Levetiracetam molecular structure

Levetiracetam

Keppra, Elepsia, Spritam (CAS 102767-28-2)

Levetiracetam is a clinically essential anticonvulsant racetam, used worldwide as Keppra and generics, indicated for various seizure types. Its action as an SV2A ligand is pharmacologically distinct among antiepileptics.

Also known as:

KeppraSpritamElepsia

Formula

C₈H₁₄N₂O₂

Category

Racetam / Anticonvulsant

Half-Life

6–8 hrs

Legal Status

Rx Only (US/EU/AU/CA/UK/...)

Chemical Profile

IUPAC Name:Unspecified
Molecular Formula:C₈H₁₄N₂O₂
Structure:S-enantiomer of etiracetam
PubChem:5284583
DrugBank:DB01202
Molar Mass:170.21 g/mol
Bioavailability: ≈100%
Chirality:S (+) enantiomer
Origin:UCB Pharma, 1990s

Mechanism of Action

Unlike earlier racetams, levetiracetam acts primarily as a selective SV2A ligand: a synaptic vesicle protein involved in neuronal exocytosis and neurotransmitter release. This modulation is associated with a reduction in seizure activity and distinguishes levetiracetam pharmacologically from classic GABAergics and sodium channel blockers.

Multiple clinical and animal studies confirm distinctive SV2A-dependent anticonvulsant effects.

Preclinical & Clinical Evidence

SV2A Binding and Animal Research

Levetiracetam shows saturable, high affinity, stereospecific SV2A binding in mouse and human brain—and robust protection in genetic/induced seizure models.

Monotherapy and Add-on in Focal, Myoclonic, and Generalized Epilepsy

Extensive high-quality clinical evidence supports levetiracetam for monotherapy and adjunct use in partial, myoclonic, and tonic-clonic seizures in both adults and children; effectiveness and tolerability are generally high.

Other Confirmed Uses and Systematic Reviews

Effective as adjunct in myoclonic/tonic-clonic/generalized epilepsies, and in some cases of status epilepticus, with comparable or improved safety over alternatives.

Safety & Side Effects

Common reactions include fatigue, somnolence, dizziness, headache, and (esp. in children/adolescents) mood or behavioral symptoms. Severe/rare reactions: psychosis, suicidality, SJS/TEN, rash.

Well-characterized safety profile, >20 years clinical use

Regulatory & Legal Status

Global

  • Rx only in all major jurisdictions (US, EU, CA, UK, AU, JP...)
  • Listed as S4 in Australia, Rx only/controlled in many regions
  • WHO Essential Medicines, >5 million US scripts/yr (2022)

Note: Levetiracetam is by prescription only; no OTC or supplement sale permitted.

History

Levetiracetam was discovered by UCB Pharma in the early 1990s via genetic seizure model screens, and later identified as the S-enantiomer of etiracetam. Approved US/Europe 1999–2000, now global first-line for epilepsy.

1992
Discovery (UCB, Belgium)
1999
FDA/EMA Approval
2024
Top global antiepileptic
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Benefits

  • First-in-class SV2A ligand anticonvulsant
  • Wide spectrum: focal, myoclonic, generalized seizures
  • Favorable safety/tolerability, generic availability

Considerations

  • Prescription-only worldwide
  • Behavioral/psychiatric adverse effects possible
  • Not a cognitive enhancer: for epilepsy
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