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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
Structure of NERAMEXANE

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

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

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
Amino-alkyl-cyclohexanes as a novel class of uncompetitive NMDA receptor antagonists.
2002
Neramexane.
2002
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
Antihyperalgesic and analgesic properties of the N-methyl-D-aspartate (NMDA) receptor antagonist neramexane in a human surrogate model of neurogenic hyperalgesia.
2008 Jan
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 Mon Mar 31 18:05:20 GMT 2025
Edited
by admin
on Mon Mar 31 18:05:20 GMT 2025
Record UNII
856DX0KJ84
Record Status Validated (UNII)
Record Version
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Name Type Language
NERAMEXANE
INN   WHO-DD  
INN  
Official Name English
Neramexane [WHO-DD]
Preferred Name English
neramexane [INN]
Common Name English
CYCLOHEXANAMINE, 1,3,3,5,5-PENTAMETHYL-
Systematic Name English
1,3,3,5,5-PENTAMETHYLCYCLOHEXANAMINE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C264
Created by admin on Mon Mar 31 18:05:20 GMT 2025 , Edited by admin on Mon Mar 31 18:05:20 GMT 2025
Code System Code Type Description
WIKIPEDIA
NERAMEXANE
Created by admin on Mon Mar 31 18:05:20 GMT 2025 , Edited by admin on Mon Mar 31 18:05:20 GMT 2025
PRIMARY
FDA UNII
856DX0KJ84
Created by admin on Mon Mar 31 18:05:20 GMT 2025 , Edited by admin on Mon Mar 31 18:05:20 GMT 2025
PRIMARY
DRUG BANK
DB04926
Created by admin on Mon Mar 31 18:05:20 GMT 2025 , Edited by admin on Mon Mar 31 18:05:20 GMT 2025
PRIMARY
ChEMBL
CHEMBL2110954
Created by admin on Mon Mar 31 18:05:20 GMT 2025 , Edited by admin on Mon Mar 31 18:05:20 GMT 2025
PRIMARY
INN
7928
Created by admin on Mon Mar 31 18:05:20 GMT 2025 , Edited by admin on Mon Mar 31 18:05:20 GMT 2025
PRIMARY
PUBCHEM
6433106
Created by admin on Mon Mar 31 18:05:20 GMT 2025 , Edited by admin on Mon Mar 31 18:05:20 GMT 2025
PRIMARY
NCI_THESAURUS
C76781
Created by admin on Mon Mar 31 18:05:20 GMT 2025 , Edited by admin on Mon Mar 31 18:05:20 GMT 2025
PRIMARY
EVMPD
SUB32853
Created by admin on Mon Mar 31 18:05:20 GMT 2025 , Edited by admin on Mon Mar 31 18:05:20 GMT 2025
PRIMARY
EPA CompTox
DTXSID40176399
Created by admin on Mon Mar 31 18:05:20 GMT 2025 , Edited by admin on Mon Mar 31 18:05:20 GMT 2025
PRIMARY
MESH
C114144
Created by admin on Mon Mar 31 18:05:20 GMT 2025 , Edited by admin on Mon Mar 31 18:05:20 GMT 2025
PRIMARY
CAS
219810-59-0
Created by admin on Mon Mar 31 18:05:20 GMT 2025 , Edited by admin on Mon Mar 31 18:05:20 GMT 2025
PRIMARY
SMS_ID
100000126222
Created by admin on Mon Mar 31 18:05:20 GMT 2025 , Edited by admin on Mon Mar 31 18:05:20 GMT 2025
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY