Benfluorex

Identification

Name
Benfluorex
Accession Number
DB09022
Type
Small Molecule
Groups
Investigational, Withdrawn
Description

Benfluorex is an anorectic and hypolipidemic agent that is structurally related to fenfluramine. It was patented and manufactured by a French pharmaceutical company Servier.

On 18 December 2009, the European Medicines Agency (EMEA) recommended the withdrawal of all medicines containing benfluorex in the European Union, because their risks, particularly the risk of heart valve disease (fenfluramine-like cardiovascular side-effects), are greater than their benefits.

Structure
Thumb
Synonyms
  • Benfluorexum
External IDs
JP 992 / S 780 / SE 780
Product Ingredients
IngredientUNIICASInChI Key
Benfluorex HydrochlorideX7O165XZ0023642-66-2NLOALSPYZIIXEO-UHFFFAOYSA-N
International/Other Brands
Axal (CCM) / Lipascor (Servier) / Mediaxal (Servier) / Mediaxal (Servier)
Categories
UNII
403FO0NQG3
CAS number
23602-78-0
Weight
Average: 351.3628
Monoisotopic: 351.144613504
Chemical Formula
C19H20F3NO2
InChI Key
CJAVTWRYCDNHSM-UHFFFAOYSA-N
InChI
InChI=1S/C19H20F3NO2/c1-14(12-15-6-5-9-17(13-15)19(20,21)22)23-10-11-25-18(24)16-7-3-2-4-8-16/h2-9,13-14,23H,10-12H2,1H3
IUPAC Name
2-({1-[3-(trifluoromethyl)phenyl]propan-2-yl}amino)ethyl benzoate
SMILES
CC(CC1=CC(=CC=C1)C(F)(F)F)NCCOC(=O)C1=CC=CC=C1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AcetazolamideThe therapeutic efficacy of Benfluorex can be increased when used in combination with Acetazolamide.
Acetylsalicylic acidAcetylsalicylic acid may increase the hypoglycemic activities of Benfluorex.
AmcinonideThe therapeutic efficacy of Benfluorex can be decreased when used in combination with Amcinonide.
Aminosalicylic AcidAminosalicylic Acid may increase the hypoglycemic activities of Benfluorex.
AmitriptylineAmitriptyline may decrease the hypoglycemic activities of Benfluorex.
AmoxapineAmoxapine may decrease the hypoglycemic activities of Benfluorex.
ArticaineThe therapeutic efficacy of Benfluorex can be decreased when used in combination with Articaine.
BendroflumethiazideThe therapeutic efficacy of Benfluorex can be decreased when used in combination with Bendroflumethiazide.
BetamethasoneThe therapeutic efficacy of Benfluorex can be decreased when used in combination with Betamethasone.
BumetanideThe therapeutic efficacy of Benfluorex can be decreased when used in combination with Bumetanide.
Food Interactions
Not Available

References

Synthesis Reference

U.S. Patent 3,607,909.

General References
  1. Moulin P, Andre M, Alawi H, dos Santos LC, Khalid AK, Koev D, Moore R, Serban V, Picandet B, Francillard M: Efficacy of benfluorex in combination with sulfonylurea in type 2 diabetic patients: an 18-week, randomized, double-blind study. Diabetes Care. 2006 Mar;29(3):515-20. [PubMed:16505498]
  2. Roger P, Auclair J, Drain P: Addition of benfluorex to biguanide improves glycemic control in obese non-insulin-dependent diabetes: a double-blind study versus placebo. J Diabetes Complications. 1999 Mar-Apr;13(2):62-7. [PubMed:10432168]
  3. Weissman NJ: Appetite suppressants and valvular heart disease. Am J Med Sci. 2001 Apr;321(4):285-91. [PubMed:11307869]
External Links
KEGG Drug
D07192
PubChem Compound
2318
PubChem Substance
310264978
ChemSpider
2228
ChEBI
93826
ChEMBL
CHEMBL400599
Drugs.com
Drugs.com Drug Page
Wikipedia
Benfluorex
ATC Codes
A10BX06 — Benfluorex

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2Unknown StatusTreatmentType 2 Diabetes Mellitus1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00128 mg/mLALOGPS
logP4.26ALOGPS
logP4.92ChemAxon
logS-5.4ALOGPS
pKa (Strongest Basic)9.14ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.33 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity90.57 m3·mol-1ChemAxon
Polarizability34.83 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-2910000000-9d514cebe36c513591b0

Taxonomy

Description
This compound belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Benzoic acid esters
Alternative Parents
Trifluoromethylbenzenes / Amphetamines and derivatives / Phenylpropanes / Benzoyl derivatives / Aralkylamines / Carboxylic acid esters / Amino acids and derivatives / Monocarboxylic acids and derivatives / Dialkylamines / Organopnictogen compounds
show 5 more
Substituents
Amphetamine or derivatives / Benzoate ester / Trifluoromethylbenzene / Phenylpropane / Benzoyl / Aralkylamine / Amino acid or derivatives / Carboxylic acid ester / Secondary amine / Carboxylic acid derivative
show 15 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Drug created on June 25, 2014 10:57 / Updated on October 01, 2018 16:33