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    Ziprasidone Mesylate

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    2D Structure
    Also known as: 185021-64-1, Ziprasidone mesylate anhydrous, Vcy3f61s5r, 2h-indol-2-one, 5-(2-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)ethyl)-6-chloro-1,3-dihydro-, monomethanesulfonate, 5-[2-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]ethyl]-6-chloro-1,3-dihydroindol-2-one;methanesulfonic acid, Unii-vcy3f61s5r
    Molecular Formula
    C22H25ClN4O4S2
    Molecular Weight
    509.0  g/mol
    InChI Key
    LOQSYPGSAZUDJZ-UHFFFAOYSA-N
    FDA UNII
    VCY3F61S5R
    Ziprasidone Mesylate is the mesylate salt form of ziprasidone, a benzothiazolylpiperazine derivative and an atypical antipsychotic agent with an antischizophrenic property. Ziprasidone mesylate functions as an antagonist at the dopamine D2 and serotonin 5-HT2A and 5-HT1D receptors, and as an agonist at the 5-HT1A receptor. Ziprasidone mesylate also inhibits the synaptic reuptake of serotonin and norepinephrine. The mechanism of action by which ziprasidone mesylate exerts its antischizophrenic effect is unknown but is potentially mediated through a combination of dopamine D2 and serotonin 5-HT2 antagonism. This agent also has antagonistic activity against histamine H1 and alpha-1-adrenergic receptors.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    5-[2-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]ethyl]-6-chloro-1,3-dihydroindol-2-one;methanesulfonic acid
    2.1.2 InChI
    InChI=1S/C21H21ClN4OS.CH4O3S/c22-17-13-18-15(12-20(27)23-18)11-14(17)5-6-25-7-9-26(10-8-25)21-16-3-1-2-4-19(16)28-24-21;1-5(2,3)4/h1-4,11,13H,5-10,12H2,(H,23,27);1H3,(H,2,3,4)
    2.1.3 InChI Key
    LOQSYPGSAZUDJZ-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CS(=O)(=O)O.C1CN(CCN1CCC2=C(C=C3C(=C2)CC(=O)N3)Cl)C4=NSC5=CC=CC=C54
    2.2 Other Identifiers
    2.2.1 UNII
    VCY3F61S5R
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. 185021-64-1

    2. Ziprasidone Mesylate Anhydrous

    3. Vcy3f61s5r

    4. 2h-indol-2-one, 5-(2-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)ethyl)-6-chloro-1,3-dihydro-, Monomethanesulfonate

    5. 5-[2-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]ethyl]-6-chloro-1,3-dihydroindol-2-one;methanesulfonic Acid

    6. Unii-vcy3f61s5r

    7. Cp-88059-27

    8. Ziprasidone (mesylate)

    9. Schembl957247

    10. Chembl1200997

    11. Dtxsid80939920

    12. Hms3264b21

    13. Pharmakon1600-01503850

    14. Hy-14542c

    15. Nsc760351

    16. Ziprasidone Mesilate [who-dd]

    17. Akos015900335

    18. Ccg-213218

    19. Ac-23355

    20. Q27291762

    21. 2h-indol-2-one, 5-(2-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)ethyl)-6-chloro-1,3-dihydro-, Methanesulfonate (1:1)

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 509.0 g/mol
    Molecular Formula C22H25ClN4O4S2
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count4
    Exact Mass508.1005753 g/mol
    Monoisotopic Mass508.1005753 g/mol
    Topological Polar Surface Area140 Ų
    Heavy Atom Count33
    Formal Charge0
    Complexity665
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Pharmacology and Biochemistry
    4.1 FDA Pharmacological Classification
    4.1.1 Pharmacological Classes
    Atypical Antipsychotic [EPC]