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
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)
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.
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 Date8.4888001E11 |
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 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%) Sources: Page: p. 50Diarrhea (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 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) 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 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%) 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 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
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: 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 |
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 |
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 |
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
Title | Date | PubMed |
---|---|---|
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 |
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
by
admin
on
Edited
Fri Dec 15 16:45:46 UTC 2023
by
admin
on
Fri Dec 15 16:45:46 UTC 2023
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Record UNII |
SLF7M28SI5
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Record Status |
Validated (UNII)
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Record Version |
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-
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Classification Tree | Code System | Code | ||
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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
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Code System | Code | Type | Description | ||
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C87489
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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
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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
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PRIMARY | |||
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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
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PRIMARY |
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |