Dexfenfluramine

Dexfenfluramine
Systematic (IUPAC) name
(S)-N-Ethyl-1-[3-(trifluoromethyl)phenyl]-propan-2-amine
Clinical data
MedlinePlus a682088
Legal status
Legal status
Pharmacokinetic data
Protein binding 36%
Biological half-life 17–20 hours
Identifiers
CAS Number 3239-44-9 YesY
ATC code A08AA04 (WHO)
PubChem CID 66265
DrugBank DB01191 YesY
ChemSpider 59646 YesY
UNII E35R3G56OV YesY
KEGG D07805 YesY
ChEBI CHEBI:439329 YesY
ChEMBL CHEMBL248702 YesY
Chemical data
Formula C12H16F3N
Molar mass 231.257 g/mol
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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 However, following multiple concerns about the cardiovascular side-effects of the drug, [1] such approval was withdrawn and it was retired from the market in 1997. 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 It was later superseded by sibutramine, which, although initially considered a safer alternative to both dexfenfluramine and fenfluramine, was likewise removed from the US market in 2010.[2]

The drug was manufactured by Interneuron Pharmaceuticals, a company co-founded by Richard Wurtman, aimed at marketing discoveries by Massachusetts Institute of Technology scientists.[3] In the case of Redux, Interneuron's manufacture was under licence to Wyeth-Ayerst Laboratories.[4] Although at the time of its release, some optimism prevailed that it might herald a new approach, there remained some reservations amongst neurologists, twenty-two of whom petitioned the FDA to delay approval. Their concern was based on the work of George A. Ricaurte, whose techniques and conclusions were later questioned.[5]

In actuality, most conversant with the discussion felt that dexfenfluramine's only advantage was patent protection for its licensed companies. Racemic fenfluramine was far cheaper.

See also

References

  1. 1 2 Stuart Ira Fox. Human Physiology. Twelfth Edition. McGraw Hill. 2011. p.665.
  2. ↑ https://web.archive.org/20101023191137/http://online.wsj.com/article/BT-CO-20101008-710904.html. Archived from the original on 23 October 2010. Missing or empty |title= (help)
  3. ↑ Lemonick, Michael D; Dowell, William; Nash, J. Madeleine; Ramirez, Ainissa; Reid, Brian; Ressner, Jeffrey (23 September 1996), ., ed., "The New Miracle Drug?", Time, retrieved 3 October 2010 |chapter= ignored (help)
  4. ↑ Lemonick, Michael D; Nash, J. Madeleine; Park, Alice; Thompson, Dick (29 September 1997), ., ed., "The Mood Molecule", Time, retrieved 4 October 2010 |chapter= ignored (help)
  5. ↑ "DEA Accedes to Ecstasy Test". Wired. 2 March 2004.

External links


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