Structure via PubChem · Public domain (PubChem)
dexfenfluramine
Sign in to saveAlso known as (S)-fenfluramine, D-N-Ethyl-alpha-methyl-m-trifluoromethylphenethylamine, (S)-N-Ethyl-1-[3-(trifluoromethyl)phenyl]propan-2-amine, (+)-fenfluramine, dextrofenfluramine
Chemical data
- Formula
- C12H16F3N
- Molecular weight
- 231.26 g/mol
- IUPAC name
- (2S)-N-ethyl-1-[3-(trifluoromethyl)phenyl]propan-2-amine
- SMILES
- CCN[C@@H](C)CC1=CC(=CC=C1)C(F)(F)F
- InChIKey
- DBGIVFWFUFKIQN-VIFPVBQESA-N
- XLogP
- 3.4
- Polar surface area
- 12 Ų
- H-bond donors
- 1
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
Withdrawn- Max clinical phase
- Approved
- Molecule type
- Small molecule
- Indications
- obesity
via ChEMBL · EBI
Research
595 papers- Dexfenfluramine.Lancet (London, England) · 1991
- Dexfenfluramine hydrochloride: an anorexigenic agent.American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists · 1997
- Dexfenfluramine.Lippincott's primary care practice · 1997
- Dexfenfluramine.Nutrition (Burbank, Los Angeles County, Calif.) · 1997
- Dexfenfluramine and feeding reward.Clinical neuropharmacology · 1988
via PubMed
Wikidata facts
- Subclass of
- (RS)-fenfluramine
- Mass
- 231.123484
- Has use
- medication
Show 8 more facts
- chemical formula
- C₁₂H₁₆F₃N
- subject has role
- serotonin receptor agonists
- isomeric SMILES
- CCN[C@@H](C)CC1=CC(=CC=C1)C(F)(F)F
- canonical SMILES
- CCNC(C)CC1=CC(=CC=C1)C(F)(F)F
- World Health Organisation international non-proprietary name
- dexfenfluramine
- defined daily dose
- 30
- Commons category
- Dexfenfluramine
- legal status (medicine)
- boxed warning
Sources (6)
via Wikidata · CC0
~2 min read
Encyclopedic overview
3 sectionsContents
- See also
- References
- External links
Dexfenfluramine, formerly sold under the brand name Redux, is a serotonergic drug that was used as an appetite suppressant to promote weight loss. It is the d-enantiomer of fenfluramine and is structurally similar to amphetamine, but lacks any psychologically stimulating effects.
Dexfenfluramine was, for some years in the mid-1990s, approved by the United States Food and Drug Administration (FDA) for the purposes of weight loss. However, following multiple concerns about its cardiovascular side effects, the FDA withdrew the approval in 1997. After it was removed in the US, dexfenfluramine was also pulled out in other global markets. It was later superseded by sibutramine, which, although initially considered a safer alternative to both dexfenfluramine and fenfluramine, was likewise removed from the US market in 2010.
Excerpted from Wikipedia’s “dexfenfluramine” article, available under the CC BY-SA 4.0 licence.