Chemistry:Dexfenfluramine

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Short description: Serotonergic anorectic medication
Dexfenfluramine
Dexfenfluramine.svg
Fenfluramine,dextro 3D BS.png
Clinical data
MedlinePlusa682088
ATC code
Legal status
Legal status
  • BR: F4
  • US: Unscheduled
  • Withdrawn from market
Pharmacokinetic data
Protein binding36%
Elimination half-life17–20 hours
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC12H16F3N
Molar mass231.262 g·mol−1
3D model (JSmol)
  (verify)

Dexfenfluramine, marketed as dexfenfluramine hydrochloride under the name Redux, is a serotonergic anorectic drug: it reduces appetite by increasing the amount of extracellular serotonin in the brain.[1] It is the d-enantiomer of fenfluramine and is structurally similar to amphetamine, but lacks any psychologically stimulating effects.

Dexfenfluramine was, for some years in the mid-1990s, approved by the United States Food and Drug Administration for the purposes of weight loss. However, following multiple concerns about the cardiovascular side-effects of the drug,[1] the FDA withdrew the approval in 1997.[2] After it was removed in the US, dexfenfluramine was also pulled out in other global markets. It was later superseded by sibutramine, which, although initially considered a safer alternative to both dexfenfluramine and fenfluramine,[3][4][5] was likewise removed from the US market in 2010.[6][7]

The drug was developed by Interneuron Pharmaceuticals, a company co-founded by Richard Wurtman, aimed at marketing discoveries by Massachusetts Institute of Technology scientists.[8] Interneuron licensed the patent to Wyeth-Ayerst Laboratories.[9] Although at the time of its release, some optimism prevailed that it might herald a new approach,[10] there remained some reservations amongst neurologists, twenty-two of whom petitioned the FDA to delay approval.[citation needed] Their concern was based on the work of George A. Ricaurte, whose techniques and conclusions were later questioned.[11]

See also

References

  1. ↑ 1.0 1.1 Human Physiology (Twelfth ed.). McGraw Hill. 2011. p. 665. 
  2. ↑ FDA 15 September 1997. FDA Announces Withdrawal Fenfluramine and Dexfenfluramine (Fen-Phen)
  3. ↑ "Dexfenfluramine" (in en). PubChem. U.S. Library of Medicine. https://pubchem.ncbi.nlm.nih.gov/compound/66265. 
  4. ↑ "A comparison of sibutramine and dexfenfluramine in the treatment of obesity". Obesity Research 6 (4): 285–291. July 1998. doi:10.1002/j.1550-8528.1998.tb00351.x. PMID 9688105. 
  5. ↑ "Sibutramine--a review of clinical efficacy". International Journal of Obesity and Related Metabolic Disorders 21 (Suppl 1): S30–6; discussion 37–9. March 1997. PMID 9130039. https://europepmc.org/article/med/9130039. 
  6. ↑ "Abbott Pulls Diet Drug Meridia Off US Shelves". The Wall Street Journal. 8 October 2010. https://www.wsj.com/article/BT-CO-20101008-710904.html. 
  7. ↑ "Rise and fall of anti-obesity drugs". World Journal of Diabetes 2 (2): 19–23. February 2011. doi:10.4239/wjd.v2.i2.19. PMID 21537456. 
  8. ↑ "The New Miracle Drug?". Time. 23 September 1996. http://www.time.com/time/magazine/article/0,9171,985187,00.html. Retrieved 3 October 2010. 
  9. ↑ "The Mood Molecule". Time. 29 September 1997. http://www.time.com/time/magazine/article/0,9171,987066,00.html. Retrieved 4 October 2010. 
  10. ↑ "Dexfenfluramine. An updated review of its therapeutic use in the management of obesity". Drugs 52 (5): 696–724. November 1996. doi:10.2165/00003495-199652050-00007. PMID 9118819. 
  11. ↑ "DEA Accedes to Ecstasy Test". Wired. 2 March 2004. https://www.wired.com/news/business/0,1367,62506,00.html. 

External links



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