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

• ChemBase ID: 469
• Molecular Formular: C23H28N2O3S
• Molecular Mass: 412.54502
• Monoisotopic Mass: 412.18206377
• SMILES: s1cc(nc1/C=C/c1cc(NC(=O)CC(CC)(CC)C(=O)O)ccc1)C1CCC1
• Canonical SMILES: CCC(C(=O)O)(CC(=O)Nc1cccc(c1)/C=C/c1scc(n1)C1CCC1)CC
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-({3-[(E)-2-(4-cyclobutyl-1,3-thiazol-2-yl)ethenyl]phenyl}carbamoyl)-2,2-diethylpropanoic acid; 3-({3-[2-(4-cyclobutyl-1,3-thiazol-2-yl)ethenyl]phenyl}carbamoyl)-2,2-diethylpropanoic acid
• IUPAC Traditional name: @cinalukast; 3-({3-[2-(4-cyclobutyl-1,3-thiazol-2-yl)ethenyl]phenyl}carbamoyl)-2,2-diethylpropanoic acid; cinalukast
• Brand Name: Cinalukast [Usan:Inn]
• Synonyms: Cinalukast; (E)-4-[[3-(2-(4-Cyclobutyl-2-thiazolyl)ethenyl)phenyl]amino]-2,2-diethyl-4-oxobutanoic acid; Ro 24-5913; Cinalukast; 4-[[3-[(1E)-2-(4-Cyclobutyl-2-thiazolyl)ethenyl]phenyl]amino]-2,2-diethyl-4-oxo-Butanoic Acid

Database IDs

• CAS Number: 128312-51-6
• MDL Number: MFCD00864778
• PubChem SID: 46505799; 24724447; 160963932
• PubChem CID: 6436135

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.3633976
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 4.4330173
• LogD (pH = 7.4): 2.6837933
• Log P: 5.4822445
• Molar Refractivity: 116.7488 cm^3
• Polarizability: 44.28323 Å^3
• Polar Surface Area: 79.29 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 4.98
• LOG S: -5.68
• Solubility (Water): 8.72e-04 g/l

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL; H2O: insoluble
• Apperance: off-white
• Hydrophobicity(logP): 4

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... CYSLTR1(10800)

Product Information

• Purity: ~98% (HPLC)
• Empirical Formula (Hill Notation): C23H28N2O3S

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.

Toronto Research Chemicals - C441900

A novel leukotriene D4 antagonist.

REFERENCES

• 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)