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

• ChemBase ID: 70537
• Molecular Formular: C8H14N2O2
• Molecular Mass: 170.20896
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-(2-oxopyrrolidin-1-yl)butanamide
• IUPAC Traditional name: levetiracetam; @levetiracetam
• Brand Name: Keppra
• Synonyms: (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

Database IDs

• CAS Number: 102767-28-2
• MDL Number: MFCD03265610
• PubChem SID: 162036252
• PubChem CID: 5284583
• ATC CODE: N03AX14
• CHEMBL: 1286
• Chemspider ID: 4447633
• DrugBank ID: DB01202
• KEGG ID: D00709
• Unique Ingredient Identifier: 44YRR34555
• Wikipedia Title: Levetiracetam
• Medline Plus: a699059

CALCULATED PROPERTIES

• Acid pKa: 16.088663
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.59360594
• LogD (pH = 7.4): -0.5936059
• Log P: -0.5936059
• Molar Refractivity: 44.0793 cm^3
• Polarizability: 17.197067 Å^3
• Polar Surface Area: 63.4 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; H2O: >5 mg/mL; Methanol
• Apperance: white powder; White Solid
• Melting Point: 110-112°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• Storage Warning: IRRITANT
• RTECS: UX9656166
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36
• Safety Statements: 26
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Admin Routes: Oral, intravenous
• Bioavailability: ~100%
• Excretion: Urinary
• Half Life: 6 - 8 hr
• Metabolism: Enzymatic hydrolysis of acetamide group
• Protein Bound: <10%
• Legal Status: rx-only
• Pregnancy Category: C (US)

Product Information

• Purity: ≥98% (HPLC); 95+%
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C8H14N2O2

DETAILS

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.

Toronto Research Chemicals - L331500

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

REFERENCES

• 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)