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    Chemistry

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    Also known as: 122883-93-6, Ziprasidone hcl, Geodon, Zeldox, 5-(2-(4-(benzo[d]isothiazol-3-yl)piperazin-1-yl)ethyl)-6-chloroindolin-2-one hydrochloride, Ziprasidone (hydrochloride)
    Molecular Formula
    C21H22Cl2N4OS
    Molecular Weight
    449.4  g/mol
    InChI Key
    NZDBKBRIBJLNNT-UHFFFAOYSA-N
    FDA UNII
    JAL53626GG
    Ziprasidone Hydrochloride
    Ziprasidone Hydrochloride is the hydrochloride salt form of ziprasidone, a benzothiazolylpiperazine derivative and an atypical antipsychotic agent with an antischizophrenic property. Ziprasidone hydrochloride 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 hydrochloride also inhibits synaptic reuptake of serotonin and norepinephrine. The mechanism of action by which ziprasidone hydrochloride 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

    Ziprasidone Hydrochloride

    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;hydrochloride
    2.1.2 InChI
    InChI=1S/C21H21ClN4OS.ClH/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;/h1-4,11,13H,5-10,12H2,(H,23,27);1H
    2.1.3 InChI Key
    NZDBKBRIBJLNNT-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1CN(CCN1CCC2=C(C=C3C(=C2)CC(=O)N3)Cl)C4=NSC5=CC=CC=C54.Cl
    2.2 Other Identifiers
    2.2.1 UNII
    JAL53626GG
    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. Geodon

    8. Ziprasidone

    9. Ziprasidone Hydrochloride, Monohydrate

    10. Ziprazidone

    2.3.2 Depositor-Supplied Synonyms

    1. 122883-93-6

    2. Ziprasidone Hcl

    3. Geodon

    4. Zeldox

    5. 5-(2-(4-(benzo[d]isothiazol-3-yl)piperazin-1-yl)ethyl)-6-chloroindolin-2-one Hydrochloride

    6. Ziprasidone (hydrochloride)

    7. 5-[2-[4-(1,2-benzisothiazol-3yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2h-indol-2-one Hydrochloride

    8. Ziprasidone Hydrochloride [usan]

    9. Jal53626gg

    10. 5-[2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2h-indol-2-one Hydrochloride

    11. 5-[2-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]ethyl]-6-chloro-1,3-dihydroindol-2-one Hydrochloride

    12. Cp 88059 (hydrochloride Monohydrate)

    13. 122883-93-6 (hcl)

    14. 2h-indol-2-one, 5-(2-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)ethyl)-6-chloro-1,3-dihydro-, Monohydrochloride

    15. 5-{2-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]ethyl}-6-chloro-2,3-dihydro-1h-indol-2-one Hydrochloride

    16. Cp 88059

    17. Ziprasidone Hydrochloride Hydrate

    18. C21h21cln4os.hcl

    19. Unii-jal53626gg

    20. Ziprasidone, Hcl

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

    22. 2h-indol-2-one, 5-[2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-, Hydrochloride (1:1)

    23. Cp-88059 Hydrochloride

    24. Chembl1712

    25. Mls006010221

    26. Schembl122876

    27. Dtxsid00153762

    28. Hy-14542a

    29. S1444

    30. Akos015848366

    31. Ac-7053

    32. Ccg-220561

    33. Cs-1887

    34. Ks-1219

    35. 5-[2-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]ethyl]-6-chloro-1,3-dihydroindol-2-one;hydrochloride

    36. Ac-26998

    37. Smr002204092

    38. Ziprasidone Hydrochloride Anhydrous

    39. Sw199027-2

    40. Z0032

    41. Ziprasidone Hydrochloride Anhydrous [mi]

    42. 939z277

    43. A890906

    44. Sr-01000759387

    45. Sr-01000759387-2

    46. Ziprasidone Hydrochloride Anhydrous [who-dd]

    47. Q27281411

    48. 5-(2-(4-(benzo[d]isothiazol-3-yl)piperazin-1-yl)ethyl)-6-chloroindolin-2-one Hcl

    49. 5-(2-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)ethyl)-6-chloro-2-indolinone Monohydrochloride

    50. 5-(2-(4-(benzo[d]isothiazol-3-yl)piperazin-1-yl)-ethyl)-6-chloroindolin-2-one Hydrochloride

    51. 5-[2-[4-(1,2-benzisothiazol-3-yl)-1 -piperazinyl]ethyl]-6-chloro-1,3-dihydro-2h-indol- 2-one Hydrochloride

    52. 5-[2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl]-6-chloro-1, 3-dihydro-2h-indol-2-one Hydrochloride

    53. Ziprasidone Hydrochloride Solution, 1.0 Mg/ml In Methanol, Certified Reference Material, Ampule Of 1 Ml

    2.4 Create Date
    2005-08-09
    3 Chemical and Physical Properties
    Molecular Weight 449.4 g/mol
    Molecular Formula C21H22Cl2N4OS
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count4
    Exact Mass448.0891379 g/mol
    Monoisotopic Mass448.0891379 g/mol
    Topological Polar Surface Area76.7 Ų
    Heavy Atom Count29
    Formal Charge0
    Complexity573
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameZiprasidone hydrochloride
    Drug LabelGEODON is available as capsules (ziprasidone hydrochloride) for oral administration and as an injection (ziprasidone mesylate) for intramuscular use only. Ziprasidone is a psychotropic agent that is chemically unrelated to phenothiazine or butyrophen...
    Active IngredientZiprasidone hydrochloride
    Dosage FormCapsule
    RouteOral
    Strengtheq 20mg base; eq 40mg base; eq 80mg base; eq 60mg base
    Market StatusPrescription
    CompanyMylan Pharms; Wockhardt; Apotex; Lupin Pharms; Sandoz; Dr Reddys Labs

    2 of 2  
    Drug NameZiprasidone hydrochloride
    Drug LabelGEODON is available as capsules (ziprasidone hydrochloride) for oral administration and as an injection (ziprasidone mesylate) for intramuscular use only. Ziprasidone is a psychotropic agent that is chemically unrelated to phenothiazine or butyrophen...
    Active IngredientZiprasidone hydrochloride
    Dosage FormCapsule
    RouteOral
    Strengtheq 20mg base; eq 40mg base; eq 80mg base; eq 60mg base
    Market StatusPrescription
    CompanyMylan Pharms; Wockhardt; Apotex; Lupin Pharms; Sandoz; Dr Reddys Labs

    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.)

    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.)

    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.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Atypical Antipsychotic [EPC]

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