Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C19H20F3NO2.ClH |
| Molecular Weight | 387.824 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CC(CC1=CC(=CC=C1)C(F)(F)F)NCCOC(=O)C2=CC=CC=C2
InChI
InChIKey=NLOALSPYZIIXEO-UHFFFAOYSA-N
InChI=1S/C19H20F3NO2.ClH/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;1H
| Molecular Formula | C19H20F3NO2 |
| Molecular Weight | 351.3628 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 In 2009 this drug together with others medicines containing it was withdrawn because of the risk of heart valve disease.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
PubMed
| Title | Date | PubMed |
|---|---|---|
| French doctors demand to know why drug stayed on the market for so long. | 2010-12-03 |
|
| Benfluorex and valvular heart disease: a cohort study of a million people with diabetes mellitus. | 2010-12 |
|
| Benfluorex: EU marketing authorisation finally withdrawn. | 2010-10 |
|
| Thermal and X-ray powder diffraction structural characterization of two benfluorex hydrochloride polymorphs. | 2010-09-21 |
|
| MR molecular imaging of aortic angiogenesis. | 2010-08 |
|
| Restrictive organic mitral regurgitation associated with benfluorex therapy. | 2010-08 |
|
| Benfluorex: yet more valve disorders. | 2010-06 |
|
| Valvular heart disease associated with benfluorex. | 2010-05 |
|
| Benfluorex and unexplained valvular heart disease: a case-control study. | 2010-04-12 |
|
| Benfluorex: increasing reports of valve disorders. | 2010-02 |
|
| Benfluorex: negative data in France, but still on the market. Neuropsychiatric disorders, pulmonary hypertension and heart valve damage. | 2009-06 |
|
| A randomized, double-blind, placebo-controlled study of benfluorex in HIV-infected patients with insulin resistance or impaired glucose tolerance. | 2009-04-14 |
|
| Effects of benfluorex-vitamin C supplementation on cutaneous capillaries of diabetic rats. | 2009-03 |
|
| Fenfluramine-like cardiovascular side-effects of benfluorex. | 2009-03 |
|
| Efficacy of benfluorex in combination with sulfonylurea in type 2 diabetic patients: an 18 to 34-week, open-label, extension period. | 2009-02 |
|
| Valvular heart disease in a patient taking benfluorex. | 2006-12 |
|
| Efficacy of benfluorex in combination with sulfonylurea in type 2 diabetic patients: an 18-week, randomized, double-blind study. | 2006-03 |
|
| [A case of Parkinsonian syndrome, cognitive impairment and hyperammonemia induced by divalproate sodium prescribed for bipolar disorder]. | 2005-06-24 |
|
| ATP-dependent and ATP-independent roles for the Rad54 chromatin remodeling enzyme during recombinational repair of a DNA double strand break. | 2005-03-18 |
|
| Mediator requirement for both recruitment and postrecruitment steps in transcription initiation. | 2005-03-04 |
|
| Modeling neuromuscular modulation in Aplysia. III. Interaction of central motor commands and peripheral modulatory state for optimal behavior. | 2005-03 |
|
| On the mechanism of constitutive Pdr1 activator-mediated PDR5 transcription in Saccharomyces cerevisiae: evidence for enhanced recruitment of coactivators and altered nucleosome structures. | 2004-10-08 |
|
| Myc-induced proliferation and transformation require Akt-mediated phosphorylation of FoxO proteins. | 2004-07-21 |
|
| Benfluorex as a therapeutic option for insulin resistance in HIV lipodystrophy syndrome. | 2004-04-30 |
|
| Hidden amphetamines: from smoking cessation to diabetes. | 2004-02 |
|
| A study on the release mechanism of drugs from hydrophilic partially coated perforated matrices. | 2003-09 |
|
| Six-month efficacy of benfluorex vs. placebo or metformin in diet-failed type 2 diabetic patients. | 2003-03 |
|
| [Valvular heart disease associated with benfluorex]. | 2003-02 |
|
| Effects of benfluorex on fatty acid and glucose metabolism in isolated rat hepatocytes: from metabolic fluxes to gene expression. | 2002-08 |
|
| Appetite suppressants and valvular heart disease. | 2001-04 |
|
| Addition of benfluorex to biguanide improves glycemic control in obese non-insulin-dependent diabetes: a double-blind study versus placebo. | 1999-08-04 |
Sample Use Guides
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
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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:48:24 GMT 2025
by
admin
on
Mon Mar 31 17:48:24 GMT 2025
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| Record UNII |
X7O165XZ00
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| Record Status |
Validated (UNII)
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| Record Version |
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE | |||
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |