timapiprant   Click here for help

GtoPdb Ligand ID: 9277

Synonyms: OC000459 | OC459
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Timapiprant (OC000459) is a potent, selective, and orally active DP2 receptor antagonist [1-2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 55.12
Molecular weight 348.13
XLogP 1.99
No. Lipinski's rules broken 0
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Canonical SMILES Fc1ccc2c(c1)c(Cc1ccc3c(n1)cccc3)c(n2CC(=O)O)C
Isomeric SMILES Fc1ccc2c(c1)c(Cc1ccc3c(n1)cccc3)c(n2CC(=O)O)C
InChI InChI=1S/C21H17FN2O2/c1-13-17(11-16-8-6-14-4-2-3-5-19(14)23-16)18-10-15(22)7-9-20(18)24(13)12-21(25)26/h2-10H,11-12H2,1H3,(H,25,26)
Bioactivity Comments
OC000459 inhibits mast cell-dependent activation of human Th2 lymphocytes and eosinophils [2]. It does not antagonise ligand binding at any of the other prostanoid receptors [2].
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
DP2 receptor Rn Antagonist Antagonist 8.5 pKi - 2
pKi 8.5 (Ki 3x10-9 M) [2]
Description: Displacement of [3H]PGD2 from rat recombinant DP2
DP2 receptor Primary target of this compound Hs Antagonist Antagonist 7.9 pKi - 2
pKi 7.9 (Ki 1.3x10-8 M) [2]
Description: Displacement of [3H]PGD2 from human recombinant DP2