Eliprodil
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MedKoo CAT#: 317118

CAS#: 119431-25-3

Description: Eliprodil, aslo known as SL-82,0715; is a NMDA antagonist. NMDA receptors are a key component in mediating glutamate-induced excitotoxicity, and it is believed that NMDA antagonists would be neuroprotective after a stroke or other traumatic brain injury. Eliprodil protects pyramidal neurons in hippocampal slices from hypoxic/ischemic damage. Eliprodil stimulates CNS myelination, may be a new prospect for multiple sclerosis.


Chemical Structure

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Eliprodil
CAS# 119431-25-3

Theoretical Analysis

MedKoo Cat#: 317118
Name: Eliprodil
CAS#: 119431-25-3
Chemical Formula: C20H23ClFNO
Exact Mass: 347.14522
Molecular Weight: 347.86
Elemental Analysis: C, 69.06; H, 6.66; Cl, 10.19; F, 5.46; N, 4.03; O, 4.60

Price and Availability

Size Price Availability Quantity
10.0mg USD 110.0 2 weeks
25.0mg USD 150.0 2 weeks
50.0mg USD 250.0 2 weeks
100.0mg USD 450.0 2 weeks
200.0mg USD 750.0 2 weeks
500.0mg USD 1250.0 2 weeks
1.0g USD 1950.0 2 weeks
2.0g USD 2950.0 2 weeks
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Synonym: SL-82,0715; SL82,0715; SL 82,0715; SL-820715; SL820715; SL 820715; Eliprodil.

IUPAC/Chemical Name: 1-(4-chlorophenyl)-2-(4-(4-fluorobenzyl)piperidin-1-yl)ethan-1-ol

InChi Key: GGUSQTSTQSHJAH-UHFFFAOYSA-N

InChi Code: 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

SMILES Code: OC(C1=CC=C(Cl)C=C1)CN2CCC(CC3=CC=C(F)C=C3)CC2

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 347.86 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Lengyel C, Dézsi L, Biliczki P, Horváth C, Virág L, Iost N, Németh M, Tálosi L, Papp JG, Varró A. Effect of a neuroprotective drug, eliprodil on cardiac repolarisation: importance of the decreased repolarisation reserve in the development of proarrhythmic risk. Br J Pharmacol. 2004 Sep;143(1):152-8. Epub 2004 Aug 9. PubMed PMID: 15302678; PubMed Central PMCID: PMC1575264.

2: Thomas JD, Garcia GG, Dominguez HD, Riley EP. Administration of eliprodil during ethanol withdrawal in the neonatal rat attenuates ethanol-induced learning deficits. Psychopharmacology (Berl). 2004 Sep;175(2):189-95. Epub 2004 Apr 3. PubMed PMID: 15064913.

3: Pabel J, Höfner G, Wanner KT. Synthesis and resolution of racemic eliprodil and evaluation of the enantiomers of eliprodil as NMDA receptor antagonists. Bioorg Med Chem Lett. 2000 Jun 19;10(12):1377-80. PubMed PMID: 10890168.

4: Kapin MA, Doshi R, Scatton B, DeSantis LM, Chandler ML. Neuroprotective effects of eliprodil in retinal excitotoxicity and ischemia. Invest Ophthalmol Vis Sci. 1999 May;40(6):1177-82. PubMed PMID: 10235551.

5: Pang IH, Wexler EM, Nawy S, DeSantis L, Kapin MA. Protection by eliprodil against excitotoxicity in cultured rat retinal ganglion cells. Invest Ophthalmol Vis Sci. 1999 May;40(6):1170-6. PubMed PMID: 10235550.

6: Wlaź P, Ebert U, Löscher W. Anticonvulsant effects of eliprodil alone or combined with the glycineB receptor antagonist L-701,324 or the competitive NMDA antagonist CGP 40116 in the amygdala kindling model in rats. Neuropharmacology. 1999 Feb;38(2):243-51. PubMed PMID: 10218865.

7: Demerens C, Stankoff B, Zalc B, Lubetzki C. Eliprodil stimulates CNS myelination: new prospects for multiple sclerosis? Neurology. 1999 Jan 15;52(2):346-50. PubMed PMID: 9932955.

8: Sukhotina I, Dravolina O, Bespalov A. Place conditioning of mice with the NMDA receptor antagonists, eliprodil and dizocilpine. Eur J Pharmacol. 1998 Dec 4;362(2-3):103-10. PubMed PMID: 9874159.

9: Ibarrola D, Seegers H, Jaillard A, Hommel M, Décorps M, Massarelli R. The effect of eliprodil on the evolution of a focal cerebral ischaemia in vivo. Eur J Pharmacol. 1998 Jul 3;352(1):29-35. PubMed PMID: 9718264.

10: Hogg S, Perron C, Barnéoud P, Sanger DJ, Moser PC. Neuroprotective effect of eliprodil: attenuation of a conditioned freezing deficit induced by traumatic injury of the right parietal cortex in the rat. J Neurotrauma. 1998 Jul;15(7):545-53. PubMed PMID: 9674557.

11: Reyes M, Reyes A, Opitz T, Kapin MA, Stanton PK. Eliprodil, a non-competitive, NR2B-selective NMDA antagonist, protects pyramidal neurons in hippocampal slices from hypoxic/ischemic damage. Brain Res. 1998 Jan 26;782(1-2):212-8. PubMed PMID: 9519265.

12: Lekieffre D, Benavides J, Scatton B, Nowicki JP. Neuroprotection afforded by a combination of eliprodil and a thrombolytic agent, rt-PA, in a rat thromboembolic stroke model. Brain Res. 1997 Nov 21;776(1-2):88-95. PubMed PMID: 9439799.

13: Santamaria R, Françon D, Depoortere H, Scatton B. Neuroprotective effects of eliprodil in a rat hippocampal slice hypoxia model. Ann N Y Acad Sci. 1997 Oct 15;825:232-8. PubMed PMID: 9369990.

14: Leibrock J, Prücher H, Rautenberg W. EMD 95885, a new eliprodil analogue with higher affinity for the N-methyl-D-aspartate (NMDA) receptor. Pharmazie. 1997 Jun;52(6):479-80. PubMed PMID: 9260271.

15: Biton B, Godet D, Granger P, Avenet P. R- and L-type Ca2+ channels are insensitive to eliprodil in rat cultured cerebellar granule neurons. Eur J Pharmacol. 1997 Apr 4;323(2-3):277-81. PubMed PMID: 9128850.

16: Avenet P, Léonardon J, Besnard F, Graham D, Depoortere H, Scatton B. Antagonist properties of eliprodil and other NMDA receptor antagonists at rat NR1A/NR2A and NR1A/NR2B receptors expressed in Xenopus oocytes. Neurosci Lett. 1997 Feb 21;223(2):133-6. PubMed PMID: 9089691.

17: Nankai M, Klarica M, Fage D, Carter C. Evidence for native NMDA receptor subtype pharmacology as revealed by differential effects on the NMDA-evoked release of striatal neuromodulators: eliprodil, ifenprodil and other native NMDA receptor subtype selective compounds. Neurochem Int. 1996 Nov;29(5):529-42. PubMed PMID: 8939463.

18: Wang S, Yang Q, Moller CJ, Sharp FR, Haglid KG. Eliprodil prevents expression of the 70 kDa heat shock protein in MK801-injured neurones. Pharmacol Toxicol. 1996 Sep;79(3):166-8. PubMed PMID: 8884877.

19: Malavasi B, Ripamonti M, Rouchouse A, Ascalone V. Stereoselective determination of unchanged and glucuroconjugated eliprodil, a new anti-ischaemic drug, in human plasma and urine by precolumn derivatization and column-switching high-performance liquid chromatography with fluorescence detection. J Chromatogr A. 1996 Apr 5;729(1-2):323-33. PubMed PMID: 9004957.

20: Bath CP, Farrell LN, Gilmore J, Ward MA, Hicks CA, O'Neill MJ, Bleakman D. The effects of ifenprodil and eliprodil on voltage-dependent Ca2+ channels and in gerbil global cerebral ischaemia. Eur J Pharmacol. 1996 Mar 28;299(1-3):103-12. PubMed PMID: 8901012.