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

• ChemBase编号: 469
• 分子式: C23H28N2O3S
• 平均质量: 412.54502
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 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传统名: @cinalukast; 3-({3-[2-(4-cyclobutyl-1,3-thiazol-2-yl)ethenyl]phenyl}carbamoyl)-2,2-diethylpropanoic acid; cinalukast
• 商标名: Cinalukast [Usan:Inn]
• 别名: 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

登记号

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

理论计算性质

JChem

• Acid pKa: 4.3633976
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 4.4330173
• LogD (pH = 7.4): 2.6837933
• Log P: 5.4822445
• 摩尔折射率: 116.7488 cm^3
• 极化性: 44.28323 Å^3
• 极化表面积: 79.29 Å^2
• 可自由旋转的化学键: 9
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 4.98
• LOG S: -5.68
• 溶解度: 8.72e-04 g/l

分子性质

理化性质

• 溶解度: DMSO: >10 mg/mL; H2O: insoluble
• 外观: off-white
• 疏水性(logP): 4

安全信息

• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: human ... CYSLTR1(10800)

产品相关信息

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

详细说明

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.

参考文献

• 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)