pranlukast   Click here for help

GtoPdb Ligand ID: 3634

Synonyms: ONO RS-411
Approved drug PDB Ligand Immunopharmacology Ligand
pranlukast is an approved drug
Compound class: Synthetic organic
Comment: Pranlukast is a leukotriene receptor antagonist (LTRA), with selectivity for cysteinyl leukotriene receptor 1 (CysLT1 receptor). It is estimated to be 4500-fold selective for CysLT1 over CysLT2 in vitro [3].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 123
Molecular weight 481.18
XLogP 6.96
No. Lipinski's rules broken 1
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Canonical SMILES O=C(c1ccc(cc1)OCCCCc1ccccc1)Nc1cccc2c1oc(cc2=O)c1[nH]nnn1
Isomeric SMILES O=C(c1ccc(cc1)OCCCCc1ccccc1)Nc1cccc2c1oc(cc2=O)c1[nH]nnn1
InChI InChI=1S/C27H23N5O4/c33-23-17-24(26-29-31-32-30-26)36-25-21(23)10-6-11-22(25)28-27(34)19-12-14-20(15-13-19)35-16-5-4-9-18-7-2-1-3-8-18/h1-3,6-8,10-15,17H,4-5,9,16H2,(H,28,34)(H,29,30,31,32)
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
CysLT2 receptor Hs Antagonist Antagonist 7.1 pA2 - 2
pA2 7.1 [2]
Description: against LTC4 Ca2+ mobilization assay in HUVEC
CysLT1 receptor Primary target of this compound Hs Antagonist Antagonist 7.1 – 8.8 pKi - 1,6
pKi 7.1 – 8.8 [1,6]
Description: against [3H]LTD4 in human lung parenchyma
CysLT1 receptor Primary target of this compound Hs Antagonist Antagonist 8.1 – 10.0 pIC50 - 5,7
pIC50 10.0 (IC50 1x10-10 M) against 33nM LTD4 Ca2+ mobilization assay in HEK-293 [7]
pIC50 8.1 – 8.4 (IC50 7.2x10-9 – 4.3x10-9 M) against [3H]LTD4 in COS-7 or HEK-293 cells [5,7]
CysLT2 receptor Hs Antagonist Antagonist 5.4 pIC50 - 4
pIC50 5.4 (IC50 3.62x10-6 M) [4]
Description: against [3H]LTD4 in COS-7 cells