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N-Phenylacetyl-L-prolylglycine ethyl ester

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N-Phenylacetyl-L-prolylglycine ethyl ester
Legal status
Legal status
  • In general: legal
Identifiers
IUPAC name
  • N-phenylacetyl-L-prolylglycine ethyl ester
CAS Number
PubChem CID
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H22N2O4
Molar mass318.367 g/mol g·mol
3D model (JSmol)
SMILES
  • c2ccccc2CC(=O)N1CCCC1C(=O)NCC(=O)OCC
  (verify)

Noopept (Template:Lang-ru; GVS-111, N-phenylacetyl-L-prolylglycine ethyl ester) is a medication promoted and prescribed in Russia and neighbouring countries as a nootropic remedy. It is derived from the racetam family of drugs and shares similar mechanisms of action, but is up to 1000 times more potent than the prototypical racetam drug, piracetam. Animal studies have shown noopept to be neuroprotective and enhance memory in various different tests. Unusually for a peptide-derived compound, noopept displays both high oral bioavailability and good blood-brain barrier penetration, and human studies have shown promising results, with potential application in the treatment of Alzheimer's disease.

References

  1. Solntseva EI, Bukanova JV, Ostrovskaya RU, Gudasheva TA, Voronina TA, Skrebitsky VG. The effects of piracetam and its novel peptide analogue GVS-111 on neuronal voltage-gated calcium and potassium channels. General Pharmacology. 1997 Jul;29(1):85-9. PMID 9195198
  2. Gudasheva TA, Boyko SS, Ostrovskaya RU, Voronina TA, Akparov VK, Trofimov SS, Rozantsev GG, Skoldinov AP, Zherdev VP, Seredenin SB. The major metabolite of dipeptide piracetam analogue GVS-111 in rat brain and its similarity to endogenous neuropeptide cyclo-L-prolylglycine. European Journal of Drug Metabolism and Pharmacokinetics. 1997 Jul-Sep;22(3):245-52. PMID 9358206
  3. Ostrovskaia RU, Gudasheva TA, Voronina TA, Seredenin SB (2002). "". Eksp Klin Farmakol (in Russian). 65 (5): 66–72. PMID 12596521.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. Ostrovskaya RU, Romanova GA, Barskov IV, Shanina EV, Gudasheva TA, Victorov IV, Voronina TA, Seredenin SB. Memory restoring and neuroprotective effects of the proline-containing dipeptide, GVS-111, in a photochemical stroke model. Behavioural Pharmacology. 1999 Sep;10(5):549-53. PMID 10780261
  5. Pelsman A, Hoyo-Vadillo C, Gudasheva TA, Seredenin SB, Ostrovskaya RU, Busciglio J. GVS-111 prevents oxidative damage and apoptosis in normal and Down's syndrome human cortical neurons. International Journal of Developmental Neuroscience. 2003 May;21(3):117-24. PMID 12711349
  6. Ostrovskaya RU, Gruden MA, Bobkova NA, Sewell RD, Gudasheva TA, Samokhin AN, Seredinin SB, Noppe W, Sherstnev VV, Morozova-Roche LA. The nootropic and neuroprotective proline-containing dipeptide noopept restores spatial memory and increases immunoreactivity to amyloid in an Alzheimer's disease model. Journal of Psychopharmacology. 2007 Aug;21(6):611-9. PMID 17092975
  7. Ostrovskaya RU, Gudasheva TA, Zaplina AP, Vahitova JV, Salimgareeva MH, Jamidanov RS, Seredenin SB. Noopept stimulates the expression of NGF and BDNF in rat hippocampus. Bulletin of Experimental Biology and Medicine. 2008 Sep;146(3):334-7.PMID: 19240853
  8. Boiko SS, Ostrovskaya RU, Zherdev VP, Korotkov SA, Gudasheva TA, Voronina TA, Seredenin SB. Pharmacokinetics of new nootropic acylprolyldipeptide and its penetration across the blood-brain barrier after oral administration. Bulletin of Experimental Biology and Medicine. 2000 Apr;129(4):359-61. PMID 10977920
  9. Ostrovskaya RU, Mirsoev TK, Romanova GA, Gudasheva TA, Kravchenko EV, Trofimov CC, Voronina TA, Seredenin SB. Proline-containing dipeptide GVS-111 retains nootropic activity after oral administration. Bulletin of Experimental Biology and Medicine. 2001 Oct;132(4):959-62. PMID 11782792
  10. Neznamov GG, Teleshova ES. Comparative studies of Noopept and piracetam in the treatment of patients with mild cognitive disorders in organic brain diseases of vascular and traumatic origin. Neuroscience and Behavioural Physiology. 2009 Mar;39(3):311-21. PMID 19234797
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Racetams
Racetams
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