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Compound Detail

CHEMBL1555

GALANTAMINE HYDROBROMIDE
💊 Approved Drug
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💊 Approved Drug
Br.COc1ccc2c3c1O[C@H]1C[C@@H](O)C=C[C@@]31CCN(C)C2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1555
Name GALANTAMINE HYDROBROMIDE
Phase Approved
Structure Type MOL
InChI Key QORVDGQLPPAFRS-XPSHAMGMSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL659
Active Moiety CHEMBL659

Known Names

(-)-galantamine hydrobromide Galantamine hydrobromide Galanthamine hydrobromide Jilkon hydrobromide Lycoremine hydrobromide Nivalin Nivaline Razadyne Razadyne er Tamilin
6
Targets
32
Activities
3
Assay Types
23
PK Parameters
20
Publications
10
Known Names
8
Indications
1
Mechanisms

Molecular Properties

287.4
MW (Da)
1.85
ALogP
4
HBA
1
HBD
41.9
PSA (Ų)
0.80
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2001
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral
USAN Year 2000

Extended Properties

Molecular Formula C17H22BrNO3
MW 368.27
Aromatic Rings 1
Heavy Atoms 21
NP-Likeness 2.11

Mechanism of Action

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

Indications

Alzheimer Disease Dementia Brain Diseases Cognitive Dysfunction Dementia, Vascular Mental Disorders Schizophrenia Frontotemporal Dementia

Activity Summary

IC50 18 meas. best 6.66
Ki 13 meas. best 6.43
EC50 1 meas. best 4.96

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Acetylcholinesterase
CHEMBL4078
 IC50 6.66 6.0583 220.0 6
Acetylcholinesterase
CHEMBL4078
 Ki 6.43 6.3289 370.0 9
Acetylcholinesterase
CHEMBL4780
 IC50 5.97 5.97 1069.0 2
Cholinesterase
CHEMBL5763
 IC50 5.82 5.035 1520.0 6
Cholinesterase
CHEMBL5763
 Ki 5.68 5.2775 2070.0 4
Acetylcholinesterase
CHEMBL220
 IC50 5.58 5.5 2600.0 3
Unchecked
CHEMBL612545
 EC50 4.96 4.96 11054.0 1
Butyrylcholinesterase
CHEMBL5077
 IC50 4.9 4.9 12600.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 991.39 ng.hr.mL-1 Rattus norvegicus
AUC 830.47 ng.hr.mL-1 Rattus norvegicus
CL 5.667 mL.min-1.kg-1 Homo sapiens
CL 34.0 mL.min-1.kg-1 Rattus norvegicus
CL 41.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 1330.0 nM Rattus norvegicus
Cmax 910.0 nM Rattus norvegicus
Cmax 890.0 nM Rattus norvegicus
Cmax 590.0 nM Rattus norvegicus
F 85.0 % Homo sapiens
F 67.0 % Rattus norvegicus
F 83.0 % Rattus norvegicus
MRT 1.5 hr Rattus norvegicus
MRT 2.0 hr Rattus norvegicus
T1/2 5.0 hr Homo sapiens
T1/2 1.2 hr Rattus norvegicus
T1/2 1.9 hr Rattus norvegicus
Tmax 1.0 hr Homo sapiens
Tmax 0.5 hr Rattus norvegicus
Tmax 0.5 hr Rattus norvegicus
Vd 2.9 L.kg-1 Homo sapiens
Vd 2.9 L.kg-1 Rattus norvegicus
Vd 5.0 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Acetylcholinesterase IC50 = 220.0 nM 6.66 Inhibition of electric eel AChE using acetylthiocholine iodide as substrate prei... 36047675
Acetylcholinesterase Ki = 370.0 nM 6.43 Competitive inhibition of electric eel AChE using acetylthiocholine iodide as su... 30220607
Acetylcholinesterase Ki = 370.0 nM 6.43 Competitive inhibition of electric eel AChE assessed as inhibition constant for ... 28802122
Acetylcholinesterase Ki = 400.0 nM 6.4 Competitive inhibition of electric eel AChE using acetylthiocholine iodide as su... 27936444
Acetylcholinesterase Ki = 450.0 nM 6.35 Inhibition of Electrophorus electricus AChE by Ellman's method 17574306
Acetylcholinesterase Ki = 540.0 nM 6.27 Inhibition of Electrophorus electricus AChE using acetylthiocholine iodide as su... 26383128
Acetylcholinesterase Ki = 540.0 nM 6.27 Inhibition of Electrophorus electricus acetylcholinesterase using acetylthiochol... 25980913
Acetylcholinesterase Ki = 540.0 nM 6.27 Inhibition of Electrophorus electricus AChE using acetylthiocholine iodide as su... 24853320
Acetylcholinesterase Ki = 540.0 nM 6.27 Competitive inhibition of Electrophorus electricus acetylcholinesterase in prese... 27689726
Acetylcholinesterase Ki = 540.0 nM 6.27 Mixed inhibition of electric eel AChE using acetylcholine iodide as substrate pr... 31158743
Acetylcholinesterase IC50 = 550.0 nM 6.26 Inhibition of Electrophorus electricus AChE by Ellman's method 17574306
Acetylcholinesterase IC50 = 670.0 nM 6.17 Inhibition of electric eel AChE after 15 mins by Ellman's method 20452769
Acetylcholinesterase IC50 = 1020.0 nM 5.99 Inhibition of Electrophorus electricus (electric eel) AChE using acetylthiocholi... -
Acetylcholinesterase IC50 = 1070.0 nM 5.97 Inhibition of Torpedo californica AChE using ATCI substrate incubated for 30 min... 26260334
Acetylcholinesterase IC50 = 1069.05 nM 5.97 Inhibition of Torpedo californica AChE using ATCI substrate incubated for 30 min... 26260334
Acetylcholinesterase IC50 = 1230.0 nM 5.91 Inhibition of electric eel AChE using acetylthiocholine iodide as substrate prei... 30220607
Cholinesterase IC50 = 1520.0 nM 5.82 Inhibition of horse serum BChE after 15 mins by Ellman's method 20452769
Cholinesterase Ki = 2070.0 nM 5.68 Competitive inhibition of equine serum butyrylcholinesterase in presence of vary... 27689726
Acetylcholinesterase IC50 = 2600.0 nM 5.58 Inhibition of human AChE using acetylthiocholine iodide as substrate preincubate... 27951490
Acetylcholinesterase IC50 = 3200.0 nM 5.5 Inhibition of human AChE by Ellman's assay 21873056

Literature References

PubMed DOI Target Context # Activities
21148081 10.1124/dmd.110.035964 Rattus norvegicus 24
21148081 10.1124/dmd.110.035964 Blood 6
21148081 10.1124/dmd.110.035964 Homo sapiens 5
21148081 10.1124/dmd.110.035964 ADMET 3
30220607 10.1016/j.bmcl.2018.09.013 Acetylcholinesterase 3
- 10.1007/s00044-013-0493-8 Acetylcholinesterase 2
28802122 10.1016/j.ejmech.2017.07.081 Acetylcholinesterase 2
31158743 10.1016/j.ejmech.2019.05.059 Acetylcholinesterase 2
21148081 10.1124/dmd.110.035964 Unchecked 2
26260334 10.1016/j.bmc.2015.07.058 Acetylcholinesterase 2
17574306 10.1016/j.ejmech.2007.03.018 Acetylcholinesterase 2
21873056 10.1016/j.bmcl.2011.07.091 Acetylcholinesterase 2
21873056 10.1016/j.bmcl.2011.07.091 Unchecked 2
21429752 10.1016/j.bmc.2011.02.030 Unchecked 1
21429752 10.1016/j.bmc.2011.02.030 SH-SY5Y 1
36047675 10.1021/acs.jnatprod.2c00395 Acetylcholinesterase 1
20452769 10.1016/j.bmcl.2010.04.059 Unchecked 1
20452769 10.1016/j.bmcl.2010.04.059 Acetylcholinesterase 1
17067156 10.1021/np0680174 Cholinesterase 1
17574306 10.1016/j.ejmech.2007.03.018 Unchecked 1

Data from ChEMBL 36 via Core Engine