Compound Detail

CHEMBL502

DONEPEZIL

💊 Approved Drug

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💊 Approved Drug

COc1cc2c(cc1OC)C(=O)C(CC1CCN(Cc3ccccc3)CC1)C2

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL502
Name	DONEPEZIL
Phase	Approved
Structure Type	MOL
InChI Key	ADEBPBSSDYVVLD-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

D-797 Donaz Donepezil Donepezilo

Targets

718

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

379.5

MW (Da)

4.36

ALogP

HBA

HBD

38.8

PSA (Å²)

0.75

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1996
Availability	Prescription
Chirality	Racemic

Routes of Administration

Oral Topical

Flags

Natural Product

USAN Stem	-pezil
USAN Year	1997

Extended Properties

Molecular Formula	C24H29NO3
MW	379.50
Aromatic Rings	2
Heavy Atoms	28
NP-Likeness	-0.06

Indications

Dementia Alzheimer Disease Anxiety Aphasia Cognitive Dysfunction Dementia, Vascular Depressive Disorder Ischemic Stroke Multiple Sclerosis Neoplasms Parkinson Disease Schizophrenia Stroke Child Development Disorders, Pervasive Cocaine-Related Disorders Delirium Diabetes Mellitus, Type 2 Fragile X Syndrome Neuralgia Supranuclear Palsy, Progressive

ATC Classification

N06DA02

donepezil

Level 1: NERVOUS SYSTEM

Level 2: PSYCHOANALEPTICS

Activity Summary

IC50 694 meas. best 8.77

Ki 21 meas. best 8.54

Kd 2 meas. best 8.1

EC50 1 meas. best 7.37

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Acetylcholinesterase CHEMBL3199	IC50	8.77	7.8076	1.7	34
Acetylcholinesterase CHEMBL220	IC50	8.7	7.6697	2.0	155
Acetylcholinesterase CHEMBL4768	Ki	8.54	8.54	2.9	2
Acetylcholinesterase CHEMBL4768	IC50	8.38	8.105	4.2	4
Acetylcholinesterase CHEMBL4078	Ki	8.37	7.7075	4.2	4
Cholinesterase CHEMBL5763	IC50	8.34	5.5153	4.6	131
Choline O-acetyltransferase CHEMBL3945	IC50	8.28	8.28	5.3	1
Acetylcholinesterase CHEMBL3198	IC50	8.27	6.9489	5.4	9
Acetylcholinesterase CHEMBL4078	IC50	8.17	7.485	6.7	165
Acetylcholinesterase CHEMBL220	Ki	8.14	7.79	7.2	7
Acetylcholinesterase CHEMBL220	Kd	8.1	8.1	8.0	1
cGMP-specific 3',5'-cyclic phosphodiesterase CHEMBL1827	IC50	7.96	7.96	11.0	1
Acetylcholinesterase CHEMBL4780	IC50	7.92	7.63	12.0	4
Cholinesterase CHEMBL1914	IC50	7.85	5.3895	14.0	91
Sigma non-opioid intracellular receptor 1 CHEMBL287	Ki	7.84	7.84	14.6	2
Sigma non-opioid intracellular receptor 1 CHEMBL4153	Ki	7.84	7.84	14.6	2
Beta-secretase 1 CHEMBL4822	IC50	7.75	6.5075	18.0	8
Acetylcholine receptor subunit epsilon CHEMBL2484	IC50	7.49	7.49	32.4	1
Acetylcholinesterase CHEMBL220	EC50	7.37	7.37	43.0	1
MCF7 CHEMBL387	IC50	7.22	7.22	60.0	1
HFF CHEMBL614071	IC50	7.04	7.04	91.0	1
SH-SY5Y CHEMBL614910	IC50	6.52	4.778	300.0	5
Histamine H3 receptor CHEMBL264	IC50	6.46	6.46	350.0	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	6.19	5.65	640.0	3
Butyrylcholinesterase CHEMBL5077	Ki	6.19	6.19	640.0	2
NIH3T3 CHEMBL614822	IC50	5.9	5.9	1260.0	1
Butyrylcholinesterase CHEMBL3403	IC50	5.89	4.985	1280.0	22
BV-2 CHEMBL614781	IC50	5.81	5.81	1540.0	1
Cholinesterase CHEMBL2528	IC50	5.7	5.425	1992.0	2
Cholinesterase CHEMBL5763	Ki	5.67	5.67	2140.0	1
Butyrylcholinesterase CHEMBL5077	IC50	5.54	5.33	2900.0	5
Unchecked CHEMBL612545	IC50	5.47	4.7633	3400.0	15
MAP/microtubule affinity-regulating kinase 4 CHEMBL5754	IC50	5.28	5.28	5300.0	1
Cholinesterase CHEMBL5763	Kd	5.14	5.14	7200.0	1
Cholinesterase CHEMBL1914	Ki	4.9	4.9	12540.0	1
Amine oxidase [flavin-containing] B CHEMBL2993	IC50	4.82	4.82	15000.0	3
Amine oxidase [flavin-containing] B CHEMBL2039	IC50	4.82	4.76	15000.0	3
ATP-dependent translocase ABCB1 CHEMBL4302	IC50	4.46	4.46	34850.0	1
Voltage-gated L-type calcium channel CHEMBL2095229	IC50	4.46	4.46	34300.0	1
3',5'-cyclic-AMP phosphodiesterase 4D CHEMBL288	IC50	4.44	4.44	36000.0	1
U-87 MG CHEMBL614247	IC50	4.33	4.33	47240.0	1
Cytochrome P450 3A4 CHEMBL340	IC50	4.26	4.26	54680.0	1
HT-22 CHEMBL614316	IC50	4.25	4.25	56420.0	1
ATP-binding cassette sub-family C member 4 CHEMBL1743128	IC50	4.14	4.14	72900.0	1
Bile salt export pump CHEMBL6020	IC50	4.11	4.11	78000.0	1
Amyloid-beta precursor protein CHEMBL2487	IC50	4.06	4.06	87410.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	3702.02	ng.hr.mL-1	Homo sapiens
CL	-	-	Homo sapiens
CL	0.001	uL/min	Homo sapiens
CL	14.4	mL.min-1.g-1	Rattus norvegicus
CL	17.6	mL.min-1.g-1	Rattus norvegicus
CL	9.6	mL.min-1.g-1	Rattus norvegicus
CL	34.8	mL.min-1.g-1	Mus musculus
F	50.0	%	Canis lupus familiaris
F	92.0	%	Homo sapiens
F	100.0	%	Homo sapiens
Fu	0.04	-	Rattus norvegicus
Fu	0.113	-	Homo sapiens
Fu	0.134	-	Macaca fascicularis
Fu	0.134	-	Canis lupus familiaris
Fu	0.082	-	Cavia porcellus
Fu	0.1	-	Mus musculus
Fu	0.07	-	Rattus norvegicus
Fu	0.111	-	Rattus norvegicus
T1/2	1.275	hr	Rattus norvegicus
T1/2	1.222	hr	Rattus norvegicus
T1/2	70.0	hr	Homo sapiens
T1/2	1.298	hr	Rattus norvegicus
T1/2	1.21	hr	Rattus norvegicus
T1/2	1.6	hr	Rattus norvegicus
T1/2	1.317	hr	Rattus norvegicus
T1/2	1.26	hr	Rattus norvegicus
T1/2	2.417	hr	Rattus norvegicus
T1/2	0.7667	hr	Mus musculus
T1/2	0.2133	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Acetylcholinesterase	IC50	=	1.7	nM	8.77	In vitro inhibitory effect on rat Acetylcholinesterase	7636858
Acetylcholinesterase	IC50	=	2.0	nM	8.7	Inhibition of acetylcholinesterase (unknown origin)	23199476
Acetylcholinesterase	IC50	=	2.0	nM	8.7	Inhibition of rat cortex homogenate acetylcholinesterase using acetylthiocholine...	33570950
Acetylcholinesterase	IC50	=	2.33	nM	8.63	Inhibition of acetylcholinesterase (AChE) of human red blood cell (type XIII) by...	-
Acetylcholinesterase	Ki	=	2.9	nM	8.54	Dissociation constant for inhibition of fetal bovine serum Acetylcholinesterase	15771436
Acetylcholinesterase	Ki	=	2.9	nM	8.54	Inhibition of fetal Bovine serum AChE	12502352
Acetylcholinesterase	IC50	=	3.9	nM	8.41	Inhibition of human erythrocyte AChE using acetylthiocholine iodide as substrate...	38516603
Acetylcholinesterase	IC50	=	4.0	nM	8.4	Inhibition of AChE (unknown origin) incubated for 30 mins by Ellman's method	35276424
Acetylcholinesterase	IC50	=	4.2	nM	8.38	Inhibition of bovine acetylcholinesterase using acetylcholine iodide as substrat...	23199476
Acetylcholinesterase	Ki	=	4.24	nM	8.37	Inhibition of electric eel AChE pre-incubated for 3 mins before acetylthiocholin...	25969170
Cholinesterase	IC50	=	4.6	nM	8.34	Inhibition of equine serum BuChE using S-butyrylthiocholine iodide as substrate ...	28797883
Acetylcholinesterase	IC50	=	5.0	nM	8.3	Inhibition of human recombinant AChE expressed in HEK293 cells using acetylthioc...	33340937
Acetylcholinesterase	IC50	=	5.0	nM	8.3	Inhibition of AChE in rat cortex homogenates using acetylthiocholine iodide as s...	22019465
Choline O-acetyltransferase	IC50	=	5.3	nM	8.28	In vitro inhibitory activity against acetylcholinesterase	1738151
Acetylcholinesterase	IC50	=	5.4	nM	8.27	Inhibition of AChE in mouse cerebral cortex using acetylthiocholine iodide as su...	35339839
Acetylcholinesterase	IC50	=	5.59	nM	8.25	Inhibition of recombinant human AChE using acetylthiocholine iodide as substrate...	31669851
Acetylcholinesterase	IC50	=	5.7	nM	8.24	Inhibition of human acetylcholinesterase	30744931
Acetylcholinesterase	IC50	=	5.7	nM	8.24	Inhibition of recombinant human AChE using acetylthiocholine iodide as substrate...	29335209
Acetylcholinesterase	IC50	=	5.7	nM	8.24	Inhibitory concentration in vitro and ex vivo for anti-AChE activity in rat brai...	-
Acetylcholinesterase	IC50	=	5.7	nM	8.24	Inhibition of recombinant human AChE using acetylthiocholine iodide as substrate...	30765302

Literature References

PubMed	DOI	Target Context	# Activities
26473791	10.1021/acs.jmedchem.5b01222	Rattus norvegicus	23
38663285	10.1016/j.ejmech.2024.116409	Rattus norvegicus	19
37678141	10.1016/j.ejmech.2023.115766	Rattus norvegicus	17
23810675	10.1016/j.bmc.2013.06.003	Rattus norvegicus	15
36306540	10.1016/j.ejmech.2022.114825	Mus musculus	14
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
36257284	10.1016/j.ejmech.2022.114841	ADMET	13
38190615	10.1021/acs.jmedchem.3c02148	ADMET	12
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
24581918	10.1016/j.bmcl.2014.02.008	NON-PROTEIN TARGET	10
36921526	10.1016/j.ejmech.2023.115253	Danio rerio	8
34198150	10.1016/j.ejmech.2021.113663	Acetylcholinesterase	8
31288978	10.1016/j.bmc.2019.07.001	Mus musculus	8
38081625	10.1021/acs.jnatprod.3c00894	Mus musculus	8
30784883	10.1016/j.ejmech.2019.02.030	Rattus norvegicus	8
33570950	10.1021/acs.jmedchem.0c01863	Acetylcholinesterase	8
30503937	10.1016/j.ejmech.2018.11.049	Mus musculus	8
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
35339839	10.1016/j.ejmech.2022.114305	SH-SY5Y	8
27783974	10.1016/j.ejmech.2016.10.042	Acetylcholinesterase	8

Data from ChEMBL 36 via Core Engine