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Chemical Compound Review

donepezil     2-[(1-benzyl-4- piperidyl)methyl]-5,6...

Synonyms: donepezilo, Donaz, Eranz, donepezilum, CHEMBL502, ...
 Kuhl,  Hallett,  Rigaud,  Bartenstein,  Silman,  Grundman,  Knechtelsdorfer,  Babiloni,  Mayerhofer,  Foster,  Soininen,  Phipps,  Aisen,  Clark,  Weisler, Martin Dichgans, Hugh S. Markus, Stephen Salloway, Auli Verkkoniemi, Margaret Moline, Qin Wang, Holly Posner, Hugues S. Chabriat,  Teipel,  Kryger,  Sussman,  Mori,  Mintzer,  Bennett,  Traykov,  Petersen,  Chisari,  Platania,  Frisoni,  Winblad,  Grundman,  Moulin,  Kazui,  Schultz,  Jin,  Rogers,  Flashman,  Wishart,  Matsumoto,  Padovani,  Tragl,  Borroni,  Huber,  Ferris,  Nakano,  Subbiah,  Möller,  Mersich,  Del Percio,  Latour,  Charles,  Cattabeni,  Ferri,  Harvey,  Small,  Thal,  Moretti,  Mintzer,  Hashimoto,  Salinari,  Jack,  Zhang,  Rossini,  Perdomo,  Waldemar,  Scheltens,  Drzezga,  Rabin,  Cassetta,  Frey,  Snyder,  Sano,  Dal Forno,  Schwaiger,  Petersen,  Thomas,  Ferreri,  Zanetti,  Kim,  Jack,  Engedal,  Mohs,  Ieni,  Marcello,  Colciaghi,  Obermayr,  Wetterholm,  Wimo,  Forette,  Grafman,  Koeppe,  Rodriguez,  Canonico,  Lanuzza,  Hampel,  Kilbourn,  Galasko,  Kaye,  Yu,  Thal,  Couderc,  Chiechio,  Vancheri,  Modrego,  Cahn-Weiner,  Pascual-Marqui,  Gauthier,  Jann,  Verhey,  Decarli,  Geyer,  Zamrini,  Sortino,  McHugh,  Copani,  Frasca,  Nobili,  van Dyck,  Luca Romani,  Zimmermann,  Doraiswamy,  Yasuda,  Shirley,  Jin,  Salazar,  Mamourian,  Di Luca,  Pharr,  Haglund,  Miniussi,  Minoshima,  Doody,  Krishnan,  Gardoni,  Litvan,  Santulli,  Saykin,  Schafer,  Mulnard,  
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Disease relevance of donepezil


Psychiatry related information on donepezil

  • Among 94 patients with probable Alzheimer's disease who we treated with donepezil, seven patients developed urinary incontinence, although this event was transient in most patients [1].
  • After stabilization on donepezil (5.7 +/- 1.7 weeks at 10 mg) patients showed increased frontal activity relative to unmedicated controls, which was positively correlated with improvement in task performance (r = 0.49, P = 0.05) as well as baseline hippocampal volume (r = 0.62, P < 0.05) [7].
  • Treating visual hallucinations with donepezil [8].
  • The benefit of donepezil over placebo was demonstrated by the Gottfries-Bråne-Steen (a global assessment for rating dementia symptoms) total score at weeks 24, 36, and 52 (p < 0.05) and at the study end point (week 52, last observation carried forward; p = 0.054) [9].
  • To our knowledge this is the first published report on the use of donepezil in the treatment of mood disorders [10].

High impact information on donepezil


Chemical compound and disease context of donepezil


Biological context of donepezil

  • Our results indicate that CPT-11 binds within the active site gorge of the protein in a fashion similar to that observed with the Alzheimer drug donepezil [19].
  • Although demonstrating differences in their temporal kinetics, both WAY 100635 and NAD-299 attenuated the impairment of PA caused by scopolamine (0.3 mg/kg s.c.). Donepezil did not block the PA deficit caused by the 0.3 mg/kg dose of scopolamine, but it prevented the inhibitory effects of the 0.2 mg/kg dose of scopolamine [14].
  • Consequently, these results do not support the hypothesis that the ApoE phenotype and gender are predictors of the response to donepezil in Alzheimer's disease patients [20].
  • Next, we examined the effects of donepezil on glutamate-induced apoptosis [21].
  • The effects of the acetylcholinesterase inhibitor donepezil on cell viability and proliferation events have been analysed in SH-SY5Y human neuroblastoma cells [22].

Anatomical context of donepezil


Associations of donepezil with other chemical compounds


Gene context of donepezil

  • Here, we investigate the mechanisms of action of the AChEI donepezil on APP (amyloid precursor protein) metabolism and on the activity/trafficking of the alpha-secretase candidate ADAM 10, in differentiated human neuroblastoma cells (SH-SY5Y) [33].
  • The anti-amnesic and neuroprotective effects of donepezil against amyloid beta(25-35) peptide-induced toxicity in mice involve an interaction with the sigma(1) receptor [34].
  • The present study provides evidence that donepezil influences APP metabolism in platelets, and suggests that ApoE genotype might be an important modulating factor for drug responsiveness in AD [35].
  • The present study was designed as a randomised controlled trial to evaluate long term effects of donepezil, a cerebral selective ChEI, on basal GH and IGF-1 levels and on GH response to GHRH (1 microg/kg i.v., GHRH test) before and after an 8-week donepezil treatment period [36].
  • Structure of acetylcholinesterase complexed with E2020 (Aricept): implications for the design of new anti-Alzheimer drugs [37].

Analytical, diagnostic and therapeutic context of donepezil


  1. Urinary incontinence: an unrecognised adverse effect with donepezil. Hashimoto, M., Imamura, T., Tanimukai, S., Kazui, H., Mori, E. Lancet (2000) [Pubmed]
  2. Donepezil for Down's syndrome. Kishnani, P.S., Spiridigliozzi, G.A., Heller, J.H., Sullivan, J.A., Doraiswamy, P.M., Krishnan, K.R. The American journal of psychiatry. (2001) [Pubmed]
  3. Does donepezil treatment slow the progression of hippocampal atrophy in patients with Alzheimer's disease? Hashimoto, M., Kazui, H., Matsumoto, K., Nakano, Y., Yasuda, M., Mori, E. The American journal of psychiatry. (2005) [Pubmed]
  4. Randomized placebo-controlled trial of donepezil in patients with progressive supranuclear palsy. Litvan, I., Phipps, M., Pharr, V.L., Hallett, M., Grafman, J., Salazar, A. Neurology (2001) [Pubmed]
  5. Treatment of tardive dyskinesia with donepezil. Caroff, S.N., Campbell, E.C., Havey, J.C., Sullivan, K.A., Katz, I.R., Mann, S.C. The Journal of clinical psychiatry. (2001) [Pubmed]
  6. Donepezil in patients with subcortical vascular cognitive impairment: a randomised double-blind trial in CADASIL. Dichgans, M., Markus, H.S., Salloway, S., Verkkoniemi, A., Moline, M., Wang, Q., Posner, H., Chabriat, H.S. Lancet. Neurol (2008) [Pubmed]
  7. Cholinergic enhancement of frontal lobe activity in mild cognitive impairment. Saykin, A.J., Wishart, H.A., Rabin, L.A., Flashman, L.A., McHugh, T.L., Mamourian, A.C., Santulli, R.B. Brain (2004) [Pubmed]
  8. Treating visual hallucinations with donepezil. Burke, W.J., Roccaforte, W.H., Wengel, S.P. The American journal of psychiatry. (1999) [Pubmed]
  9. A 1-year, randomized, placebo-controlled study of donepezil in patients with mild to moderate AD. Winblad, B., Engedal, K., Soininen, H., Verhey, F., Waldemar, G., Wimo, A., Wetterholm, A.L., Zhang, R., Haglund, A., Subbiah, P. Neurology (2001) [Pubmed]
  10. Donepezil in treatment-resistant bipolar disorder. Burt, T., Sachs, G.S., Demopulos, C. Biol. Psychiatry (1999) [Pubmed]
  11. Suppression of methamphetamine-seeking behavior by nicotinic agonists. Hiranita, T., Nawata, Y., Sakimura, K., Anggadiredja, K., Yamamoto, T. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  12. In vivo butyrylcholinesterase activity is not increased in Alzheimer's disease synapses. Kuhl, D.E., Koeppe, R.A., Snyder, S.E., Minoshima, S., Frey, K.A., Kilbourn, M.R. Ann. Neurol. (2006) [Pubmed]
  13. Limited donepezil inhibition of acetylcholinesterase measured with positron emission tomography in living Alzheimer cerebral cortex. Kuhl, D.E., Minoshima, S., Frey, K.A., Foster, N.L., Kilbourn, M.R., Koeppe, R.A. Ann. Neurol. (2000) [Pubmed]
  14. Selective 5-HT1A antagonists WAY 100635 and NAD-299 attenuate the impairment of passive avoidance caused by scopolamine in the rat. Misane, I., Ogren, S.O. Neuropsychopharmacology (2003) [Pubmed]
  15. Qualitative estimates of medial temporal atrophy as a predictor of progression from mild cognitive impairment to dementia. Decarli, C., Frisoni, G.B., Clark, C.M., Harvey, D., Grundman, M., Petersen, R.C., Thal, L.J., Jin, S., Jack, C.R., Scheltens, P. Arch. Neurol. (2007) [Pubmed]
  16. Combination of donepezil and gabapentin for behavioral disorders in Alzheimer's disease. Dallocchio, C., Buffa, C., Mazzarello, P. The Journal of clinical psychiatry. (2000) [Pubmed]
  17. Antiamnesic and neuroprotective effects of donepezil against learning impairments induced in mice by exposure to carbon monoxide gas. Meunier, J., Ieni, J., Maurice, T. J. Pharmacol. Exp. Ther. (2006) [Pubmed]
  18. Acetylcholinesterase inhibitors used in treatment of Alzheimer's disease prevent glutamate neurotoxicity via nicotinic acetylcholine receptors and phosphatidylinositol 3-kinase cascade. Takada-Takatori, Y., Kume, T., Sugimoto, M., Katsuki, H., Sugimoto, H., Akaike, A. Neuropharmacology (2006) [Pubmed]
  19. The crystal structure of the complex of the anticancer prodrug 7-ethyl-10-[4-(1-piperidino)-1-piperidino]-carbonyloxycamptothecin (CPT-11) with Torpedo californica acetylcholinesterase provides a molecular explanation for its cholinergic action. Harel, M., Hyatt, J.L., Brumshtein, B., Morton, C.L., Yoon, K.J., Wadkins, R.M., Silman, I., Sussman, J.L., Potter, P.M. Mol. Pharmacol. (2005) [Pubmed]
  20. Presence or absence of at least one epsilon 4 allele and gender are not predictive for the response to donepezil treatment in Alzheimer's disease. Rigaud, A.S., Traykov, L., Latour, F., Couderc, R., Moulin, F., Forette, F. Pharmacogenetics (2002) [Pubmed]
  21. Nicotinic acetylcholine receptor-mediated neuroprotection by donepezil against glutamate neurotoxicity in rat cortical neurons. Takada, Y., Yonezawa, A., Kume, T., Katsuki, H., Kaneko, S., Sugimoto, H., Akaike, A. J. Pharmacol. Exp. Ther. (2003) [Pubmed]
  22. Novel neuronal targets for the acetylcholinesterase inhibitor donepezil. Sortino, M.A., Frasca, G., Chisari, M., Platania, P., Chiechio, S., Vancheri, C., Copani, A., Canonico, P.L. Neuropharmacology (2004) [Pubmed]
  23. Dementia with Lewy bodies: response of delirium-like features to donepezil. Kaufer, D.I., Catt, K.E., Lopez, O.L., DeKosky, S.T. Neurology (1998) [Pubmed]
  24. Donepezil hydrochloride preserves regional cerebral blood flow in patients with Alzheimer's disease. Nakano, S., Asada, T., Matsuda, H., Uno, M., Takasaki, M. J. Nucl. Med. (2001) [Pubmed]
  25. Clinical pharmacokinetics and pharmacodynamics of cholinesterase inhibitors. Jann, M.W., Shirley, K.L., Small, G.W. Clinical pharmacokinetics. (2002) [Pubmed]
  26. Effects of donepezil on cortical metabolic response to activation during (18)FDG-PET in Alzheimer's disease: a double-blind cross-over trial. Teipel, S.J., Drzezga, A., Bartenstein, P., Möller, H.J., Schwaiger, M., Hampel, H. Psychopharmacology (Berl.) (2006) [Pubmed]
  27. Reversal of visual attention dysfunction after AMPA lesions of the nucleus basalis magnocellularis (NBM) by the cholinesterase inhibitor donepezil and by a 5-HT1A receptor antagonist WAY 100635. Balducci, C., Nurra, M., Pietropoli, A., Samanin, R., Carli, M. Psychopharmacology (Berl.) (2003) [Pubmed]
  28. Diagnosis, management, and treatment of Alzheimer disease: a guide for the internist. Richards, S.S., Hendrie, H.C. Arch. Intern. Med. (1999) [Pubmed]
  29. Donepezil improves cognition and global function in Alzheimer disease: a 15-week, double-blind, placebo-controlled study. Donepezil Study Group. Rogers, S.L., Doody, R.S., Mohs, R.C., Friedhoff, L.T. Arch. Intern. Med. (1998) [Pubmed]
  30. The effect of drugs for Alzheimer disease assessed by means of neuroradiological techniques. Modrego, P.J. Current medicinal chemistry (2006) [Pubmed]
  31. Effect of donepezil on brain acetylcholinesterase activity in patients with AD measured by PET. Shinotoh, H., Aotsuka, A., Fukushi, K., Nagatsuka, S., Tanaka, N., Ota, T., Tanada, S., Irie, T. Neurology (2001) [Pubmed]
  32. Mild cognitive impairment can be distinguished from Alzheimer disease and normal aging for clinical trials. Grundman, M., Petersen, R.C., Ferris, S.H., Thomas, R.G., Aisen, P.S., Bennett, D.A., Foster, N.L., Jack, C.R., Galasko, D.R., Doody, R., Kaye, J., Sano, M., Mohs, R., Gauthier, S., Kim, H.T., Jin, S., Schultz, A.N., Schafer, K., Mulnard, R., van Dyck, C.H., Mintzer, J., Zamrini, E.Y., Cahn-Weiner, D., Thal, L.J. Arch. Neurol. (2004) [Pubmed]
  33. Acetylcholinesterase inhibitors increase ADAM10 activity by promoting its trafficking in neuroblastoma cell lines. Zimmermann, M., Gardoni, F., Marcello, E., Colciaghi, F., Borroni, B., Padovani, A., Cattabeni, F., Di Luca, M. J. Neurochem. (2004) [Pubmed]
  34. The anti-amnesic and neuroprotective effects of donepezil against amyloid beta(25-35) peptide-induced toxicity in mice involve an interaction with the sigma(1) receptor. Meunier, J., Ieni, J., Maurice, T. Br. J. Pharmacol. (2006) [Pubmed]
  35. ApoE genotype influences the biological effect of donepezil on APP metabolism in Alzheimer disease: evidence from a peripheral model. Borroni, B., Colciaghi, F., Pastorino, L., Archetti, S., Corsini, P., Cattabeni, F., Di Luca, M., Padovani, A. European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology. (2002) [Pubmed]
  36. The age-related down-regulation of the growth hormone/insulin-like growth factor-1 axis in the elderly male is reversed considerably by donepezil, a drug for Alzheimer's disease. Obermayr, R.P., Mayerhofer, L., Knechtelsdorfer, M., Mersich, N., Huber, E.R., Geyer, G., Tragl, K.H. Exp. Gerontol. (2005) [Pubmed]
  37. Structure of acetylcholinesterase complexed with E2020 (Aricept): implications for the design of new anti-Alzheimer drugs. Kryger, G., Silman, I., Sussman, J.L. Structure (1999) [Pubmed]
  38. Donepezil effects on sources of cortical rhythms in mild Alzheimer's disease: Responders vs. Non-Responders. Babiloni, C., Cassetta, E., Dal Forno, G., Del Percio, C., Ferreri, F., Ferri, R., Lanuzza, B., Miniussi, C., Moretti, D.V., Nobili, F., Pascual-Marqui, R.D., Rodriguez, G., Luca Romani, G., Salinari, S., Zanetti, O., Rossini, P.M. Neuroimage (2006) [Pubmed]
  39. Randomized, placebo-controlled trial of the effects of donepezil on neuronal markers and hippocampal volumes in Alzheimer's disease. Krishnan, K.R., Charles, H.C., Doraiswamy, P.M., Mintzer, J., Weisler, R., Yu, X., Perdomo, C., Ieni, J.R., Rogers, S. The American journal of psychiatry. (2003) [Pubmed]
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