Fenfluramine hydrochlorideProduct ingredient for Fenfluramine

Name
Fenfluramine hydrochloride
Drug Entry
Fenfluramine

Dravet syndrome is a pediatric encephalopathy that typically manifests within the first year of life following exposure to elevated temperatures. It is characterized by recurrent pharmacoresistant seizures, which increase in frequency and severity with disease progression. Concomitantly with these seizures, patients typically display delayed development and neurocognitive impairment.6,9,10,11 Fenfluramine is a serotonergic phenethylamine originally used as an appetite suppressant until concerns regarding cardiotoxicity in obese patients lead to its withdrawal from the market in 1997.6,12,13 Through its ability to modulate neurotransmission, fenfluramine has reemerged as an effective therapy against pharmacoresistant seizures, such as those involved in Dravet syndrome.3,5,8

Fenfluramine was granted initial FDA approval in 1973 prior to its withdrawal; it was granted a new FDA approval on June 25, 2020, for treatment of Dravet syndrome patients through the restricted FINTEPLA REMS program. It is currently sold under the name FINTEPLA® by Zogenix INC.16

Accession Number
DBSALT000802
Structure
Thumb
Synonyms
Fenfluramine HCl / Fenfluramine hydrochloride / Racemic fenfluramine hydrochloride
External IDs
AHR 3002 / AHR-3002 / ZX008
UNII
3KC089243P
CAS Number
404-82-0
Weight
Average: 267.718
Monoisotopic: 267.100161871
Chemical Formula
C12H17ClF3N
InChI Key
ZXKXJHAOUFHNAS-UHFFFAOYSA-N
InChI
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
IUPAC Name
ethyl({1-[3-(trifluoromethyl)phenyl]propan-2-yl})amine hydrochloride
SMILES
Cl.CCNC(C)CC1=CC=CC(=C1)C(F)(F)F
External Links
PubChem Compound
91452
ChemSpider
82580
ChEBI
59729
ChEMBL
CHEMBL2106217
Wikipedia
Fenfluramine
Predicted Properties
PropertyValueSource
Water Solubility0.0215 mg/mLALOGPS
logP3.3ALOGPS
logP3.47ChemAxon
logS-4ALOGPS
pKa (Strongest Basic)10.22ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity59.2 m3·mol-1ChemAxon
Polarizability22.74 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon