Structure via PubChem · Public domain (PubChem)
trifluoperazine
Sign in to saveAlso known as Eskazinyl®, Stelazine®, trifluoperazine hydrochloride, 10-[3-(4-Methyl-1-piperazinyl)propyl]-2-(trifluoromethyl)-10H-phenothiazine, Trifluoromethyl-10-(3'-(1-methyl-4-piperazinyl)propyl)phenothiazine, Trifluoperazinum, Trifluperazine, 10-[3-(4-METHYL-piperazin-1-yl)-propyl]-2-trifluoromethyl-10H-phenothiazine
Trifluoperazine, marketed under the brand name Stelazine among others, is a typical antipsychotic primarily used to treat schizophrenia. It may also be used short term in those with generalized anxiety disorder but is less preferred to benzodiazepines. It is of the phenothiazine chemical class. It was approved for medical use in the United States in 1959.
Chemical data
- Formula
- C21H24F3N3S
- Molecular weight
- 407.5 g/mol
- IUPAC name
- 10-[3-(4-methylpiperazin-1-yl)propyl]-2-(trifluoromethyl)phenothiazine
- SMILES
- CN1CCN(CC1)CCCN2C3=CC=CC=C3SC4=C2C=C(C=C4)C(F)(F)F
- InChIKey
- ZEWQUBUPAILYHI-UHFFFAOYSA-N
- XLogP
- 5
- Polar surface area
- 35 Ų
- H-bond donors
- 0
- H-bond acceptors
- 7
- 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, Diamond-Blackfan anemia
via ChEMBL · EBI
Research
5,313 papers- Trifluoperazine for schizophrenia.The Cochrane database of systematic reviews · 2004
- Trifluoperazine versus low-potency first-generation antipsychotic drugs for schizophrenia.The Cochrane database of systematic reviews · 2014
- Trifluoperazine overdosage.The Practitioner · 1967
- Trifluoperazine activates AMPK / mTOR / ULK1 signaling pathway to induce mitophagy in osteosarcoma cells.Chemico-biological interactions · 2024
- Trifluoperazine: A Sprightly Old Drug.Journal of psychosocial nursing and mental health services · 2016
via PubMed
Wikidata facts
- Subclass of
- alkaloid
- Has part
- carbon
- Mass
- 407.164
- Has use
- medication
Show 10 more facts
- found in taxon
- Crotalaria pallida
- chemical formula
- C₂₁H₂₄F₃N₃S
- medical condition treated
- schizophrenia
- subject has role
- antiemetic
- canonical SMILES
- CN1CCN(CC1)CCCN2C3=CC=CC=C3SC4=C2C=C(C=C4)C(F)(F)F
- World Health Organisation international non-proprietary name
- trifluoperazine
- Commons category
- Trifluoperazine
- defined daily dose
- 20
- physically interacts with
- Histamine receptor H1
- legal status (medicine)
- boxed warning
via Wikidata · CC0
~4 min read
Encyclopedic overview
8 sectionsContents
- Medical uses
- Schizophrenia
- Other
- Side effects
- Contraindications
- Mechanism of action
- Names
- References
Trifluoperazine, marketed under the brand name Stelazine among others, is a typical antipsychotic primarily used to treat schizophrenia. It may also be used short term in those with generalized anxiety disorder but is less preferred to benzodiazepines. It is of the phenothiazine chemical class. It was approved for medical use in the United States in 1959.
== Medical uses == ===Schizophrenia=== Trifluoperazine is an effective antipsychotic for people with schizophrenia condition. There is low-quality evidence that trifluoperazine increases the chance of being improved when compared to placebo when people are followed up for 19 weeks. There is low-quality evidence that trifluoperazine reduces the risk of relapse when compared with placebo when people are followed for 5 months. As of 2014 there was no good evidence for a difference between trifluoperazine and placebo with respect to the risk of experiencing intensified symptoms over a 16-week period nor in reducing significant agitation or distress.
Excerpted from Wikipedia’s “trifluoperazine” article, available under the CC BY-SA 4.0 licence.