Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C12H16F3N.C10H16O4 |
Molecular Weight | 431.489 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1(C)[C@H](CC[C@@]1(C)C(O)=O)C(O)=O.CCN[C@@H](C)CC2=CC(=CC=C2)C(F)(F)F
InChI
InChIKey=GBMYZGXLAHAFPC-JGTDEUSISA-N
InChI=1S/C12H16F3N.C10H16O4/c1-3-16-9(2)7-10-5-4-6-11(8-10)12(13,14)15;1-9(2)6(7(11)12)4-5-10(9,3)8(13)14/h4-6,8-9,16H,3,7H2,1-2H3;6H,4-5H2,1-3H3,(H,11,12)(H,13,14)/t9-;6-,10+/m01/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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Dose-effect of fenfluramine use on the severity of valvular heart disease among fen-phen patients with valvulopathy. | 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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Valvular abnormalities and cardiovascular status following exposure to dexfenfluramine or phentermine/fenfluramine. | 2000 Apr 5 |
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[Valvular regurgitation caused by anorectic agents]. | 2000 Dec |
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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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Anorexigens and pulmonary hypertension in the United States: results from the surveillance of North American pulmonary hypertension. | 2000 Mar |
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Diet drug-related cardiac valve disease: the Mayo Clinic echocardiographic laboratory experience. | 2000 May |
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The quest for biological correlates of social phobia: an interim assessment. | 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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Hypothalamo-pituitary-adrenal axis dysfunction in chronic fatigue syndrome, and the effects of low-dose hydrocortisone therapy. | 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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Fenfluramine-induced pulmonary vasoconstriction: role of serotonin receptors and potassium channels. | 2001 Aug |
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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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Silver lining to the cloud over anorexogen-related cardiac valvulopathy? | 2001 Feb 20 |
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The progression of fenfluramine-associated valvular heart disease assessed by echocardiography. | 2001 Feb 20 |
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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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Stress hormone dysregulation at rest and after serotonergic stimulation among alcohol-dependent men with extended abstinence and controls. | 2001 May |
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Decreased tryptophan availability but normal post-synaptic 5-HT2c receptor sensitivity in chronic fatigue syndrome. | 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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Effects of endogenous neurotransmitters on the in vivo binding of dopamine and 5-HT radiotracers in mice. | 2001 Nov |
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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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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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Clinical and echocardiographic follow-up of patients previously treated with dexfenfluramine or phentermine/fenfluramine. | 2001 Oct 24-31 |
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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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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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97158-54-8
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ACTIVE MOIETY
SUBSTANCE RECORD