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

• ChemBase编号: 1072
• 分子式: C8H14N2O2
• 平均质量: 170.20896
• 单一同位素质量: 170.1055277
• SMILES: O=C1N(CCC1)[C@H](CC)C(=O)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-/m1/s1
• InChIKey: HPHUVLMMVZITSG-ZCFIWIBFSA-N

名称和登记号

名称

• IUPAC标准名: (2R)-2-(2-oxopyrrolidin-1-yl)butanamide
• IUPAC传统名: levetiracetam; (2R)-2-(2-oxopyrrolidin-1-yl)butanamide
• 商标名: Keppra
• 别名: Levetiracetam [INN]; Levetiracetamum [INN-Latin]; Levitiracetam; levetiracetam; Levetiracetam; Etiracetam; Levetiracetam

登记号

• CAS号: 102767-28-2
• PubChem SID: 160964535; 46508406
• PubChem CID: 441341

理论计算性质

JChem

• Acid pKa: 16.088663
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): -0.59360605
• 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

ALOGPS 2.1

• Log P: -0.64
• LOG S: 0.24
• 溶解度: 2.98e+02 g/l

分子性质

理化性质

• 疏水性(logP): -0.6

药理学性质

• 生物活性机理: Nootropic (cognition enhancer)

产品相关信息

• 应用领域: Anticonvulsant; Used to treat epilepsy

详细说明

DrugBank - DB01202

• Drug Groups: approved; investigational
• Description: Levetiracetam is an anticonvulsant medication used to treat epilepsy. Levetiracetam may selectively prevent hypersynchronization of epileptiform burst firing and propagation of seizure activity. Levetiracetam binds to the synaptic vesicle protein SV2A, which is thought to be involved in the regulation of vesicle exocytosis. Although the molecular significance of levetiracetam binding to synaptic vesicle protein SV2A is not understood, levetiracetam and related analogs showed a rank order of affinity for SV2A which correlated with the potency of their antiseizure activity in audiogenic seizure-prone mice.
• Indication: Used as adjunctive therapy in the treatment of partial onset seizures in adults and children 4 years of age and older with epilepsy.
• Toxicity: Side effects include aggression, agitation, coma, drowsiness, reduced consciousness, slowed breathing
• Affected Organisms: Humans and other mammals
• Biotransformation: The major metabolic pathway of levetiracetam (24% of dose) is an enzymatic hydrolysis of the acetamide group. No CYP450 metabolism detected.
• Absorption: Rapidly and almost completely absorbed after oral administration (99%). Peak plasma concentrations occurring in about an hour following oral administration in fasted subjects.
• Half Life: 6-8 hours
• Protein Binding: Very low (<10%)
• Elimination: Sixty-six percent (66%) of the dose is renally excreted unchanged. The metabolites have no known pharmacological activity and are renally excreted. The mechanism of excretion is glomerular filtration with subsequent partial tubular reabsorption.
• Clearance: * 0.96 mL/min/kg
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

参考文献

• Belg. Pat., 1971, Union Chim-Chem Bedrijven, 762 728; CA, 77, 114240y, (synth)
• Giurgea, C., Dev. Psychiatry, 1978, 2, 876, (rev, pharmacol)
• Wolthuis, O.L., Pharmacol., Biochem. Behav., 1981, 15, 247, (pharmacol)
• Eur. Pat., 1985, UCB, 165 919; CA, 105, 97305a, (synth, resoln)
• U.K. Pat., 1990, UCB, 2 225 322; CA, 113, 191151j, (S-form, synth)
• Lscher, W. et al., Eur. J. Pharmacol., 1993, 232, 147, (pharmacol)
• Gouliaev, A.H. et al., Brain Res. Brain Res. Rev., 1994, 19, 180, (rev)
• Loscher, W. et al., J. Pharmacol. Exp. Ther., 1998, 284, 474-479, (levetiracetam)
• Dooley, M. et al., Drugs, 2000, 60, 871-893, (levetiracetam, rev)
• Jain, K.K. et al., Expert Opin. Invest. Drugs, 2000, 9, 1611-1624, (levetiracetam)
• Patsalos, P.N. et al., Pharmacol. Ther., 2000, 85, 77-85, (levetiracetam)