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440-17-5

440-17-5 structure
440-17-5 structure
  • Name: Trifluoperazine dihydrochloride
  • Chemical Name: trifluoperazine hydrochloride
  • CAS Number: 440-17-5
  • Molecular Formula: C21H26Cl2F3N3S
  • Molecular Weight: 480.417
  • Catalog: API Nervous system medication Antipsychotic
  • Create Date: 2018-02-12 08:00:00
  • Modify Date: 2024-01-01 21:12:13
  • Trifluoperazine Dihydrochloride is a potent dopamine D2 receptor inhibitor used as an antipsychotic and an antiemetic.Target: Dopamine D2 ReceptorTrifluoperazine Dihydrochloride is a potent dopamine D2 receptor inhibitor used as an antipsychotic and an antiemetic. Trifluoperazine inhibited in a dose-dependent manner the stimulation of glycogenolysis, gluconeogenesis, and ureogenesis due to alpha 1-adrenergic stimulation in rat hepatocytes. Trifluoperazine is much more potent at alpha 1- than at alpha 2-adrenergic receptors [1]. Trifluoperazine was not clearly different in terms of 'no substantial improvement' (n=1016, 27 RCTs, RR 1.06 CI 0.98 to 1.14) or leaving the study early (n=930, 22 RCTs, RR 1.15 CI 0.83 to 1.58). Almost identical numbers of people reported at least one adverse event (60%) in each group (n=585, 14 RCTs, RR 0.99 CI 0.87 to 1.13), although trifluoperazine was more likely to cause extrapyramidal adverse effects overall when compared to low potency antipsychotics such as chlorpromazine (n=130, 3 RCTs, RR 1.66 CI 1.03 to 2.67, NNH 6 CI 3 to 121). One small study (n=38) found no clear differences between trifluoperazine and the atypical drug, sulpiride [2].
Name trifluoperazine hydrochloride
Synonyms Trifluoperazine Dihydrochloride
2-Trifluoromethyl-10-[3-(1-methyl-4-piperazinyl)propyl]phenothiazine dihydrochloride
10H-Phenothiazine, 10-[3- (4-methyl-1-piperazinyl)propyl]-2-(trifluoromethyl)-, dihydrochloride
Phenothiazine, 10-[3- (4-methyl-1-piperazinyl)propyl]-2-(trifluoromethyl)-, dihydrochloride
10-[3-(4-methylpiperazin-1-yl)propyl]-2-(trifluoromethyl)phenothiazine dihydrochloride
10-[3-(4-methylpiperazin-1-yl)propyl]-2-(trifluoromethyl)phenothiazine,dihydrochloride
MFCD00012656
10-[3-(4-Methylpiperazin-1-yl)propyl]-2-(trifluoromethyl)-10H-phenothiazine dihydrochloride
EINECS 207-123-0
10H-phenothiazine, 10-[3-(4-methyl-1-piperazinyl)propyl]-2-(trifluoromethyl)-, dihydrochloride
10H-Phenothiazine, 10-[3-(4-methyl-1-piperazinyl)propyl]-2-(trifluoromethyl)-, hydrochloride (1:2)
Eskazine dihydrochloride
Triflurin dihydrochloride
10-[3-(4-Methyl-1-piperazinyl)propyl]-2-(trifluoromethyl)-10H-phenothiazine dihydrochloride
Description Trifluoperazine Dihydrochloride is a potent dopamine D2 receptor inhibitor used as an antipsychotic and an antiemetic.Target: Dopamine D2 ReceptorTrifluoperazine Dihydrochloride is a potent dopamine D2 receptor inhibitor used as an antipsychotic and an antiemetic. Trifluoperazine inhibited in a dose-dependent manner the stimulation of glycogenolysis, gluconeogenesis, and ureogenesis due to alpha 1-adrenergic stimulation in rat hepatocytes. Trifluoperazine is much more potent at alpha 1- than at alpha 2-adrenergic receptors [1]. Trifluoperazine was not clearly different in terms of 'no substantial improvement' (n=1016, 27 RCTs, RR 1.06 CI 0.98 to 1.14) or leaving the study early (n=930, 22 RCTs, RR 1.15 CI 0.83 to 1.58). Almost identical numbers of people reported at least one adverse event (60%) in each group (n=585, 14 RCTs, RR 0.99 CI 0.87 to 1.13), although trifluoperazine was more likely to cause extrapyramidal adverse effects overall when compared to low potency antipsychotics such as chlorpromazine (n=130, 3 RCTs, RR 1.66 CI 1.03 to 2.67, NNH 6 CI 3 to 121). One small study (n=38) found no clear differences between trifluoperazine and the atypical drug, sulpiride [2].
Related Catalog
References

[1]. Huerta-Bahena, J., R. Villalobos-Molina, and J.A. Garcia-Sainz, Trifluoperazine and chlorpromazine antagonize alpha 1- but not alpha2- adrenergic effects. Mol Pharmacol, 1983. 23(1): p. 67-70.

[2]. Marques, L.O., M.S. Lima, and B.G. Soares, Trifluoperazine for schizophrenia. Cochrane Database Syst Rev, 2004(1): p. CD003545.
Boiling Point 506ºC at 760 mmHg
Melting Point 243 °C (dec.)(lit.)
Molecular Formula C21H26Cl2F3N3S
Molecular Weight 480.417
Flash Point 259.8ºC
Exact Mass 479.117645
PSA 35.02000
LogP 6.49040
Vapour Pressure 2.32E-10mmHg at 25°C
Storage condition 2-8°C
Stability Hygroscopic

CHEMICAL IDENTIFICATION

RTECS NUMBER :
SP1750000
CHEMICAL NAME :
Phenothiazine, 10-(3-(4-methyl-1-piperazinyl)propyl)-2-(trifluoromet hyl)-, dihydrochloride
CAS REGISTRY NUMBER :
440-17-5
LAST UPDATED :
199707
DATA ITEMS CITED :
18
MOLECULAR FORMULA :
C21-H24-F3-N3-S.2Cl-H
MOLECULAR WEIGHT :
480.46
WISWESSER LINE NOTATION :
T C666 BN ISJ EXFFF B3- AT6N DNTJ D1 &GH 2

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
1143 ug/kg/1D-I
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia Behavioral - muscle contraction or spasticity
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
543 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
424 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
133 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
82 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Primate - monkey
DOSE/DURATION :
>20 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - muscle weakness Behavioral - rigidity (including catalepsy)
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
65 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TCLo - Lowest published toxic concentration
ROUTE OF EXPOSURE :
Inhalation
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
660 ug/m3/4H/17W-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - urine volume increased Endocrine - changes in thyroid weight Blood - changes in erythrocyte (RBC) count
TYPE OF TEST :
TCLo - Lowest published toxic concentration
ROUTE OF EXPOSURE :
Inhalation
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
660 ug/m3/4H/17W-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - urine volume increased Endocrine - changes in thyroid weight Blood - changes in erythrocyte (RBC) count
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
DOSE :
220 mg/kg
SEX/DURATION :
female 1-22 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - biochemical and metabolic
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
80 ug/kg
SEX/DURATION :
male 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)
TYPE OF TEST :
Cytogenetic analysis
TYPE OF TEST :
Cytogenetic analysis
TYPE OF TEST :
Micronucleus test
TYPE OF TEST :
Cytogenetic analysis

MUTATION DATA

TEST SYSTEM :
Rodent - mouse
DOSE/DURATION :
80 ug/kg/24H
REFERENCE :
FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 25,615,1987 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3217 No. of Facilities: 82 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 1343 (estimated) No. of Female Employees: 617 (estimated)
Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302
Precautionary Statements P301 + P312 + P330
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xn:Harmful;
Risk Phrases R22
Safety Phrases S36
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS SP1750000
Precursor  0

DownStream  1


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