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    CHEBI:53757

    ACTIVE PHARMA INGREDIENTS

    PharmaCompass
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    2D Structure
    Also known as: Ziprasidone mesylate, 199191-69-0, Ziprasidone mesilate, Ziprasidone mesylate trihydrate, Ziprasidone mesylate [usan], Ziprasidone mesilate trihydrate
    Molecular Formula
    C22H31ClN4O7S2
    Molecular Weight
    563.1  g/mol
    InChI Key
    WLQZEFFFIUHSJB-UHFFFAOYSA-N
    FDA UNII
    3X6SAX83JZ
    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;trihydrate
    2.1.2 InChI
    InChI=1S/C21H21ClN4OS.CH4O3S.3H2O/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);3*1H2
    2.1.3 InChI Key
    WLQZEFFFIUHSJB-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.O.O.O
    2.2 Other Identifiers
    2.2.1 UNII
    3X6SAX83JZ
    2.3 Synonyms
    2.3.1 MeSH Synonyms

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

    2. Cp 88059

    3. Cp 88059-01

    4. Cp-88,059

    5. Cp-88,059-01

    6. Cp-88,059-1

    7. Ziprasidone

    8. Ziprasidone Hydrochloride

    9. Ziprasidone Hydrochloride, Monohydrate

    10. Ziprazidone

    2.3.2 Depositor-Supplied Synonyms

    1. Ziprasidone Mesylate

    2. 199191-69-0

    3. Ziprasidone Mesilate

    4. Ziprasidone Mesylate Trihydrate

    5. Ziprasidone Mesylate [usan]

    6. Ziprasidone Mesilate Trihydrate

    7. Ziprasidone Mesylate Hydrate

    8. 3x6sax83jz

    9. Ziprasidone (mesylate Hydrate)

    10. Cp-88, 059-27

    11. Nsc-760351

    12. Cp-8805927

    13. Geodon (tn)

    14. Cp-88,059-27

    15. Ziprasidone Mesylate (usan)

    16. 5-[2-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]ethyl]-6-chloro-1,3-dihydroindol-2-one;methanesulfonic Acid;trihydrate

    17. Cp-88059-27

    18. 2h-indol-2-one, 5-(2-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)ethyl)-6-chloro-1,3-dihydro-, Monomethanesulfonate, Trihydrate

    19. 5-(2-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)ethyl)-6-chloro-2-indolinone Monomethanesulfonate, Trihydrate

    20. Unii-3x6sax83jz

    21. Chembl3989833

    22. Chebi:53757

    23. Ziprasidone (mesylate Trihydrate)

    24. Bcp12408

    25. Ziprasidone Mesylate [vandf]

    26. Hy-14542b

    27. Ziprasidone Mesilate [mart.]

    28. Cp88059

    29. Nsc 760351

    30. Bz164581

    31. Ziprasidone Mesylate [orange Book]

    32. D02100

    33. 191z690

    34. A814073

    35. Q27124195

    36. Ziprasidone Mesilate Trihydrate [ep Monograph]

    37. 2h-indol-2-one, 5-(2-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)ethyl)-6-chloro-1,3-dihydro-, Methanesulfonate, Hydrate (1:1:3)

    38. 5-[2-[4-(1,2-benzothiazol-3-yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydroindol-2-one; Methanesulfonic Acid; Trihydrate

    39. 5-[2-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]ethyl]-6-chloranyl-1,3-dihydroindol-2-one; Methanesulfonic Acid; Trihydrate

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 563.1 g/mol
    Molecular Formula C22H31ClN4O7S2
    Hydrogen Bond Donor Count5
    Hydrogen Bond Acceptor Count11
    Rotatable Bond Count4
    Exact Mass562.1322694 g/mol
    Monoisotopic Mass562.1322694 g/mol
    Topological Polar Surface Area143 Ų
    Heavy Atom Count36
    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 Count5
    4 Pharmacology and Biochemistry
    4.1 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.)

    Dopamine Antagonists

    Drugs that bind to but do not activate DOPAMINE RECEPTORS, thereby blocking the actions of dopamine or exogenous agonists. Many drugs used in the treatment of psychotic disorders (ANTIPSYCHOTIC AGENTS) are dopamine antagonists, although their therapeutic effects may be due to long-term adjustments of the brain rather than to the acute effects of blocking dopamine receptors. Dopamine antagonists have been used for several other clinical purposes including as ANTIEMETICS, in the treatment of Tourette syndrome, and for hiccup. Dopamine receptor blockade is associated with NEUROLEPTIC MALIGNANT SYNDROME. (See all compounds classified as Dopamine Antagonists.)

    Serotonin Antagonists

    Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or SEROTONIN RECEPTOR AGONISTS. (See all compounds classified as Serotonin Antagonists.)

    4.2 FDA Pharmacological Classification
    4.2.1 Pharmacological Classes
    Atypical Antipsychotic [EPC]