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- Investigational, Withdrawn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
Structure for Benfluorex (DB09022)
- Weight
- Average: 351.3628
Monoisotopic: 351.144613504 - Chemical Formula
- C19H20F3NO2
- Synonyms
- Benfluorex
- Benfluorexum
- External IDs
- JP 992
- S 780
- SE 780
Pharmacology
- Indication
Not Available
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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcarbose The risk or severity of hypoglycemia can be increased when Acarbose is combined with Benfluorex. Acebutolol The therapeutic efficacy of Benfluorex can be increased when used in combination with Acebutolol. Acetazolamide The therapeutic efficacy of Benfluorex can be increased when used in combination with Acetazolamide. Acetohexamide The risk or severity of hypoglycemia can be increased when Acetohexamide is combined with Benfluorex. Acetyl sulfisoxazole The therapeutic efficacy of Benfluorex can be increased when used in combination with Acetyl sulfisoxazole. Acetylsalicylic acid The risk or severity of hypoglycemia can be increased when Acetylsalicylic acid is combined with Benfluorex. Albiglutide The risk or severity of hypoglycemia can be increased when Benfluorex is combined with Albiglutide. Alclometasone The risk or severity of hyperglycemia can be increased when Alclometasone is combined with Benfluorex. Alogliptin The risk or severity of hypoglycemia can be increased when Alogliptin is combined with Benfluorex. Amcinonide The risk or severity of hyperglycemia can be increased when Amcinonide is combined with Benfluorex. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Benfluorex hydrochloride X7O165XZ00 23642-66-2 NLOALSPYZIIXEO-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
- 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]
- 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]
- Weissman NJ: Appetite suppressants and valvular heart disease. Am J Med Sci. 2001 Apr;321(4):285-91. [Article]
- External Links
- KEGG Drug
- D07192
- PubChem Compound
- 2318
- PubChem Substance
- 310264978
- ChemSpider
- 2228
- 18880
- ChEBI
- 93826
- ChEMBL
- CHEMBL400599
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Benfluorex
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 2 Unknown Status Treatment Type 2 Diabetes Mellitus 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet, coated Pill - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00128 mg/mL ALOGPS logP 4.26 ALOGPS logP 4.92 Chemaxon logS -5.4 ALOGPS pKa (Strongest Basic) 9.14 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 38.33 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 90.57 m3·mol-1 Chemaxon Polarizability 34.83 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available MS/MS Spectrum - , positive LC-MS/MS splash10-0a4i-2910000000-9d514cebe36c513591b0
Drug created at June 25, 2014 16:57 / Updated at March 03, 2023 17:48