Fluphenazine
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Fluphenazine
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Clinical data |
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Trade names |
Prolixin, Modecate, Moditen others |
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AHFS/Drugs.com
|
Monograph |
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MedlinePlus |
a682172 |
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Pregnancy category |
AU: C
US: C (Risk not ruled out)
|
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Routes of administration |
by mouth, IM, depot injection (fluphenazine decanoate) |
---|
ATC code |
|
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Legal status |
---|
Legal status |
AU: S4 (Prescription only)
CA: ℞-only
UK: POM (Prescription only)
US: ℞-only
|
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Pharmacokinetic data |
---|
Bioavailability |
2.7% (by mouth) |
---|
Metabolism |
unclear[1]
|
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Elimination half-life
|
IM 15 hours (HCL), 7-10 days (decanoate)[1]
|
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Excretion |
Urine, faeces |
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Identifiers |
---|
IUPAC name
- 2-[4-[3-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]propyl]piperazin-1-yl]ethanol
|
CAS Number |
69-23-8 Y
|
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PubChem CID
|
|
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IUPHAR/BPS |
|
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DrugBank |
DB00623 Y
|
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ChemSpider |
3255 Y
|
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UNII |
|
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KEGG |
D07977 Y
|
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ChEBI |
CHEBI:5123 Y
|
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ChEMBL |
ChEMBL726 Y
|
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ECHA InfoCard |
100.000.639
|
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Chemical and physical data |
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Formula |
C22H26F3N3OS
|
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Molar mass |
437.523 g/mol |
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3D model (JSmol) |
|
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SMILES
FC(F)(F)c2cc1N(c3c(Sc1cc2)cccc3)CCCN4CCN(CCO)CC4
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InChI
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 Y
Key:PLDUPXSUYLZYBN-UHFFFAOYSA-N Y
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.mw-parser-output .nobold{font-weight:normal}
(verify)
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Fluphenazine, sold under the brand names Prolixin among others, is an antipsychotic medication.[1] It is used in the treatment of chronic psychoses such as schizophrenia,[1][2] and appears to be about equal in effectiveness to low-potency antipsychotics like chlorpromazine.[3] It is given by mouth, injection into a muscle, or just under the skin.[1] There is also a long acting injectable version that may last for up to four weeks.[1] Fluphenazine decanoate, the depot injection form of fluphenazine, should not be used by people with severe depression.[4]
Common side effects include movement problems, sleepiness, depression and increased weight.[1] Serious side effects may include neuroleptic malignant syndrome, low white blood cell levels, and the potentially permanent movement disorder tardive dyskinesia.[1] In older people with psychosis as a result of dementia it may increase the risk of dying.[1] It may also increase prolactin levels which may result in milk production, enlarged breasts in males, impotence, and the absence of menstrual periods.[1] It is unclear if it is safe for use in pregnancy.[1] Fluphenazine is a typical antipsychotic of the phenothiazine class.[1] Its mechanism of action is not entirely clear but believed to be related to its ability to block dopamine receptors.[1] In up to 40% of those on long term phenothiazines, liver function tests become mildly abnormal.[5]
Fluphenazine came into use in 1959.[6] The injectable form is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.[7] It is available as a generic medication.[1] In the United States the tablets costs between 0.22 and 0.42 USD per day for a typical dose.[1] The wholesale cost in the developing world of the long acting form is between 0.20 and 6.20 USD per injection as of 2014.[8] It was discontinued in Australia around mid 2017.[9]
Effectiveness[edit]
A 2013 Cochrane review found that fluphenazine's was an imperfect treatment and other inexpensive drugs less associated with side effects may be an just as good in people with schizophrenia.[10]
Other animals[edit]
In horses, it is sometimes given by injection as an anxiety-relieving medication, though there are many negative common side effects and it is forbidden by many equestrian competition organizations.[11]
References[edit]
^ abcdefghijklmno "fluphenazine decanoate". The American Society of Health-System Pharmacists. Archived from the original on 2015-12-08. Retrieved Dec 1, 2015..mw-parser-output cite.citation{font-style:inherit}.mw-parser-output q{quotes:"""""""'""'"}.mw-parser-output code.cs1-code{color:inherit;background:inherit;border:inherit;padding:inherit}.mw-parser-output .cs1-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-limited a,.mw-parser-output .cs1-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration{color:#555}.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration span{border-bottom:1px dotted;cursor:help}.mw-parser-output .cs1-hidden-error{display:none;font-size:100%}.mw-parser-output .cs1-visible-error{font-size:100%}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-format{font-size:95%}.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-right{padding-right:0.2em}
^ "Product Information: Modecate (Fluphenazine Decanoate Oily Injection )" (PDF). TGA eBusiness Services. Bristol-Myers Squibb Australia Pty Ltd. 1 November 2012. Archived from the original on 2 August 2017. Retrieved 9 December 2013.
^ Tardy M, Huhn M, Engel RR, Leucht S (August 2014). "Fluphenazine versus low-potency first-generation antipsychotic drugs for schizophrenia". The Cochrane Database of Systematic Reviews. 8 (8): CD009230. doi:10.1002/14651858.CD009230.pub2. PMID 25087165.
^ "Modecate Injection 25mg/ml - Patient Information Leaflet (PIL) - (eMC)". www.medicines.org.uk. Retrieved 2017-11-06.
^ "Fluphenazine". livertox.nih.gov. Retrieved 2017-11-06.
^ McPherson EM (2007). Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Burlington: Elsevier. p. 1680. ISBN 9780815518563.
^ "WHO Model List of Essential Medicines (19th List)" (PDF). World Health Organization. April 2015. Archived (PDF) from the original on 13 December 2016. Retrieved 8 December 2016.
^ "Fluphenazine Decanoate". International Drug Price Indicator Guide. Archived from the original on 2 August 2017. Retrieved 2 December 2015.
^ Rossi S, ed. (July 2017). "Fluphenazine - Australian Medicines Handbook". Australian Medicines Handbook. Adelaide, Australia: Australian Medicines Handbook Pty Ltd. Retrieved 8 August 2017.
^ Matar, Hosam E; Almerie, Muhammad Qutayba; Sampson, Stephanie J (2018-06-12). "Fluphenazine (oral) versus placebo for schizophrenia". Cochrane Database of Systematic Reviews. doi:10.1002/14651858.cd006352.pub3. ISSN 1465-1858.
^ Loving NS (31 March 2012). "Effects of Behavior-Modifying Drug Investigated (AAEP 2011)". The Horse Media Group. Archived from the original on 6 January 2017. Retrieved 13 December 2016.
Antipsychotics (N05A)
|
---|
Typical |
Butyrophenones: Benperidol
- Bromperidol
- Droperidol
Haloperidol#
- Moperone
- Pipamperone
- Spiperone
- Timiperone
- Trifluperidol
Diphenylbutylpiperidines: Fluspirilene
- Penfluridol
- Pimozide
Phenothiazines: Acetophenazine
- Butaperazine
Carphenazine (carfenazine)‡
- Chlorpromazine
- Cyamemazine
- Dixyrazine
- Fluphenazine
- Levomepromazine (methotrimeprazine)
- Mesoridazine
- Perazine
- Periciazine
- Perphenazine
- Piperacetazine
- Pipotiazine
- Prochlorperazine
- Promazine
- Sulforidazine
- Thiopropazate
- Thioproperazine
- Thioridazine
- Trifluoperazine
- Triflupromazine
Thioxanthenes: Chlorprothixene
- Clopenthixol
- Flupentixol
- Tiotixene (thiothixene)
- Zuclopenthixol
|
---|
Disputed |
Benzamides: Amisulpride
- Levosulpiride
- Nemonapride
Remoxipride‡
- Sulpiride
- Sultopride
- Tiapride
Veralipride‡
Butyrophenones: Melperone
Tricyclics: Carpipramine
- Clocapramine
- Clorotepine
- Clotiapine
- Loxapine
- Mosapramine
|
---|
Atypical |
Benzisoxazole/benzisothiazoles: Iloperidone
- Lurasidone
- Paliperidone
- Paliperidone palmitate
- Perospirone
Risperidone#
- Ziprasidone
Butyrophenones: Lumateperone†
Phenylpiperazines/quinolinones: Aripiprazole
- Aripiprazole lauroxil
- Brexpiprazole
- Cariprazine
RP-5063†
Tricyclics: Asenapine
Clozapine#
- Olanzapine
- Quetiapine
- Zotepine
Others: Blonanserin
- Pimavanserin
- Sertindole
|
---|
Others |
- Azacyclonol
- Cannabidiol
- Oxypertine
- Reserpine
- Tetrabenazine
|
---|
#WHO-EM
‡Withdrawn from market
Clinical trials:
†Phase III
§Never to phase III
|
Pharmacodynamics |
---|
Dopamine receptor modulators
|
---|
D1-like |
Agonists |
Benzazepines: 6-Br-APB
- Fenoldopam
- SKF-38,393
- SKF-77,434
- SKF-81,297
- SKF-82,958
- SKF-83,959
- Trepipam
- Zelandopam
Ergolines: Cabergoline
- CY-208,243
- Dihydroergocryptine
- LEK-8829
- Lisuride
- Pergolide
- Terguride
Dihydrexidine derivatives: A-77636
- A-86929
- Adrogolide (ABT-431, DAS-431)
- Dihydrexidine
- Dinapsoline
- Dinoxyline
- Doxanthrine
Phenethylamines: BCO-001
- Deoxyepinephrine (N-methyldopamine, epinine)
- Dopexamine
- Etilevodopa
- Ibopamine
L-DOPA (levodopa)
- Melevodopa
L-Phenylalanine
L-Tyrosine
- XP21279
Others: A-68930
- Apomorphine
- Isocorypalmine
- Nuciferine
- PF-6649751
- PF 6669571
- Propylnorapomorphine
- Rotigotine
- SKF-89,145
- SKF-89,626
- Stepholidine
- Tetrahydropalmatine
|
---|
Antagonists |
Typical antipsychotics: Butaclamol
- Chlorpromazine
- Chlorprothixene
Flupentixol (flupenthixol) (+melitracen)
- Fluphenazine
- Loxapine
Perphenazine (+amitriptyline)
- Pifluthixol
- Thioridazine
- Thiothixene
Trifluoperazine (+tranylcypromine)
- Zuclopenthixol
Atypical antipsychotics: Asenapine
- Clorotepine
- Clotiapine
- Clozapine
- DHA-clozapine
- Fluperlapine
- Iloperidone
- Norclozapine
- Norquetiapine
Olanzapine (++fluoxetine)
- Paliperidone
- Quetiapine
- Risperidone
- Tefludazine
- Zicronapine
- Ziprasidone
- Zotepine
Others: Berupipam
- Ecopipam
- EEDQ
- Metitepine (methiothepin)
- Odapipam
- Perlapine
- SCH-23390
|
---|
|
---|
D2-like |
Agonists |
Adamantanes: Amantadine
- Memantine
- Rimantadine
Aminotetralins: 5-OH-DPAT
- 7-OH-DPAT
- 8-OH-PBZI
- Rotigotine
- UH-232
Ergolines: Bromocriptine
- Cabergoline
- Dihydroergocryptine
- Epicriptine
- Ergocornine
- Lergotrile
- Lisuride
- LSD
- Pergolide
- Terguride
Dihydrexidine derivatives: 2-OH-NPA
- Ciladopa
- Dihydrexidine
- Dinoxyline
- N,N-Propyldihydrexidine
Phenethylamines: Deoxyepinephrine (N-methyldopamine, epinine)
- Dopexamine
- Etilevodopa
- Ibopamine
L-DOPA (levodopa)
L-Phenylalanine
L-Tyrosine
- Melevodopa
- XP21279
Atypical antipsychotics: Alentemol (U-66444B)
Aripiprazole (+sertraline)
- Aripiprazole lauroxil
- Bifeprunox
- Brexpiprazole
- Cariprazine
- F-15063
- Lumateperone
- Norclozapine
- RP-5063
Others: 3-PPP
- A-412997
- ABT-670
- ABT-724
- Adrafinil
- Aplindore
- Apomorphine
- Arketamine
- Armodafinil
- BP-897
- Captodiame
- CP-226,269
- Dizocilpine
- Esketamine
- Flibanserin
- GSK-789,472
- Ketamine
- Mesulergine
- Modafinil
- OSU-6162
- Pardoprunox
- PD-128,907
- PD-168,077
- PF-219,061
- PF-592,379
- Phencyclidine
- Piribedil
- Pramipexole
- Preclamol
- Propylnorapomorphine
- Pukateine
- Quinagolide
- Quinelorane
- Quinpirole
- RDS-127
- Ro10-5824
- Ropinirole
- Roxindole
- Salvinorin A
- SKF-83,959
- Sumanirole
- Talipexole
- Umespirone
- WAY-100,635
|
---|
Antagonists |
|
---|
|
---|
- See also: Receptor/signaling modulators
- Adrenergics
- Serotonergics
- Monoamine reuptake inhibitors
- Monoamine releasing agents
- Monoamine metabolism modulators
- Monoamine neurotoxins
|
Histamine receptor modulators
|
---|
H1
|
Agonists: 2-Pyridylethylamine
- Betahistine
- Histamine
- HTMT
L-Histidine
- UR-AK49
Antagonists: First-generation: 4-Methyldiphenhydramine
- Alimemazine
- Antazoline
- Azatadine
- Bamipine
- Benzatropine (benztropine)
- Bepotastine
- Bromazine
- Brompheniramine
- Buclizine
- Captodiame
- Carbinoxamine
- Chlorcyclizine
- Chloropyramine
- Chlorothen
- Chlorphenamine
- Chlorphenoxamine
- Cinnarizine
- Clemastine
- Clobenzepam
- Clocinizine
- Cloperastine
- Cyclizine
- Cyproheptadine
- Dacemazine
- Decloxizine
- Deptropine
- Dexbrompheniramine
- Dexchlorpheniramine
- Dimenhydrinate
- Dimetindene
- Diphenhydramine
- Diphenylpyraline
- Doxylamine
- Embramine
- Etodroxizine
- Etybenzatropine (ethylbenztropine)
- Etymemazine
- Fenethazine
- Flunarizine
- Histapyrrodine
- Homochlorcyclizine
- Hydroxyethylpromethazine
- Hydroxyzine
- Isopromethazine
- Isothipendyl
- Meclozine
- Medrylamine
- Mepyramine (pyrilamine)
- Mequitazine
- Methafurylene
- Methapyrilene
- Methdilazine
- Moxastine
- Orphenadrine
- Oxatomide
- Oxomemazine
- Perlapine
- Phenindamine
- Pheniramine
- Phenyltoloxamine
- Pimethixene
- Piperoxan
- Pipoxizine
- Promethazine
- Propiomazine
- Pyrrobutamine
- Talastine
- Thenalidine
- Thenyldiamine
- Thiazinamium
- Thonzylamine
- Tolpropamine
- Tripelennamine
- Triprolidine
Second/third-generation: Acrivastine
- Alinastine
- Astemizole
- Azelastine
- Bamirastine
- Barmastine
- Bepiastine
- Bepotastine
- Bilastine
- Cabastinen
- Carebastine
- Cetirizine
- Clemastine
- Clemizole
- Clobenztropine
- Desloratadine
- Dorastine
- Ebastine
- Efletirizine
- Emedastine
- Epinastine
- Fexofenadine
- Flezelastine
- Ketotifen
- Latrepirdine
- Levocabastine
- Levocetirizine
- Linetastine
- Loratadine
- Mapinastine
- Mebhydrolin
- Mizolastine
- Moxastine
- Noberastine
- Octastine
- Olopatadine
- Perastine
- Pibaxizine
- Piclopastine
- Quifenadine (phencarol)
- Rocastine
- Rupatadine
- Setastine
- Sequifenadine (bicarphen)
- Talastine
- Temelastine
- Terfenadine
- Vapitadine
- Zepastine
Others: Atypical antipsychotics (e.g., aripiprazole, asenapine, brexpiprazole, clozapine, iloperidone, olanzapine, paliperidone, quetiapine, risperidone, RP-5063, ziprasidone, zotepine)
Phenylpiperazine antidepressants (e.g., hydroxynefazodone, nefazodone, trazodone, triazoledione)
Tetracyclic antidepressants (e.g., amoxapine, loxapine, maprotiline, mianserin, mirtazapine, oxaprotiline)
Tricyclic antidepressants (e.g., amitriptyline, butriptyline, clomipramine, desipramine, dosulepin (dothiepin), doxepin, imipramine, iprindole, lofepramine, nortriptyline, protriptyline, trimipramine)
Typical antipsychotics (e.g., chlorpromazine, flupenthixol, fluphenazine, loxapine, perphenazine, prochlorperazine, thioridazine, thiothixene)
Unknown/unsorted: Azanator
- Belarizine
- Elbanizine
- Flotrenizine
- GSK1004723
- Napactadine
- Tagorizine
- Trelnarizine
- Trenizine
|
---|
H2
|
Agonists: Amthamine
- Betazole
- Dimaprit
- Histamine
- HTMT
- Impromidine
L-Histidine
- UR-AK49
Antagonists: Bisfentidine
- Burimamide
- Cimetidine
- Dalcotidine
- Donetidine
- Ebrotidine
- Etintidine
- Famotidine
- Isolamtidine
- Lafutidine
- Lamtidine
- Lavoltidine (loxtidine)
- Lupitidine
- Metiamide
- Mifentidine
- Niperotidine
- Nizatidine
- Osutidine
- Oxmetidine
- Pibutidine
- Quisultazine (quisultidine)
- Ramixotidine
- Ranitidine
- Roxatidine
- Sufotidine
- Tiotidine
- Tuvatidine
- Venritidine
- Xaltidine
- Zolantidine
|
---|
H3
|
Agonists: α-Methylhistamine
- Cipralisant
- Histamine
- Imetit
- Immepip
- Immethridine
L-Histidine
- Methimepip
- Proxyfan
Antagonists: A-349,821
- A-423,579
- ABT-239
- ABT-652
- AZD5213
- Bavisant
- Betahistine
- Burimamide
- Ciproxifan
- Clobenpropit
- Conessine
- Enerisant
- GSK-189,254
- Impentamine
- Iodophenpropit
- Irdabisant
- JNJ-5207852
- MK-0249
- NNC 38-1049
- PF-03654746
- Pitolisant
- SCH-79687
- Thioperamide
- VUF-5681
|
---|
H4
|
Agonists: 4-Methylhistamine
- α-Methylhistamine
- Histamine
L-Histidine
- OUP-16
- VUF-8430
Antagonists: JNJ-7777120
- Mianserin
- Seliforant
- Thioperamide
- Toreforant
- VUF-6002
|
---|
See also: Receptor/signaling modulators • Monoamine metabolism modulators • Monoamine reuptake inhibitors |
Sigma receptor modulators
|
---|
σ1
|
|
---|
σ2
|
Agonists: 3-PPP
- Arketamine
- BD-1047
- BD1063
- Ditolylguanidine (DTG)
- DKR-1005
- DKR-1051
- Haloperidol
- Ifenprodil
- Ketamine
MDMA (midomafetamine)
- Methamphetamine
- OPC-14523
- Opipramol
- PB-28
- Phencyclidine
- Siramesine (Lu 28-179)
- UKH-1114
Antagonists: AC-927
- BD-1008
- BD-1067
- CM-156
- CT-1812
- LR-172
- MIN-101
- Panamesine (EMD-57455)
- SAS-0132
Unknown/unsorted: 3-Methoxydextrallorphan
- 3-MeO-PCE
- 4-MeO-PCP
- 5-MeO-DALT
- 5-MeO-DiPT
- Clemastine
- DiPT
- DPT
- Ibogaine
- Nemonapride
- Nepinalone
- Noribogaine
- Pentazocine
- RS-67,333
- Safinamide
- TMA
- UMB-23
- UMB-82
- W-18
|
---|
Unsorted |
Agonists: Berberine
- Ethylketazocine
- Fourphit
- Metaphit
- Naluzotan
- Tapentadol
- Tenocyclidine
Antagonists: AHD1
- AZ66
- Lamotrigine
- Naloxone
- SM-21
- UMB-100
- UMB-101
- UMB-103
- UMB-116
- YZ-011
- YZ-069
- YZ-185
Allosteric modulators: SKF-83959
Unknown/unsorted: 18-Methoxycoronaridine
- BMY-13980
- Butaclamol
- Caramiphen
- Carvotroline
- Chlorphenamine (chlorpheniramine)
- Chlorpromazine
- Cinnarizine
- Cinuperone
- Clocapramine
- Dezocine
- EMD-59983
Hypericin (St. John's wort)
- Fluphenazine
- Gevotroline (WY-47384)
- Mepyramine (pyrilamine)
- Molindone
- Perphenazine
- Pimozide
- Proadifen
- Promethazine
- Propranolol
- Quinidine
- Remoxipride
- SL 82.0715
- SR-31747A
- Tiospirone (BMY-13859)
- Venlafaxine
|
---|
See also: Receptor/signaling modulators |
|
Categories:
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- Sigma receptor ligands
- Trifluoromethyl compounds
- Typical antipsychotics
- World Health Organization essential medicines
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