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Comment: The approved drug was called dexfenfluramine, but was withdrawn from use due to adverse cardiac events [1,3].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
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
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
Click here for help

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/)

✖
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/)
References
1. Connolly HM, Crary JL, McGoon MD, Hensrud DD, Edwards BS, Edwards WD, Schaff HV. (1997)
Valvular heart disease associated with fenfluramine-phentermine.
N Engl J Med, 337 (9): 581-8. [PMID:9271479]
2. Erickson JD, Schafer MK, Bonner TI, Eiden LE, Weihe E. (1996)
Distinct pharmacological properties and distribution in neurons and endocrine cells of two isoforms of the human vesicular monoamine transporter.
Proc Natl Acad Sci USA, 93 (10): 5166-71. [PMID:8643547]
3. Mitchell P, Hickie I, Torda T. (1992)
Propofol and ECT.
Br J Psychiatry, 161: 861-2. [PMID:1307869]
4. Pierce JG, Mithal DS. (2020)
Fenfluramine: New Treatment for Seizures in Dravet Syndrome.
Pediatr Neurol Briefs, 34: 8. [PMID:32189958]
5. Vickers SP, Dourish CT, Kennett GA. (2001)
Evidence that hypophagia induced by d-fenfluramine and d-norfenfluramine in the rat is mediated by 5-HT2C receptors.
Neuropharmacology, 41 (2): 200-9. [PMID:11489456]