pitolisant   Click here for help

GtoPdb Ligand ID: 8924

Synonyms: BF2.649 | tiprolisant [USAN] | Wakix®
Approved drug
pitolisant is an approved drug (EMA (2016), FDA (2019))
Compound class: Synthetic organic
Comment: Pitolisant is a selective antagonist/inverse agonist of the histamine H3 receptor [7-8,11].
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 8
Topological polar surface area 12.47
Molecular weight 295.17
XLogP 3.94
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES Clc1ccc(cc1)CCCOCCCN1CCCCC1
Isomeric SMILES Clc1ccc(cc1)CCCOCCCN1CCCCC1
InChI InChI=1S/C17H26ClNO/c18-17-9-7-16(8-10-17)6-4-14-20-15-5-13-19-11-2-1-3-12-19/h7-10H,1-6,11-15H2
InChI Key NNACHAUCXXVJSP-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Pitolisant was initially granted orphan designation as a treatment for excessive daytime sleepiness and cataplexy in patients with narcolspey in the US and across Europe. In March 2016, pitolisant received EMA marketing authorisation for the treatment of narcolepsy [2]. Phase 3 trial results were reported in 2017 [10]. It was 2019 before the FDA approved this drug for the same indication as covered by the EMA marketing authorisation.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Preclinical pharmacology of this compound is reported in [4-5], and its clinical potential is discussed in [1,3,9].
External links Click here for help