Dexfenfluramine

Dexfenfluramine

Clinical data
MedlinePlus	a682088
ATC code	A08AA04 (WHO)
Legal status
Legal status	US: Unscheduled Withdrawn from market
Pharmacokinetic data
Protein binding	36%
Elimination half-life	17–20 hours
Identifiers
IUPAC name (S)-N-Ethyl-1-[3-(trifluoromethyl)phenyl]-propan-2-amine
CAS Number	3239-44-9 Y
PubChem CID	66265
DrugBank	DB01191 Y
ChemSpider	59646 Y
UNII	E35R3G56OV
KEGG	D07805 Y
ChEBI	CHEBI:439329 Y
ChEMBL	ChEMBL248702 Y
Chemical and physical data
Formula	C12H16F3N
Molar mass	231.262 g·mol−1
3D model (JSmol)	Interactive image
SMILES FC(F)(F)c1cccc(c1)C[C@@H](NCC)C
InChI 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 Y Key:DBGIVFWFUFKIQN-VIFPVBQESA-N Y
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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. 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, the FDA withdrew the approval 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 It was later superseded by sibutramine, which, although initially considered a safer alternative to both dexfenfluramine and fenfluramine, was likewise removed from the US market in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.

The drug was developed by Interneuron Pharmaceuticals, a company co-founded by Richard Wurtman, aimed at marketing discoveries by Massachusetts Institute of Technology scientists. Interneuron licensed the patent to Wyeth-Ayerst Laboratories. 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.

See also

• Benfluorex
• Fenfluramine
• Levofenfluramine
• Norfenfluramine

External links

• Drug description
• Dexfenfluramine hydrochloride
• Questions and Answers about Withdrawal of Fenfluramine (Pondimin) and Dexfenfluramine (Redux)
• Frontline: Dangerous prescriptions—Interview with Leo Lutwak, M.D. in which he discuses the side effects of fenfluramine, its successor Redux, and the Fen-Phen combination