Structure via PubChem · Public domain (PubChem)
fluphenazine
Sign in to saveAlso known as 2-(4-{3-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]propyl}-1-piperazinyl)ethanol, 4-[3-(2-trifluoromethyl-10-phenothiazyl)-propyl]-1-piperazineethanol, 4-{3-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]propyl}-1-piperazineethanol, 4-[3-(-trifluoromethyl-10-phenothiazyl)-propyl]-1-piperazineethanol, 2-(trifluoromethyl)-10-{3-[1-(beta-hydroxyethyl)-4-piperazinyl]propyl}phenothiazine, 10-[3-(2-hydroxyethyl)piperazinopropyl]-2-(trifluoromethyl)phenothiazine, 10-{3′-[4″-(beta-hydroxyethyl)-1″-piperazinyl]-propyl}-3-trifluoromethylphenothiazine, 1-(2-hydroxyethyl)-4-[3-(trifluoromethyl-10-phenothiazinyl)propyl]-piperazine
Fluphenazine, sold under the brand name Prolixin among others, is a high-potency typical antipsychotic medication of the phenothiazine class. It is used in the treatment of chronic psychoses such as schizophrenia, and is about equal in effectiveness to low-potency antipsychotics like chlorpromazine. It is also used to treat depression in combination with nortriptyline. In addition to the oral form, fluphenazine comes in decanoate and enanthate depot injection versions for increased adherence. Fluphenazine is given by mouth, intramuscularly, or just under the skin.
Key facts
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 443824001
- Drug.image
- Fluphenazine.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 250
- Drug.image2
- Fluphenazine_3D_Ball-and-Stick.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 175
- Drug.tradename
- Prolixin, Modecate, Moditen others
- Drug.MedlinePlus
- a682172
- Drug.DailyMedID
- Fluphenazine
- Drug.pregnancy_AU
- C
- Drug.routes_of_administration
- By mouth, Intramuscular injection, depot injection (fluphenazine decanoate)
- Drug.class
- Typical antipsychotic
- Drug.ATC_prefix
- N05
- Drug.ATC_suffix
- AB02
- Drug.legal_BR
- C1
- Drug.legal_CA
- Rx-only
via Wikipedia infobox
Chemical data
- Formula
- C22H26F3N3OS
- Molecular weight
- 437.5 g/mol
- IUPAC name
- 2-[4-[3-[2-(trifluoromethyl)phenothiazin-10-yl]propyl]piperazin-1-yl]ethanol
- SMILES
- C1CN(CCN1CCCN2C3=CC=CC=C3SC4=C2C=C(C=C4)C(F)(F)F)CCO
- InChIKey
- PLDUPXSUYLZYBN-UHFFFAOYSA-N
- XLogP
- 4.4
- Polar surface area
- 55.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1959
- Admin. routes
- oral, parenteral
- Indications
- psychosis, schizophrenia
via ChEMBL · EBI
Research
3,325 papers- Fluphenazine versus low-potency first-generation antipsychotic drugs for schizophrenia.The Cochrane database of systematic reviews · 2014
- Should we be Prescribing Fluphenazine Long-Acting Injectable Formulation?Current psychiatry reports · 2025
- [FLUPHENAZINE].Ceskoslovenska psychiatrie · 1965
- Fluphenazine decanoate (depot) and enanthate for schizophrenia.The Cochrane database of systematic reviews · 2015
- Depot fluphenazine: risk/benefit ratio.The Journal of clinical psychiatry · 1984
via PubMed
Wikidata facts
- Subclass of
- primary alcohol
- Has part
- fluorine
- Mass
- 437.174868
- Has use
- medication
Show 11 more facts
- chemical formula
- C₂₂H₂₆F₃N₃OS
- defined daily dose
- 1
- medical condition treated
- schizophrenia
- canonical SMILES
- C1CN(CCN1CCCN2C3=CC=CC=C3SC4=C2C=C(C=C4)C(F)(F)F)CCO
- World Health Organisation international non-proprietary name
- fluphenazine
- Commons category
- Fluphenazine
- subject has role
- essential medicine
- physically interacts with
- Histamine receptor H1
- route of administration
- intramuscular injection
- significant drug interaction
- loxapine
- stylized name
- fluPHENAZine
Sources (7)
via Wikidata · CC0
~7 min read
Encyclopedic overview
9 sectionsContents
- Medical use
- Side effects
- Discontinuation
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Availability
- Veterinary
- References
Fluphenazine, sold under the brand name Prolixin among others, is a high-potency typical antipsychotic medication of the phenothiazine class. It is used in the treatment of chronic psychoses such as schizophrenia, and is about equal in effectiveness to low-potency antipsychotics like chlorpromazine. It is also used to treat depression in combination with nortriptyline. In addition to the oral form, fluphenazine comes in decanoate and enanthate depot injection versions for increased adherence. Fluphenazine is given by mouth, intramuscularly, or just under the skin.
Common side effects include movement problems, sleepiness, depression and increased weight. Serious side effects may include neuroleptic malignant syndrome, low white blood cell levels, and the potentially permanent movement disorder tardive dyskinesia. In older people with psychosis as a result of dementia it may increase the risk of dying. It may also increase prolactin levels which may result in milk production, enlarged breasts in males, impotence, and the absence of menstrual periods. It is unclear if it is safe for use in pregnancy. Fluphenazine decanoate should not be used by people with severe depression. In up to 40% of those on long term phenothiazines, liver function tests become mildly abnormal.
Excerpted from Wikipedia’s “fluphenazine” article, available under the CC BY-SA 4.0 licence.