Phenytoin

Highest phase reached

Approved

www.ebi.ac.uk

Drug type

Small molecule

www.ebi.ac.uk

First approval year

1953

www.ebi.ac.uk

First approval year: 1953
www.ebi.ac.uk

Listing at source: Listed

Highest phase reached: Approved
www.ebi.ac.uk

Drug type: Small molecule
www.ebi.ac.uk

Drug name: Phenytoin
www.ebi.ac.uk

Molecular weight: 252.27
www.ebi.ac.uk

Structure (SMILES): O=C1NC(=O)C(c2ccccc2)(c2ccccc2)N1
www.ebi.ac.uk

dilabid
Dilabid
dilantin
Dilantin
dilantin 125
dilantin 30
Dilantin-125
Dilantin-30
hydantol
Hydantol
phentytoin
Phentytoin
phenytoin
Phenytoin

diphenylhydantoin
Diphenylhydantoin
epamin
Epamin
fenitoina
Fenitoina
lepitoin
Lepitoin
nsc 8722
NSC-8722
phenytoin
Phenytoin
PHENYTOIN [EP MONOGRAPH]
PHENYTOIN [HSDB]
PHENYTOIN [IARC]
phenytoin [INN]
PHENYTOIN [JAN]
PHENYTOIN [MART.]
PHENYTOIN [MI]
PHENYTOIN [ORANGE BOOK]
PHENYTOIN [USAN]
PHENYTOIN [USP IMPURITY]
PHENYTOIN [USP MONOGRAPH]
PHENYTOIN [USP-RS]
PHENYTOIN [VANDF]

And 29 more, listed on the interactive page.

CAS registry numbers

57-41-0

ChEMBL ID: CHEMBL16
www.ebi.ac.uk

InChIKey: CXOFVDLJLONNDW-UHFFFAOYSA-N
www.ebi.ac.uk

RxNorm IDs (RxCUI)

8183

FDA ingredient codes (UNII)

6158TKW0C5

N03AB02
N03AB52

Sources for recorded values

www.ebi.ac.uk

1775
146015336

Applicant: VIATRIS
Approval date: 6 Jan 1953
Application number: NDA008762

Patents: 0
Designations: 1
First in class: No
Fast track: No
Breakthrough designation: No
Orphan designation: No
Priority review: No
Orphan exclusivity: No
Accelerated approval: No
Availability: Prescription only
Boxed warning: Yes

Pharmacology name: phenytoin
Type: Synthetic organic
Drug name stem: -toin
Approval recorded by Guide to Pharmacology: Yes

Administration routes

Oral
Parenteral

Mechanism
Sodium channel alpha subunit blocker
Action type
Blocker
Target
Sodium channel alpha subunit
Protein identifier
P35498
Mechanism
Sodium channel alpha subunit blocker
Action type
Blocker
Target
Sodium channel alpha subunit
Protein identifier
P35499
Mechanism
Sodium channel alpha subunit blocker
Action type
Blocker
Target
Sodium channel alpha subunit
Protein identifier
Q01118
Mechanism
Sodium channel alpha subunit blocker
Action type
Blocker
Target
Sodium channel alpha subunit
Protein identifier
Q14524
Mechanism
Sodium channel alpha subunit blocker
Action type
Blocker
Target
Sodium channel alpha subunit
Protein identifier
Q15858
Mechanism
Sodium channel alpha subunit blocker
Action type
Blocker
Target
Sodium channel alpha subunit
Protein identifier
Q99250
Mechanism
Sodium channel alpha subunit blocker
Action type
Blocker
Target
Sodium channel alpha subunit
Protein identifier
Q9NY46
Mechanism
Sodium channel alpha subunit blocker
Action type
Blocker
Target
Sodium channel alpha subunit
Protein identifier
Q9UI33
Mechanism
Sodium channel alpha subunit blocker
Action type
Blocker
Target
Sodium channel alpha subunit
Protein identifier
Q9UQD0
Mechanism
Sodium channel alpha subunit blocker
Action type
Blocker
Target
Sodium channel alpha subunit
Protein identifier
Q9Y5Y9
Action
Pore blocker
Action type
PORE_BLOCKER
Target
Nav1.2
Gene symbol
SCN2A
Protein identifier
Q99250
Median affinity
4.9
Affinity units
pIC50
Primary target
Yes

Open Targets mechanisms

Mechanism
Sodium channel alpha subunit blocker
Action type
Blocker
Target
Sodium channel alpha subunit

Action type
Blocker
Gene symbol
SCN1A
Protein identifier
P35498
Organism
Homo sapiens
Target development level
Clinical
Action type
Blocker
Gene symbol
SCN4A
Protein identifier
P35499
Organism
Homo sapiens
Target development level
Clinical
Action type
Blocker
Gene symbol
SCN5A
Protein identifier
Q14524
Organism
Homo sapiens
Target development level
Clinical
Action type
Blocker
Gene symbol
SCN9A
Protein identifier
Q15858
Organism
Homo sapiens
Target development level
Clinical
Action type
Blocker
Gene symbol
SCN2A
Protein identifier
Q99250
Organism
Homo sapiens
Target development level
Clinical
Action type
Blocker
Gene symbol
SCN3A
Protein identifier
Q9NY46
Organism
Homo sapiens
Target development level
Clinical
Action type
Blocker
Gene symbol
SCN8A
Protein identifier
Q9UQD0
Organism
Homo sapiens
Target development level
Clinical

Condition
Epilepsy
Highest recorded phase
4
Condition identifier
EFO:0000474
Subject identifier
D004827
Condition
Immune System Diseases
Highest recorded phase
1
Condition identifier
EFO:0000540
Subject identifier
D007154
Condition
Wounds and Injuries
Highest recorded phase
2
Condition identifier
EFO:0000546
Subject identifier
D014947
Condition
Leukemia
Highest recorded phase
1
Condition identifier
EFO:0000565
Subject identifier
D007938
Condition
Lymphoma
Highest recorded phase
1
Condition identifier
EFO:0000574
Subject identifier
D008223
Condition
Neuroblastoma
Highest recorded phase
1
Condition identifier
EFO:0000621
Subject identifier
D009447
Condition
Cocaine-Related Disorders
Highest recorded phase
1
Condition identifier
EFO:0002610
Subject identifier
D019970
Condition
Pancreatic Neoplasms
Highest recorded phase
2
Condition identifier
EFO:0002618
Subject identifier
D010190
Condition
Anemia
Highest recorded phase
1
Condition identifier
EFO:0004272
Subject identifier
D000740
Condition
Anxiety
Highest recorded phase
3
Condition identifier
EFO:0005230
Subject identifier
D001007
Condition
Optic Neuritis
Highest recorded phase
2
Condition identifier
EFO:0007405
Subject identifier
D009902
Condition
Polyneuropathies
Highest recorded phase
2
Condition identifier
EFO:0009562
Subject identifier
D011115
Condition
Thalassemia
Highest recorded phase
2
Condition identifier
EFO:1001996
Subject identifier
D013789
Condition
Dementia
Highest recorded phase
3
Condition identifier
HP:0000726
Subject identifier
D003704
Condition
Seizures
Highest recorded phase
4
Condition identifier
HP:0001250
Subject identifier
D012640
Condition
Depressive Disorder
Highest recorded phase
3
Condition identifier
MONDO:0002050
Subject identifier
D003866
Condition
Schizophrenia
Highest recorded phase
3
Condition identifier
MONDO:0005090
Subject identifier
D012559
Condition
Anemia, Sickle Cell
Highest recorded phase
2
Condition identifier
MONDO:0011382
Subject identifier
D000755

Condition identifier
EFO_0000474
Condition identifier
EFO_0000546
Highest recorded phase
2
Condition identifier
EFO_0001072
Highest recorded phase
3
Condition identifier
EFO_0002610
Highest recorded phase
1
Condition identifier
EFO_0005762
Highest recorded phase
2
Condition identifier
EFO_0007405
Highest recorded phase
2
Condition identifier
EFO_0008526
Condition identifier
EFO_0009562
Condition identifier
EFO_0010445
Highest recorded phase
1
Condition identifier
HP_0001250
Condition identifier
HP_0001250
Highest recorded phase
4
Condition identifier
HP_0010447
Condition identifier
HP_0012390
Highest recorded phase
1
Condition identifier
HP_0032660
Highest recorded phase
3
Condition identifier
MONDO_0001824
Highest recorded phase
2
Condition identifier
MONDO_0004953
Highest recorded phase
3
Condition identifier
MONDO_0005027
Highest recorded phase
4
Condition identifier
MONDO_0005089
Highest recorded phase
2
Condition identifier
MONDO_0005099
Condition identifier
MONDO_0005146
Condition identifier
MONDO_0005184
Highest recorded phase
2
Condition identifier
MONDO_0005192
Highest recorded phase
2
Condition identifier
MONDO_0005885
Highest recorded phase
2
Condition identifier
MONDO_0008315
Highest recorded phase
2
Condition identifier
MONDO_0009831
Highest recorded phase
3

And 2 more, listed on the interactive page.

Warning
Black Box Warning
Effect
cardiotoxicity
Country
United States
Warning
Black Box Warning
Effect
hematological toxicity
Country
United States
Warning
Black Box Warning
Effect
misuse
Country
United States
Warning
Black Box Warning
Effect
vascular toxicity
Country
United States

Event
anticonvulsant drug level abnormal
Reports
34
Reporting signal score
156.855
Event
anticonvulsant drug level below therapeutic
Reports
109
Reporting signal score
455.702
Event
anticonvulsant drug level decreased
Reports
175
Reporting signal score
720.134
Event
ataxia
Reports
316
Reporting signal score
771.49
Event
balance disorder
Reports
154
Reporting signal score
116.291
Event
blood albumin decreased
Reports
68
Reporting signal score
114.408
Event
cerebellar atrophy
Reports
105
Reporting signal score
435.628
Event
confusional state
Reports
279
Reporting signal score
147.653
Event
convulsion
Reports
1,004
Reporting signal score
2,255.23
Event
coordination abnormal
Reports
86
Reporting signal score
141.607
Event
drug hypersensitivity
Reports
765
Reporting signal score
676.575
Event
drug interaction
Reports
518
Reporting signal score
382.194
Event
drug level below therapeutic
Reports
79
Reporting signal score
163.328
Event
drug level changed
Reports
44
Reporting signal score
147.986
Event
drug level fluctuating
Reports
46
Reporting signal score
152.323
Event
drug rash with eosinophilia and systemic symptoms
Reports
106
Reporting signal score
251.246
Event
drug reaction with eosinophilia and systemic symptoms
Reports
347
Reporting signal score
648.694
Event
drug resistance
Reports
161
Reporting signal score
214.137
Event
drug toxicity
Reports
182
Reporting signal score
405.655
Event
dysarthria
Reports
164
Reporting signal score
171.946
Event
epilepsy
Reports
164
Reporting signal score
201.976
Event
generalised tonic-clonic seizure
Reports
92
Reporting signal score
115.534
Event
gingival hypertrophy
Reports
50
Reporting signal score
140.553
Event
grand mal convulsion
Reports
151
Reporting signal score
296.471
Event
lethargy
Reports
157
Reporting signal score
114.737

And 14 more, listed on the interactive page.

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NCT03512756
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NCT04647877
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Dose: 2x 50mg tablets
Route: Oral
How often: Three times daily

Hydrogen bond acceptors: 2
Hydrogen bond donors: 2
Polar surface area: 58.2
Calculated partition coefficient (ALogP): 1.77
Calculated partition coefficient (XLogP): 2.5
Prodrug: No
Chirality: Achiral
Inorganic: No
Rule-of-five violations: 0
Rotatable bonds: 2
Heavy atoms: 19
Molecular formula: C15H12N2O2
Monoisotopic mass: 252.089877630
Natural product: Yes

0071-0007
0121-0892
0615-8424
0615-8623
0904-7199
58151-115
60687-156
60687-275
64980-573
66993-372
17856-4070
51672-4069
51672-4146
59762-0531
70518-0841

Recorded assays: 7,041
Active assays: 54

Confirmatory
Other
Screening
Summary

Anticonvulsants
id.nlm.nih.gov
Voltage-Gated Sodium Channel Blockers
id.nlm.nih.gov
Cytochrome P-450 CYP1A2 Inducers
id.nlm.nih.gov

These details could not be displayed.

Related records

Trials (68)

A Clinical Study of Belzutifan (MK-6482) Alone or With Phenytoin in Healthy Participants (CA46602/MK-6482-035)
A Comparison of the Effectiveness and Safety of Topiramate and Phenytoin in Patients With New Onset Epilepsy Requiring Rapid Initiation of Antiepileptic Drug Treatment
A Drug-drug Interaction Study to Assess the Effect of Phenytoin and Itraconazole on the Pharmacokinetics of Pelabresib in Healthy Participants
A Randomized Phase 2/3 Multi-Center Study of SM-88 in Participants With Metastatic Pancreatic Cancer
A Study of the Effect of Itraconazole and Phenytoin on Calderasib (MK-1084) in Healthy Adults (MK-1084-008)
A Study of the Interaction of TAK-279 With Substances That Have an Impact on Metabolism in Healthy Adults
A Study to Assess if Epanutin Infatabs 50 mg From Germany Are Similar to Dilantin Infatabs 50 mg From Australia
A Study to Assess the Effect of Phenytoin on the Drug Levels of Afimetoran and the Effect of Afimetoran on the Drug Levels of Midazolam
A Study to Evaluate the Effect of Multiple Doses of Itraconazole, Phenytoin, and Paroxetine on the Single-Dose Pharmacokinetics of Poziotinib in Healthy Adult Participants
A Study to Evaluate the Effects of Phenytoin and Itraconazole on Sonrotoclax (BGB-11417) in Healthy Volunteers
A Study to Evaluate VH4524184 Tablet Absorption, Effects of Food, and Interactions With Other Drugs in Healthy Adults
A Study to Investigate the Effect of the CYP3A Inducer Phenytoin and the CYP3A Inhibitor Itraconazole on the Pharmacokinetics of BGB-58067 in Healthy Participants
A Study to Investigate the Potential Pharmacokinetic Interactions Between Phenytoin or Carbamazepine and Telaprevir
A Study to Learn How Different Forms of The Study Medicine Called Phenytoin Are Taken up Into the Blood in Healthy Adults
AED/Statin Interaction Study
Antiepileptic Drugs and Vascular Risk Markers
Assess Safety and Efficacy of Levetiracetam(LEV;Keppra)for Seizure Prevention
Bioequivalence Study Of PHENYTOIN Suspension Made By Pfizer, Versus EPAMIN® Made By McNeil LA LLC In Healthy Volunteers Under Fasting Conditions
Bioequivalence Study Of Phenytoin Suspension Versus Epamin® In 34 Healthy Volunteers.
Bone Marrow Transplant From Related Donor for Patients With High Risk Hemoglobinopathies

Approved for (2)

Epilepsy
Visual epilepsy

In development for (16)

Anemia Phase 1
Anxiety Phase 3
Cocaine dependence Phase 1
Dementia Phase 3
Depressive disorder Phase 3
Exocrine pancreatic carcinoma Phase 2
Immune system disorder Phase 1
Injury Phase 2
Leukemia Phase 1
Lymphoma Phase 1
Neuroblastoma Phase 1
Optic neuritis Phase 2
Polyneuropathy Phase 2
Schizophrenia Phase 3
Sickle cell disease Phase 2
Thalassemia Phase 2

Targets (10)

SCN10A Sodium channel alpha subunit blocker
SCN11A Sodium channel alpha subunit blocker
SCN1A Sodium channel alpha subunit blocker
SCN2A Sodium channel alpha subunit blocker
SCN3A Sodium channel alpha subunit blocker
SCN4A Sodium channel alpha subunit blocker
SCN5A Sodium channel alpha subunit blocker
SCN7A Sodium channel alpha subunit blocker
SCN8A Sodium channel alpha subunit blocker
SCN9A Sodium channel alpha subunit blocker

Phenytoin

Development status

Names and chemistry

Brand names (14)

Other names (54)

Identifiers

ATC classification codes (2)

PubChem compound IDs (2)

Regulatory information

United States

Other regulatory facts

Pharmacology

Drug classification

Administration routes

Mechanisms of action (11)

Open Targets mechanisms

DrugCentral mechanisms (7)

Investigated indications (18)

Open Targets indications (27)

Open Targets warnings (4)

Reported adverse events (39)

Trial references (22)

Dosing

Chemical properties

National Drug Codes

Evidence counts

Active assay types (4)

Pharmacologic actions

Biological measurements

Related records

Trials (68)

Approved for (2)

In development for (16)

Other linked conditions (1)

Targets (10)