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RESULTS [51 .. 101]
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Sunifiram
Sunifiram.png
Systematic (IUPAC) name
1-benzoyl-4-propanoylpiperazine
Clinical data
Legal status ?
Identifiers
CAS number 314728-85-3 YesY
ATC code ?
PubChem CID 4223812
ChEMBL CHEMBL309176 N
Chemical data
Formula C14H18N2O2 
Mol. mass 246.304 g/mol
 N (what is this?)  (verify)

Sunifiram (DM-235) is a piperazine derived ampakine-like drug[1] which has nootropic effects in animal studies with significantly higher potency than piracetam.[2][3] A number of related compounds are known, including unifiram (DM-232).[4][5][6]

Mechanisms of action[edit]

  1. Sunifiram activates AMPA-mediated neurotransmission.[7]
  2. It enhances LTP in a bell-shaped dose–response relationship. This enhancement by sunifiram is associated with an increase in phosphorylation of AMPAR through activation of protein kinase II (CaMKII) and an increase in phosphorylation of NMDAR through activation of protein kinase C α (PKCα). More specifically, sunifiram stimulates the glycine-binding site of NMDAR with concomitant PKCα activation through Src kinase. Enhancement of PKCα activity triggers hippocampal LTP through CaMKII activation.[8]
  3. Sunifiram improves cognitive deficits via CaM kinase II and protein kinase C activation.[9] PKC activation may be a common mechanism amongst cognition stimulating drugs from different chemical classes.[10]
  4. Sunifiram aids in the release of acetylcholine in the cerebral cortex.[11]

Safety[edit]

As of 2013, no formal human studies with sunifiram have been conducted.

Sunifiram, like galantamine,[12] activates PKC-α.[8]

Alternatives[edit]

Nefiracetam is a drug with similar effects.[13] Lithium potentiates AMPAR[14] and LTP[15][16][17] while inactivating Src kinase[18] and protecting[18][19][20][21] against NMDAR excitotoxicity.

See also[edit]

References[edit]

  1. ^ Galeotti, N.; Ghelardini, C.; Pittaluga, A.; Pugliese, A.; Bartolini, A.; Manetti, D.; Romanelli, M.; Gualtieri, F. (2003). "AMPA-receptor activation is involved in the antiamnesic effect of DM 232 (unifiram) and DM 235 (sunifiram)". Naunyn-Schmiedeberg's archives of pharmacology 368 (6): 538–545. doi:10.1007/s00210-003-0812-6. PMID 14600801.  edit
  2. ^ Ghelardini, C.; Galeotti, N.; Gualtieri, F.; Romanelli, M.; Bucherelli, C.; Baldi, E.; Bartolini, A. (2002). "DM235 (sunifiram): a novel nootropic with potential as a cognitive enhancer". Naunyn-Schmiedeberg's archives of pharmacology 365 (6): 419–426. doi:10.1007/s00210-002-0577-3. PMID 12070754.  edit
  3. ^ Romanelli, M.; Galeotti, N.; Ghelardini, C.; Manetti, D.; Martini, E.; Gualtieri, F. (2006). "Pharmacological characterization of DM232 (unifiram) and DM235 (sunifiram), new potent cognition enhancers". CNS Drug Reviews 12 (1): 39–52. doi:10.1111/j.1527-3458.2006.00039.x. PMID 16834757.  edit
  4. ^ Scapecchi, S.; Martini, E.; Manetti, D.; Ghelardini, C.; Martelli, C.; Dei, S.; Galeotti, N.; Guandalini, L.; Novella Romanelli, M.; Teodori, E. (2004). "Structure-activity relationship studies on unifiram (DM232) and sunifiram (DM235), two novel and potent cognition enhancing drugs". Bioorganic & Medicinal Chemistry 12 (1): 71–85. doi:10.1016/j.bmc.2003.10.025. PMID 14697772.  edit
  5. ^ Martini, E.; Ghelardini, C.; Dei, S.; Guandalini, L.; Manetti, D.; Melchiorre, M.; Norcini, M.; Scapecchi, S.; Teodori, E.; Romanelli, M. N. (2008). "Design, synthesis and preliminary pharmacological evaluation of new piperidine and piperazine derivatives as cognition-enhancers". Bioorganic & Medicinal Chemistry 16 (3): 1431–1443. doi:10.1016/j.bmc.2007.10.050. PMID 17981042.  edit
  6. ^ Martini, E.; Norcini, M.; Ghelardini, C.; Manetti, D.; Dei, S.; Guandalini, L.; Melchiorre, M.; Pagella, S.; Scapecchi, S.; Teodoria, E. (2008). "Design, synthesis and preliminary pharmacological evaluation of new analogues of DM232 (unifiram) and DM235 (sunifiram) as cognition modulators". Bioorganic & Medicinal Chemistry 16 (23): 10034–10042. doi:10.1016/j.bmc.2008.10.017. PMID 18954993.  edit
  7. ^ Galeotti, N.; Ghelardini, C.; Pittaluga, A.; Pugliese, A.; Bartolini, A.; Manetti, D.; Romanelli, M.; Gualtieri, F. (2003). "AMPA-receptor activation is involved in the antiamnesic effect of DM 232 (unifiram) and DM 235 (sunifiram)". Naunyn-Schmiedeberg's archives of pharmacology 368 (6): 538–545. doi:10.1007/s00210-003-0812-6. PMID 14600801.  edit
  8. ^ a b Moriguchi, S.; Tanaka, T.; Narahashi, T.; Fukunaga, K. (2013). "Novel nootropic drug sunifiram enhances hippocampal synaptic efficacy via glycine binding site of N-methyl-D-aspartate receptor". Hippocampus. doi:10.1002/hipo.22150. PMID 23733502.  edit
  9. ^ Moriguchi, S.; Tanaka, T.; Tagashira, H.; Narahashi, T.; Fukunaga, K. (2013). "Novel nootropic drug sunifiram improves cognitive deficits via CaM kinase II and protein kinase C activation in olfactory bulbectomized mice". Behavioural Brain Research 242: 150–157. doi:10.1016/j.bbr.2012.12.054. PMID 23295391.  edit
  10. ^ Lucchi, L.; Pascale, A.; Battaini, F.; Govoni, S.; Trabucchi, M. (1993). "Cognition stimulating drugs modulate protein kinase C activity in cerebral cortex and hippocampus of adult rats". Life sciences 53 (24): 1821–1832. doi:10.1016/0024-3205(93)90490-T. PMID 8246681.  edit
  11. ^ Manetti, D.; Ghelardini, C.; Bartolini, A.; Dei, S.; Galeotti, N.; Gualtieri, F.; Romanelli, M. N.; Teodori, E. (2000). "Molecular simplification of 1,4-diazabicyclo4.3.0nonan-9-ones gives piperazine derivatives that maintain high nootropic activity". Journal of medicinal chemistry 43 (23): 4499–4507. doi:10.1021/jm000972h. PMID 11087574.  edit
  12. ^ Moriguchi, S.; Shioda, N.; Han, F.; Yeh, J. Z.; Narahashi, T.; Fukunaga, K. (2009). "Galantamine enhancement of long-term potentiation is mediated by calcium/calmodulin-dependent protein kinase II and protein kinase C activation". Hippocampus 19 (9): 844–854. doi:10.1002/hipo.20572. PMID 19253410.  edit
  13. ^ Moriguchi, S.; Shioda, N.; Han, F.; Narahashi, T.; Fukunaga, K. (2008). "CaM kinase II and protein kinase C activations mediate enhancement of long-term potentiation by nefiracetam in the rat hippocampal CA1 region". Journal of neurochemistry 106 (3): 1092–1103. doi:10.1111/j.1471-4159.2008.05440.x. PMID 18445137.  edit
  14. ^ Gebhardt, C.; Cull-Candy, S. G. (2010). "Lithium acts as a potentiator of AMPAR currents in hippocampal CA1 cells by selectively increasing channel open probability". The Journal of Physiology 588 (20): 3933–3941. doi:10.1113/jphysiol.2010.195115. PMC 3000583. PMID 20807790.  edit
  15. ^ Shim, S. S.; Hammonds, M. D.; Tatsuoka, C.; Jung Feng, I. (2012). "Effects of 4-weeks of treatment with lithium and olanzapine on long-term potentiation in hippocampal area CA1". Neuroscience Letters 524 (1): 5–9. doi:10.1016/j.neulet.2012.06.047. PMID 22750162.  edit
  16. ^ Son, H.; Yu, I. T.; Hwang, S. J.; Kim, J. S.; Lee, S. H.; Lee, Y. S.; Kaang, B. K. (2003). "Lithium enhances long-term potentiation independently of hippocampal neurogenesis in the rat dentate gyrus". Journal of neurochemistry 85 (4): 872–881. doi:10.1046/j.1471-4159.2003.01725.x. PMID 12716419.  edit
  17. ^ Voytovych, H.; Kriváneková, L.; Ziemann, U. (2012). "Lithium: A switch from LTD- to LTP-like plasticity in human cortex". Neuropharmacology 63 (2): 274–279. doi:10.1016/j.neuropharm.2012.03.023. PMID 22507665.  edit
  18. ^ a b Hashimoto, R.; Fujimaki, K.; Jeong, M. R.; Christ, L.; Chuang, D. M. (2003). "Lithium-induced inhibition of Src tyrosine kinase in rat cerebral cortical neurons: A role in neuroprotection against N-methyl-D-aspartate receptor-mediated excitotoxicity". FEBS letters 538 (1–3): 145–148. doi:10.1016/S0014-5793(03)00167-4. PMID 12633868.  edit
  19. ^ Chen, R. W.; Chuang, D. M. (1999). "Long term lithium treatment suppresses p53 and Bax expression but increases Bcl-2 expression. A prominent role in neuroprotection against excitotoxicity". The Journal of biological chemistry 274 (10): 6039–6042. doi:10.1074/jbc.274.10.6039. PMID 10037682.  edit
  20. ^ Nonaka, S.; Hough, C. J.; Chuang, D. M. (1998). "Chronic lithium treatment robustly protects neurons in the central nervous system against excitotoxicity by inhibiting N-methyl-D-aspartate receptor-mediated calcium influx". Proceedings of the National Academy of Sciences of the United States of America 95 (5): 2642–2647. doi:10.1073/pnas.95.5.2642. PMC 19446. PMID 9482940.  edit
  21. ^ Hashimoto, R.; Hough, C.; Nakazawa, T.; Yamamoto, T.; Chuang, D. M. (2002). "Lithium protection against glutamate excitotoxicity in rat cerebral cortical neurons: Involvement of NMDA receptor inhibition possibly by decreasing NR2B tyrosine phosphorylation". Journal of neurochemistry 80 (4): 589–597. doi:10.1046/j.0022-3042.2001.00728.x. PMID 11841566.  edit
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