Pitolisant

{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 464208162 | ImageFile= Pitolisant skeletal.svg | ImageSize=200px | IUPACName=1-{3-[3-(4-Chlorophenyl)propoxy]propyl}piperidine | OtherNames= BF2.649 |Section1=! colspan=2 style="background: #f8eaba; text-align: center;" |Identifiers

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CAS Number

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903576-44-3^N

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3D model (JSmol)

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Interactive image

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| ChEMBL

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ChEMBL462605^Y

|- | ChemSpider

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8123714^Y

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PubChem CID

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9948102

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CompTox Dashboard (EPA)

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DTXSID30957654

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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^Y
Key: NNACHAUCXXVJSP-UHFFFAOYSA-N^Y
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

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SMILES

Clc1ccc(cc1)CCCOCCCN2CCCCC2

|- |Section2=! colspan=2 style="background: #f8eaba; text-align: center;" |Properties

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Chemical formula

| C₁₇H₂₆ClNO

|- | Molar mass

| 295.846 g/mol

|- |Section3= |Section6=! colspan=2 style="background: #f8eaba; text-align: center;" |Pharmacology

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ATC code

| N07XX11 (WHO) |- }}

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

^ 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.
^ 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
^ 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
^ ^a ^b Prous Science: Molecule of the Month September 2011
^ 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
^ 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.
^ 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.

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[pmid16376822-1] 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

[Prous-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

[pmid18673168-6] 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.

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