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Osanetant

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Chemistry

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Also known as: 160492-56-8, Osanetant [inn], Sr142801, Sr-142801, Sb-236984, Sr-14280

Molecular Formula

C₃₅H₄₁Cl₂N₃O₂

Molecular Weight

606.6 g/mol

InChI Key

DZOJBGLFWINFBF-UMSFTDKQSA-N

FDA UNII

K7G81N94DT

Developed by Sanofi-Aventis (formerly Sanofi-Synthelabo), osanetant (SR-142801) is an NK3 receptor antagonist which was under development for the treatment of schizophrenia and other Central Nervous System (CNS) disorders. In a review of its R&D portfolio, the company announced in August 2005 that it would cease any further development of osanetant. This follows an earlier decision to discontinue development of eplivanserin for schizophrenia.

1 2D Structure

Osanetant

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-[1-[3-[(3R)-1-benzoyl-3-(3,4-dichlorophenyl)piperidin-3-yl]propyl]-4-phenylpiperidin-4-yl]-N-methylacetamide

2.1.2 InChI

InChI=1S/C35H41Cl2N3O2/c1-27(41)38(2)35(29-13-7-4-8-14-29)19-23-39(24-20-35)21-9-17-34(30-15-16-31(36)32(37)25-30)18-10-22-40(26-34)33(42)28-11-5-3-6-12-28/h3-8,11-16,25H,9-10,17-24,26H2,1-2H3/t34-/m0/s1

2.1.3 InChI Key

DZOJBGLFWINFBF-UMSFTDKQSA-N

2.1.4 Canonical SMILES

CC(=O)N(C)C1(CCN(CC1)CCCC2(CCCN(C2)C(=O)C3=CC=CC=C3)C4=CC(=C(C=C4)Cl)Cl)C5=CC=CC=C5

2.1.5 Isomeric SMILES

CC(=O)N(C)C1(CCN(CC1)CCC[C@@]2(CCCN(C2)C(=O)C3=CC=CC=C3)C4=CC(=C(C=C4)Cl)Cl)C5=CC=CC=C5

2.2 Other Identifiers

2.2.1 UNII

K7G81N94DT

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (s)-(n)-(1-(3-(1-benzoyl-3-(3,4-dichlorophenyl)piperidin-3-yl)propyl)-4-phenylpiperidin-4-yl)-n-methylacetamide

2. Sr 142801

3. Sr 142806

4. Sr-142801

5. Sr142801

2.3.2 Depositor-Supplied Synonyms

1. 160492-56-8

2. Osanetant [inn]

3. Sr142801

4. Sr-142801

5. Sb-236984

6. Sr-14280

7. Sr-142806

8. Chembl346178

9. K7g81n94dt

10. N-(1-(3-((r)-1-benzoyl-3-(3,4-dichlorophenyl)-3-piperidyl)propyl)-4-phenyl-4-piperidyl)-n-methylacetamide

11. N-(1-(3-((3r)-1-benzoyl-3-(3,4-dichlorophenyl)-3-piperidinyl)propyl)-4-phenyl-4-piperidinyl)-n-methylacetamide

12. Sr 142801

13. [3h]osanetant

14. (r)-n-(1-(3-(1-benzoyl-3-(3,4-dichlorophenyl)piperidin-3-yl)propyl)-4-phenylpiperidin-4-yl)-n-methylacetamide

15. Acetamide, N-[1-[3-[(3r)-1-benzoyl-3-(3,4-dichlorophenyl)-3-piperidinyl]propyl]-4-phenyl-4-piperidinyl]-n-methyl-

16. N-(1-{3-[(r)-1-benzoyl-3-(3,4-dichloro-phenyl)-piperidin-3-yl]-propyl}-4-phenyl-piperidin-4-yl)-n-methyl-acetamide

17. Sr 142806

18. Unii-k7g81n94dt

19. N-[1-[3-[(3r)-1-(benzoyl)-3-(3,4-dichlorophenyl)piperidin-3-yl]propyl]-4-phenylpiperidin-4-yl]-n-methylacetamide

20. N-[1-[3-[(3r)-1-benzoyl-3-(3,4-dichlorophenyl)-3-piperidinyl]propyl]-4-phenyl-4-piperidinyl]-n-methylacetamide

21. [3h]sr142801

22. [3h]sr142,801

23. Mls006010325

24. N-[1-[3-[(3r)-1-benzoyl-3-(3,4-dichlorophenyl)piperidin-3-yl]propyl]-4-phenylpiperidin-4-yl]-n-methylacetamide

25. Schembl119440

26. Gtpl2110

27. Gtpl3480

28. Dtxsid901027521

29. Zinc3935475

30. Bdbm50291261

31. Pdsp1_001495

32. Pdsp2_001479

33. Akos015895948

34. Bcp9001032

35. Db04872

36. Ncgc00263110-01

37. Ncgc00263110-02

38. (s)-(n)-(1-(3-(1-benzoyl-3-(3,4-dichlorophenyl)piperidin-3-yl)propyl)-4-phenylpiperidin-4-yl)-n-methylacetamide

39. Acetamide, N-(1-(3-(1-benzoyl-3-(3,4-dichlorophenyl)-3-piperidinyl)propyl)-4-phenyl-4-piperidinyl)-n-methyl-, (r)-

40. Hy-14551

41. Smr004701389

42. Cs-0003438

43. Sr 142,806

44. Sr-142,801

45. E98685

46. Q7105703

47. Brd-k15646852-001-01-5

48. (s)-(+)-n-((3-[1-benzoyl-3-(3,4-dichlorophenyl)piperidin-3-yl]prop-1-yl)-4-phenylpiperidin-4-yl)-n-methylacetamine

2.4 Create Date

2005-08-09

3 Chemical and Physical Properties

Molecular Formula	C₃₅H₄₁Cl₂N₃O₂
Molecular Weight	606.6 g/mol
XLogP3	7
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	8
Exact Mass	605.2575829 g/mol
Monoisotopic Mass	605.2575829 g/mol
Topological Polar Surface Area	43.9 Å²
Heavy Atom Count	42
Formal Charge	0
Complexity	897
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
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

Potential therapy for schizophrenia, depression and visceral pain.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Osanetant is a neurokinin-3 (NK3) receptor antagonist. Preliminary clinical trials have demonstrated that osanetant is superior to placebo on global assessment of efficacy and measures of positive symptoms in schizophrenia.

5.2 MeSH Pharmacological Classification

Antipsychotic Agents

Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus. (See all compounds classified as Antipsychotic Agents.)

5.3 Mechanism of Action

The mechanism of action of osanetant is uncertain at this point. Various preclinical data indicate that activation of NK3 receptors enhances the release of biogenic amines, including dopamine and serotonin. NK3 receptor antagonists could block NK3-receptor-mediated activation of these systems.

Drugs in Development