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 | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 | ( + / - ) |
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 In 2009 this drug together with others medicines containing it was withdrawn because of the risk of heart valve disease.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 |
---|---|---|---|
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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Appetite suppressants and valvular heart disease. | 2001 Apr |
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[Valvular heart disease associated with benfluorex]. | 2003 Feb |
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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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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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[A case of Parkinsonian syndrome, cognitive impairment and hyperammonemia induced by divalproate sodium prescribed for bipolar disorder]. | 2005 Jan-Feb |
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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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Efficacy of benfluorex in combination with sulfonylurea in type 2 diabetic patients: an 18 to 34-week, open-label, extension period. | 2009 Feb |
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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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Effects of benfluorex-vitamin C supplementation on cutaneous capillaries of diabetic rats. | 2009 Mar |
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Fenfluramine-like cardiovascular side-effects of benfluorex. | 2009 Mar |
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Benfluorex and unexplained valvular heart disease: a case-control study. | 2010 Apr 12 |
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MR molecular imaging of aortic angiogenesis. | 2010 Aug |
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Restrictive organic mitral regurgitation associated with benfluorex therapy. | 2010 Aug |
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Benfluorex and valvular heart disease: a cohort study of a million people with diabetes mellitus. | 2010 Dec |
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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: increasing reports of valve disorders. | 2010 Feb |
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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 |
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Thermal and X-ray powder diffraction structural characterization of two benfluorex hydrochloride polymorphs. | 2010 Sep 21 |
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:09:25 GMT 2023
by
admin
on
Fri Dec 15 15:09:25 GMT 2023
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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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Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE | |||
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PARENT -> SALT/SOLVATE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |