Details
Stereochemistry | RACEMIC |
Molecular Formula | C24H29NO3 |
Molecular Weight | 379.492 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C(OC)C=C2C(=O)C(CC3CCN(CC4=CC=CC=C4)CC3)CC2=C1
InChI
InChIKey=ADEBPBSSDYVVLD-UHFFFAOYSA-N
InChI=1S/C24H29NO3/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
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
6.7 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | ARICEPT Approved UseDonepezil 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 Date1996 |
Cmax
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 |
T1/2
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 |
Funbound
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: |
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%) Sources: 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%) |
50 mg single, oral Overdose |
unhealthy, 79 years |
Other AEs: Nausea, Vomiting... Other AEs: Nausea (1 patient) Sources: Vomiting (1 patient) Bradycardia (1 patient) |
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 |
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%) Sources: Nausea (3%) Vomiting (2%) |
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
AE | Significance | Dose | Population |
---|---|---|---|
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 |
unhealthy, 79 years |
Nausea | 1 patient | 50 mg single, oral Overdose |
unhealthy, 79 years |
Vomiting | 1 patient | 50 mg single, oral Overdose |
unhealthy, 79 years |
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 |
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
Title | Date | PubMed |
---|---|---|
Donepezil hydrochloride: a treatment drug for Alzheimer's disease. | 2001 |
|
Selective inhibitors of butyrylcholinesterase: a valid alternative for therapy of Alzheimer's disease? | 2001 |
|
EEG changes during long-term treatment with donepezil in Alzheimer's disease patients. | 2001 |
|
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 |
|
Unsafe prescription medication switching recommendations. | 2001 Dec |
|
Treatment of tardive dyskinesia with donepezil. | 2001 Feb |
|
Successful use of donepezil for the treatment of dementia with Lewy bodies. | 2001 Feb |
|
Effect of donepezil on brain acetylcholinesterase activity in patients with AD measured by PET. | 2001 Feb 13 |
|
[A patient with probable dementia with Lewy bodies, who showed improvement of dementia and parkinsonism by the administratim of donepezil]. | 2001 Jul |
|
Pisa syndrome due to a cholinesterase inhibitor (donepezil): a case report. | 2001 Jul |
|
[Aphasia and dementia]. | 2001 Jul |
|
Newest developments in dementia treatment and prevention. | 2001 Jul-Aug |
|
Anticholinesterase drugs for alcoholic Korsakoff syndrome. | 2001 Mar |
|
Open-label, multicenter, phase 3 extension study of the safety and efficacy of donepezil in patients with Alzheimer disease. | 2001 Mar |
|
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 |
|
[Risperidone in the ambulatory treatment of behavior disorders in demented patients of Alzheimer's type: a retrospective analysis]. | 2001 Nov-Dec |
|
Treatment of tardive dyskinesia with donepezil: a pilot study. | 2001 Oct |
|
[Effectiveness of donepezil on several cognitive functions in patients with Alzheimer's disease over 12 months]. | 2001 Oct |
|
Economic evaluation of donepezil treatment for Alzheimer's disease in Japan. | 2002 |
|
Donepezil in the treatment of Alzheimer's disease: long-term efficacy and safety. | 2002 Feb |
|
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 |
|
[Pharmacotherapy for the treatment of Alzheimer's disease--the present state and the development in the future]. | 2002 Jan |
|
A new HPLC method to determine Donepezil hydrochloride in tablets. | 2002 Jan 1 |
|
Comparison of citalopram, perphenazine, and placebo for the acute treatment of psychosis and behavioral disturbances in hospitalized, demented patients. | 2002 Mar |
|
A double blind placebo controlled trial of donepezil adjunctive treatment to risperidone for the cognitive impairment of schizophrenia. | 2002 Mar 1 |
|
A 1-year, randomized, placebo-controlled study of donepezil in patients with mild to moderate AD. | 2002 Mar 12 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16570913
Donepezil inhibited freshly prepared human erythrocyte AChE with IC50 22 nM
Substance Class |
Chemical
Created
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Record UNII |
8SSC91326P
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Record Status |
Validated (UNII)
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NDF-RT |
N0000175723
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WHO-VATC |
QN06DA02
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NDF-RT |
N0000000177
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WHO-VATC |
QN06DA52
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WHO-ATC |
N06DA52
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LIVERTOX |
NBK548197
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WHO-ATC |
N06DA53
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WHO-ATC |
N06DA02
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NCI_THESAURUS |
C47792
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135447
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120014-06-4
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8SSC91326P
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8SSC91326P
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DONEPEZIL
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53289
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C076946
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m4738
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7517
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946
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DB00843
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CHEMBL502
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SUB06362MIG
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C66874
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DTXSID8048317
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3152
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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ACTIVE MOIETY |