3-ethyl-3-methylpyrrolidine-2,5-dione

• ChemBase ID: 475
• Molecular Formular: C7H11NO2
• Molecular Mass: 141.16774
• Monoisotopic Mass: 141.0789786
• SMILES: O=C1NC(=O)CC1(CC)C
• Canonical SMILES: CC1(CC)CC(=O)NC1=O
• InChI: InChI=1S/C7H11NO2/c1-3-7(2)4-5(9)8-6(7)10/h3-4H2,1-2H3,(H,8,9,10)
• InChIKey: HAPOVYFOVVWLRS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-ethyl-3-methylpyrrolidine-2,5-dione
• IUPAC Traditional name: 2-ethyl-2-methylsuccinimide; ethosuximide
• Brand Name: Asamid; Atysmal; Capitus; Emeside; Epileo Petit Mal; Ethymal; Etomal; Mesentol; Pemal; Pemalin; Pentinimid; Peptinimid; Petinimid; Petnidan; Piknolepsin; Pyknolepsinum; Ronton; Simatin; Succimal; Succimitin; Suxilep; Suximal; Suxin; Suxinutin; Thetamid; Thilopemal; Zaraondan; Zarodan; Zarondan; Zarontin; Zartalin
• Synonyms: Ethosuccimide; Ethosuccinimide; Ethosuxide; Etosuximida; Aethosuximide; Ethosuximide; 3-Ethyl-3-methyl-2,5-pyrrolidinedione; Atysmal; Capitus; Emeside; Etosuximid; H 940; Mesentol; NSC 64013; Simatin; Succimal; Succimitin; Suxilep; Suximal; 3-ethyl-3-methylpyrrolidine-2,5-dione; 2-Ethyl-2-methylsuccinimide; Ethosuximide

Database IDs

• CAS Number: 77-67-8
• EC Number: 201-048-7
• MDL Number: MFCD00072123
• PubChem SID: 46507617; 160963938; 24278423
• PubChem CID: 3291
• CHEBI ID: 4887
• ATC CODE: N03AD01
• CHEMBL: 696
• Chemspider ID: 3175
• DrugBank ID: DB00593
• KEGG ID: D00539
• Unique Ingredient Identifier: 5SEH9X1D1D
• Wikipedia Title: Ethosuximide
• Medline Plus: a682327

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.726963
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.55009514
• LogD (pH = 7.4): 0.5498955
• Log P: 0.5500977
• Molar Refractivity: 35.9579 cm^3
• Polarizability: 14.211085 Å^3
• Polar Surface Area: 46.17 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.1
• LOG S: -0.15
• Solubility (Water): 1.01e+02 g/l

PROPERTIES

Physical Property

• Solubility: 39.2 g/L; Chloroform; ethanol: soluble100 mg/mL; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 41-43°C; 51 - 53°C
• Hydrophobicity(logP): 0.1; 0.395

Safety Information

• Storage Condition: Refrigerator
• RTECS: WN2800000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: 93%
• Excretion: Renal (20%)
• Half Life: 53 hours
• Metabolism: Hepatic (CYP3A4, CYP2E1)
• Legal Status: ?-only (U.S.)
• Pregnancy Category: D (Australia, United States)
• Gene Information: human ... CACNA1G(8913)

Product Information

• Purity: 95%

DETAILS

DrugBank - DB00593

• Drug Groups: approved
• Description: An anticonvulsant especially useful in the treatment of absence seizures unaccompanied by other types of seizures. [PubChem]
• Indication: For the treatment of petit mal epilepsy.
• Pharmacology: Used in the treatment of epilepsy. Ethosuximide suppresses the paroxysmal three cycle per second spike and wave activity associated with lapses of consciousness which is common in absence (petit mal) seizures. The frequency of epileptiform attacks is reduced, apparently by depression of the motor cortex and elevation of the threshold of the central nervous system to convulsive stimuli.
• Toxicity: Acute overdoses may produce nausea, vomiting, and CNS depression including coma with respiratory depression.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic, via CYP3A4 and CYP2E1.
• Absorption: Bioavailability following oral administration is 93%.
• Half Life: 53 hours
• References: Patsalos PN: Properties of antiepileptic drugs in the treatment of idiopathic generalized epilepsies. Epilepsia. 2005;46 Suppl 9:140-8. [Pubmed] ; Coulter DA, Huguenard JR, Prince DA: Specific petit mal anticonvulsants reduce calcium currents in thalamic neurons. Neurosci Lett. 1989 Mar 13;98(1):74-8. [Pubmed] ; Coulter DA, Huguenard JR, Prince DA: Characterization of ethosuximide reduction of low-threshold calcium current in thalamic neurons. Ann Neurol. 1989 Jun;25(6):582-93. [Pubmed] ; Coulter DA, Huguenard JR, Prince DA: Differential effects of petit mal anticonvulsants and convulsants on thalamic neurones: calcium current reduction. Br J Pharmacol. 1990 Aug;100(4):800-6. [Pubmed] ; Kostyuk PG, Molokanova EA, Pronchuk NF, Savchenko AN, Verkhratsky AN: Different action of ethosuximide on low- and high-threshold calcium currents in rat sensory neurons. Neuroscience. 1992 Dec;51(4):755-8. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - E7138

Biochem/physiol Actions
Used for the treatment of absence-type seizures
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. E7138.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - E890440

Anticonvulsant.

REFERENCES

• Patsalos PN: Properties of antiepileptic drugs in the treatment of idiopathic generalized epilepsies. Epilepsia. 2005;46 Suppl 9:140-8. Pubmed
• Coulter DA, Huguenard JR, Prince DA: Specific petit mal anticonvulsants reduce calcium currents in thalamic neurons. Neurosci Lett. 1989 Mar 13;98(1):74-8. Pubmed
• Coulter DA, Huguenard JR, Prince DA: Characterization of ethosuximide reduction of low-threshold calcium current in thalamic neurons. Ann Neurol. 1989 Jun;25(6):582-93. Pubmed
• Coulter DA, Huguenard JR, Prince DA: Differential effects of petit mal anticonvulsants and convulsants on thalamic neurones: calcium current reduction. Br J Pharmacol. 1990 Aug;100(4):800-6. Pubmed
• Kostyuk PG, Molokanova EA, Pronchuk NF, Savchenko AN, Verkhratsky AN: Different action of ethosuximide on low- and high-threshold calcium currents in rat sensory neurons. Neuroscience. 1992 Dec;51(4):755-8. Pubmed
• Sato, S., et al.: Neurology, 32, 157 (1982)
• Wallance, S.J., et al.: Neurol. Clin., 4, 601 (1982)