Levetiracetam

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Cat Number

API102767282

CAS Number

102767-28-2

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Product Detail Description Scientific Support Customer Q&A

CAS Number

102767-28-2

EINECS

600-348-9

Storage

Store at room temperature

Synonyms

Keppra; (2S)-2-(2-oxopyrrolidin-1-yl)butanamide; Keppra XR; Spritam; UCB-L 059; matever; Levetiracetame; Levetiracetamum

Molecular Formula

C8H14N2O2

Molecular Weight

170.21

Smiles

CC[C@@H](C(=O)N)N1CCCC1=O

Appearance

White to off-white crystalline powder

Melting Point

118-119°C

Boiling Point

395.9°C at 760 mmHg

Relative Density

1.168

General Description

Levetiracetam is a synthetic pyrrolidine derivative with an acetamide side chain, structurally unrelated to other anticonvulsants. Its chemical structure is (S)-2-(2-oxopyrrolidin-1-yl)butanamide. The molecule has a chiral center, and the S-enantiomer is the pharmacologically active form.

Mechanism of Action

Levetiracetam binds to the synaptic vesicle protein 2A (SV2A), a transmembrane protein involved in the regulation of neurotransmitter release. This binding modulates neurotransmitter release and reduces the excitability of neurons. The drug also inhibits the high-voltage-activated calcium channels (N-type) and modulates the activity of GABA-A receptors, but the primary mechanism is through SV2A.

Application

Levetiracetam is indicated as an adjunctive therapy for partial-onset seizures, myoclonic seizures, and generalized tonic-clonic seizures in adults and children. It is also used for the treatment of epilepsy in patients with juvenile myoclonic epilepsy and for the management of status epilepticus.

In a phase 2 study, 73 patients with newly diagnosed glioblastoma received levetiracetam (1,000–2,000 mg/day) during concurrent chemoradiotherapy. Six-month progression-free survival (84.9% vs 72.3%, p=0.038) and 24-month overall survival (58.0% vs 39.9%, p=0.018) were improved vs external controls, though differences diminished in propensity-matched analysis. Subgroups <65 years or with unmethylated MGMT may benefit more.

Fig. 1 Kaplan–Meier curves for progression‐free and overall survival. (Hwang K,et al., 2022)

References

Hwang K, et al. Levetiracetam as a sensitizer of concurrent chemoradiotherapy in newly diagnosed glioblastoma: An open-label phase 2 study. Cancer Med. 2022;11(2):371-379.

Does Levetiracetam require protection from moisture during long-term storage?

It is slightly hygroscopic. Under high humidity (>70% RH), it may absorb moisture and clump, affecting flowability. Store in tightly sealed containers with desiccant.