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
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
| 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 | ( + / - ) |
DescriptionCurator'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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10235551 | https://www.ncbi.nlm.nih.gov/pubmed/8901012 |
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.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
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
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Eliprodil Approved UseUnknown |
|||
| Primary | Eliprodil Approved UseUnknown |
|||
| Primary | Eliprodil Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 |
|
| 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 |
|
| Effect of a neuroprotective drug, eliprodil on cardiac repolarisation: importance of the decreased repolarisation reserve in the development of proarrhythmic risk. | 2004 Sep |
|
| Administration of eliprodil during ethanol withdrawal in the neonatal rat attenuates ethanol-induced learning deficits. | 2004 Sep |
|
| NMDA/NR2B selective antagonists in the treatment of ischemic brain injury. | 2005 Apr |
|
| Adaptation of USP types II and IV controlled release assays for sparingly soluble compounds by direct eluent HPLC analysis. | 2006 Feb |
|
| The sequential analysis of repeated binary responses: a score test for the case of three time points. | 2006 Jul 15 |
|
| 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
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9371155 https://www.ncbi.nlm.nih.gov/pubmed/8741023 https://books.google.ru/books?id=R5JuLXvuIhgC&pg=PA79&lpg=PA79&dq=Eliprodil+intravenous+for+human&source=bl&ots=lT7H9yACSk&sig=xAjBBvTwjbST3fXJoMHIWkhoy2w&hl=ru&sa=X&ved=0ahUKEwi56rDH3bbUAhVLYVAKHc0DC4AQ6AEIIjAA#v=onepage&q=Eliprodil%20intravenous%20for%20human&f=false https://books.google.ca/books?id=uCYg9KUgZiUC&pg=PA248&lpg=PA248&dq=eliprodil+in+human&source=bl&ots=NfQfJSRiAq&sig=ZBkqsb4uHShWJZd2MD6F3IV_qmI&hl=en&sa=X&ved=0ahUKEwiy1d7PiK_UAhUg8YMKHSxgCiY4ChDoAQgnMAA#v=onepage&q=eliprodil%20in%20human&f=true
Curator's Comment: eliprodil is most often administered intravenously, although it has also been used orally in humans and animals, and as an intraperitoneal injection in animals.
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
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
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| Record UNII |
Y6Q7D9GL4S
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| Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE | |||
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PARENT -> SALT/SOLVATE | |||
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ENANTIOMER -> RACEMATE |
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ACTIVE MOIETY |