Details of the Drug

General Information of Drug (ID: DMIOGZM)

Drug Name
ELIPRODIL
Synonyms
Eliprodil; 119431-25-3; Eliprodil [INN]; C20H23ClFNO; SL 820715; SL 82-0715; CHEMBL28564; alpha-(4-Chlorophenyl)-4-[(4-fluorophenyl)methyl]-1-piperidineethanol; NCGC00092329-02; 1-Piperidineethanol, alpha-(4-chlorophenyl)-4-(4-fluorophenyl)-, (+-)-; DSSTox_RID_81089; DSSTox_CID_25744; DSSTox_GSID_45744; 1-(4-Chlorophenyl)-2-(4-(4-fluorobenzyl)piperidin-1-yl)ethanol; (+-)-alpha-(p-Chlorophenyl)-4-(p-fluorobenzyl)-1-piperidineethanol; 1-(4-chlorophenyl)-2-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]ethanol
Indication
Disease Entry ICD 11 Status REF
Multiple sclerosis 8A40 Phase 2 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 347.9
Topological Polar Surface Area (xlogp) 4.5
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 3
Chemical Identifiers
Formula
C20H23ClFNO
IUPAC Name
1-(4-chlorophenyl)-2-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]ethanol
Canonical 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
InChIKey
GGUSQTSTQSHJAH-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
60703
ChEBI ID
CHEBI:91784
CAS Number
119431-25-3
DrugBank ID
DB12869
TTD ID
D0S8CI

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Glutamate receptor ionotropic NMDA 1 (NMDAR1) TTLD29N NMDZ1_HUMAN Inhibitor [2]
Glutamate receptor ionotropic NMDA 2B (NMDAR2B) TTN9D8E NMDE2_HUMAN Inhibitor [2]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 ClinicalTrials.gov (NCT00001929) Treatment of Parkinson's Disease With Eliprodil. U.S. National Institutes of Health.
2 4-Hydroxy-1-[2-(4-hydroxyphenoxy)ethyl]-4-(4-methylbenzyl)piperidine: a novel, potent, and selective NR1/2B NMDA receptor antagonist. J Med Chem. 1999 Jul 29;42(15):2993-3000.
3 How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
4 Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5.
5 Synthesis, ionotropic glutamate receptor binding affinity, and structure-activity relationships of a new set of 4,5-dihydro-8-heteroaryl-4-oxo-1,2,... J Med Chem. 2001 Sep 13;44(19):3157-65.
6 4,10-Dihydro-4-oxo-4H-imidazo[1,2-a]indeno[1,2-e]pyrazin-2-carboxylic acid derivatives: highly potent and selective AMPA receptors antagonists with... Bioorg Med Chem Lett. 2000 May 15;10(10):1133-7.
7 Bivalent beta-carbolines as potential multitarget anti-Alzheimer agents. J Med Chem. 2010 May 13;53(9):3611-7.
8 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 455).
9 Amino acid bioisosteres: design of 2-quinolone derivatives as glycine-site N-methyl-D-aspartate receptor antagonists, Bioorg. Med. Chem. Lett. 3(2):299-304 (1993).
10 Synthesis and evaluation of 6,11-ethanohexahydrobenzo[b]quinolizidines: a new class of noncompetitive N-methyl-D-aspartate antagonists. J Med Chem. 1995 Jun 23;38(13):2483-9.
11 Indeno[1,2-b]pyrazin-2,3-diones: a new class of antagonists at the glycine site of the NMDA receptor with potent in vivo activity. J Med Chem. 2000 Jun 15;43(12):2371-81.
12 Synthesis of thieno[2,3-b]pyridinones acting as cytoprotectants and as inhibitors of [3H]glycine binding to the N-methyl-D-aspartate (NMDA) receptor. J Med Chem. 2006 Feb 9;49(3):864-71.
13 NMDA receptor stimulation induces reversible fission of the neuronal endoplasmic reticulum. PLoS One. 2009;4(4):e5250.
14 NMDA receptors as targets for drug action in neuropathic pain. Eur J Pharmacol. 2001 Oct 19;429(1-3):71-8.
15 Inhibition of in vivo [(3)H]MK-801 binding by NMDA receptor open channel blockers and GluN2B antagonists in rats and mice. Eur J Pharmacol. 2015 Nov 5;766:1-8.
16 Emerging drugs in neuropathic pain. Expert Opin Emerg Drugs. 2007 Mar;12(1):113-26.
17 Clinical pipeline report, company report or official report of Cadent Therapeutics.
18 Neu2000, an NR2B-selective, moderate NMDA receptor antagonist and potent spin trapping molecule for stroke. Drug News Perspect. 2010 Nov;23(9):549-56.
19 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
20 Glutamate- and GABA-based CNS therapeutics. Curr Opin Pharmacol. 2006 Feb;6(1):7-17.