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)
1. Capra V, Bolla M, Belloni PA, Mezzetti M, Folco GC, Nicosia S, Rovati GE. (1998)
Pharmacological characterization of the cysteinyl-leukotriene antagonists CGP 45715A (iralukast) and CGP 57698 in human airways in vitro.
Br J Pharmacol, 123 (3): 590-8. [PMID:9504401]
2. Capra V, Carnini C, Accomazzo MR, Di Gennaro A, Fiumicelli M, Borroni E, Brivio I, Buccellati C, Mangano P, Carnevali S et al.. (2015)
Autocrine activity of cysteinyl leukotrienes in human vascular endothelial cells: Signaling through the CysLT₂ receptor.
Prostaglandins Other Lipid Mediat, 120: 115-25. [PMID:25839425]
3. Gusach A, Luginina A, Marin E, Brouillette RL, Besserer-Offroy É, Longpré JM, Ishchenko A, Popov P, Patel N, Fujimoto T et al.. (2019)
Structural basis of ligand selectivity and disease mutations in cysteinyl leukotriene receptors.
Nat Commun, 10 (1): 5573. DOI: 10.1038/s41467-019-13348-2 [PMID:31811124]
4. Heise CE, O'Dowd BF, Figueroa DJ, Sawyer N, Nguyen T, Im DS, Stocco R, Bellefeuille JN, Abramovitz M, Cheng R et al.. (2000)
Characterization of the human cysteinyl leukotriene 2 receptor.
J Biol Chem, 275 (39): 30531-6. [PMID:10851239]
5. Lynch KR, O'Neill GP, Liu Q, Im DS, Sawyer N, Metters KM, Coulombe N, Abramovitz M, Figueroa DJ, Zeng Z et al.. (1999)
Characterization of the human cysteinyl leukotriene CysLT1 receptor.
Nature, 399 (6738): 789-93. [PMID:10391245]
6. Ravasi S, Capra V, Panigalli T, Rovati GE, Nicosia S. (2002)
Pharmacological differences among CysLT(1) receptor antagonists with respect to LTC(4) and LTD(4) in human lung parenchyma.
Biochem Pharmacol, 63 (8): 1537-46. [PMID:11996896]
7. Sarau HM, Ames RS, Chambers J, Ellis C, Elshourbagy N, Foley JJ, Schmidt DB, Muccitelli RM, Jenkins O, Murdock PR et al.. (1999)
Identification, molecular cloning, expression, and characterization of a cysteinyl leukotriene receptor.
Mol Pharmacol, 56 (3): 657-63. [PMID:10462554]