General
Preferred name
PHENYTOIN
Synonyms
PHENYTOIN SODIUM ()
5,5-Diphenylhydantoin ()
Diphenylhydantoin ()
5,5-Diphenylhydantoin sodium salt ()
Diphenylhydantoin Sodium ()
Dilantin sodium ()
Diphantoine ()
Phenytoin (Lepitoin) ()
Phenytoin sodium (Dilantin) ()
5,5-Diphenylhydantoin (sodium salt) ()
Phenytoin (sodium) ()
Aleviatin, Diphenylhydantoin sodium, Eptoin, Phenytoin soluble, Prompt,Phenytek,Dilantin sodium, Diphantoine ()
Di-Hydan, Dihycon, Dilabid, Diphedan, Diphenat, Diphenylan, Diphenylhydantoin, Hydantol, Lehydan, NSC 8722 ()
Phenytoin-d10 ()
Extended Phenytoin Sodium ()
Prompt Phenytoin Sodium ()
Dilantin ()
Phenytoin sodium for injection ()
Diphenylan Sodium ()
Pentran ()
NSC-757274 ()
Phenytoinum natricum ()
Phenytex ()
Antisacer ()
Phenytoin sodium, prompt ()
Phenytoin sodium salt ()
Phenytoin sodium,prompt ()
Phenytoin sodium extended ()
Phenytoin sodium, extended ()
Tacosal ()
Phenytek ()
Phenytoin sodium,extended ()
SM-88 COMPONENT PHENYTOIN ()
Dilabid ()
Epamin ()
NSC-8722 ()
Dilantin-30 ()
Dilantin-125 ()
Phenytoinum ()
Lepitoin ()
Hydantol ()
Phentytoin ()
Zentropil ()
P&D ID
PD002756
CAS
630-93-3
57-41-0
1421-15-4
125-59-7
65854-97-9
Tags
natural product
drug
available
Approved by
FDA
First approval
1956
1953
Drug indication
Epilepsy
Anticonvulsant
Drug Status
vet_approved
approved
Max Phase
4.0
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
PHARMACODYNAMICS Phenytoin is an antiepileptic drug used in the treatment of epilepsy. The primary site of action appears to be the motor cortex where spread of seizure activity is inhibited. Phenytoin exerts an inhibitory action on the by reducing the electrical activity of brain stem centers that induce tonic phase of tonic-clonic (grand mal) seizures. Phenytoin acts to dampen the unwanted, runaway brain activity seen in seizure by reducing electrical conductance among brain cells. It lacks the sedation effects associated with phenobarbital. There are some indications that phenytoin has other effects, including anxiety control and mood stabilization, although it has never been approved for those purposes by the FDA. Phenytoin is primarily metabolized by CYP2C9.
MOA Phenytoin causes a voltage-dependent block of voltage gated sodium channels on the neuronal cell membrane, limiting the spread of seizure activity and reducing seizure propagation. It promotes the efflux of sodium ions from neurons. In doing so, it stabilizes the threshold against hyperexcitability caused by excessive stimulation of environmental changes capable of reducing the membrane sodium gradient. Phenytoin reduces the post-tetanic potentiation at synapses, leading to prevention of cortical seizure foci from detonating adjacent cortical areas.
DESCRIPTION Phenytoin is an anti-seizure drug. (GtoPdb)
DESCRIPTION Anticonvulsant; anti-epileptic (LOPAC library)
DESCRIPTION Phenytoin Sodium is a potent multi-channel blocker, which blocks Na+, K+ and Ca 2+ channels and selectively blocks persistent INaP over shorter INaP actions. (BOC Sciences Bioactive Compounds)
DESCRIPTION Anticonvulsant; appears to stabilize excitable membranes perhaps through effects on Na+, K+, and Ca2+ channels (LOPAC library)
DESCRIPTION Phenytoin is believed to protect against seizures by causing voltage-dependent block of voltage gated sodium channels. (BOC Sciences Bioactive Compounds)
Cell lines
1
Organisms
1
Compound Sets
27
AdooQ Bioactive Compound Library
A10722
A10721
BOC Sciences Bioactive Compounds
phenytoin-sodium-cas-630-93-3-item-84-180245
phenytoin-cas-57-41-0-item-84-71990
Cayman Chemical Bioactives
24037
33245
ChEMBL Approved Drugs
CHEMBL1611
CHEMBL16
ChEMBL Drugs
CHEMBL1611
CHEMBL16
Drug Repurposing Hub
DrugBank
DB00252
DrugBank Approved Drugs
DB00252
DrugCentral
2152
DrugCentral Approved Drugs
2152
DrugMAP
DMNOKBV
DrugMAP Approved Drugs
DMNOKBV
DrugMatrix
Enamine BioReference Compounds
EU-OPENSCREEN Bioactive Compound Library
EOS100899
Guide to Pharmacology
2624
LOPAC library
MedChem Express Bioactive Compound Library
HY-B0448A
HY-B0448
NCATS Inxight Approved Drugs
6158TKW0C5
NIH Clinical Collections (NCC)
NPC Screening Collection
NURSA ligand set
nursa/index.jsf?doi=10.1621%2F9U7S3DDJ7T
ReFrame library
Selleckchem Bioactive Compound Library
Phenytoin-sodium-Dilantin
Phenytoin-Lepitoin
TargetMol Bioactive Compound Library
T0008
T0939
The Spectrum Collection
VGSC-DB
NA0001
NA0002
NA0003
NA0004
NA0005
NA0006
External IDs
91
Properties
(calculated by RDKit )
Molecular Weight
252.09
Hydrogen Bond Acceptors
2
Hydrogen Bond Donors
2
Rotatable Bonds
2
Ring Count
3
Aromatic Ring Count
2
cLogP
1.77
TPSA
58.2
Fraction CSP3
0.07
Chiral centers
0.0
Largest ring
6.0
QED
0.8
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Pathway
Membrane Transporter/Ion Channel
Anti-infection
Target
Sodium Channel
SCN10A, SCN11A, SCN1A, SCN2A, SCN3A, SCN4A, SCN5A, SCN7A, SCN8A, SCN9A
Virus Protease
MOA
Sodium Channel inhibitor
hydantoin antiepileptic
Indication
seizures
Therapeutic Class
Anticonvulsants
VGSC Target
Nav1.2
Nav1.5
Nav1.7
Source data