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
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
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 | ( + / - ) |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/12849400Curator'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
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
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) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9519265 |
13.0 nM [Ki] | ||
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 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Eliprodil Approved UseUnknown |
|||
Primary | Eliprodil Approved UseUnknown |
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Primary | Eliprodil Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
NMDA receptor antagonists do not block the development of sensitization of catalepsy, but make its expression state-dependent. | 2001 Apr |
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Effect of a neuroprotective drug, eliprodil on cardiac repolarisation: importance of the decreased repolarisation reserve in the development of proarrhythmic risk. | 2004 Sep |
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NMDA/NR2B selective antagonists in the treatment of ischemic brain injury. | 2005 Apr |
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Adaptation of USP types II and IV controlled release assays for sparingly soluble compounds by direct eluent HPLC analysis. | 2006 Feb |
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The sequential analysis of repeated binary responses: a score test for the case of three time points. | 2006 Jul 15 |
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Alcohol related changes in regulation of NMDA receptor functions. | 2008 Mar |
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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 |
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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 |
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Antidepressants are a rational complementary therapy for the treatment of Alzheimer's disease. | 2010 Mar 12 |
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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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8788420
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
Edited
Sat Dec 16 16:22:04 GMT 2023
by
admin
on
Sat Dec 16 16:22:04 GMT 2023
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Record UNII |
YW62A6TW29
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Record Status |
Validated (UNII)
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Record Version |
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C1509
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C058083
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |