ELIPRODIL

Investigational

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12849400
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glutamate receptor ionotropic, NMDA 2B 5 Target ID: Q13224 Gene ID: 2904.0 Gene Symbol: GRIN2B Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9519265	Antagonist 2849		13.0 nM [Ki]
Sigma non-opioid intracellular receptor 1 26 Target ID: Q99720\|\|\|Q7Z653 Gene ID: 10280.0 Gene Symbol: SIGMAR1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/8741023	Antagonist 2849

Conditions

Condition	Modality	Highest Phase	Product
Acute ischemic stroke 19 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3922860/	Primary	Phase III 665	Eliprodil Approved Use Unknown
Parkinson's disease 232 Sources: https://clinicaltrials.gov/show/NCT00001929	Primary	Phase II 1147	Eliprodil Approved Use Unknown
Head injury 5 Sources: http://adisinsight.springer.com/drugs/800001167	Primary	Phase III 665	Eliprodil Approved Use Unknown
Schizophrenia 305 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8741023	Primary	Phase I 438	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
5712 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8719234	15 mg/kg bw single, intravenous dose: 15 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:		ELIPRODIL plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
2657 μg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8719234	15 mg/kg bw single, intravenous dose: 15 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:		ELIPRODIL plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.5 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8719234	15 mg/kg bw single, intravenous dose: 15 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:		ELIPRODIL plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY510425	https://www.001chemical.com/chem/119431-25-3
3B Scientific (Wuhan) Corp	3B3-032330	http://www.3bsc.com/index/pro_info.php?id=53594
AA Blocks	AA000INS	https://www.aablocks.com/goods/Goods/detail?id=AA000INS
Aaron Chemicals	AR000JFK	http://www.aaronchem.com/119431-25-3
abcr GmbH	AB479221	http://www.abcr.com/shop/en/AB479221
AbMole Bioscience	M4833	http://www.abmole.com/products/eliprodil.html
Acadechem	ACDR-003265	http://acadechemical.com/product/15875
Achemtek	0102-028641	http://www.achemtek.com/119431-25-3
AHH Chemical co.,ltd	MT-46887	http://www.ahhchemical.com/product/MT-46887.html
AK Scientific, Inc. (AKSCI)	3607AH	http://www.aksci.com/item_detail.php?cat=3607AH
Alomone Labs	E-155	https://www.alomone.com/p/eliprodil/E-155
Ambeed	A782266	https://www.ambeed.com/products/119431-25-3.html
Ambinter	Amb18046990	http://www.ambinter.com/reference/18046990
Angel Pharmatech	AG-10255	http://www.angelpharmatech.com/119431-25-3.html
Ark Pharm	AK-56580	http://www.arkpharminc.com/products/119431-25-3.html
Ark Pharma Scientific Limited	A-0766	http://www.arkpharmtech.com/product/32717.html
Aurora Fine Chemicals LLC	A17.898.550	http://online.aurorafinechemicals.com/info?ID=A17.898.550
Aurora Fine Chemicals LLC	K16.782.492	http://online.aurorafinechemicals.com/info?ID=K16.782.492
Axon MedChem	1246	https://www.axonmedchem.com/product/1246
BioChemPartner	BCP23813	http://www.biochempartner.com/119431-25-3-BCP23813
BioCrick	BCC7280	http://www.biocrick.com/Eliprodil-BCC7280.html
BioSynth	J-004126	https://www.biosynth.com/en/products/all-products/products/J-004126.html
BLD Pharm	BD113254	http://www.bldpharm.com/products/119431-25-3.html
BOC Sciences	119431-25-3	https://www.bocsci.com/eliprodil-cas-119431-25-3-item-359860.html
Chem Scene	CS-4279	http://www.chemscene.com/119431-25-3.html
ChemMol	97900030	http://www.chemmol.com/chemmol/97900030.html
ChemShuttle	169627	http://www.chemshuttle.com/catalogsearch/result/?q=119431-25-3&cat=
Chemspace	CSSB00000065797	https://chem-space.com/CSSB00000065797
Clearsynth	CS-T-92505	https://www.clearsynth.com/en/CST92505.html
CSNpharm	CSN10256	https://www.csnpharm.com/products/eliprodil.html
DC Chemicals	DC8268	http://www.dcchemicals.com/product_show-Eliprodil.html
EMD Millipore	504539	http://www.emdbiosciences.com/product/504539
eNovation Chemicals	D544427	https://www.enovationchem.com/ProductDetails.asp?ProductID=D544427
eNovation Chemicals	D547961	https://www.enovationchem.com/ProductDetails.asp?ProductID=D547961
eNovation Chemicals	Y0974469	https://www.enovationchem.com/ProductDetails.asp?ProductID=Y0974469
Excenen	EX-A878	http://www.excenen.com/searchresultlist.php?id=119431-25-3
Finetech	FT-0716701	http://www.finetechnology-ind.com/prod/detail/pub/119431-25-3.html
Glentham Life Sciences	GP3119	http://www.glentham.com/products/product/GP3119/
Hello Bio	HB0274	http://www.hellobio.com/eliprodil.html
Lab Network	LN00334591	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00334591
MedChem Express	HY-12881	https://www.medchemexpress.com/Eliprodil.html
Molcore	MC510425	https://www.molcore.com/product/119431-25-3
MolPort	MolPort-003-941-250	https://www.molport.com/shop/molecule-link/MolPort-003-941-250
MuseChem	I000706	https://www.musechem.com/product/I000706.html
Selleck Chemicals	S6731	http://www.selleckchem.com/products/eliprodil.html
Sigma-Aldrich	E2031_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/e2031?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S526997	http://www.smolecule.com/products/s526997
Sun-shine Chemical	Eliprodil	http://www.sun-shinechem.com/Details/Eliprodil/1766/119431-25-3.html
THE BioTek	bt-266982	https://www.thebiotek.com/product/inhibitors/bt-266982
Tocris	2195	https://www.tocris.com/products/eliprodil_2195
Yuhao Chemical	CJ3054	http://www.chemyuhao.com/119431-25-3.html

PubMed

Title	Date	PubMed
Development of a selective competitive receptor binding assay for the determination of the affinity to NR2B containing NMDA receptors.	2010-11-02	20462722
A systematic review of clinical trials of pharmacological interventions for acute ischaemic stroke (1955-2008) that were completed, but not published in full.	2010-04-22	20412562
Antidepressants are a rational complementary therapy for the treatment of Alzheimer's disease.	2010-03-12	20226030
The site specific demethylation in the 5'-regulatory area of NMDA receptor 2B subunit gene associated with CIE-induced up-regulation of transcription.	2010-01-20	20098704
A new homogeneous high-throughput screening assay for profiling compound activity on the human ether-a-go-go-related gene channel.	2009-11-01	19583963
Hypoxia-ischemia and retinal ganglion cell damage.	2008-12	19668442
Pharmacology and therapeutic potential of sigma(1) receptor ligands.	2008-12	19587856
Alcohol related changes in regulation of NMDA receptor functions.	2008-03	19305787
Pigment epithelium-derived factor protects retinal ganglion cells.	2007-01-29	17261189
Polyamines in the brain: distribution, biological interactions, and their potential therapeutic role in brain ischaemia.	2007	17627518
The sequential analysis of repeated binary responses: a score test for the case of three time points.	2006-07-15	16220479
Adaptation of USP types II and IV controlled release assays for sparingly soluble compounds by direct eluent HPLC analysis.	2006-02	16544912
NMDA/NR2B selective antagonists in the treatment of ischemic brain injury.	2005-04	15857299
Effect of a neuroprotective drug, eliprodil on cardiac repolarisation: importance of the decreased repolarisation reserve in the development of proarrhythmic risk.	2004-09	15302678
Administration of eliprodil during ethanol withdrawal in the neonatal rat attenuates ethanol-induced learning deficits.	2004-09	15064913
Glutamate-dependent regulation of cholinergic phenotype in hypothalamic neurons.	2003-12-19	14663208
Why did NMDA receptor antagonists fail clinical trials for stroke and traumatic brain injury?	2002-10	12849400
Site-selective N-methyl-D-aspartate and alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionate antagonists produce distinct effects in rats performing complex discriminations.	2002-09	12431422
Spermidine attenuates the inhibitory effect of ethanol on NMDA-induced neurotoxicity.	2002-08	12122497
An MCASE approach to the search of a cure for Parkinson's Disease.	2002-04-02	11926966
Glutamate AMPA receptor antagonist treatment for ischaemic stroke.	2002	12365832
NR2B selective NMDA receptor antagonists.	2002	11945135
NMDA antagonists produce site-selective impairment of accuracy in a delayed nonmatch-to-sample task in rats.	2001-12	11747896
The NMDA receptor complex: a promising target for novel antiepileptic strategies.	2001-09	11562266
NMDA receptor antagonists do not block the development of sensitization of catalepsy, but make its expression state-dependent.	2001-04	11396519

Patents

Sample Use Guides

In Vivo Use Guide

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 `Wed Apr 02 07:45:54 GMT 2025` Edited by `admin` on `Wed Apr 02 07:45:54 GMT 2025`
Record UNII	YW62A6TW29
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ELIPRODIL

Official Name

English

(±)-.ALPHA.-(P-CHLOROPHENYL)-4-(P-FLUOROBENZYL)-1-PIPERIDINEETHANOL

Preferred Name

English

eliprodil [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1509