Details
Stereochemistry | ACHIRAL |
Molecular Formula | C22H26F3N3OS |
Molecular Weight | 437.5235 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
c1ccc2c(c1)N(CCCN3CCN(CC3)CCO)c4cc(ccc4S2)C(F)(F)F
InChI
InChIKey=PLDUPXSUYLZYBN-UHFFFAOYSA-N
InChI=1S/C22H26F3N3OS/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
Molecular Formula | C22H26F3N3OS |
Molecular Weight | 437.5235 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.drugbank.ca/drugs/DB00623Curator's Comment:: Description was created based on several sources, including
Sources: http://www.drugbank.ca/drugs/DB00623
Curator's Comment:: Description was created based on several sources, including
Fluphenazine is a trifluoro-methyl phenothiazine derivative intended for the management of schizophrenia and other psychotic disorders. Fluphenazine has not been shown effective in the management of behaviorial complications in patients with mental retardation. Fluphenazine blocks postsynaptic mesolimbic dopaminergic D1 and D2 receptors in the brain; depresses the release of hypothalamic and hypophyseal hormones and is believed to depress the reticular activating system thus affecting basal metabolism, body temperature, wakefulness, vasomotor tone, and emesis.
CNS Activity
Originator
Sources: http://adisinsight.springer.com/drugs/800002142
Curator's Comment:: Introduced in 1959
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3383 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9755905 |
|||
Target ID: CHEMBL217 Sources: http://www.drugbank.ca/drugs/DB00623 |
|||
Target ID: CHEMBL225 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11561066 |
1.412 µM [EC50] | ||
Target ID: CHEMBL1907610 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2879204 |
|||
Target ID: CHEMBL2056 Sources: http://www.drugbank.ca/drugs/DB00623 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | FLUPHENAZINE DECANOATE Approved UseFluphenazine Decanoate Injection is a longacting parenteral antipsychotic drug intended for use in the management of patients requiring prolonged parenteral neuroleptic therapy (e.g., chronic schizophrenics). Launch Date5.5313282E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.3 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8911886 |
12 mg single, oral dose: 12 mg route of administration: Oral experiment type: SINGLE co-administered: |
FLUPHENAZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
261 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8911886 |
2.5 mg 3 times / 3 days multiple, intravenous dose: 2.5 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FLUPHENAZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
0.52 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2313572 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
FLUPHENAZINE plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6.92 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2313572 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
FLUPHENAZINE plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
14.4 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8911886 |
12 mg single, oral dose: 12 mg route of administration: Oral experiment type: SINGLE co-administered: |
FLUPHENAZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
12.3 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8911886 |
2.5 mg 3 times / 3 days multiple, intravenous dose: 2.5 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
FLUPHENAZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
13 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2313572 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
FLUPHENAZINE plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.6% |
FLUPHENAZINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
21 mg 1 times / day multiple, intramuscular (max) Recommended Dose: 21 mg, 1 times / day Route: intramuscular Route: multiple Dose: 21 mg, 1 times / day Sources: Page: p.315 |
unhealthy, 35.4+/-10.4 n = 30 Health Status: unhealthy Condition: Schizophrenia Age Group: 35.4+/-10.4 Sex: M+F Population Size: 30 Sources: Page: p.315 |
Disc. AE: Akathisia, Dyskinesia... AEs leading to discontinuation/dose reduction: Akathisia (3.3%) Sources: Page: p.315Dyskinesia (3.3%) Hypertonia (3.3%) Stupor (3.3%) |
250 mg 1 times / week multiple, intramuscular Highest studied dose Dose: 250 mg, 1 times / week Route: intramuscular Route: multiple Dose: 250 mg, 1 times / week Sources: Page: p.1438 |
unhealthy, 44 n = 25 Health Status: unhealthy Condition: Schizophrenia Age Group: 44 Sex: M+F Population Size: 25 Sources: Page: p.1438 |
|
100 mg single, intramuscular|subcutaneous Recommended Dose: 100 mg Route: intramuscular|subcutaneous Route: single Dose: 100 mg Sources: |
unhealthy Health Status: unhealthy Condition: Schizophrenia Sources: |
Disc. AE: Tardive dyskinesia, Neuroleptic malignant syndrome... AEs leading to discontinuation/dose reduction: Tardive dyskinesia Sources: Neuroleptic malignant syndrome Fall |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Akathisia | 3.3% Disc. AE |
21 mg 1 times / day multiple, intramuscular (max) Recommended Dose: 21 mg, 1 times / day Route: intramuscular Route: multiple Dose: 21 mg, 1 times / day Sources: Page: p.315 |
unhealthy, 35.4+/-10.4 n = 30 Health Status: unhealthy Condition: Schizophrenia Age Group: 35.4+/-10.4 Sex: M+F Population Size: 30 Sources: Page: p.315 |
Dyskinesia | 3.3% Disc. AE |
21 mg 1 times / day multiple, intramuscular (max) Recommended Dose: 21 mg, 1 times / day Route: intramuscular Route: multiple Dose: 21 mg, 1 times / day Sources: Page: p.315 |
unhealthy, 35.4+/-10.4 n = 30 Health Status: unhealthy Condition: Schizophrenia Age Group: 35.4+/-10.4 Sex: M+F Population Size: 30 Sources: Page: p.315 |
Hypertonia | 3.3% Disc. AE |
21 mg 1 times / day multiple, intramuscular (max) Recommended Dose: 21 mg, 1 times / day Route: intramuscular Route: multiple Dose: 21 mg, 1 times / day Sources: Page: p.315 |
unhealthy, 35.4+/-10.4 n = 30 Health Status: unhealthy Condition: Schizophrenia Age Group: 35.4+/-10.4 Sex: M+F Population Size: 30 Sources: Page: p.315 |
Stupor | 3.3% Disc. AE |
21 mg 1 times / day multiple, intramuscular (max) Recommended Dose: 21 mg, 1 times / day Route: intramuscular Route: multiple Dose: 21 mg, 1 times / day Sources: Page: p.315 |
unhealthy, 35.4+/-10.4 n = 30 Health Status: unhealthy Condition: Schizophrenia Age Group: 35.4+/-10.4 Sex: M+F Population Size: 30 Sources: Page: p.315 |
Fall | Disc. AE | 100 mg single, intramuscular|subcutaneous Recommended Dose: 100 mg Route: intramuscular|subcutaneous Route: single Dose: 100 mg Sources: |
unhealthy Health Status: unhealthy Condition: Schizophrenia Sources: |
Neuroleptic malignant syndrome | Disc. AE | 100 mg single, intramuscular|subcutaneous Recommended Dose: 100 mg Route: intramuscular|subcutaneous Route: single Dose: 100 mg Sources: |
unhealthy Health Status: unhealthy Condition: Schizophrenia Sources: |
Tardive dyskinesia | Disc. AE | 100 mg single, intramuscular|subcutaneous Recommended Dose: 100 mg Route: intramuscular|subcutaneous Route: single Dose: 100 mg Sources: |
unhealthy Health Status: unhealthy Condition: Schizophrenia Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
moderate [Ki 40.2 uM] | ||||
Page: 5.0 |
weak [IC50 398.1 uM] | |||
Page: 5.0 |
weak [IC50 441.2 uM] | |||
yes [Ki 9.4 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | ||||
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/23395964/ Page: 7.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Dystonic reactions to phenothiazine derivatives. | 1966 Oct |
|
Side effects of parenteral long-acting phenothiazines. | 1972 Jan 22 |
|
The therapeutic use of diazepam for akathisia. | 1973 Jul-Aug |
|
Maintenance treatment of schizophrenia with long-acting fluphenazine. | 1974 Aug |
|
Phenothiazine-induced decompensation. | 1974 Jan |
|
Schizophrenia-like reaction to diethylpropion. | 1976 Nov 27 |
|
Dystonic reaction to high dose propranolol. | 1977 Oct 29 |
|
High vs standard dosage fluphenazine HCL in acute schizophrenia. | 1978 Nov |
|
Phenothiazine-induced dystonic reaction while swimming. | 1978 Oct 21 |
|
Sleep disturbance associated with fluphenazine HCl: a case report. | 1979 Jul |
|
Benztropine prophylaxis of dystonic reactions. | 1979 Mar 28 |
|
Delirium associated with combined fluphenazine-clonidine therapy. | 1979 May |
|
behavior of rats and mice administered active metabolites of fluphenazine, 7-hydroxy-fluphenazine and fluphenazine-sulfoxide. | 1980 Nov |
|
Fluphenazine pharmacokinetics and therapeutic response. | 1981 |
|
Intrauterine effect of phenothiazines. | 1981 Apr 18 |
|
Stuttering: an unusual side effect of phenothiazines. | 1981 Mar |
|
Neuroleptic-induced seizures. An in vitro technique for assessing relative risk. | 1982 Feb |
|
Sexual dysfunction in women using major tranquilizers. | 1982 Sep |
|
A case of neuroleptic malignant syndrome successfully treated with amantadine. | 1982 Sep |
|
Neuroleptic malignant syndrome: successful treatment with dantrolene and bromocriptine. | 1983 Jul |
|
Occurrence of neuroleptic malignant syndrome in a narcoleptic patient. | 1983 Jun |
|
Neuroleptic malignant syndrome. | 1984 Jan 7 |
|
[Malignant neuroleptics syndrome]. | 1984 Mar 9 |
|
Sigma opiates and certain antipsychotic drugs mutually inhibit (+)-[3H] SKF 10,047 and [3H]haloperidol binding in guinea pig brain membranes. | 1984 Sep |
|
[Catatonia due to fluphenazine]. | 1986 Apr 1 |
|
A case of neuroleptic malignant syndrome in a mentally retarded adolescent. | 1986 Nov |
|
Effects of the 5-HT3 receptor antagonist, GR38032F, on raised dopaminergic activity in the mesolimbic system of the rat and marmoset brain. | 1987 Dec |
|
Drug-induced dystonia in young and elderly patients. | 1988 Jul |
|
[Repeated acute dystonia following administration of metoclopramide and fluphenazine]. | 1988 Mar 14 |
|
Prolonged fever without extrapyramidal symptoms during neuroleptic treatment. | 1989 Jun |
|
Propranolol withdrawal in psychosis. | 1990 Apr |
|
Fluphenazine dose, clinical response, and extrapyramidal symptoms during acute treatment. | 1990 Aug |
|
Affective disorder following use of phenylpropanolamine. | 1990 Mar |
|
Actions of ORG 5222 as a novel psychotropic agent. | 1990 Mar |
|
Interaction between fluoxetine and neuroleptics. | 1993 May |
|
Central effects of SL 82.0715, an antagonist of polyamine site of the NMDA receptor complex. | 1993 Sep-Dec |
|
The natural course of pseudotumor cerebri in lithium-treated patients. | 1994 Aug |
|
Relation of plasma fluphenazine levels to treatment response and extrapyramidal side effects in first-episode schizophrenic patients. | 1994 Jan |
|
Binding of typical and atypical antipsychotic agents to 5-hydroxytryptamine-6 and 5-hydroxytryptamine-7 receptors. | 1994 Mar |
|
Effects of concomitant risperidone and lithium treatment. | 1995 Jul |
|
Some behavioral effects of CNQX AND NBQX, AMPA receptor antagonists. | 1995 Jul-Aug |
|
Fluphenazine plasma levels, dosage, efficacy, and side effects. | 1995 May |
|
Some central effects of GYKI 52466, a non-competitive AMPA receptor antagonist. | 1995 Nov-Dec |
|
Roxindole, a potential antidepressant. I. Effect on the dopamine system. | 1996 |
|
Tardive dyskinesia induced by risperidone? | 1996 Jun |
|
An insight into the sialotranscriptome of the brown dog tick, Rhipicephalus sanguineus. | 2010 Jul 22 |
|
[A case of drug-induced syndrome of inappropriate secretion of antidiuretic hormone]. | 2010 Jul-Aug |
|
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
|
Antitubercular pharmacodynamics of phenothiazines. | 2013 Apr |
|
Phenothiazines inhibit hepatitis C virus entry, likely by increasing the fluidity of cholesterol-rich membranes. | 2013 Jun |
Patents
Sample Use Guides
For most patients, a dose of 12.5 to 25 mg (0.5 to 1 mL) may be given to initiate therapy.
Route of Administration:
Intramuscular
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8302284
30uM Fluphenazine inhibited the high-threshold Ca2 channel current in rat sympathetic neurons (blocking by 66%).
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 05:45:42 UTC 2021
by
admin
on
Sat Jun 26 05:45:42 UTC 2021
|
Record UNII |
S79426A41Z
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NDF-RT |
N0000007544
Created by
admin on Sat Jun 26 05:45:43 UTC 2021 , Edited by admin on Sat Jun 26 05:45:43 UTC 2021
|
||
|
WHO-ATC |
N05AB02
Created by
admin on Sat Jun 26 05:45:43 UTC 2021 , Edited by admin on Sat Jun 26 05:45:43 UTC 2021
|
||
|
WHO-VATC |
QN05AB02
Created by
admin on Sat Jun 26 05:45:43 UTC 2021 , Edited by admin on Sat Jun 26 05:45:43 UTC 2021
|
||
|
NDF-RT |
N0000007544
Created by
admin on Sat Jun 26 05:45:43 UTC 2021 , Edited by admin on Sat Jun 26 05:45:43 UTC 2021
|
||
|
NCI_THESAURUS |
C29710
Created by
admin on Sat Jun 26 05:45:43 UTC 2021 , Edited by admin on Sat Jun 26 05:45:43 UTC 2021
|
||
|
LIVERTOX |
426
Created by
admin on Sat Jun 26 05:45:43 UTC 2021 , Edited by admin on Sat Jun 26 05:45:43 UTC 2021
|
||
|
NDF-RT |
N0000175746
Created by
admin on Sat Jun 26 05:45:43 UTC 2021 , Edited by admin on Sat Jun 26 05:45:43 UTC 2021
|
||
|
NDF-RT |
N0000007544
Created by
admin on Sat Jun 26 05:45:43 UTC 2021 , Edited by admin on Sat Jun 26 05:45:43 UTC 2021
|
||
|
WHO-ESSENTIAL MEDICINES LIST |
24.1
Created by
admin on Sat Jun 26 05:45:43 UTC 2021 , Edited by admin on Sat Jun 26 05:45:43 UTC 2021
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
CHEMBL726
Created by
admin on Sat Jun 26 05:45:43 UTC 2021 , Edited by admin on Sat Jun 26 05:45:43 UTC 2021
|
PRIMARY | |||
|
69-23-8
Created by
admin on Sat Jun 26 05:45:43 UTC 2021 , Edited by admin on Sat Jun 26 05:45:43 UTC 2021
|
PRIMARY | |||
|
Fluphenazine
Created by
admin on Sat Jun 26 05:45:43 UTC 2021 , Edited by admin on Sat Jun 26 05:45:43 UTC 2021
|
PRIMARY | |||
|
3372
Created by
admin on Sat Jun 26 05:45:43 UTC 2021 , Edited by admin on Sat Jun 26 05:45:43 UTC 2021
|
PRIMARY | |||
|
4496
Created by
admin on Sat Jun 26 05:45:43 UTC 2021 , Edited by admin on Sat Jun 26 05:45:43 UTC 2021
|
PRIMARY | RxNorm | ||
|
1212
Created by
admin on Sat Jun 26 05:45:43 UTC 2021 , Edited by admin on Sat Jun 26 05:45:43 UTC 2021
|
PRIMARY | |||
|
CHEMBL1200951
Created by
admin on Sat Jun 26 05:45:43 UTC 2021 , Edited by admin on Sat Jun 26 05:45:43 UTC 2021
|
PRIMARY | |||
|
S79426A41Z
Created by
admin on Sat Jun 26 05:45:43 UTC 2021 , Edited by admin on Sat Jun 26 05:45:43 UTC 2021
|
PRIMARY | |||
|
69-23-8
Created by
admin on Sat Jun 26 05:45:43 UTC 2021 , Edited by admin on Sat Jun 26 05:45:43 UTC 2021
|
PRIMARY | |||
|
DB00623
Created by
admin on Sat Jun 26 05:45:43 UTC 2021 , Edited by admin on Sat Jun 26 05:45:43 UTC 2021
|
PRIMARY | |||
|
204
Created by
admin on Sat Jun 26 05:45:43 UTC 2021 , Edited by admin on Sat Jun 26 05:45:43 UTC 2021
|
PRIMARY | |||
|
M5490
Created by
admin on Sat Jun 26 05:45:43 UTC 2021 , Edited by admin on Sat Jun 26 05:45:43 UTC 2021
|
PRIMARY | Merck Index | ||
|
946
Created by
admin on Sat Jun 26 05:45:43 UTC 2021 , Edited by admin on Sat Jun 26 05:45:43 UTC 2021
|
PRIMARY | |||
|
C47536
Created by
admin on Sat Jun 26 05:45:43 UTC 2021 , Edited by admin on Sat Jun 26 05:45:43 UTC 2021
|
PRIMARY | |||
|
3334
Created by
admin on Sat Jun 26 05:45:43 UTC 2021 , Edited by admin on Sat Jun 26 05:45:43 UTC 2021
|
PRIMARY | |||
|
SUB07730MIG
Created by
admin on Sat Jun 26 05:45:43 UTC 2021 , Edited by admin on Sat Jun 26 05:45:43 UTC 2021
|
PRIMARY | |||
|
200-702-9
Created by
admin on Sat Jun 26 05:45:43 UTC 2021 , Edited by admin on Sat Jun 26 05:45:43 UTC 2021
|
PRIMARY | |||
|
D005476
Created by
admin on Sat Jun 26 05:45:43 UTC 2021 , Edited by admin on Sat Jun 26 05:45:43 UTC 2021
|
PRIMARY | |||
|
FLUPHENAZINE
Created by
admin on Sat Jun 26 05:45:43 UTC 2021 , Edited by admin on Sat Jun 26 05:45:43 UTC 2021
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
SALT/SOLVATE -> PARENT | |||
|
SALT/SOLVATE -> PARENT | |||
|
BINDER->LIGAND |
BINDING
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE -> PARENT |
Related Record | Type | Details | ||
---|---|---|---|---|
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |