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Details

Stereochemistry ABSOLUTE
Molecular Formula C26H34O5S.C2H8N2.H2O
Molecular Weight 536.724
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of POBILUKAST EDAMINE

SMILES

O.NCCN.O[C@H]([C@H](SCCC(O)=O)C1=C(CCCCCCCCC2=CC=CC=C2)C=CC=C1)C(O)=O

InChI

InChIKey=DIUCVZXIHDZZBV-LBDKHHEASA-N
InChI=1S/C26H34O5S.C2H8N2.H2O/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;3-1-2-4;/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);1-4H2;1H2/t24-,25-;;/m1../s1

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C26H34O5S
Molecular Weight 458.61
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C2H8N2
Molecular Weight 60.0983
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Cysteinyl leukotrienes induce P-selectin expression in human endothelial cells via a non-CysLT1 receptor-mediated mechanism.
1997 May
Identification and characterization of two cysteinyl-leukotriene high affinity binding sites with receptor characteristics in human lung parenchyma.
1998 Apr
Pharmacology of leukotriene receptor antagonists.
1998 Jun
Inhibition of 5-lipoxygenase diminishes neurally evoked tachykinergic contraction of guinea pig isolated airway.
1998 May
Leukotriene C4 is a tight-binding inhibitor of microsomal glutathione transferase-1. Effects of leukotriene pathway modifiers.
1999 Jan 22
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:52:23 UTC 2023
Edited
by admin
on Fri Dec 15 17:52:23 UTC 2023
Record UNII
8270528Z3Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
POBILUKAST EDAMINE
USAN  
USAN  
Official Name English
Pobilukast edamine monohydrate [WHO-DD]
Common Name English
SK&F 104353-Q
Code English
SK&F-104353-Q
Code English
BENZENEPROPANOIC ACID, .BETA.-((2-CARBOXYETHYL)THIO)-.ALPHA.-HYDROXY-2-(8-PHENYLOCTYL)-, COMPD. WITH 1,2-ETHANEDIAMINE, HYDRATE (1:1:1), (.ALPHA.S,.BETA.R)-
Common Name English
BENZENEPROPANOIC ACID, .BETA.-((2-CARBOXYETHYL)THIO)-.ALPHA.-HYDROXY-2-(8-PHENYLOCTYL)-, (R-(R*,S*))-, COMPD. WITH 1,2-ETHANEDIAMINE (1:1), MONOHYDRATE
Common Name English
(2S,3R)-3-[(2-Carboxyethyl)thio]-3-[O-(8-phenyloctyl)phenyl]lactic acid, compound with ethylenediamine (1:1), monohydrate
Common Name English
POBILUKAST EDAMINE MONOHYDRATE
WHO-DD  
Common Name English
POBILUKAST EDAMINE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29712
Created by admin on Fri Dec 15 17:52:23 UTC 2023 , Edited by admin on Fri Dec 15 17:52:23 UTC 2023
Code System Code Type Description
MESH
C052393
Created by admin on Fri Dec 15 17:52:23 UTC 2023 , Edited by admin on Fri Dec 15 17:52:23 UTC 2023
PRIMARY
PUBCHEM
11954279
Created by admin on Fri Dec 15 17:52:23 UTC 2023 , Edited by admin on Fri Dec 15 17:52:23 UTC 2023
PRIMARY
EPA CompTox
DTXSID80929745
Created by admin on Fri Dec 15 17:52:23 UTC 2023 , Edited by admin on Fri Dec 15 17:52:23 UTC 2023
PRIMARY
FDA UNII
8270528Z3Y
Created by admin on Fri Dec 15 17:52:23 UTC 2023 , Edited by admin on Fri Dec 15 17:52:23 UTC 2023
PRIMARY
USAN
CC-41
Created by admin on Fri Dec 15 17:52:23 UTC 2023 , Edited by admin on Fri Dec 15 17:52:23 UTC 2023
PRIMARY
CAS
137232-03-2
Created by admin on Fri Dec 15 17:52:23 UTC 2023 , Edited by admin on Fri Dec 15 17:52:23 UTC 2023
PRIMARY
NCI_THESAURUS
C96711
Created by admin on Fri Dec 15 17:52:23 UTC 2023 , Edited by admin on Fri Dec 15 17:52:23 UTC 2023
PRIMARY
ChEMBL
CHEMBL22776
Created by admin on Fri Dec 15 17:52:23 UTC 2023 , Edited by admin on Fri Dec 15 17:52:23 UTC 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY