Ziprasidone hydrochloride

Base Information

• Chemical Name: Ziprasidone hydrochloride
• CAS No.: 122883-93-6
• Molecular Formula: C₂₁H₂₁ClN₄OS
• Molecular Weight: 412.943
• European Community (EC) Number: 602-903-0
• UNII: JAL53626GG
• DSSTox Substance ID: DTXSID00153762
• Wikidata: Q27281411
• NCI Thesaurus Code: C48031
• RXCUI: 1294533
• Pharos Ligand ID: 4P3RKTZ5ANZ8
• ChEMBL ID: CHEMBL1712
• Mol file: 122883-93-6.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 hydrochloride

Chemical Property:

• Melting Point: >300 °C
• Boiling Point: 554.8 °C at 760 mmHg
• Flash Point: 289.3 °C
• PSA: 76.71000
• LogP: 4.75190
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 448.0891379
• Heavy Atom Count: 29
• Complexity: 573

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-(2-(4-(Benzo[d]isothiazol-3-yl)piperazin-1-yl)-ethyl)-6-chloroindolin-2-one hydrochloride 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCN1CCC2=C(C=C3C(=C2)CC(=O)N3)Cl)C4=NSC5=CC=CC=C54.Cl
• Recent ClinicalTrials: A Six-week Flexible Dose Study Evaluating the Efficacy and Safety of Geodon in Patients With Bipolar I Depression.
• Recent EU Clinical Trials: Pharmacovigilance in children and adolescents:
• Description: Both p.o. and i.m. formulations of ziprasidone were launched in Sweden for the treatment of schizophrenia and agitated psychoses. It is the sixth marketed atypical antipsychotic after clozapine, risperidone, olanzapine, sertindole and quetiapine. The synthesis of ziprasidone involves a novel one-step process for the preparation of 3-(1- piperazinyl)-1,2-benzisothiazole followed by coupling with a chlorooxindole fragment. Ziprasidone is a very potent 5-HT2A/D2 antagonist with a ratio of about 11 in favor of the serotonin receptor. It also shows very high 5-HT2c antagonistic activity, high 5-HT1A agonistic and 5-HT1D antagonistic activity, as well as moderate antagonism of α1 and H1 receptors and moderate norepinephrine and serotonin reuptake inhibition. Its complex binding profile for serotonin and dopamine receptors resulted during clinical trials in high antipsychotic efficacy with low extrapyramidal side effects and also in antidepressive action with low propensity for weight gain in opposition to other atypical and typical neuroleptics. An intramuscular formulation of ziprasidone was demonstrated to be superior to haloperidol, a conventional neuroleptic, for the short-term treatment of agitation in acutely psychotic patients. When administered orally in the fed state, this well-tolerated agent which strongly binds to plasma proteins shows a bioavailability of about 60% which is almost 2 fold greater than in the fasted state. It is transformed into 4 circulating major metabolites by different enzyme systems. The small QTc prolongation observed with ziprasidone was found to be comparable to other antipsychotic drugs and it is considered to be without significant risk.
• Uses: Ziprasidone (Geodon, Zeldox) was the fifth atypical antipsychotic to gain FDA approval. In the United States, Ziprasidone is approved for the treatment of schizophrenia, and the intramuscular injection form of ziprasidone is approved for acute agitation i
• Therapeutic Function: H-Indol-2-one, 5-(2-(4-(1,2-benzisothiazol-3-yl)-1- piperazinyl)ethyl)-6-chloro-1,3-dihydro-, monohydrochloride monohydrate

Technology Process of Ziprasidone hydrochloride

There total 33 articles about Ziprasidone hydrochloride 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

Dihydroziprasidone

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

Refernces

• 1、 -. "A key intermediate for the preparation of ziprasidone". Paragraph 0131-0134. . Retrieved 2018/04/03.
• 2、 -. "Process for the Preparation of Ziprasidone". Page/Page column 5. . Retrieved 2011/01/12.