pitolisant   Click here for help

GtoPdb Ligand ID: 8924

Synonyms: BF2.649 | Ozawade® | tiprolisant [USAN] | Wakix®
Approved drug
pitolisant is an approved drug (EMA (2016), FDA (2019))
Compound class: Synthetic organic
Comment: Pitolisant is a selective antagonist/inverse agonist of the histamine H3 receptor [7-8,11].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 8
Topological polar surface area 12.47
Molecular weight 295.17
XLogP 3.94
No. Lipinski's rules broken 0
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Canonical SMILES Clc1ccc(cc1)CCCOCCCN1CCCCC1
Isomeric SMILES Clc1ccc(cc1)CCCOCCCN1CCCCC1
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
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
H3 receptor Primary target of this compound Hs Antagonist Antagonist 8.1 – 8.6 pKi - 6,11
pKi 8.1 – 8.6 (Ki 2.7x10-9 M) [6,11]
Description: Measured in a [125I]iodoproxyfan binding assay in cells exogenously expressing the human H3 receptor.
H1 receptor Hs Antagonist Antagonist 5.8 pKi - 6
pKi 5.8 [6]
H2 receptor Hs Antagonist Antagonist 5.0 pKi - 6
pKi 5.0 [6]
H4 receptor Hs Antagonist Antagonist <4.0 pKi - 6
pKi <4.0 (Ki >1x10-4 M) [6]
Ligand mentioned in the following text fields