Ispronicline

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Ispronicline
Ispronicline.png
Systematic (IUPAC) name
(2S,4E)-5-(5-isopropoxypyridin-3-yl)-N-methylpent-4-en-2-amine
Identifiers
CAS Number 252870-53-4 YesY
ATC code none
PubChem CID: 9824145
ChemSpider 7999892 N
UNII 3E05NBH9V5 YesY
KEGG D08935 YesY
Chemical data
Formula C14H22N2O
Molecular mass 234.336
  • C[C@@H](C/C=C/C1=CC(=CN=C1)OC(C)C)NC
  • InChI=1S/C14H22N2O/c1-11(2)17-14-8-13(9-16-10-14)7-5-6-12(3)15-4/h5,7-12,15H,6H2,1-4H3/b7-5+/t12-/m0/s1 N
  • Key:RPCVIAXDAUMJJP-PZBABLGHSA-N N
 NYesY (what is this?)  (verify)

Ispronicline (TC-1734, AZD-3480) is an experimental drug which acts as a partial agonist at neural nicotinic acetylcholine receptors. It progressed to phase II clinical trials for the treatment of dementia and Alzheimer's disease, but is no longer under development.[1]

Ispronicline is subtype-selective, binding primarily to the α4β2 subtype. It has antidepressant, nootropic and neuroprotective effects.[medical citation needed]

Early stage clinical trials showed that ispronicline was well tolerated, with the main side effects being dizziness and headache.[2][3][4][5][6] However, mid stage clinical trials failed to show sufficient efficacy to continue development as a pharmaceutical drug.[1]

References

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  1. 1.0 1.1 Targacept Drops Development of Alzheimer's Drug
  2. Gatto GJ, Bohme GA, Caldwell WS, Letchworth SR, Traina VM, Obinu MC, Laville M, Reibaud M, Pradier L, Dunbar G, Bencherif M. TC-1734: an orally active neuronal nicotinic acetylcholine receptor modulator with antidepressant, neuroprotective and long-lasting cognitive effects. CNS Drug Reviews. 2004 Summer;10(2):147-66. PMID 15179444
  3. Dunbar G, Demazières A, Monreal A, Cisterni C, Metzger D, Kuchibhatla R, Luthringer R. Pharmacokinetics and safety profile of ispronicline (TC-1734), a new brain nicotinic receptor partial agonist, in young healthy male volunteers. Journal of Clinical Pharmacology. 2006 Jul;46(7):715-26. PMID 16809797
  4. Lippiello P, Letchworth SR, Gatto GJ, Traina VM, Bencherif M. Ispronicline: a novel alpha4beta2 nicotinic acetylcholine receptor-selective agonist with cognition-enhancing and neuroprotective properties. Journal of Molecular Neuroscience. 2006;30(1-2):19-20. PMID 17192610
  5. Dunbar G, Boeijinga PH, Demazières A, Cisterni C, Kuchibhatla R, Wesnes K, Luthringer R. Effects of TC-1734 (AZD3480), a selective neuronal nicotinic receptor agonist, on cognitive performance and the EEG of young healthy male volunteers. Psychopharmacology (Berlin). 2007 May;191(4):919-29. doi:10.1007/s00213-006-0675-x PMID 17225162
  6. Dunbar GC, Inglis F, Kuchibhatla R, Sharma T, Tomlinson M, Wamsley J. Effect of ispronicline, a neuronal nicotinic acetylcholine receptor partial agonist, in subjects with age associated memory impairment (AAMI). Journal of Psychopharmacology. 2007 Mar;21(2):171-8. PMID 17329297