Identification
- Summary
Ethotoin is a hydantoin antiepileptic used to control tonic-clonic and complex partial seizures.
- Brand Names
- Peganone
- Generic Name
- Ethotoin
- DrugBank Accession Number
- DB00754
- Background
Ethotoin is a hydantoin derivative and anticonvulsant. Ethotoin exerts an antiepileptic effect without causing general central nervous system depression. The mechanism of action is probably very similar to that of phenytoin. The latter drug appears to stabilize rather than to raise the normal seizure threshold, and to prevent the spread of seizure activity rather than to abolish the primary focus of seizure discharges. Ethotoin is no longer commonly used.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Ethotoin (DB00754)
- Weight
- Average: 204.2252
Monoisotopic: 204.089877638 - Chemical Formula
- C11H12N2O2
- Synonyms
- (±)-3-ethyl-5-phenylhydantoin
- 1-ethyl-2,5-dioxo-4-phenylimidazolidine
- 3-ethyl-5-phenyl-2,4-imidazolidinedione
- 3-Ethyl-5-phenyl-imidazolidine-2,4-dione
- 3-ethyl-5-phenylhydantoin
- 3-ethyl-5-phenylimidazolidin-2,4-dione
- Ethotoin
- Ethotoïne
- Ethotoinum
- Etotoina
Pharmacology
- Indication
For the control of tonic-clonic (grand mal) and complex partial (psychomotor) seizures.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Ethotoin is a hydantoin derivative and anticonvulsant. Ethotoin exerts an antiepileptic effect without causing general central nervous system depression. The mechanism of action is probably very similar to that of phenytoin. The latter drug appears to stabilize rather than to raise the normal seizure threshold, and to prevent the spread of seizure activity rather than to abolish the primary focus of seizure discharges.
- Mechanism of action
The mechanism of action is probably very similar to that of phenytoin. The latter drug appears to stabilize rather than to raise the normal seizure threshold, and to prevent the spread of seizure activity rather than to abolish the primary focus of seizure discharges. Ethotoin inhibits nerve impulses in the motor cortex by lowering sodium ion influx, limiting tetanic stimulation.
Target Actions Organism ASodium channel protein type 5 subunit alpha inhibitorHumans UNuclear receptor subfamily 1 group I member 2 activatorHumans - Absorption
Fairly rapidly absorbed, however, the extent of oral absorption is not known.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Hepatic. The drug exhibits saturable metabolism with respect to the formation of N-deethyl and p-hydroxyl-ethotoin, the major metabolites.
Hover over products below to view reaction partners
- Route of elimination
Not Available
- Half-life
3 to 9 hours
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Symptoms of overdose include drowsiness, loss of or impaired muscle coordination, nausea, visual disturbance, and, at very high doses, coma.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of adverse effects can be increased when Ethotoin is combined with 1,2-Benzodiazepine. Acenocoumarol The therapeutic efficacy of Acenocoumarol can be increased when used in combination with Ethotoin. Acetazolamide The risk or severity of adverse effects can be increased when Ethotoin is combined with Acetazolamide. Acetophenazine The risk or severity of adverse effects can be increased when Ethotoin is combined with Acetophenazine. Agomelatine The risk or severity of adverse effects can be increased when Ethotoin is combined with Agomelatine. Alfentanil The risk or severity of adverse effects can be increased when Ethotoin is combined with Alfentanil. Alimemazine The risk or severity of adverse effects can be increased when Ethotoin is combined with Alimemazine. Allantoin The therapeutic efficacy of Allantoin can be increased when used in combination with Ethotoin. Almotriptan The risk or severity of adverse effects can be increased when Ethotoin is combined with Almotriptan. Alosetron The risk or severity of adverse effects can be increased when Ethotoin is combined with Alosetron. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Take after a meal. This may reduce gastrointestinal upset.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Accenon (Dainippon Sumitomo) / Pegoanone
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Peganone Tablet 250 mg/1 Oral Lundbeck Inc. 1957-04-22 2013-04-22 US 
Peganone Tablet 250 mg/1 Oral RECORDATI RARE DISEASES, INC. 1957-04-22 2018-08-31 US Peganone Tablet 250 mg/1 Oral RECORDATI RARE DISEASES, INC. 1957-04-22 Not applicable US
Categories
- ATC Codes
- N03AB01 — Ethotoin
- Drug Categories
- Anti-epileptic Agent
- Anticonvulsants
- Cardiovascular Agents
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 Enzyme Inducers
- Decreased Central Nervous System Disorganized Electrical Activity
- Hydantoins
- Imidazoles
- Imidazolidines
- Membrane Transport Modulators
- Nervous System
- Sodium Channel Blockers
- Thyroxine-binding globulin substrates
- Voltage-Gated Sodium Channel Blockers
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound 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
- Phenylimidazolidines / Alpha amino acids and derivatives / N-acyl ureas / Benzene and substituted derivatives / Dicarboximides / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives show 1 more
- Substituents
- 5-phenylhydantoin / Alpha-amino acid or derivatives / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonic acid derivative / Carbonyl group / Carboxylic acid derivative / Dicarboximide / Hydrocarbon derivative show 11 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- imidazolidine-2,4-dione (CHEBI:4888)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 46QG38NC4U
- CAS number
- 86-35-1
- InChI Key
- SZQIFWWUIBRPBZ-UHFFFAOYSA-N
- InChI
- InChI=1S/C11H12N2O2/c1-2-13-10(14)9(12-11(13)15)8-6-4-3-5-7-8/h3-7,9H,2H2,1H3,(H,12,15)
- IUPAC Name
- 3-ethyl-5-phenylimidazolidine-2,4-dione
- SMILES
- CCN1C(=O)NC(C1=O)C1=CC=CC=C1
References
- Synthesis Reference
Close, W.J.; U.S. Patent 2,793,157; May 21, 1957; assigned to Abbott Laboratories.
- General References
- SCHWADE ED, RICHARDS RK, EVERETT GM: Peganone, a new antiepileptic drug. Dis Nerv Syst. 1956 May;17(5):155-8. [Article]
- External Links
- Human Metabolome Database
- HMDB0014892
- KEGG Drug
- D00708
- KEGG Compound
- C07839
- PubChem Compound
- 3292
- PubChem Substance
- 46504521
- ChemSpider
- 3176
- BindingDB
- 50239975
- 4136
- ChEBI
- 4888
- ChEMBL
- CHEMBL1095
- Therapeutic Targets Database
- DAP000512
- PharmGKB
- PA164768735
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Ethotoin
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Lundbeck inc
- Packagers
- Abbott Laboratories Ltd.
- Kaiser Foundation Hospital
- Lundbeck Inc.
- Dosage Forms
Form Route Strength Tablet Oral 250 mg/1 - Prices
Unit description Cost Unit Peganone 250 mg tablet 1.33USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 94 °C PhysProp water solubility 5280 mg/L Not Available logP 1.05 SANGSTER (1994) - Predicted Properties
Property Value Source Water Solubility 2.38 mg/mL ALOGPS logP 1.11 ALOGPS logP 1.07 Chemaxon logS -1.9 ALOGPS pKa (Strongest Acidic) 11.18 Chemaxon pKa (Strongest Basic) -8.4 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 49.41 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 55.05 m3·mol-1 Chemaxon Polarizability 20.99 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9936 Caco-2 permeable + 0.5629 P-glycoprotein substrate Non-substrate 0.592 P-glycoprotein inhibitor I Non-inhibitor 0.8358 P-glycoprotein inhibitor II Non-inhibitor 0.9401 Renal organic cation transporter Non-inhibitor 0.8532 CYP450 2C9 substrate Non-substrate 0.7507 CYP450 2D6 substrate Non-substrate 0.9115 CYP450 3A4 substrate Non-substrate 0.7383 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.914 CYP450 2D6 inhibitor Non-inhibitor 0.9619 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8591 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8483 Ames test Non AMES toxic 0.7056 Carcinogenicity Non-carcinogens 0.8655 Biodegradation Not ready biodegradable 0.8423 Rat acute toxicity 2.1653 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.886 hERG inhibition (predictor II) Non-inhibitor 0.8724
Spectra
- Mass Spec (NIST)
- Download (8.5 KB)
- Spectra
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Voltage-gated sodium channel activity involved in sa node cell action potential
- Specific Function
- This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the pr...
- Gene Name
- SCN5A
- Uniprot ID
- Q14524
- Uniprot Name
- Sodium channel protein type 5 subunit alpha
- Molecular Weight
- 226937.475 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Lenkowski PW, Ko SH, Anderson JD, Brown ML, Patel MK: Block of human NaV1.5 sodium channels by novel alpha-hydroxyphenylamide analogues of phenytoin. Eur J Pharm Sci. 2004 Apr;21(5):635-44. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Activator
- General Function
- Zinc ion binding
- Specific Function
- Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism an...
- Gene Name
- NR1I2
- Uniprot ID
- O75469
- Uniprot Name
- Nuclear receptor subfamily 1 group I member 2
- Molecular Weight
- 49761.245 Da
References
- Kobayashi K, Yamagami S, Higuchi T, Hosokawa M, Chiba K: Key structural features of ligands for activation of human pregnane X receptor. Drug Metab Dispos. 2004 Apr;32(4):468-72. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Serine-type endopeptidase inhibitor activity
- Specific Function
- Major thyroid hormone transport protein in serum.
- Gene Name
- SERPINA7
- Uniprot ID
- P05543
- Uniprot Name
- Thyroxine-binding globulin
- Molecular Weight
- 46324.12 Da
References
- CYTOMEL (liothyronine) FDA label [File]
Drug created at June 13, 2005 13:24 / Updated at March 03, 2023 17:38