NAV

Xaliproden

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Xaliproden
DrugBank Accession Number
DB06393
Background

Not Available

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 381.442
Monoisotopic: 381.170434201
Chemical Formula
C24H22F3N
Synonyms
  • Xaliproden
External IDs
  • SR 57746
  • SR 57746A
  • SR-57746
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Pharmacology

Indication

Investigated for use/treatment in amyotrophic lateral sclerosis (ALS) and alzheimer's disease.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

Xaliproden is an orally-active, synthetic, non-peptidic 5-hydroxytryptamine (5-HT) 1A receptor agonist with neurotrophic and neuroprotective activities. Although its mechanism of action is not fully understood, xaliproden appears to either mimic the effects of neurotrophins or stimulate their synthesis, thereby stimulating neuronal cell differentiation and proliferation and inhibiting neuronal cell death. The neuroprotective effect of this agent involves the activation of MAP kinase pathways via stimulation of the 5-HT1A receptor.

TargetActionsOrganism
U5-hydroxytryptamine receptor 1ANot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Xaliproden Hydrochloride44D5EE8E2690494-79-4WVHBEIJGAINUBW-UHFFFAOYSA-N

Categories

ATC Codes
N07XX03 — Xaliproden
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Naphthalenes
Sub Class
Not Available
Direct Parent
Naphthalenes
Alternative Parents
Trifluoromethylbenzenes / Phenethylamines / Aralkylamines / Hydropyridines / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Organofluorides / Hydrocarbon derivatives / Alkyl fluorides
Substituents
Alkyl fluoride / Alkyl halide / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Hydrocarbon derivative / Hydropyridine / Monocyclic benzene moiety / Naphthalene
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tertiary amino compound, ring assembly, naphthalenes, tetrahydropyridine, (trifluoromethyl)benzenes (CHEBI:48520)
Affected organisms
Not Available

Chemical Identifiers

UNII
V8QL94KNQO
CAS number
135354-02-8
InChI Key
WJJYZXPHLSLMGE-UHFFFAOYSA-N
InChI
InChI=1S/C24H22F3N/c25-24(26,27)23-7-3-6-22(17-23)20-11-14-28(15-12-20)13-10-18-8-9-19-4-1-2-5-21(19)16-18/h1-9,11,16-17H,10,12-15H2
IUPAC Name
1-[2-(naphthalen-2-yl)ethyl]-4-[3-(trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridine
SMILES
FC(F)(F)C1=CC(=CC=C1)C1=CCN(CCC2=CC3=CC=CC=C3C=C2)CC1

References

General References
Not Available
KEGG Drug
D06327
ChemSpider
114237
BindingDB
82363
ChEBI
48520
ChEMBL
CHEMBL1512580
ZINC
ZINC000000577115
Wikipedia
Xaliproden

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedPreventionColorectal Carcinoma (CRC) / Colorectal Neoplasms / Metastatic Cancer2
3CompletedTreatmentAlzheimer's Disease (AD)2
3TerminatedTreatmentColorectal Neoplasms1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000229 mg/mLALOGPS
logP6.26ALOGPS
logP6.23Chemaxon
logS-6.2ALOGPS
pKa (Strongest Basic)8.96Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count1Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area3.24 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity109.26 m3·mol-1Chemaxon
Polarizability41.17 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0009000000-48db2ffa376aa8d42b1e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0029000000-e3eb22210fe8600b1cc8
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0209000000-30c3d32276433e4e5964
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0029000000-0986c2e512f58627f682
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a59-0911000000-6e36fb851f3246349c23
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a6u-0932000000-e67b63476b55a71ce631
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-187.79176
predicted
DeepCCS 1.0 (2019)
[M+H]+190.14977
predicted
DeepCCS 1.0 (2019)
[M+Na]+197.07289
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. 5-hydroxytryptamine receptor 1A
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers...
Gene Name
HTR1A
Uniprot ID
P08908
Uniprot Name
5-hydroxytryptamine receptor 1A
Molecular Weight
46106.335 Da

Drug created at March 19, 2008 16:28 / Updated at February 21, 2021 18:52