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Details

Stereochemistry ACHIRAL
Molecular Formula C12H21N
Molecular Weight 179.3018
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MEMANTINE

SMILES

CC12CC3CC(C)(C1)CC(N)(C3)C2

InChI

InChIKey=BUGYDGFZZOZRHP-UHFFFAOYSA-N
InChI=1S/C12H21N/c1-10-3-9-4-11(2,6-10)8-12(13,5-9)7-10/h9H,3-8,13H2,1-2H3

HIDE SMILES / InChI

Description

NAMENDA (marketed under the brands Namenda among others) is an N-methyl-D-aspartate (NMDA) receptor antagonist indicated for the treatment of moderate to severe dementia of the Alzheimer’s type. Persistent activation of central nervous system N-methyl-D-aspartate (NMDA) receptors by the excitatory amino acid glutamate has been hypothesized to contribute to the symptomatology of Alzheimer’s disease. Memantine is postulated to exert its therapeutic effect through its action as a low to moderate affinity uncompetitive (open-channel) NMDA receptor antagonist which binds preferentially to the NMDA receptor-operated cation channels. There is no evidence that memantine prevents or slows neurodegeneration in patients with Alzheimer’s disease. Memantine showed low to negligible affinity for GABA, benzodiazepine, dopamine, adrenergic, histamine and glycine receptors and for voltage-dependent Ca2+, Na+ or K+ channels. Memantine also showed antagonistic effects at the 5HT3 receptor with a potency similar to that for the NMDA receptor and blocked nicotinic acetylcholine receptors with one-sixth to one-tenth the potency. In vitro studies have shown that memantine does not affect the reversible inhibition of acetylcholinesterase by donepezil, galantamine, or tacrine.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

PubMed

PubMed

TitleDatePubMed
[Memantine and neurogenic bladder disorders within the bounds of spastic conditions].
1982
Methyl parathion acute toxicity: prophylaxis and therapy with memantine and atropine.
1990 May-Jun
Pharmacotoxic psychosis after memantine in Parkinson's disease.
1991 Oct 19
Inhibition by memantine of the development of persistent oral dyskinesias induced by long-term haloperidol treatment of rats.
1996 Oct
How to overcome resistance of influenza A viruses against adamantane derivatives.
1998 Feb
Low affinity channel blocking (uncompetitive) NMDA receptor antagonists as therapeutic agents--toward an understanding of their favorable tolerability.
2000
Prevention of cocaine-induced convulsions and lethality in mice: effectiveness of targeting different sites on the NMDA receptor complex.
2000 Jan 28
[A comparative study of the central H-cholinergic-blocking and NMDA-blocking actions of MK-801, memantin, amantadine, pyrilen and IEM-1754 in experiments on intact rats].
2000 Mar-Apr
NMDA antagonists inhibit the development of ethanol dependence in rats.
2001 Jan-Feb
Involvement of nitric oxide in myotoxicity produced by diisopropylphosphorofluoridate (DFP)-induced muscle hyperactivity.
2002 Dec
A double-blind, placebo-controlled multicentre study of memantine in mild to moderate vascular dementia (MMM500).
2002 Nov
Are neuronal nicotinic receptors a target for antiepileptic drug development? Studies in different seizure models in mice and rats.
2003 Apr 11
Memantine attenuates the increase in striatal preproenkephalin mRNA expression and development of haloperidol-induced persistent oral dyskinesias in rats.
2003 Dec 24
The neuropharmacological basis for the use of memantine in the treatment of Alzheimer's disease.
2003 Fall
The ability of new non-competitive glutamate receptor blockers to weaken motor disorders in animals.
2003 Mar
New platinum(IV) complex with adamantylamine ligand as a promising anti-cancer drug: comparison of in vitro cytotoxic potential towards A2780/cisR cisplatin-resistant cell line within homologous series of platinum(IV) complexes.
2004 Jun
Mechanisms intrinsic to 5-HT2B receptor-induced potentiation of NMDA receptor responses in frog motoneurones.
2004 Oct
Exacerbation of Lewy bodies dementia due to memantine.
2005 Dec
Effect of NMDA receptor antagonists on behavioral impairment induced by chronic treatment with dexamethasone.
2005 Jan-Feb
Memantine alleviates toxicity induced by dichlorvos in rats.
2005 Mar
Development of subtle psychotic symptoms with memantine: a case report.
2005 May
Effect of BD 1047, a sigma1 receptor antagonist, in the animal models predictive of antipsychotic activity.
2006 Sep-Oct
Exacerbation of myoclonus by memantine in a patient with Alzheimer disease.
2007 Aug
A retrospective study of memantine in children and adolescents with pervasive developmental disorders.
2007 Mar
Memantine as adjunctive therapy in children diagnosed with autistic spectrum disorders: an observation of initial clinical response and maintenance tolerability.
2007 May
Visual hallucinations and agitation in Alzheimer's disease due to memantine: report of three cases.
2007 May
[Therapy of Alzheimer's disease: current status and future development].
2008
Memantine-induced hepatitis with cholestasis in a very elderly patient.
2008 Apr 15
Effects of memantine on neuronal structure and conditioned fear in the Tg2576 mouse model of Alzheimer's disease.
2008 Dec
Memantine and NMDA antagonism for chronic migraine: a potentially novel therapeutic approach?
2008 Feb
Methylmercury increases N-methyl-D-aspartate receptors on human SH-SY 5Y neuroblastoma cells leading to neurotoxicity.
2008 Jul 30
Memantine-induced myoclonus and delirium exacerbated by trimethoprim.
2008 Mar
Memantine for agitation/aggression and psychosis in moderately severe to severe Alzheimer's disease: a pooled analysis of 3 studies.
2008 Mar
The attenuating effect of memantine on staurosporine-, salsolinol- and doxorubicin-induced apoptosis in human neuroblastoma SH-SY5Y cells.
2008 Mar-Apr
Profound pain reduction after induction of memantine treatment in two patients with severe phantom limb pain.
2008 Oct
Does memantine induce bradycardia? A study in the French PharmacoVigilance Database.
2008 Sep
Memanti-nium chloride 0.1-hydrate.
2009 Aug 19
Memantine dosing in patients with dementia.
2009 Feb
Role of N-methyl-D-aspartate receptors in polychlorinated biphenyl mediated neurotoxicity.
2009 Jan 10
Characteristic effects of anti-dementia drugs on rat sleep patterns.
2009 Mar
Protection of DFP-induced oxidative damage and neurodegeneration by antioxidants and NMDA receptor antagonist.
2009 Oct 15
[Effects of electroacupuncture on expression of Abeta positive cells of the hippocampus and SOD activity in rats with streptozocin-Alzheimer's disease].
2010 Dec
NMDA antagonist memantine improves levodopa-induced dyskinesias and "on-off" phenomena in Parkinson's disease.
2010 Mar 15
Memantine ameliorates scopolamine-induced amnesia in chicks trained on taste-avoidance learning.
2010 May
Inhibition of apoptosis in human retinal pigment epithelial cells treated with benzo(e)pyrene, a toxic component of cigarette smoke.
2010 May
Protective effects of memantine and epicatechin on catechol-induced toxicity on Müller cells in vitro.
2010 May 27
Memantine prevents aluminum-induced cognitive deficit in rats.
2011 Nov 20
The role of memantine in the treatment of psychiatric disorders other than the dementias: a review of current preclinical and clinical evidence.
2012 Aug 1
Memantine in patients with moderate to severe Alzheimer's disease: meta-analyses using realistic definitions of response.
2014
Glial activation and post-synaptic neurotoxicity: the key events in Streptozotocin (ICV) induced memory impairment in rats.
2014 Feb
Patents

Sample Use Guides

In Vivo Use Guide
Initial dose is 5 mg once daily. Increase dose in 5 mg increments to a maintenance dose of 10 mg twice daily. A minimum of 1 week of treatment with the previous dose should be observed before increasing the dose.
Route of Administration: Oral
In Vitro Use Guide
Neuronal SK-N-SH cells were treated with 10 uM memantine and was measured levels of secreted total A beta precursor protein APP (sAPP), APP alpha isoform and A beta((1-40)) in a time dependent manner for up to 24h. Memantine significantly decreased the levels of the secreted form of sAPP, sAPP alpha and A beta((1-40)) compared to vehicle treated cells.
Name Type Language
MEMANTINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
MEMANTINE [WHO-DD]
Common Name English
3,5-DIMETHYL-1-ADAMANTANAMINE
Systematic Name English
D-145
Code English
MEMANTINE [VANDF]
Common Name English
MEMANTINE [MI]
Common Name English
TRICYCLO(3.3.1.1(SUP 3,7))DECAN-1-AMINE, 3,5-DIMETHYL-
Common Name English
1-AMINO-3,5-DIMETHYLADAMANTANE
Systematic Name English
NEMDATINE
Brand Name English
MEMANTINE [INN]
Common Name English
DRG-0267
Code English
3,5-DIMETHYLTRICYCLO(3.3.1.1(SUP 3,7))DECAN-1-AMINE
Systematic Name English
MEMANTINE [HSDB]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1509
Created by admin on Tue Oct 22 00:25:02 UTC 2019 , Edited by admin on Tue Oct 22 00:25:02 UTC 2019
NDF-RT N0000020015
Created by admin on Tue Oct 22 00:25:02 UTC 2019 , Edited by admin on Tue Oct 22 00:25:02 UTC 2019
NCI_THESAURUS C38149
Created by admin on Tue Oct 22 00:25:02 UTC 2019 , Edited by admin on Tue Oct 22 00:25:02 UTC 2019
WHO-ATC N06DX01
Created by admin on Tue Oct 22 00:25:02 UTC 2019 , Edited by admin on Tue Oct 22 00:25:02 UTC 2019
WHO-ATC N06DA52
Created by admin on Tue Oct 22 00:25:02 UTC 2019 , Edited by admin on Tue Oct 22 00:25:02 UTC 2019
WHO-VATC QN06DA52
Created by admin on Tue Oct 22 00:25:02 UTC 2019 , Edited by admin on Tue Oct 22 00:25:02 UTC 2019
NDF-RT N0000175745
Created by admin on Tue Oct 22 00:25:02 UTC 2019 , Edited by admin on Tue Oct 22 00:25:02 UTC 2019
WHO-VATC QN06DX01
Created by admin on Tue Oct 22 00:25:02 UTC 2019 , Edited by admin on Tue Oct 22 00:25:02 UTC 2019
LIVERTOX 597
Created by admin on Tue Oct 22 00:25:02 UTC 2019 , Edited by admin on Tue Oct 22 00:25:02 UTC 2019
WHO-ATC N06DA53
Created by admin on Tue Oct 22 00:25:02 UTC 2019 , Edited by admin on Tue Oct 22 00:25:02 UTC 2019
NDF-RT N0000020015
Created by admin on Tue Oct 22 00:25:02 UTC 2019 , Edited by admin on Tue Oct 22 00:25:02 UTC 2019
EMA ASSESSMENT REPORTS NEMDATINE (AUTHORIZED: ALZHEIMER DISEASE)
Created by admin on Tue Oct 22 00:25:02 UTC 2019 , Edited by admin on Tue Oct 22 00:25:02 UTC 2019
Code System Code Type Description
RXCUI
6719
Created by admin on Tue Oct 22 00:25:02 UTC 2019 , Edited by admin on Tue Oct 22 00:25:02 UTC 2019
PRIMARY RxNorm
INN
3952
Created by admin on Tue Oct 22 00:25:02 UTC 2019 , Edited by admin on Tue Oct 22 00:25:02 UTC 2019
PRIMARY
CAS
19982-08-2
Created by admin on Tue Oct 22 00:25:02 UTC 2019 , Edited by admin on Tue Oct 22 00:25:02 UTC 2019
PRIMARY
EPA CompTox
19982-08-2
Created by admin on Tue Oct 22 00:25:02 UTC 2019 , Edited by admin on Tue Oct 22 00:25:02 UTC 2019
PRIMARY
HSDB
19982-08-2
Created by admin on Tue Oct 22 00:25:02 UTC 2019 , Edited by admin on Tue Oct 22 00:25:02 UTC 2019
PRIMARY
IUPHAR
4253
Created by admin on Tue Oct 22 00:25:02 UTC 2019 , Edited by admin on Tue Oct 22 00:25:02 UTC 2019
PRIMARY
NCI_THESAURUS
C73269
Created by admin on Tue Oct 22 00:25:02 UTC 2019 , Edited by admin on Tue Oct 22 00:25:02 UTC 2019
PRIMARY
CLINICAL_TRIALS.GOV
NCT03527472
Created by admin on Tue Oct 22 00:25:02 UTC 2019 , Edited by admin on Tue Oct 22 00:25:02 UTC 2019
PRIMARY Memantine for the Treatment of Cognitive Impairment in Systemic Lupus Erythematosus (ClearMEMory)
PUBCHEM
4054
Created by admin on Tue Oct 22 00:25:02 UTC 2019 , Edited by admin on Tue Oct 22 00:25:02 UTC 2019
PRIMARY
EVMPD
SUB08731MIG
Created by admin on Tue Oct 22 00:25:02 UTC 2019 , Edited by admin on Tue Oct 22 00:25:02 UTC 2019
PRIMARY
DRUG BANK
DB01043
Created by admin on Tue Oct 22 00:25:02 UTC 2019 , Edited by admin on Tue Oct 22 00:25:02 UTC 2019
PRIMARY
WIKIPEDIA
MEMANTINE
Created by admin on Tue Oct 22 00:25:02 UTC 2019 , Edited by admin on Tue Oct 22 00:25:02 UTC 2019
PRIMARY
MERCK INDEX
M7167
Created by admin on Tue Oct 22 00:25:02 UTC 2019 , Edited by admin on Tue Oct 22 00:25:02 UTC 2019
PRIMARY Merck Index
MESH
D008559
Created by admin on Tue Oct 22 00:25:02 UTC 2019 , Edited by admin on Tue Oct 22 00:25:02 UTC 2019
PRIMARY
ChEMBL
CHEMBL807
Created by admin on Tue Oct 22 00:25:02 UTC 2019 , Edited by admin on Tue Oct 22 00:25:02 UTC 2019
PRIMARY