NAV

Benfluorex

Identification

Generic Name
Benfluorex
DrugBank Accession Number
DB09022
Background

Benfluorex is an anorectic and hypolipidemic agent that is structurally related to fenfluramine. It was patented and manufactured by a French pharmaceutical company Servier. The European Medicines Agency (EMA) recommended withdrawing all benfluorex containing medicines on 18 December 2009. This recommendation was based on the risks (especially fenfluramine-like cardiovascular side-effects) outweighing the benefits.

Type
Small Molecule
Groups
Investigational, Withdrawn
Structure
3D
Similar Structures
Weight
Average: 351.3628
Monoisotopic: 351.144613504
Chemical Formula
C19H20F3NO2
Synonyms
  • Benfluorex
  • Benfluorexum
External IDs
  • JP 992
  • S 780
  • SE 780
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Integrate drug-drug
interactions in your software
AcarboseThe risk or severity of hypoglycemia can be increased when Acarbose is combined with Benfluorex.
AcebutololThe therapeutic efficacy of Benfluorex can be increased when used in combination with Acebutolol.
AcetazolamideThe therapeutic efficacy of Benfluorex can be increased when used in combination with Acetazolamide.
AcetohexamideThe risk or severity of hypoglycemia can be increased when Acetohexamide is combined with Benfluorex.
Acetyl sulfisoxazoleThe therapeutic efficacy of Benfluorex can be increased when used in combination with Acetyl sulfisoxazole.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Benfluorex hydrochlorideX7O165XZ0023642-66-2NLOALSPYZIIXEO-UHFFFAOYSA-N
International/Other Brands
Axal (CCM) / Lipascor (Servier) / Mediaxal (Servier)

Categories

ATC Codes
A10BX06 — Benfluorex
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Alkyl fluoride / Alkyl halide / Amine / Amino acid or derivatives / Amphetamine or derivatives / Aralkylamine / Aromatic homomonocyclic compound / Benzoate ester / Benzoyl / Carboxylic acid derivative
show 15 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
403FO0NQG3
CAS number
23602-78-0
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

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. [Article]
  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. [Article]
  3. Weissman NJ: Appetite suppressants and valvular heart disease. Am J Med Sci. 2001 Apr;321(4):285-91. [Article]
KEGG Drug
D07192
PubChem Compound
2318
PubChem Substance
310264978
ChemSpider
2228
RxNav
18880
ChEBI
93826
ChEMBL
CHEMBL400599
Drugs.com
Drugs.com Drug Page
Wikipedia
Benfluorex

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2Unknown StatusTreatmentType 2 Diabetes Mellitus1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, coated
Pill
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-MSsplash10-0a4i-1910000000-5c921f478d972c79fb4c
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-2910000000-9d514cebe36c513591b0
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0194000000-0d10f3318cf65ca6e295
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-1190000000-e761372286d64351aca9
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a59-0894000000-2ed5f52fbb8589316b62
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-056r-7930000000-705e17d29e4334f0a781
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-1920000000-c04385df19c70b66d376
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9100000000-67d1db6880a66432b2c1
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-179.6605
predicted
DeepCCS 1.0 (2019)
[M+H]+182.01851
predicted
DeepCCS 1.0 (2019)
[M+Na]+189.47804
predicted
DeepCCS 1.0 (2019)

Drug created at June 25, 2014 16:57 / Updated at December 02, 2023 07:01