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Dexfenfluramine

From Wikipedia, the free encyclopedia
Serotonergic anorectic medication

Pharmaceutical compound
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
Pharmacokinetic data
Protein binding36%
MetabolitesDexnorfenfluramine
Eliminationhalf-life17–20 hours
Identifiers
  • (S)-N-Ethyl-1-[3-(trifluoromethyl)phenyl]-propan-2-amine
CAS Number
PubChemCID
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)

Dexfenfluramine, formerly sold under the brand nameRedux, is aserotonergic drug that was used as anappetite suppressant to promoteweight loss.[2] It is the d-enantiomer offenfluramine and is structurally similar toamphetamine, but lacks any psychologically stimulating effects.

Dexfenfluramine was, for some years in the mid-1990s, approved by the United StatesFood and Drug Administration (FDA) for the purposes ofweight 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 It was later superseded bysibutramine, which, although initially considered a safer alternative to both dexfenfluramine andfenfluramine,[4][5][6] was likewise removed from the US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 byRichard Wurtman, aimed at marketing discoveries byMassachusetts Institute of Technology scientists.[9] Interneuron licensed the patent toWyeth-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 ofGeorge A. Ricaurte, whose techniques and conclusions were later questioned.[12]

See also

[edit]

References

[edit]
  1. ^Anvisa (24 July 2023)."RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).Diário Oficial da União (published 25 July 2023).Archived from the original on 27 August 2023. Retrieved27 August 2023.
  2. ^abFox SI (2011).Human Physiology (Twelfth ed.). McGraw Hill. p. 665.
  3. ^FDA 15 September 1997.FDA Announces Withdrawal Fenfluramine and Dexfenfluramine (Fen-Phen)
  4. ^"Dexfenfluramine".PubChem. U.S. Library of Medicine. Retrieved29 March 2023.
  5. ^Hanotin C, Thomas F, Jones SP, Leutenegger E, Drouin P (July 1998)."A comparison of sibutramine and dexfenfluramine in the treatment of obesity".Obesity Research.6 (4):285–291.doi:10.1002/j.1550-8528.1998.tb00351.x.PMID 9688105.
  6. ^Lean ME (March 1997)."Sibutramine--a review of clinical efficacy".International Journal of Obesity and Related Metabolic Disorders.21 (Suppl 1): S30–6, discussion 37–9.PMID 9130039.
  7. ^"Abbott Pulls Diet Drug Meridia Off US Shelves".The Wall Street Journal. 8 October 2010. Archived fromthe original on 23 October 2010.
  8. ^Li MF, Cheung BM (February 2011)."Rise and fall of anti-obesity drugs".World Journal of Diabetes.2 (2):19–23.doi:10.4239/wjd.v2.i2.19.PMC 3083904.PMID 21537456.
  9. ^Lemonick MD, Dowell W, Nash JM, Ramirez A, Reid B, Ressner J (23 September 1996)."The New Miracle Drug?".Time. Archived fromthe original on 6 November 2010. Retrieved3 October 2010.
  10. ^Lemonick MD, Nash JM, Park A, Thompson D (29 September 1997)."The Mood Molecule".Time. Archived fromthe original on 3 October 2008. Retrieved4 October 2010.
  11. ^Davis R, Faulds D (November 1996). "Dexfenfluramine. An updated review of its therapeutic use in the management of obesity".Drugs.52 (5):696–724.doi:10.2165/00003495-199652050-00007.PMID 9118819.S2CID 261029109.
  12. ^Philipkoski K (2 March 2004)."DEA Accedes to Ecstasy Test".Wired. Archived fromthe original on 10 January 2006.

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