119431-25-3

Usage

Uses

Used in Neuroprotection Applications:
Eliprodil is used as a neuroprotective agent, particularly for blocking ischemia-induced neurodegeneration in the CA1 region of the hippocampus. It modulates NMDA receptor activity and inhibits neuronal calcium channel currents, providing protection against neuronal damage caused by ischemic events.
Used in Pharmaceutical Industry:
Eliprodil is used as a non-competitive NMDA receptor antagonist in the development of drugs targeting neurological disorders. Its selectivity for NR2B subunit-containing receptors and high affinity for σ1 and σ2 sites make it a promising candidate for the treatment of various central nervous system conditions.
Used in Research Applications:
Eliprodil is used as a research tool for studying the role of NMDA receptors and their subtypes in various neurological processes. Its selectivity and affinity for specific binding sites make it valuable for investigating the mechanisms underlying neuroprotection and other related phenomena.

Biological Activity

Non-competitive NMDA receptor antagonist that acts at the polyamine modulatory site. Selective for NR2B- over NR2A- and NR2C-containing receptors (IC 50 values are 1, > 100 and > 100 μ M respectively). Also σ 1 ligand (K i = 0.013 μ M). Antagonizes neuronal voltage-gated Ca 2+ channels and selectively inhibits the rapid component of the delayed rectifier K + current (I Kr ). Neuroprotective.

Biological Activity

Eliprodil (SL-820715) is a non-competitive, NR2B-selective NMDA antagonist with IC50 of 1 μM. Its IC50 is greater than 100 μM for receptors containing NR2A and NR2C.

InChI:InChI=1/C20H23ClFNO/c21-18-5-3-17(4-6-18)20(24)14-23-11-9-16(10-12-23)13-15-1-7-19(22)8-2-15/h1-8,16,20,24H,9-14H2

Upstream product

• 536-38-9 4-chlorobenzoylmethyl bromide 
• 92822-03-2 4-(4-fluorobenzyl)piperidine hydrochloride 
• 291773-74-5 1-(4-chlorophenyl)-2-[4-(4-fluorobenzyl)-piperidin-1-yl]ethanon 

Relevant academic research and scientific papers

Synthesis and resolution of racemic eliprodil and evaluation of the enantiomers of eliprodil as NMDA receptor antagonists

A short synthesis of the NMDA receptor antagonist (rac)-Eliprodil (9) and its resolution into the enantiomers by chiral HPLC is described. The enantiomers (R)-9 and (S)-9 were found to exhibit markedly different affinities for NR2B subunit containing NMDA

Method for preventing dyskinesias

Dyskinesias in humans are prevented by administering a therapeutically effective dose of a NR1A/2B site-selective NMDA receptor antagonist compound to a human.

Method for treating diseased-related or drug-induced dyskinesias

Dyskinesias in humans are treated by administering a therapeutically effective dose of an NR1A/2B site-selective NMDA receptor antagonist compound to a human suffering therefrom.

Therapeutically useful 1-phenyl-2-piperidinoalkanol derivatives

Compounds of the formula: STR1 wherein R1 is hydrogen, halogen, trifluoromethyl, alkyl, hydroxyl, alkyoxy, benzyloxy, alkanoyloxy, or benzoyloxy, or when R2 is hydroxyl or methoxy in the 4-position and R3 is hydrogen, R1 may also represent hydroxymethyl carbamoyl or alkoxycarbonyl, R2 is hydrogen, halogen, alkyl, hydroxyl, or alkoxy, R3 is hydrogen or alkyl, R4 is alkyl (in which case the compounds are (±)-erythro) or when R3 represents hydrogen, R4 may also be hydrogen, and R5 is hydrogen, halogen, alkyl, alkoxy, or three methoxy groups in the 3-, 4- and 5-positions and pharmaceutically acceptable acid addition salts thereof, with the exclusion of compounds wherein: (a) one of R1 and R2 is in the 4-position and is hydroxyl, alkoxy or benzyloxy, the other is in the 3-position and is hydrogen, hydroxyl, alkoxy or benzyloxy, and R3 and R5 are hydrogen and wherein: (b) R1 is in the 4-position and is halogen, R4 is methyl and R2, R3 and R5 are hydrogen, are useful as medicaments.