ジプラシドン・塩酸塩
Ziprasidone Hydrochloride
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基本情報
- CAS
122883-93-6- 標準SMILES
Cl.O=C1Cc2cc(CCN3CCN(c4nsc5ccccc45)CC3)c(Cl)cc2N1- InChIKey
NZDBKBRIBJLNNT-UHFFFAOYSA-N- 分子式
- C21H22Cl2N4OS
- 平均分子量
- 449.4 g/mol
- 単同位体質量
- 448.08913768
概要
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.
名称と識別子
- 優先名称
- Ziprasidone Hydrochloride
- IUPAC
- 5-[2-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]ethyl]-6-chloro-1,3-dihydroindol-2-one;hydrochloride
- 現地名
- ジプラシドン・塩酸塩
- 英語名
- Ziprasidone Hydrochloride
- 分子式
- C21H21ClN4OS
- 分子量
- 412.943
名称と別名
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
名称をさらに表示
ジプラシドン・塩酸塩6-クロロ-5-[2-[4-(1,2-ベンゾイソチアゾール-3-イル)ピペラジン-1-イル]エチル]-1,3-ジヒドロ-2H-インドール-2-オン・塩酸塩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)
物性
構造計算による物性補完中
- 極性表面積
- 76.7 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 5
- 回転可能結合数
- 4
- 重原子数
- 29
- 形式電荷
- 0
- 複雑度
- 573
実験および物理化学的性質
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antipsychotic Agents
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
物理化学的性質
- 融点
- 300 °C · >300 °C
- 貯蔵温度
- -20 °C · Store at -20°C
- 溶解性
- 10 mM · Soluble in DMSO > 10 mM
- 外見
- Powder
- 安定性
- 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
- InChIKey
- ZCBZSCBNOOIHFP-UHFFFAOYSA-N
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
GHS Classification
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.
危険有害性情報
Hazard Classes and CategoriesSkin Irrit. 2 (33.3%)
毒性情報
Drug Induced Liver Injury
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
安全データ
- wgk
- WGK 2
- Hazard Classifications
- Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1
- ストレージクラス
- 3 - Flammable liquids
化学と産業
薬理情報
FDA Pharmacological Classification
ZIPRASIDONE HCL
Atypical Antipsychotic [EPC]
ZIPRASIDONE HYDROCHLORIDE
Atypical Antipsychotic [EPC]
MeSH Pharmacological Classification
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.
応用分野
説明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.
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