PHENYTOIN SODIUM

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Trade Names
Synonyms
Status
Molecule Category Salt-form
UNII 4182431BJH
EPA CompTox DTXSID2023775
Parent Compound: PHENYTOIN

Structure

InChI Key FJPYVLNWWICYDW-UHFFFAOYSA-M
Smiles O=C1N=C([O-])NC1(c1ccccc1)c1ccccc1.[Na+]
InChI
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C15H11N2NaO2
Molecular Weight 274.25
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(%)
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 96
Assay Description Organism Bioactivity Reference
Anticonvulsant activity in mouse assessed as inhibition of maximal electroshock-induced seizures at 30 mg/kg, po Mus musculus 90.0 %
Anticonvulsant activity in mouse assessed as inhibition of maximal electroshock-induced seizures at 15 mg/kg, po Mus musculus 50.0 %
Anticonvulsant activity in mouse assessed as inhibition of maximal electroshock-induced seizures at 7.5 mg/kg, po Mus musculus 20.0 %
Anticonvulsant activity in Swiss albino mouse assessed as protection against maximal electroshock-induced seizures measuring inhibition of extension phase at 25 mg/kg, ip after 2 hrs Mus musculus 80.73 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 95.94 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 97.47 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus 10.31 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 2.45 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 7.94 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 8.36 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 25.4 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 2.49 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans 1.23 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens -2.56 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 26.48 %
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 0.33 % 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 0.33 %

Cross References

Resources Reference
ChEBI 8107
ChEMBL CHEMBL1611
FDA SRS 4182431BJH
Guide to Pharmacology 2624
KEGG C07443
PubChem 657302
SureChEMBL SCHEMBL3051683
ZINC ZINC02510358
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