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    Xaliproden

    PharmaCompass
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    2D Structure
    Also known as: 135354-02-8, Sr 57746, Xaliproden (usan), V8ql94knqo, Pyridine, 1,2,3,6-tetrahydro-1-(2-(2-naphthalenyl)ethyl)-4-(3-(trifluoromethyl)phenyl)-, Chebi:48520
    Molecular Formula
    C24H22F3N
    Molecular Weight
    381.4  g/mol
    InChI Key
    WJJYZXPHLSLMGE-UHFFFAOYSA-N
    FDA UNII
    V8QL94KNQO
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    1-(2-naphthalen-2-ylethyl)-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2H-pyridine
    2.1.2 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
    2.1.3 InChI Key
    WJJYZXPHLSLMGE-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1CN(CC=C1C2=CC(=CC=C2)C(F)(F)F)CCC3=CC4=CC=CC=C4C=C3
    2.2 Other Identifiers
    2.2.1 UNII
    V8QL94KNQO
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 1-(2-(naphth-2-yl)ethyl)-4-(3-trifluoromethylphenyl)-1,2,5,6-tetrahydropyridine Hydrochloride

    2. 1-(2-(naphth-2-yl)ethyl)-4-(trifluoromethylphenyl)-1,2,5,6-tetrahydropyridine Hydrochloride

    3. Sr 57746a

    4. Sr-57746a

    5. Sr57746a

    6. Xaliproden Hydrochloride

    2.3.2 Depositor-Supplied Synonyms

    1. 135354-02-8

    2. Sr 57746

    3. Xaliproden (usan)

    4. V8ql94knqo

    5. Pyridine, 1,2,3,6-tetrahydro-1-(2-(2-naphthalenyl)ethyl)-4-(3-(trifluoromethyl)phenyl)-

    6. Chebi:48520

    7. 1,2,3,6-tetrahydro-1-(2-(2-naphthyl)ethyl)-4-(alpha,alpha,alpha-trifluoro-m-tolyl)pyridine

    8. Sr-57746

    9. Xaliproden [usan]

    10. 1,2,3,6-tetrahydro-1-(2-(2-naphthalenyl)ethyl)-4-(3-(trifluoromethyl)phenyl)-pyridine

    11. 1-(2-(2-naphthyl)ethyl)-4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine

    12. 1-[2-(2-naphthyl)ethyl]-4-[3-(trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridine

    13. Ncgc00167574-01

    14. Unii-v8ql94knqo

    15. Xaliproden [usan:inn:ban]

    16. 1-[2-(2-naphthyl)ethyl]-4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine

    17. Xaliproden [mi]

    18. Xaliproden [inn]

    19. 1-(2-naphthalen-2-ylethyl)-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine

    20. Xaliproden [who-dd]

    21. Schembl137094

    22. Chembl1512580

    23. Dtxsid9048306

    24. Bdbm82363

    25. Zinc577115

    26. Pdsp1_000054

    27. Pdsp2_000054

    28. Db06393

    29. Sr 57746 A

    30. Ncgc00167574-02

    31. Cas_90494-79-4

    32. Db-063077

    33. Ft-0736660

    34. D06327

    35. L001401

    36. Brd-k88358234-003-01-4

    37. Q12745720

    38. 1-(2-naphthalen-2-ylethyl)-4-[3-(trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridine

    39. 1-[2(naphth-2-yl)ethyl]-4-(3-trifluoromethylphenyl)-1,2,5,6-tetrahydropyridine

    40. 1-[2-(naphth-2-yl)ethyl]-4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 381.4 g/mol
    Molecular Formula C24H22F3N
    XLogP36.2
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count4
    Exact Mass381.17043419 g/mol
    Monoisotopic Mass381.17043419 g/mol
    Topological Polar Surface Area3.2 Ų
    Heavy Atom Count28
    Formal Charge0
    Complexity541
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

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

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Serotonin 5-HT1 Receptor Agonists

    Endogenous compounds and drugs that specifically stimulate SEROTONIN 5-HT1 RECEPTORS. Included under this heading are agonists for one or more of the specific 5-HT1 receptor subtypes. (See all compounds classified as Serotonin 5-HT1 Receptor Agonists.)

    5.2 ATC Code

    N - Nervous system

    N07 - Other nervous system drugs

    N07X - Other nervous system drugs

    N07XX - Other nervous system drugs

    N07XX03 - Xaliproden

    5.3 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.