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Compound Detail

CHEMBL1678

DONEPEZIL HYDROCHLORIDE
💊 Approved Drug
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💊 Approved Drug
COc1cc2c(cc1OC)C(=O)C(CC1CCN(Cc3ccccc3)CC1)C2.Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1678
Name DONEPEZIL HYDROCHLORIDE
Phase Approved
Structure Type MOL
InChI Key XWAIAVWHZJNZQQ-UHFFFAOYSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL502
Active Moiety CHEMBL502

Known Names

Adlarity Aricept Aricept evess Aricept odt BNAG Donepezil hcl Donepezil hydrochloride Donepezil hydrochloride component of namzaric E-2020 E2020 NSC-737535 NSC-758882
10
Targets
36
Activities
2
Assay Types
23
PK Parameters
20
Publications
12
Known Names
12
Indications
1
Mechanisms

Molecular Properties

379.5
MW (Da)
4.36
ALogP
4
HBA
0
HBD
38.8
PSA (Ų)
0.75
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1996
Availability Prescription
Chirality Racemic

Routes of Administration

Oral Topical
USAN Stem -pezil
USAN Year 1997

Extended Properties

Molecular Formula C24H30ClNO3
MW 415.96
Aromatic Rings 2
Heavy Atoms 28
NP-Likeness -0.06

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Acetylcholinesterase inhibitor INHIBITOR Acetylcholinesterase ✓ ✓

Indications

Alzheimer Disease Dementia Delirium Dementia, Vascular Depressive Disorder Down Syndrome Rett Syndrome Autistic Disorder Central Nervous System Neoplasms Migraine Disorders Neuralgia Cognitive Dysfunction

Activity Summary

IC50 32 meas. best 8.24
Ki 4 meas. best 8.47

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Acetylcholinesterase
CHEMBL4780
 Ki 8.47 8.22 3.4 3
Acetylcholinesterase
CHEMBL3198
 IC50 8.24 7.105 5.7 2
Acetylcholinesterase
CHEMBL4780
 IC50 8.24 8.24 5.7 1
Acetylcholinesterase
CHEMBL4768
 IC50 8.09 8.09 8.1 1
Acetylcholinesterase
CHEMBL220
 IC50 7.94 7.512 11.6 5
Acetylcholinesterase
CHEMBL4078
 IC50 7.85 7.085 14.0 10
Unchecked
CHEMBL612545
 IC50 7.5 7.205 32.0 2
Acetylcholinesterase
CHEMBL4078
 Ki 7.4 7.4 40.0 1
Cholinesterase
CHEMBL5763
 IC50 5.58 5.255 2630.0 6
Butyrylcholinesterase
CHEMBL5077
 IC50 5.44 5.44 3600.0 1
Butyrylcholinesterase
CHEMBL3403
 IC50 5.15 5.15 7138.0 1
Cholinesterase
CHEMBL1914
 IC50 5.14 5.14 7273.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 345.35 ng.hr.mL-1 Rattus norvegicus
AUC 288.42 ng.hr.mL-1 Rattus norvegicus
CL 2.167 mL.min-1.kg-1 Homo sapiens
CL 43.0 mL.min-1.kg-1 Rattus norvegicus
CL 52.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 200.0 nM Rattus norvegicus
Cmax 300.0 nM Rattus norvegicus
Cmax 180.0 nM Rattus norvegicus
Cmax 320.0 nM Rattus norvegicus
F 100.0 % Homo sapiens
F 43.0 % Rattus norvegicus
F 36.0 % Rattus norvegicus
MRT 4.6 hr Rattus norvegicus
MRT 3.0 hr Rattus norvegicus
T1/2 70.0 hr Homo sapiens
T1/2 3.6 hr Rattus norvegicus
T1/2 2.5 hr Rattus norvegicus
Tmax 3.0 hr Homo sapiens
Tmax 1.0 hr Rattus norvegicus
Tmax 1.0 hr Rattus norvegicus
Vd 12.0 L.kg-1 Homo sapiens
Vd 11.8 L.kg-1 Rattus norvegicus
Vd 9.2 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Acetylcholinesterase Ki = 3.35 nM 8.47 Inhibitory activity was calculated for the model Acetylcholinesterase (Expt-1) 8893840
Acetylcholinesterase IC50 = 5.7 nM 8.24 Inhibition of Torpedo californica AChE 18479118
Acetylcholinesterase IC50 = 5.7 nM 8.24 Inhibitory activity against acetylcholinesterase 7490731
Acetylcholinesterase Ki = 6.73 nM 8.17 Inhibitory activity was calculated for the model Acetylcholinesterase (Expt-2) 8893840
Acetylcholinesterase IC50 = 8.12 nM 8.09 Inhibition of bovine erythrocyte AChE by Ellman's assay 18517184
Acetylcholinesterase Ki = 9.48 nM 8.02 Inhibitory activity against Acetylcholinesterase 8893840
Acetylcholinesterase IC50 = 11.6 nM 7.94 Inhibition of human erythrocyte AChE by Ellman's assay 18517184
Acetylcholinesterase IC50 = 14.0 nM 7.85 Inhibition of electric eel AChE using acetylthiocholine iodide as substrate by E... 23140986
Acetylcholinesterase IC50 = 14.0 nM 7.85 Inhibition of electric eel AChE using acetylthiocholine iodide as substrate prei... 23644208
Acetylcholinesterase IC50 = 20.0 nM 7.7 Inhibition of AChE (unknown origin) assessed as inhibition of acetylcholine hydr... 25455147
Acetylcholinesterase IC50 = 28.0 nM 7.55 Inhibition of electric eel AChE by Ellman's method 20673725
Acetylcholinesterase IC50 = 31.0 nM 7.51 Inhibition of electric eel AChE using acetylthiocholine substrate by Ellman's re... 25681712
Acetylcholinesterase IC50 = 32.0 nM 7.5 Inhibition of human AChE incubated with compounf for 5 mins before addition of s... 21429752
Acetylcholinesterase IC50 = 32.0 nM 7.5 Inhibition of human AChE by Ellman's assay 21873056
Unchecked IC50 = 32.0 nM 7.5 Inhibition of electric eel AChE type VI-S using acetylthiocholine iodide as subs... 24681070
Acetylcholinesterase Ki = 40.0 nM 7.4 Binding affinity to electric eel AChE assessed as inhibition constant by Linewea... 38229749
Acetylcholinesterase IC50 = 50.0 nM 7.3 Inhibition of electric eel AChE using acetylthiocholine iodide as substrate prei... 38229749
Acetylcholinesterase IC50 = 120.0 nM 6.92 Inhibition of AChE (unknown origin) using acetylcholine as substrate preincubate... 28552337
Acetylcholinesterase IC50 = 120.0 nM 6.92 Inhibition of electric eel AChE by modified Ellman method 21621414
Acetylcholinesterase IC50 = 120.0 nM 6.92 Inhibition of electric eel AChE using acetylcholine as substrate measured every ... 22142546

Literature References

PubMed DOI Target Context # Activities
21148081 10.1124/dmd.110.035964 Rattus norvegicus 24
29635167 10.1016/j.ejmech.2018.03.082 Mus musculus 10
21148081 10.1124/dmd.110.035964 Blood 6
21148081 10.1124/dmd.110.035964 Unchecked 5
21148081 10.1124/dmd.110.035964 Homo sapiens 5
18517184 10.1021/jm8001313 Acetylcholinesterase 4
21148081 10.1124/dmd.110.035964 ADMET 3
8893840 10.1021/jm950596e Acetylcholinesterase 3
29227101 10.1021/acs.jmedchem.7b01086 Mus musculus 3
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
21148081 10.1124/dmd.110.035964 Acetylcholinesterase 2
21429752 10.1016/j.bmc.2011.02.030 Acetylcholinesterase 2
33476932 10.1016/j.ejmech.2021.113154 Mus musculus 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
21873056 10.1016/j.bmcl.2011.07.091 Unchecked 2
21873056 10.1016/j.bmcl.2011.07.091 Acetylcholinesterase 2
38229749 10.1021/acsmedchemlett.3c00467 Acetylcholinesterase 2
30578075 10.1016/j.bmc.2018.12.007 Acetylcholinesterase 2
30578075 10.1016/j.bmc.2018.12.007 Mus musculus 2
38911158 10.1039/d4md00113c Unchecked 1

Data from ChEMBL 36 via Core Engine