Ispronicline

Ispronicline
Clinical data
ATC code	none;
Identifiers
	show IUPAC name
CAS Number	252870-53-4 ;
PubChem CID	9824145;
ChemSpider	7999892 ;
UNII	3E05NBH9V5;
KEGG	D08935 ;
Chemical and physical data
Formula	C14H22N2O
Molar mass	234.336 g·mol−1
3D model (JSmol)	Interactive image;
	show SMILES
	show InChI
	(what is this?)

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]

It has also progressed to phase II as a potential treatment for ADHD. With dosages of 50mg day showing a significant improvement in ADHD symptoms^[2]^[3]

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.^[4]^[5]^[6]^[7]^[8] However, mid stage clinical trials failed to show sufficient efficacy to continue development as a pharmaceutical drug.^[1]

References[]

^ Jump up to: ^a ^b Targacept Drops Development of Alzheimer's Drug
^ Potter, Alexandra S.; Dunbar, Geoffrey; Mazzulla, Emily; Hosford, David; Newhouse, Paul A. (2014-02-01). "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. ISSN 1873-2402. PMID 23856296.
^ AstraZeneca (2009-10-29). "An Exploratory Trial of AZD3480 (TC-1734) for the Treatment of Adult Attention-Deficit/Hyperactivity Disorder (ADHD)". Targacept Inc. Cite journal requires |journal= (help)
^ 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): 147–66. doi:10.1111/j.1527-3458.2004.tb00010.x. PMC 6741718. PMID 15179444.
^ Dunbar G, Demazières A, Monreal A, Cisterni C, Metzger D, Kuchibhatla R, Luthringer R (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): 715–26. doi:10.1177/0091270006288730. PMID 16809797. S2CID 22499622.
^ 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.
^ Dunbar G, Boeijinga PH, Demazières A, Cisterni C, Kuchibhatla R, Wesnes K, Luthringer R (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): 919–29. doi:10.1007/s00213-006-0675-x. PMID 17225162. S2CID 10920515.
^ 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): 171–8. doi:10.1177/0269881107066855. PMID 17329297. S2CID 10056476.

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[failed-1] Jump up to: ^a ^b Targacept Drops Development of Alzheimer's Drug

[2] Potter, Alexandra S.; Dunbar, Geoffrey; Mazzulla, Emily; Hosford, David; Newhouse, Paul A. (2014-02-01). "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. ISSN 1873-2402. PMID 23856296.

[3] AstraZeneca (2009-10-29). "An Exploratory Trial of AZD3480 (TC-1734) for the Treatment of Adult Attention-Deficit/Hyperactivity Disorder (ADHD)". Targacept Inc. Cite journal requires |journal= (help)

[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): 147–66. 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, Luthringer R (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): 715–26. 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.

[7] Dunbar G, Boeijinga PH, Demazières A, Cisterni C, Kuchibhatla R, Wesnes K, Luthringer R (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): 919–29. 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): 171–8. doi:10.1177/0269881107066855. PMID 17329297. S2CID 10056476.

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ATC code: N06B

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Clinical data

ATC code	none
Identifiers
show IUPAC name (2S,4E)-5-(5-isopropoxypyridin-3-yl)-N-methylpent-4-en-2-amine
CAS Number	252870-53-4^Y
PubChem CID	9824145
ChemSpider	7999892^N
UNII	3E05NBH9V5
KEGG	D08935^Y
Chemical and physical data
Formula	C₁₄H₂₂N₂O
Molar mass	234.336 g·mol⁻¹
3D model (JSmol)	Interactive image
show SMILES C[C@@H](C/C=C/C1=CC(=CN=C1)OC(C)C)NC
show InChI 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
^NY (what is this?)

Ispronicline

See also[]

References[]