Pitolisant

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Pitolisant
Pitolisant skeletal.svg
Names
IUPAC name
1-{3-[3-(4-Chlorophenyl)propoxy]propyl}piperidine
Other names
BF2.649
Identifiers
903576-44-3 N
ChEMBL ChEMBL462605 YesY
ChemSpider 8123714 YesY
Jmol 3D model Interactive image
PubChem 9948102
  • 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 YesY
    Key: NNACHAUCXXVJSP-UHFFFAOYSA-N YesY
  • 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
  • Clc1ccc(cc1)CCCOCCCN2CCCCC2
Properties
C17H26ClNO
Molar mass 295.846 g/mol
Vapor pressure {{{value}}}
Pharmacology
ATC code N07XX11
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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

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  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  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. ↑ 4.0 4.1 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. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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