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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL16
CHEMBL16
Compound Name PHENYTOIN
ChEMBL Synonyms DILANTIN-125 | PHENYTEK | Phenytek | PROMPT PHENYTOIN SODIUM | Phenytex | PHENYTOIN | Hydantol | PENTRAN | DILANTIN-30 | DIPHENYLHYDANTOIN SODIUM | DIPHENYLAN SODIUM | Phentytoin | DILANTIN | PHENYTOIN SODIUM | EXTENDED PHENYTOIN SODIUM | Dilabid | DIPHENYLHYDANTOIN | PHENYTEX
Max Phase 4 (Approved)
Trade Names DILANTIN-125 | PHENYTEX | Dilabid | EXTENDED PHENYTOIN SODIUM | PHENYTOIN SODIUM | DILANTIN | Phentytoin | DIPHENYLAN SODIUM | DILANTIN-30 | PENTRAN | Hydantol | PHENYTOIN | PROMPT PHENYTOIN SODIUM | PHENYTEK | Diphenylhydantoin
Molecular Formula C15H12N2O2

Additional synonyms for CHEMBL16 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES OC1=NC(=O)C(N1)(c2ccccc2)c3ccccc3
Standard InChI InChI=1S/C15H12N2O2/c18-13-15(17-14(19)16-13,11-7-3-1-4-8-11 ...
Download InChI
Standard InChI Key CXOFVDLJLONNDW-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • Curated Drug Metabolism Pathways
  • DrugMatrix
  • HeCaToS Compounds
  • Open TG-GATEs
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL16

Molecule Features

CHEMBL16 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:Y Parenteral:Y Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Sodium channel alpha subunit blocker Sodium channel alpha subunit FDA PubMed PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
EpilepsyD004827EFO:0000474epilepsy4ATC
ATC
ClinicalTrials
Cocaine-Related DisordersD019970EFO:0002610cocaine dependence1ClinicalTrials
Anemia, Sickle CellD000755Orphanet:232Sickle cell anemia2ClinicalTrials
Depressive DisorderD003866EFO:0003761unipolar depression3ClinicalTrials
ThalassemiaD013789EFO:1001996Thalassemia2ClinicalTrials
Wounds and InjuriesD014947EFO:0000546injury2ClinicalTrials
AnxietyD001007EFO:0005230anxiety3ClinicalTrials
SchizophreniaD012559EFO:0000692schizophrenia3ClinicalTrials
SeizuresD012640HP:0001250Seizures2ClinicalTrials
Cognitive DysfunctionD060825HP:0100543cognitive impairment0ClinicalTrials
DementiaD003704HP:0000726dementia3ClinicalTrials
Optic NeuritisD009902EFO:0007405optic neuritis2ClinicalTrials

Clinical Data

ClinicalTrials.gov PHENYTOIN
The Cochrane Collaboration PHENYTOIN

Metabolites for CHEMBL16

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Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL16. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL4414 Plasmepsin 2 Plasmodium falciparum 0.995
CHEMBL4235 11-beta-hydroxysteroid dehydrogenase 1 Homo sapiens 0.203

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL4414 Plasmepsin 2 Plasmodium falciparum 0.965
CHEMBL4822 Beta-secretase 1 Homo sapiens 0.754
CHEMBL4235 11-beta-hydroxysteroid dehydrogenase 1 Homo sapiens 0.274

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
252.3 252.0899 1.97 2 61.69 ZWITTERION


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
2 2 0 4 2 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
1.84 10.79 1.74 -.71 2 19 0.86

Structural Alerts

There are 1 structural alerts for CHEMBL16. To view alerts please click here.

Compound Cross References

ATC N - NERVOUS SYSTEM
N03 - ANTIEPILEPTICS
N03A - ANTIEPILEPTICS
N03AB - Hydantoin derivatives
N03AB52 - phenytoin, combinations

N - NERVOUS SYSTEM
N03 - ANTIEPILEPTICS
N03A - ANTIEPILEPTICS
N03AB - Hydantoin derivatives
N03AB02 - phenytoin

ChemSpider ChemSpider:CXOFVDLJLONNDW-UHFFFAOYSA-N
DailyMed phenytoin phenytoin sodium
PubChem SID: 11111069 SID: 11532994 SID: 124879886 SID: 124886706 SID: 144204412 SID: 144209497 SID: 144210601 SID: 170464785 SID: 17389903 SID: 26753026 SID: 26753027 SID: 26753028 SID: 50106148 SID: 56423134 SID: 85230999 SID: 90340679 SID: 90341165
Wikipedia Phenytoin

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL16



ACToR 125-59-7 57-41-0
Atlas phenytoin
BindingDB 50003655 50101816
Brenda 103877 108876 10642 43502 49993
ChEBI 8107
DrugBank DB00252
DrugCentral 2152
eMolecules 5420227 13434342 507449
EPA CompTox Dashboard DTXSID8020541
FDA SRS 6158TKW0C5
Guide to Pharmacology 2624
Human Metabolome Database HMDB0014397
IBM Patent System C4D88CC562A319DBC05B249EF748CF43
KEGG Ligand C07443
LINCS LSM-5663
Mcule MCULE-2376673346
MolPort MolPort-002-365-712 MolPort-023-220-142 MolPort-001-785-683
Nikkaji J2.325F
NMRShiftDB 10021980
PharmGKB PA450947
PubChem 1775
PubChem: Thomson Pharma 14847761
Selleck Phenytoin-Lepitoin
SureChEMBL SCHEMBL3440
ZINC ZINC000002510358

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/CXOFVDLJLONNDW-UHFFFAOYSA-N spacer
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