Cinalukast - CAS 128312-51-6
Catalog number:
128312-51-6
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C23H28N2O3S
Molecular Weight:
412.55
COA:
Inquire
Targets:
Leukotriene Receptor
Description:
Cinalukast is a selective Leukotriene D4 receptor antagonist originated by Roche and IC 50 value is 6.4 nM. Cinalukast inhibits the actions of Leukotriene D4 at the CysLT1 receptor and it can prevent airway edema, smooth muscle contraction, and enhanced secretion of thick, viscous mucus. Treatment for Asthma was discontinued.
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Purity:
98 %
Appearance:
Off white powder
Synonyms:
Ro 24-5913; UNII-5E1O433QAI; CHEMBL283754;4-[[3-[(1E)-2-(4-Cyclobutyl-2-thiazolyl)ethenyl]phenyl]amino]-2,2-diethyl-4-oxo-Butanoic Acid
Solubility:
DMSO: >10 mg/mL
Storage:
-20°C Freezer
MSDS:
Inquire
Application:
Asthma
Quality Standard:
In-house standard
Shelf Life:
2 month in rt, long time
Quantity:
Milligrams-Grams
Density:
1.258g/cm3
InChIKey:
BZMKNPGKXJAIDV-VAWYXSNFSA-N
InChI:
InChI=1S/C23H28N2O3S/c1-3-23(4-2,22(27)28)14-20(26)24-18-10-5-7-16(13-18)11-12-21-25-19(15-29-21)17-8-6-9-17/h5,7,10-13,15,17H,3-4,6,8-9,14H2,1-2H3,(H,24,26)(H,27,28)/b12-11+
Canonical SMILES:
CCC(CC)(CC(=O)NC1=CC=CC(=C1)C=CC2=NC(=CS2)C3CCC3)C(=O)O
Current Developer:
Originator: Roche
1.Structure optimization of a leukotriene D4 antagonist by combinatorial chemistry in solution.
Maehr H1, Yang R. Bioorg Med Chem. 1997 Mar;5(3):493-6.
Structure optimization of the leukotriene D4 antagonist Ro24-5913 was attempted by combinatorial chemistry. Three segments in its N-succinyl-3-(2-thiazolylethenyl)anilide skeleton, designated as A, B, and C coincided with the thiazolyl, aniline, and N-acyl moieties, respectively, and were selected for variations in a synthesis involving the sequences A + B-->AB and AB + C-->ABC to furnish the library (10A 7B 10C) containing 700 compounds. Lead candidates were identified by the LTD4-induced muscle-contraction assay. Assays of the C-partition 10(10A 7B C) of the set led to a subset of C elements associated with significant bioactivities, ic = {C1, C2, C3}, from which the preferred element C1 was selected. Incorporating this selection into the synthesis of the first reduced set gave the partition 7(10A B C1) whose assay revealed the set iB = {B1, B6} and hence the preferred B element B1. The second reduced set, 10(A B1 C1) incorporating the selected C1 and B1 moieties, revealed iA = {A1, A3, A4, A6, A7, A8, A9} In the resulting combinatiorial product iA x iB x iC, comprising 42 elements, A1 B1 C1 appears on top of the list.
2.Participation of leukotriene C(4) in the regulation of suicidal erythrocyte death.
Foller M1, Mahmud H, Gu S, Wang K, Floride E, Kucherenko Y, Luik S, Laufer S, Lang F. J Physiol Pharmacol. 2009 Sep;60(3):135-43.
Eryptosis, the suicidal death of erythrocytes, is characterized by cell shrinkage and cell membrane scrambling with phosphatidylserine exposure at the erythrocyte surface. Eryptosis is triggered by increase in cytosolic Ca(2+) concentration upon energy depletion. The present study explored the involvement of leukotrienes. Western blotting was employed to detect the cysteinyl-leukotriene receptor cysLT1, competitive immune assay to determine leukotriene release from erythrocytes, Fluo3 fluorescence to estimate cytosolic Ca(2+) concentration, forward scatter to analyse cell volume and annexin V-binding to disclose phosphatidylserine exposure. As a result, erythrocytes expressed the leukotriene receptor CysLT1. Glucose depletion (24 hours) significantly increased the formation of the cysteinyl-leukotrienes C(4)/D(4)/E(4). Leukotriene C(4) (10 nM) increased Ca(2+) entry, decreased forward scatter, activated caspases 3 and 8, and stimulated annexin V-binding.
3.The investigation into indomethacin-induced potentiation of the contractile response to antigen in ovalbumin-sensitized guinea-pig tracheas.
Bozkurt TE1, Sahin-Erdemli I, Ilhan M. Fundam Clin Pharmacol. 2012 Jun;26(3):332-9. doi: 10.1111/j.1472-8206.2010.00918.x. Epub 2011 Jan 11.
In the present study, we investigated the mediators involved in the potentiation of antigen-induced contractions by indomethacin in tracheas isolated from ovalbumin (OA)-sensitized guinea-pigs. Indomethacin-induced potentiation of OA contraction was mimicked by prostaglandin DP/EP(1) /EP(2) receptor antagonist, AH-6809 but not by phospholipase A(2) enzyme inhibitor mepacrine. The lipoxygenase inhibitor AA-861 did not affect the contraction response to OA but prevented its potentiation by indomethacin, while the leukotriene receptor antagonist cinalukast inhibited both the OA response and its potentiation. However, the antagonists of platelet-activating factor (PAF) (BN-52021), adenosine (CGS-15943), endothelin ET(A) and ET(B) receptors (BQ-123, BQ-788), and the neutral endopeptidase inhibitor phosphoramidon did not alter the OA-induced contraction and its potentiation by indomethacin. Furthermore, capsaicin and neuropeptide receptor NK1, NK2, and NK3 antagonists (L-732128, MEN-10376, and SB-218795, respectively) also did not affect the OA-induced contractions and its potentiation.
4.Temperature sensitivity of suicidal erythrocyte death.
Föller M1, Braun M, Qadri SM, Lang E, Mahmud H, Lang F. Eur J Clin Invest. 2010 Jun;40(6):534-40. doi: 10.1111/j.1365-2362.2010.02296.x. Epub 2010 Apr 28.
BACKGROUND: Fever and hyperthermia are frequently associated with anaemia. Under most clinical conditions, they are considered to be two mutually independent clinical consequences of a common cause. The present study explored the possibility that anaemia results from temperature-sensitive suicidal erythrocyte death or eryptosis. Eryptosis is characterised by cell shrinkage and cell membrane scrambling with phosphatidylserine (PS) exposure at the erythrocyte surface. It is triggered by increase in the cytosolic Ca(2+) activity on the one hand and by ceramide formation on the other.
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