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トリフルオロペラジン·塩酸塩

Trifluoperazine Hydrochloride

HCID 66064
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
440-17-5
標準SMILES
CN1CCN(CCCN2c3ccccc3Sc3ccc(C(F)(F)F)cc32)CC1.Cl.Cl
InChIKey
BXDAOUXDMHXPDI-UHFFFAOYSA-N
分子式
C21H26Cl2F3N3S
平均分子量
480.4 g/mol
単同位体質量
479.1176589

概要

Trifluoperazine Hydrochloride is the hydrochloride salt of trifluoperazine, a phenothiazine derivative and a dopamine, alpha-adrenergic, and anticholinergic antagonist with antipsychotic, anxiolytic, and antiemetic activities. Trifluoperazine blocks central dopamine receptors, which may prevent or mitigate delusions and hallucinations caused by an excess of dopamine; dopamine blockade in the chemoreceptor trigger zone (CTZ) may result in an antiemetic effect. This agent binds to central adrenergic receptors, which may result in anxiolytic effects. Trifluoperazine also functions as a calmodulin inhibitor, elevating cytosolic calcium.

名称と識別子

優先名称
Trifluoperazine Hydrochloride
IUPAC
10-[3-(4-methylpiperazin-1-yl)propyl]-2-(trifluoromethyl)phenothiazine;dihydrochloride
現地名
トリフルオロペラジン·塩酸塩
英語名
Trifluoperazine dihydrochloride
分子式
C21H26Cl2F3N3S
分子量
480.42

名称と別名

Trifluoperazine dihydrochloride440-17-5Trifluoperazine hydrochlorideTrifluoperazine HClEskazineTrifluoroperazine dihydrochlorideDTXSID1045085SKF 5019Trifluperazine dihydrochloride6P1Y2SNF5V10-(3-(4-methylpiperazin-1-yl)propyl)-2-(trifluoromethyl)-10H-phenothiazine dihydrochloride10-[3-(4-Methylpiperazin-1-yl)propyl]-2-(trifluoromethyl)-10H-phenothiazine dihydrochloride
名称をさらに表示
10-[3-(4-メチル-1-ピペラジニル)プロピル]-2-(トリフルオロメチル)-10H-フェノチアジン·2塩酸塩トリフルオロペラジン·塩酸塩トリフルオペラジン·2塩酸塩ステラジンテルフルジントリフルオペラジン二塩酸塩トリフルオペラジン塩酸塩塩酸トリフロペラジン10-[3-(4-メチルピペラジン-1-イル)プロピル]-2-(トリフルオロメチル)フェノチアジン二塩酸塩TRIフルオペラジン DIHCLトリフルオペラジン 二塩酸塩トリフルオペラジン 二塩酸塩 溶液トリフルオペラジン 塩酸塩塩酸トリフロペラジン (JAN)Trifluoperazine dihydrochloride, 10-[3-(4-Methylpiperazin-1-yl)propyl]-2-(trifluoromethyl)-10H-phenothiazine dihydrochloride

物性

構造計算による物性

極性表面積
35 Ų
水素結合供与体数
2
水素結合受容体数
7
回転可能結合数
4
重原子数
30
形式電荷
0
複雑度
510

実験および物理化学的性質

Human Drugs · 2 件

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Collision Cross Section188.5 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

物理化学的性質

融点
243 °C · 243 °C (dec.)(lit.)
闪点
9 ℃ · 9℃
貯蔵温度
-20 °C · -20°C
溶解性
5 mg/mL · エタノール:可溶5mg/mL
酸解離定数(Pka)
1 · pK1 3.9, pK2 8.1(at 25℃)
外見
粉
色
ホワイトからオフホワイト
水溶解度
50 g/L, · water: 50g/L, clear
Merck
14 · 14,9680
BRN
3820024 · 3820024
安定性
吸湿性
InChI
1S/C21H24F3N3S.2ClH/c1-25-11-13-26(14-12-25)9-4-10-27-17-5-2-3-6-19(17)28-20-8-7-16(15-18(20)27)21(22,23)24;;/h2-3,5-8,15H,4,9-14H2,1H3;2*1H
InChIKey
BXDAOUXDMHXPDI-UHFFFAOYSA-N
SMILES
Cl[H].Cl[H].CN1CCN(CCCN2c3ccccc3Sc4ccc(cc24)C(F)(F)F)CC1

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 · 4 件

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 42 reports by companies from 3 notifications to the ECHA C&L Inventory.

危険有害性情報

Regulatory InformationHazard Traits - Bioaccumulation; Environmental Persistence
Other Safety InformationIMAP assessments - 10H-Phenothiazine, 10-[3-(4-methyl-1-piperazinyl)propyl]-2-(trifluoromethyl)-, dihydrochloride: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (100%)

毒性情報

Treatment · 1 件

Treatment is essentially symptomatic and supportive. Early gastric lavage is helpful. Keep patient under observation and maintain an open airway, since involvement of the extrapyramidal mechanism may produce dysphagia and respiratory difficulty in severe overdosage. Do not attempt to induce emesis because a dystonic reaction of the head or neck may develop that could result in aspiration of vomitus. Extrapyramidal symptoms may be treated with anti-parkinsonism drugs, barbiturates or Benadryl. See prescribing information for these products. Care should be taken to avoid increasing respiratory depression. If administration of a stimulant is desirable, amphetamine, dextroamphetamine or caffeine with sodium benzoate is recommended. Stimulants that may cause convulsions (e.g., picrotoxin or pentylenetetrazol) should be avoided. If hypotension occurs, the standard measures for managing circulatory shock should be initiated. If it is desirable to administer a vasoconstrictor, Levophed and Neo-Synephrine are most suitable. Other pressor agents, including epinephrine, are not recommended because phenothiazine derivatives may reverse the usual elevating action of these agents and cause a further lowering of blood pressure. (L1712)

化学と産業

薬理情報

Metabolism/MetabolitesHepatic. Half Life: 10-20 hours
FDA Pharmacological Classification · 2 件

TRIFLUOPERAZINE HYDROCHLORIDE

Phenothiazines [CS]; Phenothiazine [EPC]

MeSH Pharmacological Classification · 3 件

Drugs used to prevent NAUSEA or VOMITING.

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.

用途と製造

UsesFor the treatment of anxiety disorders, depressive symptoms secondary to anxiety and agitation.
General Manufacturing Information10H-Phenothiazine, 10-[3-(4-methyl-1-piperazinyl)propyl]-2-(trifluoromethyl)-, hydrochloride (1:2): ACTIVE
応用分野 · 3 件

説明Trifluoperazine (TFP) is a phenothiazine compound with anti-adrenergic and anti-dopaminergic actions typical of antipsychotic agents. It antagonizes adrenergic receptors, with selectivity for α1 over the α2 subtypes (Kis = 24, 653, 163, and 391 nM for α1A, α2A, α2B, and α2C, respectively). TFP binds with much higher affinity to the dopamine D2-like receptor (Kd = 0.96 nM) compared to the dopamine D4-like and the serotonin 5-HT2A receptors (Kds = 44 and 135 nM, respectively). Furthermore, TFP antagonizes calmodulin (CaM) and alters the calcium-binding properties of calsequestrin (CSQ). TFP has been shown to activate type-2 ryanodine receptors independently of its CaM and CSQ activity.

関連反応

0 件
反応記録を作成

現在のフィルター条件では反応記録がありません。

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
Urinox
skf5019
Stelazin
STELAZINE
Eskazinyl
Ai3-50137
NSC-75736910H-Phenothiazine, 10-(3-(4-methyl-1-piperazinyl)propyl)-2-(trifluoromethyl)-, dihydrochlorideDTXCID902508510-(3-(4-Methyl-1-piperazinyl)propyl)-2-(trifluoromethyl)phenothiazine dihydrochloride2-Trifluoromethyl-10-(3'-(1-methyl-4-piperazinyl)propyl)phenothiazine dihydrochloride10H-phenothiazine, 10-[3-(4-methyl-1-piperazinyl)propyl]-2-(trifluoromethyl)-, dihydrochlorideCHEBI:9710NSC17474

データベース識別子

CAS
440-17-5
PubChem CID
66064
DTXSID
DTXSID1045085
ChEMBL
CHEMBL1257040
UNII
6P1Y2SNF5V
EC Number
207-123-0
CAS データベース
440 · 440-17-5(CAS DataBase Reference)
EPAの化学物質情報
10 H-Phenothiazine, · 10H-Phenothiazine, 10-[3-(4-methyl-1-piperazinyl)propyl]-2-(trifluoromethyl)-, dihydrochloride (440-17-5)

化学的性質

化学的特性Cream Fine Powder

Exposure RoutesOral
Toxicity Summary · 1 件

Trifluoperazine blocks postsynaptic mesolimbic dopaminergic D1 and D2 receptors in the brain; depresses the release of hypothalamic and hypophyseal hormones and is believed to depress the reticular activating system thus affecting basal metabolism, body temperature, wakefulness, vasomotor tone, and emesis.

Signs and SymptomsSymptoms of overdose include agitation, coma, convulsions, difficulty breathing, difficulty swallowing, dry mouth, extreme sleepiness, fever, intestinal blockage, irregular heart rate, low blood pressure, and restlessness.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 6 件

Drug Induced Liver Injury Rank (DILIrank 2.0)

Trifluoperazine hydrochloride

vLess-DILI-concern

2

Warnings & precautions

DOI:10.1016/j.drudis.2016.02.015

安全データ

F
3-10
wgk
3
tsca
TSCA listed
rtecs
SP1750000
ridadr
UN1230 - class 3 - PG 2 - Methanol, solution
hs_code
29343000
risk_code
22
hazard_code
Xn
safety_code
36
hazard_class
9
Hazard Classifications
Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Eye Irrit. 2Muta. 2STOT RE 1STOT SE 3
ストレージクラス
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects

使用Trifluoperazine dihydrochloride has been used as a calmodulin kinase antagonist in cultured Aplysia californica neurons. Trifluoperazine dihydrochloride has also been used as a PMCA inhibitor in mouse duodenal tissues to block the transcellular active calcium flux.

一般的な説明Trifluoperazinehydrochloride, 10-[3-(4-Methyl-1-piperazinyl)propyl-[2-(trifluoromethyl)phenothiazine dihydrochloride (Stelazine).The absorption of trifluoperazine is erratic and variable andit is widely distributed into tissues. The excretion of trifluoperazineoccurs 50% via kidneys and the other 50% isthrough enterohepatic circulation. The metabolism and druginteractions of trifluoperazine are the same as with the otherphenothiazines. Trifluoperazine does not show any specificdrug interactions. Trifluoperazine is indicated for the managementof schizophrenia and short-term treatment ofnonpsychotic anxiety.

調製方法 · 1 件

純化方法Recrystallise the salt from absolute EtOH, filter the crystals, dry them in vacuo and store them in tightly stoppered bottles because it is hygroscopic. It is soluble in H2O but insoluble in *C6H6, Et2O and alkaline aqueous solution. It has UV at 258 and 307.5nm (log 4.50 and 3.50) in EtOH (neutral species). [Craig max et al. J Org Chem 22 709 1957.] It is a calmodulin inhibitor [Levene & Weiss J Parmacol Exptl Ther 208 454 1978] and is a psychotropic agent [Fowler Arzneim.-Forsch 27 866 1977]. [Beilstein 27 III/IV 1353.]

上流・下流製品情報

上流原料

1-(3-クロロプロピル)-4-メチルピペラジン2-(トリフルオロメチル)フェノチアジンナトリウムアミド

下流製品

trifluoperazine sulfoxide

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