3-[(3R)-3-(4-fluorobenzenesulfonamido)-2,3,4,9-tetrahydro-1H-carbazol-9-yl]propanoic acid

• ChemBase编号: 154383
• 分子式: C21H21FN2O4S
• 平均质量: 416.4658432
• 单一同位素质量: 416.12060638
• SMILES: c1ccc2c(c1)c1c(n2CCC(=O)O)CC[C@H](C1)NS(=O)(=O)c1ccc(cc1)F
• Canonical SMILES: OC(=O)CCn1c2CC[C@H](Cc2c2c1cccc2)NS(=O)(=O)c1ccc(cc1)F
• InChI: InChI=1S/C21H21FN2O4S/c22-14-5-8-16(9-6-14)29(27,28)23-15-7-10-20-18(13-15)17-3-1-2-4-19(17)24(20)12-11-21(25)26/h1-6,8-9,15,23H,7,10-13H2,(H,25,26)/t15-/m1/s1
• InChIKey: LDXDSHIEDAPSSA-OAHLLOKOSA-N

名称和登记号

名称

• IUPAC标准名: 3-[(3R)-3-(4-fluorobenzenesulfonamido)-2,3,4,9-tetrahydro-1H-carbazol-9-yl]propanoic acid
• IUPAC传统名: ramatroban
• 别名: (3R)-3-[[(4-Fluorophenyl)sulfonyl]amino]-1,2,3,4-tetrahydro-9H-carbazole-9-propanoic Acid; BAY-u 3405; Baynas; Ramatroban; BAY u3405; Ramatroban; (+)-(3R)-3-[[(4-Fluorophenyl)sulfonyl]amino]-1,2,3,4-tetrahydro-9H-carbazole-9-propanoic acid

登记号

• CAS号: 116649-85-5
• MDL号: MFCD00887606
• PubChem SID: 162248522
• PubChem CID: 123879

理论计算性质

• Acid pKa: 4.3877997
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 2.1616697
• LogD (pH = 7.4): 0.4054446
• Log P: 3.3045409
• 摩尔折射率: 107.0761 cm^3
• 极化性: 42.739445 Å^3
• 极化表面积: 88.4 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO: ≥40 mg/mL; H2O: insoluble
• 外观: white solid

安全信息

• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 1
• 危险公开号: 36/37/38
• 安全公开号: 26-36/37/39-45
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C21H21FN2O4S

详细说明

Sigma Aldrich - R0531

Biochem/physiol Actions
Ramatroban is used for the treatment of allergic rhinitis as an antagonist of the thromboxane receptor. It is also an antagonist of the DP2 receptor with IC50 values of 100-170 nM. It is more potent at the DP2 receptor than the TP receptor by 4-5 fold. It is therefore a useful tool for the elucidation of PGD2/DP2 function in eosinophils, basophils, and other cells of the TH2 cell-type.

Toronto Research Chemicals - R109000

A thromboxane receptor antagonist for use in the treatment of coronary artery disease.

参考文献

• Rahman, M., et al.: Int. Immunopharmacol., 6, 1736 (2006)
• Sato, T., et al.: J. Med. Chem., 51, 7705 (2006)
• Sandham, D., et al.: Bioorg. Med. Chem. Lett., 19, 4794 (2006)