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  • The Discovery and Development of Lacosamide (Vimpat®)

    A new investigative drug by the name of Lacosamide (LCM) is waiting for final approval from the FDA for use as an adjunctive treatment for the seizure disorder known as epilepsy. Although there are many variations of epilepsy, usually classified by the type of seizure experienced, a general description would be "a recurring periodic seizure disorder that arises from disregulated electrical and neuronal activity within the brain and results in the loss of mental awareness or consciousness, involuntary movement, or convulsion."1 (Molecules & Medicine)

    Lacosamide belongs to a category of drugs labeled as Functionalized Amino Acids. Until recently its mechanism of action was unknown. However, according to a recent article in CNS Drug Reviews, Lacosamide: A Review of Preclinical Properties, researchers have elucidated a "novel dual mechanism"2 consisting of selective enhancement of sodium channel slow inactivation and modulation of CRMP-2 (collapsin response mediator protein 2) activity.

    An on-going goal for the Epilepsy research community is the discovery and development of medications for those patients with intractable (treatment-resistant) epilepsy as well as medications that are well-tolerated and possess fewer side effects. Antiepileptic drugs are also used to treat other CNS disorders. LCM is also being investigated as a treatment for diabetic neuropathic pain and migraines. On November 29, 2007 UCB, a global biopharmaceutical company headquartered in Brussels Belgium, announced that a New Drug Application (NDA) had been submitted to the FDA for a New Chemical Entity (NCE) named Lacosamide for use as an adjunctive therapy in the Treatment of Partial Onset Seizures in Adults with Epilepsy. Prior to this announcement another clinical trial study was begun in August 2007 to evaluate the safety and efficacy of Lacosamide as a monotherapy treatment for epilepsy.
  • Background

  • Chemical Profile of Lacosamide (Vimpat)

    • Name: (2R)-2-(Acetylamino)-N-benzyl-3-methoxypropanamide
    • Chemical Class: Functionalized Amino Acids3
    • Stereochemistry: R enantiomer active; S enantiomer inactive
    • Synonyms: Harkoseride; ADD #234037; SPM 927; Lacosamide; Vimpat®
    • CAS RN: 175481-36-4
    • Mol. Wgt.: 250.296
    • Mol. Formula: C13-H18-N2-O3
    • Satisfies Lipinski's Rule of 5 for "drug likeness" [LogP (-5:5); HBA (<10); HBD (<5); MW (<500)]: (Caltech)
    • XLogP = 0.5; Hydrogen Bond Donor Count (HBD) = 2; Hydrogen Bond AcceptorCount (HBA) = 3
  • Learn more about Clinical Trials and the Drug Approval Process

  • References

    • Corey, E.J., Czakó, B., Kürti, L., 2007. Molecules and Medicine. John Wiley & Sons, Inc., Hoboken, NJ, pp. 226.
    • Beyreuther, B.K., Freitag, J., Heers, C., Krebsfänger, N., Scharfenecker, U., Stöhr, T., 2007.
      Lacosamide: A Review of Preclinical Properties. CNS Drug Reviews 13 21-42.
    • Rogawski, M.A., 2006. Diverse mechanisms of antiepileptic drugs in the development pipeline. Epilepsy Research 69 273-294.