10-(3-(4-Methyl-1-piperazinyl)-propyl)-2-(trifluor-methyl)-10H-dihydrochlorid
TRIFLUOPERAZINE HCL · TRIFLUOPERAZINE HYDROCHLORIDE · Trifluoperazine dihydrochloride, 10-[3-(4-Methylpiperazin-1-yl)propyl]-2-(trifluoromethyl)-10H-phenothiazine dihydrochloride · Urinox · skf5019 · Stelazin · eskazine · STELAZINE
Identifikatoren & physikalische Daten
| CAS No. | 440-17-5 |
|---|---|
| Summenformel | C21H26Cl2F3N3S |
| Durchschnittliche Molmasse | 480,4 g/mol |
| Monoisotopische Masse | 479,1176589 g/mol |
| SMILES | CN1CCN(CCCN2c3ccccc3Sc3ccc(C(F)(F)F)cc32)CC1.Cl.Cl |
| InChIKey | BXDAOUXDMHXPDI-UHFFFAOYSA-N |
| PubChem CID | 66064 |
| ChEMBL | CHEMBL1257040 |
| EC No. | 207-123-0 |
| DTXSID | DTXSID1045085 |
| Lokaler Name | 10-(3-(4-Methyl-1-piperazinyl)-propyl)-2-(trifluor-methyl)-10H-dihydrochlorid |
Chemische & physikalische Eigenschaften
| Polarare Oberfläche (TPSA) | 35 |
|---|---|
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 7 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 30 |
| Formalladung | 0 |
| Komplexität | 510 |
| Human Drugs | FDA approved drugs -> Active ingredient |
| Collision Cross Section | 188.5 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| Schmelzpunkt | 243 °C (dec.)(lit.) |
| Flammpunkt | 9℃ |
| Lagerbedingungen | -20°C |
| Löslichkeit | ethanol: soluble5mg/mLwater: 50g/L, clear |
| pKa (Säurekonstante) | pK1 3.9, pK2 8.1(at 25℃) |
| Aggregatzustand | powder |
| Farbe | white to off-white |
| Merck | 14,9680 |
| BRN | 3820024 |
| Stabilität | Hygroscopic |
| 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,4,9-14H2,1H32*1H |
| InChIKey | BXDAOUXDMHXPDI-UHFFFAOYSA-N |
| SMILES | Cl[H].Cl[H].CN1CCN(CCCN2c3ccccc3Sc4ccc(cc24)C(F)(F)F)CC1 |
| CAS Datenbank | 440-17-5(CAS DataBase Reference) |
| EPA chemische Informationen | 10H-Phenothiazine, 10-[3-(4-methyl-1-piperazinyl)propyl]-2-(trifluoromethyl)-, dihydrochloride (440-17-5) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (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. |
|---|---|
| Regulatorische Informationen | Hazard Traits - BioaccumulationEnvironmental Persistence |
| Weitere Sicherheitsinformationen | IMAP assessments - 10H-Phenothiazine, 10-[3-(4-methyl-1-piperazinyl)propyl]-2-(trifluoromethyl)-, dihydrochloride: Environment tier I assessment |
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| Treatment | 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) |
| Expositionspfade | Oral |
| Toxizitätsübersicht | Trifluoperazine blocks postsynaptic mesolimbic dopaminergic D1 and D2 receptors in the braindepresses 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. |
Anwendungen & Verwendung
Beschreibung
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.
Verwenden
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.