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Details

Stereochemistry ACHIRAL
Molecular Formula C11H23N.CH4O3S
Molecular Weight 265.413
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NERAMEXANE MESYLATE

SMILES

CS(O)(=O)=O.CC1(C)CC(C)(C)CC(C)(N)C1

InChI

InChIKey=CLUKHUGGXSIGRX-UHFFFAOYSA-N
InChI=1S/C11H23N.CH4O3S/c1-9(2)6-10(3,4)8-11(5,12)7-9;1-5(2,3)4/h6-8,12H2,1-5H3;1H3,(H,2,3,4)

HIDE SMILES / InChI

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

Molecular Formula CH4O3S
Molecular Weight 96.106
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.

Approval Year

PubMed

PubMed

TitleDatePubMed
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
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
Inhibition of the alpha9alpha10 nicotinic cholinergic receptor by neramexane, an open channel blocker of N-methyl-D-aspartate receptors.
2007 Jul 2
Pharmacodynamics of memantine: an update.
2008 Mar
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
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

Patents

Sample Use Guides

Tinnitus: Neramexane 25 -75 mg/d, oral tablets, duration: 16 weeks
Route of Administration: Oral
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 Fri Dec 15 15:59:09 GMT 2023
Edited
by admin
on Fri Dec 15 15:59:09 GMT 2023
Record UNII
9M85GXG84D
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NERAMEXANE MESYLATE
USAN  
USAN  
Official Name English
1,3,3,5,5-Pentamethylcyclohexanamine methanesulfonate
Systematic Name English
CYCLOHEXANAMINE, 1,3,3,5,5-PENTAMETHYL, METHANESULFONATE
Common Name English
Neramexane mesilate [WHO-DD]
Common Name English
NERAMEXANE MESYLATE [USAN]
Common Name English
NERAMEXANE MESILATE
WHO-DD  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C264
Created by admin on Fri Dec 15 15:59:09 GMT 2023 , Edited by admin on Fri Dec 15 15:59:09 GMT 2023
Code System Code Type Description
SMS_ID
100000126341
Created by admin on Fri Dec 15 15:59:09 GMT 2023 , Edited by admin on Fri Dec 15 15:59:09 GMT 2023
PRIMARY
FDA UNII
9M85GXG84D
Created by admin on Fri Dec 15 15:59:09 GMT 2023 , Edited by admin on Fri Dec 15 15:59:09 GMT 2023
PRIMARY
EVMPD
SUB32871
Created by admin on Fri Dec 15 15:59:09 GMT 2023 , Edited by admin on Fri Dec 15 15:59:09 GMT 2023
PRIMARY
NCI_THESAURUS
C75163
Created by admin on Fri Dec 15 15:59:09 GMT 2023 , Edited by admin on Fri Dec 15 15:59:09 GMT 2023
PRIMARY
PUBCHEM
11425584
Created by admin on Fri Dec 15 15:59:09 GMT 2023 , Edited by admin on Fri Dec 15 15:59:09 GMT 2023
PRIMARY
CAS
457068-92-7
Created by admin on Fri Dec 15 15:59:09 GMT 2023 , Edited by admin on Fri Dec 15 15:59:09 GMT 2023
PRIMARY
EPA CompTox
DTXSID10196605
Created by admin on Fri Dec 15 15:59:09 GMT 2023 , Edited by admin on Fri Dec 15 15:59:09 GMT 2023
PRIMARY
ChEMBL
CHEMBL2110954
Created by admin on Fri Dec 15 15:59:09 GMT 2023 , Edited by admin on Fri Dec 15 15:59:09 GMT 2023
PRIMARY
USAN
PP-37
Created by admin on Fri Dec 15 15:59:09 GMT 2023 , Edited by admin on Fri Dec 15 15:59:09 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY