Structure via PubChem · Public domain (PubChem)
benfluorex
Sign in to saveAlso known as Benfluorexum, Mediator
Benfluorex, sold under the brand name Mediator, is an anorectic and hypolipidemic agent that is structurally related to fenfluramine (a substituted amphetamine). It acts mostly as a prodrug of norfenfluramine. It was fraudulently claimed to improve glycemic control and decrease insulin resistance in people with poorly controlled type-2 diabetes through norfenfluramine acting as a 5-HT2B receptor agonist
Key facts
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 413885213
- Drug.IUPAC_name
- (RS)-2-({1-[3-(trifluoromethyl)phenyl]propan- 2-yl}amino)ethyl benzoate
- Drug.image
- Benfluorex structure.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 250px
- Drug.chirality
- Racemic mixture
- Drug.tradename
- Mediator
- Drug.legal_BR
- C1
- Drug.routes_of_administration
- By mouth
- Drug.excretion
- Kidney
- Drug.CAS_number
- 23602-78-0
- Drug.ATC_prefix
- A10
- Drug.ATC_suffix
- BX06
- Drug.PubChem
- 2318
- Drug.DrugBank
- DB09022
- Drug.ChemSpiderID
- 2228
via Wikipedia infobox
Chemical data
- Formula
- C19H20F3NO2
- Molecular weight
- 351.4 g/mol
- IUPAC name
- 2-[1-[3-(trifluoromethyl)phenyl]propan-2-ylamino]ethyl benzoate
- SMILES
- CC(CC1=CC(=CC=C1)C(F)(F)F)NCCOC(=O)C2=CC=CC=C2
- InChIKey
- CJAVTWRYCDNHSM-UHFFFAOYSA-N
- XLogP
- 4.6
- Polar surface area
- 38.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
Withdrawn- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1974
- Indications
- diabetes mellitus, type 2 diabetes mellitus
via ChEMBL · EBI
Research
216 papers- Benfluorex and Valvular Heart Disease.Pharmacoepidemiology and drug safety · 2024
- [Benfluorex and valvular heart disease].Presse medicale (Paris, France : 1983) · 2011
- Benfluorex metabolism complemented by electrochemistry-mass spectrometry.Journal of pharmaceutical and biomedical analysis · 2023
- Adverse effects of benfluorex on heart valves and pulmonary circulation.Pharmacoepidemiology and drug safety · 2014
- Benfluorex: analysis of a drug-related public health crisis.Diabetes & metabolism · 2011
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 351.145
- Has use
- medication
Show 5 more facts
- chemical formula
- C₁₉H₂₀F₃NO₂
- Commons category
- Benfluorex
- canonical SMILES
- CC(CC1=CC(=CC=C1)C(F)(F)F)NCCOC(=O)C2=CC=CC=C2
- defined daily dose
- 0.45
- subject has role
- anorectic
Sources (3)
via Wikidata · CC0
~5 min read
Encyclopedic overview
2 sectionsContents
- Drug withdrawn
- References
{{Infobox drug | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 413885213 | IUPAC_name = (RS)-2-({1-[3-(trifluoromethyl)phenyl]propan- 2-yl}amino)ethyl benzoate | image = Benfluorex structure.svg | image_class = skin-invert-image | width = 250px | chirality = Racemic mixture
| tradename = Mediator | Drugs.com = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_BR = C1 | legal_BR_comment = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = By mouth
Excerpted from Wikipedia’s “benfluorex” article, available under the CC BY-SA 4.0 licence.