Details
Stereochemistry | ACHIRAL |
Molecular Formula | C12H21N.ClH |
Molecular Weight | 215.763 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CC12CC3CC(C)(C1)CC(N)(C3)C2
InChI
InChIKey=LDDHMLJTFXJGPI-UHFFFAOYSA-N
InChI=1S/C12H21N.ClH/c1-10-3-9-4-11(2,6-10)8-12(13,5-9)7-10;/h9H,3-8,13H2,1-2H3;1H
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 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 |
|
Methyl parathion acute toxicity: prophylaxis and therapy with memantine and atropine. | 1990 May-Jun |
|
Inhibition by memantine of the development of persistent oral dyskinesias induced by long-term haloperidol treatment of rats. | 1996 Oct |
|
How to overcome resistance of influenza A viruses against adamantane derivatives. | 1998 Feb |
|
The glutamatergic system and neurodegeneration in dementia: preventive strategies in Alzheimer's disease. | 1999 Jan |
|
Anticonvulsants for soman-induced seizure activity. | 1999 Mar-Apr |
|
A double-blind, placebo-controlled multicentre study of memantine in mild to moderate vascular dementia (MMM500). | 2002 Nov |
|
The ability of new non-competitive glutamate receptor blockers to weaken motor disorders in animals. | 2003 Mar |
|
Mechanisms intrinsic to 5-HT2B receptor-induced potentiation of NMDA receptor responses in frog motoneurones. | 2004 Oct |
|
Safety and tolerability of once-daily versus twice-daily memantine: a randomised, double-blind study in moderate to severe Alzheimer's disease. | 2007 Mar |
|
Effects of memantine on neuronal structure and conditioned fear in the Tg2576 mouse model of Alzheimer's disease. | 2008 Dec |
|
Memantine and NMDA antagonism for chronic migraine: a potentially novel therapeutic approach? | 2008 Feb |
|
Galantamine-induced pisa syndrome: memantine as an alternative. | 2008 Jun |
|
Memantine-induced myoclonus and delirium exacerbated by trimethoprim. | 2008 Mar |
|
Profound pain reduction after induction of memantine treatment in two patients with severe phantom limb pain. | 2008 Oct |
|
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 |
|
Protection of DFP-induced oxidative damage and neurodegeneration by antioxidants and NMDA receptor antagonist. | 2009 Oct 15 |
|
[Effects of electroacupuncture on expression of Abeta positive cells of the hippocampus and SOD activity in rats with streptozocin-Alzheimer's disease]. | 2010 Dec |
|
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 |
|
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 |
|
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 |
|
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.
Substance Class |
Chemical
Created
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admin
on
Edited
Fri Dec 15 15:52:23 UTC 2023
by
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on
Fri Dec 15 15:52:23 UTC 2023
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Record UNII |
JY0WD0UA60
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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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EMA ASSESSMENT REPORTS |
EBIXA (AUTHORIZED: ALZHEIMER DISEASE)
Created by
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EMA ASSESSMENT REPORTS |
MEMANTINE ACCORD (AUTHORIZED: ALZHEIMER DISEASE)
Created by
admin on Fri Dec 15 15:52:24 UTC 2023 , Edited by admin on Fri Dec 15 15:52:24 UTC 2023
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EMA ASSESSMENT REPORTS |
MEMANTINE RATIOPHARM (AUTHORIZED: ALZHEIMER DISEASE)
Created by
admin on Fri Dec 15 15:52:24 UTC 2023 , Edited by admin on Fri Dec 15 15:52:24 UTC 2023
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EMA ASSESSMENT REPORTS |
MEMANTINE LEK (AUTHORIZED: ALZHEIMER DISEASE)
Created by
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EMA ASSESSMENT REPORTS |
AXURA (AUTHORIZED: ALZHEIMER DISEASE)
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EMA ASSESSMENT REPORTS |
BALAXUR (REUFSED: ALZHEIMER DISEASE)
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EMA ASSESSMENT REPORTS |
MEMANTINE MERZ (AUTHORIZED: ALZHEIMER DISEASE)
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admin on Fri Dec 15 15:52:24 UTC 2023 , Edited by admin on Fri Dec 15 15:52:24 UTC 2023
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EMA ASSESSMENT REPORTS |
MEMANTINE MYLAN (AUTHORIZED: ALZHEIMER DISEASE)
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admin on Fri Dec 15 15:52:24 UTC 2023 , Edited by admin on Fri Dec 15 15:52:24 UTC 2023
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EMA ASSESSMENT REPORTS |
ACRESCENT (REFUSED: ALZHEIMER DISEASE)
Created by
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NCI_THESAURUS |
C38149
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EMA ASSESSMENT REPORTS |
MARIXINO (AUTHORIZED: ALZHEIMER DISEASE)
Created by
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DBSALT000456
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64323
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MACUGEN
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CHEMBL807
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236685
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DTXSID90961439
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C47601
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41100-52-1
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JY0WD0UA60
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SUB03137MIG
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m7167
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255-219-6
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PP-38
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