Levetiracetam

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ImageFileL1 = levetiracetam.png ImageSizeL1 = 110px
ImageFileR1 = Levetiracetam3d.png ImageSizeR1 = 110px
ImageFile2 = levetiracetam.gif
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IUPACName = (2S)-2-(2-oxopyrrolidin-1-yl)butanamide
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Section1 = Chembox Identifiers
PubChem = 441341
CASNo = 102767-28-2
ATCCode_prefix = N03
ATCCode_suffix = AX14
SMILES = CC [C@@H] (C(=O)N)N1CCCC1=O
Section2 = Chembox Properties
Formula = | C=8 | H=14 | N=2 | O=2
MolarMass = 170.209 g/mol
Appearance = Fine white crystalline powder
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Section5 = Chembox Pharmacology
AdminRoutes = Oral, Intravenous
Bioavail = ~100%
Metabolism =
HalfLife = 6 - 8 hr
ProteinBound =
Excretion = Urinary
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Legal_US = POM
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PregCat_US = C

Levetiracetam (INN) (pronEng|lɛvɨtɪˈræsɨtæm) is an anticonvulsant medication used to treat epilepsy. It is "S"- enantiomer of etiracetam, structurally similar to the prototypical nootropic drug piracetam. Along with other anticonvulsants like gabapentin, it is also sometimes used to treat neuropathic pain. Levetiracetam is marketed under the trade name Keppra. Keppra is manufactured by UCB Pharmaceuticals Inc.

Levetiracetam has recently been approved in the United Kingdom as a monotherapy treatment for epilepsy. It is also used in veterinary medicine for similar purposes.

Mechanism

Levetiracetam binds to a synaptic vesicle protein, SV2A.cite journal | last=Lynch | first=BA | coauthors= Lambeng N, Nocka K | title=The synaptic vesicle protein SV2A is the binding site for the antiepileptic drug levetiracetam | journal=Proceedings of the National Academy of Sciences of the United States of America | volume=101 | issue=26 | pages=9861–9866 | publisher=The National Academy of Sciences | date=June 2004 | url=http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pubmed&pubmedid=15210974 | pmid=15210974 | doi=10.1073/pnas.0308208101 | accessdate=2008-07-21 ] This is believed to impede nerve conduction across synapses.cite journal | last=Rogawski | first=MA | title=Diverse mechanisms of antiepileptic drugs in the development pipeline | journal=Epilepsy Research | volume=69 | issue=3 | pages=273–294 | publisher=National Institutes of Health | date=June 2006 | url=http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pubmed&pubmedid=16621450 | pmid=16621450 | doi=10.1016/j.eplepsyres.2006.02.004 | accessdate=2008-07-21 ]

Side effects

Side effects include: hair loss; pins and needles sensation in the extremities; psychiatric symptoms ranging from irritability to depression; and other common side effects like headache and nausea. Recent literature [http://www.aesnet.org/Visitors/AnnualMeeting/Abstracts/dsp_Abstract.cfm?id=3367] (and paper 2.163 in [http://www.blackwell-synergy.com/doi/abs/10.1111/j.1528-1167.2005.460801_16.x] ) suggests that the addition of pyridoxine (vitamin B6) may curtail some of the psychiatric symptoms.

Levetiracetam is generally well tolerated but may cause sleepiness, weakness, dizziness, and infection. In children, the most common side effects are sleepiness, accidental injury, hostility, irritability, and weakness. [http://www.keppra.com/pc/home/default.asp]

References

* [http://www.fda.gov/cder/foi/label/1999/21035lbl.pdf Keppra (levetiracetam) Final Printed Label] New and Generic Drug Approvals. 29 Dec 1999. Center for Drug Evaluation and Research, U.S. Food and Drug Administration. Accessed 31 August 2005.
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External links

* [http://www.keppra.com/ Keppra UCB] (manufacturer's website)
* [http://www.nlm.nih.gov/medlineplus/druginfo/medmaster/a699059.html NIH MedLine drug information]

ee also

* Racetams