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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 of DONEPEZIL OXALATE

SMILES

OC(=O)C(O)=O.COC1=CC2=C(C=C1OC)C(=O)C(CC3CCN(CC4=CC=CC=C4)CC3)C2

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 ( + / - )

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
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

8.4888001E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
34.1 ng/mL
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
2889.3 ng × h/mL
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
72.7 h
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
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
4.4%
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%
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

Doses

DosePopulationAdverse events​
175 mg single, transdermal
Dose: 175 mg
Route: transdermal
Route: single
Dose: 175 mg
Sources:
healthy, 24.9±3.3 years
n = 9
Health Status: healthy
Age Group: 24.9±3.3 years
Sex: M
Population Size: 9
Sources:
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:
healthy, 24.9±3.3 years
n = 9
Health Status: healthy
Age Group: 24.9±3.3 years
Sex: M
Population Size: 9
Sources:
23 mg 1 times / day steady, oral
Dose: 23 mg, 1 times / day
Route: oral
Route: steady
Dose: 23 mg, 1 times / day
Sources: Page: p. 50
unhealthy, 73.9 years
n = 967
Health Status: unhealthy
Condition: Alzheimer disease
Age Group: 73.9 years
Sex: M+F
Population Size: 967
Sources: Page: p. 50
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: Page: p. 50
50 mg single, oral
Overdose
Dose: 50 mg
Route: oral
Route: single
Dose: 50 mg
Sources:
unhealthy, 79 years
n = 1
Health Status: unhealthy
Condition: Alzheimer disease
Age Group: 79 years
Sex: F
Population Size: 1
Sources:
Other AEs: Nausea, Vomiting...
Other AEs:
Nausea (1 patient)
Vomiting (1 patient)
Bradycardia (1 patient)
Sources:
30 mg 1 times / day steady, oral
Dose: 30 mg, 1 times / day
Route: oral
Route: steady
Dose: 30 mg, 1 times / day
Sources:
unhealthy, 80 years
n = 1
Health Status: unhealthy
Condition: Alzheimer disease
Age Group: 80 years
Sex: F
Population Size: 1
Sources:
Disc. AE: Myoclonus...
AEs leading to
discontinuation/dose reduction:
Myoclonus (1 patient)
Sources:
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:
unhealthy, adult
n = 315
Health Status: unhealthy
Age Group: adult
Population Size: 315
Sources:
Other AEs: Diarrhea, Nausea...
Other AEs:
Diarrhea (3%)
Nausea (3%)
Vomiting (2%)
Sources:
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:
unhealthy, adult
n = 350
Health Status: unhealthy
Age Group: adult
Population Size: 350
Sources:
Disc. AE: Diarrhea...
AEs leading to
discontinuation/dose reduction:
Diarrhea (<1%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Syncope 0.2%
Disc. AE
23 mg 1 times / day steady, oral
Dose: 23 mg, 1 times / day
Route: oral
Route: steady
Dose: 23 mg, 1 times / day
Sources: Page: p. 50
unhealthy, 73.9 years
n = 967
Health Status: unhealthy
Condition: Alzheimer disease
Age Group: 73.9 years
Sex: M+F
Population Size: 967
Sources: Page: p. 50
Anorexia 0.3%
Disc. AE
23 mg 1 times / day steady, oral
Dose: 23 mg, 1 times / day
Route: oral
Route: steady
Dose: 23 mg, 1 times / day
Sources: Page: p. 50
unhealthy, 73.9 years
n = 967
Health Status: unhealthy
Condition: Alzheimer disease
Age Group: 73.9 years
Sex: M+F
Population Size: 967
Sources: Page: p. 50
Headache 0.4%
Disc. AE
23 mg 1 times / day steady, oral
Dose: 23 mg, 1 times / day
Route: oral
Route: steady
Dose: 23 mg, 1 times / day
Sources: Page: p. 50
unhealthy, 73.9 years
n = 967
Health Status: unhealthy
Condition: Alzheimer disease
Age Group: 73.9 years
Sex: M+F
Population Size: 967
Sources: Page: p. 50
QT interval prolonged 0.4%
Disc. AE
23 mg 1 times / day steady, oral
Dose: 23 mg, 1 times / day
Route: oral
Route: steady
Dose: 23 mg, 1 times / day
Sources: Page: p. 50
unhealthy, 73.9 years
n = 967
Health Status: unhealthy
Condition: Alzheimer disease
Age Group: 73.9 years
Sex: M+F
Population Size: 967
Sources: Page: p. 50
Aggression 0.5%
Disc. AE
23 mg 1 times / day steady, oral
Dose: 23 mg, 1 times / day
Route: oral
Route: steady
Dose: 23 mg, 1 times / day
Sources: Page: p. 50
unhealthy, 73.9 years
n = 967
Health Status: unhealthy
Condition: Alzheimer disease
Age Group: 73.9 years
Sex: M+F
Population Size: 967
Sources: Page: p. 50
Somnolence 0.6%
Disc. AE
23 mg 1 times / day steady, oral
Dose: 23 mg, 1 times / day
Route: oral
Route: steady
Dose: 23 mg, 1 times / day
Sources: Page: p. 50
unhealthy, 73.9 years
n = 967
Health Status: unhealthy
Condition: Alzheimer disease
Age Group: 73.9 years
Sex: M+F
Population Size: 967
Sources: Page: p. 50
Bradycardia 0.7%
Disc. AE
23 mg 1 times / day steady, oral
Dose: 23 mg, 1 times / day
Route: oral
Route: steady
Dose: 23 mg, 1 times / day
Sources: Page: p. 50
unhealthy, 73.9 years
n = 967
Health Status: unhealthy
Condition: Alzheimer disease
Age Group: 73.9 years
Sex: M+F
Population Size: 967
Sources: Page: p. 50
Confusional state 0.7%
Disc. AE
23 mg 1 times / day steady, oral
Dose: 23 mg, 1 times / day
Route: oral
Route: steady
Dose: 23 mg, 1 times / day
Sources: Page: p. 50
unhealthy, 73.9 years
n = 967
Health Status: unhealthy
Condition: Alzheimer disease
Age Group: 73.9 years
Sex: M+F
Population Size: 967
Sources: Page: p. 50
Agitation 0.8%
Disc. AE
23 mg 1 times / day steady, oral
Dose: 23 mg, 1 times / day
Route: oral
Route: steady
Dose: 23 mg, 1 times / day
Sources: Page: p. 50
unhealthy, 73.9 years
n = 967
Health Status: unhealthy
Condition: Alzheimer disease
Age Group: 73.9 years
Sex: M+F
Population Size: 967
Sources: Page: p. 50
Dizziness 1.1%
Disc. AE
23 mg 1 times / day steady, oral
Dose: 23 mg, 1 times / day
Route: oral
Route: steady
Dose: 23 mg, 1 times / day
Sources: Page: p. 50
unhealthy, 73.9 years
n = 967
Health Status: unhealthy
Condition: Alzheimer disease
Age Group: 73.9 years
Sex: M+F
Population Size: 967
Sources: Page: p. 50
Diarrhea 1.7%
Disc. AE
23 mg 1 times / day steady, oral
Dose: 23 mg, 1 times / day
Route: oral
Route: steady
Dose: 23 mg, 1 times / day
Sources: Page: p. 50
unhealthy, 73.9 years
n = 967
Health Status: unhealthy
Condition: Alzheimer disease
Age Group: 73.9 years
Sex: M+F
Population Size: 967
Sources: Page: p. 50
Nausea 1.9%
Disc. AE
23 mg 1 times / day steady, oral
Dose: 23 mg, 1 times / day
Route: oral
Route: steady
Dose: 23 mg, 1 times / day
Sources: Page: p. 50
unhealthy, 73.9 years
n = 967
Health Status: unhealthy
Condition: Alzheimer disease
Age Group: 73.9 years
Sex: M+F
Population Size: 967
Sources: Page: p. 50
Vomiting 2.9%
Disc. AE
23 mg 1 times / day steady, oral
Dose: 23 mg, 1 times / day
Route: oral
Route: steady
Dose: 23 mg, 1 times / day
Sources: Page: p. 50
unhealthy, 73.9 years
n = 967
Health Status: unhealthy
Condition: Alzheimer disease
Age Group: 73.9 years
Sex: M+F
Population Size: 967
Sources: Page: p. 50
Bradycardia 1 patient
50 mg single, oral
Overdose
Dose: 50 mg
Route: oral
Route: single
Dose: 50 mg
Sources:
unhealthy, 79 years
n = 1
Health Status: unhealthy
Condition: Alzheimer disease
Age Group: 79 years
Sex: F
Population Size: 1
Sources:
Nausea 1 patient
50 mg single, oral
Overdose
Dose: 50 mg
Route: oral
Route: single
Dose: 50 mg
Sources:
unhealthy, 79 years
n = 1
Health Status: unhealthy
Condition: Alzheimer disease
Age Group: 79 years
Sex: F
Population Size: 1
Sources:
Vomiting 1 patient
50 mg single, oral
Overdose
Dose: 50 mg
Route: oral
Route: single
Dose: 50 mg
Sources:
unhealthy, 79 years
n = 1
Health Status: unhealthy
Condition: Alzheimer disease
Age Group: 79 years
Sex: F
Population Size: 1
Sources:
Myoclonus 1 patient
Disc. AE
30 mg 1 times / day steady, oral
Dose: 30 mg, 1 times / day
Route: oral
Route: steady
Dose: 30 mg, 1 times / day
Sources:
unhealthy, 80 years
n = 1
Health Status: unhealthy
Condition: Alzheimer disease
Age Group: 80 years
Sex: F
Population Size: 1
Sources:
Vomiting 2%
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:
unhealthy, adult
n = 315
Health Status: unhealthy
Age Group: adult
Population Size: 315
Sources:
Diarrhea 3%
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:
unhealthy, adult
n = 315
Health Status: unhealthy
Age Group: adult
Population Size: 315
Sources:
Nausea 3%
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:
unhealthy, adult
n = 315
Health Status: unhealthy
Age Group: adult
Population Size: 315
Sources:
Diarrhea <1%
Disc. AE
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:
unhealthy, adult
n = 350
Health Status: unhealthy
Age Group: adult
Population Size: 350
Sources:
PubMed

PubMed

TitleDatePubMed
Switching previous therapies for Alzheimer's disease to galantamine.
2001
Effects of washout and dose-escalation periods on the efficacy, safety, and tolerability of galantamine in patients previously treated with donepezil: ongoing clinical trials.
2001
Prevalence, costs, and treatment of Alzheimer's disease and related dementia: a managed care perspective.
2001 Aug
A 1-year, randomized, placebo-controlled study of donepezil in patients with mild to moderate AD.
2001 Aug 14
A 1-year, placebo-controlled preservation of function survival study of donepezil in AD patients.
2001 Aug 14
Galantamine: new preparation. The fourth cholinesterase inhibitor for Alzheimer's disease.
2001 Dec
[Alzheimer dementia. Comparison of the effectiveness of cholinesterase inhibitors and gingko].
2001 Dec 13
Donepezil-induced REM sleep augmentation enhances memory performance in elderly, healthy persons.
2001 Feb
Successful use of donepezil for the treatment of dementia with Lewy bodies.
2001 Feb
Donepezil, rivastigmine, and vitamin E in Alzheimer disease: a combined P300 event-related potentials/neuropsychologic evaluation over 6 months.
2001 Jan-Feb
[Aphasia and dementia].
2001 Jul
Open-label study of donepezil in traumatic brain injury.
2001 Jul
Equity in the new NHS: hard lessons from implementing a local healthcare policy on donepezil.
2001 Jul 28
Central and peripheral activity of cholinesterase inhibitors as revealed by yawning and fasciculation in rats.
2001 Mar
Analysis and enantioresolution of donepezil by capillary electrophoresis.
2001 Mar
Actigraphic sleep-wake patterns and urinary 6-sulfatoxymelatonin excretion in patients with Alzheimer's disease.
2001 May
Structure-based 3D QSAR and design of novel acetylcholinesterase inhibitors.
2001 May
Donepezil in the treatment of opioid-induced sedation: report of six cases.
2001 May
Alzheimer's disease and related disorders.
2001 May
[Malignant syndrome caused by a combination of bromperidol and donepezil hydrochloride in a patient with probable dementia with Lewy bodies].
2001 Nov
Equity in the new NHS. Evidence cannot help in all situations.
2001 Nov 10
SCH 57790, a selective muscarinic M(2) receptor antagonist, releases acetylcholine and produces cognitive enhancement in laboratory animals.
2001 Nov 16
A case of Korsakoff's syndrome improved by high doses of donepezil.
2001 Nov-Dec
Treatment of tardive dyskinesia with donepezil: a pilot study.
2001 Oct
[Anticholinesterase agents in Alzheimer's disease].
2001 Sep
Donepezil for Alzheimer's disease: pharmacodynamic, pharmacokinetic, and clinical profiles.
2001 Winter
Economic evaluation of donepezil treatment for Alzheimer's disease in Japan.
2002
Atrophy of the substantia innominata on magnetic resonance imaging and response to donepezil treatment in Alzheimer's disease.
2002 Feb 8
[Alzheimer dementia. Intervening as early as possible].
2002 Jan 17
A 24-week, double-blind, placebo-controlled trial of donepezil in patients with Down syndrome and Alzheimer's disease--pilot study.
2002 Mar
Donepezil improved the clinical state and quality of life in moderate-to-severe Alzheimer disease.
2002 Mar-Apr
Patents

Sample Use Guides

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
Donepezil inhibited freshly prepared human erythrocyte AChE with IC50 22 nM
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:45:46 UTC 2023
Edited
by admin
on Fri Dec 15 16:45:46 UTC 2023
Record UNII
SLF7M28SI5
Record Status Validated (UNII)
Record Version
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Name Type Language
DONEPEZIL OXALATE
WHO-DD  
Common Name English
DONEPEZIL MONOXALATE
Common Name English
Donepezil oxalate [WHO-DD]
Common Name English
1H-INDEN-1-ONE, 2,3-DIHYDRO-5,6-DIMETHOXYL-2-((1-(PHENYLMETHYL)-4-PIPERIDINYL)METHYL)-, ETHANEDOIOATE (1:1)
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47792
Created by admin on Fri Dec 15 16:45:47 UTC 2023 , Edited by admin on Fri Dec 15 16:45:47 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C87489
Created by admin on Fri Dec 15 16:45:47 UTC 2023 , Edited by admin on Fri Dec 15 16:45:47 UTC 2023
PRIMARY
CAS
870555-76-3
Created by admin on Fri Dec 15 16:45:47 UTC 2023 , Edited by admin on Fri Dec 15 16:45:47 UTC 2023
PRIMARY
PUBCHEM
11397232
Created by admin on Fri Dec 15 16:45:47 UTC 2023 , Edited by admin on Fri Dec 15 16:45:47 UTC 2023
PRIMARY
FDA UNII
SLF7M28SI5
Created by admin on Fri Dec 15 16:45:47 UTC 2023 , Edited by admin on Fri Dec 15 16:45:47 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY