Eliprodil
Basic information
- CAS
119431-25-3- Standard SMILES
OC(CN1CCC(Cc2ccc(F)cc2)CC1)c1ccc(Cl)cc1- InChIKey
GGUSQTSTQSHJAH-UHFFFAOYSA-N- Molecular formula
- C20H23ClFNO
- Average molar mass
- 347.9 g/mol
- Monoisotopic mass
- 347.1452202
Overview
Eliprodil is a racemate comprising equimolar amounts of (R)- and (S)-eliprodil. It is a non-competitive N-methyl-D-aspartate (NMDA) receptor antagonist and an anti-ischaemic agent that exhibits neuroprotective properties. It has a role as a geroprotector, a calcium channel blocker, a NMDA receptor antagonist and a neuroprotective agent. It contains a (R)-eliprodil and a (S)-eliprodil.
Names & identifiers
- Preferred name
- Eliprodil
- IUPAC
- 1-(4-chlorophenyl)-2-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]ethanol
- English name
- Eliprodil
- Molecular formula
- C20H23ClFNO
- Molecular weight
- 347.85
Names & synonyms
Eliprodil119431-25-3DTXSID1045744SL-820715YW62A6TW29DTXCID9025744CHEBI:917841-Piperidineethanol, alpha-(4-chlorophenyl)-4-(4-fluorophenyl)-, (+-)-1-(4-chlorophenyl)-2-{4-[(4-fluorophenyl)methyl]piperidin-1-yl}ethan-1-oleliprodilumSL 82.07151-(4-chlorophenyl)-2-(4-((4-fluorophenyl)methyl)piperidin-1-yl)ethan-1-ol
Show more names
SL 820715Eliprodil, 10 mM in DMSO1-(4-broMophenyl)-2-(4-(4-fluorobenzyl)piperidin-1-yl)ethanolα-(4-chlorophenyl)-4-[(4-fluorophenyl)methyl]-1-piperidineethanol(+-)-alpha-(p-Chlorophenyl)-4-(p-fluorobenzyl)-1-piperidineethanol1-Piperidineethanol, α-(4-chlorophenyl)-4-[(4-fluorophenyl)methyl]-SL 820715, α-(4-Chlorophenyl)-4-[(4-fluorophenyl)methyl]-1-piperidineethanol
1-(4-chlorophenyl)-2-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]ethan-1-ol(4-chlorophenyl)-4-((4-fluorophenyl)methyl)-1-piperidineethanolRefChem:590714Eliprodil [INN]1-(4-chlorophenyl)-2-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]ethanol1-(4-chlorophenyl)-2-(4-(4-fluorobenzyl)piperidin-1-yl)ethan-1-olalpha-(4-Chlorophenyl)-4-[(4-fluorophenyl)methyl]-1-piperidineethanolSL 82-0715
Properties
Computed structural properties
- XLogP
- 4.5
- Topological polar surface area
- 23.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 5
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 359
Physicochemical properties
- Boiling point
- 474.1 · 474.1±35.0 °C(Predicted)
- Density
- 1.205 · 1.205±0.06 g/cm3(Predicted)
- storage temp.
- 2 · Sealed in dry,2-8°C
- solubility
- 17 mg/mL · DMSO: ~17 mg/mL
- form
- solid
- pka
- 13.99 · 13.99±0.20(Predicted)
- color
- white
- 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
- InChIKey
- GGUSQTSTQSHJAH-UHFFFAOYSA-N
- SMILES
- OC(CN1CCC(CC1)Cc2ccc(F)cc2)c3ccc(Cl)cc3
- FDA UNII
- 62 A6TW29 · YW62A6TW29
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07,GHS09
- Signal word
- Warning
- Hazard statements
- 319 · H319-H410
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
P264+P265, P273, P280, P305+P351+P338, P337+P317, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesEye Irrit. 2 (100%)
Safety data
- PPE
- Eyeshields, Gloves
- wgk
- 3
- ridadr
- UN 3077 9/PG 3
- risk_code
- 50/53
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS09
- hazard_code
- N
- safety_code
- 60-61
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H319-H410
- Precautionary statements
- P273-P305+P351+P338-P501
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Drugs that bind to but do not activate excitatory amino acid receptors, thereby blocking the actions of agonists.
Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids.
Applications
DescriptionN-Methyl-D-aspartate (NMDA) receptors are calcium permeable ligand-gated channels of the central nervous system that are activated after binding of the co-agonists glutamate and glycine. Eliprodil is a non-competitive NMDA receptor antagonist that inhibits neuronal calcium channel currents. It is selective for NR2B subunit-containing receptors (IC50 = 1 μM), displaying greater than 100-fold selectivity for NR2B over NR2A and NR2C subunits. Eliprodil also avidly binds σ1 and σ2 sites (Kis = 0.013 and 0.63 μM, respectively). It is effective in vivo, blocking ischemia-induced neurodegeneration in the CA1 region of the hippocampus of gerbils subjected to bilateral carotid artery occlusion. Eliprodil can also have proarrhythmic actions in hearts under normal conditions.
UsesEliprodil is a noncardiac drug with neuroprotective properties. It is also a N-Methyl-D-aspartate receptor (NMDAR) antagonist.
Additional notes
DefinitionChEBI: Eliprodil is a racemate comprising equimolar amounts of (R)- and (S)-eliprodil. It is a non-competitive N-methyl-D-aspartate (NMDA) receptor antagonist and an anti-ischaemic agent that exhibits neuroprotective properties. It has a role as a geroprotector, a NMDA receptor antagonist, a neuroprotective agent and a calcium channel blocker. It contains a (R)-eliprodil and a (S)-eliprodil.
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