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

• ChemBase ID: 1072
• Molecular Formular: C8H14N2O2
• Molecular Mass: 170.20896
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-(2-oxopyrrolidin-1-yl)butanamide
• IUPAC Traditional name: levetiracetam; (2R)-2-(2-oxopyrrolidin-1-yl)butanamide
• Brand Name: Keppra
• Synonyms: Levetiracetam [INN]; Levetiracetamum [INN-Latin]; Levitiracetam; levetiracetam; Levetiracetam; Etiracetam; Levetiracetam

Database IDs

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

CALCULATED PROPERTIES

JChem

• Acid pKa: 16.088663
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.59360605
• 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

ALOGPS 2.1

• Log P: -0.64
• LOG S: 0.24
• Solubility (Water): 2.98e+02 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): -0.6

Pharmacology Properties

• Mechanism of Action: Nootropic (cognition enhancer)

Product Information

• Application(s): Anticonvulsant; Used to treat epilepsy

DETAILS

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

REFERENCES

• 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)