rupatadine   Click here for help

GtoPdb Ligand ID: 10103

Synonyms: Rinialer® | Rupafin® | UR-12592 [2] | UR12592
Approved drug Immunopharmacology Ligand
rupatadine is an approved drug (UK (2007))
Compound class: Synthetic organic
Comment: Rupatadine is a second generation histamine H1 receptor and platelet-activating factor (PAF) receptor antagonist [2,5]. It is selective, long-acting and non-sedating. It was designed as a single structure dual antagonist based on evidence that PAF appears to act alongside histamine in the pathogenesis of the allergic response.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 2
Topological polar surface area 29.02
Molecular weight 415.18
XLogP 4.12
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES Cc1cncc(c1)CN1CCC(=C2c3ccc(cc3CCc3c2nccc3)Cl)CC1
Isomeric SMILES Cc1cncc(c1)CN1CCC(=C2c3ccc(cc3CCc3c2nccc3)Cl)CC1
InChI InChI=1S/C26H26ClN3/c1-18-13-19(16-28-15-18)17-30-11-8-20(9-12-30)25-24-7-6-23(27)14-22(24)5-4-21-3-2-10-29-26(21)25/h2-3,6-7,10,13-16H,4-5,8-9,11-12,17H2,1H3
Bioactivity Comments
Rupatadine competitively inhibits PAF-induced platelet aggregation in human platelet-rich plasma with an IC50 of 680 nM [2].
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
H1 receptor Cp Antagonist Antagonist 7.0 pKi - 2
pKi 7.0 (Ki 1x10-7 M) [2]
Description: [3H]-pyrilamine binding to guinea pig cerebellum membranes.
PAF receptor Hs Antagonist Antagonist 5.4 pKi - 3
pKi 5.4 (Ki 3.7x10-6 M) [3]
H1 receptor Primary target of this compound Hs Antagonist Antagonist 8.4 pIC50 - 3
pIC50 8.4 (IC50 3.9x10-9 M) [3]