Dexfenfluramine

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Dexfenfluramine
Dexfenfluramine.svg
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
  (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 It was later superseded by sibutramine, which, although initially considered a safer alternative to both dexfenfluramine and fenfluramine[citation needed], was likewise removed from the US market in 2010.[3]

The drug was developed by Interneuron Pharmaceuticals, a company co-founded by Richard Wurtman, aimed at marketing discoveries by Massachusetts Institute of Technology scientists.[4] Interneuron licensed the patent to Wyeth-Ayerst Laboratories.[5] Although at the time of its release, some optimism prevailed that it might herald a new approach[citation needed], 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.[6]

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[edit]

References[edit]

  1. ^ a b Stuart Ira Fox. Human Physiology. Twelfth Edition. McGraw Hill. 2011. p.665.
  2. ^ FDA September 15, 1997. FDA Announces Withdrawal Fenfluramine and Dexfenfluramine (Fen-Phen)
  3. ^ "Abbott Pulls Diet Drug Meridia Off US Shelves". Wall Street Journal. 8 October 2010. Archived from the original on 23 October 2010. 
  4. ^ 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)
  5. ^ 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)
  6. ^ "DEA Accedes to Ecstasy Test". Wired. 2 March 2004. 

External links[edit]