fenfluramine   Click here for help

GtoPdb Ligand ID: 4613

Synonyms: Adifax® | Fintepla® | Pondimin® | ZX008
Approved drug
fenfluramine is an approved drug (FDA (2020))
Compound class: Synthetic organic
Comment: The approved drug was called dexfenfluramine, but was withdrawn from use due to adverse cardiac events [1,3].
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 12.03
Molecular weight 231.12
XLogP 3.5
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CCNC(Cc1cccc(c1)C(F)(F)F)C
Isomeric SMILES CCNC(Cc1cccc(c1)C(F)(F)F)C
InChI 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
InChI Key DBGIVFWFUFKIQN-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
This drug was approved as a weight-loss aid, which suppressed appetite for carbohydrates but was withdrawn from the market for this use. It has subsequently been repositioned as an anti-seizure drug, for use in paediatric onset epilepsy syndromes. In June 2020, the FDA granted approval for an oral solution of fenfluramine (Fintepla®) as a treatment for seizures associated with Dravet syndrome in patients ≥2 years of age [4].
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Dexfenfluramine binds to and inhibits the serotonin reuptake pump causing elevated serotonin levels.This results in elevated serotoninergic transmission in the hypothalamic centres which control feeding behavior, which manifests as a decreased appetite for carbohydrate. The drug also affects the activity of the serotonin 5HT2C receptor [5].
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT03936777 A Study to Investigate the Long-Term Safety of ZX008 (Fenfluramine Hydrochloride) Oral Solution in Children and Adults With Epileptic Encephalopathy Including Dravet Syndrome and Lennox-Gastaut Syndrome Phase 3 Interventional Zogenix, Inc.
NCT03861871 Fenfluramine in CDKL5 Deficiency Disorder (CDD) Phase 2 Interventional NYU Langone Health
NCT04437004 Treatment of Dravet Syndrome With Fenfluramine (Expanded Access Protocol) Expanded Access University of California, Los Angeles