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Details

Stereochemistry ACHIRAL
Molecular Formula C12H21N
Molecular Weight 179.3023
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MEMANTINE

SMILES

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

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
Curator's Comment:: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/9120573

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.

Originator

Curator's Comment:: Memantine was first synthesized by Eli Lilly and Company and patented in 1968, as documented in the Merck Index, as a derivative of amantadine, an anti-influenza agent.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
NAMENDA

Approved Use

Namenda (memantine hydrochloride) is indicated for the treatment of moderate to severe dementia of the Alzheimer's type.

Launch Date

1.0662624E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
25.34 ng/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MEMANTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
19.69 ng/mL
5 mg 14 times / 2 weeks multiple, oral
dose: 5 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
MEMANTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
6.2 ng/mL
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MEMANTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1853 ng × h/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MEMANTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
386.37 ng × h/mL
5 mg 14 times / 2 weeks multiple, oral
dose: 5 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
MEMANTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
540 ng × h/mL
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MEMANTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
62 h
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MEMANTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
64.57 h
5 mg 14 times / 2 weeks multiple, oral
dose: 5 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
MEMANTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
66.86 h
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MEMANTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
400 mg single, oral
Highest studied dose
Dose: 400 mg
Route: oral
Route: single
Dose: 400 mg
Sources:
unhealthy, adult
n = 1
Health Status: unhealthy
Age Group: adult
Population Size: 1
Sources:
Other AEs: Restlessness, Psychosis...
Other AEs:
Restlessness (1 patient)
Psychosis (1 patient)
Visual hallucinations (1 patient)
Somnolence (1 patient)
Stupor (1 patient)
Loss of consciousness (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Loss of consciousness 1 patient
400 mg single, oral
Highest studied dose
Dose: 400 mg
Route: oral
Route: single
Dose: 400 mg
Sources:
unhealthy, adult
n = 1
Health Status: unhealthy
Age Group: adult
Population Size: 1
Sources:
Psychosis 1 patient
400 mg single, oral
Highest studied dose
Dose: 400 mg
Route: oral
Route: single
Dose: 400 mg
Sources:
unhealthy, adult
n = 1
Health Status: unhealthy
Age Group: adult
Population Size: 1
Sources:
Restlessness 1 patient
400 mg single, oral
Highest studied dose
Dose: 400 mg
Route: oral
Route: single
Dose: 400 mg
Sources:
unhealthy, adult
n = 1
Health Status: unhealthy
Age Group: adult
Population Size: 1
Sources:
Somnolence 1 patient
400 mg single, oral
Highest studied dose
Dose: 400 mg
Route: oral
Route: single
Dose: 400 mg
Sources:
unhealthy, adult
n = 1
Health Status: unhealthy
Age Group: adult
Population Size: 1
Sources:
Stupor 1 patient
400 mg single, oral
Highest studied dose
Dose: 400 mg
Route: oral
Route: single
Dose: 400 mg
Sources:
unhealthy, adult
n = 1
Health Status: unhealthy
Age Group: adult
Population Size: 1
Sources:
Visual hallucinations 1 patient
400 mg single, oral
Highest studied dose
Dose: 400 mg
Route: oral
Route: single
Dose: 400 mg
Sources:
unhealthy, adult
n = 1
Health Status: unhealthy
Age Group: adult
Population Size: 1
Sources:
Overview

Overview

OverviewOther

Drug as perpetrator​Drug as victimTox targets

Tox targets

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
How to overcome resistance of influenza A viruses against adamantane derivatives.
1998 Feb
Anticonvulsants for soman-induced seizure activity.
1999 Mar-Apr
Low affinity channel blocking (uncompetitive) NMDA receptor antagonists as therapeutic agents--toward an understanding of their favorable tolerability.
2000
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
Effect of BD 1047, a sigma1 receptor antagonist, in the animal models predictive of antipsychotic activity.
2006 Sep-Oct
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
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-induced myoclonus and delirium exacerbated by trimethoprim.
2008 Mar
Ca2+ inhibits the association of memantine with N-methyl-D-aspartate (NMDA) receptor-gated ion channels.
2008 Sep
Does memantine induce bradycardia? A study in the French PharmacoVigilance Database.
2008 Sep
Memanti-nium chloride 0.1-hydrate.
2009 Aug 19
Role of N-methyl-D-aspartate receptors in polychlorinated biphenyl mediated neurotoxicity.
2009 Jan 10
Inhibition of apoptosis in human retinal pigment epithelial cells treated with benzo(e)pyrene, a toxic component of cigarette smoke.
2010 May
Sensitive and rapid HPLC method for determination of memantine in human plasma using OPA derivatization and fluorescence detection: application to pharmacokinetic studies.
2010 Oct-Dec
Patents

Sample Use Guides

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
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
NSC-757843
Code 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 Fri Jun 25 22:02:11 UTC 2021 , Edited by admin on Fri Jun 25 22:02:11 UTC 2021
NDF-RT N0000020015
Created by admin on Fri Jun 25 22:02:11 UTC 2021 , Edited by admin on Fri Jun 25 22:02:11 UTC 2021
NCI_THESAURUS C38149
Created by admin on Fri Jun 25 22:02:11 UTC 2021 , Edited by admin on Fri Jun 25 22:02:11 UTC 2021
WHO-ATC N06DX01
Created by admin on Fri Jun 25 22:02:11 UTC 2021 , Edited by admin on Fri Jun 25 22:02:11 UTC 2021
WHO-ATC N06DA52
Created by admin on Fri Jun 25 22:02:11 UTC 2021 , Edited by admin on Fri Jun 25 22:02:11 UTC 2021
WHO-VATC QN06DA52
Created by admin on Fri Jun 25 22:02:11 UTC 2021 , Edited by admin on Fri Jun 25 22:02:11 UTC 2021
NDF-RT N0000175745
Created by admin on Fri Jun 25 22:02:11 UTC 2021 , Edited by admin on Fri Jun 25 22:02:11 UTC 2021
WHO-VATC QN06DX01
Created by admin on Fri Jun 25 22:02:11 UTC 2021 , Edited by admin on Fri Jun 25 22:02:11 UTC 2021
LIVERTOX 597
Created by admin on Fri Jun 25 22:02:11 UTC 2021 , Edited by admin on Fri Jun 25 22:02:11 UTC 2021
WHO-ATC N06DA53
Created by admin on Fri Jun 25 22:02:11 UTC 2021 , Edited by admin on Fri Jun 25 22:02:11 UTC 2021
NDF-RT N0000020015
Created by admin on Fri Jun 25 22:02:11 UTC 2021 , Edited by admin on Fri Jun 25 22:02:11 UTC 2021
EMA ASSESSMENT REPORTS NEMDATINE (AUTHORIZED: ALZHEIMER DISEASE)
Created by admin on Fri Jun 25 22:02:11 UTC 2021 , Edited by admin on Fri Jun 25 22:02:11 UTC 2021
Code System Code Type Description
FDA UNII
W8O17SJF3T
Created by admin on Fri Jun 25 22:02:11 UTC 2021 , Edited by admin on Fri Jun 25 22:02:11 UTC 2021
PRIMARY
RXCUI
6719
Created by admin on Fri Jun 25 22:02:11 UTC 2021 , Edited by admin on Fri Jun 25 22:02:11 UTC 2021
PRIMARY RxNorm
INN
3952
Created by admin on Fri Jun 25 22:02:11 UTC 2021 , Edited by admin on Fri Jun 25 22:02:11 UTC 2021
PRIMARY
CAS
19982-08-2
Created by admin on Fri Jun 25 22:02:11 UTC 2021 , Edited by admin on Fri Jun 25 22:02:11 UTC 2021
PRIMARY
EPA CompTox
19982-08-2
Created by admin on Fri Jun 25 22:02:11 UTC 2021 , Edited by admin on Fri Jun 25 22:02:11 UTC 2021
PRIMARY
HSDB
7327
Created by admin on Fri Jun 25 22:02:11 UTC 2021 , Edited by admin on Fri Jun 25 22:02:11 UTC 2021
PRIMARY
IUPHAR
4253
Created by admin on Fri Jun 25 22:02:11 UTC 2021 , Edited by admin on Fri Jun 25 22:02:11 UTC 2021
PRIMARY
NCI_THESAURUS
C73269
Created by admin on Fri Jun 25 22:02:11 UTC 2021 , Edited by admin on Fri Jun 25 22:02:11 UTC 2021
PRIMARY
CLINICAL_TRIALS.GOV
NCT03527472
Created by admin on Fri Jun 25 22:02:11 UTC 2021 , Edited by admin on Fri Jun 25 22:02:11 UTC 2021
PRIMARY Memantine for the Treatment of Cognitive Impairment in Systemic Lupus Erythematosus (ClearMEMory)
PUBCHEM
4054
Created by admin on Fri Jun 25 22:02:11 UTC 2021 , Edited by admin on Fri Jun 25 22:02:11 UTC 2021
PRIMARY
DRUG CENTRAL
1679
Created by admin on Fri Jun 25 22:02:11 UTC 2021 , Edited by admin on Fri Jun 25 22:02:11 UTC 2021
PRIMARY
EVMPD
SUB08731MIG
Created by admin on Fri Jun 25 22:02:11 UTC 2021 , Edited by admin on Fri Jun 25 22:02:11 UTC 2021
PRIMARY
DRUG BANK
DB01043
Created by admin on Fri Jun 25 22:02:11 UTC 2021 , Edited by admin on Fri Jun 25 22:02:11 UTC 2021
PRIMARY
WIKIPEDIA
MEMANTINE
Created by admin on Fri Jun 25 22:02:11 UTC 2021 , Edited by admin on Fri Jun 25 22:02:11 UTC 2021
PRIMARY
MERCK INDEX
M7167
Created by admin on Fri Jun 25 22:02:11 UTC 2021 , Edited by admin on Fri Jun 25 22:02:11 UTC 2021
PRIMARY Merck Index
MESH
D008559
Created by admin on Fri Jun 25 22:02:11 UTC 2021 , Edited by admin on Fri Jun 25 22:02:11 UTC 2021
PRIMARY
ChEMBL
CHEMBL807
Created by admin on Fri Jun 25 22:02:11 UTC 2021 , Edited by admin on Fri Jun 25 22:02:11 UTC 2021
PRIMARY