Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C26H34O5S |
Molecular Weight | 458.61 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O[C@H]([C@H](SCCC(O)=O)C1=C(CCCCCCCCC2=CC=CC=C2)C=CC=C1)C(O)=O
InChI
InChIKey=PZIFPMYXXCAOCC-JWQCQUIFSA-N
InChI=1S/C26H34O5S/c27-23(28)18-19-32-25(24(29)26(30)31)22-17-11-10-16-21(22)15-9-4-2-1-3-6-12-20-13-7-5-8-14-20/h5,7-8,10-11,13-14,16-17,24-25,29H,1-4,6,9,12,15,18-19H2,(H,27,28)(H,30,31)/t24-,25-/m1/s1
Pobilukast is the Leukotriene D4 receptor antagonist. Pobilukast significantly attenuated the Salmonella enteritidis endotoxin-induced thrombocytopenia but had no effect on either the endotoxin-induced early leukopenia or late leukocytosis. Additionally, Pobilukast significantly reduced the endotoxin-induced hemoconcentration and improved survival to 30% at 48 hr. Pobilukast dose-dependently inhibited the immediate hemodynamic changes after leukotriene D4 (LTD4) injections. Pobilukast also attenuated the increase in vascular permeability and the prolonged decrease in CO, suggesting that the observed cardiac and vascular effects of LTs were mediated by stimulation of LT receptors. A shift toward the right of the dose-response curves to histamine with pobilukast compared to that with placebo in three subjects was demonstrated, whereas the active compound did not exhibit any protective effect against histamine in the remaining nine subjects. It was concluded that there is a leukotriene component to the bronchial responses to histamine in some, but not all, subjects. Pobilukast had been in phase II clinical trial for the treatment of asthma. However, this development was discontinued.
Originator
Approval Year
PubMed
Title | Date | PubMed |
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Role of cysteinyl-leukotrienes and histamine in mediating intrinsic tone in isolated human bronchi. | 1994 Jan |
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Cysteinyl leukotrienes induce P-selectin expression in human endothelial cells via a non-CysLT1 receptor-mediated mechanism. | 1997 May |
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Identification and characterization of two cysteinyl-leukotriene high affinity binding sites with receptor characteristics in human lung parenchyma. | 1998 Apr |
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Pharmacology of leukotriene receptor antagonists. | 1998 Jun |
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Inhibition of 5-lipoxygenase diminishes neurally evoked tachykinergic contraction of guinea pig isolated airway. | 1998 May |
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Leukotriene C4 is a tight-binding inhibitor of microsomal glutathione transferase-1. Effects of leukotriene pathway modifiers. | 1999 Jan 22 |
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Identification, molecular cloning, expression, and characterization of a cysteinyl leukotriene receptor. | 1999 Sep |
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A kinetic binding study to evaluate the pharmacological profile of a specific leukotriene C(4) binding site not coupled to contraction in human lung parenchyma. | 2000 Jun |
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Lipoxin, leukotriene, and PDGF receptors cross-talk to regulate mesangial cell proliferation. | 2002 Nov |
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NCI_THESAURUS |
C29712
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100000081934
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C96710
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CHEMBL22776
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7179
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C052393
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107023-41-6
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60842
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R2N8IH71HC
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SUB09961MIG
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)