Dexfenfluramine

Serotonergic anorectic medication From Wikipedia, the free encyclopedia

Dexfenfluramine, formerly sold under the brand name Redux, is a serotonergic drug that was used as an appetite suppressant to promote weight loss.[2] It is the d-enantiomer of fenfluramine and is structurally similar to amphetamine, but lacks any psychologically stimulating effects.

Other namesDextrofenfluramine; d-Fenfluramine; (S)-Fenfluramine; S-Fenfluramine; (+)-Fenfluramine; S(+)-Fenfluramine; (S)-(+)-Fenfluramine
ATC code
Quick facts Clinical data, Trade names ...
Dexfenfluramine
Clinical data
Trade namesRedux
Other namesDextrofenfluramine; d-Fenfluramine; (S)-Fenfluramine; S-Fenfluramine; (+)-Fenfluramine; S(+)-Fenfluramine; (S)-(+)-Fenfluramine
MedlinePlusa682088
ATC code
Legal status
Legal status
  • BR: Class F4 (Other prohibited substances)[1]
  • US: Unscheduled
  • Withdrawn from market
Pharmacokinetic data
Protein binding36%
MetabolitesDexnorfenfluramine
Elimination half-life17–20 hours
Identifiers
  • (S)-N-Ethyl-1-[3-(trifluoromethyl)phenyl]-propan-2-amine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H16F3N
Molar mass231.262 g·mol−1
3D model (JSmol)
  • FC(F)(F)c1cccc(c1)C[C@@H](NCC)C
  • InChI=1S/C12H16F3N/c1-3-16-9(2)7-10-5-4-6-11(8-10)12(13,14)15/h4-6,8-9,16H,3,7H2,1-2H3/t9-/m0/s1 checkY
  • Key:DBGIVFWFUFKIQN-VIFPVBQESA-N checkY
  (verify)
Close

Dexfenfluramine was, for some years in the mid-1990s, approved by the United States Food and Drug Administration (FDA) for the purposes of weight loss. However, following multiple concerns about its cardiovascular side effects,[2] the FDA withdrew the approval in 1997.[3] 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 It was later superseded by sibutramine, which, although initially considered a safer alternative to both dexfenfluramine and fenfluramine,[4][5][6] was likewise removed from the US market in 2010.[7][8]

The drug was developed by Interneuron Pharmaceuticals, a company co-founded by Richard Wurtman, aimed at marketing discoveries by Massachusetts Institute of Technology scientists.[9] Interneuron licensed the patent to Wyeth-Ayerst Laboratories.[10] Although at the time of its release, some optimism prevailed that it might herald a new approach,[11] 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.[12]

See also

References

Related Articles

Wikiwand AI