Dexfenfluramine

Dexfenfluramine
Clinical data
MedlinePlus	a682088
ATC code	A08AA04 (WHO) ;
Legal status
Legal status	US: Schedule IV ; Withdrawn from market;
Pharmacokinetic data
Protein binding	36%
Elimination half-life	17–20 hours
Identifiers
	show IUPAC name
CAS Number	3239-44-9 ;
PubChem CID	66265;
DrugBank	DB01191 ;
ChemSpider	59646 ;
UNII	E35R3G56OV;
KEGG	D07805 ;
ChEBI	CHEBI:439329 ;
ChEMBL	ChEMBL248702 ;
Chemical and physical data
Formula	C12H16F3N
Molar mass	231.262 g·mol−1
3D model (JSmol)	Interactive image;
	show SMILES
	show InChI

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.^[1] 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,^[1] the FDA withdrew the approval in 1997.^[2] 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 It was later superseded by sibutramine, which, although initially considered a safer alternative to both dexfenfluramine and fenfluramine^{[citation needed]}, was likewise removed from the US market in 2010.^[3]

The drug was developed by , a company co-founded by Richard Wurtman, aimed at marketing discoveries by Massachusetts Institute of Technology scientists.^[4] Interneuron licensed the patent to Wyeth-Ayerst Laboratories.^[5] 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.^[6]

References[]

^ Jump up to: ^a ^b Fox SI (2011). Human Physiology (Twelfth ed.). McGraw Hill. p. 665.
^ FDA September 15, 1997. FDA Announces Withdrawal Fenfluramine and Dexfenfluramine (Fen-Phen)
^ "Abbott Pulls Diet Drug Meridia Off US Shelves". Wall Street Journal. 8 October 2010. Archived from the original on 23 October 2010.
^ 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.
^ 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.
^ "DEA Accedes to Ecstasy Test". Wired. 2 March 2004.

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

[stuart-1] Jump up to: ^a ^b Fox SI (2011). Human Physiology (Twelfth ed.). McGraw Hill. p. 665.

[2] FDA September 15, 1997. FDA Announces Withdrawal Fenfluramine and Dexfenfluramine (Fen-Phen)

[3] "Abbott Pulls Diet Drug Meridia Off US Shelves". Wall Street Journal. 8 October 2010. Archived from the original on 23 October 2010.

[LemonickEtal1996p4-4] 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.

[LemonickeEtal1997p6-5] 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.

[titleDEA_Accedes_to_Ecstasy_Test-6] "DEA Accedes to Ecstasy Test". Wired. 2 March 2004.

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Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-C 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-O 2C-O-4 2C-P 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-7 2C-T-8 2C-T-9 2C-T-13 2C-T-15 2C-T-16 2C-T-17 2C-T-19 2C-T-21 2C-T-28 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-AL 3C-BZ 3C-E 3C-MAL 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA ZDCM-04 Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L-Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA Selegiline (also D-Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D-DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L-DOPA (Levodopa) L-DOPS (Droxidopa) L-Phenylalanine L-Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101 Venlafaxine

Dexfenfluramine

See also[]

References[]

External links[]