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CHEBI:53757

CHEBI:53757

Synopsis, Chemistry

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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

CHEBI:53757

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 Formula	C₂₂H₃₁ClN₄O₇S₂
Molecular Weight	563.1 g/mol
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	4
Exact Mass	562.1322694 g/mol
Monoisotopic Mass	562.1322694 g/mol
Topological Polar Surface Area	143 Å²
Heavy Atom Count	36
Formal Charge	0
Complexity	665
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	5

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]