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

• ChemBase编号: 475
• 分子式: C7H11NO2
• 平均质量: 141.16774
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 3-ethyl-3-methylpyrrolidine-2,5-dione
• IUPAC传统名: 2-ethyl-2-methylsuccinimide; ethosuximide
• 商标名: 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
• 别名: 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

登记号

• CAS号: 77-67-8
• EC号: 201-048-7
• MDL号: MFCD00072123
• PubChem SID: 46507617; 160963938; 24278423
• PubChem CID: 3291
• CHEBI ID: 4887
• ATC码: N03AD01
• CHEMBL: 696
• Chemspider ID: 3175
• DrugBank ID: DB00593
• KEGG ID: D00539
• 美国药典/FDA物质标识码: 5SEH9X1D1D
• 维基百科标题: Ethosuximide
• Medline Plus: a682327

理论计算性质

JChem

• Acid pKa: 10.726963
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 0.55009514
• LogD (pH = 7.4): 0.5498955
• Log P: 0.5500977
• 摩尔折射率: 35.9579 cm^3
• 极化性: 14.211085 Å^3
• 极化表面积: 46.17 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.1
• LOG S: -0.15
• 溶解度: 1.01e+02 g/l

分子性质

理化性质

• 溶解度: 39.2 g/L; Chloroform; ethanol: soluble100 mg/mL; Methanol
• 外观: White to Off-White Solid
• 熔点: 41-43°C; 51 - 53°C
• 疏水性(logP): 0.1; 0.395

安全信息

• 保存条件: Refrigerator
• RTECS编号: WN2800000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22
• 安全公开号: 36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

药理学性质

• 给药途径: Oral
• 生物利用度: 93%
• 排泄: Renal (20%)
• 半衰期: 53 hours
• 代谢: Hepatic (CYP3A4, CYP2E1)
• 法定药品分级: ?-only (U.S.)
• 妊娠期药物分类: D (Australia, United States)
• 相关基因信息: human ... CACNA1G(8913)

产品相关信息

• 纯度: 95%

详细说明

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.

参考文献

• 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)