CAS 128312-51-6|(E)-4-[[3-(2-(4-Cyclobutyl-2-thiazolyl)ethenyl)phenyl]amino]-2,2-diethyl-4-oxobutanoic acid|3-({3-[2-(4-cyclobutyl-1,3-thiazol-2-yl)ethenyl]phenyl}carbamoyl)-2,2-diethylpropanoic aci...

General Information

Structure

Molecular Formula

C₂₃H₂₈N₂O₃S

Molecular Mass

412.54502

Exact Mass

412.18206377

Charge

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+

InChIKey

BZMKNPGKXJAIDV-VAWYXSNFSA-N

Canonic Smiles

CCC(C(=O)O)(CC(=O)Nc1cccc(c1)/C=C/c1scc(n1)C1CCC1)CC

Isomeric Smiles

s1cc(nc1/C=C/c1cc(NC(=O)CC(CC)(CC)C(=O)O)ccc1)C1CCC1

Calculated Properties

JChem

LogD (pH = 7.4)

2.68

LogD (pH = 5.5)

4.43

Log P

5.48

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

false

Acid pKa

4.36

Polar Surface Area

79.29

Polarizability

46.90

Molar Refractivity

116.75

LOG S

-5.14

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Synonyms

Cinalukast(E)-4-[[3-(2-(4-Cyclobutyl-2-thiazolyl)ethenyl)phenyl]amino]-2,2-diethyl-4-oxobutanoic acidRo 24-5913Cinalukast4-[[3-[(1E)-2-(4-Cyclobutyl-2-thiazolyl)ethenyl]phenyl]amino]-2,2-diethyl-4-oxo-Butanoic Acid3'-((E)-2-(4-cyclobutyl-2-thiazolyl)vinyl)-2,2-diethylsuccinanilic acidcinalukast

IUPAC Traditional name

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

IUPAC name

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

Brand Name

Cinalukast [Usan:Inn]

International Nonproprietary Name (INN)

cinalukast

Names and Identifiers

Registration numbers

CAS Number

128312-51-6

MDL Number

MFCD00864778

PubChem SID

465057992472444716096393285331580

PubChem CID

6436135

DrugBank ID

DB00587

CompTox Database

DTXSID1045742

Drug Central Database

648

MetaboLights Database

MTBLS2871MTBLS2145MTBLS2406

CHEMBL

CHEBI ID

SureChEMBL Database

BindingDB Database

ACToR Database

128312-51-5128312-51-6

KEGG DRUG Database

D02846

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

Solubility

DMSO: >10 mg/mL

H2O: insoluble

Apperance

off-white

Product Information

Purity

~98% (HPLC)

Empirical Formula (Hill Notation)

C23H28N2O3S

Certificate of Analysis

Download link

Pharmacology Properties

Gene Information

human ... CYSLTR1(10800)

Safety Information

German water hazard class

MSDS Link

Download link

Personal Protective Equipment

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Storage Temperature

2-8°C

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB00587

Drug Groups

approved

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.

Indication

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

Pharmacology

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.

Affected Organisms

Humans and other mammals

Sigma Aldrich

C6239

Biochem/physiol Actions
Specific CysLT1 leukotriene receptor antagonist.

TRC

C441900

A novel leukotriene D4 antagonist.

ChEBI

CHEBI:126598

2,2-Diethylsuccinanilic acid substituted at a meta- position by an (E)-2-(4-cyclobutyl-1,3-thiazol-2-yl)ethenyl group. It selectively antagonizes leukotriene D4 at the cysteinyl leukotriene receptor, in the human airway, preventing airway edema, smooth muscle contraction, and enhanced secretion of thick, viscous mucus. It is used in the treatment of asthma.

Molecule Details

References

PubChem Literature

From Data Sources

• O'Donnell, M., et al.: J. Pharmacol. Exp. Ther., 259, 751 (1991)

• Jones, T., et al.: J. Physiol. Pharmacol., 73, 191 (1991)

• Kawano, T., et al.: J. Allergy Clin. Immunol., 112, 369 (1991)

References

Bioactivity

PubChem BioAssay

Bioactivity