Ziprasidone Hydrochloride
CP-88059 HCl · CP88059 hydrochloride · CP 88059 hydrochloride · CP-88059 hydrochloride · ZIPRASIDONE HYDROCHLORIDE · Ziprasidone HCl (CP-88059) · Ziprasidone hydrochloride, 10 mM in DMSO · Ziprasidone hydrochloride (CP-88059 hydrochloride
Identifikatoren & physikalische Daten
| CAS No. | 122883-93-6 |
|---|---|
| Summenformel | C21H22Cl2N4OS |
| Durchschnittliche Molmasse | 449,4 g/mol |
| Monoisotopische Masse | 448,08913768 g/mol |
| SMILES | Cl.O=C1Cc2cc(CCN3CCN(c4nsc5ccccc45)CC3)c(Cl)cc2N1 |
| InChIKey | NZDBKBRIBJLNNT-UHFFFAOYSA-N |
| PubChem CID | 219099 |
| ChEMBL | CHEMBL1375743 |
| EC No. | 602-903-0 |
| DTXSID | DTXSID00153762 |
Chemische & physikalische Eigenschaften
| Polarare Oberfläche (TPSA) | 76,7 |
|---|---|
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 5 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 29 |
| Formalladung | 0 |
| Komplexität | 573 |
| Human Drugs | Breast FeedingLactationMilk, HumanAntipsychotic AgentsFDA approved drugs -> Active ingredient |
| Schmelzpunkt | >300 °C |
| Lagerbedingungen | Store at -20°C |
| Löslichkeit | 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) |
| InChIKey | ZCBZSCBNOOIHFP-UHFFFAOYSA-N |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 33.3% (1 of 3) of reports.WarningH315 (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. |
|---|---|
| Hazard Classes and Categories | Skin Irrit. 2 (33.3%) |
| Drug Induced Liver Injury | Drug Induced Liver Injury Rank (DILIrank 2.0)Ziprasidone hydrochloridevLess-DILI-concern3Adverse reactionsDOI:10.1016/j.drudis.2016.02.015 |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation |
| Wassergefährdungsklasse (WGK) | WGK 2 |
| Lagerklasse | 3 - Flammable liquids |
| Gefahrenklasse | Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1 |
Anwendungen & Verwendung
Beschreibung
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.
Verwenden
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