Identification
- Summary
Memantine is an NMDA receptor antagonist used to treat moderate to severe dementia in Alzheimer's.
- Brand Names
- Axura, Ebixa, Marixino, Namenda, Namenda 49 Titration Pack, Namzaric
- Generic Name
- Memantine
- DrugBank Accession Number
- DB01043
- Background
Initially approved by the FDA in 2013, memantine is an N-methyl-D-aspartate (NMDA) receptor antagonist used in the management of Alzheimer's Disease (AD). It is different from many other Alzheimer's Disease medications, as it works by a different mechanism than the cholinesterase enzyme inhibitors normally employed in the management of Alzheimer's disease 2. Memantine blocks the effects of glutamate, a neurotransmitter in the brain that leads to neuronal excitability and excessive stimulation in Alzheimer's Disease 9.
In 2010, it was estimated that 36 million people worldwide live with Alzheimer's Disease. In 2013, this number increased to 44 million. Almost doubling every 20 years, the prevalence of Alzheimer's Disease is predicted to reach 66 million by 2030 and to 115 million by 2050 13. In December 2013, the G8 dementia summit concluded that dementia should be considered a global priority with the objective of developing a cure or a disease-modifying therapy by the year 2025 10,13.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Memantine (DB01043)
- Weight
- Average: 179.3018
Monoisotopic: 179.167399677 - Chemical Formula
- C12H21N
- Synonyms
- 1-Amino-3,5-dimethyladamantane
- 1,3-Dimethyl-5-adamantanamine
- 3,5-Dimethyl-1-adamantanamine
- 3,5-Dimethyl-1-aminoadamantane
- 3,5-Dimethyltricyclo(3.3.1.1(3,7))decan-1-amine
- Memantina
- Memantine
- Memantinum
- External IDs
- D-145
- DRG-0267
Pharmacology
- Indication
Memantine is used to manage moderate to severe Alzheimer's dementia Label.
A more recent systemic review and meta-analysis 6 indicates that memantine is beneficial as a first line drug for the treatment of Alzheimer's dementia. Cholinesterase inhibitors may be added to memantine for further beneficial effects on behavioral symptoms and other symptoms of dementia 6.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Alzheimer's disease (ad) Combination Product in combination with: Idebenone (DB09081) •••••••••••• ••••••• •••••• Used in combination to treat Moderate-to-severe alzheimer's disease Combination Product in combination with: Ginkgo biloba (DB01381) •••••••••••• ••••••• •••••••••••• Management of Mild vascular dementia ••• ••••• Used in combination to manage Moderate alzheimer's type dementia Combination Product in combination with: Donepezil (DB00843) •••••••••••• Management of Moderate vascular dementia ••• ••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
General effects
This drug inhibits calcium influx into cells that is normally caused by chronic NMDA receptor activation by glutamate 3. This leads to the improvement of Alzheimer's dementia symptoms, demonstrated by increased cognition and other beneficial central nervous system effects 3.
Effects on neuroplasticity
Like other NMDA receptor antagonists, memantine at high doses can reduce neuronal synaptic plasticity that is involved in learning and memory processes. At lower concentrations, which are normally used in the clinical setting, memantine can enhance neuronal synaptic plasticity in the brain, improve memory, and act as a neuroprotectant against the destruction of neurons caused by excitatory neurotransmitters 2.
Effect on various receptors
Memantine has demonstrated minimal activity for GABA, benzodiazepine, dopamine, adrenergic, histamine, and glycine receptors, as well as voltage-dependent Ca2+, Na+ or K+ channels. This drug has shown antagonist activity at the 5HT3 receptors. Laboratory studies suggest that memantine does not affect the reversible inhibition of the acetylcholinesterase normally caused by donepezil, galantamine, or tacrine Label.
- Mechanism of action
Continuous activation of the N-methyl-D-aspartate (NMDA) receptors in the central nervous system caused by glutamate is thought to cause some of the Alzheimer's disease symptoms. This overactivation is thought to contribute to neurotoxicity due to the excitatory properties of glutamate 9. The pharmacological effect of memantine likely occurs via the drug's behavior as an uncompetitive (open-channel) NMDA receptor antagonist, preventing glutamate action on this receptor. Memantine has a preference for the NMDA receptor-operated cation channels. Despite these antagonist effects, memantine has not been proven to prevent or retard the neurodegeneration seen in patients diagnosed with Alzheimer’s disease Label.
Target Actions Organism AGlutamate (NMDA) receptor antagonistHumans U5-hydroxytryptamine receptor 3A antagonistHumans UNeuronal acetylcholine receptor subunit alpha-7 antagonistHumans UDopamine D2 receptor antagonistagonistHumans UGlutamate receptor ionotropic, NMDA 1 binderHumans UGABA(A) Receptor binderHumans UGlycine receptors inhibitorHumans - Absorption
After an oral dose, memantine is well absorbed. Its peak drug concentrations are attained in about 3-7 hours. Memantine shows linear pharmacokinetics when given at normal therapeutic doses. This drug can be taken without regard to food, as there is no effect of food on memantine absorption Label.
- Volume of distribution
The mean volume of distribution of memantine is 9-11 L/kg Label.
- Protein binding
The protein binding for memantine is about 45% Label.
- Metabolism
This drug is partially metabolized in the liver. The hepatic CYP450 enzyme system does not majorly contribute to the metabolism of this drug Label.
Hover over products below to view reaction partners
- Route of elimination
This drug is mainly excreted in the urine. Approximately 48% of administered memantine is excreted unchanged in urine Label.
The remainder of the drug is metabolized to three main metabolites. These metabolites are the N-glucuronide conjugate, 6-hydroxy memantine, and 1-nitroso-deaminated memantine, which show minimal NMDA receptor antagonist activity Label.
- Half-life
The terminal elimination half-life of memantine ranges from 60 to 80 hours in humans.8,12
Following administration of a single oral dose of 10 mg/kg memantine in rats, the elimination half-life was 2.36 ± 0.20 hours. Following a single intravenous dose of 2 mg/kg in rats, the elimination half-life was 2.28 ± 0.48 hours.7
- Clearance
This drug is cleared by active tubular secretion in the kidneys. Tubular reabsorption of this drug is pH dependent Label.
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
LD50
Oral LD50, mouse 437-498 mg/kg 14 Oral LD50, rat 328-370 mg/kg 14
Carcinogenesis, Mutagenesis, Impairment of Fertility
No evidence of carcinogenicity was seen in mouse and rat models administered memantine at doses equivalent to supratherapeutic human doses Label. Additionally, no genotoxic potential was noted when a battery of assays was performed. No effects on fertility or reproductive performance were noted in rats given to 18 mg/kg/day (equivalent to 9 times the maximum recommended human dose) orally from 14 days preceding mating through gestation and lactation in females, or for 60 preceding mating activity in males animals Label.
Use in pregnancy
This drug is considered a pregnancy category B drug, meaning no sufficiently controlled and adequate studies of memantine in pregnant women have been performed. This drug should be taken during pregnancy only if the potential benefit justifies the possible fetal risk Label.
Use in nursing
It is unknown whether memantine is excreted in human milk. Due to that fact that many drugs are found excreted in human milk, caution should be observed when this drug is taken by a nursing mother Label.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Memantine may decrease the excretion rate of Abacavir which could result in a higher serum level. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Memantine. Acebutolol Memantine may increase the bradycardic activities of Acebutolol. Aceclofenac Aceclofenac may decrease the excretion rate of Memantine which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Memantine which could result in a higher serum level. - Food Interactions
- Take with a full glass of water.
- Take with or without food. The absorption is unaffected by food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Memantine hydrochloride JY0WD0UA60 41100-52-1 LDDHMLJTFXJGPI-UHFFFAOYSA-N - Product Images
- International/Other Brands
- Abixa / Akatinol / Memox
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Act Memantine Tablet 10 mg Oral TEVA Canada Limited 2010-02-18 Not applicable Canada 
Act Memantine Tablet 5 mg Oral TEVA Canada Limited Not applicable Not applicable Canada Axura Tablet, film coated 10 mg Oral Merz Pharmaceuticals 2016-09-08 Not applicable EU 
Axura Tablet, film coated 20 mg Oral Merz Pharmaceuticals 2016-09-08 Not applicable EU Axura Tablet, film coated 10 mg Oral Merz Pharmaceuticals 2016-09-08 Not applicable EU - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-memantine Tablet 10 mg Oral Apotex Corporation 2011-06-17 Not applicable Canada Jamp-memantine Tablet 10 mg Oral Jamp Pharma Corporation 2015-02-03 Not applicable Canada Jamp-memantine Tablet 5 mg Oral Jamp Pharma Corporation Not applicable Not applicable Canada Memantine Tablet 5 mg/1 Oral Major Pharmaceuticals 2015-07-20 Not applicable US 
Memantine Tablet 5 mg/1 Oral Northstar RxLLC 2022-09-13 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image BERMAXIN 90/10/5 MG FILM TABLET ,FILM TABLET, 28 ADET Memantine hydrochloride (5 mg) + Donepezil hydrochloride (10 mg) + Idebenone (90 mg) Tablet, film coated Oral CELTİS İLAÇ SAN. VE TİC. A.Ş. 2014-03-31 Not applicable Turkey 
BERMAXIN 90/10/5 MG FILM TABLET ,FILM TABLET, 84 ADET Memantine hydrochloride (5 mg) + Donepezil hydrochloride (10 mg) + Idebenone (90 mg) Tablet, film coated Oral CELTİS İLAÇ SAN. VE TİC. A.Ş. 2014-03-31 Not applicable Turkey COGİTO 5+10+15+20 MG FİLM KAPLI TABLET TEDAVİYE BAŞLAMA PAKETİ, 28 TABLET Memantine hydrochloride (5 mg) + Memantine hydrochloride (10 mg) + Memantine hydrochloride (15 mg) + Memantine hydrochloride (20 mg) Tablet Oral SANTA FARMA İLAÇ SAN. A.Ş. 2015-10-20 Not applicable Turkey COGİTO 5+10+15+20 MG FİLM KAPLI TABLET TEDAVİYE BAŞLAMA PAKETİ, 28 TABLET Memantine hydrochloride (5 mg) + Memantine hydrochloride (10 mg) + Memantine hydrochloride (15 mg) + Memantine hydrochloride (20 mg) Tablet Oral SANTA FARMA İLAÇ SAN. A.Ş. 2015-10-20 Not applicable Turkey COGİTO 5+10+15+20 MG FİLM KAPLI TABLET TEDAVİYE BAŞLAMA PAKETİ, 28 TABLET Memantine hydrochloride (5 mg) + Memantine hydrochloride (10 mg) + Memantine hydrochloride (15 mg) + Memantine hydrochloride (20 mg) Tablet Oral SANTA FARMA İLAÇ SAN. A.Ş. 2015-10-20 Not applicable Turkey - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Generic Drug Memantine hydrochloride (5 mg/1) Tablet Oral Ningbo Shouzheng Medicinal Research Co., Ltd 2020-04-06 2030-04-17 US Generic Drug Memantine hydrochloride (10 mg/1) Tablet Oral Ningbo Shouzheng Medicinal Research Co., Ltd 2020-04-06 2030-04-17 US
Categories
- ATC Codes
- N06DA52 — Donepezil and memantineN06DX01 — MemantineN06DA53 — Donepezil, memantine and ginkgo folium
- Drug Categories
- Anti-Dementia Drugs
- Anti-Dyskinesia Agents
- Anti-Parkinson Drugs
- Bridged-Ring Compounds
- Central Nervous System Agents
- Cholinesterase Inhibitors
- Cytochrome P-450 CYP2A6 Inhibitors
- Cytochrome P-450 CYP2A6 Inhibitors (weak)
- Cytochrome P-450 CYP2B6 Inhibitors
- Cytochrome P-450 CYP2B6 Inhibitors (strong)
- Cytochrome P-450 CYP2C19 Inhibitors
- Cytochrome P-450 CYP2C19 Inhibitors (weak)
- Cytochrome P-450 Enzyme Inhibitors
- Dopamine Agents
- Drugs that are Mainly Renally Excreted
- Excitatory Amino Acid Antagonists
- Miscellaneous Central Nervous System Agents
- N-methyl-D-aspartate Receptor Antagonist
- Nervous System
- Neurotransmitter Agents
- NMDA Receptor Antagonists
- OCT2 Substrates
- Psychoanaleptics
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group.
- Kingdom
- Organic compounds
- Super Class
- Organic nitrogen compounds
- Class
- Organonitrogen compounds
- Sub Class
- Amines
- Direct Parent
- Monoalkylamines
- Alternative Parents
- Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- Aliphatic homopolycyclic compound / Hydrocarbon derivative / Organopnictogen compound / Primary aliphatic amine
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- adamantanes, primary aliphatic amine (CHEBI:64312)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- W8O17SJF3T
- CAS number
- 19982-08-2
- InChI Key
- BUGYDGFZZOZRHP-UHFFFAOYSA-N
- InChI
- 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
- IUPAC Name
- 3,5-dimethyladamantan-1-amine
- SMILES
- CC12CC3CC(C)(C1)CC(N)(C3)C2
References
- Synthesis Reference
- US3391142
- General References
- Cacabelos R, Takeda M, Winblad B: The glutamatergic system and neurodegeneration in dementia: preventive strategies in Alzheimer's disease. Int J Geriatr Psychiatry. 1999 Jan;14(1):3-47. [Article]
- Rogawski MA, Wenk GL: The neuropharmacological basis for the use of memantine in the treatment of Alzheimer's disease. CNS Drug Rev. 2003 Fall;9(3):275-308. [Article]
- Robinson DM, Keating GM: Memantine: a review of its use in Alzheimer's disease. Drugs. 2006;66(11):1515-34. [Article]
- Rogawski MA: Low affinity channel blocking (uncompetitive) NMDA receptor antagonists as therapeutic agents--toward an understanding of their favorable tolerability. Amino Acids. 2000;19(1):133-49. [Article]
- Rammes G, Rupprecht R, Ferrari U, Zieglgansberger W, Parsons CG: 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. Neurosci Lett. 2001 Jun 22;306(1-2):81-4. [Article]
- Kishi T, Matsunaga S, Oya K, Nomura I, Ikuta T, Iwata N: Memantine for Alzheimer's Disease: An Updated Systematic Review and Meta-analysis. J Alzheimers Dis. 2017;60(2):401-425. doi: 10.3233/JAD-170424. [Article]
- Lee SH, Kim SH, Noh YH, Choi BM, Noh GJ, Park WD, Kim EJ, Cho IH, Bae CS: Pharmacokinetics of Memantine after a Single and Multiple Dose of Oral and Patch Administration in Rats. Basic Clin Pharmacol Toxicol. 2016 Feb;118(2):122-7. doi: 10.1111/bcpt.12479. Epub 2015 Sep 28. [Article]
- Noetzli M, Guidi M, Ebbing K, Eyer S, Wilhelm L, Michon A, Thomazic V, Alnawaqil AM, Maurer S, Zumbach S, Giannakopoulos P, von Gunten A, Csajka C, Eap CB: Population pharmacokinetic study of memantine: effects of clinical and genetic factors. Clin Pharmacokinet. 2013 Mar;52(3):211-23. doi: 10.1007/s40262-013-0032-2. [Article]
- Brianne Kuns; Dona Varghese (2019). StatPearls: Memantine. StatPearls Publishing.
- 135 million people will live with dementia worldwide by 2050 [Link]
- Sandoz Monograph: Memantine hydrochloride oral tablets [Link]
- FDA Approved Drug Products: NAMENDA (memantine hydrochloride) tablets, for oral use [Link]
- Alzheimer's disease international: Global Impact of Dementia 2013 [File]
- Memantine Product [File]
- External Links
- Human Metabolome Database
- HMDB0015177
- KEGG Drug
- D08174
- KEGG Compound
- C13736
- PubChem Compound
- 4054
- PubChem Substance
- 46506702
- ChemSpider
- 3914
- BindingDB
- 50062599
- 6719
- ChEBI
- 64312
- ChEMBL
- CHEMBL807
- Therapeutic Targets Database
- DAP000493
- PharmGKB
- PA10364
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Memantine
- FDA label
- Download (604 KB)
- MSDS
- Download (65.7 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Not Available Alzheimer's Disease (AD) 1 4 Completed Basic Science Alzheimer's Disease (AD) 1 4 Completed Supportive Care Healthy Subjects (HS) / Schizoaffective Disorders / Schizophrenia 1 4 Completed Treatment Alcohol Dependency / Depression 1 4 Completed Treatment Alzheimer's Disease (AD) 11
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Bryant Ranch Prepack
- Cardinal Health
- Coupler Enterprises Inc.
- Forest Laboratories Inc.
- Forest Pharmaceuticals
- Lake Erie Medical and Surgical Supply
- Lundbeck Inc.
- Murfreesboro Pharmaceutical Nursing Supply
- PD-Rx Pharmaceuticals Inc.
- Physicians Total Care Inc.
- Prepackage Specialists
- Prepak Systems Inc.
- Ranbaxy Laboratories
- Rebel Distributors Corp.
- Resource Optimization and Innovation LLC
- Stat Rx Usa
- Vangard Labs Inc.
- Dosage Forms
Form Route Strength Tablet Oral 15.000 mg Solution / drops Oral 10 mg/g Tablet, film coated Oral 10.0 mg Solution Oral 5 MG Solution Oral 1.0000 g Tablet, orally disintegrating Oral Kit; tablet Oral Tablet, orally disintegrating Oral Kit; tablet, orally disintegrating Oral Tablet, film coated, extended release Oral Tablet, effervescent Tablet, coated Oral Tablet, effervescent Oral Solution Oral 5 mg/50g Solution Oral 5 mg/100g Solution Oral 5 mg/actuation Tablet Oral 10.00 mg Solution / drops Oral Tablet, effervescent Tablet Oral 10.000 mg Tablet, film coated Oral 10.00 mg Solution Oral 10 MG/ML Tablet, film coated Oral 15 MG Tablet, film coated Oral 5 MG Tablet, orally disintegrating Oral 10 MG Tablet, orally disintegrating Oral 20 MG Tablet, film coated Oral Tablet, film coated Oral Capsule, extended release Oral Capsule, extended release Oral 21 mg/1 Capsule, extended release Oral 7 mg/1 Capsule, extended release; kit Oral Kit Oral Liquid Oral 2 mg/1mL Solution Oral 10 mg/5mL Tablet, coated Oral 10 mg/1 Tablet, coated Oral 5 mg/1 Tablet, film coated Oral 10 mg/1 Tablet, film coated Oral 5 mg/1 Tablet Oral 10 mg Tablet Oral 20 mg Tablet Oral 5 mg Tablet, coated Oral 5 mg Solution Oral 5 mg/ pump actuation Tablet, film coated Oral 10.000 mg Solution Oral 10 MG/G Solution Oral 1.000 g Tablet Oral Capsule, coated pellets Oral 14 mg Capsule, coated pellets Oral 28 mg Capsule, delayed release pellets Oral Solution Oral 2 mg/1mL Tablet Oral 10 mg/1 Tablet Oral 5 mg/1 Capsule, extended release Oral 14 mg/1 Capsule, extended release Oral 28 mg/1 Capsule Oral Tablet Oral 20.000 mg Kit; tablet, film coated Oral Tablet Oral 5.0 mg Tablet Oral Capsule, liquid filled Oral 5 mg Capsule, liquid filled Oral 10 mg Capsule, liquid filled Oral 1000000 mg Solution Oral 1000000 mg Solution Oral 10 mg Tablet, coated Oral 10 mg Tablet, film coated Oral 20 mg Tablet, coated Oral 20 mg Solution Oral 5 mg/0.5ml Tablet, film coated Oral 10 mg - Prices
Unit description Cost Unit Namenda 10 mg tablet 3.38USD tablet Namenda 5 mg tablet 3.32USD tablet Namenda 5-10 mg titration pk 3.32USD each DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region CA2426492 No 2006-10-03 2023-05-08 Canada US8173708 Yes 2012-05-08 2026-05-22 US US8283379 Yes 2012-10-09 2026-05-22 US US8362085 Yes 2013-01-29 2026-05-22 US US8039009 Yes 2011-10-18 2029-09-24 US US8329752 Yes 2012-12-11 2026-05-22 US US8598233 Yes 2013-12-03 2026-05-22 US US8168209 Yes 2012-05-01 2026-05-22 US US8338486 No 2012-12-25 2025-11-22 US US8058291 No 2011-11-15 2029-12-05 US US8580858 No 2013-11-12 2025-11-22 US US8338485 No 2012-12-25 2025-11-22 US US8293794 No 2012-10-23 2025-11-22 US US5061703 Yes 1991-10-29 2015-10-11 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 153 https://www.lookchem.com/Memantine/ boiling point (°C) 239.8 https://www.lookchem.com/Memantine/ water solubility soluble in water https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/021627lbl.pdf logP 3.28 https://www.lundbeck.com/upload/ca/en/files/pdf/pm/Ebixa.pdf pKa 10.27 https://www.lundbeck.com/upload/ca/en/files/pdf/pm/Ebixa.pdf - Predicted Properties
Property Value Source Water Solubility 0.0455 mg/mL ALOGPS logP 3.31 ALOGPS logP 2.07 Chemaxon logS -3.6 ALOGPS pKa (Strongest Basic) 10.7 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 26.02 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 54.49 m3·mol-1 Chemaxon Polarizability 21.82 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9939 Blood Brain Barrier + 0.9823 Caco-2 permeable + 0.6082 P-glycoprotein substrate Non-substrate 0.6403 P-glycoprotein inhibitor I Non-inhibitor 0.82 P-glycoprotein inhibitor II Non-inhibitor 0.7555 Renal organic cation transporter Non-inhibitor 0.7774 CYP450 2C9 substrate Non-substrate 0.8213 CYP450 2D6 substrate Non-substrate 0.6153 CYP450 3A4 substrate Non-substrate 0.5319 CYP450 1A2 substrate Non-inhibitor 0.9327 CYP450 2C9 inhibitor Non-inhibitor 0.9281 CYP450 2D6 inhibitor Non-inhibitor 0.872 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6795 Ames test Non AMES toxic 0.6945 Carcinogenicity Non-carcinogens 0.7426 Biodegradation Not ready biodegradable 0.9633 Rat acute toxicity 2.3455 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9839 hERG inhibition (predictor II) Non-inhibitor 0.6818
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 140.6689766 predictedDarkChem Lite v0.1.0 [M-H]- 146.82977 predictedDeepCCS 1.0 (2019) [M+H]+ 141.2046766 predictedDarkChem Lite v0.1.0 [M+H]+ 149.18777 predictedDeepCCS 1.0 (2019) [M+Na]+ 140.9065766 predictedDarkChem Lite v0.1.0 [M+Na]+ 156.82892 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Voltage-gated cation channel activity
- Specific Function
- NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine. This protein plays a key role in synaptic p...
Components:
References
- Robinson DM, Keating GM: Memantine: a review of its use in Alzheimer's disease. Drugs. 2006;66(11):1515-34. [Article]
- Cacabelos R, Takeda M, Winblad B: The glutamatergic system and neurodegeneration in dementia: preventive strategies in Alzheimer's disease. Int J Geriatr Psychiatry. 1999 Jan;14(1):3-47. [Article]
- Rogawski MA, Wenk GL: The neuropharmacological basis for the use of memantine in the treatment of Alzheimer's disease. CNS Drug Rev. 2003 Fall;9(3):275-308. [Article]
- Memantine FDA label [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Voltage-gated potassium channel activity
- Specific Function
- This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor is a ligand-gate...
- Gene Name
- HTR3A
- Uniprot ID
- P46098
- Uniprot Name
- 5-hydroxytryptamine receptor 3A
- Molecular Weight
- 55279.835 Da
References
- Rammes G, Rupprecht R, Ferrari U, Zieglgansberger W, Parsons CG: 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. Neurosci Lett. 2001 Jun 22;306(1-2):81-4. [Article]
- Nisijima K, Shioda K, Yoshino T, Takano K, Kato S: Memantine, an NMDA antagonist, prevents the development of hyperthermia in an animal model for serotonin syndrome. Pharmacopsychiatry. 2004 Mar;37(2):57-62. doi: 10.1055/s-2004-815526. [Article]
- Memantine FDA label [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Toxic substance binding
- Specific Function
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The cha...
- Gene Name
- CHRNA7
- Uniprot ID
- P36544
- Uniprot Name
- Neuronal acetylcholine receptor subunit alpha-7
- Molecular Weight
- 56448.925 Da
References
- Aracava Y, Pereira EF, Maelicke A, Albuquerque EX: Memantine blocks alpha7* nicotinic acetylcholine receptors more potently than n-methyl-D-aspartate receptors in rat hippocampal neurons. J Pharmacol Exp Ther. 2005 Mar;312(3):1195-205. Epub 2004 Nov 2. [Article]
- Maskell PD, Speder P, Newberry NR, Bermudez I: Inhibition of human alpha 7 nicotinic acetylcholine receptors by open channel blockers of N-methyl-D-aspartate receptors. Br J Pharmacol. 2003 Dec;140(7):1313-9. doi: 10.1038/sj.bjp.0705559. [Article]
- Pohanka M: Alpha7 nicotinic acetylcholine receptor is a target in pharmacology and toxicology. Int J Mol Sci. 2012;13(2):2219-38. doi: 10.3390/ijms13022219. Epub 2012 Feb 17. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- AntagonistAgonist
- General Function
- Potassium channel regulator activity
- Specific Function
- Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
- Gene Name
- DRD2
- Uniprot ID
- P14416
- Uniprot Name
- D(2) dopamine receptor
- Molecular Weight
- 50618.91 Da
References
- Seeman P, Caruso C, Lasaga M: Memantine agonist action at dopamine D2High receptors. Synapse. 2008 Feb;62(2):149-53. [Article]
- Serra G, Demontis F, Serra F, De Chiara L, Spoto A, Girardi P, Vidotto G, Serra G: Memantine: New prospective in bipolar disorder treatment. World J Psychiatry. 2014 Dec 22;4(4):80-90. doi: 10.5498/wjp.v4.i4.80. [Article]
- Nakaya K, Nakagawasai O, Arai Y, Onogi H, Sato A, Niijima F, Tan-No K, Tadano T: Pharmacological characterizations of memantine-induced disruption of prepulse inhibition of the acoustic startle response in mice: involvement of dopamine D2 and 5-HT2A receptors. Behav Brain Res. 2011 Mar 17;218(1):165-73. doi: 10.1016/j.bbr.2010.11.053. Epub 2010 Dec 3. [Article]
- Mancini M, Ghiglieri V, Bagetta V, Pendolino V, Vannelli A, Cacace F, Mineo D, Calabresi P, Picconi B: Memantine alters striatal plasticity inducing a shift of synaptic responses toward long-term depression. Neuropharmacology. 2016 Feb;101:341-50. doi: 10.1016/j.neuropharm.2015.10.015. Epub 2015 Dec 3. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- Curator comments
- This is a potential target. There are limited data regarding this target in the literature.
- General Function
- Voltage-gated cation channel activity
- Specific Function
- NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine. This protein plays a key role in synaptic p...
- Gene Name
- GRIN1
- Uniprot ID
- Q05586
- Uniprot Name
- Glutamate receptor ionotropic, NMDA 1
- Molecular Weight
- 105371.945 Da
References
- Kotermanski SE, Wood JT, Johnson JW: Memantine binding to a superficial site on NMDA receptors contributes to partial trapping. J Physiol. 2009 Oct 1;587(Pt 19):4589-604. doi: 10.1113/jphysiol.2009.176297. Epub 2009 Aug 17. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- Curator comments
- The binding of memantine to this target is believed to be low to negligible.
- General Function
- Inhibitory extracellular ligand-gated ion channel activity
- Specific Function
- Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
Components:
References
- Molinaro G, Battaglia G, Riozzi B, Di Menna L, Rampello L, Bruno V, Nicoletti F: Memantine treatment reduces the expression of the K(+)/Cl(-) cotransporter KCC2 in the hippocampus and cerebral cortex, and attenuates behavioural responses mediated by GABA(A) receptor activation in mice. Brain Res. 2009 Apr 10;1265:75-9. doi: 10.1016/j.brainres.2009.02.016. Epub 2009 Feb 21. [Article]
- Memantine FDA label [File]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Transmitter-gated ion channel activity
- Specific Function
- The glycine receptor is a neurotransmitter-gated ion channel. Binding of glycine to its receptor increases the chloride conductance and thus produces hyperpolarization (inhibition of neuronal firing).
Components:
References
- Xia P, Chen HS, Zhang D, Lipton SA: Memantine preferentially blocks extrasynaptic over synaptic NMDA receptor currents in hippocampal autapses. J Neurosci. 2010 Aug 18;30(33):11246-50. doi: 10.1523/JNEUROSCI.2488-10.2010. [Article]
- Limapichat W, Yu WY, Branigan E, Lester HA, Dougherty DA: Key binding interactions for memantine in the NMDA receptor. ACS Chem Neurosci. 2013 Feb 20;4(2):255-60. doi: 10.1021/cn300180a. Epub 2012 Dec 7. [Article]
- Memantine FDA label [File]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- Data are based on the results of an in vitro study. Current information in the literature regarding this enzyme action is limited.
- General Function
- Steroid hydroxylase activity
- Specific Function
- Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
- Gene Name
- CYP2A6
- Uniprot ID
- P11509
- Uniprot Name
- Cytochrome P450 2A6
- Molecular Weight
- 56501.005 Da
References
- Micuda S, Mundlova L, Anzenbacherova E, Anzenbacher P, Chladek J, Fuksa L, Martinkova J: Inhibitory effects of memantine on human cytochrome P450 activities: prediction of in vivo drug interactions. Eur J Clin Pharmacol. 2004 Oct;60(8):583-9. doi: 10.1007/s00228-004-0825-1. Epub 2004 Sep 16. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- There is limited current data available on this enzyme inhibition, with the exception of one in vitro study.
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55930.545 Da
References
- Micuda S, Mundlova L, Anzenbacherova E, Anzenbacher P, Chladek J, Fuksa L, Martinkova J: Inhibitory effects of memantine on human cytochrome P450 activities: prediction of in vivo drug interactions. Eur J Clin Pharmacol. 2004 Oct;60(8):583-9. doi: 10.1007/s00228-004-0825-1. Epub 2004 Sep 16. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- Data are limited to the results of an in vitro study. Current information in the literature is limited.
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- Micuda S, Mundlova L, Anzenbacherova E, Anzenbacher P, Chladek J, Fuksa L, Martinkova J: Inhibitory effects of memantine on human cytochrome P450 activities: prediction of in vivo drug interactions. Eur J Clin Pharmacol. 2004 Oct;60(8):583-9. doi: 10.1007/s00228-004-0825-1. Epub 2004 Sep 16. [Article]
- Korhonen LE, Turpeinen M, Rahnasto M, Wittekindt C, Poso A, Pelkonen O, Raunio H, Juvonen RO: New potent and selective cytochrome P450 2B6 (CYP2B6) inhibitors based on three-dimensional quantitative structure-activity relationship (3D-QSAR) analysis. Br J Pharmacol. 2007 Apr;150(7):932-42. doi: 10.1038/sj.bjp.0707173. Epub 2007 Feb 26. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- Curator comments
- This transporter is a potential transporter and has not been confirmed.
- General Function
- Quaternary ammonium group transmembrane transporter activity
- Specific Function
- Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
- Gene Name
- SLC22A2
- Uniprot ID
- O15244
- Uniprot Name
- Solute carrier family 22 member 2
- Molecular Weight
- 62579.99 Da
References
- Busch AE, Karbach U, Miska D, Gorboulev V, Akhoundova A, Volk C, Arndt P, Ulzheimer JC, Sonders MS, Baumann C, Waldegger S, Lang F, Koepsell H: Human neurons express the polyspecific cation transporter hOCT2, which translocates monoamine neurotransmitters, amantadine, and memantine. Mol Pharmacol. 1998 Aug;54(2):342-52. [Article]
- Muller F, Weitz D, Derdau V, Sandvoss M, Mertsch K, Konig J, Fromm MF: Contribution of MATE1 to Renal Secretion of the NMDA Receptor Antagonist Memantine. Mol Pharm. 2017 Sep 5;14(9):2991-2998. doi: 10.1021/acs.molpharmaceut.7b00179. Epub 2017 Aug 2. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Curator comments
- This is a potential transporter and has not been confirmed.
- General Function
- Solute:proton antiporter activity
- Specific Function
- Involved in pH regulation to eliminate acids generated by active metabolism or to counter adverse environmental conditions. Major proton extruding system driven by the inward sodium ion chemical gr...
- Gene Name
- SLC9A1
- Uniprot ID
- P19634
- Uniprot Name
- Sodium/hydrogen exchanger 1
- Molecular Weight
- 90762.13 Da
References
- Mehta DC, Short JL, Nicolazzo JA: Memantine transport across the mouse blood-brain barrier is mediated by a cationic influx H+ antiporter. Mol Pharm. 2013 Dec 2;10(12):4491-8. doi: 10.1021/mp400316e. Epub 2013 Oct 29. [Article]
- Mehta DC, Short JL, Nicolazzo JA: Reduced CNS exposure of memantine in a triple transgenic mouse model of Alzheimer's disease assessed using a novel LC-MS technique. J Pharm Biomed Anal. 2013 Nov;85:198-206. doi: 10.1016/j.jpba.2013.07.027. Epub 2013 Jul 30. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Curator comments
- This is a potential transporter and has not been confirmed.
- General Function
- Symporter activity
- Specific Function
- Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without...
- Gene Name
- SLC22A4
- Uniprot ID
- Q9H015
- Uniprot Name
- Solute carrier family 22 member 4
- Molecular Weight
- 62154.48 Da
References
- Mehta DC, Short JL, Nicolazzo JA: Memantine transport across the mouse blood-brain barrier is mediated by a cationic influx H+ antiporter. Mol Pharm. 2013 Dec 2;10(12):4491-8. doi: 10.1021/mp400316e. Epub 2013 Oct 29. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Curator comments
- This is a potential transporter and has not been confirmed.
- General Function
- Monovalent cation:proton antiporter activity
- Specific Function
- Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide (NMN), metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfat...
- Gene Name
- SLC47A1
- Uniprot ID
- Q96FL8
- Uniprot Name
- Multidrug and toxin extrusion protein 1
- Molecular Weight
- 61921.585 Da
References
- Muller F, Weitz D, Derdau V, Sandvoss M, Mertsch K, Konig J, Fromm MF: Contribution of MATE1 to Renal Secretion of the NMDA Receptor Antagonist Memantine. Mol Pharm. 2017 Sep 5;14(9):2991-2998. doi: 10.1021/acs.molpharmaceut.7b00179. Epub 2017 Aug 2. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55