zafirlukast   Click here for help

GtoPdb Ligand ID: 3322

Synonyms: Accolate® | ICI-204219
Approved drug PDB Ligand Immunopharmacology Ligand
zafirlukast is an approved drug (FDA (1996))
Compound class: Synthetic organic
Comment: Zafirlukast is an oral leukotriene receptor antagonist (LTRA), with selectivity for cysteinyl leukotriene receptor 1 (CysLT1 receptor).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 11
Topological polar surface area 124.11
Molecular weight 575.21
XLogP 5.47
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES COc1cc(ccc1Cc1cn(c2c1cc(cc2)NC(=O)OC1CCCC1)C)C(=O)NS(=O)(=O)c1ccccc1C
Isomeric SMILES COc1cc(ccc1Cc1cn(c2c1cc(cc2)NC(=O)OC1CCCC1)C)C(=O)NS(=O)(=O)c1ccccc1C
InChI InChI=1S/C31H33N3O6S/c1-20-8-4-7-11-29(20)41(37,38)33-30(35)22-13-12-21(28(17-22)39-3)16-23-19-34(2)27-15-14-24(18-26(23)27)32-31(36)40-25-9-5-6-10-25/h4,7-8,11-15,17-19,25H,5-6,9-10,16H2,1-3H3,(H,32,36)(H,33,35)
InChI Key YEEZWCHGZNKEEK-UHFFFAOYSA-N
Bioactivity Comments
Zafirlukast shows low potency off-target effects on PPARγ and soluble epoxide hydrolase (sEH) [7].
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
CysLT2 receptor Hs Antagonist Antagonist 6.9 pA2 - 2
pA2 6.9 against LTC4 Ca2+ mobilisation assay in HUVEC [2]
CysLT1 receptor Primary target of this compound Hs Antagonist Antagonist 8.9 pKi - 1,5
pKi 8.9 zafirlukast is only about 100-fold selective for CysLT1 [1,5]
Description: against [3H]LTD4 in human lung parenchyma
CysLT1 receptor Primary target of this compound Hs Antagonist Antagonist 7.7 – 9.6 pIC50 - 4,6,8
pIC50 9.6 (IC50 2.6x10-10 M) against 33nM LTD4 Ca2+ mobilization assay in HEK-293 [6]
pIC50 8.6 – 8.7 (IC50 2.6x10-9 – 1.8x10-9 M) [4,6]
Description: against [3H]LTD4 in COS-7 or HEK-293 cells
pIC50 7.7 (IC50 2x10-8 M) against 10nM LTD4 aequorin-based Ca2+ assay in CHO cells [8]
CysLT2 receptor Hs Antagonist Antagonist 5.1 – 5.2 pIC50 - 3,8
pIC50 5.2 (IC50 7x10-6 M) against 10nM LTD4 aequorin-based Ca2+ assay in CHO cells [8]
pIC50 5.1 (IC50 7.397x10-6 M) againist [3H]LTD4 in COS-7 cells [3]
Selectivity at nuclear hormone receptors
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Peroxisome proliferator-activated receptor-γ Hs Agonist Agonist 5.6 pEC50 - 7
pEC50 5.6 (EC50 2.44x10-6 M) [7]
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
epoxide hydrolase 2 Hs Inhibitor Inhibition 5.7 pIC50 - 7
pIC50 5.7 (IC50 2x10-6 M) [7]