CINALUKAST

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1658310 | http://adisinsight.springer.com/drugs/800001175

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cysteinyl leukotriene receptor 1 20 Target ID: Q9Y271 Gene ID: 10800.0 Gene Symbol: CYSLTR1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/1659286	Antagonist 2778		6.4 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Asthma 241 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23859232	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Ro 24-5913: a potent, specific, orally active LTD4 antagonist.	1991	1659286
Pharmacologic actions of Ro 24-5913, a novel antagonist of leukotriene D4.	1991 Nov	1658310

Patents

Sample Use Guides

In Vivo Use Guide

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

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