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 |
---|---|---|
The effect of cold and diazepam on the toxicity of fenfluramine in mice. | 1975 Mar 15 |
|
[Appetite suppressants and heart valve disorders]. | 1999 Sep |
|
Histologic changes in three explanted native cardiac valves following use of fenfluramines. | 1999 Sep-Oct |
|
Valvular abnormalities and cardiovascular status following exposure to dexfenfluramine or phentermine/fenfluramine. | 2000 Apr 5 |
|
[Obesity: principles of drug therapy]. | 2000 Aug |
|
[Valvular regurgitation caused by anorectic agents]. | 2000 Dec |
|
The effect of fenfluramine on the pulmonary disposition of 5-hydroxytryptamine in the isolated perfused rat lung: a comparison with chlorphentermine. | 2000 Jan |
|
Possible role of valvular serotonin 5-HT(2B) receptors in the cardiopathy associated with fenfluramine. | 2000 Jan |
|
Complex vascular lesions at autopsy in a patient with phentermine-fenfluramin. | 2000 Jun |
|
Anorexigens and pulmonary hypertension in the United States: results from the surveillance of North American pulmonary hypertension. | 2000 Mar |
|
Diet drug-related cardiac valve disease: the Mayo Clinic echocardiographic laboratory experience. | 2000 May |
|
Fenfluramine and phentermine and cardiovascular findings: effect of treatment duration on prevalence of valve abnormalities. | 2000 May 2 |
|
Understanding the neurobiology of suicidal behavior. | 2001 |
|
Neurotransmitter and hormonal background of hostility in anorexia nervosa. | 2001 |
|
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 |
|
The quest for biological correlates of social phobia: an interim assessment. | 2001 Apr |
|
Comparison of [(18)F]altanserin and [(18)F]deuteroaltanserin for PET imaging of serotonin(2A) receptors in baboon brain: pharmacological studies. | 2001 Apr |
|
Anorectic drugs and pulmonary hypertension from the bedside to the bench. | 2001 Apr |
|
Appetite suppressants and valvular heart disease. | 2001 Apr |
|
Relationship between 5-HT function and impulsivity and aggression in male offenders with personality disorders. | 2001 Apr |
|
Cataleptic effect of neurosteroid 3alpha-hydroxy-5alpha-pregnan-20-one in mice: modulation by serotonergic agents. | 2001 Apr 13 |
|
Association between selective serotonin-reuptake inhibitor therapy and heart valve regurgitation. | 2001 Apr 15 |
|
Fenfluramine-induced pulmonary vasoconstriction: role of serotonin receptors and potassium channels. | 2001 Aug |
|
Effect of 5-HT on binding of [(11)C] WAY 100635 to 5-HT(IA) receptors in rat brain, assessed using in vivo microdialysis nd PET after fenfluramine. | 2001 Aug |
|
Relationship between central serotonergic neurotransmission and reduction in alcohol intake by citalopram. | 2001 Aug 1 |
|
Aortic and mitral fenfluramine-phentermine valvulopathy in 64 patients treated with anorectic agents. | 2001 Dec |
|
PET neuroimaging of clomipramine challenge in humans: focus on the thalamus. | 2001 Feb 16 |
|
Low risk of significant echocardiographic valvulopathy in patients treated with anorectic drugs. | 2001 Jul |
|
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 |
|
Prolactin response to d-fenfluramine in postmenopausal women on and off ERT: comparison with young women. | 2001 Jul |
|
"Diet pills" and major depression in the Canadian population. | 2001 Jun |
|
3,4-Methylenedioxymethamphetamine (MDMA) as a unique model of serotonin receptor function and serotonin-dopamine interactions. | 2001 Jun |
|
Transcranial magnetic stimulation and antidepressive drugs share similar cellular effects in rat hippocampus. | 2001 Jun |
|
Echocardiographic examination of women previously treated with fenfluramine: long-term follow-up of a randomized, double-blind, placebo-controlled trial. | 2001 Jun 11 |
|
Bitter pills, bad medicine. | 2001 Jun 4 |
|
In vitro reaction of formaldehyde with fenfluramine: conversion to N-methyl fenfluramine. | 2001 Mar |
|
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 |
|
Stress hormone dysregulation at rest and after serotonergic stimulation among alcohol-dependent men with extended abstinence and controls. | 2001 May |
|
Decreased tryptophan availability but normal post-synaptic 5-HT2c receptor sensitivity in chronic fatigue syndrome. | 2001 May |
|
1-(m-chlorophenyl)piperazine (mCPP) dissociates in vivo serotonin release from long-term serotonin depletion in rat brain. | 2001 May |
|
Too late, again? | 2001 May-Jun |
|
[Serotonin receptor changes in depression: evidences and limitations]. | 2001 May-Jun |
|
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 |
|
MDMA and fenfluramine alter the response of the circadian clock to a serotonin agonist in vitro. | 2001 Nov 30 |
|
Neuroendocrine effects of d-fenfluramine and bromocriptine following repeated smoked cocaine in humans. | 2001 Sep 1 |
|
Anorexigen-induced pulmonary hypertension and the serotonin (5-HT) hypothesis: lessons for the future in pathogenesis. | 2002 |
|
Retest reliability of prolactin response to dl-fenfluramine challenge in adults. | 2002 Feb |
|
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 |
|
Is long-term heavy alcohol consumption toxic for brain serotonergic neurons? Relationship between years of excessive alcohol consumption and serotonergic neurotransmission. | 2002 Jan 1 |
|
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).
Name | Type | Language | ||
---|---|---|---|---|
|
Preferred Name | English | ||
|
Official Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
DEA NO. |
1670
Created by
admin on Mon Mar 31 18:15:32 GMT 2025 , Edited by admin on Mon Mar 31 18:15:32 GMT 2025
|
||
|
CFR |
21 CFR 216.24
Created by
admin on Mon Mar 31 18:15:32 GMT 2025 , Edited by admin on Mon Mar 31 18:15:32 GMT 2025
|
||
|
NCI_THESAURUS |
C29728
Created by
admin on Mon Mar 31 18:15:32 GMT 2025 , Edited by admin on Mon Mar 31 18:15:32 GMT 2025
|
||
|
NCI_THESAURUS |
C47794
Created by
admin on Mon Mar 31 18:15:32 GMT 2025 , Edited by admin on Mon Mar 31 18:15:32 GMT 2025
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
CHEMBL248702
Created by
admin on Mon Mar 31 18:15:32 GMT 2025 , Edited by admin on Mon Mar 31 18:15:32 GMT 2025
|
PRIMARY | |||
|
3239-45-0
Created by
admin on Mon Mar 31 18:15:32 GMT 2025 , Edited by admin on Mon Mar 31 18:15:32 GMT 2025
|
PRIMARY | |||
|
DD-52
Created by
admin on Mon Mar 31 18:15:32 GMT 2025 , Edited by admin on Mon Mar 31 18:15:32 GMT 2025
|
PRIMARY | |||
|
DTXSID7048871
Created by
admin on Mon Mar 31 18:15:32 GMT 2025 , Edited by admin on Mon Mar 31 18:15:32 GMT 2025
|
PRIMARY | |||
|
100000087765
Created by
admin on Mon Mar 31 18:15:32 GMT 2025 , Edited by admin on Mon Mar 31 18:15:32 GMT 2025
|
PRIMARY | |||
|
m5274
Created by
admin on Mon Mar 31 18:15:32 GMT 2025 , Edited by admin on Mon Mar 31 18:15:32 GMT 2025
|
PRIMARY | Merck Index | ||
|
155142
Created by
admin on Mon Mar 31 18:15:32 GMT 2025 , Edited by admin on Mon Mar 31 18:15:32 GMT 2025
|
PRIMARY | RxNorm | ||
|
59730
Created by
admin on Mon Mar 31 18:15:32 GMT 2025 , Edited by admin on Mon Mar 31 18:15:32 GMT 2025
|
PRIMARY | |||
|
C75111
Created by
admin on Mon Mar 31 18:15:32 GMT 2025 , Edited by admin on Mon Mar 31 18:15:32 GMT 2025
|
PRIMARY | |||
|
66264
Created by
admin on Mon Mar 31 18:15:32 GMT 2025 , Edited by admin on Mon Mar 31 18:15:32 GMT 2025
|
PRIMARY | |||
|
SUB01629MIG
Created by
admin on Mon Mar 31 18:15:32 GMT 2025 , Edited by admin on Mon Mar 31 18:15:32 GMT 2025
|
PRIMARY | |||
|
221-806-0
Created by
admin on Mon Mar 31 18:15:32 GMT 2025 , Edited by admin on Mon Mar 31 18:15:32 GMT 2025
|
PRIMARY | |||
|
PM28L0FHNP
Created by
admin on Mon Mar 31 18:15:32 GMT 2025 , Edited by admin on Mon Mar 31 18:15:32 GMT 2025
|
PRIMARY |
ACTIVE MOIETY
SUBSTANCE RECORD