Dexfenfluramine
Serotonergic anorectic medication
title: "Dexfenfluramine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["3-(trifluoromethyl)phenyl-compounds", "5-ht2b-agonists", "cardiotoxins", "enantiopure-drugs", "serotonin-receptor-agonists", "serotonin-releasing-agents", "substituted-amphetamines", "withdrawn-anti-obesity-drugs", "withdrawn-drugs"] description: "Serotonergic anorectic medication" topic_path: "general/3-trifluoromethyl-phenyl-compounds" source: "https://en.wikipedia.org/wiki/Dexfenfluramine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0
::summary Serotonergic anorectic medication ::
::data[format=table title="Infobox drug"]
| Field | Value |
|---|---|
| verifiedrevid | 464367204 |
| IUPAC_name | (S)-N-Ethyl-1-[3-(trifluoromethyl)phenyl]-propan-2-amine |
| image | Dexfenfluramine.svg |
| image_class | skin-invert-image |
| image2 | Fenfluramine,dextro 3D BS.png |
| image_class2 | bg-transparent |
| tradename | Redux |
| MedlinePlus | a682088 |
| legal_AU | |
| legal_BR | F4 |
| legal_BR_comment | |
| legal_CA | |
| legal_DE | |
| legal_NZ | |
| legal_UK | |
| legal_US | Unscheduled |
| legal_status | Withdrawn from market |
| protein_bound | 36% |
| metabolites | Dexnorfenfluramine |
| elimination_half-life | 17–20 hours |
| CAS_number_Ref | |
| CAS_number | 3239-44-9 |
| ATC_prefix | A08 |
| ATC_suffix | AA04 |
| PubChem | 66265 |
| DrugBank_Ref | |
| DrugBank | DB01191 |
| ChemSpiderID_Ref | |
| ChemSpiderID | 59646 |
| UNII_Ref | |
| UNII | E35R3G56OV |
| KEGG_Ref | |
| KEGG | D07805 |
| ChEBI_Ref | |
| ChEBI | 439329 |
| ChEMBL_Ref | |
| ChEMBL | 248702 |
| synonyms | Dextrofenfluramine; d-Fenfluramine; (S)-Fenfluramine; S-Fenfluramine; (+)-Fenfluramine; S(+)-Fenfluramine; (S)-(+)-Fenfluramine |
| C | 12 |
| H | 16 |
| F | 3 |
| N | 1 |
| SMILES | FC(F)(F)c1cccc(c1)CC@@HC |
| StdInChI_Ref | |
| StdInChI | 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 |
| StdInChIKey_Ref | |
| StdInChIKey | DBGIVFWFUFKIQN-VIFPVBQESA-N |
| :: |
| verifiedrevid = 464367204 | IUPAC_name = (S)-N-Ethyl-1-[3-(trifluoromethyl)phenyl]-propan-2-amine | image = Dexfenfluramine.svg | image_class = skin-invert-image | width = | image2 = Fenfluramine,dextro 3D BS.png | image_class2 = bg-transparent | width2 =
| tradename = Redux | MedlinePlus = a682088
| legal_AU = | legal_BR = F4 | legal_BR_comment = | legal_CA = | legal_DE = | legal_NZ = | legal_UK = | legal_US = Unscheduled | legal_status = Withdrawn from market
| bioavailability = | protein_bound = 36% | metabolism = | metabolites = Dexnorfenfluramine | elimination_half-life = 17–20 hours | excretion =
| CAS_number_Ref = | CAS_number = 3239-44-9 | ATC_prefix = A08 | ATC_suffix = AA04 | PubChem = 66265 | DrugBank_Ref = | DrugBank = DB01191 | ChemSpiderID_Ref = | ChemSpiderID = 59646 | UNII_Ref = | UNII = E35R3G56OV | KEGG_Ref = | KEGG = D07805 | ChEBI_Ref = | ChEBI = 439329 | ChEMBL_Ref = | ChEMBL = 248702 | synonyms = Dextrofenfluramine; d-Fenfluramine; (S)-Fenfluramine; S-Fenfluramine; (+)-Fenfluramine; S(+)-Fenfluramine; (S)-(+)-Fenfluramine
| C = 12 | H = 16 | F = 3 | N = 1 | SMILES = FC(F)(F)c1cccc(c1)CC@@HC | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = DBGIVFWFUFKIQN-VIFPVBQESA-N
Dexfenfluramine, formerly sold under the brand name Redux, is a serotonergic drug that was used as an appetite suppressant to promote weight loss. 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 (FDA) for the purposes of weight loss. However, following multiple concerns about its cardiovascular side effects, 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. 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.
References
References
- Anvisa. (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial". [[Diário Oficial da União]].
- (2011). "Human Physiology". McGraw Hill.
- FDA 15 September 1997. [https://web.archive.org/web/20090827064123/http://www.fda.gov/Drugs/DrugSafety/PostmarketDrugSafetyInformationforPatientsandProviders/ucm179871.htm FDA Announces Withdrawal Fenfluramine and Dexfenfluramine (Fen-Phen)]
- "Dexfenfluramine". U.S. Library of Medicine.
- (July 1998). "A comparison of sibutramine and dexfenfluramine in the treatment of obesity". Obesity Research.
- (March 1997). "Sibutramine--a review of clinical efficacy". International Journal of Obesity and Related Metabolic Disorders.
- (8 October 2010). "Abbott Pulls Diet Drug Meridia Off US Shelves". The Wall Street Journal.
- (February 2011). "Rise and fall of anti-obesity drugs". World Journal of Diabetes.
- (November 1996). "Dexfenfluramine. An updated review of its therapeutic use in the management of obesity". Drugs.
- (2 March 2004). "DEA Accedes to Ecstasy Test".
- (23 September 1996). "The New Miracle Drug?".
- (29 September 1997). "The Mood Molecule".
::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::