Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C12H16F3N.ClH |
Molecular Weight | 267.718 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CCN[C@@H](C)CC1=CC=CC(=C1)C(F)(F)F
InChI
InChIKey=ZXKXJHAOUFHNAS-FVGYRXGTSA-N
InChI=1S/C12H16F3N.ClH/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;1H/t9-;/m0./s1
Dexfenfluramine, also marketed under the name Redux, is a serotoninergic anorectic drug. Dexfenfluramine, the dextrorotatory isomer of fenfluramine, is indicated for use in the management of obesity in patients with a body mass index of > or = 30 kg/m2, or > or = 27 kg/m2 in the presence of other risk factors. Unlike fenfluramine, dexfenfluramine is a pure serotonin agonist. Dexfenfluramine increases serotonergic activity by stimulating serotonin (5-hydroxytryptamine; 5-HT) release into brain synapses, inhibiting its reuptake into presynaptic neurons and by directly stimulating postsynaptic serotonin receptors. Dexfenfluramine reduces blood pressure, percent glycosylated hemoglobin, and concentrations of blood glucose and blood lipids, but these benefits may be indirect. Dexfenfluramine may also be of some value in controlling eating habits in diabetic patients, preventing weight gain after smoking cessation, and treating bulimia, seasonal affective disorder, neuroleptic-induced obesity, and premenstrual syndrome. Dexfenfluramine's most frequent adverse effects are insomnia, diarrhea, and headache; it has also been associated with primary pulmonary hypertension. The drug should not be combined with other serotonergic agonists because of the risk of serotonin syndrome. The recommended dosage is 15 mg twice daily. Dexfenfluramine is effective in the treatment of obesity in selected patients. Because its efficacy is lost after six months of continuous treatment, it should be viewed primarily as an adjunct to diet and exercise. Dexfenfluramine was approved by the FDA in 1996 and has been widely used for the treatment of obesity. However, Dexfenfluramine was removed from the U.S. market in 1997 following reports of valvular heart disease and pulmonary hypertension.
Originator
Approval Year
PubMed
Title | Date | PubMed |
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Treatment of obesity with fenfluramine. | 1975 Jan 31 |
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Appetite-suppressing drugs and valvular heart disease. | 1999 Nov-Dec |
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[Valvular regurgitation caused by anorectic agents]. | 2000 Dec |
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Understanding the neurobiology of suicidal behavior. | 2001 |
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High-speed liquid chromatography/tandem mass spectrometry using a monolithic column for high-throughput bioanalysis. | 2001 |
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Neurotransmitter and hormonal background of hostility in anorexia nervosa. | 2001 |
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Effects of repeated systemic administration of d-Fenfluramine on serotonin and glutamate release in rat ventral hippocampus: comparison with methamphetamine using in vivo microdialysis. | 2001 Apr |
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The quest for biological correlates of social phobia: an interim assessment. | 2001 Apr |
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Comparison of [(18)F]altanserin and [(18)F]deuteroaltanserin for PET imaging of serotonin(2A) receptors in baboon brain: pharmacological studies. | 2001 Apr |
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Anorectic drugs and pulmonary hypertension from the bedside to the bench. | 2001 Apr |
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Appetite suppressants and valvular heart disease. | 2001 Apr |
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Relationship between 5-HT function and impulsivity and aggression in male offenders with personality disorders. | 2001 Apr |
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Association between selective serotonin-reuptake inhibitor therapy and heart valve regurgitation. | 2001 Apr 15 |
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Neuroendocrine serotonergic and dopaminergic responsivity in male schizophrenic patients during treatment with neuroleptics and after switch to risperidone. | 2001 Aug |
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Effects of dietary sucrose on hippocampal serotonin release: a microdialysis study in the freely-moving rat. | 2001 Aug |
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Evidence that hypophagia induced by d-fenfluramine and d-norfenfluramine in the rat is mediated by 5-HT2C receptors. | 2001 Aug |
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Fenfluramine-induced pulmonary vasoconstriction: role of serotonin receptors and potassium channels. | 2001 Aug |
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Relationship between central serotonergic neurotransmission and reduction in alcohol intake by citalopram. | 2001 Aug 1 |
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Aortic and mitral fenfluramine-phentermine valvulopathy in 64 patients treated with anorectic agents. | 2001 Dec |
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Cholesterol and serotonin indices in depressed and suicidal patients. | 2001 Feb |
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PET neuroimaging of clomipramine challenge in humans: focus on the thalamus. | 2001 Feb 16 |
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Elevations in plasmatic titers of corticosterone and aldosterone, in the absence of changes in ACTH, testosterone, or glial fibrillary acidic protein, 72 h following D,L-fenfluramine or D-fenfluramine administration to rats. | 2001 Jan-Feb |
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Low risk of significant echocardiographic valvulopathy in patients treated with anorectic drugs. | 2001 Jul |
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Prolactin response to d-fenfluramine in postmenopausal women on and off ERT: comparison with young women. | 2001 Jul |
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Pharmacologic options for the treatment of obesity. | 2001 Jul 15 |
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"Diet pills" and major depression in the Canadian population. | 2001 Jun |
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3,4-Methylenedioxymethamphetamine (MDMA) as a unique model of serotonin receptor function and serotonin-dopamine interactions. | 2001 Jun |
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Bitter pills, bad medicine. | 2001 Jun 4 |
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In vitro reaction of formaldehyde with fenfluramine: conversion to N-methyl fenfluramine. | 2001 Mar |
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By the way, doctor...I used a diet pill--fenfluramine--a few years ago, but stopped as soon as I heard about it causing heart-valve problems. My doctor has been doing echocardiograms on me every six months. So far, everything looks good. How long do you think I need to keep on getting these checkups? | 2001 May |
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Rapid clot formation and abnormal fibrin structure in a symptomatic patient taking fenfluramine--a case report. | 2001 May |
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1-(m-chlorophenyl)piperazine (mCPP) dissociates in vivo serotonin release from long-term serotonin depletion in rat brain. | 2001 May |
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Serotonin transporter promoter polymorphism is associated with attenuated prolactin response to fenfluramine. | 2001 May 8 |
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Too late, again? | 2001 May-Jun |
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Effects of endogenous neurotransmitters on the in vivo binding of dopamine and 5-HT radiotracers in mice. | 2001 Nov |
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LY393558, a 5-hydroxytryptamine reuptake inhibitor and 5-HT(1B/1D) receptor antagonist: effects on extracellular levels of 5-hydroxytryptamine in the guinea pig and rat. | 2001 Nov 30 |
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MDMA and fenfluramine alter the response of the circadian clock to a serotonin agonist in vitro. | 2001 Nov 30 |
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Fluorometric determination of DL-fenfluramine, DL-norfenfluramine and phentermine in plasma by achiral and chiral high-performance liquid chromatography. | 2001 Nov 5 |
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Monoamine oxidase inhibition is unlikely to be relevant to the risks associated with phentermine and fenfluramine: a comparison with their abilities to evoke monoamine release. | 2001 Oct |
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Operation for anorexigen-associated valvular heart disease. | 2001 Oct |
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High performance liquid chromatography with UV detection for the simultaneous determination of sympathomimetic amines using 4-(4,5-diphenyl-1H-imidazole-2-yl)benzoyl chloride as a label. | 2001 Oct |
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Acute effects of D-fenfluramine on simultaneous measures of aggressive escape and impulsive responses of adult males with and without a history of conduct disorder. | 2001 Sep |
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Acute anorectic effect of single and combined drugs in mice using a non-deprivation protocol. | 2001 Sep |
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Risk factors for pulmonary arterial hypertension. | 2001 Sep |
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The relationship between health-related quality of life and weight loss. | 2001 Sep |
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Anorexigen-induced pulmonary hypertension and the serotonin (5-HT) hypothesis: lessons for the future in pathogenesis. | 2002 |
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Retest reliability of prolactin response to dl-fenfluramine challenge in adults. | 2002 Feb |
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Pharmacological studies of the acute effects of (+)-3,4-methylenedioxymethamphetamine on locomotor activity: role of 5-HT(1B/1D) and 5-HT(2) receptors. | 2002 Jan |
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Is long-term heavy alcohol consumption toxic for brain serotonergic neurons? Relationship between years of excessive alcohol consumption and serotonergic neurotransmission. | 2002 Jan 1 |
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Inhibition of cocaine self-administration by fluoxetine or D-fenfluramine combined with phentermine. | 2002 Jan-Feb |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/dexfenfluramine.html
Usual Adult Dose for Weight Loss
15 mg orally twice a day, with meals.
Doses above 30 mg/day are not recommended.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10924931
Dexfenfluramine (10(-7)-10(-4) M) caused concentration-dependent contractions in rat and human pulmonary arteries with and without endothelium. In pulmonary arteries of the rat, the response to dexfenfluramine was nearly abolished by treatment with the alpha-adrenoceptor antagonists, phentolamine (10(-6) M) or prazosin (10(-7) M). In human pulmonary arteries, the concentration-response curve to dexfenfluramine was unaltered by the presence of phentolamine (10(-6) M), prazosin (10(-7) M), ketanserin (10(-6) M), or indomethacin (3x10(-6) M).
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Classification Tree | Code System | Code | ||
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DEA NO. |
1670
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NCI_THESAURUS |
C29728
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NCI_THESAURUS |
C47794
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CHEMBL248702
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3239-45-0
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DD-52
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59730
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