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Compound Detail

CHEMBL636

RIVASTIGMINE
💊 Approved Drug
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💊 Approved Drug
CCN(C)C(=O)Oc1cccc([C@H](C)N(C)C)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL636
Name RIVASTIGMINE
Phase Approved
Structure Type MOL
InChI Key XSVMFMHYUFZWBK-NSHDSACASA-N
Therapeutic ✓ Yes

Known Names

ENA-713 ENA-713D Exelon ONO-2540 Rivastigmina Rivastigmine Rivastigmine 3m health care ltd SDZ-212-713 SDZ-212713 SDZ-ENA-713
14
Targets
194
Activities
3
Assay Types
21
PK Parameters
20
Publications
10
Known Names
18
Indications
1
Mechanisms

Molecular Properties

250.3
MW (Da)
2.76
ALogP
3
HBA
0
HBD
32.8
PSA (Ų)
0.82
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1998
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral Topical

Flags

Natural Product
USAN Stem -stigmine
USAN Year 1997

Extended Properties

Molecular Formula C14H22N2O2
MW 250.34
Aromatic Rings 1
Heavy Atoms 18
NP-Likeness -0.98

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Cholinesterases; ACHE & BCHE inhibitor INHIBITOR Cholinesterases; ACHE & BCHE ✓ ✓

Indications

Alzheimer Disease Dementia Parkinson Disease Anxiety Brain Injuries Cognitive Dysfunction Delirium Dementia, Vascular Depressive Disorder Neurobehavioral Manifestations Schizophrenia Supranuclear Palsy, Progressive Amphetamine-Related Disorders Central Nervous System Diseases Cocaine-Related Disorders Down Syndrome Substance-Related Disorders Substance-Related Disorders

ATC Classification

N06DA03
rivastigmine
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOANALEPTICS

Activity Summary

IC50 191 meas. best 7.84
Ki 2 meas. best 6.16
Kd 1 meas. best 5.94

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cholinesterase
CHEMBL1914
 IC50 7.84 6.3615 14.3 47
Acetylcholinesterase
CHEMBL220
 IC50 7.43 5.6225 37.0 53
Cholinesterase
CHEMBL5763
 IC50 7.28 5.8016 52.0 25
Cholinesterase
CHEMBL2528
 IC50 7.24 6.52 58.0 2
Butyrylcholinesterase
CHEMBL5077
 IC50 6.8 6.44 160.0 2
Butyrylcholinesterase
CHEMBL3403
 IC50 6.46 5.68 350.0 8
Acetylcholinesterase
CHEMBL4768
 IC50 6.21 6.21 620.0 1
Acetylcholinesterase
CHEMBL220
 Ki 6.16 6.16 700.0 1
Acetylcholinesterase
CHEMBL3198
 IC50 5.96 5.2925 1110.0 4
Cholinesterase
CHEMBL5763
 Kd 5.94 5.94 1150.0 1
Unchecked
CHEMBL612545
 IC50 5.88 5.33 1320.0 5
Acetylcholinesterase
CHEMBL3199
 IC50 5.74 5.191 1820.0 10
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.54 5.54 2860.0 1
Acetylcholinesterase
CHEMBL4078
 IC50 5.47 5.0145 3400.0 29
Acetylcholinesterase
CHEMBL3198
 Ki 5.25 5.25 5680.0 1
Cholinesterase
CHEMBL4630814
 IC50 5.2 5.2 6270.0 1
Acetylcholine receptor subunit epsilon
CHEMBL4961
 IC50 5.05 5.05 9000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 12.0 mL.min-1.kg-1 Homo sapiens
CL 12.0 mL.min-1.kg-1 Homo sapiens
CL-renal 2.1 L/hr Homo sapiens
Fu 0.6 - Homo sapiens
Fu 0.6 - Homo sapiens
Fu 0.345 - Homo sapiens
Fu 0.316 - Macaca fascicularis
Fu 0.487 - Canis lupus familiaris
Fu 0.389 - Cavia porcellus
Fu 0.341 - Mus musculus
Fu 0.241 - Rattus norvegicus
Fu 0.338 - Rattus norvegicus
MRT 1.9 hr Homo sapiens
PPB 40.0 % Homo sapiens
Ratio AUC(inf) 0.7 - Homo sapiens
Ratio AUC(inf) 3.5 - Homo sapiens
T1/2 1.4 hr Homo sapiens
T1/2 24.0 hr Homo sapiens
Tmax 8.0 hr Homo sapiens
Tmax 1.4 hr Homo sapiens
Vd 1.8 L.kg-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cholinesterase IC50 = 14.3 nM 7.84 Inhibition of human serum BuChE using butyrylthiocholine iodide as substrate pre... 33979775
Cholinesterase IC50 = 30.1 nM 7.52 Inhibition of human recombinant butyrylcholinesterase 17850125
Cholinesterase IC50 = 30.0 nM 7.52 Inhibition of BChE (unknown origin) 30031971
Cholinesterase IC50 = 30.0 nM 7.52 Inhibition of recombinant human BChE by Ellman method 25226236
Cholinesterase IC50 = 37.0 nM 7.43 Ex vivo inhibition of human plasma Butyrylcholinesterase. 12166941
Cholinesterase IC50 = 37.0 nM 7.43 Inhibitory concentration against human plasma Butyrylcholinesterase 15715468
Cholinesterase IC50 = 37.0 nM 7.43 Anticholinesterase activity against human plasma BChE 16570913
Cholinesterase IC50 = 37.0 nM 7.43 Inhibition of BuChE 20067290
Acetylcholinesterase IC50 = 37.0 nM 7.43 Inhibition of human erythrocytes BChE 21459491
Acetylcholinesterase IC50 = 37.0 nM 7.43 Inhibition of human plasma BChE 21459491
Cholinesterase IC50 = 37.0 nM 7.43 Inhibition of human BuChE using S-butyrylthiocholine as substrate preincubated f... 33310288
Cholinesterase IC50 = 49.0 nM 7.31 Inhibition of BChE 21216144
Cholinesterase IC50 = 52.0 nM 7.28 Inhibition of equine serum BuChE using butyrylthiocholine iodide as substrate pr... 37224761
Acetylcholinesterase IC50 = 54.0 nM 7.27 Inhibition of AChE-induced amyloid beta aggregation 21216144
Acetylcholinesterase IC50 = 54.0 nM 7.27 Inhibition of AChE (unknown origin) 26159481
Cholinesterase IC50 = 58.0 nM 7.24 Inhibition of equine serum BuChE using butyrylthiocholine iodide as substrate pr... 34371367
Cholinesterase IC50 = 58.0 nM 7.24 Inhibition of mouse plasma BuChE using S-butyrylacetylthiocholine iodide as subs... 30822710
Acetylcholinesterase IC50 = 60.0 nM 7.22 Inhibition of human recombinant AChE using acetylthiocholine iodide as substrate... 33979775
Cholinesterase IC50 = 105.3 nM 6.98 Inhibition of human serum BuChE using butyrylthiocholine iodide as substrate inc... 38157596
Butyrylcholinesterase IC50 = 160.0 nM 6.8 Inhibition of equine BuChE after 120 mins by Ellman's method 23151013

Literature References

PubMed DOI Target Context # Activities
- 10.5281/zenodo.13943903 ADMET 89
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
24581918 10.1016/j.bmcl.2014.02.008 NON-PROTEIN TARGET 10
27448914 10.1016/j.ejmech.2016.06.046 NON-PROTEIN TARGET 9
35065231 10.1016/j.bmcl.2022.128574 Acetylcholinesterase 7
31158742 10.1016/j.ejmech.2019.05.051 Danio rerio 6
31865014 10.1016/j.ejmech.2019.111958 Cholinesterase 6
32240904 10.1016/j.ejmech.2020.112265 Cholinesterase 6
27448914 10.1016/j.ejmech.2016.06.046 Mus musculus 6
31865014 10.1016/j.ejmech.2019.111958 Acetylcholinesterase 6
34371367 10.1016/j.ejmech.2021.113735 Cholinesterase 6
19423342 10.1016/j.bmcl.2009.04.089 Rattus norvegicus 6
21474681 10.1124/dmd.111.038778 Brain 5
19520578 10.1016/j.bmc.2009.05.057 Cholinesterase 5
27856236 10.1016/j.bmc.2016.11.002 NON-PROTEIN TARGET 5
31585237 10.1016/j.ejmech.2019.111745 BV-2 4
12431053 10.1021/jm020120c ADMET 4
18426954 10.1124/dmd.108.020479 ADMET 4
31229875 10.1016/j.ejmech.2019.06.026 Cholinesterase 4
18479118 10.1021/jm701253t Acetylcholinesterase 4

Data from ChEMBL 36 via Core Engine