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MedKoo Cat#: 319900 | Name: Pitolisant HCl
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Pitolisant, also known as Tiprolisant, BF2649 and Ciproxidine, is a histamine receptor inverse agonist/antagonist selective for the H3 subtype. It has stimulant and nootropic effects and may have several medical applications such as treatment of narcolepsy.

Chemical Structure

Pitolisant HCl
Pitolisant HCl
CAS#903576-44-3 (HCl)

Theoretical Analysis

MedKoo Cat#: 319900

Name: Pitolisant HCl

CAS#: 903576-44-3 (HCl)

Chemical Formula: C17H27Cl2NO

Exact Mass: 295.1703

Molecular Weight: 332.31

Elemental Analysis: C, 61.44; H, 8.19; Cl, 21.34; N, 4.22; O, 4.81

Price and Availability

Size Price Availability Quantity
10mg USD 350.00
50mg USD 1,150.00
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Related CAS #
362665-56-3 (free base) 903576-44-3 (HCl) 362665-57-4 (oxalate)
Synonym
BF2.649; BF2649; BF-2649; BF2649; FUB-649, FUB649, FUB 649, BF2.649; BF 2.649; HBS-101; HBS 101; HBS101; Ciproxidine; Pitolisant, Tiprolisant; Pitolisant HCl; Pitolisant hydrochloride.
IUPAC/Chemical Name
1-(3-(3-(4-Chlorophenyl)propoxy)propyl)piperidine hydrochloride
InChi Key
XLFKECRRMPOAQS-UHFFFAOYSA-N
InChi Code
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
SMILES Code
ClC1=CC=C(CCCOCCCN2CCCCC2)C=C1.[H]Cl
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Pitolisant hydrochloride is a potent and selective nonimidazole inverse agonist at the recombinant human histamine H3 receptor (Ki=0.16 nM).
In vitro activity:
1-{3-[3-(4-Chlorophenyl)propoxy]propyl}piperidine, hydrochloride (BF2.649) is a novel, potent, and selective nonimidazole inverse agonist at the recombinant human H3 receptor. On the stimulation of guanosine 5'-O-(3-[35S]thio)triphosphate binding to this receptor, BF2.649 behaved as a competitive antagonist with a Ki value of 0.16 nM and as an inverse agonist with an EC50 value of 1.5 nM and an intrinsic activity approximately 50% higher than that of ciproxifan. Its in vitro potency was approximately 6 times lower at the rodent receptor. Reference: J Pharmacol Exp Ther. 2007 Jan;320(1):365-75. https://pubmed.ncbi.nlm.nih.gov/17005916/
In vivo activity:
The aim of this study was to investigate the influence of pitolisant - H3 histamine antagonist - on subchronic olanzapine-induced depresion-like symptoms, sedation and hypertriglicerydemia. Forced swim test was conducted to determinate depressive-like effect of olanzapine and antidepressive-like activity during the co-administered pitolisant. The test was performed after the first and fifteenth day of the treatment of the mice. The spontaneous activity of the mice was measured on the fourteenth day of the treatment with a special, innovative RFID-system (Radio-frequency identification system) - TraffiCage (TSE-Systems, Germany). Triglyceride levels were determined on the sixteenth day of the experiment after 15 cycles of drug administration. Daily olanzapine treatment (4 mg/kg b.w., i.p., d.p.d) for 15 days significantly induces sedation (p < 0.05) and prolongs immobility time in forced swim tests (FST) in mice (p < 0.05); and also elevates the level of triglycerides (p < 0.05). Administration of pitolisant (10 mg/kg b.w., i.p.) subsequentto olanzapine normalizes these adverse effects. Reference: Metab Brain Dis. 2016 Oct;31(5):1023-9. https://pubmed.ncbi.nlm.nih.gov/27216278/
Solvent mg/mL mM
Solubility
Water 66.4 199.84
DMF 20.0 60.18
DMSO 43.1 129.57
PBS (pH 7.2) 10.0 30.09
Ethanol 10.0 30.09
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 332.31 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. 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. J Pharmacol Exp Ther. 2007 Jan;320(1):365-75. doi: 10.1124/jpet.106.111039. Epub 2006 Sep 27. PMID: 17005916. 2. Dudek M, Kuder K, Kołaczkowski M, Olczyk A, Żmudzka E, Rak A, Bednarski M, Pytka K, Sapa J, Kieć-Kononowicz K. H3 histamine receptor antagonist pitolisant reverses some subchronic disturbances induced by olanzapine in mice. Metab Brain Dis. 2016 Oct;31(5):1023-9. doi: 10.1007/s11011-016-9840-z. Epub 2016 May 24. PMID: 27216278; PMCID: PMC5031740. 3. 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. Biochem Pharmacol. 2007 Apr 15;73(8):1215-24. doi: 10.1016/j.bcp.2007.01.023. Epub 2007 Jan 21. PMID: 17343831.
In vitro protocol:
1. 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. J Pharmacol Exp Ther. 2007 Jan;320(1):365-75. doi: 10.1124/jpet.106.111039. Epub 2006 Sep 27. PMID: 17005916.
In vivo protocol:
1. Dudek M, Kuder K, Kołaczkowski M, Olczyk A, Żmudzka E, Rak A, Bednarski M, Pytka K, Sapa J, Kieć-Kononowicz K. H3 histamine receptor antagonist pitolisant reverses some subchronic disturbances induced by olanzapine in mice. Metab Brain Dis. 2016 Oct;31(5):1023-9. doi: 10.1007/s11011-016-9840-z. Epub 2016 May 24. PMID: 27216278; PMCID: PMC5031740. 2. 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. Biochem Pharmacol. 2007 Apr 15;73(8):1215-24. doi: 10.1016/j.bcp.2007.01.023. Epub 2007 Jan 21. PMID: 17343831.
1: Pitolisant Hydrochloride (Wakix): CADTH Reimbursement Review: Therapeutic area: Narcolepsy [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2023 Feb. Report No.: SR0715CL. PMID: 38502765. 2: Pitolisant Hydrochloride (Wakix): CADTH Reimbursement Recommendation: Indication: For the treatment of excessive daytime sleepiness or cataplexy in adult patients with narcolepsy [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2022 Dec. PMID: 38507534. 3: Imeri F, Stepanovska Tanturovska B, Zivkovic A, Enzmann G, Schwalm S, Pfeilschifter J, Homann T, Kleuser B, Engelhardt B, Stark H, Huwiler A. Novel compounds with dual S1P receptor agonist and histamine H3 receptor antagonist activities act protective in a mouse model of multiple sclerosis. Neuropharmacology. 2021 Mar 15;186:108464. doi: 10.1016/j.neuropharm.2021.108464. Epub 2021 Jan 16. PMID: 33460688. 4: Rusjan P, Sabioni P, Di Ciano P, Mansouri E, Boileau I, Laveillé A, Capet M, Duvauchelle T, Schwartz JC, Robert P, Le Foll B. Exploring occupancy of the histamine H3 receptor by pitolisant in humans using PET. Br J Pharmacol. 2020 Aug;177(15):3464-3472. doi: 10.1111/bph.15067. Epub 2020 May 23. PMID: 32293706; PMCID: PMC7348085. 5: Kallweit U, Bassetti CL. Pharmacological management of narcolepsy with and without cataplexy. Expert Opin Pharmacother. 2017 Jun;18(8):809-817. doi: 10.1080/14656566.2017.1323877. Epub 2017 May 17. PMID: 28443381. 6: Grosicki M, Wójcik T, Chlopicki S, Kieć-Kononowicz K. In vitro study of histamine and histamine receptor ligands influence on the adhesion of purified human eosinophils to endothelium. Eur J Pharmacol. 2016 Apr 15;777:49-59. doi: 10.1016/j.ejphar.2016.02.061. Epub 2016 Mar 3. PMID: 26939881. 7: Brabant C, Charlier Y, Tirelli E. The histamine H₃-receptor inverse agonist pitolisant improves fear memory in mice. Behav Brain Res. 2013 Apr 15;243:199-204. doi: 10.1016/j.bbr.2012.12.063. Epub 2013 Jan 14. PMID: 23327739. 8: Schwartz JC. The histamine H3 receptor: from discovery to clinical trials with pitolisant. Br J Pharmacol. 2011 Jun;163(4):713-21. doi: 10.1111/j.1476-5381.2011.01286.x. PMID: 21615387; PMCID: PMC3111674. 9: 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. J Pharmacol Exp Ther. 2007 Jan;320(1):365-75. doi: 10.1124/jpet.106.111039. Epub 2006 Sep 27. PMID: 17005916.

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