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
Molecular Formula | C12H21N |
Molecular Weight | 179.3018 |
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 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 |
---|---|---|
Methyl parathion acute toxicity: prophylaxis and therapy with memantine and atropine. | 1990 May-Jun |
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Susceptibility of primary human glial fibrillary acidic protein-positive brain cells to human immunodeficiency virus infection in vitro: anti-HIV activity of memantine. | 1991 Jan |
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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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Synergistic neurotoxicity by human immunodeficiency virus proteins Tat and gp120: protection by memantine. | 2000 Feb |
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Prevention of cocaine-induced convulsions and lethality in mice: effectiveness of targeting different sites on the NMDA receptor complex. | 2000 Jan 28 |
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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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Are neuronal nicotinic receptors a target for antiepileptic drug development? Studies in different seizure models in mice and rats. | 2003 Apr 11 |
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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 |
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Delusions and hallucinations in dementia with Lewy bodies: worsening with memantine. | 2005 Aug 9 |
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Memantine alleviates toxicity induced by dichlorvos in rats. | 2005 Mar |
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Memantine: a review of its use in Alzheimer's disease. | 2006 |
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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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A retrospective study of memantine in children and adolescents with pervasive developmental disorders. | 2007 Mar |
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Visual hallucinations and agitation in Alzheimer's disease due to memantine: report of three cases. | 2007 May |
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[Therapy of Alzheimer's disease: current status and future development]. | 2008 |
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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 and NMDA antagonism for chronic migraine: a potentially novel therapeutic approach? | 2008 Feb |
|
Memantine-induced myoclonus and delirium exacerbated by trimethoprim. | 2008 Mar |
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Does memantine induce bradycardia? A study in the French PharmacoVigilance Database. | 2008 Sep |
|
NMDA antagonist memantine improves levodopa-induced dyskinesias and "on-off" phenomena in Parkinson's disease. | 2010 Mar 15 |
|
Inhibition of apoptosis in human retinal pigment epithelial cells treated with benzo(e)pyrene, a toxic component of cigarette smoke. | 2010 May |
|
Antinociceptive Effect of Memantine and Morphine on Vincristine-induced Peripheral Neuropathy in Rats. | 2010 Sep |
|
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
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Edited
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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 |
NBK547981
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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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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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D008559
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Related Record | Type | Details | ||
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> SUBSTRATE | |||
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TARGET -> INHIBITOR |
ALZHEIMERS DISEASE DRUG ANTAGONIZING NMDA RECEPTOR, ANTAGONISM OF .ALPHA.7 NACHR IS A SIDE PATHWAY.
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BINDER->LIGAND |
BINDING
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EXCRETED UNCHANGED |
AMOUNT EXCRETED
URINE
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TRANSPORTER -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT |
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TRANSPORTER -> INHIBITOR |
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METABOLITE INACTIVE -> PARENT |
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ACTIVE MOIETY |
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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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