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102767-28-2 molecular structure
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(2R)-2-(2-oxopyrrolidin-1-yl)butanamide

ChemBase ID: 1072
Molecular Formular: C8H14N2O2
Molecular Mass: 170.20896
Monoisotopic Mass: 170.1055277
SMILES and InChIs

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

Cite this record

CBID:1072 http://www.chembase.cn/molecule-1072.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
102767-28-2
PubChem SID
160964535
46508406
PubChem CID
441341

DATA SOURCES

DATA SOURCES

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CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 16.088663  H Acceptors
H Donor LogD (pH = 5.5) -0.59360605 
LogD (pH = 7.4) -0.5936059  Log P -0.5936059 
Molar Refractivity 44.0793 cm3 Polarizability 17.197067 Å3
Polar Surface Area 63.4 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -0.64  LOG S 0.24 
Solubility (Water) 2.98e+02 g/l 

PROPERTIES

PROPERTIES

Physical Property Pharmacology Properties Product Information Bioassay(PubChem)
Hydrophobicity(logP)
-0.6 expand Show data source
Mechanism of Action
Nootropic (cognition enhancer) expand Show data source
Application(s)
Anticonvulsant expand Show data source
Used to treat epilepsy expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB01202 external link
Item Information
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
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REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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