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Details

Stereochemistry RACEMIC
Molecular Formula C24H29NO3.ClH.H2O
Molecular Weight 433.968
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DONEPEZIL HYDROCHLORIDE MONOHYDRATE

SMILES

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

InChI

InChIKey=HLJIZAKUNCTCQX-UHFFFAOYSA-N
InChI=1S/C24H29NO3.ClH.H2O/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;1H2

HIDE SMILES / InChI
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

1996
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
Health Status: healthy
Age Group: 24.9±3.3 years
Sex: M
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
Health Status: healthy
Age Group: 24.9±3.3 years
Sex: M
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:
unhealthy, 73.9 years
Health Status: unhealthy
Age Group: 73.9 years
Sex: M+F
Sources:
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:
50 mg single, oral
Overdose
Dose: 50 mg
Route: oral
Route: single
Dose: 50 mg
Sources:
unhealthy, 79 years
Health Status: unhealthy
Age Group: 79 years
Sex: F
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
Health Status: unhealthy
Age Group: 80 years
Sex: F
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
Health Status: unhealthy
Age Group: adult
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
Health Status: unhealthy
Age Group: adult
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:
unhealthy, 73.9 years
Health Status: unhealthy
Age Group: 73.9 years
Sex: M+F
Sources:
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:
unhealthy, 73.9 years
Health Status: unhealthy
Age Group: 73.9 years
Sex: M+F
Sources:
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:
unhealthy, 73.9 years
Health Status: unhealthy
Age Group: 73.9 years
Sex: M+F
Sources:
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:
unhealthy, 73.9 years
Health Status: unhealthy
Age Group: 73.9 years
Sex: M+F
Sources:
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:
unhealthy, 73.9 years
Health Status: unhealthy
Age Group: 73.9 years
Sex: M+F
Sources:
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:
unhealthy, 73.9 years
Health Status: unhealthy
Age Group: 73.9 years
Sex: M+F
Sources:
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:
unhealthy, 73.9 years
Health Status: unhealthy
Age Group: 73.9 years
Sex: M+F
Sources:
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:
unhealthy, 73.9 years
Health Status: unhealthy
Age Group: 73.9 years
Sex: M+F
Sources:
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:
unhealthy, 73.9 years
Health Status: unhealthy
Age Group: 73.9 years
Sex: M+F
Sources:
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:
unhealthy, 73.9 years
Health Status: unhealthy
Age Group: 73.9 years
Sex: M+F
Sources:
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:
unhealthy, 73.9 years
Health Status: unhealthy
Age Group: 73.9 years
Sex: M+F
Sources:
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:
unhealthy, 73.9 years
Health Status: unhealthy
Age Group: 73.9 years
Sex: M+F
Sources:
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:
unhealthy, 73.9 years
Health Status: unhealthy
Age Group: 73.9 years
Sex: M+F
Sources:
Bradycardia 1 patient
50 mg single, oral
Overdose
Dose: 50 mg
Route: oral
Route: single
Dose: 50 mg
Sources:
unhealthy, 79 years
Health Status: unhealthy
Age Group: 79 years
Sex: F
Sources:
Nausea 1 patient
50 mg single, oral
Overdose
Dose: 50 mg
Route: oral
Route: single
Dose: 50 mg
Sources:
unhealthy, 79 years
Health Status: unhealthy
Age Group: 79 years
Sex: F
Sources:
Vomiting 1 patient
50 mg single, oral
Overdose
Dose: 50 mg
Route: oral
Route: single
Dose: 50 mg
Sources:
unhealthy, 79 years
Health Status: unhealthy
Age Group: 79 years
Sex: F
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
Health Status: unhealthy
Age Group: 80 years
Sex: F
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
Health Status: unhealthy
Age Group: adult
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
Health Status: unhealthy
Age Group: adult
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
Health Status: unhealthy
Age Group: adult
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
Health Status: unhealthy
Age Group: adult
Sources:
PubMed

PubMed

TitleDatePubMed
The beneficial effect of cholinesterase inhibitors on patients suffering from Parkinson's disease and dementia.
2001
Galantamine for Alzheimer's disease.
2001
Pharmacokinetic rationale for switching from donepezil to galantamine.
2001
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
Pharmacokinetic profiles of current therapies for Alzheimer's disease: implications for switching to galantamine.
2001
Clinical and cost-effectiveness of donepezil, rivastigmine and galantamine for Alzheimer's disease: a rapid and systematic review.
2001
Muscarinic agonists and antagonists in the treatment of Alzheimer's disease.
2001 Apr
Present and future pharmacotherapeutic options for adult attention deficit/hyperactivity disorder.
2001 Apr
Maintaining functional and behavioral abilities in Alzheimer disease.
2001 Aug
Maintaining cognitive function in Alzheimer disease: how effective are current treatments?
2001 Aug
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 Dec
Unsafe prescription medication switching recommendations.
2001 Dec
Donepezil in schizophrenia--is it helpful? An experimental design case study.
2001 Dec
Alzheimer's disease: recent advances in etiology, diagnosis, and management.
2001 Dec
The use of medications for cognitive enhancement.
2001 Feb
Donepezil-induced REM sleep augmentation enhances memory performance in elderly, healthy persons.
2001 Feb
[Early recognition not hopeless. Alzheimer disease can be delayed].
2001 Feb 8
Efficacy of acetylcholinesterase inhibitors versus nootropics in Alzheimer's disease: a retrospective, longitudinal study.
2001 Jan-Feb
[Aphasia and dementia].
2001 Jul
Use of cholinesterase inhibitors for treatment of Alzheimer disease.
2001 Jul
Open-label study of donepezil in traumatic brain injury.
2001 Jul
Chronic donepezil treatment is associated with slowed cognitive decline in Alzheimer's disease.
2001 Jul-Aug
Huperzine A and donepezil protect rat pheochromocytoma cells against oxygen-glucose deprivation.
2001 Jun 22
Anticholinesterase drugs for alcoholic Korsakoff syndrome.
2001 Mar
Central and peripheral activity of cholinesterase inhibitors as revealed by yawning and fasciculation in rats.
2001 Mar
Amyloid precursor protein in platelets of patients with Alzheimer disease: effect of acetylcholinesterase inhibitor treatment.
2001 Mar
Open-label, multicenter, phase 3 extension study of the safety and efficacy of donepezil in patients with Alzheimer disease.
2001 Mar
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
Ameliorative effects of azaindolizinone derivative ZSET845 on scopolamine-induced deficits in passive avoidance and radial-arm maze learning in the rat.
2001 Nov
[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
[A comparison of cholinesterase inhibitors and ginkgo extract in treatment of Alzheimer dementia].
2001 Nov 29
Synthesis and screening for antiacetylcholinesterase activity of (1-benzyl-4-oxopiperidin-3-ylidene)methylindoles and -pyrroles related to donepezil.
2001 Nov 8
A case of Korsakoff's syndrome improved by high doses of donepezil.
2001 Nov-Dec
[Effectiveness of donepezil on several cognitive functions in patients with Alzheimer's disease over 12 months].
2001 Oct
[Relief for caregivers. Anti-dementia drug saves costs].
2001 Oct 18
Economic evaluation of donepezil treatment for Alzheimer's disease in Japan.
2002
Feasibility of vascular dementia treatment with cholinesterase inhibitors.
2002 Feb
Atrophy of the substantia innominata on magnetic resonance imaging and response to donepezil treatment in Alzheimer's disease.
2002 Feb 8
A new HPLC method to determine Donepezil hydrochloride in tablets.
2002 Jan 1
A 24-week, double-blind, placebo-controlled trial of donepezil in patients with Down syndrome and Alzheimer's disease--pilot study.
2002 Mar
A double blind placebo controlled trial of donepezil adjunctive treatment to risperidone for the cognitive impairment of schizophrenia.
2002 Mar 1
Determination of donepezil, an acetylcholinesterase inhibitor, in human plasma by high-performance liquid chromatography with ultraviolet absorbance detection.
2002 Mar 5
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
Name Type Language
DONEPEZIL HYDROCHLORIDE MONOHYDRATE [EP MONOGRAPH]
Preferred Name English
DONEPEZIL HYDROCHLORIDE MONOHYDRATE
Common Name English
1H-INDEN-1-ONE, 2,3-DIHYDRO-5,6-DIMETHOXY-2-((1-(PHENYLMETHYL)-4-PIPERIDINYL)METHYL)-, HYDROCHLORIDE, HYDRATE (1:1:1)
Systematic Name English
Donepezil hydrochloride monohydrate [WHO-DD]
Common Name English
1H-INDEN-1-ONE, 2,3-DIHYDRO-5,6-DIMETHOXY-2-((1-(PHENYLMETHYL)-4-PIPERIDINYL)METHYL)-, HYDROCHLORIDE, MONOHYDRATE
Systematic Name English
Code System Code Type Description
FDA UNII
7KZL5YRL6W
Created by admin on Mon Mar 31 22:17:46 GMT 2025 , Edited by admin on Mon Mar 31 22:17:46 GMT 2025
PRIMARY
PUBCHEM
11697764
Created by admin on Mon Mar 31 22:17:46 GMT 2025 , Edited by admin on Mon Mar 31 22:17:46 GMT 2025
PRIMARY
CAS
884740-09-4
Created by admin on Mon Mar 31 22:17:46 GMT 2025 , Edited by admin on Mon Mar 31 22:17:46 GMT 2025
PRIMARY
EPA CompTox
DTXSID50470774
Created by admin on Mon Mar 31 22:17:46 GMT 2025 , Edited by admin on Mon Mar 31 22:17:46 GMT 2025
PRIMARY
EVMPD
SUB36426
Created by admin on Mon Mar 31 22:17:46 GMT 2025 , Edited by admin on Mon Mar 31 22:17:46 GMT 2025
PRIMARY
SMS_ID
100000128835
Created by admin on Mon Mar 31 22:17:46 GMT 2025 , Edited by admin on Mon Mar 31 22:17:46 GMT 2025
PRIMARY