Details
Stereochemistry | RACEMIC |
Molecular Formula | C19H20F3NO2 |
Molecular Weight | 351.3628 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(CC1=CC(=CC=C1)C(F)(F)F)NCCOC(=O)C2=CC=CC=C2
InChI
InChIKey=CJAVTWRYCDNHSM-UHFFFAOYSA-N
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
Benfluorex under trade name Mediator was launched in 1976 for controlling blood sugar levels in people with type 2 diabetes. In 2009 this drug together with others medicines containing it was withdrawn because of the risk of heart valve disease. The mechanisms by which benfluorex reduces hepatic gluconeogenesis are markedly different from those of metformin, the main antidiabetic compound used in the world. It was suggested that inhibition of gluconeogenesis by benfluorex was, at least in part, due to a decrease in mitochondrial β-oxidation. First, benfluorex decreased acetyl-CoA concentration, which in turn would reduce pyruvate carboxylase activity and release its inhibitory effect on pyruvate dehydrogenase. Second, benfluorex decreased both the ATP-to-ADP and the NAD+-to-NADH ratios, leading to a reduced gluconeogenic flux at the level of 3-phosphoglycerate kinase and GAPDH. Changes in cellular redox state represent probably the main mechanism by which benfluorex reduces glucose production in hepatocytes.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: GO:0071461 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12145146 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Mediator Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Addition of benfluorex to biguanide improves glycemic control in obese non-insulin-dependent diabetes: a double-blind study versus placebo. | 1999 Mar-Apr |
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Effects of benfluorex on fatty acid and glucose metabolism in isolated rat hepatocytes: from metabolic fluxes to gene expression. | 2002 Aug |
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Six-month efficacy of benfluorex vs. placebo or metformin in diet-failed type 2 diabetic patients. | 2003 Mar |
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Hidden amphetamines: from smoking cessation to diabetes. | 2004 Feb |
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Myc-induced proliferation and transformation require Akt-mediated phosphorylation of FoxO proteins. | 2004 Jul 21 |
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Benfluorex as a therapeutic option for insulin resistance in HIV lipodystrophy syndrome. | 2004 Mar-Apr |
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On the mechanism of constitutive Pdr1 activator-mediated PDR5 transcription in Saccharomyces cerevisiae: evidence for enhanced recruitment of coactivators and altered nucleosome structures. | 2004 Oct 8 |
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Modeling neuromuscular modulation in Aplysia. III. Interaction of central motor commands and peripheral modulatory state for optimal behavior. | 2005 Mar |
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ATP-dependent and ATP-independent roles for the Rad54 chromatin remodeling enzyme during recombinational repair of a DNA double strand break. | 2005 Mar 18 |
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Valvular heart disease in a patient taking benfluorex. | 2006 Dec |
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Efficacy of benfluorex in combination with sulfonylurea in type 2 diabetic patients: an 18-week, randomized, double-blind study. | 2006 Mar |
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Benfluorex: negative data in France, but still on the market. Neuropsychiatric disorders, pulmonary hypertension and heart valve damage. | 2009 Jun |
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Fenfluramine-like cardiovascular side-effects of benfluorex. | 2009 Mar |
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French doctors demand to know why drug stayed on the market for so long. | 2010 Dec 3 |
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Benfluorex: yet more valve disorders. | 2010 Jun |
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Valvular heart disease associated with benfluorex. | 2010 May |
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Benfluorex: EU marketing authorisation finally withdrawn. | 2010 Oct |
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT00544518
2 tablets (150-450 mg/day) with breakfast and dinner for the first four weeks, if necessary, increase 2 tablets with noon for the next time, one of 2 tablets is dummy tablet.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7671345
Benfluorex at 30 microM has been shown to inhibit Acyl CoA cholesterol acyl transferase activity in rat liver microsome preparations and to fluidize these membranes, as reflected by a decrease in the lipid order parameter. When drug concentrations were higher (60-200 microM), the compound differed in its enzymatic inhibition properties but retained the same fluidizing effects.
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C29728
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C29703
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A10BX06
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QA10BX06
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m2311
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100000086617
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18880
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CHEMBL400599
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BENFLUOREX
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C001584
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C72936
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SUB05714MIG
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)