Neramexane

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
Thumb
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).

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

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.

TargetActionsOrganism
UGlutamate receptor ionotropic, NMDA 3ANot AvailableHumans
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
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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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International/Other Brands
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
  1. 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]
  2. 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]
  3. 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]
  4. Rammes G, Schierloh A: Neramexane (merz pharmaceuticals/forest laboratories). IDrugs. 2006 Feb;9(2):128-35. [Article]
PubChem Compound
6433106
PubChem Substance
175426906
ChemSpider
4938294
ChEMBL
CHEMBL2110954
ZINC
ZINC000004217734
Wikipedia
Neramexane

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentAlzheimer's Disease (AD)1
2CompletedTreatmentTinnitus1
1CompletedNot AvailableHealthy Volunteers5
1CompletedBasic ScienceMetabolism of Neramexane1
1CompletedTreatmentHealthy Volunteers1

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
PropertyValueSource
Water Solubility0.0629 mg/mLALOGPS
logP3.74ALOGPS
logP2.63ChemAxon
logS-3.4ALOGPS
pKa (Strongest Basic)10.66ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.02 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity53.62 m3·mol-1ChemAxon
Polarizability21.66 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9863
Blood Brain Barrier+0.9619
Caco-2 permeable+0.6235
P-glycoprotein substrateNon-substrate0.7275
P-glycoprotein inhibitor INon-inhibitor0.925
P-glycoprotein inhibitor IINon-inhibitor0.9232
Renal organic cation transporterNon-inhibitor0.8503
CYP450 2C9 substrateNon-substrate0.8314
CYP450 2D6 substrateNon-substrate0.6113
CYP450 3A4 substrateNon-substrate0.5462
CYP450 1A2 substrateNon-inhibitor0.9335
CYP450 2C9 inhibitorNon-inhibitor0.9234
CYP450 2D6 inhibitorNon-inhibitor0.8153
CYP450 2C19 inhibitorNon-inhibitor0.938
CYP450 3A4 inhibitorNon-inhibitor0.9145
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8614
Ames testNon AMES toxic0.9177
CarcinogenicityNon-carcinogens0.6568
BiodegradationNot ready biodegradable0.8863
Rat acute toxicity2.2242 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.989
hERG inhibition (predictor II)Non-inhibitor0.8495
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein phosphatase 2a binding
Specific 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. May ...
Gene Name
GRIN3A
Uniprot ID
Q8TCU5
Uniprot Name
Glutamate receptor ionotropic, NMDA 3A
Molecular Weight
125464.07 Da

Drug created on October 21, 2007 22:23 / Updated on February 21, 2021 18:51