Fluphenazine

Names

[ CAS No. ]:
69-23-8

[ Name ]:
Fluphenazine

[Synonym ]:
1-Piperazineethanol, 4-(3-(2-(trifluoromethyl)-10H-phenothiazin-10-yl)propyl)-
2-{4-[3-(2-trifluoromethyl-phenothiazin-10-yl)-propyl]-piperazin-1-yl}-ethanol
hiazine
dapotum
4-(3-(2-(trifluoromethyl)phenothiazin-10-yl)propyl)-1-Piperazineethanol
Sevinol
Elinol
Pacinol
10-[3'-[4''-(b-Hydroxyethyl)-1''-piperazinyl]propyl]-3-trifluoromethylphenothiazine
2-(Trifluoromethyl)-10-[3-[1-(b-hydroxyethyl)-4-piperazinyl]propyl]phenothiazine
4-[3-[2-(Trifluoromethyl)-10H-phenothiazin-10-yl]propyl]-1-piperazineethanol
4-[3-[2-(trifluoromethyl)phenothiazine-10-yl]propyl]-1-piperazineethanol
S 94
2-(4-(3-(2-(Trifluoromethyl)-10H-phenothiazin-10-yl)propyl)piperazin-1-yl)ethanol
Fluphenazine
2-(4-{3-[2-(Trifluoromethyl)-10H-phenothiazin-10-yl]propyl}-1-piperazinyl)ethanol
1-Piperazineethanol, 4-[3-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]propyl]-
2-(4-{3-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]propyl}piperazin-1-yl)ethanol
1-(2-Hydroxyethyl)-4-[3-(trifluoromethyl-10-phenothiazinyl)propyl]piperazine

Biological Activity

[Description]:

Fluphenazine is a potent, orally active phenothiazine-based dopamine receptor antagonist. Fluphenazine is used for the research of schizophrenia. Fluphenazine blocks neuronal voltage-gated sodium channels[1].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> Sodium Channel

Signaling Pathways >> GPCR/G Protein >> Dopamine Receptor

Signaling Pathways >> Neuronal Signaling >> Dopamine Receptor

Research Areas >> Neurological Disease

[References]

[1]. Zhou X, et al. The neuroleptic drug, fluphenazine, blocks neuronal voltage-gated sodium channels. Brain Res. 2006;1106(1):72-81.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
568.3±50.0 °C at 760 mmHg

[ Melting Point ]:
268-274℃

[ Molecular Formula ]:
C₂₂H₂₆F₃N₃OS

[ Molecular Weight ]:
437.522

[ Flash Point ]:
297.5±30.1 °C

[ Exact Mass ]:
437.174866

[ PSA ]:
55.25000

[ LogP ]:
4.84

[ Vapour Pressure ]:
0.0±1.6 mmHg at 25°C

[ Index of Refraction ]:
1.579

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TL9730000

CHEMICAL NAME :: 1-Piperazineethanol, 4-(3-(2-(trifluoromethyl)phenothiazin-10-yl)propyl)-

CAS REGISTRY NUMBER :: 69-23-8

LAST UPDATED :: 199706

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C22-H26-F3-N3-O-S

MOLECULAR WEIGHT :: 437.57

WISWESSER LINE NOTATION :: T C666 BN ISJ EXFFF B3- AT6N DNTJ D2Q

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 2,540,1960

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 640 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - ptosis Autonomic Nervous System - central sympatholytic Behavioral - alteration of classical conditioning

REFERENCE :: MDCHAG Medicinal Chemistry: A Series of Monographs. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1963- Volume(issue)/page/year: 4(2),199,1967

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 220 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 2,540,1960

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 89 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - changes in motor activity (specific assay) Behavioral - coma

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 145,450,1963

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 51 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 2,540,1960 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 62 mg/kg

SEX/DURATION :: female 9 day(s) pre-mating female 1-22 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)

REFERENCE :: APEPA2 Naunyn-Schmiedebergs Archiv fuer Pharmakologie und Experimentelle Pathologie. (Berlin, Ger.) V.254-263, 1966-69. For publisher information, see NSAPCC. Volume(issue)/page/year: 257,338,1967

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 18 mg/kg

SEX/DURATION :: female 9 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - mating performance (e.g. # sperm positive females per # females mated; # copulations per # estrus cycles)

REFERENCE :: APEPA2 Naunyn-Schmiedebergs Archiv fuer Pharmakologie und Experimentelle Pathologie. (Berlin, Ger.) V.254-263, 1966-69. For publisher information, see NSAPCC. Volume(issue)/page/year: 257,338,1967 *** REVIEWS *** TOXICOLOGY REVIEW JMSCA9 Journal of Mental Science. (London, UK) V.4-108, 1857-1962. For publisher information, see BJPYAJ. Volume(issue)/page/year: 106,755,1960 TOXICOLOGY REVIEW IDPYAK Industrial Pharmacology. (Mount Kisco, NY) V.1-3, 1974-79. Discontinued. Volume(issue)/page/year: 1,203,1974

Safety Information

[ Symbol ]:

GHS02, GHS06, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H225-H301 + H311 + H331-H370

[ Precautionary Statements ]:
P210-P260-P280-P301 + P310-P311

[ Hazard Codes ]:
F,T

[ Risk Phrases ]:
11-23/24/25-39/23/24/25

[ Safety Phrases ]:
16-36/37-45

[ RIDADR ]:
UN1230 - class 3 - PG 2 - Methanol, solution

Synthetic Route

Click to get detail synthetic route

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