Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Neramexane
- DrugBank Accession Number
- DB04926
- Background
Neramexane is a low-to-moderate affinity uncompetitive NMDA receptor antagonist.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Neramexane (DB04926)
- Weight
- Average: 169.307
Monoisotopic: 169.183049741 - Chemical Formula
- C11H23N
- Synonyms
- Neramexane
Pharmacology
- Indication
Investigated for use/treatment in alzheimer's disease, hearing loss, and pain (acute or chronic).
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Neramexane is similar to memantine and acetylcholinesterase inhibitors in that neramexane targets the cognitive decline in Alzheimer’s Disease by altering neurotransmitter signaling, but not the underlying pathological mechanisms that cause the disease (amyloid production or neurofibrillary tangle accumulation).
- Mechanism of action
Neramexane is an uncompetitive NMDA receptor channel blocker.
Target Actions Organism UGlutamate receptor ionotropic, NMDA 3A Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- 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
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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.Not Available
- Food Interactions
- Not Available
Products
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- Xaprila
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as cyclohexylamines. These are organic compounds containing a cyclohexylamine moiety, which consist of a cyclohexane ring attached to an amine group.
- Kingdom
- Organic compounds
- Super Class
- Organic nitrogen compounds
- Class
- Organonitrogen compounds
- Sub Class
- Cyclohexylamines
- Direct Parent
- Cyclohexylamines
- Alternative Parents
- Organopnictogen compounds / Monoalkylamines / Hydrocarbon derivatives
- Substituents
- Aliphatic homomonocyclic compound / Amine / Cyclohexylamine / Hydrocarbon derivative / Organopnictogen compound / Primary aliphatic amine / Primary amine
- Molecular Framework
- Aliphatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 856DX0KJ84
- CAS number
- 219810-59-0
- InChI Key
- OGZQTTHDGQBLBT-UHFFFAOYSA-N
- InChI
- InChI=1S/C11H23N/c1-9(2)6-10(3,4)8-11(5,12)7-9/h6-8,12H2,1-5H3
- IUPAC Name
- 1,3,3,5,5-pentamethylcyclohexan-1-amine
- SMILES
- CC1(C)CC(C)(C)CC(C)(N)C1
References
- General References
- Plazas PV, Savino J, Kracun S, Gomez-Casati ME, Katz E, Parsons CG, Millar NS, Elgoyhen AB: Inhibition of the alpha9alpha10 nicotinic cholinergic receptor by neramexane, an open channel blocker of N-methyl-D-aspartate receptors. Eur J Pharmacol. 2007 Jul 2;566(1-3):11-9. Epub 2007 Mar 24. [Article]
- Klein T, Magerl W, Hanschmann A, Althaus M, Treede RD: Antihyperalgesic and analgesic properties of the N-methyl-D-aspartate (NMDA) receptor antagonist neramexane in a human surrogate model of neurogenic hyperalgesia. Eur J Pain. 2008 Jan;12(1):17-29. Epub 2007 Apr 20. [Article]
- Kotlinska J, Biala G, Rafalski P, Bochenski M, Danysz W: Effect of neramexane on ethanol dependence and reinforcement. Eur J Pharmacol. 2004 Oct 25;503(1-3):95-8. [Article]
- Rammes G, Schierloh A: Neramexane (merz pharmaceuticals/forest laboratories). IDrugs. 2006 Feb;9(2):128-35. [Article]
- External Links
- PubChem Compound
- 6433106
- PubChem Substance
- 175426906
- ChemSpider
- 4938294
- ChEMBL
- CHEMBL2110954
- ZINC
- ZINC000004217734
- Wikipedia
- Neramexane
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data3 Completed Treatment Alzheimer's Disease (AD) 1 somestatus stop reason just information to hide 2 Completed Treatment Tinnitus 1 somestatus stop reason just information to hide 1 Completed Not Available Healthy Volunteers (HV) 5 somestatus stop reason just information to hide 1 Completed Basic Science Metabolism of Neramexane 1 somestatus stop reason just information to hide 1 Completed Treatment Healthy Volunteers (HV) 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0629 mg/mL ALOGPS logP 3.74 ALOGPS logP 2.63 Chemaxon logS -3.4 ALOGPS pKa (Strongest Basic) 10.66 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 53.62 m3·mol-1 Chemaxon Polarizability 21.66 Å3 Chemaxon Number of Rings 1 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 + 0.9863 Blood Brain Barrier + 0.9619 Caco-2 permeable + 0.6235 P-glycoprotein substrate Non-substrate 0.7275 P-glycoprotein inhibitor I Non-inhibitor 0.925 P-glycoprotein inhibitor II Non-inhibitor 0.9232 Renal organic cation transporter Non-inhibitor 0.8503 CYP450 2C9 substrate Non-substrate 0.8314 CYP450 2D6 substrate Non-substrate 0.6113 CYP450 3A4 substrate Non-substrate 0.5462 CYP450 1A2 substrate Non-inhibitor 0.9335 CYP450 2C9 inhibitor Non-inhibitor 0.9234 CYP450 2D6 inhibitor Non-inhibitor 0.8153 CYP450 2C19 inhibitor Non-inhibitor 0.938 CYP450 3A4 inhibitor Non-inhibitor 0.9145 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8614 Ames test Non AMES toxic 0.9177 Carcinogenicity Non-carcinogens 0.6568 Biodegradation Not ready biodegradable 0.8863 Rat acute toxicity 2.2242 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.989 hERG inhibition (predictor II) Non-inhibitor 0.8495
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0udj-7900000000-e7a95f74e876ef4aa64c Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0229-2900000000-2964af61afaf7a15105f Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-0900000000-0ed1c4d2b961222a73fa Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-0900000000-f6e9e9da555275a78b43 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-08fr-9800000000-dc60b2f925008d0e85c5 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-0900000000-410984fba77d5c30e5e4 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0pb9-9600000000-c0d1050763ee6dbd46ad Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 149.27328 predictedDeepCCS 1.0 (2019) [M+H]+ 151.63129 predictedDeepCCS 1.0 (2019) [M+Na]+ 159.57909 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- NMDA receptor subtype of glutamate-gated ion channels with reduced single-channel conductance, low calcium permeability and low voltage-dependent sensitivity to magnesium. Mediated by glycine. During the development of neural circuits, plays a role in the synaptic refinement period, restricting spine maturation and growth. By competing with GIT1 interaction with ARHGEF7/beta-PIX, may reduce GIT1/ARHGEF7-regulated local activation of RAC1, hence affecting signaling and limiting the maturation and growth of inactive synapses. May also play a role in PPP2CB-NMDAR mediated signaling mechanism
- Specific Function
- calcium channel activity
- Gene Name
- GRIN3A
- Uniprot ID
- Q8TCU5
- Uniprot Name
- Glutamate receptor ionotropic, NMDA 3A
- Molecular Weight
- 125464.07 Da
Drug created at October 21, 2007 22:23 / Updated at February 21, 2021 18:51