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Legal status	Schedule IV (US) Withdrawn from market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 Y
ATC code	A08AA04
PubChem	CID 66265
DrugBank	DB01191
ChemSpider	59646 Y
UNII	E35R3G56OV Y
KEGG	D07805 Y
ChEBI	CHEBI:439329 Y
ChEMBL	CHEMBL248702 Y
Chemical data
Formula	C12H16F3N
Mol. mass	231.257 g/mol
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
Y (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 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 However, following multiple concerns about the cardiovascular side-effects of the drug, such approval was withdrawn and it was retired from the market in 1997.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 It was later superseded by sibutramine, which although initially considered a safer alternative to both dexfenfluramine and fenfluramine^{[citation needed]}, was also removed from the US market in 2010.

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

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

• Fenfluramine
• Levofenfluramine
• Norfenfluramine
• Benfluorex

External links

• FDA Announces Withdrawal Fenfluramine and Dexfenfluramine (Fen-Phen)
• 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