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    Osanetant

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    2D Structure
    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

    2D Structure

    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 Weight 606.6 g/mol
    Molecular Formula C35H41Cl2N3O2
    XLogP37
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count8
    Exact Mass605.2575829 g/mol
    Monoisotopic Mass605.2575829 g/mol
    Topological Polar Surface Area43.9 Ų
    Heavy Atom Count42
    Formal Charge0
    Complexity897
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    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

    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.