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77-67-8 molecular structure
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3-ethyl-3-methylpyrrolidine-2,5-dione

ChemBase ID: 475
Molecular Formular: C7H11NO2
Molecular Mass: 141.16774
Monoisotopic Mass: 141.0789786
SMILES and InChIs

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

Cite this record

CBID:475 http://www.chembase.cn/molecule-475.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
77-67-8
EC Number
201-048-7
MDL Number
MFCD00072123
PubChem SID
46507617
24278423
160963938
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

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 10.726963  H Acceptors
H Donor LogD (pH = 5.5) 0.55009514 
LogD (pH = 7.4) 0.5498955  Log P 0.5500977 
Molar Refractivity 35.9579 cm3 Polarizability 14.211085 Å3
Polar Surface Area 46.17 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 0.1  LOG S -0.15 
Solubility (Water) 1.01e+02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
39.2 g/L expand Show data source
Chloroform expand Show data source
ethanol: soluble100 mg/mL expand Show data source
Methanol expand Show data source
Apperance
White to Off-White Solid expand Show data source
Melting Point
41-43°C expand Show data source
51 - 53°C expand Show data source
Hydrophobicity(logP)
0.1 expand Show data source
0.395 expand Show data source
Storage Condition
Refrigerator expand Show data source
RTECS
WN2800000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22 expand Show data source
Safety Statements
36 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Admin Routes
Oral expand Show data source
Bioavailability
93% expand Show data source
Excretion
Renal (20%) expand Show data source
Half Life
53 hours expand Show data source
Metabolism
Hepatic (CYP3A4, CYP2E1) expand Show data source
Legal Status
?-only (U.S.) expand Show data source
Pregnancy Category
D (Australia, United States) expand Show data source
Gene Information
human ... CACNA1G(8913) expand Show data source
Purity
95% expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00593 external link
Item Information
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 external link
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.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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