Dexfenfluramine

Dexfenfluramine
Dexfenfluramine
Systematic (IUPAC) name
(S)-N-Ethyl-1-[3-(trifluoromethyl)phenyl]-propan-2-amine
Clinical data
MedlinePlus a682088
Pregnancy cat.  ?
Legal status Schedule IV (US) Withdrawn from market
Pharmacokinetic data
Protein binding 36%
Half-life 17-20 hours
Identifiers
CAS number 3239-44-9 YesY
ATC code A08AA04
PubChem CID 66265
DrugBank APRD00648
ChemSpider 59646 YesY
UNII E35R3G56OV YesY
KEGG D07805 YesY
ChEBI CHEBI:439329 YesY
ChEMBL CHEMBL248702 YesY
Chemical data
Formula C12H16F3N 
Mol. mass 231.257 g/mol
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

Dexfenfluramine, marketed as dexfenfluramine hydrochloride under the name Redux, is a serotoninergic anorectic drug: it reduces appetite by increasing the amount of extracellular serotonin in the brain. It is the d-enantiomer of fenfluramine and is structually 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 However, following multiple concerns about the cardiovascular side-effects of the drug, such approval was withdrawn and it was retired from the market in 1997.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 It was later superseded by sibutramine, which although initially considered a safer alternative to both dexfenfluramine and fenfluramine[citation needed], was removed from the US market as well in 2010[1].

The drug was manufactured by Interneuron Pharmaceuticals, a company co-founded by Richard Wurtman, aimed at marketing discoveries by Massachusetts Institute of Technology scientists.[2] In the case of Redux, Interneuron's manufacture was under licence to Wyeth-Ayerst Laboratories.[3] 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.[citation needed]

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

See also

References

  1. ^ . http://online.wsj.com/article/BT-CO-20101008-710904.html. [dead link]
  2. ^ Lemonick, Michael D; Dowell, William; Nash, J. Madeleine; Ramirez, Ainissa; Reid, Brian; Ressner, Jeffrey (Sep 23, 1996), Wurtman as co-founder of Interneuron Pharmaceuticals, in ., "The New Miracle Drug?", Time, http://www.time.com/time/magazine/article/0,9171,985187-4,00.html, retrieved 03 October 2010 
  3. ^ Lemonick, Michael D; Nash, J. Madeleine; Park, Alice; Thompson, Dick (Sep 29, 1997), Redux patent and controversy, in ., "The Mood Molecule", Time, http://www.time.com/time/magazine/article/0,9171,987066-6,00.html, retrieved 04 October 2010 

External links


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