Eliprodil

Eliprodil
Clinical data

ATC code	None
Identifiers
IUPAC name 1-(4-Chlorophenyl)-2-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]ethanol
CAS Number	119431-25-3^N
PubChem (CID)	60703
ChemSpider	54708^Y
UNII	YW62A6TW29^Y
ChEMBL	CHEMBL28564^Y
ECHA InfoCard	100.162.249
Chemical and physical data
Formula	C₂₀H₂₃ClFNO
Molar mass	347.854 g/mol
3D model (Jmol)	Interactive image
SMILES C1CN(CCC1CC2=CC=C(C=C2)F)CC(C3=CC=C(C=C3)Cl)O
InChI 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^Y Key:GGUSQTSTQSHJAH-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

Eliprodil (codenamed SL-82.0715) is a NMDA antagonist drug candidate that failed a Phase III clinical trial for the treatment of acute ischemic stroke in 1996, sponsored by Synthélabo Recherche.^[1]^[2]^[3]

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.^[4] After a traumatic brain injury, neurons become deprived of glucose and oxygen. These neurons quickly lose ATP and become depolarized, which releases glutamate. The intracellular buildup of glutamate triggers the overstimulation of AMPA and NMDA receptors. This, in turn, causes an influx of Na⁺ and Ca²⁺. Therefore, when NMDA receptors are activated, there is an increase in intracellular Ca²⁺ concentration. High Ca²⁺ causes fatal metabolic consequences, including neuronal cell death.^[3]

References

↑ The Pharma Letter. 2 December 1996 Synthelabo's Eliprodil Fails In Stroke Trials
↑ DeKeyser J, Sulter G, & Luiten PG (1999) Clinical trials with neuroprotective drugs in acute ischaemic stroke: are we doing the right thing? Trends in neurosciences 22(12):535-540 PMID 10542428
1 2 Lee JM, Zipfel GJ, & Choi DW (1999) The changing landscape of ischaemic brain injury mechanisms. Nature 399(6738 Suppl):A7-14 PMID 10392575
↑ Ikonomidou C & Turski L (2002) Why did NMDA receptor antagonists fail clinical trials for stroke and traumatic brain injury? The Lancet. Neurology 1(6):383-386 PMID 12849400

Glutamatergics

Receptor
(ligands)

AMPA	Agonists: Glutamate/active site agonists: 5-Fluorowillardiine Acromelic acid (acromelate) AMPA BOAA Domoic acid Glutamate Ibotenic acid Proline Quisqualic acid Willardiine; Positive allosteric modulators: Aniracetam Cyclothiazide CX-516 CX-546 CX-614 Farampator (CX-691, Org 24448) CX-717 CX-1739 CX-1942 Diazoxide Hydrochlorothiazide (HCTZ) IDRA-21 LY-392,098 LY-404,187 LY-451,646 LY-503,430 Mibampator (LY-451,395) Org 26576 Oxiracetam PEPA PF-04958242 Piracetam Pramiracetam S-18986 Sunifiram Unifiram Antagonists: ACEA-1011 ATPO Becampanel Caroverine CNQX Dasolampanel DNQX Fanapanel (MPQX) GAMS GYKI-52466 Kynurenic acid Kynurenine Licostinel (ACEA-1021) NBQX PNQX Selurampanel Tezampanel Theanine Topiramate YM90K Zonampanel; Negative allosteric modulators: Barbiturates (e.g., pentobarbital, sodium thiopental) Cyclopropane Enflurane Ethanol Evans blue GYKI-53,655 Halothane Irampanel Isoflurane Perampanel Pregnenolone sulfate Talampanel

NMDA	Agonists: Glutamate/active site agonists: AMAA Aspartate Glutamate Homocysteic acid (L-HCA) Homoquinolinic acid Ibotenic acid NMDA Proline Quinolinic acid Tetrazolylglycine Theanine; Glycine site agonists: β-Fluoro-D-alanine ACBD ACC (ACPC) ACPD AK-51 Apimostinel (NRX-1074) B6B21 CCG D-Alanine D-Cycloserine D-Serine DHPG Dimethylglycine Glycine HA-966 L-687,414 L-Alanine L-Serine Milacemide Neboglamine (nebostinel) Rapastinel (GLYX-13) Sarcosine; Polyamine site agonists: Spermidine Spermine; Other positive allosteric modulators: 24S-Hydroxycholesterol DHEA DHEA sulfate Pregnenolone sulfate SAGE-718 Antagonists: Competitive antagonists: AP5 (APV) AP7 CGP-37849 CGP-39551 CGP-39653 CGP-40116 CGS-19755 CPP LY-233,053 LY-235,959 LY-274,614 MDL-100,453 Midafotel (d-CPPene) NPC-12,626 NPC-17,742 PBPD PEAQX Perzinfotel PPDA SDZ-220581 Selfotel; Noncompetitive antagonists: ARR-15,896 Caroverine Dexanabinol FPL-12495 FR-115,427 Hodgkinsine Magnesium MDL-27,266 NPS-1506 Psychotridine Zinc; Uncompetitive pore blockers: 2-MDP 3-HO-PCP 3-MeO-PCE 3-MeO-PCMo 3-MeO-PCP 4-MeO-PCP 8A-PDHQ 18-MC α-Endopsychosin Alaproclate Amantadine Aptiganel Arketamine ARL-12,495 ARL-15,896-AR ARL-16,247 Budipine Conaridine Delucemine Dexoxadrol Dextrallorphan Dieticyclidine Diphenidine Dizocilpine Ephenidine Esketamine Etoxadrol Eticyclidine Fluorolintane Gacyclidine Ibogaine Ibogamine Indantadol Ketamine Ketobemidone Lanicemine Loperamide Memantine Methadone (Levomethadone) Methorphan (Dextromethorphan Levomethorphan) Methoxetamine Methoxphenidine Milnacipran Morphanol (Dextrorphan Levorphanol) NEFA Neramexane Nitromemantine Nitrous oxide Noribogaine Norketamine Orphenadrine PCPr Pethidine (meperidine) Phencyclamine Phencyclidine Propoxyphene Remacemide Rhynchophylline Rimantadine Rolicyclidine Sabeluzole Tabernanthine Tenocyclidine Tiletamine Tramadol Xenon; Glycine site antagonists: 4-Cl-KYN (AV-101) 5,7-DCKA 7-CKA ACC ACEA-1011 ACEA-1328 AV-101 Carisoprodol CGP-39653 CNQX DNQX Felbamate Gavestinel GV-196,771 Kynurenic acid Kynurenine L-689,560 L-701,324 Licostinel (ACEA-1021) LU-73,068 MDL-105,519 Meprobamate MRZ 2/576 PNQX ZD-9379; NR2B subunit antagonists: Besonprodil CERC-301 (MK-0657) CO-101,244 (PD-174,494) Eliprodil Haloperidol Ifenprodil Isoxsuprine Nylidrin Ro8-4304 Ro25-6981 Traxoprodil; Polyamine site antagonists: Arcaine Co 101676 Diaminopropane Diethylenetriamine Huperzine A Putrescine Ro 25-6981; Unclassified/unsorted antagonists: Bumetanide Chloroform Cyclopropane D-αAA Diethyl ether Enflurane Ethanol Flufenamic acid Flupirtine Furosemide Halothane Isoflurane Metaphit Methoxyflurane Niflumic acid Pentamidine isethionate Piretanide Toluene Transcrocetin (saffron) Trichloroethane Trichloroethanol Trichloroethylene Xylene

Kainate	Agonists: Glutamate/active site agonists: 5-Bromowillardiine 5-Iodowillardiine Acromelic acid (acromelate) AMPA ATPA Domoic acid Glutamate Ibotenic acid Kainic acid LY-339,434 Proline Quisqualic acid SYM-2081; Positive allosteric modulators: Cyclothiazide Diazoxide Enflurane Halothane Isoflurane Antagonists: ACEA-1011 CNQX Dasolampanel DNQX GAMS Kynurenic acid Licostinel (ACEA-1021) LY-382,884 NBQX NS102 Selurampanel Tezampanel Theanine Topiramate UBP-302; Negative allosteric modulators: Barbiturates (e.g., pentobarbital, sodium thiopental) Enflurane Ethanol Evans blue NS-3763 Pregnenolone sulfate

mGlu₁	Agonists: ACPD DHPG Glutamate Ibotenic acid Quisqualic acid Ro01-6128 Ro67-4853 Ro67-7476 VU-71 Antagonists: BAY 36-7620 CPCCOEt Cyclothiazide LY-367,385 LY-456,236 MCPG NPS-2390

mGlu₂	Agonists: BINA CBiPES DCG-IV Eglumegad Glutamate Ibotenic acid LY-379,268 LY-404,039 (pomaglumetad) LY-487,379 LY-566,332 MGS-0028 Pomaglumetad methionil (LY-2140023) Talaglumetad; Positive allosteric modulators: JNJ-40411813 (ADX-71149) Antagonists: APICA CECXG EGLU HYDIA LY-307,452 LY-341,495 MCPG MGS-0039 PCCG-4; Negative allosteric modulators: Decoglurant RO4491533

mGlu₃	Agonists: CBiPES DCG-IV Eglumegad Glutamate Ibotenic acid LY-379,268 LY-404,039 (pomaglumetad) LY-487,379 MGS-0028 Pomaglumetad methionil (LY-2140023) Talaglumetad Antagonists: APICA CECXG EGLU HYDIA LY-307,452 LY-341,495 MCPG MGS-0039; Negative allosteric modulators: Decoglurant RO4491533

mGlu₄	Agonists: Glutamate L-AP4 PHCCC VU-001,171 VU-0155,041; Positive allosteric modulators: MPEP Antagonists: CPPG MAP4 MPPG MSOP MTPG UBP-1112

mGlu₅	Agonists: ACPD ADX-47273 CDPPB CHPG DFB DHPG Glutamate Ibotenic acid Quisqualic acid VU-1545 Antagonists: CTEP DMeOB LY-344,545 Mavoglurant MCPG NPS-2390 Remeglurant SIB-1757 SIB-1893; Negative allosteric modulators: Basimglurant Dipraglurant Fenobam GRN-529 MPEP MTEP Raseglurant

mGlu₆	Agonists: Glutamate L-AP4 Antagonists: CPPG MAP4 MPPG MSOP MTPG UBP-1112

mGlu₇	Agonists: AMN082 Glutamate L-AP4 Antagonists: CPPG MAP4 MMPIP MPPG MSOP MTPG UBP-1112

mGlu₈	Agonists: DCPG Glutamate L-AP4 Antagonists: CPPG MAP4 MPPG MSOP MTPG UBP-1112

Transporter
(blockers)

EAATs	Amphetamine Aspartic acid (aspartate) cis-ACBD DHKA Glutamic acid (glutamate) HIP-A HIP-B Kainic acid L-(-)-threo-3-Hydroxyaspartic acid L-αAA L-CCG-III ((2S,3S,4R)-CCG) L-Serine-O-sulphate (SOS) L-trans-2,4-PDC MPDC SYM-2081 TBOA TFB-TBOA Theanine threo-3-Methylglutamic acid UCPH-101 WAY-213,613

vGluTs	4-Methylene-L-glutamate 6-(4'-Phenylstyryl)-QDC 6-Biphenyl-4-yl-QDC 7-CKA Acid red 114 Amido black 10B (naphthol blue black) Bafilomycin A1 Benzopurpurin 4B Bumetamide Chicago sky blue 6B Aspartic acid (aspartate) DIDS Direct blue 71 Erythro-4-methyl-L-glutamic acid Evans blue Furosemide Glutamic acid (glutamate) Kynurenic acid Nigericin NPPB (N144) Ponceau SS Reactive blue 2 Rose bengal SITS trans-ACDP Trypan blue Valinomycin Xanthurenic acid

Enzyme
(inhibitors)

GAH	BPTES CB-839 DON

AST	2-Amino-3-butenoic acid AAOA AMB β-DL-Methylene-aspartate Hydrazinosuccinate

ALT	β-Chloro-L-alanine L-Cycloserine Propargylglycine

GDH	AAOA Bithionol Chloroquine EGCG GTP GW5074 Hexachlorophene Hydroxylamine Palmitoyl-CoA Pyridoxal phosphate

GS	2-Aminoadipic acid JFD01307SC Methionine sulfoximine Phosphinothricin (glufosinate)

GAD	3-Mercaptopropionic acid AAOA L-Allylglycine Semicarbazide

Others

Precursors: GHB
L-Glutamine

Prodrugs: Aceglutamide (to L-glutamine)

See also: GABAergics • GHBergics • Glycinergics

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