(2S)-2-(2-oxopyrrolidin-1-yl)butanamide

• ChemBase编号: 70537
• 分子式: C8H14N2O2
• 平均质量: 170.20896
• 单一同位素质量: 170.1055277
• SMILES: C(=O)([C@H](CC)N1C(=O)CCC1)N
• Canonical SMILES: CC[C@H](N1CCCC1=O)C(=O)N
• InChI: InChI=1S/C8H14N2O2/c1-2-6(8(9)12)10-5-3-4-7(10)11/h6H,2-5H2,1H3,(H2,9,12)/t6-/m0/s1
• InChIKey: HPHUVLMMVZITSG-LURJTMIESA-N

名称和登记号

名称

• IUPAC标准名: (2S)-2-(2-oxopyrrolidin-1-yl)butanamide
• IUPAC传统名: levetiracetam; @levetiracetam
• 商标名: Keppra
• 别名: (αS)-α-Ethyl-2-oxo-1-pyrrolidineacetamide; 2(S)-(2-oxopyrrolidin-1-yl)butyramide; Keppra®; Levetiracetam; (S)-2-(2-Oxopyrrolidin-1-yl)butanamide; (-)-Levetiracetam; Levesam 500; UCB-L 059; Keppra; Keppra XR; Levetiracetam

登记号

• CAS号: 102767-28-2
• MDL号: MFCD03265610
• PubChem SID: 162036252
• PubChem CID: 5284583
• ATC码: N03AX14
• CHEMBL: 1286
• Chemspider ID: 4447633
• DrugBank ID: DB01202
• KEGG ID: D00709
• 美国药典/FDA物质标识码: 44YRR34555
• 维基百科标题: Levetiracetam
• Medline Plus: a699059

理论计算性质

• Acid pKa: 16.088663
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): -0.59360594
• LogD (pH = 7.4): -0.5936059
• Log P: -0.5936059
• 摩尔折射率: 44.0793 cm^3
• 极化性: 17.197067 Å^3
• 极化表面积: 63.4 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Acetone; Chloroform; H2O: >5 mg/mL; Methanol
• 外观: white powder; White Solid
• 熔点: 110-112°C

安全信息

• 保存条件: -20°C; -20°C Freezer
• 保存注意事项: IRRITANT
• RTECS编号: UX9656166
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22-36
• 安全公开号: 26
• TSCA收录: false
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302-H319
• GHS警示性声明: P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

药理学性质

• 给药途径: Oral, intravenous
• 生物利用度: ~100%
• 排泄: Urinary
• 半衰期: 6 - 8 hr
• 代谢: Enzymatic hydrolysis of acetamide group
• 蛋白结合率: <10%
• 法定药品分级: rx-only
• 妊娠期药物分类: C (US)

产品相关信息

• 纯度: ≥98% (HPLC); 95+%
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C8H14N2O2

详细说明

Selleck Chemicals - S1356

Research Area: Neurological Disease
Biological Activity:
Levetiracetam is used to control some types of seizures in patients with epilepsy. This medicine cannot cure epilepsy and will only work to control seizures for as long as you continue to use it.The exact mechanism for levetiracetam is unknown. However, the drug binds to a synaptic vesicle protein, SV2A, which is believed to impede nerve conduction across synapses. [1]

Sigma Aldrich - L8668

Biochem/physiol Actions
Levetiracetam is a pyrrolidine with antiepileptic activity. Stereoselective binding of levetiracetam was confined to synaptic plasma membranes in the central nervous system with no binding occurring in peripheral tissue. Levetiracetam inhibits burst firing without affecting normal neuronal excitability, which suggests that it may selectively prevent hyper-synchronization of epileptiform burst firing and propagation of seizure activity.
法律信息
Keppra 注册商标 UCB Pharma, S.A.

Toronto Research Chemicals - L331500

The (S)-enantiomer of Etiracetam (E932970) and the ethyl analog of Piracetam (P500800). Used as an anticonvulsant.

参考文献

• http://www.rxlist.com/keppra-drug.htm
• Gower, A.J., et al.: Eur. J. Pharmacol., 222, 193 (1992)
• Kasteleijn-Noist Trenite, D.G.A., et al.: Epilepsy Res., 25, 225 (1992)
• Patsalos, P.N., et al.: Pharmacol. Ther., 85, 77 (1992)