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    Chemistry

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    Also known as: Asenapine maleate, 85650-56-2, Asenapine (maleate), Sycrest, Asenapine maleate [usan], Org 5222
    Molecular Formula
    C21H20ClNO5
    Molecular Weight
    401.8  g/mol
    InChI Key
    GMDCDXMAFMEDAG-CHHFXETESA-N
    FDA UNII
    CU9463U2E2
    Asenapine Maleate
    1 2D Structure

    Asenapine Maleate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (Z)-but-2-enedioic acid;(2S,6S)-9-chloro-4-methyl-13-oxa-4-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),7(12),8,10,14,16-hexaene
    2.1.2 InChI
    InChI=1S/C17H16ClNO.C4H4O4/c1-19-9-14-12-4-2-3-5-16(12)20-17-7-6-11(18)8-13(17)15(14)10-19;5-3(6)1-2-4(7)8/h2-8,14-15H,9-10H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t14-,15-;/m1./s1
    2.1.3 InChI Key
    GMDCDXMAFMEDAG-CHHFXETESA-N
    2.1.4 Canonical SMILES
    CN1CC2C(C1)C3=C(C=CC(=C3)Cl)OC4=CC=CC=C24.C(=CC(=O)O)C(=O)O
    2.1.5 Isomeric SMILES
    CN1C[C@H]2[C@H](C1)C3=C(C=CC(=C3)Cl)OC4=CC=CC=C24.C(=C\C(=O)O)\C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    CU9463U2E2
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 5-chloro-2,3,3a,12b-tetrahydro-2-methyl-1h-dibenz(2,3-6,7)oxepino(4,5-c)pyrrole

    2. Asenapine

    3. Asenapine Maleate

    4. Org 5222

    5. Org-5222

    6. Secuado

    7. Trans-5-chloro-2,3,3a,12b-tetrahydro-2-methyl-1h-dibenz(2,3:6,7)oxepino(4,5-c)pyrrole

    2.3.2 Depositor-Supplied Synonyms

    1. Asenapine Maleate

    2. 85650-56-2

    3. Asenapine (maleate)

    4. Sycrest

    5. Asenapine Maleate [usan]

    6. Org 5222

    7. Org-5222

    8. Cu9463u2e2

    9. (z)-but-2-enedioic Acid;(2s,6s)-9-chloro-4-methyl-13-oxa-4-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),7(12),8,10,14,16-hexaene

    10. 1h-dibenz[2,3:6,7]oxepino[4,5-c]pyrrole, 5-chloro-2,3,3a,12b-tetrahydro-2-methyl-, Trans-, (z)-2-butenedioate (1:1)

    11. Trans-5-chloro-2-methyl-2,3,3a,12b-tetrahydro-1h-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole Maleate

    12. Asenapine (as Maleate)

    13. (3ars,12brs)-5-chloro-2-methyl-2,3,3a,12b-tetrahydro-1h-dibenzo(2,3:6,7)oxepino(4,5-c)pyrrole (2z)-2-butenedioate (1:1)

    14. 1h-dibenz(2,3:6,7)oxepino(4,5-c)pyrrole, 5-chloro-2,3,3a,12b-tetrahydro-2-methyl-, (3ar,12br)-rel-, (2z)-2-butenedioate (1:1)

    15. Trans-5-chloro-2,3,3a,12b-tetrahydro-2-methyl-1h-dibenz(2,3:6,7)oxepino(4,5-c)pyrrole Maleate

    16. Unii-cu9463u2e2

    17. Einecs 288-064-8

    18. Saphris (tn)

    19. Org 5222 Maleate

    20. Asenapine Maleate Solution

    21. (s,s)-asenapine Maleate

    22. Schembl175228

    23. Asenapine Maleate [mi]

    24. Asenapine Maleate (jan/usan)

    25. Asenapine Maleate [jan]

    26. Chebi:71248

    27. Asenapine Maleate [mart.]

    28. Dtxsid301017360

    29. Hms3884e09

    30. Asenapine Maleate [who-dd]

    31. Asenapine Maleate [ema Epar]

    32. Asenapine Maleate, >=98% (hplc)

    33. Mfcd00900588

    34. S1283

    35. Akos015951084

    36. Asenapine Maleate [orange Book]

    37. Ccg-268667

    38. Cs-0859

    39. Mk-8274

    40. Sch-900274

    41. Ac-24116

    42. Hy-11100

    43. Sw219879-1

    44. D02995

    45. 650a562

    46. Q27139467

    47. 65576-45-6, 135883-08-8 (maleic Acid)

    48. Asenapine Maleate 1.0 Mg/ml In Methanol (as Free Base)

    49. (3as,12bs)-5-chloro-2,3,3a,12b-tetrahydro-2-methyl-1h-dibenz[2,3:6,7]oxepino[4,5-c]pyrrole Maleate

    50. 1h-dibenz(2,3:6,7)oxepino(4,5-c)pyrrole, 5-chloro-2,3,3a,12b-tetrahydro-2-methyl-,(3ar,12br)-rel-, (2z)-2-butenedioate (1:1)

    51. Trans-5-chloro-2,3,3a,12b-tetrahydro-2-methyl-1h-dibenzo[2,3;6,7]-oxepino[4,5-c]pyrrole Maleate

    52. Trans-5-chloro-2-methyl-2,3,3a,12b-tetrahydro-1h-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrolemaleate

    2.4 Create Date
    2006-07-28
    3 Chemical and Physical Properties
    Molecular Weight 401.8 g/mol
    Molecular Formula C21H20ClNO5
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count2
    Exact Mass401.1030004 g/mol
    Monoisotopic Mass401.1030004 g/mol
    Topological Polar Surface Area87.1 Ų
    Heavy Atom Count28
    Formal Charge0
    Complexity482
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameSaphris
    PubMed HealthAsenapine (By mouth)
    Drug ClassesAntipsychotic
    Drug LabelSAPHRIS is a psychotropic agent that is available for sublingual administration. Asenapine belongs to the class dibenzo-oxepino pyrroles. The chemical designation is (3aRS,12bRS)-5-Chloro-2-methyl-2,3,3a,12b-tetrahydro-1Hdibenzo[2,3:6,7]oxepino[4,5-c...
    Active IngredientAsenapine maleate
    Dosage FormTablet
    RouteSublingual
    Strengtheq 5mg base; eq 10mg base
    Market StatusPrescription
    CompanyForest Labs

    2 of 2  
    Drug NameSaphris
    PubMed HealthAsenapine (By mouth)
    Drug ClassesAntipsychotic
    Drug LabelSAPHRIS is a psychotropic agent that is available for sublingual administration. Asenapine belongs to the class dibenzo-oxepino pyrroles. The chemical designation is (3aRS,12bRS)-5-Chloro-2-methyl-2,3,3a,12b-tetrahydro-1Hdibenzo[2,3:6,7]oxepino[4,5-c...
    Active IngredientAsenapine maleate
    Dosage FormTablet
    RouteSublingual
    Strengtheq 5mg base; eq 10mg base
    Market StatusPrescription
    CompanyForest Labs

    4.2 Drug Indication

    Sycrest is indicated for the treatment of moderate to severe manic episodes associated with bipolar I disorder in adults.

    Treatment of bipolar I disorder

    5 Pharmacology and Biochemistry
    5.1 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.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Atypical Antipsychotic [EPC]
    5.3 ATC Code

    N05AH05

    API Reference Price

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    19-Apr-2021
    04-Aug-2022
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