U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C12H16F3N
Molecular Weight 231.2573
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEXFENFLURAMINE

SMILES

CCN[C@@H](C)CC1=CC=CC(=C1)C(F)(F)F

InChI

InChIKey=DBGIVFWFUFKIQN-VIFPVBQESA-N
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

HIDE SMILES / InChI
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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Understanding the neurobiology of suicidal behavior.
2001
Neuroendocrine responses to fenfluramine and its relationship to personality in alcoholism.
2001
High-speed liquid chromatography/tandem mass spectrometry using a monolithic column for high-throughput bioanalysis.
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
Neuroendocrine serotonergic and dopaminergic responsivity in male schizophrenic patients during treatment with neuroleptics and after switch to risperidone.
2001 Aug
Hypothalamo-pituitary-adrenal axis dysfunction in chronic fatigue syndrome, and the effects of low-dose hydrocortisone therapy.
2001 Aug
Effects of dietary sucrose on hippocampal serotonin release: a microdialysis study in the freely-moving rat.
2001 Aug
Evidence that hypophagia induced by d-fenfluramine and d-norfenfluramine in the rat is mediated by 5-HT2C receptors.
2001 Aug
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
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
Pharmacologic options for the treatment of obesity.
2001 Jul 15
"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
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
Rapid clot formation and abnormal fibrin structure in a symptomatic patient taking fenfluramine--a case report.
2001 May
Decreased tryptophan availability but normal post-synaptic 5-HT2c receptor sensitivity in chronic fatigue syndrome.
2001 May
Serotonin transporter promoter polymorphism is associated with attenuated prolactin response to fenfluramine.
2001 May 8
Too late, again?
2001 May-Jun
[Serotonin receptor changes in depression: evidences and limitations].
2001 May-Jun
Effects of endogenous neurotransmitters on the in vivo binding of dopamine and 5-HT radiotracers in mice.
2001 Nov
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
Fluorometric determination of DL-fenfluramine, DL-norfenfluramine and phentermine in plasma by achiral and chiral high-performance liquid chromatography.
2001 Nov 5
Fenfluramine and phentermine.
2001 Nov 6
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
Operation for anorexigen-associated valvular heart disease.
2001 Oct
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
Clinical and echocardiographic follow-up of patients previously treated with dexfenfluramine or phentermine/fenfluramine.
2001 Oct 24-31
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
Acute anorectic effect of single and combined drugs in mice using a non-deprivation protocol.
2001 Sep
Risk factors for pulmonary arterial hypertension.
2001 Sep
The relationship between health-related quality of life and weight loss.
2001 Sep
Prolactin response to dl-fenfluramine challenge before and after treatment with paroxetine.
2001 Sep
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

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
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
DEXFENFLURAMINE
HSDB   INN   VANDF   WHO-DD  
INN  
Official Name English
dexfenfluramine [INN]
Common Name English
DEXFENFLURAMINE [VANDF]
Common Name English
FENFLURAMINE D-FORM
MI  
Common Name English
FENFLURAMINE D-FORM [MI]
Common Name English
DEXFENFLURAMINE [HSDB]
Common Name English
D-(+)-FENFLURAMINE
Common Name English
S 5614
Code English
BENZENEETHANAMINE, N-ETHYL-.ALPHA.-METHYL-3-(TRIFLUOROMETHYL)-, (S)-
Systematic Name English
PHENETHYLAMINE, N-ETHYL-.ALPHA.-METHYL-M-(TRIFLUOROMETHYL)-, (S)-
Systematic Name English
BENZENEETHANAMINE, N-ETHYL-.ALPHA.-METHYL-3-(TRIFLUOROMETHYL)-, (.ALPHA.S)-
Systematic Name English
Dexfenfluramine [WHO-DD]
Common Name English
D-FENFLURAMINE
Common Name English
(+)-(S)-N-ETHYL-A-METHYL-M-(TRIFLUOROMETHYL)PHENETHYLAMINE
Common Name English
J13.711A
Code English
(+)-FENFLURAMINE
Common Name English
(.ALPHA.S)-N-ETHYL-.ALPHA.-METHYL-3-(TRIFLUOROMETHYL)BENZENEETHANAMINE
Common Name English
ISOLIPAN
Brand Name English
(S)-(+)-FENFLURAMINE
Common Name English
Classification Tree Code System Code
WHO-VATC QA08AA04
Created by admin on Sat Dec 16 05:12:17 GMT 2023 , Edited by admin on Sat Dec 16 05:12:17 GMT 2023
NCI_THESAURUS C47794
Created by admin on Sat Dec 16 05:12:17 GMT 2023 , Edited by admin on Sat Dec 16 05:12:17 GMT 2023
WHO-ATC A08AA04
Created by admin on Sat Dec 16 05:12:17 GMT 2023 , Edited by admin on Sat Dec 16 05:12:17 GMT 2023
DEA NO. 1670
Created by admin on Sat Dec 16 05:12:17 GMT 2023 , Edited by admin on Sat Dec 16 05:12:17 GMT 2023
Code System Code Type Description
CAS
5220-91-7
Created by admin on Sat Dec 16 05:12:17 GMT 2023 , Edited by admin on Sat Dec 16 05:12:17 GMT 2023
SUPERSEDED
CHEBI
439329
Created by admin on Sat Dec 16 05:12:17 GMT 2023 , Edited by admin on Sat Dec 16 05:12:17 GMT 2023
PRIMARY
HSDB
7356
Created by admin on Sat Dec 16 05:12:17 GMT 2023 , Edited by admin on Sat Dec 16 05:12:17 GMT 2023
PRIMARY
EVMPD
SUB07028MIG
Created by admin on Sat Dec 16 05:12:17 GMT 2023 , Edited by admin on Sat Dec 16 05:12:17 GMT 2023
PRIMARY
SMS_ID
100000083203
Created by admin on Sat Dec 16 05:12:17 GMT 2023 , Edited by admin on Sat Dec 16 05:12:17 GMT 2023
PRIMARY
DRUG BANK
DB01191
Created by admin on Sat Dec 16 05:12:17 GMT 2023 , Edited by admin on Sat Dec 16 05:12:17 GMT 2023
PRIMARY
EPA CompTox
DTXSID001025754
Created by admin on Sat Dec 16 05:12:17 GMT 2023 , Edited by admin on Sat Dec 16 05:12:17 GMT 2023
PRIMARY
MESH
D020372
Created by admin on Sat Dec 16 05:12:17 GMT 2023 , Edited by admin on Sat Dec 16 05:12:17 GMT 2023
PRIMARY
MERCK INDEX
m5274
Created by admin on Sat Dec 16 05:12:17 GMT 2023 , Edited by admin on Sat Dec 16 05:12:17 GMT 2023
PRIMARY Merck Index
ChEMBL
CHEMBL248702
Created by admin on Sat Dec 16 05:12:17 GMT 2023 , Edited by admin on Sat Dec 16 05:12:17 GMT 2023
PRIMARY
PUBCHEM
66265
Created by admin on Sat Dec 16 05:12:17 GMT 2023 , Edited by admin on Sat Dec 16 05:12:17 GMT 2023
PRIMARY
DRUG CENTRAL
832
Created by admin on Sat Dec 16 05:12:17 GMT 2023 , Edited by admin on Sat Dec 16 05:12:17 GMT 2023
PRIMARY
CAS
3239-44-9
Created by admin on Sat Dec 16 05:12:17 GMT 2023 , Edited by admin on Sat Dec 16 05:12:17 GMT 2023
PRIMARY
RXCUI
3268
Created by admin on Sat Dec 16 05:12:17 GMT 2023 , Edited by admin on Sat Dec 16 05:12:17 GMT 2023
PRIMARY RxNorm
NCI_THESAURUS
C83665
Created by admin on Sat Dec 16 05:12:17 GMT 2023 , Edited by admin on Sat Dec 16 05:12:17 GMT 2023
PRIMARY
WIKIPEDIA
DEXFENFLURAMINE
Created by admin on Sat Dec 16 05:12:17 GMT 2023 , Edited by admin on Sat Dec 16 05:12:17 GMT 2023
PRIMARY
INN
5818
Created by admin on Sat Dec 16 05:12:17 GMT 2023 , Edited by admin on Sat Dec 16 05:12:17 GMT 2023
PRIMARY
CAS
5220-90-6
Created by admin on Sat Dec 16 05:12:17 GMT 2023 , Edited by admin on Sat Dec 16 05:12:17 GMT 2023
SUPERSEDED
FDA UNII
E35R3G56OV
Created by admin on Sat Dec 16 05:12:17 GMT 2023 , Edited by admin on Sat Dec 16 05:12:17 GMT 2023
PRIMARY