Pitolisant hydrochlorideProduct ingredient for Pitolisant
- Name
- Pitolisant hydrochloride
- Drug Entry
- Pitolisant
Pitolisant is a selective antagonist or inverse agonist of the histamine H3 receptor used to treat type 1 or 2 narcolepsy.8 Narcolepsy is a chronic neurological disorder that affects 1 in 2,000 individuals and is characterized by excessive daytime sleepiness, abnormal REM sleep manifestations, sleep paralysis and hypnagogic hallucinations.4 About 60-70% of patients with narcolepsy experience cataplexy, which is a sudden loss of muscle tone triggered by positive or negative emotions.1 Histaminergic neuron signalling in the brain plays a role in maintaining wakefulness; by blocking histamine autoreceptors, pitolisant enhances the activity of histaminergic neurons, as well as increasing the signalling of other neurotransmitters in the brain.
In a European clinical trial of adult patients with narcolepsy, there was a reduction in the Epworth Sleepiness Scale (ESS) score from pitolisant therapy compared to placebo.3 The therapeutic effectiveness of pitolisant was comparable to that of modafinil.3 Pitolisant therapy was also effective in treating refractory sleepiness in adolescent patients with narcolepsy, where it decreased ESS score and increased the mean sleep onset latency.2 Adolescent patients with cataplexy also experienced a slight improvement in the frequency and severity of symptoms 2; however, the safety of use in adolescent or paediatric patients have not been established with pitolisant. Commonly marketed under the trade name Wakix, oral pitolisant was approved by the EMA in 2016 7 for the treatment of narcolepsy with or without cataplexy. FDA approved the use of pitolisant in 2019 for excessive daytime sleepiness (EDS) associated with narcolepsy in adults.8
- Accession Number
- DBSALT002888
- Structure
- Synonyms
- Ciproxidine / Pitolisant HCl / Tiprolisant
- UNII
- YV33CH63HI
- CAS Number
- 903576-44-3
- Weight
- Average: 332.31
Monoisotopic: 331.1469699 - Chemical Formula
- C17H27Cl2NO
- InChI Key
- XLFKECRRMPOAQS-UHFFFAOYSA-N
- InChI
- InChI=1S/C17H26ClNO.ClH/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;1H
- IUPAC Name
- 1-{3-[3-(4-chlorophenyl)propoxy]propyl}piperidine hydrochloride
- SMILES
- Cl.ClC1=CC=C(CCCOCCCN2CCCCC2)C=C1
- External Links
- ChemSpider
- 9726467
- Wikipedia
- Pitolisant
- Predicted Properties
Property Value Source Water Solubility 0.00142 mg/mL ALOGPS logP 4.47 ALOGPS logP 4.12 Chemaxon logS -5.3 ALOGPS pKa (Strongest Basic) 9.67 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 12.47 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 86.81 m3·mol-1 Chemaxon Polarizability 35.5 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon