Ispronicline

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Ispronicline
Clinical data
ATC code
  • none
Identifiers
  • (2S,4E)-5-(5-isopropoxypyridin-3-yl)-N-methylpent-4-en-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H22N2O
Molar mass234.343 g·mol−1
3D model (JSmol)
  • C(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
 ☒NcheckY (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.

It has also progressed to phase II as a potential treatment for ADHD. With dosages of 50 mg/day showing a significant improvement in ADHD symptoms

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. However, mid-stage clinical trials failed to show sufficient efficacy to continue development as a pharmaceutical drug.

See also

References

  1. ^ a b Armental M (14 July 2014). "Targacept Drops Development of Alzheimer's Drug". Wall Street Journal.
  2. ^ Potter AS, Dunbar G, Mazzulla E, Hosford D, Newhouse PA (February 2014). "AZD3480, a novel nicotinic receptor agonist, for the treatment of attention-deficit/hyperactivity disorder in adults". Biological Psychiatry. 75 (3): 207–214. doi:10.1016/j.biopsych.2013.06.002. PMID 23856296. S2CID 44717647.
  3. ^ AstraZeneca (2009-10-29). "An Exploratory Trial of AZD3480 (TC-1734) for the Treatment of Adult Attention-Deficit/Hyperactivity Disorder (ADHD)". Targacept Inc.
  4. ^ Gatto GJ, Bohme GA, Caldwell WS, Letchworth SR, Traina VM, Obinu MC, et al. (2004). "TC-1734: an orally active neuronal nicotinic acetylcholine receptor modulator with antidepressant, neuroprotective and long-lasting cognitive effects". CNS Drug Reviews. 10 (2): 147–166. doi:10.1111/j.1527-3458.2004.tb00010.x. PMC 6741718. PMID 15179444.
  5. ^ Dunbar G, Demazières A, Monreal A, Cisterni C, Metzger D, Kuchibhatla R, et al. (July 2006). "Pharmacokinetics and safety profile of ispronicline (TC-1734), a new brain nicotinic receptor partial agonist, in young healthy male volunteers". Journal of Clinical Pharmacology. 46 (7): 715–726. doi:10.1177/0091270006288730. PMID 16809797. S2CID 22499622.
  6. ^ Lippiello P, Letchworth SR, Gatto GJ, Traina VM, Bencherif M (2006). "Ispronicline: a novel alpha4beta2 nicotinic acetylcholine receptor-selective agonist with cognition-enhancing and neuroprotective properties". Journal of Molecular Neuroscience. 30 (1–2): 19–20. doi:10.1385/JMN:30:1:19. PMID 17192610. S2CID 195688187.
  7. ^ Dunbar G, Boeijinga PH, Demazières A, Cisterni C, Kuchibhatla R, Wesnes K, et al. (May 2007). "Effects of TC-1734 (AZD3480), a selective neuronal nicotinic receptor agonist, on cognitive performance and the EEG of young healthy male volunteers". Psychopharmacology. 191 (4): 919–929. doi:10.1007/s00213-006-0675-x. PMID 17225162. S2CID 10920515.
  8. ^ Dunbar GC, Inglis F, Kuchibhatla R, Sharma T, Tomlinson M, Wamsley J (March 2007). "Effect of ispronicline, a neuronal nicotinic acetylcholine receptor partial agonist, in subjects with age associated memory impairment (AAMI)". Journal of Psychopharmacology. 21 (2): 171–178. doi:10.1177/0269881107066855. PMID 17329297. S2CID 10056476.
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