Cinalukast

Identification

Name

Cinalukast

Accession Number

DB00587

Description

Used in the treatment of asthma, cinalukast selectively antagonizes leukotriene D4 (LTD4) at the cysteinyl leukotriene receptor, CysLT1, in the human airway. Cinalukast inhibits the actions of LTD4 at the CysLT1 receptor, preventing airway edema, smooth muscle contraction, and enhanced secretion of thick, viscous mucus.

Type

Small Molecule

Groups

Experimental

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Cinalukast (DB00587)

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Weight

Average: 412.545
Monoisotopic: 412.182063462

Chemical Formula

C₂₃H₂₈N₂O₃S

Synonyms

• 3'-((E)-2-(4-cyclobutyl-2-thiazolyl)vinyl)-2,2-diethylsuccinanilic acid
• Cinalukast

External IDs

• RO 24-5913
• RO-24-5913

Pharmacology

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Indication

For Protection against second- phase inflamation in exercise-induced bronchoconstriction and Asthma.

Contraindications & Blackbox Warnings

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Pharmacodynamics

Used in the treatment of asthma, cinalukast selectively antagonizes leukotriene D4 (LTD₄) at the cysteinyl leukotriene receptor, CysLT1, in the human airway. Cinalukast inhibits the actions of LTD₄ at the CysLT1 receptor, preventing airway edema, smooth muscle contraction, and enhanced secretion of thick, viscous mucus.

Mechanism of action

Binds to the cysteinyl leukotriene receptor. The cysteinyl leukotrienes (LTC4, LTD₄, LTE4) are products of arachidonic acid metabolism and are released from various cells, including mast cells and eosinophils. These eicosanoids bind to cysteinyl leukotriene receptors (CysLT) found in the human airway. Cysteinyl leukotrienes and leukotriene receptor occupation have been correlated with the pathophysiology of asthma, including airway edema, smooth muscle contraction, and altered cellular activity associated with the inflammatory process, which contribute to the signs and symptoms of asthma.

Target	Actions	Organism
ACysteinyl leukotriene receptor 1	antagonist	Humans

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects

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Toxicity

Not Available

Affected organisms

• Humans and other mammals

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Not Available

Food Interactions

Not Available

Categories

Drug Categories

• Sulfur Compounds

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Anilides

Direct Parent

Anilides

Alternative Parents

Styrenes / N-arylamides / 2,4-disubstituted thiazoles / Fatty amides / Heteroaromatic compounds / Secondary carboxylic acid amides / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds

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Substituents

2,4-disubstituted 1,3-thiazole / Anilide / Aromatic heteromonocyclic compound / Azacycle / Azole / Carbonyl group / Carboxamide group / Carboxylic acid / Carboxylic acid derivative / Fatty acyl / Fatty amide / Heteroaromatic compound / Hydrocarbon derivative / Monocarboxylic acid or derivatives / N-arylamide / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organoheterocyclic compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Secondary carboxylic acid amide / Styrene / Thiazole

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Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

1,3-thiazole, carboxylic acid (CHEBI:126598)

Chemical Identifiers

UNII

5E1O433QAI

CAS number

128312-51-6

InChI Key

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+

IUPAC Name

3-({3-[(E)-2-(4-cyclobutyl-1,3-thiazol-2-yl)ethenyl]phenyl}carbamoyl)-2,2-diethylpropanoic acid

SMILES

CCC(CC)(CC(=O)NC1=CC(\C=C\C2=NC(=CS2)C2CCC2)=CC=C1)C(O)=O

References

General References

Not Available

External Links

Human Metabolome Database

HMDB0014725

KEGG Drug

D02846

PubChem Compound

6436135

PubChem Substance

46505799

ChemSpider

4940804

BindingDB

50064086

ChEBI

126598

ChEMBL

CHEMBL283754

ZINC

ZINC000003803377

Therapeutic Targets Database

DAP000976

PharmGKB

PA164743057

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
logP	4	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.000872 mg/mL	ALOGPS
logP	4.98	ALOGPS
logP	5.48	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	4.36	ChemAxon
pKa (Strongest Basic)	2.44	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.29 Å2	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	116.75 m3·mol-1	ChemAxon
Polarizability	45.8 Å3	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9315
Blood Brain Barrier	+	0.8337
Caco-2 permeable	-	0.6145
P-glycoprotein substrate	Substrate	0.5433
P-glycoprotein inhibitor I	Non-inhibitor	0.939
P-glycoprotein inhibitor II	Non-inhibitor	0.9373
Renal organic cation transporter	Non-inhibitor	0.9402
CYP450 2C9 substrate	Non-substrate	0.7695
CYP450 2D6 substrate	Non-substrate	0.8402
CYP450 3A4 substrate	Non-substrate	0.5901
CYP450 1A2 substrate	Non-inhibitor	0.7134
CYP450 2C9 inhibitor	Non-inhibitor	0.6524
CYP450 2D6 inhibitor	Non-inhibitor	0.9247
CYP450 2C19 inhibitor	Non-inhibitor	0.6193
CYP450 3A4 inhibitor	Inhibitor	0.7242
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.5806
Ames test	Non AMES toxic	0.7982
Carcinogenicity	Non-carcinogens	0.857
Biodegradation	Not ready biodegradable	0.9763
Rat acute toxicity	2.5159 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9993
hERG inhibition (predictor II)	Non-inhibitor	0.9064

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Targets

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Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	6.4	N/A	N/A	9554877

Details

Binding Properties1. Cysteinyl leukotriene receptor 1

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Antagonist

General Function

Leukotriene receptor activity

Specific Function

Receptor for cysteinyl leukotrienes mediating bronchoconstriction of individuals with and without asthma. Stimulation by LTD4 results in the contraction and proliferation of smooth muscle, edema, e...

Gene Name

CYSLTR1

Uniprot ID

Q9Y271

Uniprot Name

Cysteinyl leukotriene receptor 1

Molecular Weight

38540.55 Da

References

1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
2. Adelroth E, Inman MD, Summers E, Pace D, Modi M, O'Byrne PM: Prolonged protection against exercise-induced bronchoconstriction by the leukotriene D4-receptor antagonist cinalukast. J Allergy Clin Immunol. 1997 Feb;99(2):210-5. [PubMed:9042047]
3. Foller M, Mahmud H, Gu S, Wang K, Floride E, Kucherenko Y, Luik S, Laufer S, Lang F: Participation of leukotriene C(4) in the regulation of suicidal erythrocyte death. J Physiol Pharmacol. 2009 Sep;60(3):135-43. [PubMed:19826192]

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Drug created on June 13, 2005 13:24 / Updated on March 04, 2021 11:16