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F4765

Sigma-Aldrich

Fluphenazine dihydrochloride

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Synonym(s):
4-[3-[2-(Trifluoromethyl)-10H-phenothiazin-10-yl]propyl]-1-piperazineethanol dihydrochloride
Empirical Formula (Hill Notation):
C22H26F3N3OS · 2HCl
CAS Number:
146-56-5
Molecular Weight:
510.44
EC Number:
205-674-1
MDL number:
MFCD00055212
UNSPSC Code:
12352200
PubChem Substance ID:
57654184
NACRES:
NA.77

SMILES string

Cl.Cl.OCCN1CCN(CCCN2c3ccccc3Sc4ccc(cc24)C(F)(F)F)CC1

InChI

1S/C22H26F3N3OS.2ClH/c23-22(24,25)17-6-7-21-19(16-17)28(18-4-1-2-5-20(18)30-21)9-3-8-26-10-12-27(13-11-26)14-15-29;;/h1-2,4-7,16,29H,3,8-15H2;2*1H

InChI key

MBHNWCYEGXQEIT-UHFFFAOYSA-N

Gene Information

human ... DRD1(1812) , DRD2(1813) , HRH1(3269)

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General description

Fluphenazine may be useful for the treatment of schizophrenia.

Application

Fluphenazine dihydrochloride has been used:
  • to study its effects as a drug on glioblastoma (GBM) cells
  • in fluorescence-activated cell sorting (FACS) analysis, sorting and single-cell stress-survival experiments
  • to study its exposure effects on learning and memory in adult rats

Biochem/physiol Actions

D1/D2 dopamine receptor antagonist; phenothiazine antipsychotic; H1 histamine receptor antagonist.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301,H360

Precautionary Statements

P201 - P301 + P310 + P330

Hazard Classifications

Acute Tox. 3 Oral - Repr. 1A

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Coupling phenotypic persistence to DNA damage increases genetic diversity in severe stress
Yaakov G, et al.
Nature ecology & evolution, 1(1), 0016-0016 (2017)
Principles of Psychopharmacology for Mental Health Professionals (2006)
G Cai et al.
Molecular pharmacology, 56(5), 989-996 (1999-10-26)
The interaction of dopaminergic antagonists with the D(1A) dopamine receptor was assessed in PC2 cells that transiently express this receptor. The maximal binding and dissociation constants for the D(1A) dopamine receptor, using the ligand [(125)I]SCH23982 were 0.38 +/- 0.09 nM
The Effect of Intrauterine Antipsychotic Drug Exposure on Learning and Memory in Adult Rats
Oltulu C and Karadag CH
Klinik Psikofarmakoloji Bulteni-Bulletin of Clinical Psychopharmacology, 26(4), 364-373 (2016)
Identification of thioridazine, an antipsychotic drug, as an antiglioblastoma and anticancer stem cell agent using public gene expression data
Cheng HW, et al.
Cell Death & Disease, 6(5), e1753-e1753 (2015)
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