Details
Stereochemistry | ACHIRAL |
Molecular Formula | C11H23N |
Molecular Weight | 169.307 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1(C)CC(C)(C)CC(C)(N)C1
InChI
InChIKey=OGZQTTHDGQBLBT-UHFFFAOYSA-N
InChI=1S/C11H23N/c1-9(2)6-10(3,4)8-11(5,12)7-9/h6-8,12H2,1-5H3
Merz Pharmaceuticals GmbH and Forest Laboratories Inc are developing neramexane (MRZ 2/579), an oral N-methyl-D-aspartate antagonist, as a potential neuroprotectant for various central nervous system disorders, including Alzheimer's disease, and for the potential treatment of drug and alcohol dependence, and pain. Similar to memantine, neramexane is an NMDA receptor channel blocker with moderate affinity. It displays voltage dependency, and rapid unblocking kinetics. Neramexane also has been shown to block acetylcholine-evoked responses by antagonizing the alpha-9 alpha-10 nicotinic acetylcholine receptor. Neramexane has a novel mechanism of action and is expected to improve the patients' psychological suffering and difficulties in their life associated with tinnitus by its properties to inhibit the abnormal activity and electric potential of nerve in the inner ear, nerve and cerebral cortex. Neramexane is expected to improve the patients' psychological suffering and difficulties in their life associated with tinnitus by inhibiting the excessive excitation in the auditory pathway from the inner ear to nerve and cerebral cortex via mainly its two pharmacological properties. 1) Neramexane inhibits the excessive nerve excitation in the auditory pathway between the inner ear and cerebral cortex via NMDA antagonistic activity. 2) Neramexane inhibits the nerve excitation in the inner ear via nicotinic acetylcholine receptor antagonistic activity. A phase III trial is currently under investigation for tinnitus.
Originator
Approval Year
PubMed
Title | Date | PubMed |
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Effects of the NMDA receptor channel blockers memantine and MRZ 2/579 on morphine withdrawal-facilitated aggression in mice. | 2000 May |
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Neramexane. | 2002 |
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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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Effect of neramexane on ethanol dependence and reinforcement. | 2004 Oct 25 |
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Neramexane (merz pharmaceuticals/forest laboratories). | 2006 Feb |
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A novel class of amino-alkylcyclohexanes as uncompetitive, fast, voltage-dependent, N-methyl-D-aspartate (NMDA) receptor antagonists--in vitro characterization. | 2007 |
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Effects of glutamate and alpha2-noradrenergic receptor antagonists on the development of neurotoxicity produced by chronic rotenone in rats. | 2009 Oct 15 |
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Neuropharmacology of vestibular system disorders. | 2010 Mar |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT00405886
Tinnitus: Neramexane 25 -75 mg/d, oral tablets, duration: 16 weeks
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10494883
Neramexane (MRZ 2/579) blocked steady-state inward current responses of cultured hippocampal neurones to NMDA with an IC50 of 1.11 uM at -70 mV. Much higher concentrations of MRZ 2/579 blocked voltage-activated Ca2+ channels with an IC50 of 340 uM. MRZ 2/579 (10 uM) reduced peak inward current responses of neuronal nicotinic receptors only to 72.3% of control. MRZ 2/579 (10-100 uM) had little or no effect at AMPA and GABA(A) receptors.
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C264
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NERAMEXANE
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6433106
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100000126222
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)