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E2031

Eliprodil

Name: Eliprodil
Brand: SIGMA

≥98% (HPLC), powder

Synonym(s):

α-(4-Chlorophenyl)-4-[(4-fluorophenyl)methyl]-1-piperidineethanol, SL 820715

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About This Item

Empirical Formula (Hill Notation):

C₂₀H₂₃ClFNO

CAS Number:

119431-25-3

Molecular Weight:

347.85

NACRES:

NA.77

PubChem Substance ID:

24277709

UNSPSC Code:

12352200

MDL number:

MFCD00866651

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

200

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Quality Level

200

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL, clear, H₂O: insoluble

originator

Sanofi Aventis

storage temp.

2-8°C

SMILES string

OC(CN1CCC(CC1)Cc2ccc(F)cc2)c3ccc(Cl)cc3

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

InChI key

GGUSQTSTQSHJAH-UHFFFAOYSA-N

Gene Information

human ... GRIN2B(2904)
rat ... Adra1a(29412)

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Biochem/physiol Actions

NR2B selective NMDA glutamate receptor antagonist which appears to target the "polyamine site" on the NMDA receptor, setting it apart from other NR2B receptor antagonists. Possesses neuroprotective effects in models of ischemia, but prolongs the QT interval in patients; currently under investigation for acute and chronic pain.

NR2B selective NMDA glutamate receptor antagonist.

Features and Benefits

This compound was developed by Sanofi Aventis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves

Regulatory Information

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Human retina contains polyamine sensitive [3H]-ifenprodil binding sites: implications for neuroprotection?

N A Sharif et al.

The British journal of ophthalmology, 83(2), 236-240 (1999-07-09)

This study characterised the pharmacology of [3H]-ifenprodil binding to the polyamine binding sites (PBS) on the N-methyl-D-aspartate (NMDA) receptor channel complex on human retinas. These data were correlated with the known neuroprotective effects of ifenprodil and eliprodil. Specific binding of

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.

P Wlaź et al.

Neuropharmacology, 38(2), 243-251 (1999-04-28)

The discovery that glutamate's activity at the N-methyl-D-aspartate (NMDA) receptor is positively modulated by glycine and polyamines has led to a new pharmacological strategy that NMDA receptor-mediated events could be antagonized indirectly at the strychnine-insensitive glycine co-agonist site (glycine(B) receptor)

Adaptation of USP types II and IV controlled release assays for sparingly soluble compounds by direct eluent HPLC analysis.

P J Missel et al.

Pharmaceutical development and technology, 11(1), 87-91 (2006-03-21)

Measurement of drug release of a sparingly soluble drug by conventional methods proceeds very slowly without the aid of surfactants. Two preliminary automated methods were developed that increase sensitivity and accelerate such studies by working at very small reservoir volumes.

Decrement in operant performance produced by NMDA receptor antagonists in the rat: tolerance and cross-tolerance.

O A Dravolina et al.

Pharmacology, biochemistry, and behavior, 65(4), 611-620 (2000-04-15)

Current perspectives on the clinical use of NMDA receptor antagonists infer repeated administration schedules for the management of different pathological states. The development of tolerance and cross-tolerance between different NMDA receptor antagonists may be an important factor contributing to the

Administration of eliprodil during ethanol withdrawal in the neonatal rat attenuates ethanol-induced learning deficits.

J D Thomas et al.

Psychopharmacology, 175(2), 189-195 (2004-04-06)

Prenatal exposure to alcohol can disrupt brain development, leading to a variety of behavioral alterations, including learning deficits. We have postulated that some central nervous system damage may be due to N-methyl-D-aspartate (NMDA) receptor-mediated excitotoxicity that occurs during ethanol withdrawal.

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Global Trade Item Number

SKU	GTIN
E2031-10MG	04061832090627
E2031-50MG	04061832090634

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