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Details

Stereochemistry RACEMIC
Molecular Formula C20H23ClFNO
Molecular Weight 347.854
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ELIPRODIL

SMILES

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

InChI

InChIKey=GGUSQTSTQSHJAH-UHFFFAOYSA-N
InChI=1S/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

HIDE SMILES / InChI

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 receptor antagonists do not block the development of sensitization of catalepsy, but make its expression state-dependent.
2001 Apr
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
Glutamate AMPA receptor antagonist treatment for ischaemic stroke.
2002
NR2B selective NMDA receptor antagonists.
2002
An MCASE approach to the search of a cure for Parkinson's Disease.
2002 Apr 2
Spermidine attenuates the inhibitory effect of ethanol on NMDA-induced neurotoxicity.
2002 Aug
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
Glutamate-dependent regulation of cholinergic phenotype in hypothalamic neurons.
2003 Dec 19
Polyamines in the brain: distribution, biological interactions, and their potential therapeutic role in brain ischaemia.
2007
Pigment epithelium-derived factor protects retinal ganglion cells.
2007 Jan 29
Hypoxia-ischemia and retinal ganglion cell damage.
2008 Dec
Pharmacology and therapeutic potential of sigma(1) receptor ligands.
2008 Dec
Alcohol related changes in regulation of NMDA receptor functions.
2008 Mar
A new homogeneous high-throughput screening assay for profiling compound activity on the human ether-a-go-go-related gene channel.
2009 Nov 1
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
The site specific demethylation in the 5'-regulatory area of NMDA receptor 2B subunit gene associated with CIE-induced up-regulation of transcription.
2010 Jan 20
Antidepressants are a rational complementary therapy for the treatment of Alzheimer's disease.
2010 Mar 12
Development of a selective competitive receptor binding assay for the determination of the affinity to NR2B containing NMDA receptors.
2010 Nov 2
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 Thu Jul 06 21:51:52 UTC 2023
Edited
by admin
on Thu Jul 06 21:51:52 UTC 2023
Record UNII
YW62A6TW29
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ELIPRODIL
INN  
INN  
Official Name English
eliprodil [INN]
Common Name English
(±)-.ALPHA.-(P-CHLOROPHENYL)-4-(P-FLUOROBENZYL)-1-PIPERIDINEETHANOL
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1509
Created by admin on Thu Jul 06 21:51:53 UTC 2023 , Edited by admin on Thu Jul 06 21:51:53 UTC 2023
Code System Code Type Description
FDA UNII
YW62A6TW29
Created by admin on Thu Jul 06 21:51:53 UTC 2023 , Edited by admin on Thu Jul 06 21:51:53 UTC 2023
PRIMARY
DRUG BANK
DB12869
Created by admin on Thu Jul 06 21:51:53 UTC 2023 , Edited by admin on Thu Jul 06 21:51:53 UTC 2023
PRIMARY
SMS_ID
100000080746
Created by admin on Thu Jul 06 21:51:53 UTC 2023 , Edited by admin on Thu Jul 06 21:51:53 UTC 2023
PRIMARY
WIKIPEDIA
ELIPRODIL
Created by admin on Thu Jul 06 21:51:53 UTC 2023 , Edited by admin on Thu Jul 06 21:51:53 UTC 2023
PRIMARY
EVMPD
SUB06486MIG
Created by admin on Thu Jul 06 21:51:53 UTC 2023 , Edited by admin on Thu Jul 06 21:51:53 UTC 2023
PRIMARY
INN
6900
Created by admin on Thu Jul 06 21:51:53 UTC 2023 , Edited by admin on Thu Jul 06 21:51:53 UTC 2023
PRIMARY
CAS
119431-25-3
Created by admin on Thu Jul 06 21:51:53 UTC 2023 , Edited by admin on Thu Jul 06 21:51:53 UTC 2023
PRIMARY
NCI_THESAURUS
C80994
Created by admin on Thu Jul 06 21:51:53 UTC 2023 , Edited by admin on Thu Jul 06 21:51:53 UTC 2023
PRIMARY
EPA CompTox
DTXSID1045744
Created by admin on Thu Jul 06 21:51:53 UTC 2023 , Edited by admin on Thu Jul 06 21:51:53 UTC 2023
PRIMARY
PUBCHEM
60703
Created by admin on Thu Jul 06 21:51:53 UTC 2023 , Edited by admin on Thu Jul 06 21:51:53 UTC 2023
PRIMARY
ChEMBL
CHEMBL28564
Created by admin on Thu Jul 06 21:51:53 UTC 2023 , Edited by admin on Thu Jul 06 21:51:53 UTC 2023
PRIMARY
MESH
C058083
Created by admin on Thu Jul 06 21:51:53 UTC 2023 , Edited by admin on Thu Jul 06 21:51:53 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY