Aricept~Donepezil~E2020

Treatment of Alzheimer Disease, trademark is Aricept || Reversible inhibitor of AChE but not of BChE

General

Type : Derivative of Donepezil, Piperidine, Drug, Inden

Chemical_Nomenclature : 2-[(1-benzylpiperidin-4-yl)methyl]-5,6-dimethoxy-2,3-dihydroinden-1-one\;hydrochloride

Canonical SMILES : COC1=C(C=C2C(=C1)CC(C2=O)CC3CCN(CC3)CC4=CC=CC=C4)OC.Cl

InChI : InChI=1S\/C24H29NO3.ClH\/c1-27-22-14-19-13-20(24(26)21(19)15-23(22)28-2)12-17-8-10-25(11-9-17)16-18-6-4-3-5-7-18\;\/h3-7,14-15,17,20H,8-13,16H2,1-2H3\;1H

InChIKey : XWAIAVWHZJNZQQ-UHFFFAOYSA-N

Other name(s) : Donepezil hydrochloride  ||  DPZ  ||  Donepezilo  ||  Donepezilum  ||  1-benzyl-4-[(5,6-dimethoxy-1-indanon-2-yl)methyl]piperidine  ||  (+\/-)-2,3-dihydro-5,6-dimethoxy-2-[[1-(phenylmethyl)-4-piperidinyl]methyl]-1H-inden-1-one  ||  Donepezil  ||  E2020  ||  Aricept


MW : 415.953

Formula : C24H30ClNO3

CAS_number : 120011-70-3,    120014-06-4

PubChem : 5741,    3152

UniChem : XWAIAVWHZJNZQQ-UHFFFAOYSA-N

IUPHAR : 6599

Wikipedia : Donepezil

Target

Families : Aricept~Donepezil~E2020 ligand of proteins in family
ACHE

Structure :
1EVE 7E3H 6O4W 4EY7

Protein :
torca-ACHE human-ACHE

References (57)

Title : The donepezil transdermal system for the treatment of patients with mild, moderate, or severe Alzheimer's disease: a critical review - Buck_2024_Expert.Rev.Neurother_24_607
Author(s) : Buck A , Rezaei K , Quazi A , Goldmeier G , Silverglate B , Grossberg GT
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Abstract :
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Title : Donepezil inhibits neuromuscular junctional acetylcholinesterase and enhances synaptic transmission and function in isolated skeletal muscle - Redman_2022_Br.J.Pharmacol__
Author(s) : Redman RR , Mackenzie H , Dissanayake KN , Eddleston M , Ribchester RR
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Title : Clinical efficacy and safety of donepezil in the treatment of Alzheimer's disease in Chinese patients - Zhang_2018_Clin.Interv.Aging_13_1963
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Title : Efficacy and Safety of Sustained Release Donepezil High Dose versus Immediate Release Donepezil Standard Dose in Japanese Patients with Severe Alzheimer's Disease: A Randomized, Double-Blind Trial - Homma_2016_J.Alzheimers.Dis_52_345
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Title : Structures of human acetylcholinesterase in complex with pharmacologically important ligands - Cheung_2012_J.Med.Chem_55_10282
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Gene_locus related to this paper: human-ACHE

Title : beta-Amyloid aggregation induced by human acetylcholinesterase: inhibition studies - Bartolini_2003_Biochem.Pharmacol_65_407
Author(s) : Bartolini M , Bertucci C , Cavrini V , Andrisano V
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PubMedSearch : Bartolini_2003_Biochem.Pharmacol_65_407
PubMedID: 12527333

Title : Use of donepezil in elderly patients with Alzheimer's disease--a Hawaii based study - Alagiakrishnan_2000_Hawaii.Med.J_59_57
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PubMedID: 10800254

Title : Huprine X is a Novel High-Affinity Inhibitor of Acetylcholinesterase That Is of Interest for Treatment of Alzheimer's Disease - Camps_2000_Mol.Pharmacol_57_409
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Title : [Pharmacological properties of donepezil hydrochloride (Aricept), a drug for Alzheimer's disease] - Ogura_2000_Nihon.Yakurigaku.Zasshi_115_45
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PubMedSearch : Ogura_2000_Nihon.Yakurigaku.Zasshi_115_45
PubMedID: 10876815

Title : Inhibitory effect of orally administered donepezil hydrochloride (E2020), a novel treatment for Alzheimer's disease, on cholinesterase activity in rats - Kosasa_2000_Eur.J.Pharmacol_389_173
Author(s) : Kosasa T , Kuriya Y , Matsui K , Yamanishi Y
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PubMedID: 10688981

Title : Effects of donepezil on emotional\/behavioral symptoms in Alzheimer's disease patients - Weiner_2000_J.Clin.Psychiatry_61_487
Author(s) : Weiner MF , Martin-Cook K , Foster BM , Saine K , Fontaine CS , Svetlik DA
Ref : J Clin Psychiatry , 61 :487 , 2000
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PubMedSearch : Weiner_2000_J.Clin.Psychiatry_61_487
PubMedID: 10937606

Title : Donepezil Hydrochloride (E2020) and Other Acetylcholinesterase Inhibitors - Sugimoto_2000_Curr.Med.Chem_7_303
Author(s) : Sugimoto H , Iimura Y , Kawakami Y , Yamanishi Y
Ref : Curr Med Chem , 7 :303 , 2000
Abstract :
PubMedSearch : Sugimoto_2000_Curr.Med.Chem_7_303
PubMedID: 10637367

Title : Donepezil, a centrally acting acetylcholinesterase inhibitor, alleviates learning deficits in hypocholinergic models in rats - Ogura_2000_Methods.Find.Exp.Clin.Pharmacol_22_89
Author(s) : Ogura H , Kosasa T , Kuriya Y , Yamanishi Y
Ref : Methods Find Exp Clin Pharmacol , 22 :89 , 2000
Abstract :
PubMedSearch : Ogura_2000_Methods.Find.Exp.Clin.Pharmacol_22_89
PubMedID: 10849891

Title : Comparison of inhibitory activities of donepezil and other cholinesterase inhibitors on acetylcholinesterase and butyrylcholinesterase in vitro - Ogura_2000_Methods.Find.Exp.Clin.Pharmacol_22_609
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Abstract :
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PubMedID: 11256231

Title : The relationship between donepezil and behavioral disturbances in patients with Alzheimer's disease - Cummings_2000_Am.J.Geriatr.Psychiatry_8_134
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Ref : American Journal of Geriatry & Psychiatry , 8 :134 , 2000
Abstract :
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PubMedID: 10804074

Title : Rivastigmine, a new-generation cholinesterase inhibitor for the treatment of Alzheimer's disease - Jann_2000_Pharmacotherapy_20_1
Author(s) : Jann MW
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PubMedID: 10641971

Title : Molecular modelling and QSAR of reversible acetylcholines-terase inhibitors - Kaur_2000_Curr.Med.Chem_7_273
Author(s) : Kaur J , Zhang MQ
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Title : Structure of acetylcholinesterase complexed with E2020 (Aricept): implications for the design of new anti-Alzheimer drugs - Kryger_1999_Structure_7_297
Author(s) : Kryger G , Silman I , Sussman JL
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Abstract :
PubMedSearch : Kryger_1999_Structure_7_297
PubMedID: 10368299
Gene_locus related to this paper: torca-ACHE

Title : Huperzine-A in capsules and tablets for treating patients with Alzheimer disease - Xu_1999_Zhongguo.Yao.Li.Xue.Bao_20_486
Author(s) : Xu SS , Cai ZY , Qu ZW , Yang RM , Cai YL , Wang GQ , Su XQ , Zhong XS , Cheng RY , Xu WA , Li JX , Feng B
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PubMedID: 10678137

Title : [Treatment of Alzheimer's disease: acetylcholinesterase inhibitors]. - Lopez-Pousa_1999_Neurologia_14_180
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Ref : Neurologia , 14 :180 , 1999
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PubMedID: 10363493

Title : Clinical profile of donepezil in the treatment of Alzheimer's disease - Doody_1999_Gerontology_45_23
Author(s) : Doody RS
Ref : Gerontology , 45 :23 , 1999
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PubMedSearch : Doody_1999_Gerontology_45_23
PubMedID: 9876215

Title : Three-dimensional structure of a complex of E2020 with acetylcholinesterase from Torpedo californica - Kryger_1998_J.Physiol.Paris_92_191
Author(s) : Kryger G , Silman I , Sussman JL
Ref : Journal de Physiologie Paris , 92 :191 , 1998
Abstract :
PubMedSearch : Kryger_1998_J.Physiol.Paris_92_191
PubMedID: 9789806

Title : Donepezil improves cognition and global function in Alzheimer disease: a 15-week, double-blind, placebo-controlled study. Donepezil Study Group - Rogers_1998_Arch.Intern.Med_158_1021
Author(s) : Rogers SL , Doody RS , Mohs RC , Friedhoff LT
Ref : Archives of Internal Medicine , 158 :1021 , 1998
Abstract :
PubMedSearch : Rogers_1998_Arch.Intern.Med_158_1021
PubMedID: 9588436

Title : Aricept-induced nightmares in Alzheimer's disease: 2 case reports [letter] -
Author(s) : Ross JS , Shua-Haim JR
Ref : J Am Geriatr Soc , 46 :119 , 1998
PubMedID: 9434681

Title : A 24-week, double-blind, placebo-controlled trial of donepezil in patients with Alzheimer's disease. Donepezil Study Group - Rogers_1998_Neurology_50_136
Author(s) : Rogers SL , Farlow MR , Doody RS , Mohs R , Friedhoff LT
Ref : Neurology , 50 :136 , 1998
Abstract :
PubMedSearch : Rogers_1998_Neurology_50_136
PubMedID: 9443470

Title : Invited review: Cholinesterase inhibitors for Alzheimer's disease therapy: from tacrine to future applications - Giacobini_1998_Neurochem.Int_32_413
Author(s) : Giacobini E
Ref : Neurochem Int , 32 :413 , 1998
Abstract :
PubMedSearch : Giacobini_1998_Neurochem.Int_32_413
PubMedID: 9676739

Title : Long-term efficacy and safety of donepezil in the treatment of Alzheimer's disease: an interim analysis of the results of a US multicentre open label extension study - Rogers_1998_Eur.Neuropsychopharmacol_8_67
Author(s) : Rogers SL , Friedhoff LT
Ref : European Neuropsychopharmacology , 8 :67 , 1998
Abstract :
PubMedSearch : Rogers_1998_Eur.Neuropsychopharmacol_8_67
PubMedID: 9452942

Title : Donepezil use in Alzheimer disease - Barner_1998_Ann.Pharmacother_32_70
Author(s) : Barner EL , Gray SL
Ref : Annals of Pharmacotherapy , 32 :70 , 1998
Abstract :
PubMedSearch : Barner_1998_Ann.Pharmacother_32_70
PubMedID: 9475825

Title : Donepezil medicated memory improvement in traumatic brain injury during post acute rehabilitation - Taverni_1998_Brain.Inj_12_77
Author(s) : Taverni JP , Seliger G , Lichtman SW
Ref : Brain Injury , 12 :77 , 1998
Abstract :
PubMedSearch : Taverni_1998_Brain.Inj_12_77
PubMedID: 9483340

Title : Drug and Therapeutics Bulletin defends its stance over donepezil [letter] -
Author(s) : Collier J
Ref : British Medical Journal , 316 :1092 , 1998
PubMedID: 9558999

Title : How to cope with Alzheimer's disease? - Hasegawa_1998_Neurobiol.Aging_19_S107
Author(s) : Hasegawa K
Ref : Neurobiology of Aging , 19 :S107 , 1998
Abstract :
PubMedSearch : Hasegawa_1998_Neurobiol.Aging_19_S107
PubMedID: 9562478

Title : Comparative studies of huperzine A, E2020, and tacrine on behavior and cholinesterase activities - Cheng_1998_Pharmacol.Biochem.Behav_60_377
Author(s) : Cheng DH , Tang XC
Ref : Pharmacol Biochem Behav , 60 :377 , 1998
Abstract :
PubMedSearch : Cheng_1998_Pharmacol.Biochem.Behav_60_377
PubMedID: 9632220

Title : Tacrine and donepezil attenuate the neurotoxic effect of A beta(25-35) in rat PC12 cells - Svensson_1998_Neuroreport_9_1519
Author(s) : Svensson AL , Nordberg A
Ref : Neuroreport , 9 :1519 , 1998
Abstract :
PubMedSearch : Svensson_1998_Neuroreport_9_1519
PubMedID: 9631459

Title : Inhibition of cholinesterase-associated aryl acylamidase activity by anticholinesterase agents: focus on drugs potentially effective in Alzheimer's disease - Costagli_1998_Biochem.Pharmacol_55_1733
Author(s) : Costagli C , Galli A
Ref : Biochemical Pharmacology , 55 :1733 , 1998
Abstract :
PubMedSearch : Costagli_1998_Biochem.Pharmacol_55_1733
PubMedID: 9634011

Title : Reversal of scopolamine-induced deficits in radial maze performance by (-)-huperzine A: comparison with E2020 and tacrine - Wang_1998_Eur.J.Pharmacol_349_137
Author(s) : Wang T , Tang XC
Ref : European Journal of Pharmacology , 349 :137 , 1998
Abstract :
PubMedSearch : Wang_1998_Eur.J.Pharmacol_349_137
PubMedID: 9671090

Title : Donepezil (Aricept) therapy for Alzheimer's disease -
Author(s) : Geldmacher DS
Ref : Compr Ther , 23 :492 , 1997
PubMedID: 9262925

Title : Advertisements for donepezil (Aricept) in the BMJ. Advertisement suggests an unrealistic improvement in mental status -
Author(s) : Gray S
Ref : BMJ , 314 :1555 , 1997
PubMedID: 9183222

Title : Advertisements for donepezil (Aricept) in the BMJ. Local committee has declined to approve NHS hospital prescription of donepezil -
Author(s) : Wagner N
Ref : BMJ , 314 :1555 , 1997
PubMedID: 9183223

Title : Enhancing cognition in the intellectually intact - Whitehouse_1997_Hastings.Cent.Rep_27_14
Author(s) : Whitehouse PJ , Juengst E , Mehlman M , Murray TH
Ref : Hastings Center Report , 27 :14 , 1997
Abstract :
PubMedSearch : Whitehouse_1997_Hastings.Cent.Rep_27_14
PubMedID: 9219019

Title : Alzheimer's disease: an overview for the pharmacist - McGuffey_1997_J.Am.Pharm.Assoc_3_347
Author(s) : McGuffey EC
Ref : J Am Pharm Assoc , 3 :347 , 1997
Abstract :
PubMedSearch : McGuffey_1997_J.Am.Pharm.Assoc_3_347
PubMedID: 9170813

Title : Donepezil - Bryson_1997_Drugs.Aging_10_234
Author(s) : Bryson HM , Benfield P
Ref : Drugs & Aging , 10 :234 , 1997
Abstract :
PubMedSearch : Bryson_1997_Drugs.Aging_10_234
PubMedID: 9108896

Title : Absence of central cholinergic deficits in ApoE knockout mice - Anderson_1997_Psychopharmacology.(Berl)_132_135
Author(s) : Anderson R , Higgins GA
Ref : Psychopharmacology (Berl) , 132 :135 , 1997
Abstract :
PubMedSearch : Anderson_1997_Psychopharmacology.(Berl)_132_135
PubMedID: 9266610

Title : Enhanced performance of spatial and visual recognition memory tasks by the selective acetylcholinesterase inhibitor E2020 in rhesus monkeys - Rupniak_1997_Psychopharmacology_131_406
Author(s) : Rupniak NM , Tye SJ , Field MJ
Ref : Psychopharmacology , 131 :406 , 1997
Abstract :
PubMedSearch : Rupniak_1997_Psychopharmacology_131_406
PubMedID: 9226744

Title : Effects of NIK-247 on cholinesterase and scopolamine-induced amnesia [published erratum appears in Methods Find Exp Clin Pharmacol 1997 Jun\;19(5):364] - Kojima_1997_Methods.Find.Exp.Clin.Pharmacol_19_245
Author(s) : Kojima J , Nakajima K , Ochiai M , Nakayama K
Ref : Methods Find Exp Clin Pharmacol , 19 :245 , 1997
Abstract :
PubMedSearch : Kojima_1997_Methods.Find.Exp.Clin.Pharmacol_19_245
PubMedID: 9228650

Title : Functional activation of cerebral blood flow abolished by scopolamine is reversed by cognitive enhancers associated with cholinesterase inhibition: a positron emission tomography study in unanesthetized monkeys - Tsukada_1997_J.Pharmacol.Exp.Ther_281_1408
Author(s) : Tsukada H , Kakiuchi T , Ando I , Ouchi Y
Ref : Journal of Pharmacology & Experimental Therapeutics , 281 :1408 , 1997
Abstract :
PubMedSearch : Tsukada_1997_J.Pharmacol.Exp.Ther_281_1408
PubMedID: 9190877

Title : Advertisements for donepezil. National policy needs to be set for prescribing of this drug -
Author(s) : Boothby H , Zaidi SM , Seth V , Khalaf S , Jameel H , Mahomed S , al Y
Ref : BMJ , 315 :1624 , 1997
PubMedID: 9437305

Title : Advertisements for donepezil. Prices charged for private prescriptions for donepezil show huge variation -
Author(s) : Jones RW , Mann JB , Saunders SA
Ref : BMJ , 315 :1624 , 1997
PubMedID: 9437306

Title : Advertisements for donepezil. Review of drug in Drug and Therapeutics Bulletin is uninformed -
Author(s) : Wilkinson D
Ref : BMJ , 315 :1625 , 1997
PubMedID: 9437307

Title : The efficacy and safety of donepezil in patients with Alzheimer's disease: results of a US Multicentre, Randomized, Double-Blind, Placebo- Controlled Trial. The Donepezil Study Group - Rogers_1996_Dementia_7_293
Author(s) : Rogers SL , Friedhoff LT
Ref : Dementia , 7 :293 , 1996
Abstract :
PubMedSearch : Rogers_1996_Dementia_7_293
PubMedID: 8915035

Title : Huperzine A, a novel promising acetylcholinesterase inhibitor - Cheng_1996_Neuroreport_8_97
Author(s) : Cheng DH , Ren H , Tang XC
Ref : Neuroreport , 8 :97 , 1996
Abstract :
PubMedSearch : Cheng_1996_Neuroreport_8_97
PubMedID: 9051760

Title : The simulated binding of (+\/-)-2,3-dihydro-5,6-dimethoxy-2-[[1-(phenylmethyl)-4-piperidinyl]m eth yl] -1H-inden-1-one hydrochloride (E2020) and related inhibitors to free and acylated acetylcholinesterases and corresponding structure-activity analyses - Inoue_1996_J.Med.Chem_39_4460
Author(s) : Inoue A , Kawai T , Wakita M , Iimura Y , Sugimoto H , Kawakami Y
Ref : Journal of Medicinal Chemistry , 39 :4460 , 1996
Abstract :
PubMedSearch : Inoue_1996_J.Med.Chem_39_4460
PubMedID: 8893840

Title : Synthesis and structure-activity relationships of acetylcholinesterase inhibitors: 1-benzyl-4-[(5,6-dimethoxy-1-oxoindan-2- yl)methyl]piperidine hydrochloride and related compounds - Sugimoto_1995_J.Med.Chem_38_4821
Author(s) : Sugimoto H , Iimura Y , Yamanishi Y , Yamatsu K
Ref : Journal of Medicinal Chemistry , 38 :4821 , 1995
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PubMedSearch : Sugimoto_1995_J.Med.Chem_38_4821
PubMedID: 7490731

Title : Kinetic study on the inhibition of acetylcholinesterase by 1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-yl]methylpiperidine hydrochloride (E2020) - Nochi_1995_Biol.Pharm.Bull_18_1145
Author(s) : Nochi S , Asakawa N , Sato T
Ref : Biol Pharm Bull , 18 :1145 , 1995
Abstract :
PubMedSearch : Nochi_1995_Biol.Pharm.Bull_18_1145
PubMedID: 8535413

Title : Direct determination of E2020 enantiomers in plasma by liquid chromatography-mass spectrometry and column-switching techniques - Matsui_1995_J.Chromatogr.A_694_209
Author(s) : Matsui K , Oda Y , Ohe H , Tanaka S , Asakawa N
Ref : Journal of Chromatography A , 694 :209 , 1995
Abstract :
PubMedSearch : Matsui_1995_J.Chromatogr.A_694_209
PubMedID: 7719466

Title : Prediction of the binding site of 1-benzyl-4-[(5,6-dimethoxy-1-indanon-2-yl)methyl]piperidine in acetylcholinesterase by docking studies with the SYSDOC program - Pang_1994_J.Comput.Aided.Mol.Des_8_683
Author(s) : Pang YP , Kozikowski AP
Ref : J Comput Aided Mol Des , 8 :683 , 1994
Abstract :
PubMedSearch : Pang_1994_J.Comput.Aided.Mol.Des_8_683
PubMedID: 7738604

Title : Acetylcholinesterase protection and the anti-diisopropylfluorophosphate efficacy of E2020 - Galli_1994_Eur.J.Pharmacol_270_189
Author(s) : Galli A , Mori F , Benini L , Cacciarelli N
Ref : European Journal of Pharmacology , 270 :189 , 1994
Abstract :
PubMedSearch : Galli_1994_Eur.J.Pharmacol_270_189
PubMedID: 8039548

Title : The effects of novel cholinesterase inhibitors and selective muscarinic receptor agonists in tests of reference and working memory - Dawson_1993_Behav.Brain.Res_57_143
Author(s) : Dawson GR , Iversen SD
Ref : Behavioural Brain Research , 57 :143 , 1993
Abstract :
PubMedSearch : Dawson_1993_Behav.Brain.Res_57_143
PubMedID: 8117420