CAS 77-67-8|Piknolepsin|Suxinutin|Zaraondan|Ethosuximide|Suximal|Ethosuxide|Asamid|Zarontin|Petnidan|Pentinimid|3-ethyl-3-methylpyrrolidine-2,5-dione|Mesentol|Etomal|Capitus|Succimitin|Zartalin|2-et...

General Information

Structure

Molecular Formula

C₇H₁₁NO₂

Molecular Mass

141.16774

Exact Mass

141.0789786

Charge

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

Canonic Smiles

CC1(CC)CC(=O)NC1=O

Isomeric Smiles

O=C1NC(=O)CC1(CC)C

Calculated Properties

JChem

LogD (pH = 7.4)

0.55

LogD (pH = 5.5)

0.55

Log P

0.55

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

10.73

Polar Surface Area

46.17

Polarizability

14.47

Molar Refractivity

35.96

LOG S

-0.81

Data Source

Names and Identifiers

Brand Name

EthymalSuccimalPetnidanThetamidMesentolPentinimidSuxinutinPeptinimidSuximalEpileo Petit MalThilopemalRontonAsamidSuxinEtomalZarondanPemalinSimatinCapitusZaraondanSuxilepZarodanAtysmalSuccimitinZartalinPemalPyknolepsinumPiknolepsinZarontinEmesidePetinimid

Synonyms

EthosuximideEtosuximidaEthosuccimideEthosuccinimideEthosuxideAethosuximideEthosuximide2-Ethyl-2-methylsuccinimideNSC 64013SuximalSuccimalEmesideMesentolEtosuximid3-Ethyl-3-methyl-2,5-pyrrolidinedioneCapitusSuxilepSuccimitinAtysmalH 940Simatin3-ethyl-3-methylpyrrolidine-2,5-dione3-ethyl-3-methyl-2,5-pyrrolidinedioneEthosuximide3-methyl-3-ethylsuccinimide2-methyl-2-ethylsuccinimide3-methyl-3-ethylpyrrolidine-2,5-dionegamma-methyl-gamma-ethyl-succinimidealpha-methyl-alpha-ethylsuccinimideethosuximideAethosuximidealpha-ethyl-alpha-methylsuccinimidegamma-ethyl-gamma-methyl-succinimide3-ethyl-3-methylsuccinimide(+-)-2-ethyl-2-methylsuccinimide2-ethyl-2-methylsuccinimide

IUPAC Traditional name

2-ethyl-2-methylsuccinimide ethosuximide

IUPAC name

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

API Name

Ethosuximide

International Nonproprietary Name (INN)

ethosuximideetosuximidaethosuximidum

Names and Identifiers

Registration numbers

CAS Number

77-67-8

ATC CODE

N03AD01

Unique Ingredient Identifier

Chemspider ID

CHEMBL

Wikipedia Title

CHEBI ID

4887CHEBI:4887CHEBI:131811

PubChem CID

DrugBank ID

KEGG ID

Medline Plus

PubChem SID

242784234650761716096393899437356

MDL Number

MFCD00072123

EC Number

201-048-7

PubMed Citation Links

17011080190050612194579718949032166067601847429128735073336019170462483820228174818968691481174512322308142206192516811058246220229601621332949199214186276139016327

MetaboLights Database

MTBLS2081MTBLS867MTBLS392MTBLS1918MTBLS1693MTBLS2878MTBLS4967

KEGG DRUG Database

D00539

Reaxys Registry

117054

SureChEMBL Database

SCHEMBL34212SCHEMBL20541518

ACToR Database

77-67-8

BRENDA Database

1.1.1.21

BKMS React Database

97926

Drug Central Database

1,087

BRENDA Ligand Database

97926

LINCS Database

LSM-5195

HMDB Database

HMDB0014731

ArrayExpress (Gene Expression Altlas)

E-MTAB-3919

CompTox Database

DTXSID7023019

Registration numbers

Properties

Safety Information

WN2800000

Warning

H302

Harmful (Xn)

Product Information

Download link

95%

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule 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]

Wikipedia

Ethosuximide

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.

TRC

E890440

Anticonvulsant.

ChEBI

CHEBI:4887

A dicarboximide that is pyrrolidine-2,5-dione in which the hydrogens at position 3 are substituted by one methyl and one ethyl group. An antiepileptic, it is used in the treatment of absence seizures and may be used for myoclonic seizures, but is ineffective against tonic-clonic seizures.

Molecule Details

References

PubChem Literature

From Data Sources

• 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

• 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: Characterization of ethosuximide reduction of low-threshold calcium current in thalamic neurons. Ann Neurol. 1989 Jun;25(6):582-93. Pubmed

• Wallance, S.J., et al.: Neurol. Clin., 4, 601 (1982)

• Sato, S., et al.: Neurology, 32, 157 (1982)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Brand Name

Synonyms

IUPAC Traditional name

2-ethyl-2-methylsuccinimide ethosuximide

IUPAC name

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

API Name

Ethosuximide

International Nonproprietary Name (INN)

ethosuximideetosuximidaethosuximidum

Registration numbers

CAS Number

77-67-8

ATC CODE

N03AD01

Unique Ingredient Identifier

Chemspider ID

CHEMBL

Wikipedia Title

CHEBI ID

4887CHEBI:4887CHEBI:131811

PubChem CID

DrugBank ID

KEGG ID

Medline Plus

PubChem SID

242784234650761716096393899437356

MDL Number

MFCD00072123

EC Number

201-048-7

PubMed Citation Links

17011080190050612194579718949032166067601847429128735073336019170462483820228174818968691481174512322308142206192516811058246220229601621332949199214186276139016327

MetaboLights Database

MTBLS2081MTBLS867MTBLS392MTBLS1918MTBLS1693MTBLS2878MTBLS4967

KEGG DRUG Database

D00539

Reaxys Registry

117054

SureChEMBL Database

SCHEMBL34212SCHEMBL20541518

ACToR Database

77-67-8

BRENDA Database

1.1.1.21

BKMS React Database

97926

Drug Central Database

1,087

BRENDA Ligand Database

97926

LINCS Database

LSM-5195

HMDB Database

HMDB0014731

ArrayExpress (Gene Expression Altlas)

E-MTAB-3919

CompTox Database

DTXSID7023019

Molecule 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

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]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

E7138

E890440

Anticonvulsant.

ChEBI

CHEBI:4887

References

PubChem Literature

From Data Sources

• 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

• 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: Characterization of ethosuximide reduction of low-threshold calcium current in thalamic neurons. Ann Neurol. 1989 Jun;25(6):582-93. Pubmed

• Wallance, S.J., et al.: Neurol. Clin., 4, 601 (1982)

• Sato, S., et al.: Neurology, 32, 157 (1982)

Bioactivity

PubChem BioAssay

Properties

Safety Information

WN2800000

Warning

H302

Harmful (Xn)

Product Information

Download link

95%

Molecule

ID:475