PHENYTOIN

Search structure
Trade Names:
Synonyms:
Status: Approved (1953)
Entry Type: Small molecule
Molecule Category: Parent
ATC: N03AB02
UNII: 6158TKW0C5

Structure
InChI Key CXOFVDLJLONNDW-UHFFFAOYSA-N
Smile O=C1N=C(O)NC1(c1ccccc1)c1ccccc1
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

Pharmacology

Action Mechanism of Action Reference
BLOCKER Sodium channel alpha subunit blocker PubMed PubMed FDA
Primary Target
Nav1.2
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
- - - -

Metabolites

visNetwork

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Depressive Disorder 3 D003866 ClinicalTrials
Schizophrenia 3 D012559 ClinicalTrials
Anxiety 3 D001007 ClinicalTrials
Dementia 3 D003704 ClinicalTrials
Anemia, Sickle Cell 2 D000755 ClinicalTrials
Thalassemia 2 D013789 ClinicalTrials
Optic Neuritis 2 D009902 ClinicalTrials
Pancreatic Neoplasms 2 D010190 ClinicalTrials
Polyneuropathies 2 D011115 ClinicalTrials
Wounds and Injuries 2 D014947 ClinicalTrials
Cocaine-Related Disorders 1 D019970 ClinicalTrials
Leukemia 1 D007938 ClinicalTrials
Lymphoma 1 D008223 ClinicalTrials
Neuroblastoma 1 D009447 ClinicalTrials
Anemia 1 D000740 ClinicalTrials

Related Entries

Salt

Side Effects from Label

Side effects Relative Frequency (%) Labels
Eye disorders Nystagmus 59.1
Skin and subcutaneous tissue disorders Pruritus 48.9
Eye disorders Nystagmus 44.4
Cardiac disorders Dizziness 31.1
Cardiac disorders Dizziness 27.3
Nervous system disorders Somnolence 27.3
Nervous system disorders Somnolence 20.0
Nervous system disorders Ataxia 18.2
Eye disorders Nystagmus 15.1
Gastrointestinal disorders Nausea 13.6
Nervous system disorders Tremor 13.1
Nervous system disorders Ataxia 11.1
Nervous system disorders Somnolence 9.8
Nervous system disorders Tremor 9.5
Eye disorders Amblyopia 9.1
Nervous system disorders Hypoaesthesia 9.1
Vascular disorders Hypotension 9.1
Ear and labyrinth disorders Tinnitus 9.1
Nervous system disorders Tremor 9.1
Gastrointestinal disorders Vomiting 9.1
Nervous system disorders Headache 8.9
Gastrointestinal disorders Nausea 8.9
Ear and labyrinth disorders Tinnitus 8.9
Nervous system disorders Ataxia 8.4
Nervous system disorders Ataxia 8.2
Eye disorders Nystagmus 8.2
Nervous system disorders Coordination abnormal 7.8
Nervous system disorders Depressed level of consciousness 7.7
Vascular disorders Hypotension 7.7
Nervous system disorders Stupor 7.7
Blood and lymphatic system disorders Ecchymosis 7.3
Nervous system disorders Somnolence 6.7
Injury, poisoning and procedural complications Injury 6.6
Cardiac disorders Dizziness 5.0
Nervous system disorders Coordination abnormal 4.9
Blood and lymphatic system disorders Ecchymosis 4.9
Nervous system disorders Headache 4.9
Nervous system disorders Hyporeflexia 4.9
Injury, poisoning and procedural complications Brain oedema 4.5
Nervous system disorders Coordination abnormal 4.5
Nervous system disorders Depressed level of consciousness 4.5
Gastrointestinal disorders Dry mouth 4.5
Nervous system disorders Headache 4.5
Gastrointestinal disorders Nausea 4.5
Skin and subcutaneous tissue disorders Pruritus 4.5
Nervous system disorders Stupor 4.5
Nervous system disorders Coordination abnormal 4.4
Gastrointestinal disorders Dry mouth 4.4
Nervous system disorders Extrapyramidal disorder 4.4
Nervous system disorders Paraesthesia 4.4
Gastrointestinal disorders Pelvic pain 4.4
Gastrointestinal disorders Tongue disorder 4.4
General disorders and administration site conditions Asthenia 3.9
Nervous system disorders Paraesthesia 3.9
Injury, poisoning and procedural complications Injury 3.4
Nervous system disorders Agitation 3.3
General disorders and administration site conditions Asthenia 3.3
Eye disorders Diplopia 3.3
Cardiac disorders Dizziness 3.3
Gastrointestinal disorders Dysgeusia 3.3
Nervous system disorders Paraesthesia 3.3
Nervous system disorders Tremor 3.3
Nervous system disorders Hyporeflexia 2.8
Skin and subcutaneous tissue disorders Pruritus 2.8
Gastrointestinal disorders Vomiting 2.8
Eye disorders Amblyopia 2.2
General disorders and administration site conditions Asthenia 2.2
Musculoskeletal and connective tissue disorders Back pain 2.2
Injury, poisoning and procedural complications Brain oedema 2.2
Ear and labyrinth disorders Deafness 2.2
Nervous system disorders Dysarthria 2.2
Nervous system disorders Headache 2.2
Nervous system disorders Hypoaesthesia 2.2
Musculoskeletal and connective tissue disorders Osteoarthritis 2.2
Cardiac disorders Tachycardia 2.2
Ear and labyrinth disorders Vertigo 2.2
Gastrointestinal disorders Vomiting 2.2
Skin and subcutaneous tissue disorders Pruritus 0.5
Vascular disorders Hypotension 0.3
Cardiac disorders Bradycardia 0.2

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Nervous system disorders
22.53
General disorders and administration site conditions
12.04
Injury, poisoning and procedural complications
10.49
Psychiatric disorders
7.36
Investigations
6.32
Immune system disorders
6.07
Skin and subcutaneous tissue disorders
5.69
Musculoskeletal and connective tissue disorders
4.53
Gastrointestinal disorders
4.06
Vascular disorders
2.98
Infections and infestations
2.84
Cardiac disorders
2.48
Eye disorders
2.48
Respiratory, thoracic and mediastinal disorders
2.01

Cross References

Resources Reference
CAS NUMBER 57-41-0
ChEBI 8107
ChEMBL CHEMBL16
DrugBank DB00252
DrugCentral 2152
EPA CompTox DTXSID8020541
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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