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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
GlycineB antagonists and partial agonists in rodent models of Parkinson's disease--comparison with uncompetitive N-methyl-D-aspartate receptor antagonist.
1999 Jan
Renaissance of NMDA receptor antagonists: do they have a role in the pharmacotherapy for alcoholism?
2004 Apr
The effects of acamprosate and neramexane on cue-induced reinstatement of ethanol-seeking behavior in rat.
2005 Jun
Anti-allodynic interactions between NMDA receptor channel blockers and morphine or clonidine in neuropathic rats.
2005 Sep 5
Inhibition of the alpha9alpha10 nicotinic cholinergic receptor by neramexane, an open channel blocker of N-methyl-D-aspartate receptors.
2007 Jul 2
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 UTC 2023
Edited
by admin
on Fri Dec 15 15:59:09 UTC 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 UTC 2023 , Edited by admin on Fri Dec 15 15:59:09 UTC 2023
Code System Code Type Description
SMS_ID
100000126341
Created by admin on Fri Dec 15 15:59:09 UTC 2023 , Edited by admin on Fri Dec 15 15:59:09 UTC 2023
PRIMARY
FDA UNII
9M85GXG84D
Created by admin on Fri Dec 15 15:59:09 UTC 2023 , Edited by admin on Fri Dec 15 15:59:09 UTC 2023
PRIMARY
EVMPD
SUB32871
Created by admin on Fri Dec 15 15:59:09 UTC 2023 , Edited by admin on Fri Dec 15 15:59:09 UTC 2023
PRIMARY
NCI_THESAURUS
C75163
Created by admin on Fri Dec 15 15:59:09 UTC 2023 , Edited by admin on Fri Dec 15 15:59:09 UTC 2023
PRIMARY
PUBCHEM
11425584
Created by admin on Fri Dec 15 15:59:09 UTC 2023 , Edited by admin on Fri Dec 15 15:59:09 UTC 2023
PRIMARY
CAS
457068-92-7
Created by admin on Fri Dec 15 15:59:09 UTC 2023 , Edited by admin on Fri Dec 15 15:59:09 UTC 2023
PRIMARY
EPA CompTox
DTXSID10196605
Created by admin on Fri Dec 15 15:59:09 UTC 2023 , Edited by admin on Fri Dec 15 15:59:09 UTC 2023
PRIMARY
ChEMBL
CHEMBL2110954
Created by admin on Fri Dec 15 15:59:09 UTC 2023 , Edited by admin on Fri Dec 15 15:59:09 UTC 2023
PRIMARY
USAN
PP-37
Created by admin on Fri Dec 15 15:59:09 UTC 2023 , Edited by admin on Fri Dec 15 15:59:09 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY