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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]

API Reference Price

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28-Jun-2024
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