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

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
Structure of DEXFENFLURAMINE HYDROCHLORIDE

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

HIDE SMILES / InChI

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Treatment of obesity with fenfluramine.
1975 Jan 31
The effect of cold and diazepam on the toxicity of fenfluramine in mice.
1975 Mar 15
[Development of pulmonary hypertension and multi-valvular damage caused by appetite depressants].
1998 Dec 1
Dose effect of fenfluramine-phentermine in the production of valvular heart disease.
1999 Apr
Echocardiographic prevalence of mitral and/or aortic regurgitation in patients exposed to either fenfluramine-phentermine combination or to dexfenfluramine.
1999 Dec 1
Serial echocardiographic and clinical evaluation of valvular regurgitation before, during, and after treatment with fenfluramine or dexfenfluramine and mazindol or phentermine.
1999 Jul
Pharmaceutical cost savings of treating obesity with weight loss medications.
1999 Nov
Prevalence and determinants of valvulopathy in patients treated with dexfenfluramine.
1999 Nov 23
The promotion effect of anorectic drugs on aflatoxin B(1)-induced hepatic preneoplastic foci.
1999 Sep
Histologic changes in three explanted native cardiac valves following use of fenfluramines.
1999 Sep-Oct
[Obesity: principles of drug therapy].
2000 Aug
Evidence for possible involvement of 5-HT(2B) receptors in the cardiac valvulopathy associated with fenfluramine and other serotonergic medications.
2000 Dec 5
[Anorectics and pulmonary hypertension].
2000 Feb 16
Dose and duration of fenfluramine-phentermine therapy impacts the risk of significant valvular heart disease.
2000 Jul 1
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
Association between selective serotonin-reuptake inhibitor therapy and heart valve regurgitation.
2001 Apr 15
Effects of dietary sucrose on hippocampal serotonin release: a microdialysis study in the freely-moving rat.
2001 Aug
Fenfluramine-induced pulmonary vasoconstriction: role of serotonin receptors and potassium channels.
2001 Aug
Relationship between central serotonergic neurotransmission and reduction in alcohol intake by citalopram.
2001 Aug 1
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
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
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
Modafinil does not affect serotonin efflux from rat frontal cortex synaptosomes: comparison with known serotonergic drugs.
2001 Mar 16
Medial versus lateral parabrachial nucleus lesions in the rat: effects on cholecystokinin- and D-fenfluramine-induced anorexia.
2001 Mar 16
In vivo binding properties of [carbonyl-11C]WAY-100635: effect of endogenous serotonin.
2001 May
Serotonin transporter promoter polymorphism is associated with attenuated prolactin response to fenfluramine.
2001 May 8
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
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
Acute anorectic effect of single and combined drugs in mice using a non-deprivation protocol.
2001 Sep
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
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).
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:59:25 GMT 2023
Edited
by admin
on Fri Dec 15 15:59:25 GMT 2023
Record UNII
PM28L0FHNP
Record Status Validated (UNII)
Record Version
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Name Type Language
DEXFENFLURAMINE HYDROCHLORIDE
MART.   USAN   VANDF   WHO-DD  
USAN  
Official Name English
FENFLURAMINE D-FORM HYDROCHLORIDE [MI]
Common Name English
ADIPOMIN
Brand Name English
DEXFENFLURAMINE HYDROCHLORIDE [USAN]
Common Name English
D-FENFLURAMINE HYDROCHLORIDE
Common Name English
S-5614 HYDROCHLORIDE
Code English
S 5614 HCL
Code English
DEXFENFLURAMINE HYDROCHLORIDE [VANDF]
Common Name English
(+)-(S)-N-ETHYL-.ALPHA.-METHYL-M-(TRIFLUOROMETHYL)PHENETHYLAMINE HYDROCHLORIDE
Systematic Name English
S-5614 HCL
Code English
FENFLURAMINE D-FORM HYDROCHLORIDE
MI  
Common Name English
DEXFENFLURAMINE HYDROCHLORIDE [MART.]
Common Name English
Dexfenfluramine hydrochloride [WHO-DD]
Common Name English
(+)-FENFLURAMINE HYDROCHLORIDE
Common Name English
ADIFAX
Brand Name English
DEXFENFLURAMINE HCL
Common Name English
BENZENEETHANAMINE, N-ETHYL-.ALPHA.-METHYL-3-(TRIFLUOROMETHYL)-, HYDROCHLORIDE, (S)-
Systematic Name English
ISOMERIDE
Brand Name English
GLYPOLIX
Brand Name English
BENZENEETHANAMINE, N-ETHYL-.ALPHA.-METHYL-3-(TRIFLUOROMETHYL)-, HYDROCHLORIDE, (.ALPHA.S)-
Common Name English
Classification Tree Code System Code
DEA NO. 1670
Created by admin on Fri Dec 15 15:59:25 GMT 2023 , Edited by admin on Fri Dec 15 15:59:25 GMT 2023
NCI_THESAURUS C29728
Created by admin on Fri Dec 15 15:59:25 GMT 2023 , Edited by admin on Fri Dec 15 15:59:25 GMT 2023
NCI_THESAURUS C47794
Created by admin on Fri Dec 15 15:59:25 GMT 2023 , Edited by admin on Fri Dec 15 15:59:25 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL248702
Created by admin on Fri Dec 15 15:59:25 GMT 2023 , Edited by admin on Fri Dec 15 15:59:25 GMT 2023
PRIMARY
CAS
3239-45-0
Created by admin on Fri Dec 15 15:59:25 GMT 2023 , Edited by admin on Fri Dec 15 15:59:25 GMT 2023
PRIMARY
USAN
DD-52
Created by admin on Fri Dec 15 15:59:25 GMT 2023 , Edited by admin on Fri Dec 15 15:59:25 GMT 2023
PRIMARY
EPA CompTox
DTXSID7048871
Created by admin on Fri Dec 15 15:59:25 GMT 2023 , Edited by admin on Fri Dec 15 15:59:25 GMT 2023
PRIMARY
SMS_ID
100000087765
Created by admin on Fri Dec 15 15:59:25 GMT 2023 , Edited by admin on Fri Dec 15 15:59:25 GMT 2023
PRIMARY
MERCK INDEX
m5274
Created by admin on Fri Dec 15 15:59:25 GMT 2023 , Edited by admin on Fri Dec 15 15:59:25 GMT 2023
PRIMARY Merck Index
RXCUI
155142
Created by admin on Fri Dec 15 15:59:25 GMT 2023 , Edited by admin on Fri Dec 15 15:59:25 GMT 2023
PRIMARY RxNorm
CHEBI
59730
Created by admin on Fri Dec 15 15:59:25 GMT 2023 , Edited by admin on Fri Dec 15 15:59:25 GMT 2023
PRIMARY
NCI_THESAURUS
C75111
Created by admin on Fri Dec 15 15:59:25 GMT 2023 , Edited by admin on Fri Dec 15 15:59:25 GMT 2023
PRIMARY
PUBCHEM
66264
Created by admin on Fri Dec 15 15:59:25 GMT 2023 , Edited by admin on Fri Dec 15 15:59:25 GMT 2023
PRIMARY
EVMPD
SUB01629MIG
Created by admin on Fri Dec 15 15:59:25 GMT 2023 , Edited by admin on Fri Dec 15 15:59:25 GMT 2023
PRIMARY
ECHA (EC/EINECS)
221-806-0
Created by admin on Fri Dec 15 15:59:25 GMT 2023 , Edited by admin on Fri Dec 15 15:59:25 GMT 2023
PRIMARY
FDA UNII
PM28L0FHNP
Created by admin on Fri Dec 15 15:59:25 GMT 2023 , Edited by admin on Fri Dec 15 15:59:25 GMT 2023
PRIMARY
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