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
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C12H16F3N |
Molecular Weight | 231.2573 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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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The effect of cold and diazepam on the toxicity of fenfluramine in mice. | 1975 Mar 15 |
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[Development of pulmonary hypertension and multi-valvular damage caused by appetite depressants]. | 1998 Dec 1 |
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Dose effect of fenfluramine-phentermine in the production of valvular heart disease. | 1999 Apr |
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Echocardiographic prevalence of mitral and/or aortic regurgitation in patients exposed to either fenfluramine-phentermine combination or to dexfenfluramine. | 1999 Dec 1 |
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Serial echocardiographic and clinical evaluation of valvular regurgitation before, during, and after treatment with fenfluramine or dexfenfluramine and mazindol or phentermine. | 1999 Jul |
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Pharmaceutical cost savings of treating obesity with weight loss medications. | 1999 Nov |
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Prevalence and determinants of valvulopathy in patients treated with dexfenfluramine. | 1999 Nov 23 |
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The promotion effect of anorectic drugs on aflatoxin B(1)-induced hepatic preneoplastic foci. | 1999 Sep |
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Histologic changes in three explanted native cardiac valves following use of fenfluramines. | 1999 Sep-Oct |
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[Obesity: principles of drug therapy]. | 2000 Aug |
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Evidence for possible involvement of 5-HT(2B) receptors in the cardiac valvulopathy associated with fenfluramine and other serotonergic medications. | 2000 Dec 5 |
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[Anorectics and pulmonary hypertension]. | 2000 Feb 16 |
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Dose and duration of fenfluramine-phentermine therapy impacts the risk of significant valvular heart disease. | 2000 Jul 1 |
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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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Association between selective serotonin-reuptake inhibitor therapy and heart valve regurgitation. | 2001 Apr 15 |
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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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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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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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Lack of effect of HPA axis hyperactivity on hormonal responses to d-fenfluramine in major depressed patients: implications for pathogenesis of suicidal behaviour. | 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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3,4-Methylenedioxymethamphetamine (MDMA) as a unique model of serotonin receptor function and serotonin-dopamine interactions. | 2001 Jun |
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Transcranial magnetic stimulation and antidepressive drugs share similar cellular effects in rat hippocampus. | 2001 Jun |
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Modafinil does not affect serotonin efflux from rat frontal cortex synaptosomes: comparison with known serotonergic drugs. | 2001 Mar 16 |
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Medial versus lateral parabrachial nucleus lesions in the rat: effects on cholecystokinin- and D-fenfluramine-induced anorexia. | 2001 Mar 16 |
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In vivo binding properties of [carbonyl-11C]WAY-100635: effect of endogenous serotonin. | 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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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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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 anorectic effect of single and combined drugs in mice using a non-deprivation protocol. | 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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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).
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:59:25 GMT 2023
by
admin
on
Fri Dec 15 15:59:25 GMT 2023
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Record UNII |
PM28L0FHNP
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Record Status |
Validated (UNII)
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Record Version |
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DEA NO. |
1670
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C29728
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NCI_THESAURUS |
C47794
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |