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
Molecular Formula | C12H21N |
Molecular Weight | 179.3023 |
Charge | 0 |
Count |
|
Stereochemistry | MIXED |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 |
---|---|---|---|---|
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 |
---|---|---|
Pharmacotoxic psychosis after memantine in Parkinson's disease. | 1991 Oct 19 |
|
gp120 of HIV-1 induces apoptosis in rat cortical cell cultures: prevention by memantine. | 1992 Jul 1 |
|
Low affinity channel blocking (uncompetitive) NMDA receptor antagonists as therapeutic agents--toward an understanding of their favorable tolerability. | 2000 |
|
Uncompetitive antagonists of the N-methyl-D-aspartate (NMDA) receptors alter the mRNA expression of proteins associated with the NMDA receptor complex. | 2001 Feb |
|
NMDA antagonists inhibit the development of ethanol dependence in rats. | 2001 Jan-Feb |
|
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 |
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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 |
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Development of subtle psychotic symptoms with memantine: a case report. | 2005 May |
|
Memantine: a review of its use in Alzheimer's disease. | 2006 |
|
Exacerbation of myoclonus by memantine in a patient with Alzheimer disease. | 2007 Aug |
|
Visual hallucinations and agitation in Alzheimer's disease due to memantine: report of three cases. | 2007 May |
|
Effects of memantine on neuronal structure and conditioned fear in the Tg2576 mouse model of Alzheimer's disease. | 2008 Dec |
|
Memantine prevents the cognitive impairment induced by 3,4-methylenedioxymethamphetamine in rats. | 2008 Jul 28 |
|
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 |
|
Memantine is a useful drug to prevent the spatial and non-spatial memory deficits induced by methamphetamine in rats. | 2010 Nov |
|
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 |
|
Memantine prevents aluminum-induced cognitive deficit in rats. | 2011 Nov 20 |
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Jun 25 22:02:11 UTC 2021
by
admin
on
Fri Jun 25 22:02:11 UTC 2021
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Record UNII |
W8O17SJF3T
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Record Status |
Validated (UNII)
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Record Version |
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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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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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Related Record | Type | Details | ||
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TARGET -> AGONIST |
ALZHEIMERS DISEASE DRUG ANTAGONIZING NMDA RECEPTOR, ANTAGONISM OF .ALPHA.7 NACHR IS A SIDE PATHWAY.
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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BINDER->LIGAND |
BINDING
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EXCRETED UNCHANGED |
AMOUNT EXCRETED
URINE
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TRANSPORTER -> SUBSTRATE | |||
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TRANSPORTER -> INHIBITOR |
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METABOLITE INACTIVE -> PARENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Tmax | PHARMACOKINETIC |
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ORAL ADMINISTRATION |
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Biological Half-life | PHARMACOKINETIC |
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Elimination PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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