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Xaliproden

Xaliproden

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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

Xaliproden

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 Formula	C₂₄H₂₂F₃N
Molecular Weight	381.4 g/mol
XLogP3	6.2
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	4
Exact Mass	381.17043419 g/mol
Monoisotopic Mass	381.17043419 g/mol
Topological Polar Surface Area	3.2 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	541
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.