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Details

Stereochemistry RACEMIC
Molecular Formula C20H23ClFNO.ClH
Molecular Weight 384.315
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ELIPRODIL HYDROCHLORIDE

SMILES

Cl.OC(CN1CCC(CC2=CC=C(F)C=C2)CC1)C3=CC=C(Cl)C=C3

InChI

InChIKey=KEGURTCZUGQPDI-UHFFFAOYSA-N
InChI=1S/C20H23ClFNO.ClH/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;1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C20H23ClFNO
Molecular Weight 347.854
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: description was created based on several sources including : https://www.ncbi.nlm.nih.gov/pubmed/9918703 | https://www.ncbi.nlm.nih.gov/pubmed/8901012

Eliprodil, also known as SL 82-0715, is a non-competitive NMDA glutamate receptor antagonist, which targets the polyamine modulatory site and is selective for NR2B subunit-containing receptors. Eliprodil was in phase III clinical trial for the treatment of stroke or traumatic brain injury. However, these investigations were failed. One reason suggested for failure was that eliprodil had blocked the synaptic transmission mediated by NMDA receptors, hindering neuronal survival. In addition, eliprodil has been studied in phase II clinical trials for the treatment of Parkinson's disease.

CNS Activity

Curator's Comment: Pharmacologically, the development of clinically useful NMDA antagonists has been difficult, because many competitive and non-competitive antagonists of this receptor are unable to cross the blood-brain barrier, and many others produce undesirable (psychotomimetic) side effects. Unlike other NMDA antagonists, the polyamine site antagonists, such as eliprodil, partition across the blood-brain barrier and produce their actions at a modulatory site without side effects typical of many non-competitive antagonists.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q13224
Gene ID: 2904.0
Gene Symbol: GRIN2B
Target Organism: Homo sapiens (Human)
13.0 nM [Ki]
Target ID: Q99720|||Q7Z653
Gene ID: 10280.0
Gene Symbol: SIGMAR1
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Eliprodil

Approved Use

Unknown
Primary
Eliprodil

Approved Use

Unknown
Primary
Eliprodil

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
NMDA antagonists produce site-selective impairment of accuracy in a delayed nonmatch-to-sample task in rats.
2001 Dec
The NMDA receptor complex: a promising target for novel antiepileptic strategies.
2001 Sep
NR2B selective NMDA receptor antagonists.
2002
Why did NMDA receptor antagonists fail clinical trials for stroke and traumatic brain injury?
2002 Oct
Site-selective N-methyl-D-aspartate and alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionate antagonists produce distinct effects in rats performing complex discriminations.
2002 Sep
Polyamines in the brain: distribution, biological interactions, and their potential therapeutic role in brain ischaemia.
2007
Pharmacology and therapeutic potential of sigma(1) receptor ligands.
2008 Dec
A systematic review of clinical trials of pharmacological interventions for acute ischaemic stroke (1955-2008) that were completed, but not published in full.
2010 Apr 22
Patents

Patents

Sample Use Guides

IV 1.5 mg and 3.0 mg twice daily for 3 days, IV 5.0 mg and 10.0 mg twice daily for 11 days, IV between 2.5 mg and 10 mg per dose, or: 3 mg b.i.d for 3 days iv, followed by 10 mg b.i.d for 11 days p.o and 1,5 mg bid for 3 days i.v, then 5 mg b.i.d for 11 days p.o with 3 month follow-up.
Route of Administration: Other
In Vitro Use Guide
The effect of eliprodil on P-type Ca2+ channels was investigated in acutely dissociated rat Purkinje neurons, by using the whole-cell patch-clamp technique. Eliprodil inhibited in a reversible manner the omega-agatoxin-IVA-sensitive Ba2+ current elicited by step depolarizations from a -80 mV holding voltage (IC50 = 1.9 microM). The Ba2+ current showed steady-state inactivation (V1/2 = -61 mV) which was shifted toward more positive values when the intracellular Ca2+ buffering was increased. In these conditions, the potency of eliprodil was decreased (IC50 = 8.2 microM), suggesting a modulation by intracellular Ca2+ of the eliprodil blockade.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:56:30 UTC 2023
Edited
by admin
on Fri Dec 15 15:56:30 UTC 2023
Record UNII
Y6Q7D9GL4S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ELIPRODIL HYDROCHLORIDE
Common Name English
SL-82.0715 HYDROCHLORIDE
Code English
SL-82.0715 HCL
Code English
(±)-.ALPHA.-(P-CHLOROPHENYL)-4-(P-FLUOROBENZYL)-1-PIPERIDINEETHANOL HYDROCHLORIDE
Common Name English
ELIPRODIL HCL
Common Name English
Code System Code Type Description
PUBCHEM
178359
Created by admin on Fri Dec 15 15:56:30 UTC 2023 , Edited by admin on Fri Dec 15 15:56:30 UTC 2023
PRIMARY
FDA UNII
Y6Q7D9GL4S
Created by admin on Fri Dec 15 15:56:30 UTC 2023 , Edited by admin on Fri Dec 15 15:56:30 UTC 2023
PRIMARY
EPA CompTox
DTXSID40929504
Created by admin on Fri Dec 15 15:56:30 UTC 2023 , Edited by admin on Fri Dec 15 15:56:30 UTC 2023
PRIMARY
CAS
136634-88-3
Created by admin on Fri Dec 15 15:56:30 UTC 2023 , Edited by admin on Fri Dec 15 15:56:30 UTC 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
PARENT -> SALT/SOLVATE
ENANTIOMER -> RACEMATE
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ACTIVE MOIETY