fluphenazine

Trade name: permitil

Small moleculeapproved

Approved

Sep 9, 1959

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. — NCATS

Clinical trial activity

9 trials · 9 clinical orgs · 46 marketing orgs

Phase 1

Phase 2

Phase 3

Phase 4

Earliest trial started Dec 1, 2000 (NCT00014001)

Timeline

1950s

Sep 9, 1959
Schering-Plough — Earliest FDA Approval
Sep 9, 1959
Schering — NDA Secondary Org
Sep 9, 1959
Schering-Plough — NDA Organization
Dec 23, 1959
Apothecon — NDA Secondary Org

1970s

Jun 20, 1972
Bristol-Myers Squibb — NDA Secondary Org

1980s

Nov 7, 1985
Apothecon — Marketing Organization
Apr 16, 1987
Fresenius — Marketing Organization
Oct 16, 1987
Sandoz — Marketing Organization
Aug 12, 1988
Prasco LLC — Marketing Organization
Aug 25, 1988
Lannett Company, Inc. — Marketing Organization

1990s

Aug 30, 1991
Ani Pharmaceuticals — Marketing Organization
Aug 21, 1996
Pharmaceutical Associates — Marketing Organization
Aug 30, 1996
West-Ward Pharmaceutical — Marketing Organization
Aug 30, 1996
Hikma — Marketing Organization
Sep 10, 1996
Teva — Marketing Organization
Apr 16, 1998
Hospira — Marketing Organization

2000s

Aug 17, 2001
Mylan — Marketing Organization
Jan 1, 2003
Earliest Phase 3 Sponsor(trial)
Jan 1, 2006
Earliest Phase 1 Sponsor(trial)
Jan 1, 2006
Earliest Phase 2 Sponsor(trial)

2010s

Jul 3, 2014
Par Pharmaceuticals — Marketing Organization
Jul 3, 2014
Endo Pharmaceuticals — Marketing Organization
Jul 3, 2014
PH HEALTH — Marketing Organization
Oct 17, 2017
Aurobindo Pharma — Marketing Organization
Oct 17, 2017
Eugia Pharma — Marketing Organization

2020s

Jul 9, 2020
Amneal Pharmaceuticals — Marketing Organization
Jan 7, 2021
Cerovene — Marketing Organization
Jan 7, 2021
Dr. Reddy's Laboratories — Marketing Organization
Mar 1, 2021
Novitium Pharma — Marketing Organization
May 27, 2021
Zydus Discovery DMCC — Marketing Organization
Oct 20, 2021
Enaltec — Marketing Organization
Oct 20, 2021
ZAMEER PHARMS — Marketing Organization
Oct 20, 2021
Chartwell Pharmaceuticals — Marketing Organization
Apr 1, 2022
TWi Biotechnology, Inc. — Marketing Organization
Apr 14, 2022
Taro Pharmaceuticals — Marketing Organization
Apr 14, 2022
Sun Pharmaceuticals — Marketing Organization
Jul 15, 2022
Apotex — Marketing Organization
Oct 24, 2022
Upsher-Smith Laboratories — Marketing Organization
Nov 15, 2022
Novartis — Marketing Organization
Nov 15, 2022
Esteve Labs — Marketing Organization
Jan 5, 2023
Ajanta Pharma Ltd — Marketing Organization
Mar 30, 2023
Gland Pharma Ltd — Marketing Organization
Mar 30, 2023
Fosun — Marketing Organization
Sep 11, 2023
MSN Laboratories — Marketing Organization
Nov 6, 2023
Glenmark Pharmaceuticals — Marketing Organization
Jan 22, 2024
Torrent Pharmaceuticals Limited — Marketing Organization
Jun 7, 2024
Rising Pharmaceuticals — Marketing Organization
Jul 23, 2024
Alembic — Marketing Organization
Nov 18, 2025
Hetero Labs Ltd — Marketing Organization

Indications

Approved for

Studied for

Mechanism of action

Dopamine D2 receptorANTAGONIST
DRD2 antagonist
- D(2) dopamine receptor (DRD2) ↗

Approval history

approvedSep 9, 1959

Chemistry & pharmacology

Loading structure…

SMILES

OCCN1CCN(CCCN2c3ccccc3Sc3ccc(C(F)(F)F)cc32)CC1

Mol. weight: 437.53 g/mol
Lipinski Ro5: Pass
Rule of 3: No
Chirality: Achiral Molecule
Inorganic: No
Polymer: No
Delivery: Oral, Parenteral
Availability: Prescription Only

Oral

Yes

Parenteral

Yes

Topical

Black box warning

Sources

Also known as

10-(3-(2-hydroxyethyl)piperazinopropyl)-2-(trifluoromethyl)phenothiazine
10-(3-(2-hydroxyethyl)piperazinopropyl)-2-(trifluoromethyl)phenothiazine
10-(3'-(4''-(beta-hydroxyethyl)-1''-piperazinyl)-propyl)-3-trifluoromethylphenothiazine
10-(3'-(4''-(beta-hydroxyethyl)-1''-piperazinyl)-propyl)-3-trifluoromethylphenothiazine
1-(2-hydroxyethyl)-4-(3-(trifluoromethyl-10-phenothiazinyl)propyl)-piperazine
1-(2-hydroxyethyl)-4-(3-(trifluoromethyl-10-phenothiazinyl)propyl)-piperazine
2-(4-(3-[2-(trifluoromethyl)-10h-phenothiazin-10-yl]propyl)-1-piperazinyl)ethanol
2-(4-(3-[2-(trifluoromethyl)-10h-phenothiazin-10-yl]propyl)-1-piperazinyl)ethanol
2-(trifluoromethyl)-10-(3-(1-(beta-hydroxyethyl)-4-piperazinyl)propyl)phenothiazine
2-(trifluoromethyl)-10-(3-(1-(beta-hydroxyethyl)-4-piperazinyl)propyl)phenothiazine
4-(3-(2-(trifluoromethyl)-10h-phenothiazin-10-yl)propyl)-1-piperazineethanol
4-(3-(2-(trifluoromethyl)-10h-phenothiazin-10-yl)propyl)-1-piperazineethanol
4-(3-(2-trifluoromethyl-10-phenothiazyl)-propyl)-1-piperazineethanol
4-(3-(2-trifluoromethyl-10-phenothiazyl)-propyl)-1-piperazineethanol
4-(3-(-trifluoromethyl-10-phenothiazyl)-propyl)-1-piperazineethanol
4-(3-(-trifluoromethyl-10-phenothiazyl)-propyl)-1-piperazineethanol
decazate
flufenazin
flufenazin
flufenazina
flufenazina
flufenazine decanoate
fluorfenazine
fluorfenazine
fluorfenazine
fluorophenazine
fluorophenazine
fluorophenazine
fluorophenazine decanoate
fluorphenazine
fluorphenazine
fluorphenazine
fluphenazin
fluphenazin
fluphenazine
fluphenazine
fluphenazine
fluphenazine
fluphenazine
fluphenazine
fluphenazine
fluphenazine
fluphenazine
fluphenazine
fluphénazine
fluphénazine
fluphenazine decanoate
fluphenazine decanoate
fluphenazine decanoate
fluphenazine decanoate
fluphenazine decanoate
fluphenazine decanoate
fluphenazine decanoate
fluphenazine depot
fluphenazine dihydrochloride
fluphenazine dihydrochloride
fluphenazine enantate
fluphenazine enantate
fluphenazine enanthate
fluphenazine enanthate
fluphenazine enanthate
fluphenazine enanthate
fluphenazine enanthate
fluphenazine enanthate
fluphenazine enanthate
fluphenazine enanthate
fluphenazine enanthate
fluphenazine hcl
fluphenazine hcl
fluphenazine hcl
fluphenazine hydrochloride
fluphenazine hydrochloride
fluphenazine hydrochloride
fluphenazine hydrochloride
fluphenazine maleate
fluphenazine maleate
fluphenazinum
fluphenazinum
ftorphenazine
ftorphenazine decanoate
liogen
lyogen
mirenil
modecate
modecate
modecate
modecate
modecate conc
moditen
moditen
moditen depot
moditen-depot
moditen enant
moditen enanthate
moditen enanthate
permitil
permitil
phthorphenazine
prolixin
prolixin
prolixin
prolixin decanoate
prolixin decanoate
prolixin decanoate
prolixin enanthate
prolixin enanthate
prolixin enanthate
triflumethazine
triflumethazine

Clinical trials

NCT ID	Phase	Start date	Sponsor(s)
NCT02374567	Phase 3	Jan 1, 2015	Gottfried Wilhelm Leibniz Universität Hannover
NCT02307396	Phase 4	Nov 1, 2014	Technical University of Munich
NCT02203786	Phase 2	Sep 1, 2009	Canadian Institutes of Health Research (CIHR), University of Toronto
NCT00821301	Phase 1	Dec 1, 2008	Immune Control
NCT00929578	Phase 2	Nov 1, 2008	Immune Control, Tufts University
NCT00356200	Phase 2	Jul 1, 2006	Immune Control, Tufts University
NCT00335647	Phase 1/Phase 2 (Phase 2)	Jan 1, 2006	Immune Control
NCT00161018	Phase 3	Nov 1, 2003	University of Maryland
NCT00014001	Phase 4	Dec 1, 2000	National Institute of Mental Health (NIMH), University of North Carolina at Chapel Hill

Showing 9 of 9 trials

Page 1 / 1

Organizations

Research & Development (9)

Organization	Org type	Trials	As lead sponsor	Phases	Earliest year
Immune Control	For profit	4	2	2	2006
Tufts University	Academic/Hospital	2	2	1	2006
Canadian Institutes of Health Research (CIHR)	Academic/Hospital	1	0	1	2009
Gottfried Wilhelm Leibniz Universität Hannover	Academic/Hospital	1	1	1	2015
National Institute of Mental Health (NIMH)	Government	1	1	1	2000
Technical University of Munich	Academic/Hospital	1	1	1	2014
University of Maryland	Academic/Hospital	1	1	1	2003
University of North Carolina at Chapel Hill	Academic/Hospital	1	0	1	2000
University of Toronto	Academic/Hospital	1	1	1	2009

9 organizations

Page 1 / 1

Marketing (54)

Organization	Org type	Relationship	Date
Ajanta Pharma Ltd	For profit	MKTG	Jan 5, 2023
Alembic	For profit	MKTG	Jul 23, 2024
Amneal Pharmaceuticals	For profit	MKTG	Jul 9, 2020
Ani Pharmaceuticals	For profit	MKTG	Aug 30, 1991
Ani Pharmaceuticals	For profit	SYN	Aug 30, 1991
Apotex	For profit	MKTG	Jul 15, 2022
Apothecon	For profit	NDA2	Dec 23, 1959
Apothecon	For profit	MKTG	Nov 7, 1985
Athenex, Inc.	For profit	MKTG	—
Aurobindo Pharma	For profit	MKTG	Oct 17, 2017
Bristol-Myers Squibb	For profit	NDA2	Jun 20, 1972
Cerovene	For profit	MKTG	Jan 7, 2021
Chartwell Pharmaceuticals	For profit	MKTG	Oct 20, 2021
Dr. Reddy's Laboratories	For profit	MKTG	Jan 7, 2021
Enaltec	For profit	MKTG	Oct 20, 2021
Endo Pharmaceuticals	For profit	MKTG	Jul 3, 2014
Esteve Labs	For profit	MKTG	Nov 15, 2022
Eugia Pharma	For profit	MKTG	Oct 17, 2017
Fosun	For profit	MKTG	Mar 30, 2023
Fresenius	For profit	MKTG	Apr 16, 1987
Gland Pharma Ltd	For profit	MKTG	Mar 30, 2023
Gland Pharma Ltd	For profit	SYN	Mar 30, 2023
Glenmark Pharmaceuticals	For profit	MKTG	Nov 6, 2023
Hetero Labs Ltd	For profit	MKTG	Nov 18, 2025
Hikma	For profit	MKTG	Aug 30, 1996
Hospira	For profit	MKTG	Apr 16, 1998
Lannett Company, Inc.	For profit	SYN	Aug 25, 1988
Lannett Company, Inc.	For profit	MKTG	Aug 25, 1988
MSN Laboratories	For profit	MKTG	Sep 11, 2023
MSN Laboratories	For profit	SYN	Sep 11, 2023
Mylan	For profit	SYN	Aug 12, 1988
Mylan	For profit	MKTG	Aug 17, 2001
Novartis	For profit	MKTG	Nov 15, 2022
Novitium Pharma	For profit	MKTG	Mar 1, 2021
PH HEALTH	For profit	MKTG	Jul 3, 2014
Par Pharmaceuticals	For profit	MKTG	Jul 3, 2014
Pharmaceutical Associates	For profit	MKTG	Aug 21, 1996
Prasco LLC	For profit	MKTG	Aug 12, 1988
Rising Pharmaceuticals	For profit	MKTG	Jun 7, 2024
Sandoz	For profit	MKTG	Oct 16, 1987
Schering	For profit	NDA2	Sep 9, 1959
Schering-Plough	For profit	NDA	Sep 9, 1959
Sun Pharmaceuticals	For profit	MKTG	Apr 14, 2022
TWi Biotechnology, Inc.	For profit	MKTG	Apr 1, 2022
Taro Pharmaceuticals	For profit	MKTG	Apr 14, 2022
Taro Pharmaceuticals	For profit	SYN	Apr 14, 2022
Teva	For profit	MKTG	Sep 10, 1996
Torrent Pharmaceuticals Limited	For profit	MKTG	Jan 22, 2024
Upsher-Smith Laboratories	For profit	MKTG	Oct 24, 2022
Watson Pharmaceuticals	For profit	MKTG	—
West-Ward Pharmaceutical	For profit	MKTG	Aug 30, 1996
ZAMEER PHARMS	For profit	MKTG	Oct 20, 2021
Zydus Discovery DMCC	For profit	MKTG	May 27, 2021
Zydus Discovery DMCC	For profit	SYN	May 27, 2021