Ziprasidone

Base Information

• Chemical Name: Ziprasidone
• CAS No.: 146939-27-7
• Molecular Formula: C₂₁H₂₁ClN₄OS
• Molecular Weight: 412.943
• Hs Code.: 29211980
• European Community (EC) Number: 928-541-6,638-809-1
• UNII: 6UKA5VEJ6X
• DSSTox Substance ID: DTXSID4023753
• Nikkaji Number: J553.147K
• Wikipedia: Ziprasidone
• Wikidata: Q205517
• NCI Thesaurus Code: C47788,C48031,C48032
• RXCUI: 115698,353116,1294533
• Pharos Ligand ID: 4P3RKTZ5ANZ8
• Metabolomics Workbench ID: 42647
• ChEMBL ID: CHEMBL708
• Mol file: 146939-27-7.mol

Synonyms:5-(2-(4-(3-benzisothiazolyl)piperazinyl)ethyl)-6-chloro-1,3-dihydro-2H-indol-2-one;CP 88059;CP 88059-01;CP-88,059;CP-88,059-01;CP-88,059-1;Geodon;ziprasidone;ziprasidone hydrochloride;ziprasidone hydrochloride, monohydrate;ziprazidone

Chemical Property of Ziprasidone

Chemical Property:

• Appearance/Colour: tan solid
• Melting Point: 213-215 °C
• Refractive Index: 1.681
• Boiling Point: 554.819 °C at 760 mmHg
• PKA: 13.34±0.20(Predicted)
• Flash Point: 289.344 °C
• PSA: 76.71000
• Density: 1.37 g/cm³
• LogP: 3.94990
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 412.1124602
• Heavy Atom Count: 28
• Complexity: 573

Purity/Quality:

99.9% ^*data from raw suppliers

Ziprasidone-d8 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,T
• Hazard Codes: F,T
• Statements: 60-61-11-19-38
• Safety Statements: 53-45

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antipsychotic Agents
• Canonical SMILES: C1CN(CCN1CCC2=C(C=C3C(=C2)CC(=O)N3)Cl)C4=NSC5=CC=CC=C54
• Recent ClinicalTrials: Ziprasidone in the Psychosis Prodrome
• Recent EU Clinical Trials: Cognitive effects of adjuntive Vortioxetine in early Schizophrenia
• Recent NIPH Clinical Trials: ME2112 Phase III (ME2112-2)
• Uses: It is a kind of antipsychotic and can be used as the antagonist of the dopamine D2-serotonin 5-HT2. Labelled Ziprasidone, which is used as an antipsychotic. Combined serotonin (5HT2) and dopamine (D2) receptor antagonist. Labeled Ziprasidone, intended for use as an internal standard for the quantification of Ziprasidone by GC- or LC-mass spectrometry.
• Production method: 6-Chloro-1,3-dihydro-2H-indol-2-ketone (I) and bromoacetic acid can have acylation reaction under the action of polyphosphoric acid to give the compound (II). And then be stirred together with silicon hydride and triethyl trifluoroacetic acid at room temperature to give the compound (III). Finally, it can have reaction with N-(3-benzisothiazole-yl) piperazine in MIBK containing sodium carbonate to give the product.
• Biological Functions: "Ziprasidone is chemically similar to risperidone but with a substitution of piperzinyl and benzisothiazole for piperidinyl and benzisoxazole and with minor aromatic modification. Like risperidone, ziprasidone is a high-affinity antagonist at 5-HT2A/C and D2 receptors as well as at adrenergic α1/α2 and histamine H1 receptors. Moreover, ziprasidone can activate 5-HT1A receptors that regulate dopaminergic neurotransmission in brain regions involved in critical cognitive functions. Thus, in addition to D2 partial agonism, 5-HT1A agonism is now thought to be an important pharmacological property for atypical antipsychotic drug efficacy.

Technology Process of Ziprasidone

There total 33 articles about Ziprasidone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.9%

5-(2-bromoethyl)-6-chloro-1,3-dihydrooxindole + 3-(1-piperazinyl)-1,2-benzisothiazole (87691-87-0) → ziprazidone (122883-93-6,199191-69-0,146939-27-7)

Guidance literature:

With sodium carbonate; In water; acetonitrile; Solvent; Reagent/catalyst; Inert atmosphere; Reflux;

Reference yield: 92.0%

3-(1-piperazinyl)-1,2-benzisothiazole (87691-87-0) + 6-chloro-5-(2-chloroethyl)-2-oxindole (118289-55-7) → ziprazidone (122883-93-6,199191-69-0,146939-27-7)

Guidance literature:

With Morwet D₄₂₅; In water; Reflux; Inert atmosphere;

Reference yield: 92.0%

3-(piperazin-1-yl)-1,2-benzisothiazole hydrochloride (133070-64-1,144010-02-6) + 6-chloro-5-(2-chloroethyl)-2-oxindole (118289-55-7) → ziprazidone (122883-93-6,199191-69-0,146939-27-7)

Guidance literature:

With Morwet D₄₂₅; In water; Product distribution / selectivity; Reflux; Inert atmosphere;

upstream raw materials:

5-(2-(4-(7-bromo-1,2-benzisothiazol-3-yl)piperazinyl)-ethyl)-6-chloro-1,3-dihydro-2H-indol-2-one

3-(1-piperazinyl)-1,2-benzisothiazole

6-chloro-5-(2-chloroethyl)-2-oxindole

methyl 5-{2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl}-4-chloro-2-nitrophenyl acetate

Downstream raw materials:

Ziprasidone sulfoxide

5-{2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]-ethyl}-6-chloro-1,3-dihydro-2H-indol-2-one hydrobromide monohydrate

Refernces

• 1、 -. "Purification method and preparation method for ziprasidone mesilate". Paragraph 0033-0051. . Retrieved 2018/07/30.
• 2、 -. "A SHORT PROCESS FOR THE PREPARATION OF ZIPRASIDONE AND INTERMEDIATES THEREOF". . . Retrieved 2012/03/09.