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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 However, following multiple concerns about the cardiovascular side-effects of the drug, such approval was withdrawn and it was retired from the market in 1997.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 It was later superseded by sibutramine, which, although initially considered a safer alternative to both dexfenfluramine and fenfluramine^{[citation needed]}, was likewise removed from the US market in 2010.^[1]

The drug was manufactured by Interneuron Pharmaceuticals, a company co-founded by Richard Wurtman, aimed at marketing discoveries by Massachusetts Institute of Technology scientists.^[2] In the case of Redux, Interneuron's manufacture was under licence to Wyeth-Ayerst Laboratories.^[3] 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..^[4]

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.

References[edit source | edit]

^ http://online.wsj.com/article/BT-CO-20101008-710904.html. Missing or empty |title= (help)^{[dead link]}
^ Lemonick, Michael D; Dowell, William; Nash, J. Madeleine; Ramirez, Ainissa; Reid, Brian; Ressner, Jeffrey (23 September 1996), Wurtman as co-founder of Interneuron Pharmaceuticals, in ., "The New Miracle Drug?", Time, retrieved 3 October 2010
^ Lemonick, Michael D; Nash, J. Madeleine; Park, Alice; Thompson, Dick (29 September 1997), Redux patent and controversy, in ., "The Mood Molecule", Time, retrieved 4 October 2010
^ "DEA Accedes to Ecstasy Test". Wired. 2 March 2004.

External links[edit source | edit]

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

This drug article relating to the nervous system is a stub. You can help Wikipedia by expanding it.

UpToDate Contents

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1. 薬剤誘発性の弁膜症 valvular heart disease induced by drugs
2. 成人における肺高血圧症の概要 overview of pulmonary hypertension in adults
3. 肺高血圧症の病因 pathogenesis of pulmonary hypertension
4. 成人における肥満：薬物療法 obesity in adults drug therapy
5. 成人における気晴らし食い-摂食障害：治療の概要 binge eating disorder in adults overview of treatment

English Journal

Dexfenfluramine and the oestrogen-metabolizing enzyme CYP1B1 in the development of pulmonary arterial hypertension.

Dempsie Y, Macritchie NA, White K, Morecroft I, Wright AF, Nilsen M, Loughlin L, Mair KM, Maclean MR.SourceInstitute of Cardiovascular and Medical Sciences, College of Medical, Veterinary and Life Sciences, Glasgow University, West Medical Building, Glasgow G12 8QQ, UK.
Cardiovascular research.Cardiovasc Res.2013 Apr 23. [Epub ahead of print]
AIMS: Pulmonary arterial hypertension (PAH) occurs more frequently in women than men. Oestrogen and the oestrogen-metabolising enzyme cytochrome P450 1B1 (CYP1B1) play a role in the development of PAH. Anorectic drugs such as dexfenfluramine (Dfen) have been associated with the development of PAH. D
PMID 23519266

Pulmonary hypertension associated with benfluorex exposure.

Savale L, Chaumais MC, Cottin V, Bergot E, Frachon I, Prevot G, Pison C, Dromer C, Poubeau P, Lamblin N, Habib G, Reynaud-Gaubert M, Bourdin A, Sanchez O, Tubert-Bitter P, Jaïs X, Montani D, Sitbon O, Simonneau G, Humbert M.SourceUniv Paris-Sud, Faculte de Medecine and AP-HP Centre de Reference del’Hypertension Pulmonaire Severe, Service de Pneumologie et SoinsIntensifs, Hopital Bicetre, Le Kremlin Bicetre, France
The European respiratory journal : official journal of the European Society for Clinical Respiratory Physiology.Eur Respir J.2012 Nov;40(5):1164-72. doi: 10.1183/09031936.00188611. Epub 2012 Apr 20.
Benfluorex was marketed in France until 2009, despite its similar pharmacological properties with fenfluramine and its derivatives known to be a cause of pulmonary arterial hypertension (PAH). The aim of this study is to report clinical and haemodynamic characteristics for patients suffering from pu
PMID 22523367

CB1 receptor antagonists: new discoveries leading to new perspectives.

Kirilly E, Gonda X, Bagdy G.SourceDepartment of Pharmacodynamics, Semmelweis University, Budapest, Hungary.
Acta physiologica (Oxford, England).Acta Physiol (Oxf).2012 May;205(1):41-60. doi: 10.1111/j.1748-1716.2012.02402.x.
CB(1) receptor antagonists were among the most promising drug targets in the last decade. They have been explored and found to be effective as therapeutic agents for obesity and related cardiometabolic problems; however, use of rimonabant, the first marketed CB(1) receptor antagonist, has been sus
PMID 22463610

Japanese Journal

Fenfluramine/Dexfenfluramine と心臓弁膜症について

渡邉ひかる,久保田潔
臨床薬理 = Japanese journal of clinical pharmacology 40(1), 41-46, 2009-01-31
NAID 10026157474

中国製ダイエット用健康食品中のN-nitrosofenfluramineの光学純度の決定

中台亜里,稲垣弘文,南正康,高橋秀依,南目梨江,大沢基保,池上四郎
藥學雜誌 123(9), 805-809, 2003-09-01
2001年から2002年夏にかけて,中国製ダイエット用健康食品による健康被害が相ついで報告され,社会問題にまでなったのは記憶に新しい.その主な被害は,劇症肝炎や急性肝炎など,重篤な肝障害であり,死者が出るまでに至った.既に厚生労働省は,問題のダイエット食品中から,3-5%の濃度でN-nitrosofenfluramineが検出されたことを報告している.さらに,その後行われた国立医薬品食品衛生研究所 …
NAID 110003614927

Related Pictures

★リンクテーブル★

リンク元	「デクスフェンフルラミン」

「デクスフェンフルラミン」

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
ATC code	A08AA04
PubChem	CID 66265
DrugBank	DB01191
ChemSpider	59646
UNII	E35R3G56OV
KEGG	D07805
ChEBI	CHEBI:439329
ChEMBL	CHEMBL248702
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 ; Key:DBGIVFWFUFKIQN-VIFPVBQESA-N ;
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　　[★]

英: dexfenfluramine

-dexfenfluramine

[1] ttp://online.wsj.com/article/BT-CO-20101008-710904.html. Missing or empty |title= (help)^{[dead link]}

[LemonickEtal1996p4-2] Lemonick, Michael D; Dowell, William; Nash, J. Madeleine; Ramirez, Ainissa; Reid, Brian; Ressner, Jeffrey (23 September 1996), Wurtman as co-founder of Interneuron Pharmaceuticals, in ., "The New Miracle Drug?", Time, retrieved 3 October 2010

[LemonickeEtal1997p6-3] Lemonick, Michael D; Nash, J. Madeleine; Park, Alice; Thompson, Dick (29 September 1997), Redux patent and controversy, in ., "The Mood Molecule", Time, retrieved 4 October 2010

[titleDEA_Accedes_to_Ecstasy_Test-4] "DEA Accedes to Ecstasy Test". Wired. 2 March 2004.

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dexfenfluramine