Dexfenfluramine

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.[2] It is the d-enantiomer of fenfluramine and is structurally similar to amphetamine, but lacks any psychologically stimulating effects.

Dexfenfluramine
Clinical data
MedlinePlusa682088
ATC code
Legal status
Legal status
  • BR: Class F4 (Other prohibited substances)[1]
  • US: Unscheduled
  • Withdrawn from market
Pharmacokinetic data
Protein binding36%
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
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 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,[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 It was later superseded by sibutramine, which, although initially considered a safer alternative to both dexfenfluramine and fenfluramine,[4][5][6] was likewise removed from the US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. Their concern was based on the work of George A. Ricaurte, whose techniques and conclusions were later questioned.[12]

See also

References
  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. Retrieved 27 August 2023.
  2. Fox 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. Retrieved 29 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 from the 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 from the original on 6 November 2010. Retrieved 3 October 2010.
  10. Lemonick MD, Nash JM, Park A, Thompson D (29 September 1997). "The Mood Molecule". Time. Archived from the original on 3 October 2008. Retrieved 4 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 from the original on 10 January 2006.
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