Wikipedia

Itameline

Itameline (INNTooltip International Nonproprietary Name; developmental code name RU-47213) is a non-selective muscarinic acetylcholine receptor agonist which was under development for the treatment of Alzheimer's disease and memory disorders but was never marketed.[1][2][3] It has been referred to as a "nootropic" (cognitive enhancer).[4][5]

Itameline
Clinical data
Other namesRU-47213; RU47213
Drug classNon-selective muscarinic acetylcholine receptor agonist
Identifiers
  • (4-chlorophenyl) 5-[(E)-methoxyiminomethyl]-3,6-dihydro-2H-pyridine-1-carboxylate
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC14H15ClN2O3
Molar mass294.74 g·mol−1
3D model (JSmol)
  • CO/N=C/C1=CCCN(C1)C(=O)OC2=CC=C(C=C2)Cl
  • InChI=1S/C14H15ClN2O3/c1-19-16-9-11-3-2-8-17(10-11)14(18)20-13-6-4-12(15)5-7-13/h3-7,9H,2,8,10H2,1H3/b16-9
  • Key:CTVQNEVLCGSTKL-CXUHLZMHSA-N

The drug is a prodrug of RU-35963, an arecoline derivative.[6][7][2] It is an agonist of the muscarinic acetylcholine M1 receptor as well as of other muscarinic acetylcholine receptors.[8][6][9][7][2] Itameline is described as being superior to arecoline in terms of potency, central selectivity, and duration of action.[6][7] The drug shows antiamnesic effects in animals, for instance reversing scopolamine-induced memory deficits.[10][6][2][3] Structurally, it is a tetrahydropyridine similarly to xanomeline and milameline.[11]

Itameline was first described in the scientific literature by 1992.[3] It was under development by Hoechst Marion Roussel and reached phase 2 clinical trials by 1998 prior to the discontinuation of its development.[12][7][4]

References

edit
  1. ^ "Delving into the Latest Updates on Itameline with Synapse". Synapse. 28 September 2024. Retrieved 26 October 2024.
  2. ^ a b c d M'Harzi M, Willig F, Gieules C, Palou AM, Oberlander C, Barzaghi F (April 1997). "Ameliorating effects of RU 47213, a novel oral and long-lasting cholinomimetic agent, on working memory impairments in rats". Pharmacology, Biochemistry, and Behavior. 56 (4): 663–668. doi:10.1016/s0091-3057(96)00423-6. PMID 9130292.663-668&rft.date=1997-04&rft_id=info:doi/10.1016/s0091-3057(96)00423-6&rft_id=info:pmid/9130292&rft.aulast=M'Harzi&rft.aufirst=M&rft.au=Willig, F&rft.au=Gieules, C&rft.au=Palou, AM&rft.au=Oberlander, C&rft.au=Barzaghi, F&rfr_id=info:sid/en.wikipedia.org:Itameline" class="Z3988">
  3. ^ a b c Toja E, Bonetti C, Butti A, Hunt P, Fortin M, Barzaghi F, et al. (1992). "1-substituted-1,2,5,6-tetrahydropyridine-3-carboxaldehyde-O-alkyloximes as novel orally active and long-lasting muscarinic cholinergic agonists". European Journal of Medicinal Chemistry. 27 (5). Elsevier BV: 519–526. doi:10.1016/0223-5234(92)90186-5. ISSN 0223-5234.519-526&rft.date=1992&rft_id=info:doi/10.1016/0223-5234(92)90186-5&rft.issn=0223-5234&rft.aulast=Toja&rft.aufirst=E&rft.au=Bonetti, C&rft.au=Butti, A&rft.au=Hunt, P&rft.au=Fortin, M&rft.au=Barzaghi, F&rft.au=Formento, ML&rft.au=Maggioni, A&rft.au=Nencioni, A&rft.au=Galliani, G&rfr_id=info:sid/en.wikipedia.org:Itameline" class="Z3988">
  4. ^ a b Froestl W, Muhs A, Pfeifer A (2012). "Cognitive enhancers (nootropics). Part 1: drugs interacting with receptors". Journal of Alzheimer's Disease. 32 (4): 793–887. doi:10.3233/JAD-2012-121186. PMID 22886028.793-887&rft.date=2012&rft_id=info:doi/10.3233/JAD-2012-121186&rft_id=info:pmid/22886028&rft.aulast=Froestl&rft.aufirst=W&rft.au=Muhs, A&rft.au=Pfeifer, A&rfr_id=info:sid/en.wikipedia.org:Itameline" class="Z3988">
  5. ^ Fischer F, Matthisson M, Herrling P (2004). "List of drugs in development for neurodegenerative diseases". Neuro-Degenerative Diseases. 1 (1): 50–70. doi:10.1159/000077879. PMID 16908974.50-70&rft.date=2004&rft_id=info:doi/10.1159/000077879&rft_id=info:pmid/16908974&rft.aulast=Fischer&rft.aufirst=F&rft.au=Matthisson, M&rft.au=Herrling, P&rfr_id=info:sid/en.wikipedia.org:Itameline" class="Z3988">
  6. ^ a b c d Camps P, Muñoz-Torrero D (February 2002). "Cholinergic drugs in pharmacotherapy of Alzheimer's disease". Mini Reviews in Medicinal Chemistry. 2 (1): 11–25. doi:10.2174/1389557023406638. PMID 12369954.11-25&rft.date=2002-02&rft_id=info:doi/10.2174/1389557023406638&rft_id=info:pmid/12369954&rft.aulast=Camps&rft.aufirst=P&rft.au=Muñoz-Torrero, D&rfr_id=info:sid/en.wikipedia.org:Itameline" class="Z3988">
  7. ^ a b c d Saklani A, Kutty SK (February 2008). "Plant-derived compounds in clinical trials". Drug Discovery Today. 13 (3–4): 161–171. doi:10.1016/j.drudis.2007.10.010. PMID 18275914.3–4&rft.pages=161-171&rft.date=2008-02&rft_id=info:doi/10.1016/j.drudis.2007.10.010&rft_id=info:pmid/18275914&rft.aulast=Saklani&rft.aufirst=A&rft.au=Kutty, SK&rfr_id=info:sid/en.wikipedia.org:Itameline" class="Z3988">
  8. ^ Palma JA (February 2024). "Muscarinic control of cardiovascular function in humans: a review of current clinical evidence". Clinical Autonomic Research. 34 (1): 31–44. doi:10.1007/s10286-024-01016-5. PMC 10994193. PMID 38305989.31-44&rft.date=2024-02&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10994193#id-name=PMC&rft_id=info:pmid/38305989&rft_id=info:doi/10.1007/s10286-024-01016-5&rft.aulast=Palma&rft.aufirst=JA&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10994193&rfr_id=info:sid/en.wikipedia.org:Itameline" class="Z3988">
  9. ^ Korczyn AD (October 2000). "Muscarinic M(1) agonists in the treatment of Alzheimer's disease". Expert Opinion on Investigational Drugs. 9 (10): 2259–2267. doi:10.1517/13543784.9.10.2259. PMID 11060805.2259-2267&rft.date=2000-10&rft_id=info:doi/10.1517/13543784.9.10.2259&rft_id=info:pmid/11060805&rft.aulast=Korczyn&rft.aufirst=AD&rfr_id=info:sid/en.wikipedia.org:Itameline" class="Z3988">
  10. ^ Deiana S, Platt B, Riedel G (August 2011). "The cholinergic system and spatial learning". Behavioural Brain Research. 221 (2): 389–411. doi:10.1016/j.bbr.2010.11.036. PMID 21108971.389-411&rft.date=2011-08&rft_id=info:doi/10.1016/j.bbr.2010.11.036&rft_id=info:pmid/21108971&rft.aulast=Deiana&rft.aufirst=S&rft.au=Platt, B&rft.au=Riedel, G&rfr_id=info:sid/en.wikipedia.org:Itameline" class="Z3988">
  11. ^ Mirza NR, Peters D, Sparks RG (2003). "Xanomeline and the antipsychotic potential of muscarinic receptor subtype selective agonists". CNS Drug Reviews. 9 (2): 159–186. doi:10.1111/j.1527-3458.2003.tb00247.x. PMC 6741650. PMID 12847557.159-186&rft.date=2003&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6741650#id-name=PMC&rft_id=info:pmid/12847557&rft_id=info:doi/10.1111/j.1527-3458.2003.tb00247.x&rft.aulast=Mirza&rft.aufirst=NR&rft.au=Peters, D&rft.au=Sparks, RG&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6741650&rfr_id=info:sid/en.wikipedia.org:Itameline" class="Z3988">
  12. ^ Eglen RM, Hegde SS (1998). "Selective modulation of muscarinic receptor subtypes: therapeutic potential". Emerging Drugs. 3 (1). Informa Healthcare: 67–80. doi:10.1517/14728214.3.1.67. ISSN 1361-9195.67-80&rft.date=1998&rft_id=info:doi/10.1517/14728214.3.1.67&rft.issn=1361-9195&rft.aulast=Eglen&rft.aufirst=RM&rft.au=Hegde, SS&rfr_id=info:sid/en.wikipedia.org:Itameline" class="Z3988">
 

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