FLUPHENAZINE DECANOATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C32H44F3N3O2S
Molecular Weight	591.771
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CCCCCCCCCC(=O)OCCN1CCN(CCCN2C3=CC=CC=C3SC4=CC=C(C=C24)C(F)(F)F)CC1

InChI

InChIKey=VIQCGTZFEYDQMR-UHFFFAOYSA-N

InChI=1S/C32H44F3N3O2S/c1-2-3-4-5-6-7-8-14-31(39)40-24-23-37-21-19-36(20-22-37)17-11-18-38-27-12-9-10-13-29(27)41-30-16-15-26(25-28(30)38)32(33,34)35/h9-10,12-13,15-16,25H,2-8,11,14,17-24H2,1H3

HIDE SMILES / InChI

Molecular Formula	C32H44F3N3O2S
Molecular Weight	591.771
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

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

Approval Year

Targets

Primary Target	Pharmacology	Potency
Carboxylesterase 8	Substrate 661
Dopamine D2 receptor 311	Antagonist 2,849
Serotonin 2c (5-HT2c) receptor 131	Inverse Agonist 85	1.412 µM [EC50]
Adrenergic receptor alpha-1 171	Antagonist 2,849
Dopamine D1 receptor 106	Antagonist 2,849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 305	Primary		Approved 8,583	FLUPHENAZINE DECANOATE

C_max

Value	Dose	Analyte	Population
1.2 ng/mL	11.1 mg single, oral	FLUPHENAZINE plasma	Homo sapiens
5.92 ng/mL	18.5 mg 1 times / day steady-state, oral	FLUPHENAZINE plasma	Homo sapiens
0.519 ng/mL	8.57 mg single, oral	FLUPHENAZINE plasma	Homo sapiens
0.52 ng/mL	9.25 mg single, oral	FLUPHENAZINE plasma	Homo sapiens
2.3 ng/mL	11.1 mg single, oral	FLUPHENAZINE plasma	Homo sapiens
261 ng/mL	2.31 mg single, intravenous	FLUPHENAZINE plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
15.3 ng × h/mL	11.1 mg single, oral	FLUPHENAZINE plasma	Homo sapiens
22.62 ng × h/mL	18.5 mg 1 times / day steady-state, oral	FLUPHENAZINE plasma	Homo sapiens
6.946 ng × h/mL	8.57 mg single, oral	FLUPHENAZINE plasma	Homo sapiens
6.92 ng × h/mL	9.25 mg single, oral	FLUPHENAZINE plasma	Homo sapiens
11.4 ng × h/mL	11.1 mg single, oral	FLUPHENAZINE plasma	Homo sapiens
100 ng × h/mL	2.31 mg single, intravenous	FLUPHENAZINE plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
20.3 h	11.1 mg single, oral	FLUPHENAZINE plasma	Homo sapiens
16.4 h	18.5 mg 1 times / day steady-state, oral	FLUPHENAZINE plasma	Homo sapiens
12.98 h	8.57 mg single, oral	FLUPHENAZINE plasma	Homo sapiens
13 h	9.25 mg single, oral	FLUPHENAZINE plasma	Homo sapiens
14.4 h	11.1 mg single, oral	FLUPHENAZINE plasma	Homo sapiens
12.3 h	2.31 mg single, intravenous	FLUPHENAZINE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
0.6%			FLUPHENAZINE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
21 mg 1 times / day multiple, intramuscular Recommended	unhealthy, 35.4+/-10.4	Disc. AE: Akathisia, Dyskinesia...
250 mg 1 times / week multiple, intramuscular Highest studied dose	unhealthy, 44
100 mg single, intramuscular\|subcutaneous Recommended	unhealthy	Disc. AE: Tardive dyskinesia, Neuroleptic malignant syndrome...

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AEs

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AE	Significance	Dose	Population
Akathisia	3.3% Disc. AE	21 mg 1 times / day multiple, intramuscular Recommended	unhealthy, 35.4+/-10.4
Dyskinesia	3.3% Disc. AE	21 mg 1 times / day multiple, intramuscular Recommended	unhealthy, 35.4+/-10.4
Hypertonia	3.3% Disc. AE	21 mg 1 times / day multiple, intramuscular Recommended	unhealthy, 35.4+/-10.4
Stupor	3.3% Disc. AE	21 mg 1 times / day multiple, intramuscular Recommended	unhealthy, 35.4+/-10.4
Fall	Disc. AE	100 mg single, intramuscular\|subcutaneous Recommended	unhealthy

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,946 inhibitor 2,252	inhibitor 2,438	substrate 1,388 inhibitor 2,507	inhibitor 2,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2,153	CYP2C19 1,119

Drug as perpetrator

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Target	Modality	Activity
CYP1A2 2,333	inhibitor 4,027	moderate [Ki 40.2 uM]
CYP2C9 2,497	inhibitor 4,027	weak [IC50 398.1 uM]
CYP3A4 2,633	inhibitor 4,027	weak [IC50 441.2 uM]
CYP2D6 2,546	inhibitor 4,027	yes [Ki 9.4 uM]

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Drug as victim

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Target	Modality	Activity
CYP2C19 1,119	substrate 4,014	yes
CYP2D6 1,388	substrate 4,014	yes
CYP3A4 1,946	substrate 4,014	yes

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2,263	inhibitor 2,237

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:5123	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:5123
ChemicalBook	CB7107784	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7107784
eMolecules	732810	https://www.emolecules.com/cgi-bin/more?vid=732810
MolPort	MolPort-001-727-938	https://www.molport.com/shop/molecule-link/MolPort-001-727-938
ZINC	ZINC000019203912	http://zinc15.docking.org/substances/ZINC000019203912

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PubMed

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Title	Date	PubMed
Dystonic reactions to phenothiazine derivatives.	1966 Oct	5957732
Side effects of parenteral long-acting phenothiazines.	1972 Jan 22	5058734
Maintenance treatment of schizophrenia with long-acting fluphenazine.	1974 Aug	4154028
Phenothiazine-induced decompensation.	1974 Jan	4587065
Dystonic reaction to high dose propranolol.	1977 Oct 29	589060