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Itameline

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Muscarinic agonist

Pharmaceutical compound
Itameline
Clinical data
Other namesRU-47213; RU47213
Drug classNon-selective muscarinic acetylcholine receptor agonist
Identifiers
IUPAC name
  • (4-chlorophenyl) 5--3,6-dihydro-2H-pyridine-1-carboxylate
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC14H15ClN2O3
Molar mass294.74 g·mol
3D model (JSmol)
SMILES
  • CO/N=C/C1=CCCN(C1)C(=O)OC2=CC=C(C=C2)Cl
InChI
  • 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

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. It has been referred to as a "nootropic" (cognitive enhancer).

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

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

References

  1. "Delving into the Latest Updates on Itameline with Synapse". Synapse. 28 September 2024. Retrieved 26 October 2024.
  2. ^ 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.
  3. ^ 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.
  4. ^ 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.
  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.
  6. ^ 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.
  7. ^ 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.
  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.
  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.
  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.
  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.
  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.
Muscarinic acetylcholine receptor modulators
mAChRsTooltip Muscarinic acetylcholine receptors
Agonists
Antagonists
Precursors
(and prodrugs)
See also
Receptor/signaling modulators
Nicotinic acetylcholine receptor modulators
Acetylcholine metabolism/transport modulators
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