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4-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]piperazine-1-ethanol dihydrochloride

Names

[ CAS No. ]:
2015-28-3

[ Name ]:
4-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]piperazine-1-ethanol dihydrochloride

[Synonym ]:
Perphenazin-dihydrochlorid
EINECS 217-944-6
Perphenazine HCl
Perphenazine dihydrochloride

Biological Activity

[Description]:

Perphenazine dihydrochloride is an orally active dopamine receptor and histamine-1 receptor antagonist, with Ki values of 0.56 nM (D2), 0.43 nM (D3), .6 nM (5-HT2A), respectively. Perphenazine dihydrochloride also binds to Alpha-1A adrenergic receptor. Perphenazine dihydrochloride inhibits cancer cell proliferation, and induces apoptosis. Perphenazine dihydrochloride can be used in the research of mental disease, cancer, inflammation[1][3][5].

[Related Catalog]:

Signaling Pathways >> Immunology/Inflammation >> Histamine Receptor
Signaling Pathways >> Autophagy >> Autophagy
Signaling Pathways >> Apoptosis >> Apoptosis
Research Areas >> Cancer
Research Areas >> Endocrinology
Signaling Pathways >> GPCR/G Protein >> Dopamine Receptor
Signaling Pathways >> GPCR/G Protein >> Adrenergic Receptor
Research Areas >> Inflammation/Immunology
Signaling Pathways >> Neuronal Signaling >> Dopamine Receptor
Research Areas >> Neurological Disease
Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor
Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor
Signaling Pathways >> GPCR/G Protein >> Histamine Receptor

[Target]

D2 Receptor:0.56 nM (Ki)

D3 Receptor:0.43 nM (Ki)

D4 Receptor:28.5 nM (Ki)

5-HT2A Receptor:5.6 nM (Ki)

5-HT6 Receptor:17 nM (Ki)

5-HT7 Receptor:23 nM (Ki)

5-HT2C Receptor:132 nM (Ki)

5-HT1A Receptor:421 nM (Ki)


[In Vitro]

Perphenazine dihydrochloride (40 μM, 48 h) inhibits cell viability, and induces cell apoptosis mediated by CTSD (Cathepsin D) in L02 cells[2]. Perphenazine dihydrochloride (30 μM, 24 h) induces intense lysosome vacuolation, impaired lysosomal membrane, and induces lysosomal membrane permeabilization (LMP), ultimately triggering lysosomal cell death in L02 cells[2]. Perphenazine dihydrochloride (10-40 μM, 24 h) inhibits autophagic flux in L02 cells[2]. Perphenazine dihydrochloride (1 µM, 24 h) decreases glioblastoma U-87 MG cell migration and invasion[4]. Cell Viability Assay[2] Cell Line: L02 cells Concentration: 10-100 μM Incubation Time: 12, 24, 48 h Result: Inhibited cell viability in a concentration and time-dependent manner. Western Blot Analysis[2] Cell Line: L02 cells Concentration: 10, 20, 30, and 40 μM Incubation Time: 24 h Result: Increased LC3 I/II and P62/SQSTM1 levels Cell Migration Assay [4] Cell Line: U-87 MG cells Concentration: 0, 3, 6, 9, 12, and 24 h Incubation Time: 0, 3, 6, 9, 12, and 24 h Result: Increased the wound closure in human glioblastoma cell cultures from 24.6 to 62.7%.

[In Vivo]

Perphenazine dihydrochloride (oral gavage, 180 mg/kg, every other day for 21 days) induces liver injury and lysosomal membrane damage in ICR mice[2]. Perphenazine dihydrochloride (oral administration, 10 mg/kg, every other day for 6 days) attenuates morphological phenotype in mouse models of Th2-type allergic dermatitis[3]. Animal Model: ICR mice[2] Dosage: 10, 30, 60, 120, 180 mg/kg Administration: Oral gavage, every other day for 21 days. Result: Increased histological injury and aminotransferases compared with control. Animal Model: Oxazolone-treated animal model of dermatitis[3] Dosage: 10 mg/kg Administration: Oral administration, every other day for 6 days Result: Decreased The levels of mice ear swelling.

[References]

[1]. Richtand NM, et al. Dopamine and serotonin receptor binding and antipsychotic efficacy. Neuropsychopharmacology. 2007 Aug;32(8):1715-26.

[2]. Lei Tao, et al. Lysosomal membrane permeabilization mediated apoptosis involve in perphenazine-induced hepatotoxicity in vitro and in vivo. Toxicol Lett. 2022 Jul 29;367:76-87.

[3]. Min-Jeong Heo, et al. Perphenazine Attenuates the Pro-Inflammatory Responses in Mouse Models of Th2-Type Allergic Dermatitis. Int J Mol Sci. 2020 May 3;21(9):3241.

[4]. Michał Otręba, et al. Perphenazine and prochlorperazine decrease glioblastoma U-87 MG cell migration and invasion: Analysis of the ABCB1 and ABCG2 transporters, E-cadherin, α-tubulin and integrins (α3, α5, and β1) levels. Oncol Lett. 2022 Jun;23(6):182.

[5]. Michał Otręba, et al. n vitro anticancer activity of fluphenazine, perphenazine and prochlorperazine. A review. J Appl Toxicol. 2021 Jan;41(1):82-94.

Chemical & Physical Properties

[ Boiling Point ]:
580.4ºC at 760mmHg

[ Molecular Formula ]:
C21H28Cl3N3OS

[ Molecular Weight ]:
476.89100

[ Flash Point ]:
304.8ºC

[ Exact Mass ]:
475.10200

[ PSA ]:
55.25000

[ LogP ]:
5.48750

[ Vapour Pressure ]:
2.6E-14mmHg at 25°C

[ Storage condition ]:
2-8°C