DONEPEZIL OXALATE

Details

Stereochemistry	RACEMIC
Molecular Formula	C24H29NO3.C2H2O4
Molecular Weight	469.5268
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)C(O)=O.COC1=C(OC)C=C2C(=O)C(CC3CCN(CC4=CC=CC=C4)CC3)CC2=C1

InChI

InChIKey=ZXVUKAUIAFEUEX-UHFFFAOYSA-N

InChI=1S/C24H29NO3.C2H2O4/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;3-1(4)2(5)6/h3-7,14-15,17,20H,8-13,16H2,1-2H3;(H,3,4)(H,5,6)

HIDE SMILES / InChI

Molecular Formula	C2H2O4
Molecular Weight	90.0349
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C24H29NO3
Molecular Weight	379.492
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020690s035,021720s008,022568s005lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/9428950

Donepezil, marketed under the trade name Aricept, is a medication used in the palliative treatment of Alzheimer's disease. Aricept is indicated for the treatment of dementia of the Alzheimer’s type. Efficacy has been demonstrated in patients with mild to moderate Alzheimer’s Disease, as well as in patients with severe Alzheimer’s Disease. Donepezil is postulated to exert its therapeutic effect by enhancing cholinergic function. This is accomplished by increasing the concentration of acetylcholine through reversible inhibition of its hydrolysis by acetylcholinesterase. Donepezil has been tested in other cognitive disorders including Lewy body dementia and Vascular dementia, but it is not currently approved for these indications. Donepezil has also been studied in patients with Mild Cognitive Impairment, schizophrenia, attention deficit disorder, post-coronary bypass cognitive impairment, cognitive impairment associated with multiple sclerosis, and Down syndrome.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Acetylcholinesterase 209 Target ID: CHEMBL220 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020690s035,021720s008,022568s005lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/11256231 \| https://www.ncbi.nlm.nih.gov/pubmed/16570913	Inhibitor 8504		6.7 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Alzheimer’s disease 278 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020690s035,021720s008,022568s005lbl.pdf	Palliative		Approved 8583	ARICEPT Approved Use Donepezil hydrochloride orally disintegrating tablets, USP are an acetylcholinesterase inhibitor indicated for the treatment of dementia of the Alzheimer's type. Efficacy has been demonstrated in patients with mild, moderate, and severe Alzheimer's Disease (1). Donepezil hydrochloride orally disintegrating tablets, USP are indicated for the treatment of dementia of the Alzheimer's type. Efficacy has been demonstrated in patients with mild, moderate, and severe Alzheimer's disease. Launch Date 1996

C_max

Value	Dose	Co-administered	Analyte	Population
34.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9839760	5 mg 1 times / day steady-state, oral dose: 5 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		DONEPEZIL blood	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
60.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9839760	10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		DONEPEZIL blood	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
2889.3 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9839760	5 mg 1 times / day steady-state, oral dose: 5 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		DONEPEZIL blood	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
5051.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9839760	10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		DONEPEZIL blood	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
72.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9839760	5 mg 1 times / day steady-state, oral dose: 5 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		DONEPEZIL blood	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
73.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9839760	10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		DONEPEZIL blood	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
4.4% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9839760	5 mg 1 times / day steady-state, oral dose: 5 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		DONEPEZIL blood	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
4.4% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9839760	10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		DONEPEZIL blood	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Doses

Dose	Population	Adverse events
175 mg single, transdermal Dose: 175 mg Route: transdermal Route: single Dose: 175 mg Sources: https://pubmed.ncbi.nlm.nih.gov/32440098	healthy, 24.9±3.3 years Health Status: healthy Age Group: 24.9±3.3 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/32440098	Sources: https://pubmed.ncbi.nlm.nih.gov/32440098
175 mg 1 times / 3 days steady, transdermal Dose: 175 mg, 1 times / 3 days Route: transdermal Route: steady Dose: 175 mg, 1 times / 3 days Sources: https://pubmed.ncbi.nlm.nih.gov/32440098	healthy, 24.9±3.3 years Health Status: healthy Age Group: 24.9±3.3 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/32440098	Sources: https://pubmed.ncbi.nlm.nih.gov/32440098
23 mg 1 times / day steady, oral Dose: 23 mg, 1 times / day Route: oral Route: steady Dose: 23 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022568Orig1s000MedR.pdf	unhealthy, 73.9 years Health Status: unhealthy Age Group: 73.9 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022568Orig1s000MedR.pdf	Disc. AE: Bradycardia, Diarrhea... AEs leading to discontinuation/dose reduction: Bradycardia (0.7%) Diarrhea (1.7%) Nausea (1.9%) Vomiting (2.9%) QT interval prolonged (0.4%) Anorexia (0.3%) Dizziness (1.1%) Headache (0.4%) Somnolence (0.6%) Syncope (0.2%) Aggression (0.5%) Agitation (0.8%) Confusional state (0.7%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/022568Orig1s000MedR.pdf
50 mg single, oral Overdose Dose: 50 mg Route: oral Route: single Dose: 50 mg Sources: https://pubmed.ncbi.nlm.nih.gov/10466911	unhealthy, 79 years Health Status: unhealthy Age Group: 79 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/10466911	Other AEs: Nausea, Vomiting... Other AEs: Nausea (1 patient) Vomiting (1 patient) Bradycardia (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/10466911
30 mg 1 times / day steady, oral Dose: 30 mg, 1 times / day Route: oral Route: steady Dose: 30 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/25202036	unhealthy, 80 years Health Status: unhealthy Age Group: 80 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/25202036	Disc. AE: Myoclonus... AEs leading to discontinuation/dose reduction: Myoclonus (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/25202036
10 mg 1 times / day steady, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: steady Dose: 10 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21719lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21719lbl.pdf	Other AEs: Diarrhea, Nausea... Other AEs: Diarrhea (3%) Nausea (3%) Vomiting (2%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21719lbl.pdf
5 mg 1 times / day steady, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: steady Dose: 5 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21719lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21719lbl.pdf	Disc. AE: Diarrhea... AEs leading to discontinuation/dose reduction: Diarrhea (<1%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21719lbl.pdf

AEs

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:53289	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:53289
ChemicalBook	CB0156314	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0156314
ChemicalBook	CB23334700	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB23334700
ChemicalBook	CB62741796	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB62741796
ChemicalBook	CB73050236	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB73050236
eMolecules	873089	https://www.emolecules.com/cgi-bin/more?vid=873089
MolPort	MolPort-003-847-014	https://www.molport.com/shop/molecule-link/MolPort-003-847-014

PubMed

Title	Date	PubMed
Donepezil management of schizophrenia with associated dementia.	2002-04	11910273
In vitro toxicity of rivastigmine and donepezil in cells of epithelial origin.	2002-03-27	11914613
A 1-year, randomized, placebo-controlled study of donepezil in patients with mild to moderate AD.	2002-03-12	11889261
How many patients complete an adequate trial of donepezil?	2002-03-08	11882749
[Risperidone in the ambulatory treatment of behavior disorders in demented patients of Alzheimer's type: a retrospective analysis].	2002-03-07	11877883
Determination of donepezil, an acetylcholinesterase inhibitor, in human plasma by high-performance liquid chromatography with ultraviolet absorbance detection.	2002-03-05	11888054
Donepezil improved the clinical state and quality of life in moderate-to-severe Alzheimer disease.	2002-03-05	11874284
A double blind placebo controlled trial of donepezil adjunctive treatment to risperidone for the cognitive impairment of schizophrenia.	2002-03-01	11904128
A 24-week, double-blind, placebo-controlled trial of donepezil in patients with Down syndrome and Alzheimer's disease--pilot study.	2002-03	11921156
Comparison of citalopram, perphenazine, and placebo for the acute treatment of psychosis and behavioral disturbances in hospitalized, demented patients.	2002-03	11870012
Therapeutic effects of an acetylcholinesterase inhibitor (donepezil) on memory in Wernicke-Korsakoff's disease.	2002-02-20	11852291
Lewy body dementia: case report and discussion.	2002-02-14	11841138
Atrophy of the substantia innominata on magnetic resonance imaging and response to donepezil treatment in Alzheimer's disease.	2002-02-08	11814647
Donepezil in the treatment of Alzheimer's disease: long-term efficacy and safety.	2002-02	11817515
Feasibility of vascular dementia treatment with cholinesterase inhibitors.	2002-02	11813286
[Alzheimer dementia. Intervening as early as possible].	2002-01-17	11847891
A new HPLC method to determine Donepezil hydrochloride in tablets.	2002-01-01	11682224
[Pharmacotherapy for the treatment of Alzheimer's disease--the present state and the development in the future].	2002-01	11808319
Economic evaluation of donepezil treatment for Alzheimer's disease in Japan.	2002	11731713
[Alzheimer dementia. Comparison of the effectiveness of cholinesterase inhibitors and gingko].	2001-12-13	11824165
A randomized, double-blind, placebo-controlled study of the efficacy and safety of donepezil in patients with Alzheimer's disease in the nursing home setting.	2001-12	11843990
Galantamine: new preparation. The fourth cholinesterase inhibitor for Alzheimer's disease.	2001-12	11824442
Unsafe prescription medication switching recommendations.	2001-12	11813938
Donepezil in schizophrenia--is it helpful? An experimental design case study.	2001-12	11782241
Alzheimer's disease: recent advances in etiology, diagnosis, and management.	2001-12	11767466
[A comparison of cholinesterase inhibitors and ginkgo extract in treatment of Alzheimer dementia].	2001-11-29	11789125
SCH 57790, a selective muscarinic M(2) receptor antagonist, releases acetylcholine and produces cognitive enhancement in laboratory animals.	2001-11-16	11728425
A case of Korsakoff's syndrome improved by high doses of donepezil.	2001-11-13	11704621
Equity in the new NHS. Evidence cannot help in all situations.	2001-11-10	11725754
Synthesis and screening for antiacetylcholinesterase activity of (1-benzyl-4-oxopiperidin-3-ylidene)methylindoles and -pyrroles related to donepezil.	2001-11-08	11689088
Ameliorative effects of azaindolizinone derivative ZSET845 on scopolamine-induced deficits in passive avoidance and radial-arm maze learning in the rat.	2001-11	11885975
[Malignant syndrome caused by a combination of bromperidol and donepezil hydrochloride in a patient with probable dementia with Lewy bodies].	2001-11	11774731
Cerebrospinal fluid acetylcholinesterase activity after long-term treatment with donepezil and rivastigmina.	2001-11	11589922
Platelet amyloid precursor protein forms in AD: a peripheral diagnostic tool and a pharmacological target.	2001-11	11589917
[Relief for caregivers. Anti-dementia drug saves costs].	2001-10-18	11697297
Treatment of tardive dyskinesia with donepezil: a pilot study.	2001-10	11816865
[Effectiveness of donepezil on several cognitive functions in patients with Alzheimer's disease over 12 months].	2001-10	11738011
Donepezil hydrochloride preserves regional cerebral blood flow in patients with Alzheimer's disease.	2001-10	11585854
[Anticholinesterase agents in Alzheimer's disease].	2001-09	11680206
A 24-week, randomized, double-blind study of donepezil in moderate to severe Alzheimer's disease.	2001-08-28	11524468
Maintaining functional and behavioral abilities in Alzheimer disease.	2001-08	11669508
Maintaining cognitive function in Alzheimer disease: how effective are current treatments?	2001-08	11669506
[A patient with probable dementia with Lewy bodies, who showed improvement of dementia and parkinsonism by the administratim of donepezil].	2001-07	11808350
Featured CME topic: dementia. Medication update.	2001-07	11531174
Donepezil hydrochloride: a treatment drug for Alzheimer's disease.	2001	11893059
Selective inhibitors of butyrylcholinesterase: a valid alternative for therapy of Alzheimer's disease?	2001	11888344
Donepezil for Alzheimer's disease: pharmacodynamic, pharmacokinetic, and clinical profiles.	2001	11830754
The beneficial effect of cholinesterase inhibitors on patients suffering from Parkinson's disease and dementia.	2001	11768630
EEG changes during long-term treatment with donepezil in Alzheimer's disease patients.	2001	11725819
Galantamine for Alzheimer's disease.	2001	11687119

Patents

Sample Use Guides

In Vivo Use Guide

Mild to Moderate Alzheimer’s Disease - 5 mg or 10 mg administered once daily Moderate to Severe Alzheim er’s Disease - 10 mg or 23 mg administered once daily A dose of 10 mg once daily can be administered once patients have been on a daily dose of 5 mg for 4 to 6 weeks. A dose of 23 mg once daily can be administered once patien ts have been on a dose of 10 mg once daily for at least 3 months

Route of Administration: Oral

In Vitro Use Guide

Donepezil inhibited freshly prepared human erythrocyte AChE with IC50 22 nM

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:35:47 GMT 2025` Edited by `admin` on `Mon Mar 31 18:35:47 GMT 2025`
Record UNII	SLF7M28SI5
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

1H-INDEN-1-ONE, 2,3-DIHYDRO-5,6-DIMETHOXYL-2-((1-(PHENYLMETHYL)-4-PIPERIDINYL)METHYL)-, ETHANEDOIOATE (1:1)

Preferred Name

English

DONEPEZIL OXALATE

Common Name

English

DONEPEZIL MONOXALATE

Common Name

English

Donepezil oxalate [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C47792