Aniracetam

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Aniracetam
Aniracetam.svg
Aniracetam3d.png
Clinical data
Trade names Ampamet, Memodrin, Pergamid
AHFS/Drugs.com International Drug Names
Routes of
administration
By mouth
ATC code
Legal status
Legal status
  • US: Not approved
  • In general: unscheduled
Pharmacokinetic data
Biological half-life 1–2.5 hours
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard 100.108.230
Chemical and physical data
Formula C12H13NO3
Molar mass 219.237 g/mol
3D model (Jmol)
 NYesY (what is this?)  (verify)

Aniracetam (Draganon, Sarpul, Ampamet, Memodrin, Referan), also known as N-anisoyl-2-pyrrolidinone, is an ampakine compound of the racetam chemical class. It is sold in Europe as a prescription drug, but it is not approved by the Food and Drug Administration for use in the United States.[1]

Pharmacology[edit]

Aniracetam has also been shown to positively modulate the AMPA receptor.[2]

When ingested orally aniracetam is quickly broken down via first pass hepatic metabolism. The primary metabolites of aniracetam are N-anisoyl-GABA, (70–80%), 2-Pyrrolidinone and p-anisic acid (20–30%).[3][4][5]

Plasma concentrations are generally in the 5–15 μg/L range for aniracetam and 5–15 mg/L range for N-anisoyl-GABA, a pharmacologically-active metabolite, during the first few hours after oral administration of the drug. These two plasma species may be measured by liquid chromatography-mass spectrometry.[6][7][8]

Synthesis[edit]

The drug was first made in the 1970s by Hoffmann-La Roche.[9][full citation needed][10][full citation needed] Synthesis can be accomplished by reacting 2-pyrrolidone with anisoyl chloride in the presence of triethylamine.[11]

Aniracetam synthesis 01.svg

Alternatively, gamma-aminobutyric acid can react with anisoyl chloride. Ring closure can be accomplished in the presence of thionyl chloride.[11]

Aniracetam synthesis 02.svg


References[edit]

  1. ^ Malykh AG; Sadaie MR (Feb 2010). "Piracetam and piracetam-like drugs: from basic science to novel clinical applications to CNS disorders.". Drugs. 70 (3): 287–312. doi:10.2165/11319230-000000000-00000. PMID 20166767. 
  2. ^ Ito; Tanabe, S; Kohda, A; Sugiyama, H; et al. (1990). "Allosteric potentiation of quisqualate receptors by a nootropic drug aniracetam". J. Physiol. 424: 533–543. PMC 1189827Freely accessible. PMID 1975272. 
  3. ^ Lee, CR; Benfield, P (1994). "Aniracetam. An overview of its pharmacodynamic and pharmacokinetic properties, and a review of its therapeutic potential in senile cognitive disorders". Drugs & aging. 4 (3): 257–73. doi:10.2165/00002512-199404030-00007. PMID 8199398. 
  4. ^ Schizophrenia: New Insights for the Healthcare Professional: 2013 Edition. ScholarlyEditions. 22 July 2013. pp. 152–. ISBN 978-1-4816-6196-6. 
  5. ^ Bernard Testa; Joachim M. Mayer (1 August 2003). Hydrolysis in Drug and Prodrug Metabolism. John Wiley & Sons. pp. 109–. ISBN 978-3-906390-25-3. 
  6. ^ Cai S, Wang L. Determination of aniracetam's main metabolite, N-anisoyl-GABA, in human plasma by LC-MS/MS and its application to a pharmacokinetic study. J. Chromatogr. B 897: 50-54, 2012.
  7. ^ Zhang J, Liang J, Tian Y, et al. Sensitive and selective liquid chromatography-tandem mass spectrometry method for the quantification of aniracetam in human plasma. J. Chromatogr. B 858: 129-134, 2007.
  8. ^ R. Baselt, Disposition of Toxic Drugs and Chemicals in Man, 10th edition, Biomedical Publications, Seal Beach, CA, 2014, p. 142-143.
  9. ^ Patent EP 5 143 Hoffmann-La Roche 1978
  10. ^ Patent EP 44 088 Hoffmann-La Roche 1978
  11. ^ a b A. Kleemann, J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances - Synthesis, Patents, Applications, 4. Auflage, Thieme 2001, ISBN 3-13-115134-X.