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Home > Encyclopedia > Ziprasidone hydrochloride

Ziprasidone hydrochloride

Ziprasidone hydrochloride structure

Ziprasidone hydrochloride 

structure
  • CAS No:

    122883-93-6

  • Formula:

    C21H21ClN4OS.ClH

  • Chemical Name:

    Ziprasidone hydrochloride

  • Synonyms:

    2H-Indol-2-one,5-[2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-,hydrochloride (1:1);2H-Indol-2-one,5-[2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-,monohydrochloride;CP 88059-1;Ziprasidone hydrochloride;5-[2-[4-(1,2-Benzisothiazol-3-yl)-1-piperazinyl)ethyl]-6-chloro-1,3-dihydro-2H-indol-2-one hydrochloride;Zeldox;Zipsydon;Azona;118289-78-4;152287-06-4

  • Categories:

    Biochemical Engineering  >  Inhibitors

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.


Ziprasidone is an atypical antipsychotic used in the treatment of schizophrenia and bipolar disorder. Use of ziprasidone has not been consistently associated with serum enzyme elevations and has yet to be linked to instances of clinically apparent acute liver injury.

Ziprasidone hydrochloride Basic Attributes

412.943

448.089142

1312995-182-4

JAL53626GG

DTXSID00153762

Characteristics

76.7

4.75190

>300 °C

Toxicity

Liver test abnormalities have been reported in patients taking ziprasidone, but they have not been well characterized in the literature and the frequency of elevations appears to be similar to placebo therapy. Several instances of hypersensitivity reactions have been reported in patients taking ziprasidone, arising within 1 to 4 weeks of starting therapy and with rapid recurrence on reexposure in at least one case. In several instances, the hypersensitivity reaction qualified as DRESS syndrome with rash, eosinophilia and an accompanying liver injury either in the form of moderate serum enzymes or a mixed hepatitis with jaundice. In all instances, the symptoms, signs and laboratory abnormalities resolved rapidly with stopping ziprasidone. Thus, on rare occasions, ziprasidone can cause acute hypersensitivity reactions that can be accompanied by hepatitis, but the liver injury is usually mild and self-limited.

Drug Information

Ziprasidone is an atypical antipsychotic used in the treatment of schizophrenia and bipolar disorder. Use of ziprasidone has not been consistently associated with serum enzyme elevations and has yet to be linked to instances of clinically apparent acute liver injury.

Antipsychotic Agents

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.)|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.)|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-(4-(3-benzisothiazolyl)piperazinyl)ethyl)-6-chloro-1,3-dihydro-2H-indol-2-one

Ziprasidone hydrochloride Use and Manufacturing

Methods of Manufacturing

Weigh 80 g of ziprasidone base prepared in Example 1, 320 mL of tetrahydrofuran, 600 g of purified water, protected by nitrogen and protected from light, and heated to 50 C with stirring, and slowly added 86.3 g of methanesulfonic acid aqueous solution (22.3g of methanesulfonic acid, 64g of water), after the addition is completed, the temperature is raised to reflux reaction for 30min; after the reaction is completed, the crystallizer is stirred and stirred overnight, filtered, and dried to obtain a crude pink solid ziprasidone mesylate 94g, yield 95%, purity It is 95.2%.

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

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:449.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:4
Exact Mass:448.0891379
Monoisotopic Mass:448.0891379
Topological Polar Surface Area:76.7
Heavy Atom Count:29
Complexity:573
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes

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