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
Molecular Formula | C11H23N |
Molecular Weight | 169.307 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
---|---|---|
GlycineB antagonists and partial agonists in rodent models of Parkinson's disease--comparison with uncompetitive N-methyl-D-aspartate receptor antagonist. | 1999 Jan |
|
Effects of the NMDA receptor channel blockers memantine and MRZ 2/579 on morphine withdrawal-facilitated aggression in mice. | 2000 May |
|
Effects of a novel uncompetitive NMDA receptor antagonist, MRZ 2/579 on ethanol self-administration and ethanol withdrawal seizures in the rat. | 2001 Feb 9 |
|
Amino-alkyl-cyclohexanes as a novel class of uncompetitive NMDA receptor antagonists. | 2002 |
|
Neramexane. | 2002 |
|
Synergistic effect of uncompetitive NMDA receptor antagonists and antidepressant drugs in the forced swimming test in rats. | 2002 Jun |
|
Are neuronal nicotinic receptors a target for antiepileptic drug development? Studies in different seizure models in mice and rats. | 2003 Apr 11 |
|
Renaissance of NMDA receptor antagonists: do they have a role in the pharmacotherapy for alcoholism? | 2004 Apr |
|
Caffeine withdrawal syndrome in social interaction test in mice: effects of the NMDA receptor channel blockers, memantine and neramexane. | 2004 May |
|
Cognitive deficits following coronary artery bypass grafting: prevalence, prognosis, and therapeutic strategies. | 2004 Oct |
|
Effect of neramexane on ethanol dependence and reinforcement. | 2004 Oct 25 |
|
The effects of acamprosate and neramexane on cue-induced reinstatement of ethanol-seeking behavior in rat. | 2005 Jun |
|
The role of the NMDA receptor in alcohol relapse: a pharmacological mapping study using the alcohol deprivation effect. | 2005 May |
|
Anti-allodynic interactions between NMDA receptor channel blockers and morphine or clonidine in neuropathic rats. | 2005 Sep 5 |
|
Acamprosate: a new tool in the battle against alcohol dependence. | 2006 Dec |
|
Neramexane (merz pharmaceuticals/forest laboratories). | 2006 Feb |
|
N-methyl-D-aspartate and group I metabotropic glutamate receptors are involved in the expression of ethanol-induced sensitization in mice. | 2006 Feb |
|
Enhancement of long-term spatial memory in adult rats by the noncompetitive NMDA receptor antagonists, memantine and neramexane. | 2006 Oct |
|
Enhancement of antidepressant-like effects but not brain-derived neurotrophic factor mRNA expression by the novel N-methyl-D-aspartate receptor antagonist neramexane in mice. | 2006 Sep |
|
Progress update: Pharmacological treatment of Alzheimer's disease. | 2007 |
|
A novel class of amino-alkylcyclohexanes as uncompetitive, fast, voltage-dependent, N-methyl-D-aspartate (NMDA) receptor antagonists--in vitro characterization. | 2007 |
|
Inhibition of the alpha9alpha10 nicotinic cholinergic receptor by neramexane, an open channel blocker of N-methyl-D-aspartate receptors. | 2007 Jul 2 |
|
Antihyperalgesic and analgesic properties of the N-methyl-D-aspartate (NMDA) receptor antagonist neramexane in a human surrogate model of neurogenic hyperalgesia. | 2008 Jan |
|
Pharmacodynamics of memantine: an update. | 2008 Mar |
|
Treatment of alcohol dependence in patients with co-morbid major depressive disorder--predictors for the outcomes with memantine and escitalopram medication. | 2008 Oct 3 |
|
Pharmacological Treatment of Alzheimer's Disease: Is it Progressing Adequately? | 2009 Apr 2 |
|
Antinociceptive effects of chronic administration of uncompetitive NMDA receptor antagonists in a rat model of diabetic neuropathic pain. | 2009 Aug |
|
Glutamatergic and GABAergic modulations of ultrasonic vocalizations during maternal separation distress in mouse pups. | 2009 May |
|
Effects of glutamate and alpha2-noradrenergic receptor antagonists on the development of neurotoxicity produced by chronic rotenone in rats. | 2009 Oct 15 |
|
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:40:54 UTC 2023
by
admin
on
Fri Dec 15 15:40:54 UTC 2023
|
Record UNII |
856DX0KJ84
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NCI_THESAURUS |
C264
Created by
admin on Fri Dec 15 15:40:54 UTC 2023 , Edited by admin on Fri Dec 15 15:40:54 UTC 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
NERAMEXANE
Created by
admin on Fri Dec 15 15:40:54 UTC 2023 , Edited by admin on Fri Dec 15 15:40:54 UTC 2023
|
PRIMARY | |||
|
856DX0KJ84
Created by
admin on Fri Dec 15 15:40:54 UTC 2023 , Edited by admin on Fri Dec 15 15:40:54 UTC 2023
|
PRIMARY | |||
|
DB04926
Created by
admin on Fri Dec 15 15:40:54 UTC 2023 , Edited by admin on Fri Dec 15 15:40:54 UTC 2023
|
PRIMARY | |||
|
CHEMBL2110954
Created by
admin on Fri Dec 15 15:40:54 UTC 2023 , Edited by admin on Fri Dec 15 15:40:54 UTC 2023
|
PRIMARY | |||
|
7928
Created by
admin on Fri Dec 15 15:40:54 UTC 2023 , Edited by admin on Fri Dec 15 15:40:54 UTC 2023
|
PRIMARY | |||
|
6433106
Created by
admin on Fri Dec 15 15:40:54 UTC 2023 , Edited by admin on Fri Dec 15 15:40:54 UTC 2023
|
PRIMARY | |||
|
C76781
Created by
admin on Fri Dec 15 15:40:54 UTC 2023 , Edited by admin on Fri Dec 15 15:40:54 UTC 2023
|
PRIMARY | |||
|
SUB32853
Created by
admin on Fri Dec 15 15:40:54 UTC 2023 , Edited by admin on Fri Dec 15 15:40:54 UTC 2023
|
PRIMARY | |||
|
DTXSID40176399
Created by
admin on Fri Dec 15 15:40:54 UTC 2023 , Edited by admin on Fri Dec 15 15:40:54 UTC 2023
|
PRIMARY | |||
|
C114144
Created by
admin on Fri Dec 15 15:40:54 UTC 2023 , Edited by admin on Fri Dec 15 15:40:54 UTC 2023
|
PRIMARY | |||
|
219810-59-0
Created by
admin on Fri Dec 15 15:40:54 UTC 2023 , Edited by admin on Fri Dec 15 15:40:54 UTC 2023
|
PRIMARY | |||
|
100000126222
Created by
admin on Fri Dec 15 15:40:54 UTC 2023 , Edited by admin on Fri Dec 15 15:40:54 UTC 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
SALT/SOLVATE -> PARENT |
|
||
|
TARGET -> INHIBITOR |
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
|