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    Chemistry

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    Also known as: 913611-97-9, Opc-34712, Rexulti, 7-(4-(4-(benzo[b]thiophen-4-yl)piperazin-1-yl)butoxy)quinolin-2(1h)-one, Opc 34712, 2j3ybm1k8c
    Molecular Formula
    C25H27N3O2S
    Molecular Weight
    433.6  g/mol
    InChI Key
    ZKIAIYBUSXZPLP-UHFFFAOYSA-N
    FDA UNII
    2J3YBM1K8C
    Brexpiprazole
    Brexpiprazole is a novel D2 dopamine and serotonin 1A partial agonist, called serotonin-dopamine activity modulator (SDAM), and a potent antagonist of serotonin 2A receptors, noradrenergic alpha 1B and 2C receptors. Brexpiprazole is approved for the treatment of schizophrenia, and as an adjunctive treatment for major depressive disorder (MDD). Although it failed Phase II clinical trials for ADHD, it has been designed to provide improved efficacy and tolerability (e.g., less akathisia, restlessness and/or insomnia) over established adjunctive treatments for major depressive disorder (MDD).
    Brexpiprazole is an Atypical Antipsychotic.
    1 2D Structure

    Brexpiprazole

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    7-[4-[4-(1-benzothiophen-4-yl)piperazin-1-yl]butoxy]-1H-quinolin-2-one
    2.1.2 InChI
    InChI=1S/C25H27N3O2S/c29-25-9-7-19-6-8-20(18-22(19)26-25)30-16-2-1-11-27-12-14-28(15-13-27)23-4-3-5-24-21(23)10-17-31-24/h3-10,17-18H,1-2,11-16H2,(H,26,29)
    2.1.3 InChI Key
    ZKIAIYBUSXZPLP-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1CN(CCN1CCCCOC2=CC3=C(C=C2)C=CC(=O)N3)C4=C5C=CSC5=CC=C4
    2.2 Other Identifiers
    2.2.1 UNII
    2J3YBM1K8C
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 7-(4-(4-(1-benzothiophen-4-yl)piperazin-1-yl)butoxy)quinolin-2(1h)-one

    2. Rexulti

    2.3.2 Depositor-Supplied Synonyms

    1. 913611-97-9

    2. Opc-34712

    3. Rexulti

    4. 7-(4-(4-(benzo[b]thiophen-4-yl)piperazin-1-yl)butoxy)quinolin-2(1h)-one

    5. Opc 34712

    6. 2j3ybm1k8c

    7. 7-(4-(4-(1-benzothiophen-4-yl)piperazin-1-yl)butoxy)quinolin-2(1h)-one

    8. 7-[4-[4-(1-benzothiophen-4-yl)piperazin-1-yl]butoxy]-1h-quinolin-2-one

    9. Brexpiprazole [usan]

    10. Unii-2j3ybm1k8c

    11. Brexpiprazole [usan:inn]

    12. Rxulti

    13. Rexulti (tn)

    14. Brexpiprazole.2h2o

    15. Brexpiprazole-[d8]

    16. Brexpiprazole [mi]

    17. Brexpiprazole [inn]

    18. Brexpiprazole [jan]

    19. Brexpiprazole(opc34712)

    20. Brexpiprazole; Opc-34712

    21. Brexpiprazole [who-dd]

    22. Gtpl7672

    23. Schembl1037592

    24. Brexpiprazole (jan/usan/inn)

    25. Chembl2105760

    26. Schembl14772509

    27. Amy6914

    28. Dtxsid40238527

    29. Chebi:134716

    30. Hms3885p12

    31. Brexpiprazole [orange Book]

    32. Bcp10218

    33. Bcp24077

    34. Ex-a2639

    35. Opc34712

    36. Mfcd27987920

    37. S4639

    38. Zinc84758479

    39. Akos025291100

    40. Akos037515802

    41. Ccg-269055

    42. Db09128

    43. Sb16735

    44. Ncgc00378574-01

    45. Ncgc00378574-02

    46. Ac-30404

    47. As-56467

    48. Da-35913

    49. Hy-15780

    50. Ft-0712292

    51. A13527

    52. D10309

    53. Q2924764

    54. 2(1h)-quinolinone, 7-(4-(4-benzo(b)thien-4-yl-1-piperazinyl)butoxy)-

    55. 7-[4-(4-benzo[b]thien-4-yl-1-piperazinyl)butoxy]- 2(1h)-quinolinone

    56. 7-[4-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)-butoxy]-1h-quinolin-2-one

    57. 7-[4-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)butoxy]-1h-quinolin-2-one

    58. 7-[4-(4-benzo[b]thiophen-4-ylpiperazin-1-yl)butoxy]-1h-quinolin-2-one

    2.4 Create Date
    2007-01-03
    3 Chemical and Physical Properties
    Molecular Weight 433.6 g/mol
    Molecular Formula C25H27N3O2S
    XLogP34.7
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count7
    Exact Mass433.18239829 g/mol
    Monoisotopic Mass433.18239829 g/mol
    Topological Polar Surface Area73 Ų
    Heavy Atom Count31
    Formal Charge0
    Complexity636
    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

    As an adjunctive treatment of major depressive disorder (MDD) and for treatment of schizophrenia.

    FDA Label

    Treatment of schizophrenia.

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Dopamine Agonists

    Drugs that bind to and activate dopamine receptors. (See all compounds classified as Dopamine Agonists.)

    Serotonin Agents

    Drugs used for their effects on serotonergic systems. Among these are drugs that affect serotonin receptors, the life cycle of serotonin, and the survival of serotonergic neurons. (See all compounds classified as Serotonin Agents.)

    5.2 FDA Pharmacological Classification
    5.2.1 Active Moiety
    BREXPIPRAZOLE
    5.2.2 FDA UNII
    2J3YBM1K8C
    5.2.3 Pharmacological Classes
    Atypical Antipsychotic [EPC]
    5.3 ATC Code

    N05AX16

    N - Nervous system

    N05 - Psycholeptics

    N05A - Antipsychotics

    N05AX - Other antipsychotics

    N05AX16 - Brexpiprazole

    5.4 Absorption, Distribution and Excretion

    Absorption

    Brexpiprazole reaches peak plasma concentration within 4 hours of administration, and steady state occurs within 10-12 days of dosing. Oral bioavailability is 95%, and can be administered with or without food.

    Route of Elimination

    Approximately 25% urinary and 46% fecal excretion. <1% and ~14% of the unchanged drug was recovered in the urine and feces, respectively.

    Volume of Distribution

    Intravenous volume of distribution is 1.56L/kg.

    Clearance

    19.8mL/h/kg

    5.5 Metabolism/Metabolites

    Metabolized mainly by CYP3A4 and CYP2D6 enzymes into its major metabolite, DM-3411. DM-3411 is not considered to contribute any therapeutic effect.

    5.6 Biological Half-Life

    Brexpiprazole and its major metabolite, DM-3411 have half lives of 91 and 96 hours respectively.

    5.7 Mechanism of Action

    Although the mechanism of action of brexpiprazole in the treatment of MDD and schizophrenia is unclear, the efficacy of brexpiprazole may be attributed to partial agonist activity at serotonin 1A and dopamine D2 receptors, and antagonist activity at serotonin 2A receptors.

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    19-Jan-2021
    20-Aug-2024
    KGS
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