Homo sapiens
Q9Y5Y9 ENSG00000185313
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- - - 6000-10000 -
Enzyme Hydrolase
- - - - 11
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- 100000 - - 9-40
Ion channel Voltage-gated ion channel Voltage-gated calcium channel
- 21900 - - 58
Ion channel Voltage-gated ion channel Voltage-gated sodium channel
- 40000-40000 - 24000 10-21
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 11
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - -
Assay Description Organism Bioactivity Reference
Antiepileptic (anticonvulsant) activity in mice through maximal electroshock seizure (MES) assay Mus musculus 9.5 mg kg-1
Inhibition of binding of Batrachotoxinin [3H]BTX-B to high affinity sites on voltage dependent sodium channels in a vesicular preparation from guinea pig cerebral cortex at 10 uM Cavia porcellus 18.5 %
Apparent IC50 value by [3H]batrachotoxinin-A-20-alpha-benzoate-binding test performed in rat brain synaptosomes Rattus norvegicus 860.0 nM
Inhibition of human Nav1.2 channel expressed in HEK cells at 10 uM by patch-clamp electrophysiology method Homo sapiens 10.6 %
Inhibition of human Nav1.2 channel expressed in HEK cells at 100 uM by patch-clamp electrophysiology method Homo sapiens 21.2 %
Neurotoxicity in mouse assessed as decrease in locomotor activity at 30 mg/kg, ip after 1 hr relative to control Mus musculus 64.0 %
Sedative-hypnotic effect in mouse assessed as inhibition of locomotor activity at 25 mg/kg, po by actophotometer Mus musculus 70.0 %
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy Homo sapiens -2.0 %
Inhibition of human aquaporin 4 M23 isoform expressed in Xenopus laevis oocytes at 20 uM Homo sapiens 58.0 %
Behavioral activity in albino mouse assessed as decrease in locomotor activity at 100 mg/kg, ip by actophotometer Mus musculus 69.0 %
Inhibition of human FAAH at 1 uM Homo sapiens 10.78 %
Inhibition of human NaV1.2 expressed in HEK cells at 10 uM at -60 mV holding potential by patch clamp recording technique Homo sapiens 10.6 %
Inhibition of human voltage-gated sodium channel 1.2 expressed in human HEK293 cells at 10 uM by two-microelectrode voltage-clamp electrophysiology Homo sapiens 10.0 %
Inhibition of human voltage-gated sodium channel 1.2 expressed in HEK293 cells at 1 uM by two-microelectrode voltage-clamp electrophysiology Homo sapiens 10.0 %
Displacement of [35S]MK-0499 from human ERG at 0.3 uM after >90 mins by scintillation counting Homo sapiens 9.0 %
Displacement of [35S]MK-0499 from human ERG at 1 uM after >90 mins by scintillation counting Homo sapiens 20.0 %
Displacement of [35S]MK-0499 from human ERG at 3 uM after >90 mins by scintillation counting Homo sapiens 28.0 %
Displacement of [35S]MK-0499 from human ERG at 10 uM after >90 mins by scintillation counting Homo sapiens 17.0 %
Displacement of [35S]MK-0499 from human ERG at 30 uM after >90 mins by scintillation counting Homo sapiens 40.0 %
Displacement of [3H]BTX-B from VGSC site 2 in rat forebrain membranes at 40 uM incubated at 37 degC for 60 mins Rattus norvegicus 28.0 %
Inhibition of human NaV1.2 expressed in HEK293 cells at 10 uM using sodium currents elicited through depolarizing step from holding potential of -100 mV to +10 mV for 25 ms at 15 s intervals by whole cell patch clamp method Homo sapiens 11.0 %
Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting Homo sapiens 25.4 %
Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 20.2 %
Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 11.1 %
Sedative-hypnotic activity in Mus musculus (mouse) assessed as inhibition of locomotory activity at 100 mg/kg, ip measured after 1 hr by actophotometer test Mus musculus 70.0 %
Behavioral activity in Mus musculus albino (mouse) assessed as inhibition of locomotion at 25 mg/kg, ip after 1 hr by actophotometric analysis relative to control Mus musculus 70.0 %
Displacement of [3H]BTX-B from neurotoxin site 2 of voltage-gated sodium channel in rat cerebral cortex synaptoneurosomes at 100 uM by scintillation counting analysis Rattus norvegicus 49.61 %
Time dependent inhibition of CYP1A2 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2B6 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2C9 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2C19 in human liver microsomes at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2D6 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP3A4 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2C8 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Displacement of [3H]BTX from voltage-sensitive Na+ channel site 2 in rat cerebral cortex synaptoneurosomes at 100 uM after 60 mins by liquid scintillation spectroscopic analysis Rattus norvegicus 53.9 %
Displacement of [3H]nitrendipine from voltage-sensitive L-type calcium channel in Sprague-Dawley rat cerebral cortex synaptoneurosomes at 100 uM Rattus norvegicus 57.8 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 13.07 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.0 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.0 %

Related Entries

Environmental Exposure

Environmental Exposure Map
Countries
USA

Cross References

Resources Reference
ChEBI 8107
ChEMBL CHEMBL16
DrugBank DB00252
DrugCentral 2152
FDA SRS 6158TKW0C5
Human Metabolome Database HMDB0014397
Guide to Pharmacology 2624
KEGG C07443
PharmGKB PA450947
PubChem 1775
SureChEMBL SCHEMBL3440
ZINC ZINC000002510358
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