Ziprasidone Hydrochloride

HCID 219099CAS 122883-93-6

Grundinformationen

Standard-SMILES
Cl.O=C1Cc2cc(CCN3CCN(c4nsc5ccccc45)CC3)c(Cl)cc2N1
InChIKey
NZDBKBRIBJLNNT-UHFFFAOYSA-N
Summenformel
C21H22Cl2N4OS
Durchschnittliche Molmasse
449,4 g/mol
Monoisotopische Masse
448,08913768

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
Ziprasidone Hydrochloride
IUPAC
5-[2-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]ethyl]-6-chloro-1,3-dihydroindol-2-one;hydrochloride
Englischer Name
Ziprasidone Hydrochloride
Summenformel
C21H21ClN4OS
Molmasse
412.943

Namen und Synonyme

Ziprasidone hydrochloride122883-93-6Ziprasidone HClZeldoxJAL53626GGDTXSID00153762ziprasidone hydrochloride, monohydrateCP-880591Geodon, CapsulesRefChem:56242DTXCID00762535-(2-(4-(1,2-Benzisothiazol-3-yl)-1-piperazinyl)ethyl)-6-chloro-1,3-dihydro-2H-Indol-2-one Monohydrochloride
Weitere Namen anzeigen
CP-88059 HClCP88059 hydrochlorideCP 88059 hydrochlorideCP-88059 hydrochlorideZiprasidone HCl (CP-88059)Ziprasidone hydrochloride, 10 mM in DMSOZiprasidone hydrochloride (CP-88059 hydrochloride2H-Indol-2-one,5-[2-[4-(1,2-benzisothiazol-3-yl)-1-piperazin...5-[2-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]ethyl]-6-chloro-oxindole hydrochloride
216X081ORUCP-88,059-1CP-88059-15-(2-(4-(Benzo[d]isothiazol-3-yl)piperazin-1-yl)ethyl)-6-chloroindolin-2-one hydrochlorideGeodonC21H22Cl2N4OS5-[2-[4-(1,2-Benzisothiazol-3-yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2H-indol-2-one hydrochlorideZiprasidone (hydrochloride)

Datenbank-Bezeichner

CAS
122883-93-6
PubChem CID
219099
DTXSID
DTXSID00153762
ChEMBL
CHEMBL1375743
UNII
JAL53626GG
EC Number
602-903-0

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA)
76,7 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
5
Frei drehbare Bindungen
4
Schwere Atome
29

Experimentelle und physikochemische Eigenschaften

Human Drugs · 3 Einträge

Breast Feeding; Lactation; Milk, Human; Antipsychotic Agents

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Physikochemische Eigenschaften

Schmelzpunkt
300 °C · >300 °C
storage temp.
-20 °C · Store at -20°C
Löslichkeit
10 mM · Soluble in DMSO > 10 mM
Aggregatzustand
Powder
Stabilität
Hygroscopic
InChI
1S/C21H21ClN4OS.ClH.H2O/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;1H2

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for 33.3% (1 of 3) of reports.

Warning

H315 (33.3%): Causes skin irritation [Warning Skin corrosion/irritation]

P260, P261, P264, P264+P265, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesSkin Irrit. 2 (33.3%)

Toxikologische Informationen

Drug Induced Liver Injury · 6 Einträge

Drug Induced Liver Injury Rank (DILIrank 2.0)

Ziprasidone hydrochloride

vLess-DILI-concern

3

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Sicherheitsdaten

wgk
WGK 2
Speicherklasse
3 - Flammable liquids
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1

Chemie und Industrie

Pharmakologische Informationen

FDA Pharmacological Classification · 4 Einträge

ZIPRASIDONE HCL

Atypical Antipsychotic [EPC]

ZIPRASIDONE HYDROCHLORIDE

Atypical Antipsychotic [EPC]

MeSH Pharmacological Classification · 3 Einträge

Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or SEROTONIN RECEPTOR AGONISTS.

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.

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.

Anwendungen · 2 Einträge

BeschreibungBoth 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.

VerwendenZiprasidone (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

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