Details
Stereochemistry | ACHIRAL |
Molecular Formula | C12H21N |
Molecular Weight | 179.3018 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
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
DescriptionSources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021487s010s012s014,021627s008lbl.pdfCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/9120573
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021487s010s012s014,021627s008lbl.pdf
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=15717010
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2094124 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9120573 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | NAMENDA Approved UseNamenda (memantine hydrochloride) is indicated for the treatment of moderate to severe dementia of the Alzheimer's type. Launch Date2003 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
25.34 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18498913 |
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 EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18498913 |
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 EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18498913 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1853 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18498913 |
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 EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18498913 |
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 EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18498913 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
62 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18498913 |
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 EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18498913 |
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 EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/18498913 |
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
Dose | Population | Adverse 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) Sources: Psychosis (1 patient) Visual hallucinations (1 patient) Somnolence (1 patient) Stupor (1 patient) Loss of consciousness (1 patient) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-487_Namenda_Bioeqr_P1.pdf#page=12 Page: 12.0 |
no | |||
yes [Ki 236 uM] | ||||
yes [Ki 3.7 uM] | ||||
yes [Ki 7.3 uM] |
Drug as victim
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-487_Namenda_Pharmr_P1.pdf#page=16 Page: 16.0 |
PubMed
Title | Date | PubMed |
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[Memantine and neurogenic bladder disorders within the bounds of spastic conditions]. | 1982 |
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Methyl parathion acute toxicity: prophylaxis and therapy with memantine and atropine. | 1990 May-Jun |
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Inhibition by memantine of the development of persistent oral dyskinesias induced by long-term haloperidol treatment of rats. | 1996 Oct |
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How to overcome resistance of influenza A viruses against adamantane derivatives. | 1998 Feb |
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Anticonvulsants for soman-induced seizure activity. | 1999 Mar-Apr |
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Anticonvulsant efficacy of N-methyl-D-aspartate antagonists against convulsions induced by cocaine. | 1999 May |
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[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 |
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Effects of the NMDA receptor channel blockers memantine and MRZ 2/579 on morphine withdrawal-facilitated aggression in mice. | 2000 May |
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Uncompetitive antagonists of the N-methyl-D-aspartate (NMDA) receptors alter the mRNA expression of proteins associated with the NMDA receptor complex. | 2001 Feb |
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The N-methyl-D-aspartate receptor channel blockers memantine, MRZ 2/579 and other amino-alkyl-cyclohexanes antagonise 5-HT(3) receptor currents in cultured HEK-293 and N1E-115 cell systems in a non-competitive manner. | 2001 Jun 22 |
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Involvement of nitric oxide in myotoxicity produced by diisopropylphosphorofluoridate (DFP)-induced muscle hyperactivity. | 2002 Dec |
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A double-blind, placebo-controlled multicentre study of memantine in mild to moderate vascular dementia (MMM500). | 2002 Nov |
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The neuropharmacological basis for the use of memantine in the treatment of Alzheimer's disease. | 2003 Fall |
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Delusions and hallucinations in dementia with Lewy bodies: worsening with memantine. | 2005 Aug 9 |
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Development of subtle psychotic symptoms with memantine: a case report. | 2005 May |
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A comparison of the predictive therapeutic and undesired side-effects of the NMDA receptor antagonist, memantine, in mice. | 2005 May |
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Simultaneous liquid chromatographic assay of amantadine and its four related compounds in phosphate-buffered saline using 4-fluoro-7-nitro-2,1,3-benzoxadiazole as a fluorescent derivatization reagent. | 2006 May |
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Effect of BD 1047, a sigma1 receptor antagonist, in the animal models predictive of antipsychotic activity. | 2006 Sep-Oct |
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Memantine as adjunctive therapy in children diagnosed with autistic spectrum disorders: an observation of initial clinical response and maintenance tolerability. | 2007 May |
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Memantine-induced hepatitis with cholestasis in a very elderly patient. | 2008 Apr 15 |
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Memantine prevents the cognitive impairment induced by 3,4-methylenedioxymethamphetamine in rats. | 2008 Jul 28 |
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Methylmercury increases N-methyl-D-aspartate receptors on human SH-SY 5Y neuroblastoma cells leading to neurotoxicity. | 2008 Jul 30 |
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Galantamine-induced pisa syndrome: memantine as an alternative. | 2008 Jun |
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Memantine-induced myoclonus and delirium exacerbated by trimethoprim. | 2008 Mar |
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The attenuating effect of memantine on staurosporine-, salsolinol- and doxorubicin-induced apoptosis in human neuroblastoma SH-SY5Y cells. | 2008 Mar-Apr |
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Ca2+ inhibits the association of memantine with N-methyl-D-aspartate (NMDA) receptor-gated ion channels. | 2008 Sep |
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Does memantine induce bradycardia? A study in the French PharmacoVigilance Database. | 2008 Sep |
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Memanti-nium chloride 0.1-hydrate. | 2009 Aug 19 |
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Memantine dosing in patients with dementia. | 2009 Feb |
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Characteristic effects of anti-dementia drugs on rat sleep patterns. | 2009 Mar |
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Treatment of acquired periodic alternating nystagmus with memantine: a case report. | 2009 Mar-Apr |
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Protection of DFP-induced oxidative damage and neurodegeneration by antioxidants and NMDA receptor antagonist. | 2009 Oct 15 |
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[Effects of electroacupuncture on expression of Abeta positive cells of the hippocampus and SOD activity in rats with streptozocin-Alzheimer's disease]. | 2010 Dec |
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NMDA antagonist memantine improves levodopa-induced dyskinesias and "on-off" phenomena in Parkinson's disease. | 2010 Mar 15 |
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Memantine ameliorates scopolamine-induced amnesia in chicks trained on taste-avoidance learning. | 2010 May |
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Inhibition of apoptosis in human retinal pigment epithelial cells treated with benzo(e)pyrene, a toxic component of cigarette smoke. | 2010 May |
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Protective effects of memantine and epicatechin on catechol-induced toxicity on Müller cells in vitro. | 2010 May 27 |
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Memantine is a useful drug to prevent the spatial and non-spatial memory deficits induced by methamphetamine in rats. | 2010 Nov |
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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 |
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Antinociceptive Effect of Memantine and Morphine on Vincristine-induced Peripheral Neuropathy in Rats. | 2010 Sep |
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Memantine prevents aluminum-induced cognitive deficit in rats. | 2011 Nov 20 |
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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 |
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Memantine in patients with moderate to severe Alzheimer's disease: meta-analyses using realistic definitions of response. | 2014 |
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Glial activation and post-synaptic neurotoxicity: the key events in Streptozotocin (ICV) induced memory impairment in rats. | 2014 Feb |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19948208
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.
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C1509
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NDF-RT |
N0000020015
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NCI_THESAURUS |
C38149
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WHO-ATC |
N06DX01
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WHO-ATC |
N06DA52
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WHO-VATC |
QN06DA52
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NDF-RT |
N0000175745
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WHO-VATC |
QN06DX01
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LIVERTOX |
NBK547981
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N06DA53
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NDF-RT |
N0000020015
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EMA ASSESSMENT REPORTS |
NEMDATINE (AUTHORIZED: ALZHEIMER DISEASE)
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3952
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C73269
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NCT03527472
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PRIMARY | Memantine for the Treatment of Cognitive Impairment in Systemic Lupus Erythematosus (ClearMEMory) | ||
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DB01043
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MEMANTINE
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m7167
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CHEMBL807
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64312
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ACTIVE MOIETY
METABOLITE INACTIVE (PARENT)
SALT/SOLVATE (PARENT)