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Compound Detail

CHEMBL807

MEMANTINE
💊 Approved Drug
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💊 Approved Drug
CC12CC3CC(C)(C1)CC(N)(C3)C2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL807
Name MEMANTINE
Phase Approved
Structure Type MOL
InChI Key BUGYDGFZZOZRHP-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

D-145 DRG-0267 Memantina Memantine NSC-757843
15
Targets
59
Activities
3
Assay Types
2
PK Parameters
20
Publications
5
Known Names
20
Indications

Molecular Properties

179.3
MW (Da)
2.69
ALogP
1
HBA
1
HBD
26.0
PSA (Ų)
0.61
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2002
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -mantine
USAN Year 2003

Extended Properties

Molecular Formula C12H21N
MW 179.31
Aromatic Rings 0
Heavy Atoms 13
NP-Likeness 0.53

Indications

Dementia Alzheimer Disease Anxiety Bipolar Disorder Child Development Disorders, Pervasive Cognitive Dysfunction Cognitive Dysfunction Depressive Disorder Fibromyalgia Glaucoma, Open-Angle Ischemic Stroke Migraine Disorders Multiple Sclerosis Obsessive-Compulsive Disorder Pain Parkinson Disease Schizophrenia Substance-Related Disorders Substance-Related Disorders Tension-Type Headache

ATC Classification

N06DX01
memantine
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOANALEPTICS

Activity Summary

IC50 44 meas. best 9.02
Ki 13 meas. best 6.37
EC50 2 meas. best 5.61

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Glutamate NMDA receptor; GRIN1/GRIN2A
CHEMBL1907604
 IC50 9.02 6.0333 0.9 6
Acetylcholinesterase
CHEMBL220
 IC50 8.31 7.21 4.9 2
Unchecked
CHEMBL612545
 IC50 6.65 5.7238 222.0 13
Unchecked
CHEMBL612545
 Ki 6.37 5.9375 429.0 8
Glutamate [NMDA] receptor
CHEMBL2094124
 Ki 6.27 6.1533 540.0 3
Glutamate receptor ionotropic, NMDA 2C
CHEMBL401
 Ki 6.16 6.16 700.0 1
SH-SY5Y
CHEMBL614910
 IC50 6.14 6.14 718.0 1
Glutamate NMDA receptor; GRIN1/GRIN2B
CHEMBL1907603
 Ki 6.0 6.0 1000.0 1
Glutamate NMDA receptor; Grin1/Grin2a
CHEMBL2096680
 IC50 6.0 5.79 1000.0 2
Glutamate NMDA receptor; GRIN1/GRIN2B
CHEMBL1907603
 IC50 5.99 5.3875 1020.0 4
Glutamate NMDA receptor
CHEMBL1907608
 IC50 5.96 5.236 1090.0 10
Cerebellar granule neurone
CHEMBL614452
 EC50 5.61 5.61 2480.0 1
Glutamate receptor ionotropic, NMDA 1
CHEMBL330
 EC50 5.57 5.57 2720.0 1
Glutamate NMDA receptor; Grin1/Grin2b
CHEMBL2096666
 IC50 5.25 5.25 5570.0 1
Nicotinic acetylcholine receptor alpha6/alpha3/beta4
CHEMBL3137276
 IC50 5.22 5.22 6000.0 1
Trypanosoma brucei
CHEMBL612849
 IC50 4.86 4.86 13750.0 2
Solute carrier family 22 member 1
CHEMBL5685
 IC50 4.57 4.57 27200.0 1

Pharmacokinetic Data

Parameter Value Units Species
F 100.0 % Homo sapiens
T1/2 60.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Glutamate NMDA receptor; GRIN1/GRIN2A IC50 = 0.95 nM 9.02 Antagonist activity at recombinant GluN1/GluN2A receptor (unknown origin) expres... 23692871
Acetylcholinesterase IC50 = 4.9 nM 8.31 Inhibition of recombinant human AChE expressed in HEK293 cells by Ellman's metho... 34391122
Unchecked IC50 = 222.0 nM 6.65 Antagonist activity at GluN1-1a/GluN2C (unknown origin) expressed in xenopus lae... 37515920
Unchecked IC50 = 318.0 nM 6.5 Antagonist activity at GluN1-1b/GluN2C (unknown origin) expressed in xenopus lae... 37515920
Unchecked IC50 = 367.0 nM 6.43 Antagonist activity at GluN1-1a/GluN2D (unknown origin) expressed in xenopus lae... 37515920
Unchecked Ki = 429.0 nM 6.37 Displacement of [3H]-(+)-MK-801 from PCP binding site of NMDA receptor in pig br... 23013229
Unchecked Ki = 540.0 nM 6.27 Displacement of [3H]MK801 from NMDA receptor in human brain by radioligand bindi... 32717484
Glutamate [NMDA] receptor Ki = 540.0 nM 6.27 Binding affinity to NMDAR (unknown origin) 32248004
Glutamate [NMDA] receptor Ki = 540.0 nM 6.27 The compound was tested for its ability to block PCP N-methyl-D-aspartate glutam... 9464369
Unchecked IC50 = 592.0 nM 6.23 Antagonist activity at GluN1-1b/GluN2D (unknown origin) expressed in xenopus lae... 37515920
Glutamate receptor ionotropic, NMDA 2C Ki = 700.0 nM 6.16 Compound with the N-methyl-D-aspartate glutamate receptor blocking activity 10229619
SH-SY5Y IC50 = 718.0 nM 6.14 Neuroprotective activity in human SH-SY5Y cells assessed as protection against N... 23033965
Unchecked Ki = 740.0 nM 6.13 Displacement of [3H]-(+)-MK-801 from PCP binding site of NMDA receptor in pig br... 29254894
Acetylcholinesterase IC50 = 780.0 nM 6.11 Inhibition of AChE (unknown origin) 37515920
Unchecked IC50 = 778.0 nM 6.11 Antagonist activity at GluN1-1a/GluN2B (unknown origin) expressed in xenopus lae... 37515920
Glutamate NMDA receptor; GRIN1/GRIN2A IC50 = 911.0 nM 6.04 Antagonist activity at recombinant NR1/NR2A receptor expressed in Xenopus laevis... 17624774
Glutamate NMDA receptor; GRIN1/GRIN2B Ki = 1000.0 nM 6.0 Inhibition of recombinant GluN1/GluN2B receptor (unknown origin) expressed in HE... 31351393
Glutamate NMDA receptor; Grin1/Grin2a IC50 = 1000.0 nM 6.0 Inhibition of eGFP-tagged rat GluN1-1a/GluN2A transfected in human tsA201 cells ... 35453065
Glutamate NMDA receptor; GRIN1/GRIN2B IC50 = 1020.0 nM 5.99 Antagonist activity at recombinant NR1/NR2B receptor expressed in Xenopus laevis... 17624774
Glutamate NMDA receptor IC50 = 1090.0 nM 5.96 Displacement of [3H]MK-801 from NMDA receptor in Wistar rat brain membranes by s... 26296478

Literature References

PubMed DOI Target Context # Activities
- 10.5281/zenodo.13943903 ADMET 89
31158845 10.1038/s41586-019-1291-3 ADMET 60
34825189 10.1039/D1MD00177A SH-SY5Y 19
26296478 10.1016/j.bmcl.2015.08.017 Glutamate NMDA receptor 15
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
24581918 10.1016/j.bmcl.2014.02.008 NON-PROTEIN TARGET 11
7086822 10.1021/jm00343a010 Mus musculus 9
35729801 10.1021/acs.jmedchem.2c00399 HT-22 8
37515920 10.1016/j.ejmech.2023.115670 Unchecked 8
35453065 10.1016/j.ejmech.2022.114354 Glutamate NMDA receptor; Grin1/Grin2a 8
30108699 10.1039/C6MD00509H Cortical neurone 8
35453065 10.1016/j.ejmech.2022.114354 Unchecked 4
20361801 10.1021/jm1000024 Glutamate NMDA receptor; GRIN1/GRIN2A 4
36716640 10.1016/j.ejmech.2023.115163 SH-SY5Y 4
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 3
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
37468498 10.1038/s41467-023-40064-9 Histamine H1 receptor 3
23098038 10.1021/jm301055g NON-PROTEIN TARGET 3
31103902 10.1016/j.ejmech.2019.05.020 ADMET 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 3

Data from ChEMBL 36 via Core Engine