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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
Neramexane.
2002
Are neuronal nicotinic receptors a target for antiepileptic drug development? Studies in different seizure models in mice and rats.
2003 Apr 11
Caffeine withdrawal syndrome in social interaction test in mice: effects of the NMDA receptor channel blockers, memantine and neramexane.
2004 May
The effects of acamprosate and neramexane on cue-induced reinstatement of ethanol-seeking behavior in rat.
2005 Jun
Acamprosate: a new tool in the battle against alcohol dependence.
2006 Dec
Pharmacological Treatment of Alzheimer's Disease: Is it Progressing Adequately?
2009 Apr 2
Effects of glutamate and alpha2-noradrenergic receptor antagonists on the development of neurotoxicity produced by chronic rotenone in rats.
2009 Oct 15
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 15:40:54 GMT 2023
Edited
by admin
on Fri Dec 15 15:40:54 GMT 2023
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 [INN]
Common Name English
CYCLOHEXANAMINE, 1,3,3,5,5-PENTAMETHYL-
Systematic Name English
1,3,3,5,5-PENTAMETHYLCYCLOHEXANAMINE
Systematic Name English
Neramexane [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C264
Created by admin on Fri Dec 15 15:40:54 GMT 2023 , Edited by admin on Fri Dec 15 15:40:54 GMT 2023
Code System Code Type Description
WIKIPEDIA
NERAMEXANE
Created by admin on Fri Dec 15 15:40:54 GMT 2023 , Edited by admin on Fri Dec 15 15:40:54 GMT 2023
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FDA UNII
856DX0KJ84
Created by admin on Fri Dec 15 15:40:54 GMT 2023 , Edited by admin on Fri Dec 15 15:40:54 GMT 2023
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DRUG BANK
DB04926
Created by admin on Fri Dec 15 15:40:54 GMT 2023 , Edited by admin on Fri Dec 15 15:40:54 GMT 2023
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ChEMBL
CHEMBL2110954
Created by admin on Fri Dec 15 15:40:54 GMT 2023 , Edited by admin on Fri Dec 15 15:40:54 GMT 2023
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INN
7928
Created by admin on Fri Dec 15 15:40:54 GMT 2023 , Edited by admin on Fri Dec 15 15:40:54 GMT 2023
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PUBCHEM
6433106
Created by admin on Fri Dec 15 15:40:54 GMT 2023 , Edited by admin on Fri Dec 15 15:40:54 GMT 2023
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NCI_THESAURUS
C76781
Created by admin on Fri Dec 15 15:40:54 GMT 2023 , Edited by admin on Fri Dec 15 15:40:54 GMT 2023
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EVMPD
SUB32853
Created by admin on Fri Dec 15 15:40:54 GMT 2023 , Edited by admin on Fri Dec 15 15:40:54 GMT 2023
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EPA CompTox
DTXSID40176399
Created by admin on Fri Dec 15 15:40:54 GMT 2023 , Edited by admin on Fri Dec 15 15:40:54 GMT 2023
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MESH
C114144
Created by admin on Fri Dec 15 15:40:54 GMT 2023 , Edited by admin on Fri Dec 15 15:40:54 GMT 2023
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CAS
219810-59-0
Created by admin on Fri Dec 15 15:40:54 GMT 2023 , Edited by admin on Fri Dec 15 15:40:54 GMT 2023
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SMS_ID
100000126222
Created by admin on Fri Dec 15 15:40:54 GMT 2023 , Edited by admin on Fri Dec 15 15:40:54 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY