Structure via PubChem · Public domain (PubChem)
(RS)-fenfluramine
Sign in to saveAlso known as (+-)-fenfluramine, 3-(trifluoromethyl)-N-ethyl-alpha-methylphenethylamine, N-ethyl-alpha-methyl-3-trifluoromethylphenethylamine, 2-ethylamino-1-(3-trifluoromethylphenyl)propane, 1-(m-trifluoromethyl-phenyl)-2-ethylaminopropane
Fenfluramine, sold under the brand name Fintepla, is a serotonergic medication used for the treatment of seizures associated with Dravet syndrome and Lennox–Gastaut syndrome. It was formerly used as an appetite suppressant in the treatment of obesity, but was discontinued for this use due to cardiovascular toxicity before being repurposed for new indications. Fenfluramine was used for weight loss both alone under the brand name Pondimin and in combination with phentermine commonly known as fen-phen.
Key facts
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 461099604
- Drug.image
- Fenfluramine2DCSD.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 225px
- Drug.imageL
- Arfenfluramine.png
- Drug.image_classL
- bg-transparent
- Drug.widthL
- 125px
- Drug.imageR
- Esfenfluramine.png
- Drug.image_classR
- bg-transparent
- Drug.widthR
- 125px
- Drug.caption2
- Ball-and-stick models of fenfluramine, showing the dextro isomer above and the levo isomer below
- Drug.chirality
- Racemic mixture
- Drug.tradename
- Seizures: FinteplaWeight loss: Pondimin, Ponderax, Ponderal, others
- Drug.MedlinePlus
- a620045
- Drug.DailyMedID
- Fenfluramine
- Drug.pregnancy_AU
- B2
- Drug.routes_of_administration
- By mouth
via Wikipedia infobox
Chemical data
- Formula
- C12H16F3N
- Molecular weight
- 231.26 g/mol
- IUPAC name
- N-ethyl-1-[3-(trifluoromethyl)phenyl]propan-2-amine
- SMILES
- CCNC(C)CC1=CC(=CC=C1)C(F)(F)F
- InChIKey
- DBGIVFWFUFKIQN-UHFFFAOYSA-N
- XLogP
- 3.4
- Polar surface area
- 12 Ų
- H-bond donors
- 1
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
Withdrawn- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1963
- Admin. routes
- oral
- Indications
- epilepsy, obesity, cocaine dependence, developmental and epileptic encephalopathy
via ChEMBL · EBI
Research
24 papers- Fenfluramine modulates the anti-amnesic effects induced by sigma-1 receptor agonists and neuro(active)steroids in vivo.Epilepsy & behavior : E&B · 2022
- A serotonin and melanocortin circuit mediates D-fenfluramine anorexia.The Journal of neuroscience : the official journal of the Society for Neuroscience · 2010
- Effects of low-doses of methamphetamine on d-fenfluramine-induced head-twitch response (HTR) in mice during ageing and c-fos expression in the prefrontal cortex.BMC neuroscience · 2023
- Fenfluramine treatment for Dravet syndrome: Caregiver- and clinician-reported benefits on the quality of life of patients, caregivers, and families living in Germany, Spain, Italy, and the United Kingdom.Epilepsy research · 2023
- Stereoselective Analysis of the Antiseizure Activity of Fenfluramine and Norfenfluramine in Mice: Is l-Norfenfluramine a Better Follow-Up Compound to Racemic-Fenfluramine?International journal of molecular sciences · 2024
via PubMed
Wikidata facts
- Subclass of
- medication
- Has part
- carbon
- Mass
- 231.123
Show 7 more facts
- chemical formula
- C₁₂H₁₆F₃N
- World Health Organisation international non-proprietary name
- fenfluramine
- canonical SMILES
- CCNC(C)CC1=CC(=CC=C1)C(F)(F)F
- defined daily dose
- 0.12
- subject has role
- serotonergic agent
- Commons category
- Fenfluramine
- legal status (medicine)
- boxed warning
via Wikidata · CC0
~17 min read
Encyclopedic overview
21 sectionsContents
- Medical uses
- Seizures
- Obesity
- Adverse effects
- Heart valve disease
- Overdose
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Chemistry
- History
- Society and culture
- Legal status
- Canada
- United States
- Recreational use and effects
- Research
- Social deficits
- References
- Further reading
- External links
Fenfluramine, sold under the brand name Fintepla, is a serotonergic medication used for the treatment of seizures associated with Dravet syndrome and Lennox–Gastaut syndrome. It was formerly used as an appetite suppressant in the treatment of obesity, but was discontinued for this use due to cardiovascular toxicity before being repurposed for new indications. Fenfluramine was used for weight loss both alone under the brand name Pondimin and in combination with phentermine commonly known as fen-phen.
Side effects of fenfluramine in people treated for seizures include decreased appetite, somnolence, sedation, lethargy, diarrhea, constipation, abnormal echocardiogram, fatigue, malaise, asthenia, ataxia, balance disorder, gait disturbance, increased blood pressure, drooling, excessive salivation, fever, upper respiratory tract infection, vomiting, appetite loss, weight loss, falls, and status epilepticus. Fenfluramine acts as a serotonin and norepinephrine releasing agent, agonist of the serotonin 5-HT2 receptors, and sigma σ1 receptor positive modulator. Its mechanism of action in the treatment of seizures is unknown, but may involve increased activation of certain serotonin receptors and the sigma σ1 receptor. Chemically, fenfluramine is a phenethylamine and amphetamine.
Excerpted from Wikipedia’s “(RS)-fenfluramine” article, available under the CC BY-SA 4.0 licence.