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Details

Stereochemistry ACHIRAL
Molecular Formula C23H28N2O3S
Molecular Weight 412.545
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CINALUKAST

SMILES

CCC(CC)(CC(=O)NC1=CC(\C=C\C2=NC(=CS2)C3CCC3)=CC=C1)C(O)=O

InChI

InChIKey=BZMKNPGKXJAIDV-VAWYXSNFSA-N
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+

HIDE SMILES / InChI
Cinalukast (Ro 24-5913 ) is a selective leukotriene D4 receptor antagonist originated by Roche. Cinalukast inhibits the actions of Leukotriene D4 at the cysteinyl leukotriene receptor, CysLT1, in the human airway. Leukotriene receptor occupation has been correlated with the pathophysiology of asthma, including airway edema and altered cellular activity associated with the inflammatory process, which contributes to the signs and symptoms of asthma. Cinalukast had been investigated for the treatment of asthma, but that study was discontinued.

Originator

Curator's Comment: # Hoffmann-La Roche

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q9Y271
Gene ID: 10800.0
Gene Symbol: CYSLTR1
Target Organism: Homo sapiens (Human)
6.4 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Ro 24-5913: a potent, specific, orally active LTD4 antagonist.
1991
Pharmacologic actions of Ro 24-5913, a novel antagonist of leukotriene D4.
1991 Nov
Patents

Sample Use Guides

in guinea pigs: i.v. (ID50 0.13 mg/kg), oral (ID50 0.12 mg/kg) and aerosol (IC50 0.008%) routes of administration.
Route of Administration: Other
In Vitro Use Guide
In vitro, Ro 24-5913 (cinalukast) competes with [3H]LTD4 for its binding site on guinea pig lung membranes with an IC50 of 6.4 +/- 2.2 nM. In isolated guinea pig tracheal smooth muscle, Ro 24-5913 produces concentration-dependent rightward shifts of LTD4-induced contraction curves (pA2 value of 9.6 +/- 0.2). The slope of the Schild plot is not significantly different from 1, indicating that the antagonism is of a competitive nature. In the human bronchus, Ro 24-5913 is an effective antagonist of LTD4-induced contractions (pKB of 9.3 +/- 0.1).
Name Type Language
CINALUKAST
INN   USAN  
USAN   INN  
Official Name English
BUTANOIC ACID, 4-((3-(2-(4-CYCLOBUTYL-2-THIAZOLYL)ETHENYL)PHENYL)AMINO)-2,2-DIETHYL-4-OXO-, (E)-
Common Name English
RO 24-5913
Code English
RO-245913
Code English
RO-24-5913
Code English
3'-((E)-2-(4-CYCLOBUTYL-2-THIAZOLYL)VINYL)-2,2-DIETHYLSUCCINANILIC ACID
Systematic Name English
cinalukast [INN]
Common Name English
CINALUKAST [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29712
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Code System Code Type Description
CHEBI
126598
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PRIMARY
USAN
FF-6
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DRUG BANK
DB00587
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EVMPD
SUB06282MIG
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CAS
128312-51-6
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SMS_ID
100000081038
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ChEMBL
CHEMBL283754
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PUBCHEM
6436135
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FDA UNII
5E1O433QAI
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INN
7094
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DRUG CENTRAL
648
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EPA CompTox
DTXSID1045742
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NCI_THESAURUS
C96709
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