Levetiracetam

Levetiracetam
Clinical data
Pronunciation/lɛvɪtɪˈræsɪtæm/
Trade namesKeppra, Elepsia, Spritam, others
AHFS/Drugs.comMonograph
MedlinePlusa699059
License data
Pregnancy
category
  • AU: B3
Routes of
administration
By mouth, intravenous
Drug classRacetam anticonvulsant
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • BR: Class C1 (Other controlled substances)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: ℞-only
  • EU: Rx-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability≈100%
Protein binding<10%
MetabolismEnzymatic hydrolysis of acetamide group
Elimination half-life6–8 hrs
ExcretionKidney
Identifiers
  • (S)-2-(2-Oxopyrrolidin-1-yl)butanamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.121.571
Chemical and physical data
FormulaC8H14N2O2
Molar mass170.212 g·mol−1
3D model (JSmol)
  • O=C1N([C@H](C(=O)N)CC)CCC1
  • 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 Y
  • Key:HPHUVLMMVZITSG-LURJTMIESA-N Y
 NY (what is this?)  (verify)

Levetiracetam, sold under the brand name Keppra among others, is a novel antiepileptic drug (medication) used to treat epilepsy. It is used for partial-onset, myoclonic, or tonic–clonic seizures, and is taken either by mouth as an immediate or extended release formulation or by injection into a vein.

Levetiracetam was discovered in 1992 through screening in audiogenic seizure susceptible mice and, 3 years later, was reported to exhibit saturable, stereospecific binding in brain to a approximately 90 kDa protein, later identified as the ubiquitous synaptic vesicle glycoprotein SV2A."

The discovery process identifying levetiracetam's antiepileptic potential was unique because it challenged several dogmas of antiepileptic drug discovery, and thereby encountered skepticism from the epilepsy community.

Common side effects of levetiracetam include sleepiness, dizziness, feeling tired, and aggression. Severe side effects may include psychosis, suicide, and allergic reactions such as Stevens–Johnson syndrome or anaphylaxis. Levetiracetam is the S-enantiomer of etiracetam. It acts as a synaptic vesicle glycoprotein 2A (SV2A) ligand.

Levetiracetam was approved for medical use in the United States in 1999 and is available as a generic medication. In 2022, it was the 123rd most commonly prescribed medication in the United States, with more than 5 million prescriptions. It is on the World Health Organization's List of Essential Medicines.