Fluphenazine enanthate

Names

[ Name ]:
Fluphenazine enanthate

[Synonym ]:
Fluphenazine enantate
2-(4-{3-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]propyl}piperazin-1-yl)ethyl heptanoate
Fluphenazinenanthat
Fluphenanzin-aenanthat
2-[4-[3-[2-(Trifluoromethyl)phenothiazin-10-yl]propyl]-1-piperazinyl]ethyl heptanoate
Fluphenazin-aenanthsaeureester
4-<3-<2-Trifluormethyl-phenothiazinyl-(10)>-propyl>-1-(2-hydroxy-ethyl)-piperazin-heptanoat
1-heptanoyloxy-2-{4-[3-(2-trifluoromethyl-phenothiazin-10-yl)-propyl]-piperazin-1-yl}-ethane
Moditen-retard
Prolixin Enanthate
fluphenazine enanthate
fluphenazine O-enantate
Eutimox
EINECS 220-385-0

Biological Activity

[Description]:

Fluphenazine enanthate is the first long-acting injectable (LAI) antipsychotic for the treatment of schizophrenia[1][2].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Neurological Disease

[In Vivo]

Fluphenazine enanthate (2,4, 8 mg/kg; IM) significant inhibition of the avoidance performance is observed as long as 16, 23, and 28 days, respectively[1]. Fluphenazine enanthate (8 mg/kg) drinking behavior is almost completely suppressed for 24 hours immediately following the administration[1]. Fluphenazine enanthate (8 mg/kg) produces transient body weight Iosses in the rats[1]. Animal Model: Fifty-four male adult rats of Wistar strain[1] Dosage: 2, 4, and 8 mg/kg Administration: Index medicus (IM ) Result: Three doses of Fluphenazine enanthate significant inhibition of the avoidance performance was observed as long as 16, 23, and 28 days, respectively.

[References]

[1]. Kuribara H, et al. Effects of fluphenazine enanthate and fluphenazine decanoate on discriminated avoidanceresponse and water drinking behavior in rats. Psychopharmacology (Berl). 1979 Sep;65(1):1-6.

[2]. Brissos S, et al. The role of long-acting injectable antipsychotics in schizophrenia: a critical appraisal. Ther Adv Psychopharmacol. 2014 Oct;4(5):198-219.

Chemical & Physical Properties

[ Density]:
1.181g/cm3

[ Boiling Point ]:
629.4ºC at 760mmHg

[ Molecular Formula ]:
C₂₉H₃₈F₃N₃O₂S

[ Molecular Weight ]:
549.69100

[ Flash Point ]:
334.4ºC

[ Exact Mass ]:
549.26400

[ PSA ]:
61.32000

[ LogP ]:
6.77020

[ Vapour Pressure ]:
9.41E-16mmHg at 25°C

[ Index of Refraction ]:
1.544

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: MJ2450000

CHEMICAL NAME :: Heptanoic acid, 2-(4-(3-(2-(trifluoromethyl)phenothiazin-10-yl)propyl )- 1-piperazinyl)ethyl ester

CAS REGISTRY NUMBER :: 2746-81-8

LAST UPDATED :: 199612

DATA ITEMS CITED :: 7

MOLECULAR FORMULA :: C29-H38-F3-N3-O2-S

MOLECULAR WEIGHT :: 549.76

WISWESSER LINE NOTATION :: T C666 BN ISJ EXFFF B3- AT6N DNTJ D2OV6

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Human

DOSE/DURATION :: 357 ug/kg

TOXIC EFFECTS :: Behavioral - muscle weakness

REFERENCE :: AJPSAO American Journal of Psychiatry. (American Psychiatric Assoc., Circulation Dept., 1400 K St., NW, Washington, DC 20005) V.78- 1921- Volume(issue)/page/year: 119,779,1963

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Human

DOSE/DURATION :: 1633 ug/kg

TOXIC EFFECTS :: Musculoskeletal - other changes

REFERENCE :: BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 2,1071,1966

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 300 mg/kg

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

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,701,1982

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 50 mg/kg

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

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,701,1982

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 56 mg/kg

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

REFERENCE :: CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) Volume(issue)/page/year: NX#03337

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

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 17200 ug/kg

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

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,701,1982 *** REVIEWS *** TOXICOLOGY REVIEW ABPYBL Advances in Biochemical Psychopharmacology. (Raven Press, 1185 Ave. of the Americas, New York, NY 10036) V.1- 1969- Volume(issue)/page/year: 9,301,1974

Safety Information

[ RIDADR ]:
UN 3249

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

Articles

Ten year outcomes of outpatients with schizophrenia on conventional depot antipsychotics: a systematic chart review.

Int. Clin. Psychopharmacol. 28(5) , 261-6, (2013)

Long-term follow-up data of patients with schizophrenia on depot antipsychotics have been few and the longest follow-up period has been up to 7 years. We carried out a systematic chart review to exami...

Treatment of schizophrenia with depot preparations of fluphenazine, haloperidol, and risperidone among inpatients at state-operated psychiatric facilities.

Schizophr. Res. 119(1-3) , 153-9, (2010)

This study aimed to characterize the inpatient utilization of depot antipsychotics.The characteristics of adults with schizophrenia or schizoaffective disorder, hospitalized for at least 28 days, and ...

Multiple congenital abnormalities in a newborn boy associated with maternal use of fluphenazine enanthate and other drugs during pregnancy.

Acta Paediatr. Scand. 71(2) , 335-8, (1982)

A boy was born with a short sloping forehead, wide metopic suture, persistent metopic fontanelle, telecanthus, ocular hypertelorism, nystagmoid eye movements, bilateral cleft lip and palate, imperfora...