Pitolisant

Pitolisant
	13-[3-(4-hlorofenil)propoksi]propil}piperidin
Drugi nazivi	BF2.649
Identifikacija
CAS registarski broj	903576-44-3
PubChem	9948102
ChemSpider	8123714
ChEMBL	CHEMBL462605
Jmol-3D slike	Slika 1
SMILES
	Clc1ccc(cc1)CCCOCCCN2CCCCC2
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 ; Kod: 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; Kod: NNACHAUCXXVJSP-UHFFFAOYAL
Svojstva
Molekulska formula	C17H26ClNO
Molarna masa	295.85 g mol−1
	(šta je ovo?) (verifikuj) ; Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala
	Infobox references

Pitolisant (INN) ili tiprolisant (USAN) je inverzni agonist/antagonist histaminskog receptora koji je selektivan za H₃ receptor.^[5] On ima stimulantne i nootropne efekte u životinjskim studijama,^[6] i može da ima nekoliko potencijalnih medicinskih primena. Istražen je za tretman narkolepsije, i za tu indikaciju mu je odobren status orfan leka u EU i SAD.^[7]^[8] On je u kliničkim ispitivanjima za šizofreniju i Parkinsonova bolest.^[8]^[9]^[10]

Pitolisant je razvijen nakon otkrića H3 receptora.^[11] Pitolisant je prvi inverzni agonist H3 receptora sa kliničkom primenom.

Reference

↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit
↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit
↑ 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 [13-[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
↑ ^8,0 ^8,1 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. The histamine H3 receptor: from discovery to clincial trials with pitolisant. BPJ 2011 May [1]

Spoljašnje veze

Portal Hemija

[1] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit

[2] Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.

[3] Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit

[4] Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit

[pmid16376822-5] 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.

[6] 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 [13-[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

[7] 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-8] 8,0 ^8,1 Prous Science: Molecule of the Month September 2011

[9] 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

[pmid18673168-10] 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.

[11] Schwartz, Jean-Charles. The histamine H3 receptor: from discovery to clincial trials with pitolisant. BPJ 2011 May [1]

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