2-[(2E)-3-(3,4-dimethoxyphenyl)prop-2-enamido]benzoic acid

• ChemBase编号: 5256
• 分子式: C18H17NO5
• 平均质量: 327.33128
• 单一同位素质量: 327.11067265
• SMILES: c1(c(NC(=O)/C=C/c2cc(c(cc2)OC)OC)cccc1)C(=O)O
• Canonical SMILES: COc1cc(/C=C/C(=O)Nc2ccccc2C(=O)O)ccc1OC
• InChI: InChI=1S/C18H17NO5/c1-23-15-9-7-12(11-16(15)24-2)8-10-17(20)19-14-6-4-3-5-13(14)18(21)22/h3-11H,1-2H3,(H,19,20)(H,21,22)/b10-8+
• InChIKey: NZHGWWWHIYHZNX-CSKARUKUSA-N

名称和登记号

名称

• IUPAC标准名: 2-[(2E)-3-(3,4-dimethoxyphenyl)prop-2-enamido]benzoic acid; 2-[3-(3,4-dimethoxyphenyl)prop-2-enamido]benzoic acid
• IUPAC传统名: tranilast
• 别名: 2-{[(2E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]amino}benzoic acid; 2-[3-(3,4-Dimethoxy-phenyl)-acryloylamino]-benzoic acid; 2-[[3-(3,4-Dimethoxyphenyl)-1-oxo-2-propenyl]amino] benzoic acid; 3,4-DAA; N-(3,4-Dimethoxycinnamoyl)anthranilic acid; SB-252218; Tranilast; 2-[[(2E)-3-(3,4-Dimethoxyphenyl)-1-oxo-2-propen-1-yl]amino]benzoic Acid; (E)-2-[[3-(3,4-Dimethoxyphenyl)-1-oxo-2-propenyl]amino]benzoic Acid; trans-Tranilast; Rizaben; SB 252218; MK 341; Tranpro; Tranilast(SB 252218)

登记号

• CAS号: 70806-55-2; 53902-12-8
• MDL号: MFCD00864787
• PubChem SID: 24278719; 160968685; 99444086
• PubChem CID: 5282230

理论计算性质

JChem

• Acid pKa: 3.5528402
• 质子受体: 5
• 质子供体: 2
• LogD (pH = 5.5): 1.6218046
• LogD (pH = 7.4): 0.20370603
• Log P: 3.5626285
• 摩尔折射率: 91.5198 cm^3
• 极化性: 33.853416 Å^3
• 极化表面积: 84.86 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.89
• LOG S: -4.59
• 溶解度: 8.40e-03 g/l

分子性质

理化性质

• 溶解度: DMSO: >10 mg/mL; H2O: insoluble
• 外观: white to beige powder
• 熔点: 166.2-168.2 °C(lit.)

安全信息

• 保存条件: -20°C
• 保存注意事项: IRRITANT
• RTECS编号: DG8731000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22
• 安全公开号: 26-36
• TSCA收录: false
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: human ... VEGFA(7422), VEGFB(7423), VEGFC(7424)

产品相关信息

• 纯度: ≥98% (HPLC)
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C18H17NO5

详细说明

DrugBank - DB07615

Drug information: experimental

Selleck Chemicals - S1439

Research Area: Rheumatoid arthritis, Hyp
Biological Activity:
Tranilast (Rizaben) is an antiallergic drug for bronchial asthma. It has been used for the treatment of allergic disorders such as asthma, allergic rhinitis and atopic dermatitis. It has also been investigated for use as an antiproliferative drug on drug-eluting stents. [1]

Sigma Aldrich - T0318

Biochem/physiol Actions
Tranilast is an anti-asthma drug, which inhibits LTC4 and PGE2 formation in stimulated monocytes, but does not inhibit cyclooxygenase or lipoxygenase activity; inhibits mast cell degranulation; inhibits VEGF-induced angiogenesis in vivo and also inhibits proliferation and tube formation of human endothelial cells in vitro. Tranilast may represent a new class of drugs for therapy to treat ongoing TH1-mediated autoimmune diseases.

Toronto Research Chemicals - T714565

Antiallergic drug, used to treat bronchial asthma, allergic rhinitis and atopic dermatitis.

参考文献

• http://en.wikipedia.org/wiki/Tranilast
• Shiota, N., et al.: Brit. J. Pharmacol., 159, 626 (2010)
• Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2010)
• Kawabata, Y., et al.: Eur. J. Pharm. Sci., 39, 256 (2010)