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128312-51-6 molecular structure
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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 and InChIs

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

Cite this record

CBID:469 http://www.chembase.cn/molecule-469.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
128312-51-6
MDL Number
MFCD00864778
PubChem SID
24724447
160963932
46505799
PubChem CID
6436135

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 4.3633976  H Acceptors
H Donor LogD (pH = 5.5) 4.4330173 
LogD (pH = 7.4) 2.6837933  Log P 5.4822445 
Molar Refractivity 116.7488 cm3 Polarizability 44.28323 Å3
Polar Surface Area 79.29 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P 4.98  LOG S -5.68 
Solubility (Water) 8.72e-04 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
DMSO: >10 mg/mL expand Show data source
H2O: insoluble expand Show data source
Apperance
off-white expand Show data source
Hydrophobicity(logP)
4 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
2-8°C expand Show data source
Gene Information
human ... CYSLTR1(10800) expand Show data source
Purity
~98% (HPLC) expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C23H28N2O3S expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00587 external link
Item Information
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 external link
Biochem/physiol Actions
Specific CysLT1 leukotriene receptor antagonist.
Toronto Research Chemicals - C441900 external link
A novel leukotriene D4 antagonist.

REFERENCES

REFERENCES

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  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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