ContaminantDB: Phenytoin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (10)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:26:24 UTC

Update Date

2026-03-31 18:53:50 UTC

Accession Number

CHEM002154

Identification

Common Name

Phenytoin

Class

Small Molecule

Description

An anticonvulsant that is used in a wide variety of seizures. It is also an anti-arrhythmic and a muscle relaxant. The mechanism of therapeutic action is not clear, although several cellular actions have been described including effects on ion channels, active transport, and general membrane stabilization. The mechanism of its muscle relaxant effect appears to involve a reduction in the sensitivity of muscle spindles to stretch. Phenytoin has been proposed for several other therapeutic uses, but its use has been limited by its many adverse effects and interactions with other drugs.

Contaminant Sources

Clean Air Act Chemicals
HMDB Contaminants - Urine
HPV EPA Chemicals
IARC Carcinogens Group 2B
STOFF IDENT Compounds
Suspected Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Amine
Anticonvulsant
Drug
Metabolite
Organic Compound
Synthetic Compound
Voltage-Gated Sodium Channel Blocker

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5,5-Diphenyl-imidazolidine-2,4-dione	ChEBI
5,5-Diphenylimidazolidine-2,4-dione	ChEBI
5,5-Diphenyltetrahydro-1H-2,4-imidazoledione	ChEBI
DILANTIN	ChEBI
Fenitoina	ChEBI
PHENTYTOIN	ChEBI
Phenytoine	ChEBI
Phenytoinum	ChEBI
5,5-Diphenylhydantoin	HMDB
5,5-Dwufenylohydantoina	HMDB
Dihydantoin	HMDB
Diphenylan sodium	HMDB
Diphenylhydantoin	HMDB
Diphenylhydatanoin	HMDB
Phenytoin sodium	HMDB
Difenin	HMDB
Diphenylhydantoinate, sodium	HMDB
Park davis brand OF phenytoin	HMDB
Pfizer brand OF phenytoin	HMDB
Sodium diphenylhydantoinate	HMDB
Dihydan	HMDB
Epamin	HMDB
Phenytoin pfizer brand	HMDB
Antisacer	HMDB
Epanutin	HMDB
Hydantol	HMDB
Phenytoin phizer brand	HMDB
Fenitoin	HMDB
Phizer brand OF phenytoin	HMDB

Chemical Formula

C₁₅H₁₂N₂O₂

Average Molecular Mass

252.268 g/mol

Monoisotopic Mass

252.090 g/mol

CAS Registry Number

57-41-0

IUPAC Name

5,5-diphenylimidazolidine-2,4-dione

Traditional Name

silantin

SMILES

O=C1NC(=O)C(N1)(C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

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)

InChI Key

CXOFVDLJLONNDW-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenylhydantoins. These are heterocyclic aromatic compounds containing an imiazolidinedione moiety substituted by a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azolidines

Sub Class

Imidazolidines

Direct Parent

Phenylhydantoins

Alternative Parents

Substituents

Diphenylmethane
5-phenylhydantoin
Phenylimidazolidine
Alpha-amino acid or derivatives
5-monosubstituted hydantoin
N-acyl urea
Ureide
Monocyclic benzene moiety
Benzenoid
Dicarboximide
Urea
Carbonic acid derivative
Carboxylic acid derivative
Azacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

imidazolidine-2,4-dione (CHEBI:8107 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

anticonvulsant

Biological Roles

teratogenic agent

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	286°C
Boiling Point	Not Available
Solubility	32 mg/L (at 22°C)

Predicted Properties

Property	Value	Source
Water Solubility	0.071 g/L	ALOGPS
logP	2.26	ALOGPS
logP	2.15	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	8.49	ChemAxon
pKa (Strongest Basic)	-9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.2 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	70.18 m³·mol⁻¹	ChemAxon
Polarizability	25.48 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-003r-7930000000-447969b9c242748dd943	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0udi-0090000000-4176043a7a73caee2667	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0zgi-5960000000-e1dcb47a1c082f04f456	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0udi-1390000000-22c71a7e4dbf9c7acab5	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0udi-2190000000-50174e33af92b04d1a6e	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-003r-7930000000-447969b9c242748dd943	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0udi-0090000000-4176043a7a73caee2667	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0zgi-5960000000-e1dcb47a1c082f04f456	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0udi-1390000000-22c71a7e4dbf9c7acab5	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0udi-2190000000-50174e33af92b04d1a6e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00lr-0920000000-edf72a4c297e405a2600	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-001i-0950000000-a80521d4dc3976a29b2c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0ue9-2900000000-a58471ae75fa7319c03d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0udi-0090000000-aaae845342f345f89695	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0udi-0390000000-f8da1896c569c120faa2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0udi-0920000000-07c872b05aade63c402b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0udi-0900000000-be6790637be99260525e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0udi-0900000000-9a17fa0b243c8282f3ba	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0udi-0900000000-69302626996b2b24c153	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0fai-0690000000-f9eeceb82d117127f6ea	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-001i-0910000000-9edcfc62014a6aa7778f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-001i-0900000000-d4dde5db680fb7722a49	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0ue9-0900000000-482874b33812389ae726	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0udi-0900000000-44f07dc29daf8cdf80c2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0udi-1900000000-1241292d531ed37544c7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-001i-0950000000-a80521d4dc3976a29b2c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0ue9-2900000000-a58471ae75fa7319c03d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-0udi-0920000000-97a0af331da9afcf54b8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-0udi-0900000000-9918b159c9e50b11016f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-0udi-0900000000-c2ba734800c5db1b68cf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0290000000-168825c4263cc790be0b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f89-0950000000-27e345a92f7734114654	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uyi-1900000000-5828317e8dac2d03e548	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-e1551530faa59a549515	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-1190000000-354c210fa308dab349f3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9700000000-d5833bfc084997249fe4	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0f89-4940000000-2a0dda513d9f63dc6610	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Intravenous, Oral, Intramuscular. Bioavailability 70-100% oral, 24.4% for rectal and intravenous administration. Rapid rate of absorption with peak blood concentration expected in 1½ to 3 hours.

Mechanism of Toxicity

Phenytoin acts on sodium channels on the neuronal cell membrane, limiting the spread of seizure activity and reducing seizure propagation. By promoting sodium efflux from neurons, phenytoin tends to stabilize the threshold against hyperexcitability caused by excessive stimulation or environmental changes capable of reducing membrane sodium gradient. This includes the reduction of post-tetanic potentiation at synapses. Loss of post-tetanic potentiation prevents cortical seizure foci from detonating adjacent cortical areas.

Metabolism

Primarily hepatic. The majority of the dose (up to 90%) is metabolized to 5-(4'-hydroxyphenyl)-5-phenylhydantoin (p-HPPH). This metabolite undergoes further glucuronidation and is excreted into the urine. CYP2C19 and CYP2C9 catalyze the aforementioned reaction. Route of Elimination: Most of the drug is excreted in the bile as inactive metabolites which are then reabsorbed from the intestinal tract and excreted in the urine. Urinary excretion of phenytoin and its metabolites occurs partly with glomerular filtration but, more importantly, by tubular secretion. Half Life: 22 hours (range of 7 to 42 hours)

Toxicity Values

Oral, mouse: LD₅₀ = 150 mg/kg; Oral, rat: LD₅₀ = 1635 mg/kg.

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2B, possibly carcinogenic to humans. (1)

Uses/Sources

For the control of generalized tonic-clonic (grand mal) and complex partial (psychomotor, temporal lobe) seizures and prevention and treatment of seizures occurring during or following neurosurgery.

Minimum Risk Level

Not Available

Health Effects

May cause a potentially dangerous rash that may develop into Stevens Johnson syndrome, an extremely rare but potentially fatal skin disease.

Symptoms

Symptoms of overdose include coma, difficulty in pronouncing words correctly, involuntary eye movement, lack of muscle coordination, low blood pressure, nausea, sluggishness, slurred speech, tremors, and vomiting.

Treatment

Treatment is nonspecific since there is no known antidote. The adequacy of the respiratory and circulatory systems should be carefully observed and appropriate supportive measures employed. Hemodialysis can be considered since phenytoin is not completely bound to plasma proteins. Total exchange transfusion has been used in the treatment of severe intoxication in pediatric patients. (3)

Concentrations

Not Available

External Links

DrugBank ID

DB00252

HMDB ID

HMDB0014397

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID