Pitolisant

Pitolisant

Names
IUPAC name 1-{3-[3-(4-Chlorophenyl)propoxy]propyl}piperidine
Other names BF2.649
Identifiers
CAS Number	903576-44-3
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL462605
ChemSpider	8123714
PubChem	9948102
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 Key: NNACHAUCXXVJSP-UHFFFAOYSA-N InChI=1/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 Key: NNACHAUCXXVJSP-UHFFFAOYAL
SMILES Clc1ccc(cc1)CCCOCCCN2CCCCC2
Properties
Chemical formula	C17H26ClNO
Molar mass	295.846 g/mol
Pharmacology
ATC code	N07XX11 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Pitolisant (INN) or tiprolisant (USAN) is a histamine receptor inverse agonist/antagonist selective for the H₃ subtype.^[1] It has stimulant and nootropic effects in animal studies,^[2] and may have several medical applications, having been researched for the treatment of narcolepsy, for which it has been granted orphan drug status in the EU and US.^[3][4] It is currently in clinical trials for schizophrenia and Parkinson's disease.^[4][5][6]

Pitolisant was developed by Jean-Charles Schwartz, Walter Schunack and colleagues after the former discovered H₃ receptors.^[7] Pitolisant was the first clinically used H₃ receptor inverse agonist.

References

1. Celanire S, Wijtmans M, Talaga P, Leurs R, de Esch IJ (December 2005). "Keynote review: histamine H3 receptor antagonists reach out for the clinic". Drug Discov. Today. 10 (23-24): 1613–27. doi:10.1016/S1359-6446(05)03625-1. PMID 16376822.
2. Ligneau X, Perrin D, Landais L, Camelin JC, Calmels TP, Berrebi-Bertrand I, Lecomte JM, Parmentier R, Anaclet C, Lin JS, Bertaina-Anglade V, la Rochelle CD, d'Aniello F, Rouleau A, Gbahou F, Arrang JM, Ganellin CR, Stark H, Schunack W, Schwartz JC. BF2.649 [1-{3-[3-(4-Chlorophenyl)propoxy]propyl}piperidine, hydrochloride], a nonimidazole inverse agonist/antagonist at the human histamine H3 receptor: Preclinical pharmacology. Journal of Pharmacology and Experimental Therapeutics. 2007 Jan;320(1):365-75. PMID 17005916
3. Lin JS, Dauvilliers Y, Arnulf I, Bastuji H, Anaclet C, Parmentier R, Kocher L, Yanagisawa M, Lehert P, Ligneau X, Perrin D, Robert P, Roux M, Lecomte JM, Schwartz JC. An inverse agonist of the histamine H(3) receptor improves wakefulness in narcolepsy: studies in orexin-/- mice and patients. Neurobiology of Disease. 2008 Apr;30(1):74-83. PMID 18295497
4. Prous Science: Molecule of the Month September 2011
5. Ligneau X, Landais L, Perrin D, Piriou J, Uguen M, Denis E, Robert P, Parmentier R, Anaclet C, Lin JS, Burban A, Arrang JM, Schwartz JC. Brain histamine and schizophrenia: potential therapeutic applications of H3-receptor inverse agonists studied with BF2.649. Biochemical Pharmacology. 2007 Apr 15;73(8):1215-24. PMID 17343831
6. Stocking EM, Letavic MA (2008). "Histamine H3 antagonists as wake-promoting and pro-cognitive agents". Current Topics in Medicinal Chemistry. 8 (11): 988–1002. doi:10.2174/156802608784936728. PMID 18673168.
7. Schwartz, Jean-Charles (May 2011). "The histamine H3 receptor: from discovery to clinical trials with pitolisant". BPJ. doi:10.1111/j.1476-5381.2011.01286.x.