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
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
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 Date1.0662624E12 |
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 |
---|---|---|
[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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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 |
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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 |
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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 |
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Effects of memantine on neuronal structure and conditioned fear in the Tg2576 mouse model of Alzheimer's disease. | 2008 Dec |
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Memantine-induced myoclonus and delirium exacerbated by trimethoprim. | 2008 Mar |
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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 |
|
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 |
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 |
597
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WHO-ATC |
N06DA53
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NDF-RT |
N0000020015
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EMA ASSESSMENT REPORTS |
NEMDATINE (AUTHORIZED: ALZHEIMER DISEASE)
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W8O17SJF3T
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6719
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3952
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19982-08-2
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19982-08-2
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7327
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4253
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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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4054
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1679
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SUB08731MIG
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DB01043
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MEMANTINE
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M7167
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PRIMARY | Merck Index | ||
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D008559
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CHEMBL807
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ACTIVE MOIETY
METABOLITE INACTIVE (PARENT)